Finding the Right Fit for Your Company

with Jason Reichl,

CRO, TrustLayer

In this episode, Podcast Pete hits it off with Jason Reichl, the CRO at TrustLayer. From the launching pad of learning about Jason’s “revenue operations,” they get into everything from services versus SaaS and understanding enterprise motion.


Key topics in today’s conversation include:

  • Coining the term “revenue operations” (2:23)
  • The impending collapse of sales and marketing (9:41)
  • Jason’s consulting experience (13:09)
  • What a CRO does at a Series A company (17:38)
  • Where services versus SaaS makes sense (21:23)
  • Understanding enterprise motion (28:56)
  • Large versus small SaaS organizations (35:13)
  • Jason’s Wake Up GTM (39:03)


The SaaS(ramp) Podcast explores how tech leaders scale from product adoption to enterprise success. Learn more at


Pete Thornton 0:00
All right. Welcome to The SaaS(ramp) Podcast. I’m your host, Podcast Pete on with me today. Awesome guests. We have Jason Reichl, CRO at Welcome to the show, Jason.

Jason Reichl 0:18
Hello, Pete. I like that, Podcast Pete.

Pete Thornton 0:23
You run one of these. So like, you’ve got a podcast in the past you got a new thing that we can talk about coming out starting next week, they’ll definitely jump on at least for that first one. I saw the opening on my calendar. So do you have like an alter ego name?

Jason Reichl 0:36
I do not. If I get too drunk my friends call me Jason Baikal which is the evil version of me. So I guess that might be what I am on the podcast.

Pete Thornton 0:45
Oh my gosh. I love that. I tell my daughter a story. She’s seven. She’s Cosette and then we’ll do “Momette stories,” which is her alter ego and like, why got all the superpowers you know? That’s great, you know, sweet to her dad goes to bed on time. You know all the good stuff.

Jason Reichl 1:01
No, alter ego. I tried to… This is a funny thing because one of my biggest philosophies in life, not work-life balance but work-life integration and trying to be as authentic as you are in your personal life in your public life, and your work life, which can sometimes be fucking difficult. But to be honest, it’s much more enjoyable for me. I really enjoy putting all of myself and all my creativity and all of my business savvy into kind of everything I do. And so I’m Jason Reichl. That’s who I prefer to be.

Pete Thornton 1:33
Jason Reichl. Like Michael, but with an R. I was correcting the pronunciation of this so good. We didn’t know each other before the podcast. So sometimes I do know, folks before the podcast, if you’re at this point, you’re like, what is podcast all about? Then just go look at Jason’s LinkedIn profile. And everything he just said will be verified. That was my first impression. I looked at it. And I was like, Look at this. And I read through, like, I saw, like, the background on some of the organizations and things like that. And like, again, I won’t ruin it. I just like, Well, we’re here in his own words, shortly, but go check it out. And then just see if you don’t agree with everything he just said, as far as work-life integration and authenticity, perhaps. Alright, so we did this last time. I liked it. And you agreed, so we can flip the script a little bit? Let’s do some rapid-fire questions. And this will be mostly business-oriented. We’ll come back into the personal pieces, but feel free to flip back and forth. Biggest challenge last six months?

Jason Reichl 2:27
Well, the biggest challenges in the last six months is I started as a CRO at a series, an organization called TrustLayer. And TrustLayer is a very interesting company in what they’re trying to do in the commercial insurance space, which I’m not going to we can talk about that a bit. But what was interesting about it is I spent the last six years of my career working with very large organizations, like Twilio, and Zendesk And Coursera. At my own company, go nimbly, which I founded and was the CEO of and popularized the term revenue operations, which is a new form of basically how operations works at SAS companies. And those philosophies, those workflows worked in those large organizations. And I’m was very interested in taking all of that learning that I had done, and built out on around Reb ops and take it to a series a company and SI, does revenue operations does having a full-scale look and D siloing. of an organization impact early stage companies, do they move faster? Can they grow faster? Can they overcome problems that, you know companies have later in their trajectory. And so the last six months was putting that to the test, you know, rolling up my sleeves and getting into the dirt so to speak. And not, you know, working with companies who have unlimited budget, if you work with the Zen desks and toys of the world, they have a lot of money, and they can put a lot of money in solving these problems. If you work in a Series A company, you are operating in a different environment. And that was a very exciting thing and challenging thing to try to tackle.

