Anatomy of a Scale-Up with Jason Holmes (COO of Showpad)

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This is a podcast episode titled, Anatomy of a Scale-Up with Jason Holmes (COO of Showpad). The summary for this episode is: A scale-up is typically a company that has found product-market fit, has created more specialized roles within an organization and is in the process of building a repeatable, predictable machine for growth. And while there are tons of books, webinars, conferences, and coaches dedicated to this concept – it’s a whole other story when you get a chance to talk to someone who’s actually in the middle of one right now. So on this episode of Operations, Sean and Jason Holmes, COO of Showpad, break down the processes behind a successful scale-up. Want to hear some of Jason’s biggest lessons learned from his time scaling Adobe and Marketo? Listen to the full episode.

Sean Lane: Hey everyone. Welcome back for another episode of Operations, the show where we look under the hood of companies in hypergrowth. My name is Sean Lane. One of the ways you hear people talk about hyper- growth companies, sometimes, is they refer to this transition from a startup to a scale- up. Now there's a bunch of different definitions out there. So stick with me, but in general, a scale- up is typically a company that has found product market fit, has created more specialized roles within the organization and is in the process of building a more repeatable predictable machine for growth. There are books, webinars, conferences, coaches, all dedicated to this concept of the scale- up. But I didn't want to just look at these graphs that go up into the right. I want to dissect the anatomy of one of those scale- ups with someone who's in the midst of it right now. Luckily for us, that's exactly what we're going to do today with our guest Jason Holmes, who is the president and COO of Showpad. Jason joined Showpad, which is a sales enablement platform, in August of 2017, after five years as the COO of Marketo and three and a half years as the VP of global professional services at Adobe before that. Now, in his two years at Showpad so far Jason and his team have grown to 430 employees worldwide, largely in its headquarters in Belgium and a growing office of about 160 people in Chicago, which is where Jason's based. They've also raised a$ 70 million series D in June of this year. So they've been busy. In our conversation, Jason and I talked through his approach to a scale- up and the specific ways he approaches different parts of his organization, the same way he approaches different parts of the customer journey. From marketing to sales, to post- sale. And honestly, he gives us a complete PhD on professional services. So, whether you're in ops or you're a CRO or a VP of customer success, there's a lot to learn here from Jason's journey and lots and lots of swim lane metaphors. Seriously. All right. Let's start at the beginning when Jason arrived at Showpad in 2017 and how he approached entering that scale- up from day one.

Jason Holmes: So, in terms of coming into Showpad the way that I think about the order of operations of what to do first is essentially, I think about it in many ways, like you think about the company in terms of how to grow it. So, it starts at the top, from a go- to- market standpoint, it starts at the top of the funnel. So we have to worry first about brand and awareness. And then we have to worry about getting that into lead flow and there's lead flow happening and then into the sales organization and then into the implementation team and then the success organization and so forth. And so fortunately, when I joined up here, the company had really good momentum. And so the momentum and the growth and all of the metrics of the business were quite solid. So this was certainly a good to great situation, not a turnaround situation, if you will. And first and foremost was really starting in the marketing organization and from our organizational looks standpoint and working my way through each team in sequence, according to how we want to build and continue to increase or accelerate the momentum of the company.

Sean Lane: So, you're basically looking at it like a funnel. And your approach is to start with the team as the highest up in the funnel and work your way down.

Jason Holmes: Right. I mean, just sort of the captain obvious comment is, if brand isn't where you want it to be, meaning just lack of awareness, or if you don't have a lead pipeline, it doesn't make a lot of sense to go hire a bunch of salespeople. And if you don't have a sales team hitting on all cylinders, going out and finding 10 customer success people, or trying to really clarify or improve that process in some way, just strikes me as being out of order. And so simply that, I mean, that's just start at the very top, okay, what are we going to do with analysts? We need to rebrand the business, change our logo, change our style guide or fonts and so forth. Then that's going to move into how do we do an all new website and so forth. Then that moves into ripping out our old lead management system and putting in Marketo in its place and then standing up and using it from a lead nurturing standpoint, then building out a BDR team and so on and so forth. So, it's actually been quite a methodical process that's really unfolded over the course of 18 to 24 months from my standpoint.

