Ep. 284: Travis Bryant is Partner for Founder Experience @ Redpoint Ventures, the venture fund with a portfolio including the likes of Stripe, Netflix, Zuora, Hashicorp, and Juniper Networks just to name a few. As for Travis, prior to joining Redpoint, Travis was head of Customer Growth at Front, after spending 5 years building the global Sales organization at Optimizely, the world’s most popular experimentation platform. During his time at Optimizely, the company grew from $7 to >$90M in ARR and from 40 to 400 people. Before Optimizely, Travis spent 6 years at Salesforce in a number of sales roles including building the first Platform Sales team.

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In Today’s Episode We Discuss:

  • How Travis made his way into the world of venture as the first ever Partner for founder experience at Redpoint? What were the 2 biggest lessons Travis took from Salesforce? How transformational is the 12 quarter year for Salesforce?
  • Why does Travis believe we need to abolish the title of CRO? Why does it suggest misalignment between customer and vendor from Day 1? What aspects of CRO’s roles is Travis in favor of? What elements is he not in favor of? What does Travis advise founders when it comes to uniting customer facing teams?
  • Why does Travis believe that SaaS has upended the economic model but not the engagement model? How does the engagement model with customer need to shift? What does this do to the structure of the conventional funnel?
  • Why does Travis believe net retention must always be the guiding North Star? How does Travis think about the different steps to customer qualification today and what makes the best SDRs? What does Travis advise founders when it comes to churn analysis? What questions must you ask? What metrics must you look for?


Ep. 285: Hear about Adyen’s journey from a Dutch payments startup to a global public company with more than 15 offices around the world working with large global companies like Facebook, Spotify, Uber and Microsoft. CCO Roelant Prins shares lessons from the company’s own global growth path and will be giving practical tips for companies who are thinking about expanding their business globally. Roelant is joined by Felicis Ventures Founder, Aydin Senkut, who shares the commonalities he sees in successful companies…starting with culture.

SaaStr’s Founder’s Favorites Series features one of SaaStr Annual’s best of the best sessions that you might have missed.

This podcast is an excerpt from Aydin and Roelant’s session at SaaStr Annual 2019.


If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin
Harry Stebbings
Travis Bryant
Aydin Senkut
Roelant Prins

Below, we’ve shared the transcript of Harry’s interview with Travis


Harry Stebbings: This is the official SaaStr podcast with me, Harry Stebbings, and if you’d like to see how the episodes are made here, we will be welcoming you behind the scenes here this weekend on Instagram at Hstebbings1996 with two Bs. It would be awesome to see you there, but to our episode today. And it’s quite rare really, that you’re able to say no one in the world before me has had this job title, but this is a line that this guest today can most definitely own. So with that I’m thrilled to welcome Travis Brian. Partner for Founder Experience at Redpoint Ventures, the venture firm with a portfolio including the likes of Stripe, Netflix, Zuora, HashiCorp, and Juniper Networks, just to name a few. As for Travis, prior to joining Redpoint, he was head of customer growth at Front after spending five years building the global sales organization at Optimizely, the world’s most popular experimentation platform.

Harry Stebbings: During his time at Optimizely, the company grew from seven to $90 million in ARR and from 40 to 400 people. Before Optimizely, Travis spent six years at Salesforce in a number of sales roles, including building the first platform sales team. I do also want to say a huge thank you to Alison at Gainsight for the intro to Travis today. I really do so appreciate that, Alison.

Harry Stebbings: However, I’m now super excited to welcome the first ever partner for founder experience, Travis Bryant at Redpoint Ventures.

Harry Stebbings: Travis, it is absolutely fantastic to have you on the show. I’ve heard so many good things, both from Tom Tunguz and from Scott and so huge thank you for joining me today, Travis.

Travis Bryant: Harry, it’s an honor and a privilege.

Harry Stebbings: That’s far to kind of you, but I do want to start today with a little bit about you. So tell me, Travis, how did you make your way into, first the wonderful world of SaaS, but then also I think most fascinating me as for me, definitely, the first ever partner for founder experience at Redpoint. How did that come about?

Travis Bryant: Yeah, I have a bit of an odd path for sure. I started my career as an Oracle DBA and a failed Java developer and realized pretty quickly that I wasn’t great at that. But I could explain what technology did and vary that explanation to different people. So that ends up being a very useful skill for customer facing roles.

