(552) From Building Startups to Betting on Them with Jason Gelman of Primary Ventures - YouTube https://www.youtube.com/watch?v=I5W1kCvbMXc

Transcript: (00:00) I'm excited to be joined today by Jason Gelman who is an operating partner at primary Ventures and co-founder of jump uh which is a revenue calendar for Revenue leaders which we'll learn a little bit about uh primary is an early stage Venture Capital fund so primarily seed and preed that uh takes a strategy of low volumes of Investments very high conviction uh strategy and then backs that portfolio with a ton of resources like Jason uh and they've backed companies like alloy Alma Chief electric calth vestwell (00:37) and many many more and prior to primary Jason spent four and a half years at Compass where he was the head of Revenue strategy and operations from somewhere around 100 million memories are hazy all the way through to A6 billion doll uh Revenue run rate and a successful IPO which raised $450 million in capital at the time uh so lots to get into and appreciate you joining me Jason thanks for having me and this is my very first podcast so I'm really excited about them good [Music] stuff hello and welcome to the revenue (01:15) leadership podcast by Topline I'm your host Kyle Norton C owner.com and every Wednesday we dive deep into the strategies and tactics being used to drive success by the best Revenue leaders in the world so join me as I sit down with Revenue operators to discuss actionable Frameworks that you can Implement in your business today with no fluff no sales pitches and no [Music] platitudes this episode of the revenue leadership podcast is brought to you by superhuman superhuman is an AI powered email app that helps sellers respond (01:59) collaborate and close faster with features like inbox triage automatic reminders and collaborative email drafts reps can filter out distractions to focus on what they do best selling get the email experience that keeps deals moving try superhuman free for 1 month at superhuman dcom Pavilion so what did I miss in the intro give people like your 60-second background anything that uh I failed to to cover there yeah sure so uh I actually started my career as a lawyer uh very quickly realized that that wasn't the thing for me and got an (02:35) opportunity to join uh to jump into the tech industry and have been there ever since uh in in the New York Tech scene I had this idea that I was going to be a business Builder I didn't quite know what that meant but I love the energy and the innovation in the tech world and that ended up manifesting itself in bizops and then kind of revops and uh that's that's where I uh really got my experience over about 13 years at four different companies uh two mtech SAS companies prior to Compass and then Compass was really Tech enabled and the (03:06) idea was let's bring the best of the go to market SAS Playbook to building a modern real estate burnbridge and then for the last two and a half years I've been at primary uh this is the first time working at a VC firm versus building an actual startup very cool uh so first question that people might be wondering what the heck is an operating partner yeah good place to start so uh an operating partner is uh somebody that works at a VC firm that does not write checks into startups or serve on boards usually uh but what they do is once the (03:41) check is written they bring some kind of uh functional expertise and domain expertise to working with the startup as a consultant advisor uh support system for those startups and the role really varies based on the stage that the VC firm invests in so I work at primary we are seed investors every time we invest in an amazing founder amazing company amazing Vision what are we also investing in pre-product Market fit Sales Early Scrappy hustle and so that's that's my version of being an operating partner you can imagine if you're a (04:18) series C or D uh VC firm your operating partner there is probably not rolling up their sleeves and doing creative things around how do we get our first customers it's much more the scaling the machine and and you know uh board level and strategy level topics makes a ton of sense um we could do an entire episode on Founder Le sales I get uh I think that's the most common LinkedIn message I get coming inbound is I got three or four customers what do I do how do I scale this thing it's it's uh it is a really difficult Chasm to cross uh and (04:56) so it's great to see that you guys are are supporting Founders there it's it's bad needed yep um and so it is operating partner in your previous title VP go to market is that largely the same just sort of a difference in your already now yeah that's right uh okay cool you know VC firms typically and and one of the things you have to learn if you ever do to join a VC firm is it's an investment firm it's not a startup and so some of the cultural things and the things about operating rhythms titles org design it's (05:27) it's just different than a startup and part partner at most firms uh has some maybe equivalency to like an accounting firm or a law firm where there's like a partner team and and so that that's really the only material difference is like I'm joined the partner team cool and so you'll work across every portfolio company uh with primary uh in some way yes but uh we have at least a 100 companies in our portfolio uh I don't work with all of those certainly some of them are you know scaling or growth stage companies where where I (06:00) might be able to help and and create less leverage uh but uh let's say there's a pool of 50 companies that I might be actively in touch with at a given time uh I could not possibly do deep work for 50 companies at once and so the the way that we try to do it is uh first there are certain companies that clearly need the most help or are asking for the most help that's one way we can sort of prioritize another one is companies that we just invested in and so we're a building a relationship building up our relationship and working (06:34) together and B that's a really important time for us to learn the business learn the customer so that's an example of how we could prioritize and there's a few other ways as well and so in reality what I'm doing is probably working very very closely with six to 10 companies at once keep and then I'm in touch and in rhythm with another 10 to 15 companies like whether it's a one toone or check-ins or you know trading notes or or doing some work there and then um I also do bring in outside Consultants at some points where there are direct (07:06) matter gaps gaps with domain expertise Gap that I I can't fill so like we do have other people that come in to help where I just don't have the right relevant experience nice okay cool um and so what's jump I read Revenue calendar I I didn't know what that was but it sounds interesting yeah so jump is a new startup that I'm a co-founder of with two other uh friends and partners of mine uh what we're doing is building a tool that's built for Revenue leaders so uh they are the user that we have in mind and it's really to solve (07:38) the problem that myself and my co-founder Jordan Kennedy have experienced ourselves over many years of uh running Revenue organizations uh and the short the short um explanation is that we think that the calendar for a sales Le organization has a lot of important data and insights but it's stuck in the calendar C and we have always had issues getting data out of the calendar to drive insights and impact and so that is the thesis for the company we're building and we're actually doing it uh in a different way (08:12) than the traditional VCB startup and I'm happy to explain more about that if if uh helpful yeah let's hear it yeah so um one of the reasons I joined primary was that I felt like there was a lot of uh Innovation happening in the world and when you're opting heads down at one startup it's very easy to like all the Innovations happening and you're just kind of focused and grinding and you know we're going to build the best tech enabled real estate Brokerage in the world and it's like well hold on what's happening in the rest of the world and (08:42) so part of joining primary was uh to really see a broader sense of innovation it was also though for me I had always had the ambition to start my own company and I felt like I needed a little bit of a creative spark again and so primary it's like I get to work with all these amazing Founders uh doing these really ambitious things and when we um when I got there and started to work with all these different Founders we uh you know I I got inspired like I said if if I'm coaching and teaching Founders how to do (09:13) this and bring a product into the market I got to be able to do this myself and so that was point one point two though is that when you work at a VC firm it really gives you sharp insight into which businesses should raise venture capital and which one shouldn't and interesting uh software Products that come in that solve problems for customers but that probably should not raise venture capital and Venture Capital you know you get on the VC treadmill you are really shooting for very very large outcomes and so VC is a (09:46) great tool for certain kinds of businesses that have the market the potential the um ambition ambition Innovation to like become an enduring iconic company um but then you see a lot of businesses and it's hard to uh figure out how how they're going to is that the best expression of the business and so when we came up with our idea for jump partly informed by my experience uh at primary I said I don't think I think this idea can help customers but I don't think it is a worthy uh uh business for Venture Capital um let's go one later