Sean Lane: Okay. So what I wanted to do for this episode was break down that methodical process that Jason is describing here. And as he mentions, to do that, we're going to work our way through the funnel. And with each phase of the funnel, Jason taught me that he starts first and foremost with a talent.

Jason Holmes: Essentially I've gone out and rebuilt the executive staff. So part of the timing of it is just in which order do you hire people in the executive staff? So I just started with marketing and then marketing therefore gets out to a headstart as it should, because that's at the top of the funnel. And it takes a certain amount of time to rebuild a brand and redo a website and to get Marketo put in and getting leads flowing in a certain way. It was immediately subsequent, like immediately following, let's say a couple of months following marketing leadership and some core directors in the marketing organization that we went out and hired new BDR management into the organization as well. And so, it was an order of operation of hiring that person or those group of people, and then starting to fill out those teams. And then my next logical thing was to go out and find a CRO to say, now we need to really, now that we've got marketing moving... Part of this is sequential, but it's also like, what you can't do is wait two years for marketing to crosstalk.

Sean Lane: Right, exactly.

Jason Holmes: crosstalk process and then start your sales process. So I just view it as like different swim lanes in that first swimmer is going to get out to a lead, but that second swimmer needs to jump and follow just a few meters behind. And then the third swimmer needs to jump and follow a few meters behind the second swimmer. So, that's the way that I've executed it. And I think that's the practical reality of rebuilding an executive staff and a go to market organization, is those processes tend to take three to six months to unfold. And I think that it gives the right amount of separation in terms of creating momentum, again, in order of the funnel sort of top to bottom.

Sean Lane: And one of the things that you and I have talked about in the past is this idea that while you're rebuilding all of these things, you can't have the expectation, to further your swim lane metaphor, you can't have the expectation that sales is going to be ahead of where marketing is while marketing is ramping up. So I guess my question is like, if you have those higher expectations in marketing, how do you frame that to the sales organization while the rest, the further up the funnel, is kind of getting its act together?

Jason Holmes: Yeah, no, it's funny. I actually have a really specific example of that from just this last week. And I was talking with sort of the person that does our analyst relations and some of our PR earlier today. You're right, I mean, the reality is it takes a while for brand to bake in a market that's hard to measure and it takes a long time and it's hard to know it when you see it and all of that. And sure enough, we hire in a BDR team and then a sales team and the sales team, of course, the first thing they say is brand isn't where I want it to be. I don't have enough leads. Regardless of the fact that it's better than it was six months ago, but they show up in they're immediately critical. And then what happens is here we are about a year into the sales build or rebuild right now. It's just a little bit over a year to the sales rebuild. And one of my senior executives in the sales organization said, " Hey, Jason, the good news is, everybody knows who we are now." And I found that to be like a little bit of gold. So the reality is this guy shows up, he builds out a team here in the Americas. Yes, the brand isn't where I want to be quite yet or work you wanted it to be. But the fact that we've gone down the road now 12 months and he's like, wow, as it turns out, like just since he's been here, the brand has gone from A to F in the process here. And so, I do think there's an expectation setting process that I'm constantly doing reminding people, " Hey, just so you know, two years ago, much of this didn't exist. And six months ago we made a bunch of changes and we expect to see those." So you just have to constantly communicate and stock constantly expectations around the organization so people understand where in sort of the gestation process each of these teams are.

Sean Lane: As any BDR or sales person will tell you, when someone on your sales team says, " Hey, people know who we are now", this is an enormous milestone. And even if it's a small one, every milestone you set for your business can be a place to celebrate, to continue to bring that milestone up and shine a light on it. And ultimately use that to build more momentum for your team internally. A simple reminder like how many leads do you have today versus how many you had at this time last year. Jason told me that if you can communicate these effectively and your team can see those graphs going up into the right, that can make a huge difference for the team. So, with sales and marketing swimmers off to a good start in their respective lanes, I then asked Jason if it was time to turn his attention post- sale.