Pete Thornton 3:57
That’s interesting. Well, let me back up a minute then. Because I’m ruining the rapid fire. Alright, as you can save it. Yeah, it’s this was all about. So when you’re talking about revenue operations being like a newer term enablement, a bit of a newer like, I mean, just it’s more progressive position. You’ll find it in hypergrowth, SaaS, a lot more than other places, for example, but with a requisite Reb ops, I’m like, Yeah, Reb ops, rev ops, like, it feels like that’s been around for a long time. But like, there, there is a version of Rev ops, that’s a little bit different that you’ve, you know, been putting your mind towards.

Jason Reichl 4:26
Yeah, so go nimbly was the first six years ago, we coined the term revenue operations or full-scale business stack. And the idea was around sales ops, marketing ops, ces ops, all coming into one and being a unified operations team and servicing the needs of the buyer over the needs of the organization. So you know, a lot of salespeople think that the sales team as an example, are their customer. In reality, everyone is working for our revenue and every buyer and experiences has gaps in them and what Go Nimbly As we touched hot teams how to prioritize your operational work based on the gaps that customers are experiencing, thus increasing your LTV. And that has been very successful. And I think over 45% of companies and b2b SaaS now have a revenue operations team. And I’ve moved away from sales operations, marketing ops, and so to speak in the last six years. And it’s really been over the last two years that companies have really made this change. So it felt like for the first four years, I was yelling into the darkness, and then suddenly, some lights came on. And then that’s when I started doing all the speaking engagements and panels and podcasts and all this kind of stuff around revenue operations and started to build the frameworks that are now implemented at many organizations. And I in you know, to be quite honest, I want to write a field manual for organizations from startup to success. And so that was part of this core idea of moving the TrustLayer and understanding what works and what doesn’t work at each stage of a company firsthand.

Pete Thornton 6:00
This is interesting. So you’re like running your own experiment right now, based on what had worked with more enterprise-grade customers or like companies and then detracting it. Was there a pain point that you’re trying to overcome? Like, like, why? I know, you mentioned from an economic standpoint, like budgetary standpoint, like you’re not going to have as much budget in a Series A obviously not necessarily Bootstrap, but like, not massively funded. So then, so is there something that like you’re trying to get down to a more basic level are you trying to slide in before problems starts, you’re not having to—

Jason Reichl 6:33
Right. You’re hitting the nail on the head. The hypothesis was, when I looked at what customers were spending to do a conversion, say when they are series D, or trying to IPO into a revenue operations team. It could be in the tune of, you know, two to $3 million just on trying to do that transformation, internally hiring the right people diversifying and bringing skill sets up. And that all starts at decisions that were made in the tech stack and the strategy from day one. And so what the hypothesis was is can a company save that money from being smart in the very beginning? Because one thing that companies often do in a startup phase, which I think we all have experienced if you’re working in SaaS, is good enough. And I believe it’s not good enough. It’s the right size fit for the inflection point that you are. So yeah, series, a company doesn’t need the operations of a company about to IPO. But it’s not good enough. Do we have the correct operational standards for where we are knowing that in a series a company by the time you get further along in this path, and you’re you know, you’re doing 20 or $30 million in revenue, you’re going to be a very different companies, SaaS companies go through very many different changes. And technically, I think having worked in different organizations at different inflection points, they’re, they’re different companies, even if they’re selling the same product or an expanded version of that product. And so it’s really understanding what does operational excellence look like when you have a 30? person team? And then what does operational excellence look like? When you have a 300? person team? It’s very different. And the buyers are different based on those kinds of organizations. So that was really what I thought would be interesting is can you go in and from moment one, show that there is operational excellence to be had in every inflection point of a business and to Cana CRO because, again, my background was I was Product Management. I was the CEO, I was a salesperson, but mostly I believed in all of these functions as an operational-minded person, the CRO, and historically and SaaS has come from a sales pure sales background. And a lot of times, this is changing, but we’re more like VP sales, people who only kind of focus on sales. And my background is in advertising and marketing. And so I really believe that CROs should own both sales, marketing and customer success, all three of those parts of the organization that touched the buyer journey. And so I wanted to see what does an operational CRO look like? What does it mean? What does an operational CRO who cares about excellence and process look at like at a series a company, of course, what TrustLayer and what I’ve implemented as process might get laughed, right? Because the processes need to be very different. We need very flexible processes at TrustLayer. And Salesforce needs very rigid processes at where they are, but we both have processes. We both have the operational recipes that are going to make us successful.

Pete Thornton 9:35
Okay. Yeah, comment to that is that the in these more progressive organizations like Postman, for example. Postman’s pure product lead growth, so they were doing extremely well with like, it was maybe like 12 million developers use the platform when I came on board, and they were going to launch an enterprise motion. That enterprise motion didn’t even exist and they were already in this massive ascent on just the Self Service. So I was hired by the leader of customer success. And then two months after I was hired brought in leaders for sales, customer success and solution engineering under the customer success umbrella. And it’s only more recently that sales has moved out of that customer success umbrella at all.