Travis Bryant: So I was in services at a software company and then had this pivot point to go either into product management or into sales and sales engineering. And that was really the fork in the road for me. I had the good fortune, my first SaaS experience was at the Mothership Salesforce in 2006, prior to even the word cloud being thrown around. And I had a tastic experience there for about seven years before running a marketing tech sales team at Optimizely for five years. And then, you know, even stranger to end up in venture. But through knowing Tom and his local celebrity, reading and passing around his blog posts, had the chance to meet with him directly, built a relationship and found myself stepping into a brand new opportunity, which as far as I can tell on LinkedIn, no one has the title. So I’m keen to define it and build out.

Harry Stebbings: I did that research too. And you were the only one I could find, but I do want to ask, because you mentioned that your time at Salesforce first, so let’s start with that. Were there any kind of hacks that you learned that really worked at Salesforce that you think are transferable to the industry and maybe a big takeaways for you?

Travis Bryant: Yeah, well I ended up in the, what then was called the corporate sales organization. Which was that pioneering inside sales motion driving a lot through online and through WebEx at the time. And it was a very high velocity model. And one of the mantras that we had was the 12 quarter year. It really was, we closed every month. We made every month. There was this cadence driven by Frank van Veenendaal and Brian Millam that you were always on.

Travis Bryant: And that pace can be, of course, a bit maddening, but in SaaS that doesn’t matter because how you recognize the revenue, it does really make a difference to push things forward and to make every month. So I think that was one lesson ingrained at a very early age. And the other was just even such a simple trick that’s now become standard around fiscal year close. Shifting that from December to January was very subtle but meaningful because we were able to close deals with companies that their budgets were ending in December and so they needed to spend them. And so we would always get a nice pop at the end of the calendar year, but we would also get a nice pop at the beginning of the next calendar year because new budgets would open up as well as it would be the end of our fiscal year. And so we were incented to have a strong finish. And even just that shift drove a lot of behavior change both with customers and internally with the teams.

Harry Stebbings: Can I ask you in terms of like the sales mentality with the 12 quarter year, did you really see a change in mentality in the reps themselves, given the urgency?

Travis Bryant: Oh yeah. I mean there were even certainly… At different under smaller segments within corporate sales they would actually have their accelerators and targets set monthly. In the higher segments you would have an annual target. But the way that we ran the forecast, the way that we spoke about metrics and performance, there were all of these sorts of subtle behavioral accountability changes that drove that sort of intensity. If you could take a deal off the table within the month, you didn’t wait for the end of the quarter and so it was trying to smooth out that inevitable hockey-stick.

Harry Stebbings: I do want to move on more to the present day because you mentioned that being the only one with the title founder experience. So without sounding rude, what the heck is partner for founder experience, Travis?

Travis Bryant: Of course, well the genesis of it was a conversation with Tom about the innovations that are happening in Venture around platform. This idea that we should deploy more capabilities to help companies once they come into the portfolio, fulfill their ambitions. And so that is most evidenced by what Andreessen Horowitz does with talent and PR and communications, business development and corporate development, and that is a huge team and apparatus now at a fund like that. But it really has shaken up the industry to say, “Well, what is our response to that and how do we remain competitive?”

Travis Bryant: So that was the genesis of the conversation with Tom. But as I looked at, and I did a research project before joining, I was a part time EIR at the firm and I said, “Well, I don’t really know what platform means.” It’s one of the most overused terms in our industry. Let me go and figure out what I think the strategy could be for Redpoint and if that makes sense, then let’s talk about how to work together.

Travis Bryant: So I went out and I talked to a bunch of founders. I talked to a bunch of people doing platform at different firms to try to figure out what made sense for Redpoint and the insight that I had was this is really a customer process. All of these muscles that I had built from my time running customer facing teams in B2B SaaS, you can apply that to the world of Venture. And if you just swap the word founder for customer, think about customer success and the ideal customer profile and all of these now have become best practices. We can apply that to how we think about that entire life cycle.

Travis Bryant: So not just what happens post investment, but everything from the first time they touch the brand to them considering to raise money to us considering to invest in them, to us competing with other firms. All of those moments are opportunities to optimize and drive some discipline against. And so founder experience just means end to end, all of those touch points. How do we create value and make sure that we respect their time, we’re efficient and effective in how we build that relationship.