deeper (10:25) there so you get a bunch of these companies coming across your desk uh how do you like to explain who should raise Venture versus who should bootstrap or you know go a different funding route yeah um I don't know that there's like a perfect one-size fits-all answer here but uh you know we're living in the age of sort of like AI Innovation and transformation and what what what used to require lots and lots of capital to get off a company or an idea off the ground doesn't require as much right now and so uh there's a lot of examples of (11:01) uh companies that maybe three or four years ago would raise Venture that should really could really be started as a test and and you know you can you can build a product get it to Market and validate the idea and keep optionality open and that so so one answer to this is a company that comes in has almost no product built or or a little bit of product and has no real like customer proof points may not be a great candidate for venture capital in today's day age especially in a crowded market like something like go to market SAS (11:33) where there's a lot of incumbents there's a lot of new entrance and the the lines are getting blurred across all these different categories and so each new company that comes in to raise a seed round the bar is just really really really high for a seed investor to say like how does this one company become the next gong or the next you know category defining business um so that's that's one uh which is like go go show that you have amazing Revenue traction and usage raction early and then raise Venture Capital because youve you've (12:02) clearly like broken through um the other one is uh I think that I think that people misunderstand like like I I probably understood this a little bit before I joined primary but now I really deeply understand it which is I think you raise from institutional investors even early stage you are in the VC game like me can raise a seed round but oh it's early and you know and but but every we only do as as a firm 12 to 15 deals a year and we see a thousand or more and so those 12 to 15 part of our underwriting and our our process for (12:45) research and diligence is like we're betting on a Founder a product and a market that has Ambitions to go big and some Founders may come in and not realize that uh you raise a seed round oh but you know I'll figure out what my growth Ambitions are later and you have to be really aligned with your investor on exactly what you're going for yeah makes a ton of sense um and so jump is trying to pull out information so you'll provide the calendar for a sales team to use that's better integrated into a CRM or a data data layer or something like (13:17) that yeah so jump what jump is doing uh we're gonna so our thesis is like unlock the calendar there's a lot of important things in the calendar and we're going to build uh three different products around that but the one that's live today that we're working with our very first customers on is called the revenue calendar and what it's doing is going into the calendars of all the different uh people that speak with customers in your organization SDR sales CS am and Leadership it is finding all the external meetings it's unifying them (13:45) onto One calendar so that if you're a revenue leader you're a CEO that's commercial leaning or you're any other VP or C Level that has to be in the flow of like what which customers are we meeting with it gives you one place to see all this information and the idea for us and the reason we built this was almost to solve like a problem that we had was um by the time you get to the call recording it's too late like the goal of Revenue leaders is that they provide the most leverage and you know by the time the call record the meeting (14:15) happens the call recording happens great you can coach and teach on what to do next but there's a lot of stuff that you can do if you if you know where to proactively intervene and your your Revenue leader you know like yourself your CEO every Monday morning you show up calendar is booked solid you you know you're already in tons of meetings every week uh you have to sort of Chase people around if if you want to know what the flow of the week and so for us it's like this gives you a chance to optimize your time as a leader your leverage and be (14:44) where you want to be whether that is helping internally uh Prep Prep for things or check on things and mitigate risks or it's external like I want to join three three customer calls a week and like which are the right ones for me to join very cool um okay let's get into our our two main topics so topic one is you making this operator to VC transition more and more folks are doing that so I'd love to understand why and how and lessons there and then we want to dive into what you've learned now on the investment (15:19) side that you wish you would have known as an operator because I think viewing the same problems from new angles is is such an interesting way to to uh acquire new mental models and and really uh learn so we'll unpack that for all the operators um so let's start with the the transition to to VC so uh a recent post of yours you mentioned why people advised you against going into it uh and obviously you did it anyways what what did what made you want to go into Venture in the first place yeah so uh I can't tell you that this was intentional (15:56) like I had a a specific uh plan to do this the opportunity did fall into my lab through a friend of mine that had been Consulting for primary and they were going to open this role they sort of talked to her about the role she couldn't do it they said who do you know that has an identical skill set to you and and she introduced them to me so that that's how RAR um when I was leaving Compass I did have some idea and I was doing some soul searching that I had done similar roles and I'd sort of climbed the ladder in Revenue strategy (16:27) and operations for for 12 or 13 years and I was ready for something new we had just gone through covid a very intense IPO process I had just started a family I just like my my priorities were changing a little bit and so I didn't know what new or different meant and and then this opportunity sort of materialized and so I I you know started to uh research it and develop my own thesis about it and I um talked to primary got excited talked to some mentors and they said don't do it and then I talked to primary again excited (16:56) and and then I talked to some more mentors and they said don't do it and don't do it um was like you know you're you're you're uh you're an adviser not a operator anymore like you're hanging up your guns kind of thing and so that was one two is like you don't really have any impact you're kind of like a little bit of a talking head and you're like a framework guy three was like um you're getting more senior in your career and like you're just at this point where like you you're you're well networked and you could like get the next you could be on (17:27) the next big rocket ship and so like if you miss that opportunity you know there's a huge opportunity cost to that um and there was a bunch of other things and so like that that's what I was hearing and then I started to say like okay let's make the most optimistic case for for trying this like what would be the reasons to do it and I started to just like cycle through these ideas over and over again so it was like one uh was information asymmetry I felt like in my career as a job candidate as someone who isn't particularly well networked or (17:57) like you know uh has a huge brand or audience in the world I go apply for jobs and I have zero information like ins access to inside information and you know every time you do one of these runs you do three four five years and it's like how do you know you're picking the right company and so said number one is if I go to a VC firm I'm gonna have a lot of information asymmetry the second thing is I don't have a big investor Network and my North Star at the time was I think I want to be a COO president of a company like that's that's like the (18:31) next big thing for me and I said if I was to if a great growth stage company was to open a COO type of role to to run the business with a CEO who's Technical and I was in the room why would I not get that job well um I have a lot of operational expertise I've done different business models I've scaled up different programs I've done more than just like the revops like tooling I've done a whole bunch of things and that's great but I've never fundraised I've never been in the boardroom PR the exec team for the board meeting and then I (19:02) wait for all the the dump of new projects I have to do after the board meeting but I've never been in there um and so I felt like the the investor side and the board meeting side was a big gap for me that I wanted to to fill um I also felt on the picking side like watching an investment firm analyze markets trends like across Industries across business models across customer personas was a level of access that I just had never had before and so uh and then the other one was I get to like be a trusted advisor to 50 of the (19:35) best early stage CEOs and uh I get to try before I buy and they get to try before they buy if if you know I find a mutual fit where I love the business and they love me like that's a they could pull me into their business that way um and then the last Factor was I said like hey I'm at a seed stage VC firm my instinct there was I was either gonna come into primary and eventually Join one of our portfolio companies as a COO or maybe I would get backed by primary and spin out a company and I'd be the founder and CEO and they would fund me (20:09) and