Jason Holmes: It is. And so given we're a year into the sales one, it was about seven or eight months ago that we really got on with customer success and changing leadership in customer success, changing the philosophies and what's important. What do we measure? How do we want to incentivize those teams, so on and so forth? And so that happened shortly after the sales change outs and the degree of sales changes that we've had. And then subsequent to customer success, which is a piece that we've done a little bit more recently, is over the course, like starting in January, February, it was getting sort of industrial strength services between services like professional services and support. So how do we do case management on a global basis within the right level of SLA and so forth? How do we do services? Not just for small little mid- market implementations, but how do we ultimately do very large global deployments with enterprise customers, either on our own or with partners in some way as well? Again, so the marketing thing is way out in front and then the sales thing is just right behind marketing. And then this whole concept of post- sales is something that we've really worked very hard on over the course of the last nine months.

Sean Lane: And so, I definitely want to come back to the professional services piece, not only what you're doing at Showpad, but kind of what you learned about that from your time at Marketo. But before we get to that, I want to kind of get your sense on how you just philosophically think about what the setup should be post- sale. And so everyone, every company, every high- growth company thinks about this a little differently and goes through kind of different evolutions. I'm curious, how do you think about the different types of teams you need post- sale and kind of the division of responsibilities of those teams?

Jason Holmes: Sure. Big question. So I'll give a few different answers. First, I think there's the post- sale responsibility for making the customer successful and showing value to executives and decision makers inside of those customers. So, what's the customer experience is one leg of that discussion and the other leg of that discussion, not separate they're related, but I think about them in a little bit separate way, is how do you then continue to work with those successful customers who are getting value to continue to monetize and grow that base? So, the thing that most SaaS businesses want, which is high net retention. So in other words, what they have, keeping all the customers that you have and then cross selling or upselling them more solutions. In the post- sale world around customer experience, and I very much view the quarterback of that customer experience, is the customer success management function inside these SaaS businesses. So the customer success managers should be made aware, or should be introduced into a late stage sales cycle saying, I'm your guide. I'm the person that will be with you forever and making sure that you're getting value from our solution. And then I believe that there are two role players along way that happened from a customer experience standpoint. One of those role players is the professional services team who essentially does the onboarding and or implementation of the solution that has been sold. And I think the other role player is the support organization. So I don't know how to do this, or I think you might have a bug or Sally's browser isn't cooperating with your solution right now, can you help Sally out with some sort of a solution? So I very much view customer success management, being the overarching quarterback over those things. And then obviously CSM, customer success management, is responsible for constantly making sure that those customers see value doing QBRs with those customers, getting early warning signs of lack of adoption, being both proactive and in some cases reactive to make sure that you're keeping just as many customers as you possibly can.

Sean Lane: Whether you ascribe to Jason's exact division of post- sale roles at your company or not. I think everyone can agree with his desire to be more proactive than reactive in your customer success organization. But this can be really difficult in a hyper- growth environment. Keeping pace with your customer base can be really challenging all while trying to deliver a superior customer experience. So, I wanted to understand from Jason what those early signs of good look like in the development of a CS team.

Jason Holmes: First, I think it's important to sort out how are you going to gauge and measure the success of your base? And I mean, the things that I generally see, whether it was Marketo or my time at Omniture, Adobe, here at Showpad, the things that matter to me are gross and net retention. Those are generally pretty late in the process though. Like it's not really easy to get ahead of some of those issues. I think it's quality of implementation. I believe that 60 to 75% of churn happens during the first 90 days of the customer experience. And if you can get that first 90 days of a customer experience dialed in, you can drastically impact your churn. And so that tends to be, are projects finishing on time? Are you doing an NPS survey or some sort of a survey at the end of that? Are you recentering with a CSM and implementation person and an executive at the customer at that conclusion of implementation and going through the formality of saying, did we satisfy what you expected when you bought this in the first place? But really dialing in that first 90 days, I think is as valuable as just about everything else combined. And then I do think ultimately in most situations, not quite all, but in most situations, people just view, are they using your technology or aren't they? Are you getting sort of the weekly average user, monthly average user, annual usage of your platform or your solution and making sure that you're keeping very close tabs on that. And always trying to grow that usage. Because the usage is a proxy of adoption and adoption can be a proxy for overall value that the organization is getting from whatever SaaS solution you've implemented.