Jason Reichl 10:17
Very similar structure and experiences to two organizations that I worked within, it helped them operationally setup, which was pager duty and Twilio, both of those organizations were developer-led organizations that had huge user bases before they ever even created a sales motion, as they wanted to go up into the more enterprise and make sure that they were actually getting an account penetration, they had to build a sales team and a marketing team and all of those types of things. But for a foreseeable part of that company’s history, it was developer-led, it was enablement, it was documentation that was really driving the use case and allowed the organization to grow. I think, you know, I can’t name numbers here. But like pager duties biggest cup customer was Uber and they had never really talked to Uber until it was a massive organization. And because some developers signed up for pager duty to do a text alerts way back when Uber was, you know, in its infancy. So those kinds of stories and those kind of go-to-market stories, as I like to call them are very interesting. But to me, they’re all the same. That is sales and marketing, that is customer success. Because I actually believe that in the future, these roles are going to collapse. The functional layer that separates sales and marketing and marketing and customer success are eradicating at a very rapid pace. And in 20 years, you won’t be able to get a job as a salesperson, if you don’t know how to write copy, you won’t know how to, you won’t get a job as a CS person if you don’t know how to upsell and cross-sell to your existing customers. And so all of these kinds of gaps, these chasms are being bridged now, with smart processes and generalist-minded people.

Pete Thornton 12:00
Interesting. It is interesting because there are challenges that I’m experiencing now as enablement leader that I’ve never seen before. Because it just like weird is the customer like you’re looking at it from customer journey perspective, which is the best you can ever do. But you’re like, where do people fit, so I can tell them where alignment would be in handoffs would be, and it’s just not a top-down sales motion. So it doesn’t just start here with marketing and move to business development team and move to sales and move to CES. It’s not clean. But it’s so much more. It just works better, though. So you’re like, Yeah, what do you do, it’s a little messy underneath, but like it’s, and then we’ve hired people in, I call them the pager duty mafia, because it’s like, because they come from these certain kinds of companies, and they understand that process of at least what it looked like in a more similar way. And it’s super-valuable to be like, okay, so how did this look for the last four years for you? Great, because we’re about to go through it here. And then we have another layer of leadership, who’s come on from GitHub, and put some live API of get I’m gonna get that, what do we call it just like the GitHub of API’s as essentially kind of like, what they’re thinking of it in that framework. With Go Nimbly, did you do this from a services standpoint? Did you come in and consult to these companies?

Jason Reichl 13:09
Yeah, Go Nimbly is a consultancy. So before Go Nimbly, I worked in SaaS as a product manager. And I saw that the best products were great but kind of didn’t go anywhere without a very strong go-to-market team. And I had worked in the past, previous to being a product manager in sales and marketing, customer success. And so I thought, hey, we can probably operationalize and package up and tell organizations where to look, based on their inflection point, that was the premise it was called Unified business stack. That is what before it was row ops, that’s what I called it. And the unified business stack idea was then taken to organizations and behind the scenes go nimbly had built different pieces of software that allowed us to consult more like a subscription model. So we were a subscription agency and really helped them transform that organization into their own Reb ops team. So sometimes we augmented sometimes we consulted, sometimes it was just identifying gaps in their process, all sorts of different use cases, more like a full-scale agency model. And we thought of ourselves as partnered with those agencies for the long term. And as far as consulting goes, the customers tended to stay with our organization much longer than traditional consulting models because we were powered by technology, and that background and SaaS. And then on top of that, we were kind of leading in the forefront of what revenue operations could look like and what it actually meant, you know, through that experience, you know, I think there are numbers are published now, not just from going nimbly, but you could see that by implementing revenue operations by really focusing on GTM as a craft, you could increase with not people not SDRs, but just with the quality of improving the buyer journey. You can improve the dollars that you would get by somewhere Between 10 and 36%. So having these different teams all segmented actually meant that somehow in the buyer journey, the customer is experiencing gaps and losing faith in your organization and revenue operations, whole entire goal is to fill in those gaps. Hopefully, it makes life internally better. But if it doesn’t, that’s okay. But they fill in those gaps for those customers. So that customer is willing to sign a longer contract, go out on a limb and bring your software across, its, you know, that entire organization willing to refer you willing to do all of these things that are actually really important post, I hate to say posts, I don’t think we’re post COVID. But post COVID, where, you know, we don’t have the same methods working anymore. You know, you can’t just number dial enough people and catch them in their office and sell your SaaS product, we need much more sophisticated mechanisms to actually win customers and then expand customers, I think, you know, one of the two things I said very early on when I started go nimbly is the two most untapped revenue sources for a SaaS company are its revenue operations teams, so the people that are actually connecting things, and it’s service team, you know, it’s CS team is the untapped thing. And I really believe that the value differentiator between products in the next 10 years is going to be those two factors. So if you have two software’s that have similar features, the one that’s going to win is the one that’s going to have a better row ops team and a better CS team because those are value differentiators that customers actually experience. And we’ve moved into the age of experience features are okay, but what’s the experience that the person is having? How much political capital and an uncertain time are they going to have to put out to buy your product? And the answer should be next to zero. Right, that should be answered that should be the goal of every organization to get that to zero. You know, the idea of who’s my champion, now champion us internally, is a false premise because you should turn that organization and everyone in that structure into your champion. And I think that you do that through smart operations and CS.