Harry Stebbings: Can I ask, in terms of like being super effective in your role, transparency must be key because you must be essentially kind of CC’d on all emails. Like all first emails or follow up emails or rejection emails. Almost like in the meeting with the pitch meeting itself. How does the transparency element work, because you obviously have to ensure that the experience is the best that it can be, but then you also have to almost be in the room, don’t you for everything?

Travis Bryant: Well, yeah, there’s some element of sampling, with any sort of role, you can’t be everywhere at once. But if you can dip in and you get enough data to form conclusions, then that’s one way to hold accountability to the process. There’s technology as well. One of the things that I’m realizing is to enable this sort of discipline, you need really strong CRM and other tools to help you learn from the process and improve it.

Travis Bryant: And so for example, one of the tools that we have in the portfolio is a company called Chorus and they do that sort of call recording where there’s AI to interpret what happened in the meeting. And I’m experimenting with deploying that in our pipeline review meetings so that we can record those and learn from them based on what we talk about and how we approach an investment with a potential company.

Harry Stebbings: I love Chorus and I think Roy is amazing by the way, so I’m super pleased to hear that. I do want to dive into the meat of the show cause you said that about kind of the customer element and I want to transition slightly to the world of SaaS. Because when we chatted before you said something very interesting. You said, “One of my grassroots campaigns is to kill the title of CRO, although I’m vehemently in favor of the scope of the role.” Quote finish. So let’s break that apart. I love that as a title. But why do we need to remove the title of CRO, Travis?

Travis Bryant: I have to be really careful with this Harry, because of course I have a number of friends and former colleagues who have the role, and I don’t want to be too controversial here or create enemies. Here’s the thing, this is from my own perspective. I couldn’t imagine having that title and going to meet a customer and introducing myself that title because the underlying messages, “What I care about is your wallet, not actually you finding success from the products that I’m offering to you.” And so it just seems like a bizarre way to state a relationship.

Travis Bryant: Focusing on the revenue part of it is the lagging indicator of what actually the customer facing teams really should be obsessive over, which is the ultimate success that that customer has from using the product. So it just, it’s bizarre that, to me, that’s become conventional wisdom that the title for that individual that is unifying those customer facing teams, which I am a huge supporter of, especially in SaaS, is in fact called a revenue officer. And I think there are other monikers that can unite that team over what the focus should be, which is really around the success of that customer.

Harry Stebbings: Okay. You said that about the other morning cause I’m super intrigued because you know I hear a lot of different functional leaders saying, you know, we’re driven by MQLs and other teams driven by SQLs and other teams are driven by pure revenue and it’s very fragmented in terms of targets. What monikers would you advise in terms of uniting customer facing teams?

Travis Bryant: Well you can tell from my current title, I’m in love with made up fancy titles. There’s some experimentation here. I liked the idea of Head of Customer Growth, something that where customers should be in the title because again, that’s the sun that the planets revolve around. But everyone in that organization should be thinking about how they grow that relationship with the customer. It doesn’t matter if you’re in marketing, sales, customer success, services, everyone is thinking about how we achieve that manifest destiny with the customer.

Travis Bryant: It’s everywhere that we can help them, they know about that, and that we are doing that. So customer growth, chief customer officer, even customer success, that’s been certainly used for a very specific role inside the SaaS company. But that is really the thing that everyone should be optimizing for.

Travis Bryant: And just to your point about metrics, that is where there is some danger of each individual team being siloed is if they’re missing the larger picture. The reason that everyone is involved is actually net retention. That is the most important North star metric that drives the success of the SaaS company. And there we may break that into smaller lower latency metrics for specific teams because of their specialization. But if they lose the picture that we’re all actually trying to achieve the same top level metric and then this is the role that my metric plays its part in doing so. That’s where you get a lot of those accidents happening intersections to quote one of your previous guests.

Harry Stebbings: Can I ask in terms of net retention, do you think that should be the core North star goal then that drives everyone not–A lot of people say a number tied directly to revenue should be the north star goal for everyone, but you actually think the single unit of net retention should be?

Travis Bryant: I do personally because it’s the ultimate measure of the health of those relationships. I guess there certainly is a component of if you don’t add enough new logos and new business then you don’t have enough of a substrate to net retend. I think I made up my own word there we’ll have to check with Webster’s on that.