Sean Lane: And are you kind of reinventing what core measurements are at different points in that evolution? Or are you kind of setting the bar early? Like these are the things that we ultimately want to get to, these are in our stars? Or is that kind of something that happens incrementally along the way?

Jason Holmes: It definitely happens incrementally and even zooming out from this discussion about post- sales. As I look at metrics more generally, I am a huge fan of, frankly... There's a million things you could measure. I try to work very hard to say these are the eight that are going to matter. And then the next year eight goes 10. And the year after that, 10 goes to 12. So what I always want to do is lay down a baseline that you can get people's heads wrapped around inside the organization, and you can get people understanding. You can get them rowing the boat in that direction. And then you incrementally lay down additional process and additional metrics on a quarter on quarter or year on year basis. I think one of the mistakes I see, A, is you get this silly thing that happens where people measure almost nothing, or they have nothing reliable on which to base decisions, which is an awful place to be. I think the more common thing is there are so many things to measure, and frankly, there were so many opinions on what matters and what doesn't, but somebody has to take an authoritative position saying, these are the three things that matter. And this is all I really care about for the next year in this business. And once I feel like we're dialed in here, I might drop one, add one. I might go from three to four, but trying to start at 12 or 15 in a function, for example, is just a silly place to start.

Sean Lane: And do you view that kind of like as your role as president and COO to be the person who dictates those things. Because I can completely empathize with what you're saying that as we've grown at Drift, as our business units get more sophisticated and similarly working your way down through the funnel, like everyone wants to measure everything. And so where I struggle is like, how do we make sure that we have the discipline to pick the right things to measure, knowing that there's a million other things out there that we could measure, but not necessarily saying like we have to switch this up every week because we know there's this other potential metric out there that could be indicative or helpful or insightful for us?

Jason Holmes: Yeah, no doubt. I mean, I do with sort of my title is president and COO and I find those to be actually two different things. It's more of the COO side of my brain that I think about that. And yes, I think you have to have an executive that is willing to say less is more, let's keep it simple and it's going to make that as standard and something that's acceptable inside the business. And is constantly vigilant to make sure that we're not over- complicating different parts of business with too many metrics or too many processes or too many changes or keep it simple, keep it simple, keep it simple. And I'm like the chief keep it simple officer. And whether that's inside go- to- market, which is what I have proper responsibility for or the rest of the company, I'm just a huge advocate for complexity does not scale. Not even if people put the key word sophistication in, instead of complexity, it's still complex if it's sophisticated. And ultimately just doesn't scale. I think metrics is just one place where that evil can live if you overdo it.

Sean Lane: Complexity does not scale. Did you catch that? Complexity does not scale. He's right, that there are a million different things you could measure, but Jason is very purposefully taken a less is more approach when it comes to the evolution at Showpad. And what I find more interesting, he actually views it as part of his job description to help his organization to keep things simple. I'm convinced after talking to him that every hyper- growth company needs someone to play that role. But there is a potential pitfall here that I wanted to explore further. What does complex actually mean to Jason? If complexity doesn't scale, did Jason have a gauge for what he actually deems to be complex?

Jason Holmes: Well, I think it's super simple for me. I just put myself in the shoes of, if I'm a new customer success manager that started in the last three months, or if I'm a new account executive or I'm a new manager or, we used to say something at Marketo, if I zoomed in from Mars and I wasn't part of this business and you were trying to explain this to me, do I actually understand what it is the heck that you're talking about? And if the answer is no, then it's too complicated. And I didn't bring that necessarily to Showpad, it was something I found that really resonated with me in joining this company. One of the core values of the company before I started was keep it simple. And I think that that is a core part of why even our product and product design is quite successful, is because we've done a really nice job of keeping it simple. So if our part design is simple, it seems like how we run the business should be simple. It seems like how we hire people should be simple. It seems like we should keep it simple on training. And I think that also shows up in terms of, as we layer on process and do this scale up, the combination of process and metrics also needs to continue to carry the same flag of keep it simple.