Pete Thornton 17:02
Yeah, it sounds like it’s like many of the things I’ve experienced in just the past two years. In particular, when you’re bringing this to larger organizations—like Twilio, like a pager duty, like, of course era—what is different in your day-to-day CRO role? Like your role right now. You’re chief revenue officer, you’re at a Series A company, you’re kind of testing these things internally. So like, the in number is obviously one at this point. But your duties are probably expanded across, like you mentioned a big deal recently, et cetera, things like that. So how is it really different?

Jason Reichl 17:38
Well, I did a Series A, I’m involved in a lot more, a lot more people management, a lot more, a lot more interpersonal management, the kind of people who work at a startup in a Series A are sort of different kinds of people that work at a pre IPO tech company, right? They’re different, they’re a different breed both good and bad. So you’re working with sometimes a lot more egos. Sometimes you’re working with people who, in a series, a company, very committed to the things that have gotten them there, right, because every step in that first two-year period, from seed to state, you know, the endpoint of Series A is a grind, it’s very difficult. And, you know, if a process worked, they’re very hesitant to let go of that process. Whereas when you work on an enterprise, if you say, hey, that worked six months ago, but it’s no longer working, they’re much more quick to change, probably not much more quick to implement process, but much more quick to hear it maybe there’s a better way of doing this because they have been so used, they’re so conditioned to change at an enterprise organization. And enterprise organization has SaaS organization, that they don’t have the connection to the processes, it used to be three months ago, because you know, three months ago, and startup land, you know, feels like a lifetime for some of those individuals working it, you know, and so that I think those are kind of the key differences, you have to realize that there’s a lot more emotionality in a series a organization than there is in an enterprise SaaS company. At the same time, if you can gain trust, and you can position your solutions as smart and they see value in it. Change management is like that, right? So once you get past that emotional hurdle, they’ll implement it, and if it works, they’ll drive it whereas that’s always the hurdle from an implementation or an enablement perspective of around process at an enterprise which is the organization understands the strategy change. Now Good luck trying to implement that strategy change that’s going to be harder because there are just so many voices so many different styles to communicate to, whereas on the Series A side, the first time that a method brings in a big deal that seemed out of reach in the past, now everybody’s like, how do I use that method in order to be successful? And I like that aspect of it. I enjoy working as a person as an executive in organizations that are There are more in the startup space, I enjoy the startup space more because I find it to be more challenging to convince these people. But then once you do, everybody kind of points towards that Northstar, and then executes against it, which is super exciting and rewarding.

Pete Thornton 20:16
That’s very interesting. What I’m hearing is like series aid, the commitment is so high but in its like, it has pros and cons like a commitment to like an emotional commitment to the company, as well as recommending it to processes. I’ve worked in enterprises, which people are very, pretty aware of this, like, if you are in your organization every six months, for the last six years, like you’re like, Okay, so this is coming in. So these things are gonna swap like you’ve seen enough new things come in and change things for the better. But the implement—

Jason Reichl 20:44
And you’re not turning the dial from one to two, you’re, you’re, you know, micro-adjusting dials usually in the enterprise. Right? I think rev ops for the enterprise was hard to transition to because it was clicking from seven to 11. Right. And that that was a big thing. And I think that’s why go nimbly was so successful as a consultancy, working with these companies is because they actually needed help transforming, they didn’t know how to do it on their own. But most enterprise operations or CRO responsibilities are, are more dialing up or down by a few clicks, not not a significant transformational change.