Harry Stebbings: You’ve got founder experience, I’ll totally go with retend, so go with it.

Travis Bryant: The measure of world-class SaaS organizations is that the companies that they acquire are expanding greatly over time. You’re keeping those customers that you’ve acquired and they’re finding value from the product such that they are not only just staying with you, but they’re finding new use cases, finding new teams and departments and you growing that relationship over time. And then I think if you look at the companies that are in this generation, SaaS companies that are just really, really impressive, thinking about Zoom and Slack as two examples, when you look at their S1, what they’re really highlighting is how great their net retention is. Because that is a very clear measure of a subscription model health.

Harry Stebbings: I totally get you and agree with you. Can I ask you in terms of the net retention itself when you do have churn, how do you think about effective post-mortem analyses? I’m always wondering this because sometimes customers maybe just aren’t meant for your product. They are the wrong target segment, they didn’t have budget and it could not be your product. So I’m really intrigued. How do you think about effective post-mortem analysis?

Travis Bryant: Personally, the concept of NPS, to me, is very powerful, not because of the score, and this is where there’s some confusion given that S could be score or system. But what’s more powerful about NPS as a program is the system and the system is the root cause analysis and follow up. So when we have some sort of adverse financial event, we have a downgrade or a complete logo churn. It’s the five why’s to keep digging with that customer, whether it’s through objective data analysis, looking at their product activity, or direct interviewing of the key players that were within the customer.

Travis Bryant: Getting down to that root of why did this not work for you? And to your point, I do think that there is oftentimes a failure in qualification in the presales process. By nature a lot of sales individuals are optimistic and positive and they’re going to look for the reasons to get someone to sign rather than not. But this is another element of SaaS where the second best thing that can happen is losing early and so the rigorous qualification of “Do you fit within our ideal customer profile?” During that dating phase while they signed up for the trial, while we’ve done first discovery, it’s okay to say, “Well, you don’t match this sort of customers that we think we can have a longstanding relationship with.”

Travis Bryant: And it does us no good. If you sign up for the product and you don’t renew that first contract. You actually go out of business faster because most SaaS companies payback periods are longer than a year. So it behooves us both to spend that time upfront doing that qualification and what should be in that qualification can be a result of what you learned from those churns and downgrades to further refine your ideal customer profile.

Harry Stebbings: You said there SDR, you said discovery, you said qualification. And naturally I get super excited when I think of any SaaS funnel. One of the many reasons I’m still single. But I have to say you do have such fun doing a podcast. But tell me, I want to ask about it, this, kind of the funnel itself, because you said before it has upended the economic relationship, but it hasn’t changed the engagement model, when we spoke about the rise of SaaS, so I’m interested in what did you mean by this? Upending of economic relationship but not changing the engagement model.

Travis Bryant: Okay, so this is, I think very much I learned during the early days of Salesforce and it’s become legend now of the title is Dr. Doom was the head of renewals who came and presented to it an exec offsite and talked about if we didn’t shore up customer success, adoption and usage and value realization, then no amount of new business was going to fill the leaky bucket. And so the message from Marc on down, which was–not just this sounds good on the posters in the office, but really the livelihood of the company was dependent on it–nothing is more important than the success of every customer.

Travis Bryant: Because in SaaS, the value doesn’t come from the new business deal. It comes from the renewal and expansion and that’s what makes the economics work. So that’s changed of course, clearly with a subscription business model. But what in my mind hasn’t changed as much is we still think in this serial nature of the funnel. A suspect becomes a lead, a lead becomes an opportunity, an opportunity becomes a customer. And each department is participating in that component of the life cycle.

Travis Bryant: Well, that’s not really the nature of a relationship with an entity anymore because the moment that a company signs up for a trial, whether they’re paying you or not, you have to treat them like a customer. Because if they had a bad experience, they’re going to tell others about it either by word of mouth or Twitter or G2 Crowd. And so you’ve got to treat them as if they are paying you, even from those early days. And conversely, every customer that has signed up and is already paying for the product isn’t probably paying for everything that they could. And so they are simultaneously a prospect.

Travis Bryant: And that means you can’t think of it as a funnel. And one of the metaphors… I have a ton of energy for what HubSpot is doing, they call it a flywheel. And even just that shift in the visual metaphor changes how they think about investments. Because what they’re looking for is where to remove friction to get that customer flywheel turning as fast as it can. And it changes their perspective on, “Well, should we invest in more SDRs to improve this conversion rate from MQL to SQL,” versus “What we actually need to do is make more investments inside the product to guide people in the trial because that removes the friction for them getting to the first winning campaign to launch at HubSpot.” Whatever that might be.