Sean Lane: I don't know about you, but I am definitely stealing that zoom in from Mars line. It may sound funny, but it's so easy to go deep into the weeds of the way you do things or the way things have always been done at your company. The zoom in from Mars hypothetical is a great gauge for how good of a job you're doing there. Okay. Back to our swim lanes, we've got marketing, sales, customer success. And I promised earlier we were going to circle back to something that Jason knows a ton about, professional services. And what I was really curious about was how a company knows when it's time to start offering and ultimately charging money for those professional services.

Jason Holmes: When you're a really small business, what happens is you build a product and then you go find your first sales rep. And then you sell something which is great. And then somebody actually has to implement it. And the first few your engineering team probably implements or something along those lines. Then eventually you say, well, I need engineers building products. So you go find your first post sales person. And they do everything. So, essentially you start with a one person or two people and they do everything. The first thing you break apart is you break up the support function first. Because that is all about time and responsiveness and case management. And that is absolutely the first thing that you have create as a separate function from a post-sales standpoint. So, you've got somebody that's in your support department, probably one or two people. And then you have the other people that do everything else. They might do the renewal, but they certainly do the implementation. And they answer some of the value- based questions and so forth, but you have two teams inside of post- sales. I think as those teams grow, like a lot of companies will grow up and they'll have 10 and then 15 then 20 and then 30 people in those two teams. Ultimately those, you start looking at that non- support side of post- sales. So customer success or service, or whatever you call it. Ultimately what happens is you need to get to a point of repeatability of how to manage that first 90 days. So I said earlier that I think that the majority of churn happens in that first 90 days. And the majority of the reason that churn happens in the first 90 days is, A, the product was a bad fit. That clearly can be and is a huge issue, especially early on when you're finding product market fit. And I think the second is you do not have a repeatable implementation approach. And so, the next evolution from having two teams is essentially having three teams. So you've got a support team that hopefully is clicking along and is doing case management quite well. And then you've got to split the CSM function and those professional services function into two teams and PS has got to be all about repeatability. So how do we repeatedly get customers through that first onboarding and implementation process to make sure this thing takes consistently so that I can hand it to a CSM who can manage it month in, month out or quarter in and quarter out after the fact. And so that's how I think about them growing up. And then obviously there was a huge follow on to how do those teams evolve as well. But that's how I think about the early days of making decisions, probably on your way up to 50 people in your post- sales function or something like that.

Sean Lane: Got it. And then do you make a distinction then between, the way you're describing professional services in that early evolution sounds like it could be what some companies call an onboarding team or an implementation team, at what point do you see a distinction there between, hey, this is just a part of our kind of like post- sale expectations for our customers when they sign up with us versus this is a separate paid service or separate and apart from the typical things you get from our post- sale team? Do you make that distinction?

Jason Holmes: For sure. So Marketo is probably a pretty good example. When I joined, the company had about 30 million and had just introduced the concept of paid services. So it went from like a batteries included to a, we're going to sell you some ARR, some subscription and we're going to sell you sort of the launch pack is what we call them. So it's, here's your 30K ARR deal and here's a 5K launch pack that goes along with it. And I think there's a few things there. One is you should monetize it, because people will pay for it. If people don't pay for something, they don't tend to pay real close attention to it. They don't value it essentially. And B, you obviously you need to build out a services organization and it needs to be funded in some, and you're really not funding that services and implementation process. So you sort of have customer expectations that they should pay for it. And so you should charge and ultimately you can use it to fund building out a good team that does highly repeatable processes in terms of implementation and onboarding. We've gone through the very same evolution here. So it was, I showed up and we had list pricing we just didn't charge for it. And I came in and just said, we just charge. I just changed the policy one day and said, from now on we charge and we don't discount. And that's exactly where it sits today. And we went from having no services revenue to a couple million bucks worth of services revenue last year. And it will certainly be well over that this year, not in the spirit of, we need to go build a big services team, because it's actually quite small and quite capable, but simply A, a customer expects to pay for it. And B, when they do pay for it, you know what they do, is they actually show up on those phone calls and they actually lean into that project because they've spent money on crosstalk.