I said okay so like that's that's like the positive side like that's what this this could unlock for me and the distinction that I really felt strongly about was everyone that told me not to do it it was like an impact thing it's like you're not going to have impact in this role and everything that I was excited about was a learning thing like wow this wow meet new people I'm going to be in board meetings like and so I I basically chose like learning over you know those concerns about like direct impact and like owning a specific (20:39) outcome and uh I can talk about the experience but I'm I'm very very happy I can tell you as someone who deals with a lot of early stage startups and therefore interacts with a lot of advisors and operating Partners there is a big opportunity for impact because I don't know how many times I hear a Founder tell me something that somebody else told them it's like oh you should think about doing this you should spin up this and my instinct is like that's a horrible idea like what's going on and and I conversely the right piece of (21:16) information for and insight the right framework for an early stage company can be really inflection changing and uh I mean lucky enough to sometimes get to share that nugget I get to see if founder who hears something from somebody else and and that transforms the way that a company operates I I would definitely like disagree with the uh assumption that like you can't have a lot of direct impact I get where it comes from like it's easy to think that from the outside but yeah um yeah and and a couple things to know about this (21:50) if for for anyone that would consider this role in the future your experience driving impact matter it matters a lot which VC firm you choose uh yeah some VC firms like I I I know other operating partners and the priorities for them if they had to stack rank them are diligence on New Deals LP reporting and presentations and then the third or fourth or fifth place thing is working with portfolio and so like if that's the firm you sign up with you will not feel like you're actually moving the needle for any of your portfolio companies um (22:23) when I did you know when I was like working through the decision process I made myself a promise and I said I will never ever be the Frameworks and you know storytelling and big idea guy like if I do this and I I don't feel like I'm solving problems and I'm just saying like gen you know generic Frameworks and uh sto you know inapplicable stories and things that aren't acable like I I was like I just can't be that person I'll never do this job if that's the case and so uh when I got here a big part of what I had to (22:53) explore in my first year was like where can I actually make an impact and what what are what is the firm doing today where it's either not making an impact or like the opportunity cost isn't right and there's like another area I should really try to drive leverage in and that that is an ongoing process two and a half years into the job like continuing to find the points where there's like outsize impact we can make for different types of companies yeah that makes sense I actually think Frameworks is one of the useful things if it's an actionable (23:19) framework and you know I I'll share with a Founder Founders are always trying to hire their one of the things I get roped into is how do I get my first vpa sales like how do I figure it out and give them my framework of how I think about hiring that VPS sales and the questions and the case like I I'll give them my case study that I've written and that's more valuable than any generic advice because they actually have a a guide to follow totally um so cool um we I'm gonna come back to this question of what makes a good operating partner versus (23:52) not um but I want to stay on some of this journey uh so what what made you realize that this was the right choice like how did you realize that primary was the right fit and and this is where you wanted to take your career I mean we've covered why why take this uh leap it's all about learning which I think is awesome but um what made you think like the timing was right today yeah so in terms of the timing uh I moved to my house so I left the New York City with in covid like a lot of other people scrambled suburbs uh I moved to my house (24:28) on March 22nd compass ipoed on April 1st I had my second kid on April 22nd so in one month of 2020 of 2021 uh okay all that 30 days and so I had hit a point of like uh General craziness and burnout that I just I like I needed something to change and the version of me that would have um met startup Founders and been like I'm all in on your vision and like let's go build this thing and do that again hours week signed me up yeah yeah and I went out and met all these Founders who I very inspired by but I walked away from those meetings just (25:05) saying like this isn't for me like I just don't have the energy for doing that right now and at the same time I felt like um I had hit a glass ceiling in my career as like you know the revops leader guy and for me it's like no I want to be the CEO or the COO of a company like that's that's my goal and so part of like the right time and the right uh place to do this was I felt like primary could elevate my career and unlock a lot more than like just joining the next series a startup and doing that over again makes sense um and how did (25:35) you know you were ready to do that like it's tough to know if you have enough operating experience to be able to have the pattern recognition and really be super helpful what gave you the confidence that that you're ready to take it on um I think so first of all like I didn't have a network in the VC world really I didn't have like a lot of people to bounce this off of um that that had done this job before so I was a little bit guessing but um I did a lot of back channeling on primary and they did a lot of back channeling on me and (26:05) it turns out the New York Tech scene ends up being really small and we back CH the exact same people at the same time and they're like kind of texting both of you about each other right now and what I heard about primary was it is in their DNA that they take the management fees that a lot of other VC firms put in their pockets and they invest it in this like really robust operating team and this will never go away this doesn't you know you know this isn't like a strategy Today Gone Tomorrow thing your DNA and (26:35) so that that was one two was I had um looked in in their portfolio and a bunch of the companies that I knew that they had just invested in which I would be working with I I felt like oh that kind of rhymes with something I did before or this kind of me of this other thing and like oh man I hope they don't make the same mistakes that I made five years ago and I had a little bit of that and then they they brought me as part of the pre-offer process to meet a few of the CEOs in the portfolio to mutually kind of feel it out and I love those Jam (27:06) sessions I thought they were amazing and they had good enough feedback about me that primary pooped in and was like let's do this so there there was a bunch of other uh signals like that um and you know I just got very very excited about all the the learning and growth that I would get inside of a VC firm like this nice awesome um do you think you want to be an invest partner at some point uh good question I think when I started I felt like I was opening new doors so door number one could be join a portfolio company as coo one day door (27:41) number two is like found my own startup through primary and get back by them they have an incubation program which I could talk about door number three was well what if I want to be an investor and so in the beginning it was very much an open question I think um for me personally the answer is no um um I I think our investors are unbelievably talented unbelievably bright and I have so much respect for them um but I I have so much identity as a builder and a problem solver and I I just like the idea of like bringing products to (28:15) customers and just really deeply woven in My DNA and what's nice is I get to work with Founders to do that and I have my own startup to do that and so all the things that I teach and coach the startup Founders on I'm doing myself it's like hey I'm trying to get first five customers and let me explain what I'm trying and then you know see if we can apply some learnings to your business so like that motivates me a lot more the investing thing um I do think I would Angel invest and and do that but not as like an investment partner at a (28:47) VC firm at least for the next you know 10 years or so yeah makes a ton of sense um so you said I can't remember if it's LinkedIn or somewhere else but you wouldn't have been good at VC 3 to 5 years ago so there's obviously you know an amount of experience a set of skills that are required to do this well and and I sort of break it into these two things like you need discernable skills to know how to build a growth model help architect a comp plan understand like do market analysis and those are very tangible skills but then there's some (29:21) like pattern recognition that you need to be able to develop by seeing a bunch of companies and just going through it yourself a bunch of times to actually be good at this job this is my my view having never done it obviously and so is that the right framework is it is it those two buckets of things and and if so um how do you think about uh when you have enough reps to have the pattern recognition how do you know when you've got the skills uh to go make take the plunge yeah yeah it's a good um it's a hard thing to explain but I it's like a (29:58) feeling I had