Harry Stebbings: Can I dive in and I’ll say two things and sorry if just kind of firing both at you but one is like how important do you think time to value is today, first? Yeah, let’s start with that first before I blow the second one. So how important is time to value?

Travis Bryant: I think it’s absolutely critical. And one of the things I’m experiencing early in Venture here is speed matters. Even in just how you get a term sheet to someone, and I know you’ve talked about this many times about preemptive rounds and how that’s working. Speed is a huge quality. I’ve seen that also in SaaS. So one of the realizations that we had at Optimizely with AB testing is you want to get people to run an experiment as quickly as possible. And so even how we did a demo and pulled that narrative story was get to the start button as quickly as possible because that’s the magic moment. So optimizing for that first magic moment in the trial, in an onboarding process, it sets the hook so that you can then build a deeper relationship. I don’t know if there’s any more important initiative, frankly.

Harry Stebbings: Can I ask, when you look at organizations today, obviously you meet a lot of SaaS companies and work with the existing RedPoint companies, but when you work with them and when you meet new companies, do you find there’s common points where friction or frictional debt tends to build up and where you think there kind of really needs to be a relief as such?

Travis Bryant: Well, one emerging theme–and especially with the new model of product led growth where you see what Slack has been able to do and what Zoom, I’ll just keep referring to them as these luminaries–is applying a business model in absence of understanding who your ideal customer is. And there’s a fascination with “Let’s let the robots do the selling.” Meaning if we could just get the product to do everything, we don’t need salespeople, we don’t need implementation and onboarding people.

Travis Bryant: But if that’s done in absence of really understanding who the target customer is, there’s a lot of dangerous misalignments of strategy. And so here’s what I mean. If for example, your product is the re-engineering of a business process inside of a company, let’s say how tickets are handled or how a product management process works. What you’re talking about is a human change management exercise and I don’t think any amount of guided tours inside the product or chatbots that pop up like Microsoft Clippy and say, “Oh, click on this feature because you’ll get value from it.”

Travis Bryant: I don’t think any amount of that will really help them adopt the service. There needs to be a human services or customer success team who is doing that hand holding to re-engineer a business process. And so just being true to what is the problem that our product solves and who are the companies and more importantly the people that we’re solving it for. And let that drive then your go to market strategy rather than just assuming that because companies like Slack and Intercom and Zoom and others have product like growth that we can have that too.

Harry Stebbings: And speaking of the people that you’re solving for, if we apply that internally to the team that’s helping those people solve it, do you think that anything that we can do in terms of org structure to really increase it and enhance this engagement model and bring it to the forefront?

Travis Bryant: Yeah, there’s of course an opportunity, or I should say a necessity for specialization. You can’t have one person be the deep technical expert that engages with the chief information security officer to talk about compliance as well as then is able to come up with the economic model that ends up in the quote as well as then is the customer care professional that’s onboarding and monitoring for adoption. You need specialization.

Travis Bryant: And so I don’t have arguments with specializing marketing and sales and customer success per se. But the alignment of that journey that everyone understands the larger context in which they play and why their specialization is a particular set of behaviors and metrics. They need to see the larger picture of how those behaviors and metrics are linked to that North star roadmap, as it were. And I think an area where there is the opportunity to drive more of that is shared metrics.

Travis Bryant: So there’s this big debate around–in SaaS around should we have new business only AEs and then so these hunters and then farmers that focus on the expansion business and then we have CSMs that focus on churn prevention. And I don’t think that there is a clear gold tablet of what that model should be. There is definitely a first principles approach that needs to be done there again, back to ideal customer profile and product.

Travis Bryant: Having said that, I think the idea of shared incentives and shared metrics can drive more collaborative behavior and so taking an AE who’s thinking about growth, taking a CSM as thinking about a usage and value realization and giving them both a shared expansion target helps drive that at its perfect, this symphony where the CSM has gone native and they’ve earned the trust to see where there is opportunities for expansion. And they can feed that opportunity back to their AE partner to drive that expansion evaluation and they both get to win if they have that shared metric of expansion is just an example where not necessarily in the org structure but in the shared accountability to metrics you can get more collaborative behavior.