Sean Lane: That's a part of it that I hadn't thought of is like, from that customer's perspective, if they're paying for it, they inherently value it more. Whereas someone who's just going through kind of like a typical implementation process that maybe is just like bundled in as a part of what they're paying for their subscription. It might blow off that first kickoff call or that technical integration that they were supposed to show up for.

Jason Holmes: That's exactly right. So, I mean, I think it's a fundamental part of the psychology of the value exchange. To speak in big fancy words, but that's how I think about it.

Sean Lane: And I would imagine at Marketo where first of all, it's not a cheap tool and the implementation is a heavy work intensive process. Did you see that theory of the work that happens in those first 90 days kind of prove out as you guys started to actually implement a cost there and were monetizing that implementation?

Jason Holmes: I think that certainly it went quite well. First, the level of we don't want to pay or a sales saying they don't want to sell it. Like the noise was quite low on that front. And I actually credit the sales leadership at Marketo with that. It was accepted quite easily and quite well by Bill Binch, who was the guy that ran sales over there, a good friend. And I think the uptake was quite good. And once you get over that hump, then it just becomes about, okay, now we actually have to show up and show value here. We've inaudible our value and you're going to pay for it. Now, how do we get the right people in the right jobs with the right process and the right deliverables with consistency and predictability that ultimately lands these customers in a consistently happy, satisfied, high value place at the end of this 60, 90, 120 day timeline? I think we very much saw that unfold at Marketo and I'm oversimplifying it a little around kind of the mid- market smaller pack business. There's also then this follow on, okay, now we need to do real implementations that are quite large. Like how do we do the 300,000, $400,000 larger deployments global inside of enterprise customers? That's actually a completely different animal. I mean, that is less about sprints and agile. That is more about, in some cases, a waterfall type methodology that is, we have requirements. We have to do change management. We have to design. We have to do the formalities of sign- off. Sort of a classic enterprise deployment methodology that's been adapted to SaaS highly agile world essentially. And that's work that we definitely built out of Marketo. There was a woman I hired that came in and helped build that out for that whole team. And similarly are implementing and doing exactly that here at Showpad as well.

Sean Lane: What did that group kind of evolve into? So by the time you left Marketo, what does that professional services team look like inside the organization?

Jason Holmes: So I think there are first it's split geographically. So you have an inaudible team and the US team. And then second, there's absolutely a separate mid- market team versus an enterprise team. So mid- market team is all about fixed price, small packages, high velocity, high repeatability, and speed to value, essentially, because that's what mid- market customers expect. And that team runs at a very different tempo than the other team, which is the enterprise team. And that enterprise team moves about as fast as giant enterprises do. And all with the formality that's required inside of these large enterprises. You've got lots of voters, there's lots of peanut galleries inside of these enterprise businesses. IT has a say, and marketing needs sign off and sales needs sign- off and then someone you never met in the process needs to sign off on the design. So classic project management, stakeholder management, like I said, enterprise implementation methodology that's adapted to SaaS and the world that we live in today versus the 1985 ERP implementation or something. So that's when I left Marketo, I should say, it was very much about a geographic split and then an enterprise versus mid- market split. And then maybe the third thing that we haven't talked a lot about was that team definitely had, and I believe still has, a dedicated training function as well. So that's a whole other domain inside of post- sales, which is education. So how do you educate customers before they implement, while they're implementing, years after they've implemented both on the administrator side and on the user side. How are you continuously educating those customers? And so that's yet another function that gets broken out of that post- sale experience to optimize education and the spirit of adoption and success of those customers.

Sean Lane: Got it. And is that where things like Marketo certification come born out of?