like when I got here and I was in my first year I said wow I would not have been good at this job three or five years ago I actually think the biggest reason for this is my let's call it age group or class or or or contemporaries are now VPS heads of sea levels Founders and five years ago maybe they were the directors and up andc coming upand comers and Future Leaders but now they're like leaders and so one really important thing that would not be immediately obvious until you start like doing this role is every (30:34) single day one of the startups in our portfolio says to me I need help solving X and whatever X is one part of my job is almost like an account manager like I have to go out into the world and leverage my network of really trusted people or the people that they trust the most to bring them in to solve specific problems that are either in the go to market world or adjacent to it and to be able to like back Channel candidates with with with my contemporary network uh to be able to get functional expertise through my network uh these (31:10) last three to five years you know there's a huge wave of people that I've grown up in the industry with that are leading companies right now and I think that's actually the biggest reason is my network reach and my my closest uh friends that I've grown up with are now in these like leadership positions or or whatever and that that to me is the biggest one the second is also what you said about around business Acumen having a strategy mind like really being able to break down strategy and map it to execution every new cycle (31:40) you get doing that really helps um and part of the Heart part of the job is how do you go into a parachute into a new company where that the the founder and team have are thinking about this problem space five full days a week and you are thinking about it very very little and quickly get to a point of decent credibility that you can help solve problems without asking for a lot of training and and all that stuff and so learning how to be a really good consultant is a hard part of this job it's not anything I've had to do before (32:14) um and so like extra reps building different kinds of businesses or working on different kinds of uh problem solving at like compass for example I did a lot of things at Compass uh Under the Umbrella of Revenue strategy operations and each one of those things has been somehow applicable to my work here th this is literally one of the questions I had written down like one of my challenges doing advisory and working with the portfolio companies at GTM Fund in stage two is you have such a lack of context and and uh at some point in my (32:47) career I realized like hey there's no such thing as a best practice there's there's high probability practices there's things that like tend to work a lot but depends on the customer type the market context the stage of growth you're at and so I actually became this is classic Dunning Krueger but like I became much less certain of the advice that I wanted to give as I started to to understand sort of the nuance and complexity of it all and so how do you find the balance between having proven Frameworks that you like are confident (33:20) in and you've applied in your real world versus um finding the right Nuance in the business and and do you give great advice given these these two things are attention yeah uh yeah this is the hard part of the job so is the the thing that I've tried to do is each new company I work with it's like what is the quickest possible win that doesn't require the deepest amount of fluency in their business that I could find and just like solve one problem for them and if I can do that there's enough signal and and early (33:57) Trust that they'll invest time in me teaching me more about the nuances of their business and their customers and all these things and so that's number one for me is like what is the quickest smallest win that I can compartmentalize and deliver uh first second how often is that go smaller with your ICP uh it that that is sometimes um it's not usually goes smaller with your ICP because a lot of times they want to set of ICP experimentation like they they they know they don't ICP and so like they oh okay you're yeah you're (34:33) even earlier stage okay yeah it's like this is really early it's like I have no customers and no one wants to meet with me like what do I do and um and so we have to set up experiments and so like I think one framing I would give is I try to be a little less on the advice side and a little more on like the how do we design the action plan that we want and then let's go run a bunch of tests and go out in the world and and experience it together and and make decisions based off that um so that's that's one piece the second (35:01) piece is um there are a lot of I would call like basic uh basic foundations of go to market that a lot of these Founders need help setting up whether it's how to run a a sales meeting or how to like structure their Discovery questions to some basic tooling uh basic pricing and packaging to take to the market for the first time basic assets and the more you work with different companies the more you hear the same requests across a lot of them and then you're like okay hold on now I can invest in building some assets or (35:35) templates for for people because I'm getting the same question over and over um and so that's that's another thing we try to listen for is like where is the repeat demand for for the same things yeah makes a ton of [Music] sense are you being paid what you're worth Pavilion compensation report has become an industry standard for go to market leaders to Benchmark their compensation equity and other employment terms we're refreshing the port for 2025 and we need your input today to get early access to the results take the (36:08) anonymous survey at join [Music] pavilion.jpg I wish I had known that a couple years ago what are the couple what are the top few things in this first few years as an operating partner that you really wish you had known in your strategy and Ops World I think um from each startup I worked at there's some like lesson that has come back around working at a VC firm that like clicks after all these years um so for example uh one company I worked at had an unb believable team the best collection of talent that I've ever (37:01) worked with in my life but really had a product Market fit problem and we were able to as a growth organization and I I take very little credit for this like we had some like tremendously talented people and leaders there we were able to get this company to over 50 million AR um without uh like perfect product Market fit and and so like you you know anyone who's seen like scale up before you're ready story is a really painful one and then you see it from the VC side we have companies at seed A B C D and you see all these different uh companies (37:43) and some of them are like ready to have the like great unit economics great Foundation great everything and they're ready to like grow in a really thoughtful way and so like you you just see like your your past come back because you have exposure to all these different companies um and so product like like really hammering home like product Market fit and understanding like what uh delivering value to customers like really looks and feels like is is a big one um and I was laughing because I went through the exact same thing super talented team we (38:15) but we were brute forcing growth every deal had to be perfectly executed but we just never had product Market fit we never had customers that were willing to do customer reference calls for us but we still you know jammed business to 25 million ARR and uh yeah I I learned that same exact lesson very very much so just because you have the capital you know being like really honest with yourselves and finding the investors around your table who are really honest about like where the business is and and what the (38:45) next steps are I think is is helpful um the other can I ask one more question about that like how so how do you how do you identify that with a Founder what what should Founders or Revenue leaders be asking them elves to understand if they have enough product Market fit to go into you know go to market fit mode yeah um I think the biggest thing is some form of like sticky usage and then retention where it shows up in in the dollars um I I I don't think I think most Revenue leaders know the sort of state of their customer base and the (39:22) product quality and where they are as far as like the market dynamics I think the mismatches typically is like DCS want us to grow this way and we're only ready to grow that way and so let's hire too many salespeople or let's you know raise too much money and that mismatch is is the really hard one um and you know you you inside of a VC firm you just see every flavor possible of a different kind of company and I think the the the VC world uh the world of VCB startups has I think gotten very very sober uh over the last two years as far (39:54) as like what happened over the previous few years and so like big time that's that's changed um other things that you learn inside of a VC firm I think um I didn't know this at all VC firms have this unbelievable incentive to place talent in their portfolio and they they put a lot of resourcing into having talent programs um and it is actually like not that hard for an individual contributor a manager director VP cro to like sort of get inside of the network of a premier VC firm because every VC every VC wants to get shouted out in the (40:33) board meeting like my cro came from you know this firm um and so like this was like an aha moment for me like I got into primary having