Harry Stebbings: You mentioned the specialization there first before the sharing. I am really interested because I had Ben Braverman, a CRO at Flexport on the show recently and he said that actually it’s specialization is dangerous for the customer experience because at the end of the day the person who ingratiates you build the relationship within the sales process, you want to have support and work with you ongoing. I’m interested how do you think about that as an alternative to specialization and as a pushback. Do you think that’s essentially right and the specialization and segmented customer functions actually deteriorates the customer relationship?

Travis Bryant: I do. It’s a partial, yes with Ben. It’s all a question of where you draw the specialization line. Because there are side effects to anywhere you draw that. And let me give you a very real example. So as I said earlier, I don’t think it’s possible for a account executive whose skillset is driving decisions yes or no in a software evaluation as quickly as possible. I don’t think they can also be the deep technical expert in all the nooks and crannies of the product nor in the how do you map a business process and people to implement that product. I think that’s very hard for an individual to be able to do all of that.

Travis Bryant: And so we need to draw some lines there in specialization of skill. But where I would agree with Ben is in what is the impact to the customer. And because what you see in sometimes in specialization is as I said earlier, this new business AE who’s working on the first transaction. And then they flip it over the fence to a expansion AE or account manager to grow that relationship.

Travis Bryant: That feels like a strange specialization to me because that first account executive has built trust, they have understood the context of that organization and frankly the incentive for them, the big deal is typically not the first deal. It’s the fifth and eighth and 10th deals as you continue to earn trust and deliver to that customer.

Travis Bryant: So that feels like a strange specialization where it’s not customer friendly. And that to me is the guiding principle of how you should define your org structure and those behaviors is what creates the most seamless customer experience where you’re bringing the right expertise to bear and it’s going to be nigh impossible to have it in one person. How do you split that but create a coherent relationship so that every new person that meets the customer isn’t asking the same questions, which is of course very frustrating for them.

Harry Stebbings: Totally with you. I guess my question there is how do you think about… Actually had a brilliant guest on the show that said recently accidents happen at intersections and so when it comes to removing friction or smoothing the transition from function to function, what advice would you give on minimizing this friction, but what have you found elements that work and elements that maybe don’t work?

Travis Bryant: This to me very much is a data and process or framework exercise. One of the hacks that we did at Optimizely, though we had different departments for marketing, sales, customer success. The operations and strategy team was called customer operations. And we had a tools and systems group, an enablement group, and a data or analysis group, but that’s where the rubber really met the road, was, for example, if we had had a tools person in marketing just administrating Marketo and a tools person in sales just administering Salesforce then has one in success just administering Zendesk.

Travis Bryant: The thinking about that entire customer architecture and how the data flows from Marketo to Salesforce to Zendesk would have likely been very disjointed. Same thing with analyzing the pipeline. If you had a marketing operations person just looking at lead flow and MQLs and where they were doing that analysis was different from where the sales ops person was looking at SQLs and pipeline and forecast.

Travis Bryant: There just ends up being so much time wasted on trying to get to the same canonical. And so I think that this is really well done when you have a set of principles around data and framework and process that there’s a lot of discipline to. So irrespective of where that individual is specializing, when they step in, the first time that they talked to the customer, they have all the context of everyone else who has spoken with them because you have great CRM and you have great training to understand what those predecessors have done in their skill set with the customer and how you pick up where they left off.

Harry Stebbings: You mentioned the word discipline there, Travis. Now this is a round that requires a huge amount of discipline. I’m going to move into the 60 seconds SaaStr. So essentially I say a short statement and you hit me with your immediate thoughts. Are you ready to rock and roll?

Harry Stebbings: What motto or quote do you most frequently revert back to?

Travis Bryant: I have a couple. I’m going to pay an homage to your countryman Winston Churchill, I have nothing to offer, but blood, sweat, toil, and tears. That’s one of my favorites. And maybe a mantra is simple things done masterfully.

Harry Stebbings: What’s the most challenging element of your role with Redpoint today?

Travis Bryant: Well, for me it’s the shift from an operator role where the area was very well defined. When you’re a head of sales, your week is pretty much mapped out. You have a forecast call, your pipeline review, your big deal reviews, you have interviews. And here this is very self directed. This is a product manager role, so what initiatives we’re going to run, programs to drive value for founder experience that isn’t defined and so I’m transitioning that mentality there.