Jason Holmes: Yes. For sure. So the certification process came out of that. Marketo Education or Marketo University came out of that. In fairness, I think HubSpot has just done a great job with education. Basically using education as a proper funnel exercise. So they've really A, nailed down the education side of things from a post- sale standpoint, but also extended it into a marketing exercise and a top of funnel exercise. But I think it's just paid huge dividends for them. And especially given a company like HubSpot, for example, lives much more in the SMB mid- market space. It's just essential that you figure out a way to solve for education on a one to many basis, because it's the only way you can afford to educate that people, is you've got to nail process down. And I think they did a really nice job doing it. Marketo, I think we did a pretty good job on education on a relative basis.

Sean Lane: I'm smiling because the guy who helped build out HubSpot academy, his name is Mark Kilens. He now works at Drift. So he will be very happy to hear the praise on that, for sure.

Jason Holmes: Yeah. Well, you give credit where credit is due.

Sean Lane: Before we go, at the end of each show, we're going to ask each guest the same lightning round of questions. Ready. Here we go. Best book you've read in the last six months.

Jason Holmes: The Subtle Art of Not Giving a-

Sean Lane: That's all right, you can swear. That sounds amazing. Any like just quick like synopsis or what is it about.

Jason Holmes: Give up on trying to be happy all the time, just choose your pain and power through your pain and you'll have a fulfilling life, I think was a bit of it. And the other is just, you have to pick your priorities and you can't care about everything. And so this gets back to the keep it simple theory that I have and I think that Showpad, as in general. That I think is essential to running a good company, but also actually having a fulfilled life.

Sean Lane: Love it. Favorite part about working in operations.

Jason Holmes: I clearly thrive on leadership, inspiring people, seeing people succeed. Hiring people, training them, watching them succeed and repeating that over and over and over again is absolutely what does it for me.

Sean Lane: Least favorite part about working in ops.

Jason Holmes: That's a tough question. There's not a lot about my job, that I'm not a big fan of. I would say, when you find that person that probably isn't a great performer and the process that ensues from that is emotionally challenging, but necessary.

Sean Lane: Someone who impacted you getting the job you have today.

Jason Holmes: I'll probably go back a little ways on the answer to that question. So I would say that one of the people that have the biggest impacts on my career was a guy named Godfrey Sullivan, who is chairman at Splunk. He was CEO at Splunk. And years and years and years ago, I was a wee consultant at Hyperion. He figured out a way and I had something to do with it. I hope to move from that to running services of a 400 person team over the course of about three years. And I continued to look back at that saying, I had so much career acceleration then, but I think a lot of it has just been paying attention, learning along the way, but that was really the catalyst.

Sean Lane: That's awesome, and last one, one piece of advice for people who want to have your job someday.

Jason Holmes: I would say you have to balance and understand the human condition and making sure that you know how to lead and inspire people is incredibly important, but you also have to pay attention to the details, the numbers, the metrics, the processes. And if you can do both of those and live in both of those worlds at the same time, I think that you can successfully run as a general manager and an increasing executive. Lots of people struggle with doing both of those simultaneously.

Sean Lane: A huge thank you to Jason Holmes for joining us on today's episode. And also thank you to Caroline Hoffman who helps set up the entire interview. That's going to do it for us on today's episode. If you want to learn more, we mentioned a little bit about Mark Kilens, who built HubSpot academy and Jason gave him a nice shout out. Mark is now Drifts VP of content and community. And he and his team have built this amazing resource called Drift Insider. If you want to check it out, go to drift. com/ insider. There's a ton of completely free content on there about conversational marketing, growth, marketing. There's some great talks from some of our hyper- growth speakers. There's even a couple Operations videos from me on there. So if you want to check that out, go to drift. com/ insider. And if you're enjoying the podcast, as always, leave us a six star review on Apple podcasts. Thanks very much for listening. That's going to do it for me. See you next time.


A scale-up is typically a company that has found product-market fit, has created more specialized roles within an organization and is in the process of building a repeatable, predictable machine for growth. And while there are tons of books, webinars, conferences, and coaches dedicated to this concept – it’s a whole other story when you get a chance to talk to someone who’s actually in the middle of one right now. So on this episode of Operations, Sean and Jason Holmes, COO of Showpad, break down the processes behind a successful scale-up. Want to hear some of Jason’s biggest lessons learned from his time scaling Adobe and Marketo? Listen to the full episode.