not known anyone at primary but now I see this Vibrant Community we've built all over New York and there might be three equally good candidates for a role in our portfolio one is very engaged with primary comes to an event you know uh helps us with reference references or um diligence on a deal or something and the other you know other one is sort of a little bit engaged and the other one we don't even (41:05) know who they are and that first person gets gets the first look at all these jobs so it is actually not that challenging to get in the talent network of a of a VC firm and I think even for Revenue leaders I think there's a lot of Revenue leaders in my network who understand this better than I did um but uh we ask for help with deal de de all the time we ask for help with references on leadership hires and individuals and so like there's a lot of value you can bring to a VC firm uh for for us and then also for yourself because you know (41:39) we obviously have a lot of uh opportunities you know roles board SE its advisory etc etc yeah I'm constantly trying to do this for GTM fund Port Co because my money's in the fund I want to make sure that the smartest people I know are the people running these businesses and so uh when people reach out hey I'm looking for something new it's like let me introduce you to a GTM fund folks or it it could be could be the same as primary it's it's uh yeah people that that is a great Insight folks don't understand I think people (42:13) are intimidated by Venture Capital funds like you see them as like oh they they have the money they're choosing the the winners and it can be intimidating to try to engage or build a relationship but at the end of the day the incentives are so aligned you know if you you want to help your friends like I want to help my uh friends and former colleagues find great jobs if they're good at what they do and these funds are dying to meet these people and so you can actually be helpful I think there's a friction there oftentimes yeah and one (42:47) thing that uh is you you experience in a different way inside of a VC firm you know that VCS have large networks they're they're well connected part of their job is to know a lot of people and and have networks built in different different places you get into a VC firm and you experience this and it's like oh my God it's a different level and so we can diligence a founder or a company within 24 hours like that like the the amount of access we have to getting back channels and answers and in private information is astounding and so one of (43:21) the things that you know there are people that I try to help uh find their next career opportunity and I I always say like send me a company that you're interested in and I guarantee you we can find some information good bad or otherwise that can help in your your decision uh that would not be publicly available so uh it it is uh pretty amazing how the network of VC works and how much you can sort of get to people questions uh research uh wherever you need it and uh VC firms are very very well positioned to do that (43:55) awesome um so we covered product Market fit Talent portfolio access anything else that you wish you knew as an operator like a lesson a pattern now that you've picked up that you think would have been valuable or you're going to take into your next operator role yeah I think um sort of back to the idea that we're starting jump as a not venture-backed company picking is very hard and as an operator once every three to five years hopefully you're now picking the next company and when you see the process that Venture investors take to (44:40) analyze a market understand where the sort of Puck is going in the next few years and where the value is going to ACR and you know in in the innovation in each category uh and the amount of research they put in the amount of diligence calls they do the amount of thesis building they do and then I remember me you know saying like two two of the executives from my prior company join compass and they turned around they're like hey Jason like you should come to Compass it's great I'm like yeah sure I'll come to Compass the the I was like oh my God and (45:14) so um one of the the things you can do is um you know knowing knowing the VC firm or people at them is you know that that information research exists and you know that there's really rich uh insights coming from that and so like I just the benefit that I have with learning from our investment team picking will make me an unbelievable uh unbelievably better picker in the future uh because of that what advice would you give to somebody that is a cro today they've just had a successful run they've got a good profile and they're (45:50) looking for their next like series B Revenue leadership opportunity how how would you tell them to go about the diligence ing process to make that right decision because you know like primary might make 12 bets a year and you make three bets a year as a as an operator like you gotta you gotta make sure it's it's a high quality call yeah that's for sure um so a couple things one is you you learn out of AC firm as well and and I think a lot of experienced C know this but maybe maybe people that are ascending into their first leadership (46:25) roles don't uh leadership hires run through executive search firms and there are a handful of executive search firms that partner with VC firms to do these executive searches and so realistically your ability to get access to the best roles partly depends on your ability to know nodes at VC firms and and people at executive search firms like that's like kind of where the the um the roles get originated and discussed and brought to Market um that's step one step two as far as like evaluating which companies um these are bets every single time (47:03) you're doing this you're making a bet and the more perfect the opportunity the more competitive it is like on paper and you know so these are all bets I think that um and and then the other really really challenging thing right now which I'm talking to more than a dozen people about looking for their next role AI has complicated everything like hard to pick right now um because of that and there's so much noise um I think uh I think the um networking your way to uh a VC that has access to like an investor deck or like a (47:39) fundraising memo or something like I I would want to get access to that information I don't know how often you know how how possible that how possible that is for everybody you can ask the founders if if you're interviewing for a cro role ask for the last ask for the last board deck yeah when when I was talking to owner about this this role the founder flipped me through a board deck and then I asked for time with the c the COO who ran finance and we went through the growth model in sort of like segment by segment like walk me through (48:11) the metrics of the business yeah that was growth and retention and unit economics and cash burn like we went through a screen share and spent an hour going through the details I think if you are interviewing for a especially like a a seite position or the ex itive sales leader like you you should be empowered to ask that and if it's a no in my opinion it's pretty big red flag because the the as long as you've gotten late enough in the process like you can't ask for the investor deck at I think that has become more uh standard practice I (48:48) think in the past few years where like before it wasn't like like the the company had leverage over the candidate and maybe wouldn't share I think that's becoming more standard today the other that might be interesting is um the primary for investing we use a framework called God of believes in every single investment and so we have an investment thesis so this is what would excite us about a particular business and it's like it's in this category with this paino and this you know Insight that these people have that we also agree (49:15) with that's the investment thesis so like why why do you like the opportunity and the the the debate the the research the the um diligence the underwriting is all about the God of beliefs and the god of believes are the unanswered questions the risks and to say okay if this business is going to be successful you got to believe that X will happen y will happen these are like the real decision points in each investment and that I will use that framework wherever I go like whatever I do like um I actually think it's very very clarifying and at (49:46) least you have a really explicit uh list of where you're making the bets like where is the risk and where where what are you betting on and hopefully some of those bets are somewhat in your control like it's it's distribution and go to market stuff is one of the god of beliefs it's uh it's you know scaling up the revenue organization to have certain kind of coverage or unlocking certain channels is a god of belief um and then as a revenue leader like okay I'm I have some control over that uh and so that that framework has uh been very very (50:16) clarifying for me and it's been fun to watch our investment team cycle through that hundreds of times in my my time here very cool have you guys uh shared that framework externally I I really like this got to belief concept I I believe we've talked about it publicly but I don't know if we've done like a full like write up on the process that be cool if we have I will find it and send it to you yeah we'll put it in the show notes that's a really it's a really interesting way to look at a to look at a deal because you have your (50:48) fundamentals is it a big Market is there product traction but that's a great way to highlight you know what what needs to be true and do I do