Pete Thornton 21:20
Let me ask you about this because this is The SaaS(ramp) Podcast, you are at a SaaS company now, but you just came from a very successful services-based company, like do you have an opinion about where services versus SaaS makes sense because there are places where like, you can give the pure customization, like, this company is different than this company is different in this company, we’re hearing you we’re human beings, we’re taking in the data, we’re using this large, unscalable brain in our heads, but very human-centric.

Jason Reichl 21:48
Yeah, I totally understand what you’re saying. I come from a product management background, and I was a product for a unicorn company called a trade shift. And what I believe is that servicing can be turned into a product that is not bespoke. So go nimbly, when when I ran it, I worked very diligently to try to create products, not bespoke servicing, I don’t like bespoke for servicing. And I don’t think it’s just my Silicon Valley inside of me. I think what happens is customers get very different experiences, when they use consulting based on who’s on their team. And I always wanted that, who’s on your team to be the icing on the cake. And I wanted the loyalty and the ideas to be baked into the product. Right. And so my experience with consulting, and I’ve been a pure consultant before going nimbly, as well before I was ever in SaaS, is that you can only make as much money in consulting, as your time allows you to make in your brain allows you to make now obviously, there are people who do online courses and all that kind of stuff, which is, obviously it allows it, but I’m talking about pure solutioning. But if you’re able to build a product like we were where we looked at operational projects across different inflection points, and I would get that data and analyze it, I could see what projects were actually pushing an organization towards success. And which ones which I would call vanity projects, which are, you know, some head of marketing wants us to do X, Y, Z because they think they should do it not because it’s going to be beneficial to the revenue, and over time was able to build very specific ideas about what should happen at each stage. And that, I think, is how you productize that bespoke model. So yeah, very early on, it was completely bespoke. But over time, you were able to train a baseline thing, like every organization needs to implement X, Y, Z they need to do this thing, they need to have their system set up in this way, in order to take advantage of conversational marketing, on their website, whatever those things might be. There was a strategy tied to it. And as soon as you tie strategy to consulting, you can actually privatize servicing. And I would urge every SAS company to also think of their service team as a product. And I do believe that in these uncertain times, having a strong service component, as part of your core product is a huge value differentiate, and also necessary, when there’s so much change happening both because we might be entering into a recession and SaaS, but all secondarily it’s also happening because the buyer buyers changing. And so you really need that, that touch that a service team can provide, or an am team could provide to your customers in order to guarantee churn and an upsell. Right and so I really believe that, again, services are wildly neglected because It didn’t look good when you went to go raise an evaluation, if it wasn’t considered a part of your subscription price, my favorite thing to do is to figure out my servicing cost and incorporate it into my product cost. Thus, it’s part of my subscription model and how I have solved this problem or have worked on solving this problem in different organizations I’ve been in, which is just make it part of the product cost, because then you can really look at that. And if a customer needs a lot of servicing, in the beginning, you’re covered. And then over time, that just becomes pure, pure profit to the SaaS organization versus one-time fees, and all these other kinds of things, where we basically SaaS companies are saying, hey, my implementation team is a joke, right? That I mean, that’s something that they’re saying when they’re doing that, oh, that’s just a negotiation tactics that we can take it off with the implementation costs, or the servicing this, the bespoke servicing, or the white glove servicing, that’s just there. So we can mark it off. So you think you’re getting a discount? This goes back to one of the things I said earlier about authenticity is like, I believe that you should operate as a CRO, as a doctor, if you don’t believe that customers need your product, in order to be successful, you’re at the wrong organization. Right? That’s the first thing I believe. The second thing I believe is your job is to educate customers on why your product is valuable to them, and will solve their pains. And if they choose to walk away because of price or because of whatever, they will come back the same way that they would come back to a good doctor who gave them that opinion in the first place. And so I very much like being straightforward about what’s going to make the customer the most successful version that they could be. And I think that over time, that builds a culture of a value added culture across every department.

Pete Thornton 26:45
Yeah, yeah, I like that. And it enables you to kind of go strongly, like, I had to get me on products that I liked, because I knew I didn’t have a former teacher, I was a high school biology teacher, soccer coach, I did not have like the sales chops at some of these people did especially at the age that I transitioned. And then and so I came in, I was like, Hey, I don’t understand that. So I’m gonna have to tell the truth. Can you told me three true things that are excellent about this product? I will make 100 phone calls. That’s how it started because there’s no way to get around that often.