Harry Stebbings: How should strong operators coming out of larger organizations assess which startup to join?

Travis Bryant: A bit cliche maybe, but the matrix that I always used was the combo of product, market, and people. For me as a sales professional, it always started with I got to have genuine enthusiasm for the product. Market is there’s enough people who care about this that we can become a large impactful company. And the day to day satisfaction in any role comes from the people that you’re surrounded with. You would do a lot of really crappy jobs with people that you loved and learned from and had fun with. So product, market, and people was my matrix.

Harry Stebbings: SMB to enterprise or vice versa. What advice do you give to startups?

Travis Bryant: This is back to what we were talking about earlier, this is first principle thinking, being really true to what product value you’ve created and who does that apply to? Being very honest about that ideal customer profile, that will guide you to whether you start with a high velocity SMB model or an enterprise model or both if you want to try to pull off that magic trick.

Harry Stebbings: Super hard one here, but what are your biggest strengths and weaknesses? 30 seconds on each.

Travis Bryant: Well, it’s a little easier in that I would say, I’ve said this a lot to people that I’ve worked with and for is our greatest strengths are also our tragic flaws if used in abundance. And so the trick is how to counter the side effects there. For me, I have a detail orientation that I can’t ignore. I just notice small things and that can be really, really effective because that is where the devil is. Of course, the side effect of that, the weakness is an over-reliance on details prevents you from seeing the bigger picture and so I’ve got to push myself out of that to think longer term and more strategically.

Harry Stebbings: Can I ask, you said there about strength and abundance and maybe transitioning to a weakness. Do you agree with, “Hey, don’t bother working on your weaknesses, just elevate your strengths,” or do you think that you do need to have that combination of the two?

Travis Bryant: I think it has to be a combination of the two. I agree the underlying concept of StrengthsFinder is if you work on your weaknesses, you only get to mediocre when you should just work on doubling down or tripling down on your strengths. But I don’t know, there’s something about that that feels like it’s a bit of a cop out to say, “Oh, I’m just not good at this. I’m never going to be good at it. So that’s the way that it is.” I think you should really work to be a well rounded person.

Harry Stebbings: Yeah, I totally disagree. I way prefer the cop out of just leaving your weaknesses on the side. But I do want to finish though, Travis, on a slightly element, almost hindsight really, but it’s like what do you know now that you wish you’d known at the beginning of your time entering SaaS?

Travis Bryant: What I know now is the joy comes from the work or the craft mastery rather than the results or the externalities that come from that. I think when you’re young in your career, you’re obsessed with moving up the ladder, getting that promotion, getting the notoriety and recognition. And those come from an obsession over doing good work, in my opinion.

Travis Bryant: I’m not a huge management book person, but one that really resonated with me is The Score Takes Care Of Itself, which is one of the most famous, and you’ll permit me in American sports analogy here for a moment, Harry, Bill Walsh, who was the head coach at the San Francisco 49ers in the 1980s. Widely regarded as one of the most successful and cerebral coaches that has existed in the National Football League.

Travis Bryant: He wrote a management book about his lessons taking a poorly performing team and turning them into champions. And the message there was that if what you obsess over is the practices, the behaviors, and the competencies and frequencies, then you are controlling, you’re tipping the scales in your favor. You’re not in control over the outcome of the game. What you’re control of is the work that you do every day. And so just that joy of craft mastery is what I’ve become more comfortable with, knowing that if I’m doing that with vigor and improving and learning every day, then I’m tipping the playing field in my favor in the long run.

Harry Stebbings: You know, I absolutely loved that book, so I’m totally aligned with you there. But Travis, and this is one where I wished I hadn’t called it the 20 minute VC and I wish we weren’t time constraint, but it’s been such a pleasure to have you on the show and thank you so much for joining me.

Travis Bryant: Thanks for having me. It was super fun.

Harry Stebbings: My word, that was so much fun and huge apologies to Travis for going so off schedule with that one. But if you’d like to see more from Travis, you can find him on Twitter. Likewise, it’d be great to welcome you behind the scenes here. You can do that on Instagram at HStebbings1996 with two Bs. As always, I cannot thank you enough for your ongoing support and I can’t wait to bring you a fantastic episode with Ali from Mapistry next week.


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