we think these things can be true with some level of of confidence and a good example of this that comes up all the time is multiproduct you we know what we're investing in caps out at a certain size for whatever reason so one of the god of believes is that if you acquire customers in this segment and you deliver the first experience You' got to believe that that there's a cross- sell (51:18) motion to a second third and fourth product and so like those are those are some of like the tangible things that um that come up and then you part of your bet is like do I think this is a category where you know and and a Founder where the multiple product strategy is going to win or uh or not or something so there's a lot of that and then with AI um it's really hard to figure out the how to how to play the god of beliefs like you know we have a um we have a company that you know a lot of the viewers here probably know uh the (51:51) founder uh she Amanda Kao was the founder of six sense and now was oh I'm talking to her about one mind like actively yeah great so it right like this is a bet on the future like it's a bet that some portion of customer interactions will be done with uh some kind of AI Avatar and and her bet is really kind of to the most extreme that like lots of sales teams and individuals or customer success teams and individuals will get replaced by an AI Avatar and so like a god of believe is like you really have to believe that (52:23) that future is coming for some uh meaningful portion of um of the customer facing roles or or experiences that people have and so like this these are the examples of God of believes that like we wrestle with internally which is really fun very cool what advice would you give to to uh Revenue operators so like C Level called cro and Founders about managing VC relationships what do you know now that uh you didn't know from the compass days about how to how to master that Dynamic I think it's like the it's nothing uh (53:01) particularly wild or shocking it's like it's like really strong expectation setting really strong communication i i i frame everything I do with our Founders as if I were the CEO of your business here is what I would do like I I try not to give like advice as a coach I say like we we talk through the problem and then we say if I were the CEO of your business here's exactly what I would do I I think what I what say to that question is if I was the CEO of a business reporting to a board I would be very transparent I would be very (53:34) communicative no surprises consistent updates uh all of that and then of course like you you have to develop individual relationships with these these people uh and then there's a group Collective relationship and uh the people that manage boards well I think just do the basics really well they have a sense of maturity a sense of sort of like taking it seriously and then they build individual relationships with everybody in the boardroom or adjacent to the boardroom that's that's also helping uh helping them grow the (54:07) business um and so nothing nothing particularly special that I would I would call out why don't Founders execute on that like no surprises be transparent communicate a lot like why why it seems very straightforward why do you think people go wrong I think it's just extreme pressure uh creates moments of very um I don't know maybe not the best decision- making or something like in the moment like I think everybody one of these things like everybody would agree like of course like why wouldn't you do this and then things happen and moments come (54:45) up and uh it's also possible that like I don't know a VC uh or a board member is is not sort of being that value ad back to the CEO and so the attention can emerge from that and maybe don't want they want to manage that person a certain way so it's not just a oneway street um but I I I think it's just probably extreme extreme pressure extreme emotional roller coaster creates you know imperfection in in execution um but there's like a joke and a meme that goes around like LinkedIn and Twitter with the VCS it's like the the best (55:19) Founders are the ones who send the update on the first of the month every month always with consistency with the same metrics and like full transparency like you know just it makes sense yeah our founder talks about this a lot he's like we never we he used to do it before midnight the day the month closed and then we moved it to the first of the month and even that was like okay I'm going to make sure with the board it's cool and the board was obviously like yeah man like you know you can have a day to to get this to get this together (55:49) he had never missed uh New Year's Eve his birthday is is on the the 30th or 31st of the month like never never ever missed that deadline and it's like something in that uh investor update Channel he's like we don't miss this he's like this is a thing that is unequivocally like needs to happen and it you know just shows a level of professionalism and and seriousness that if you're going to bet a Founder you you absolutely need it to be there yeah um okay let's get into GTM Tech um and so I've never seen so much change happen in (56:26) such a rapid succession of time like it's uh I was really reflecting on this I was like is this just recency bias and we're always under change and no I'm I'm like certain that this is just a Bonkers time of of life um even if you look at sort of the two-year time Horizon Post gpt3 but even the last three to four months is arguably even more chaotic between deep seek operator reasoning models agents deep research you know like every every couple days it feels like there's some massive breakthrough there was some leak that uh open AI was (57:10) going to release a sales agent like yesterday and that's it's like oh my God I couldn't even I haven't even been able to read up on the Deep seek um uh uh visual like video thing yet because I was at an offsite now there's some new thing yeah and so um where the heck is GTM going in this world post AI reasoning agents like what's your what's your current theory yeah so I'm I have no idea the answer is I do not know but same here yeah and what's fun about this is I work at a VC firm and you know being on the ground (57:48) floor of the new generation of AI native goom Market tex. compan was not one of the reasons I originally joined primary but thank God I am at a VC firm for this AI explosion because this is the front row seat to like just learning and seeing every day like the next founder come into our office and explain where they think the world's going um it's a really really fun time it's impossible to know like our investors are so so smart and diligent they spent all their time thesis building around like what the future is going to look like and if (58:17) you ask them they would say they don't know so certainly I don't know either what I could say though is a couple of observations that may be helpful or interesting to the audience here first is um if you zoom all the way out we have like two decades of sass tools being built and and deployed in every organization and that's true of in every uh Department of every organization but let's just talk about go to market text so you got the Salesforce era where you have like Hub spotted or CRM and then the the vertical categories of (58:50) everything got built up there's the docu sign category there's the gong category there's the sales blop Outreach ategory there's this like huge uh deployment of SAS and then what's happening now is like this huge like retrofitting kind of thing where like AI is either being built inside of these old SAS products or like you're buying a new sass product but like connecting it to the old SAS products and there's going to be a few years of like figuring out like how did the all how does all of this like mesh together or do we like do (59:23) we need Salesforce anymore like what you know if in one move to New tools and it's going to be this like messy transition period and the question is like is five years from now like is all of that SAS gonna like go away like there's it's kind of possible that it does and one of the questions we're evaluating is like are these categories of tools even going to matter anymore like there's a pre-sales tool and a postsales tool and a call recorder tool and a thing and of course you've got like this uh compound startup Theory of (59:56) of what's Happening like Rippling is like the all-in-one bundle AI is g to do something like another level deeper than that like if Rippling is a a bundle of all the different point Solutions inside of a platform like AI is going to start to extract away all the platform stuff and and sort of like just do work and and create experiences without all this underlying like architecture and apis and connectivity and so like we're trying to figure out like what does this mean like how do you invest in stuff today what (1:00:30) um what uh what what should these tools be doing with our existing Tech stack or should they be trying to like replace them outright like these are these are and I think we've seen we we just pulled this stat I think we've seen 170 different go to market Tech Founders pitch Us in the last like 15 months or so lately every single pitch is AI native something or other um and some of them are trying to like start by replacing the SAS analog tool from before and saying like the doc you signed for AI and then we'll go do other (1:01:06) stuff others of them are saying like we're gonna uh combine a bunch of tools into our AI native thing some of them are AI native crms which is like a whole heads scratching world of like how do you everyone already has a CRM so like how do you unseat those CRM into your new