Jason Reichl 27:16
But I mean, I think this is your a perfect example. If you just take the soccer example, you know how to incrementally improve your game, and you know about how to coach craft. Thus, you were able to make a transition, that a lot of people, even if they went to school, and they are, say a great developer on a development team, if they are not focused on their craft and knowing how to coach themselves, they will not be able to make hard transitions between inflection points of an organization. And one question I commonly get. And you know, this is something that maybe I’ll talk about on my live show that I’m doing, which is wake up GTM Tuesdays and Thursdays at 9:35. This is a plug 9:35 PST time on LinkedIn. Tuesdays and Thursdays at 9:35 am for 25 minutes on LinkedIn.

Pete Thornton 28:06
Yeah, I’ll definitely be on.

Jason Reichl 28:07
But one of the things that I’m a big fan of is inflection point transitions, what kind of individuals are able to go from a Series A, to a series B, to a Series C, to sear in that same company? And it all comes down to? Can you coach yourself? Do you understand your craft? And are you committed to becoming better and changing as rapidly as the organization needs you to? And they really does come down to some fundamental things. And one of them being like your background that you just mentioned?

Pete Thornton 28:36
I would love to ask you about that like it because it’s because I’m watching it happen is really interesting with a company that’s ever that’s changing every six months. This is a second one I’ve been at it’s been exactly like that, except for just different motions. PLG versus top-down. So would you gave a really good synopsis of what series A looks and feels like. At The SaaS(ramp) Podcast, one of the things we’re trying to do is understand all the challenges between product adoption and validated go-to-market motion, like enterprise motion, like that can happen between many of these funding rounds that are kind of like marking the call an inflection point. Yep. And so like, Do you have something in mind for seed A, B, C, D? Is there something that like you have a mental model for that you could lay out?

Jason Reichl 29:20
Yeah. So series A is about going from bespoke, which is usually your first million dollars of revenue, your bespoke I mean, whatever worked, whatever size customers you could get in whatever industries are interested in your product, even if you are targeting a specific industry. And when you then get to that million-dollar mark, you raise your Series A, and when you raise your series A it’s about proving that there is a repeatable go-to-market process. And repeatable doesn’t mean sometimes getting to a certain dollar amount, although a lot of companies try to get to, you know, a three to 2.5 to $5 million mark before they raise their series B. But it’s about if I how much dollars do I need to put in to create a pipeline? How many dollars do I need to put in to convert to a win? How many dollars do I need to put in, in order to have a customer implement it because you’re probably not gonna have many cohorts that can tell you what your churn rate is. So, CES, usually, in a series, a company, a ragtag group of people, right? And there, they are handling different situations all the time because you haven’t really solidified on what does a successful customer look like? Because you’re just starting to deal with your customers. But what you have proven by the time you get to series A is how do people want to buy this product? Or maybe you’re figuring that out? And so Series A, it’s all about that repeatable, marketing, and really heavy marketing, repeatable sales process. Series B, to me, is all about how do we create a flywheel in marketing in order to meet the demands of growth that are required of a high-velocity startup. And when you move into that realm.

Pete Thornton 31:03
Is the requirement coming from like the funding, like, hey, here is $30 million $50 million. But number is the double headcount, double revenue, kind of thing?

Jason Reichl 31:14
I mean, I think that people wish that the boards were as clear as that boards are not, you know, one of the things I do is work very closely with VC. So I got a firsthand understanding of what VCs are looking at, for at different inflection points. But what you actually find is not necessarily what it takes to raise money, because VCs will give you money for a larger percentage of their company, but what’s actually going to result in a higher valuation for you, which then protects your ownership of the company, right, and I’m talking specifically to CEOs right now, right? Who are our founders of organizations, which is you want to protect your equity, the way you protect your equity is get the best valuation, there are certain recipes that you should focus on at each of those stages, in order to get the best valuation, regardless of what your board is asking you to do. Like your board might come in and a Series A company and say, Hey, we have to do PLG. Because PLG is hot, and it’s a good idea. 100% Good idea, you probably can’t do PLG, because you don’t have the user base, that would be a huge change in your revenue structure, it’d be a lot of development, a lot of focus in order to get maybe a five to 15% upsell from your product, and you already have to be in a trial mode. So that basically excludes series A enterprise software because Series A enterprise software very rarely can be sold trial to conversion because the product is usually not mature enough to sell it at that, at that phase. So all of these kinds of recipes exist for what I would call is the most optimal outcome, which is keeping your equity and really dialing up what the valuation will be at each stage. Now, obviously, revenue speaks a lot. But revenue without a process leads to a distrust and a lack of confidence in your startup by your board members or other VCs that you might want to bring in. So I found that by having your operational processes tied down, and showing that you know exactly how you’re getting the gains that you’re getting, it is it adds a lot of trust, to those kinds of conversations to your board conversations to, to the VCs that you’re trying to, to speak to. So that’s my advice is like, you need to be focused on those things. That is, to me a CEOs job to be focused on those things. What your team needs to be focused on is the buyer journey, how are we going to improve the buyer journey, but how you make that decision on what we’re focused on what we’re prioritizing over one thing, because let’s say two, you have two gaps in your buyer journey. One is $3, and the other one’s $3? Which one are you going to do, you’re going to do the one that helps your valuation? The best? So that’s the job of the CEO to sort of manage and understand, do we fix this in product? Or do we fix this and servicing? Or do we fix this in marketing? Or do we fix this where and those kinds of decisions are leadership decisions? And those are those decisions that I enjoy? Making? As a CRO right, those are the sorts of strategies decisions that I enjoy making? How are you going to move to where we need to be to protect our valuation and make sure that the people who are working in the startup, which is always my first concern, people working in the startup get the best outcome because they’re doing the work? I think VCs do a very beautiful thing by giving SaaS companies money, but it’s, it’s business, right? The people that are working in the startup, it’s personal, even if they want huge outcomes for themselves, because they would like to be rich, or they would like to have, you know, the TechCrunch write an article about their company and know that they were one of the first 50 employees. Really, it’s personal for them because they’re working in the trenches of that organization. And for VCs, it’s not. And so I always think about the PERT the person I want to protect is the person who’s emotionally invested in the organization.