like it's just it it is true and a CRM be probabilistic in nature like I don't know seems hard but maybe and then and then what's also really hard is that uh where the like value AC like where where you have pricing leverage in a tool historically so call recorder that (1:01:48) was their anchor product and that was an expensive product because it was a unique product and now there's a flood of great amazing call recorders on the market that are very very cheap and obviously gong is now like trying to build you know the platform and eat into everyone else's um categories but these these call recorders now are like so so good and so so cheap and so like you can imagine like each of these tools that comes out uh may start uh with some pricing leverage because like these Ari workflows are new but but as a early (1:02:22) stage investor you're like what is defensible such that you can maintain pricing leverage or or build a moat why why won't this all just be erased to the bottom over and over again like how do you like what what has a um any sort of defensibility is a very very hard question to figure out and so these are just some of the things we're thinking about one of the questions is like is there going to be um a tool that like truly does uh blur the lines between all the categories like is there just going to be one Mega (1:02:55) AI tool that like eats all the other software categories I think there's a chance that there is like um because because all the background orchestration could disappear you don't need this big revops and it team and all this other stuff so that's like that's the world that we're like trying to sift through and it's very very hard but I would not be surprised if one Mega GTM Tool uh emerges at some point that basically eats like tons and tons of the other workflows and outs yeah yeah it's I have I have sort of the (1:03:33) same questions in a similar hypothesis like at at what point you know I I people have always had their gripes about Salesforce it's always been you know a a tool that is extremely valuable but like people have frustrations with but I never thought in a million years there there's a a possibility that are unseated this is the first time I'm like oh man somebody could somebody could definitely get Salesforce now because if if you know that's basically just a series of workflows on top of a big database yeah and and what if none of (1:04:11) those fields matter what if none of the the way that information is structured and captured ma captures matters because yeah you know you could just throw it all into a massive database and like query into it any way you want seems like chaos to me gives me anxiety to think about but like maybe there's two fun thought experiments with this the first is like um okay so if you ever wanted to unseat sales force I agree with you that this is the only time I've ever seen where there's like this window where it could possibly happen but (1:04:44) what's the hard part is that if you are on Salesforce you have Integrations and other tool is bolted into it and this is why Salesforce was so smart they they built the App Store it's it's infinitely customized you have tons of it to unwind all that is very very hard especially for your like medium to large to extra large size organization so some AI tool will come along there's a bunch of these new startups that are like the AI native CRM and I think something will emerge as a massive company in that category but the question I would always (1:05:15) ask the founders would be like what happens when you run into the a company they're very large Salesforce is the incumbent they agree with you that like they're paying $4 million a year for this like massive Behemoth and they would get out of it but they just can't unwind the system so some like magic AI uh uh offboarding tool is gonna have to come along yeah that like can somehow like move systems make sure everything works the same and then kill sales fit into every little API that's possibly there and yeah and then the second fun (1:05:47) thought experiment and this is like why um investing is is really tricky uh in this because so let's say you have a thesis that like yeah like the data entry into a CRM is gone there are companies uh What mo momentum attention there's a few of these companies they watch your calls they put the notes in the CRM for you and we've like killed that workflow and save sales people a bunch of time okay great so like that's the future and we think that that workflow and technology is going to get democratized and that the idea of (1:06:17) manually data doing data entry in your CRM is gone well then it's like okay great so like if you you could invest in that a company that's like anchored on those kinds of workflows um but then like what if you believe that I don't know there's like an agentic future where lots of salespeople won't even be on calls and like then the agents the whoever builds the agent company won't need those companies to do that for them they'll just transcribe their own robot conversations themselves and so like what what um like if you know whatever this new (1:06:52) stack of AI is going to look like it's just so hard to figure out where does it go and what does the future look like and what does it mean for each new AI capability like where does the value acrew and who who wins in that world is a very very hard question to figure out yeah and something that I grapple with as an operator is I'm I'm trying to be on the front edge of it all and and we have like you mentioned momentum we were there third first third first second or third customer and we've got this AI Sim and (1:07:24) we were there first called aara first ping customer their first like design partner like I'm really trying to be the the advantage is so crazy and I was one of the very earliest salesloft customers earliest chili Piper customers earliest chorus customers I've always like carved an advantage like being early on sales Loft was wild like the the The Leverage I got above uh most other SAS companies and our competitors yeah and so we're trying to be early but I grapple with us all the time I'm like is this or is some (1:07:58) of this investment completely irrelevant in 12 months and um should the question is like do you wait a little bit longer to see how it all plays out uh and I've just come to the realization like I'm not a waiting person and like I prefer to make some mistakes along the way but but be early and carve an advantage there um but I'm certainly doing it with the understanding that some of these tools might be obsolete in some period of time because yeah you know I don't think it'll be Salesforce uh offering it but like something else could be could (1:08:38) be that layer I I if I were leading a company right now uh in leading a revenue organization I would do what you're doing which is make it a part of our DNA that we are constantly experimenting with AI tooling knowing that like we're going to create some churn some isn't going to work but it's much better to be at The Cutting Edge and and building like internal um IP around like what works for our motion and doesn't than to like wait and figure out where it all goes and the investor distinction is important like we get to (1:09:11) make one bet a year on a go to market SAS company maybe two and so that's our one bet and then like that's wild and so we have to think about like what does the world look like in five years if you're running a company that is sort of irrelevant like you can uh you know find the hard part though is filtering all the noise and figuring out like what's the one or two pilots I want to do right now um but I would absolutely be be aggressive with that and uh we did this thing a while ago at Compass uh for a sort of similar purpose we called it (1:09:45) like the sales lab and for a few months we had a few top sellers of maybe a top bdr a revops person kind of like in the lab partly because they wanted to be the experimenters on behalf of the whole group and tell everybody like what worked and what didn't and that that's probably what I would be doing right now if if I was running sort of like a scaling up organization um I do think that there will be some of these like like AI agencies that get to like very very large scale helping companies figure out the exact right (1:10:19) combination of AI Tech to implement I think those businesses are going to like explode in the next few years yeah yeah yeah it's going to be interesting because some of them have no idea what they're talking about like I I see some of the thought leader people putting out they're like oh I wrote a prompt for this and I'm no prompt writing expert but like I can read read some of this stuff I was like yeah this is sort of crap like it's either too generic enough to be helpful for anybody's business or it'll give you an output that's like a (1:10:49) cool party trick but actually not like materially helpful for a rep or or a leader it's it's I it's G to be such a challenging period of time for for leaders because like you and I I think have a predisposition to be interested in this stuff like you know I've been advising and Investing For I don't know five years or more and and uh have built enough pattern recognition to understand like when I pick a really early stage company it's really like a Founder bed and I'll do a pilot and I'll give the the uh Founders a bunch of feedback and (1:11:23) I'll see how fast they implement it and and I'm trying to align on like a vision do we have a shared vision of the the future in this category uh but I think most people just look at tools and like this is cool this will be helpful and then they send it and you can end up with three or four tools that and it's just Mass confusion across your team and very little value and you've wasted time energy and money to to sort of get nowhere yeah and so I I don't I I somebody was asking me for advice on this topic and and my advice (1:12:01) was like dude you got to go learn to be you got to go learn to be a venture capital investor basically to like know how to choose early stage Tech or or maybe just wait here's here's one one way you could approach this and we're doing this at primary right now for uh our our business development team one way you could take this is say okay let's map out our supply chain of how our go to market works so like from marketing to SDR to sales to conversion to post sales and where are we either like spending an outsized amount of time (1:12:35) or where uh like where's the place in that entire workflow that we would love to create leverage and the example from um primaries uh business development team is they're spending 15 hours or 20 hours a week just in sales Navigator so like they business development team functions like a bdr team basically um and 15 hours a week they're sales Navigator and then they have five or six other hours of spent on the prospecting motion and so play. (1:13:03) com to the rescue baby yeah for them is go find a tool uh or a workflow that gets you from 15 to 20 hours down to five per week per person like it's got to be sub five and so they have like a specific problem they're trying to solve and now we can go out to the world and say like hey all the new AI apps here's the exact thing we need to solve who can do this for me and they're taking demos with those companies so that's one way to think about it is like go out to that world with a very specific problem to solve and then see what you find in that Arena (1:13:34) because it otherwise everyone needs a filter right now it's too overwhelming there's too many tools they they all have some sort of like overlap with each other in some ways so you have to like pick apart what what each one does better than the other it's very very hard um and that's why I think AI agencies will there will be some that emerge that will be unbelievably huge because people need a trusted filter to say like don't worry about the noise you're paying me because I'm going to review everything and tell you what you (1:14:02) need I think that that is going to be a uh they're going to be some hundred million dollar Revenue AI consulting firms uh I think in the next few years yeah yeah if I wasn't so locked in and excited about owner that might be something I go start because I love the space and I feel bad for uh leaders that just so confusing and and the other advice I give to leaders is like you just have to make this a priority it's not really a choice like I sent Andre karpathy released like a three and a half hour video on the foundations of (1:14:38) llms how it works what's the difference between pre-training inference and and what's a token and how like how does this whole thing work and I sent it to my leadership Channel I'm like you got to watch this because everybody has to have enough foundational knowledge about this Tool Set uh because it's going to be the the foundation of how we all operate in the course of a couple years it's it's like being like I don't really need to know how to how a CRM works it's like no no no that's part of the job requirement yeah and so you got to find (1:15:09) the time yeah the other thing that um I I I think we're starting to do a primary um and i' I've talked to a few people who are doing this in their companies making AI like a theme at the company and like like say like uh whether you're an SDR uh uh in HR in finance and legal in sales and Leadership um making it like whether it's department or company level like hey it's this is the time of AI right now like this is It's the year of AI and anyone that has uh AI breakthroughs hey here's what I was doing before I found this AI workflow (1:15:49) I'm trying it and now it did this new thing for me here's what after looks like being visible celebrated loud inside of a company like that's what I would be doing because then it motivates other people to be like o I would love to find the that for my job and I think that would be a really fun way to do it inside of a company yeah for sure okay I could also do another hour on this topic but we got to go to the quickfire so you've gotten to work with a bunch of cro um H through primary and through your operating career in your mind what (1:16:21) separates a good cro from a truly great one uh interesting it is it is situation dependent I would say that the hardest skill set to that to find in a cro is the the classic is the best salesperson type at the company best sales leader and then the C like that path finding that person who is deeply analytically fluent and p&l fluent is very very hard and so a a really good cro certainly can uh uh be excellent at building managing and inspiring the sales organization and doing all the mechanics of like Talent developments (1:17:04) and all that other stuff the I think the best cro have pretty rich analytical fluency about like the numbers and mechanics of the business I have that in a substack article on the topic I couldn't agree more uh what's the most common advice you're giving to uh let's talk about Founders that are that have just found product Market fit and are starting to get into figuring out go to market um the common theme the most common theme I think there is a standard Playbook that everyone is used to it's like founder lead sales hire your first (1:17:48) AE and an SDR hire two more AES maybe then hire like a player coach AE then hire a VP sales and it corresponds to the funding rounds the thing I'm trying to do is for each business figure out if that's actually the right plan for that business I think there are some businesses where the founder should be the sole salesperson until like five or 10 million ARR and they should actually themselves with like other people and there are other variants of this uh so it it would probably be to question the sort of like traditional Playbook and (1:18:21) let's like really have a sharp and precise point of view on like is that right for this business and if it's not like let's find what is like I don't think it works in every scenario yeah uh that's really interesting um what's the hardest lesson you've had to learn in my career or Ina yeah in your career um going to law school realizing it wasn't for me and jumping into the tech world when like my family friends and entire network sort of like said you're a lawyer and you're you know this is who you are I took my medicine early I had I (1:18:57) struggled for a few years uh paying back loans and financially and I still have an extreme amount of paranoia about if you're not like proactive about your career and you don't you don't like uh have a vision for yourself the world will push you around and you'll be you'll be following other people's visions and so like taking my medicine early on that front has saved me a lot of pain down stream I think yeah for sure what's the best thing you've read in the last 12 months uh two of our investors uh at primary Brian Shor and Tobias Citron (1:19:37) there are Ai and infra investors they they invest in like the Deep Tech and the infra on AI they write this newsletter every month called the B&P newsletter Brian and Tobias and it's just like they were not experts in AI when this started and it's them documenting their learnings their questions their areas of exploration for the last two years and it's like I this is like exactly why I joined a VC firm uh to like learn from people like this and to like to see that they were not experts they're not technical they're (1:20:07) not Engineers by trade and they're learning this world it's like okay it's not that scary and they do such a good job with like Clarity of thought and taking you on the journey The Learning Journey that they're on so I I would uh and it's public anyone can read it I'll share the link with you what's it called BNT the B and T news infro newsletter okay um I didn't need another AI related newsletter in my life but uh I can't resist yeah so that's good um Jason this was awesome where can people find you what do you want them to go uh read plug (1:20:48) plug whatever you got yeah sure uh you've obviously find me on LinkedIn uh I I've started to do a little bit of writing on there with uh you know mixed emotions but I I think I have some things that I could share that could benefit other people and so I'm starting to do that uh and then my company jump is jumpr revenue. (1:21:08) com uh we we just launched recently so it's just a placeholder website for now and uh at primary we you know will meet early stage Founders even as they're ideating like we want to be ve very early and uh you know with you on your whole journey and so people that are starting a company I'm always is happy to chat with and see if we can help it anyway and tons of awesome content on the primary site too yeah you guys you guys push out some like actually high value stuff not just not just SEO uh content to try to rank like it's it's I've I've read a (1:21:43) bunch of primary content over the years and it's it's legit um thank you so all right well this was awesome I really appreciate you joining and uh we got through a lot and there were still like four hours of podcasting we could have done on some of this stuff so appreciate it yeah thanks so much [Music] K thank you for listening to the revenue leadership podcast if you enjoyed it don't forget to subscribe and you can find a link in the show notes and be sure to leave a five-star review share it with your network and please join me (1:22:17) next Wednesday for another great conversation