Pete Thornton 34:59
Yeah, this is interesting. This is like this. By the way, I have asked one question that’s on a little list of questions, you know, and we’ve just like had a good. What I’ve enjoyed is like, we knew this would happen, kindred spirits. So you are in a small organization, you’ve had your own organization. And you’ve worked with very large organizations all within this, like SaaS, hypergrowth type space. So I have found that, like certain guests who have experienced large and small, one thing comes to mind, in particular, is Sarika guard. She’s a cash flow. That’s a series a company. And she had previously worked at SAP. So she’s like, I saw this, we’re here now. And like this, this chasm in between.

Jason Reichl 35:39
Her and I work together at Tradeshift increment.

Pete Thornton 35:43
Oh, no kidding.

Jason Reichl 35:44
Yeah. So she was brought in on the marketing end. And I was the director of product around the same time. So I know her well.

Pete Thornton 35:54
Okay, awesome. This is probably LinkedIn is probably like doing this thing. Right? Where we connected in it just knows that we both knew the same person. I bet. Yeah. Good job, LinkedIn.

Jason Reichl 36:02
But yeah, 100%. That’s one of the things she was brought in at when she was brought in for Tradeshift is she had that experience at a large organization, and they were in hypergrowth, and they wanted to, you know, set themselves up successfully to reach those outcomes. Now, I’m not a big believer that the thing you should do for your startup is go, Are we allowed to curse on this, I don’t think sometimes that your shit should go out there and a star mingle, I won’t say the other word, but star mingle with everyone that’s in another organization, because, you know, some people not serica. But some people come in from big organizations, and they bring their bad habits to, uh, you know, you hear this all the time, if you hang out with SaaS founders, they’re like, I hired this guy, he doesn’t want to make the phone calls. Yeah, cuz you hired an enterprise AE from a, you know, $100 million company. And they’re not used to that. And they didn’t expect that. And you weren’t clear about that when they came in that they were going to take that role, because half of them would say no, and the other half would be like, That’s exactly what I’m looking for. So I think that’s a, you know, a problem when we start mingle, which is, you know, I want to be like x company. Well, a lot of times in SaaS, and this is true with a lot of organizations I’ve consulted with, you’re actually trying to disrupt the very companies that you’re hiring people from. So maybe you should rethink that hiring strategy as your only primary strategy. But I do believe there is a group of frustrated people at companies that have been successful, who are looking to fix the errors that their successful companies made, because they actually believe that the company could even be more successful or have moved faster. And those are the people that you want to hire, you want to hire those people who have had that experience. But who were not satisfied by that experience. I’m a big believer in hiring people who were not satisfied with their previous jobs. If you hire someone who’s like every job I’ve ever had is bliss, and they can’t talk to how they would have changed those organizations. To me, they don’t have the entrepreneurial experience to work at a seed series A or Series B organization, because those people need to be bred to be unsatisfied. And I think that’s a core thing that I don’t think you can teach. But that’s the thing I look for in the interview process is which is, and this is the thing that also people are coached to not talk about, which is you shouldn’t talk about the organization’s you worked at in the past. But I’m not asking you to, to speak ill of the organization. I’m not asking you how could that organization moved faster? And when you ask some people that who have worked at a company, like Twilio as an example, they have no answer for it, because they could barely hold on to how fast Twilio was growing. And those are the people you don’t want to bring into your startup. And so that’s advice around hiring that I would recommend to most people.

Pete Thornton 38:31
Okay, interesting. So you’re looking for ownership. Ultimately, that seems to result in ownership, like what was presented, that means they thought about it, because they wanted to own it, whether they could or couldn’t, and maybe they couldn’t. And maybe that’s why the fit makes sense. There are a lot of rabbit holes over here. I would love to continue, but we blew past it and I still want to come back. We talked about just before: you’re going to do a new thing, and then what are you doing, and then why? Give a little backstory on what this is.

Jason Reichl 39:02
Sure. So I’m doing something called Wake Up GTM. It’s my version of the morning Zoo Crew, LinkedIn kind of thing. So I’m gonna get a cup of coffee. I’m going to sit down and in answer people’s questions either live or via a GTM hotline that I’ve been running for two years. So when I started doing podcasts and lectures and things like that people would have questions. I would be in the back answering the questions. But I felt like I wanted to do more. So I started giving a phone number at the end of different podcasts I was on and people started texting me at that phone number. And when I was Thursday night, after dinner, I’m sitting there my kids in bed, I would start having corresponds with these people as I like to think of as a pen to pen pal situation. And over time, I’ve amassed around 300 of these questions that are still applicable and need to be answered in the most broad strokes kind of like this rapid-fire thing that you did, which led us to all these interesting counterpoints. So what I decided to do is, hey, let’s do a morning show two days a week? And answer those questions. And if I don’t know the answers, let’s let me bring in a guest who does so instead of a podcast. And what I really appreciate about this is yeah, we could have talked about where I come from in my career and all that, which is important, people need to do that. But more important, let’s just get into the, let’s just get, let’s just wake up, let’s just focus on what’s important. And that, and that is the core concept of, of the show. And going into a series a company, I kind of took a backseat for the last six months and giving back to the community, which I very much value because they’ve taught me everything I know. And I have a lot to teach the younger generation. And so I decided that this would be a good opportunity now that I kind of have my sea legs, that TrustLayer to move back into helping people and answering questions. I love podcasts. And but what I’ve really been into lately, is YouTube, a quick answer things. So I love watching the things that Y Combinator have put out, which are like two minutes, three minutes, little chunks that are interesting, that get your brain going and thinking throughout the day. And I know, one of my philosophies we talked about worth like integration is I actually do, I’ve done and helped other entrepreneurs with something that I called the eighth-day methodology, which is how do we get better without adding an extra day to our week, we only have seven days in the week. We’re all busy all seven days. So how do you actually work on your craft in your existing circumstance? And for me, it is on Tuesdays and Thursdays, I sit down and ask myself a question. And I usually write an essay out about what that answer is. And that gets my brain moving so fast, and so awake, that then I’m seeing all of the opportunities in my work life and other places to work on that craft. And so I want to bring that to people in the form of this, you know, 25-minute check-in where we make some jokes, and we answer some questions. But hopefully it’s an ideation starter for what you’re looking for and what you want to work on.

Pete Thornton 42:06
Rad. Okay, that is super cool. Yeah, you can hit it in LinkedIn, it pulls it into your calendar, if you’re integrated and stuff like that, and I am free for 20 of the 25 minutes. I happen to notice in my calendar every great so like I will be Yeah, it’s fantastic. Yeah. Thanks, Jason. This has been so so good. We’re super far past, it’s got so many good nuggets, and I can’t wait to to do it again probably in six months when you’re at a TrustLayer and it’s yet a different company again. Then we can talk about what’s happening with the flywheel and Series B at that point or something like that.

Jason Reichl 42:38
I think we can change your name from Pete Podcast to Pete Good Guy Thorton.

Pete Thornton 42:46
Listen, give me a good guy Thornton. Give me some of those sweet emojis like you have in your LinkedIn profile like your banner back there and what didn’t is the best-looking thing I’ve ever seen. Yeah, it’s Thank you. Yeah, it’s a kind of a fascinating new but I never see it. I don’t see it out there very much. Like we’re a little serious out here maybe.

Jason Reichl 43:01
Yeah, a little serious. We don’t need to be that serious. This is We are lucky to have the jobs. We have no time in human history. Has it been more enjoyable to work than it is right now. So count your lucky stars.

Pete Thornton 43:13
Completely. Yeah. And from your guest bedroom or wherever it is you find yourself.

Jason Reichl 43:19
All right, man. Thank you.