How to Build a Truly Customer-Centric GTM Strategy

[00:00:08] Aaron Janmohamed: Welcome to the Revenue Mavericks podcast. I'm really excited to have a special guest, James Kaikis, who I've worked with a number of times in the past. We've, we've crossed paths a few times and, really enjoy each other's company.

Hopefully that's still in play. I'll let James introduce himself and his background a little bit.

[00:00:27] James Kaikis: Thanks, Aaron. Yeah, it's, it's great to be working with you again in a different capacity. Um, I, I've really enjoyed getting to know you over the last couple of years and work with you. I really enjoy your style.

A little bit about me is I'm James Kaikis. I am the head of go-to-market at a company called TestBox in the demo automation space, demo automation is always a funny term, but we actually focus on the live aspect, enabling your sales team, your SE team, your CS team to be able to present your product live best in class version.

Uh, what's interesting about me and Aaron, this is where we know each other is I'm the co founder of Pre Sales Collective, which was a global community for solutions engineers. And so we built that company. Uh, from an idea to a 35, 000 member global community, uh, an enablement business and sold that business a couple of years ago.

And after I decided to take some time off, um, decided to get back into the technology seat and what was important to me was actually overseeing all of go to market. And so that's, what's really important about today is I oversee all the functions of go to market. Marketing revenue team solutions team, which we've got multiple aspects of our solutions team, our value realization team, our customer engineering team.

And it's been amazing just to see the throughput and what we've been able to do as a team with just a single person in charge of the function to be able to move quickly and, and do what's best with the customer and mine. 

[00:01:45] Aaron Janmohamed: I, I knew given your background that you joining a test box would, uh, would come with some interesting waves that there'd be some disruption and you haven't disappointed, um, and you, we've had a couple of conversations, some of the things that you've been doing, honestly, are, are, are really exciting.

It's really cool. The transformation that you brought. And so I wanted to talk a little bit about that and it's going to be relevant to our audience. And so. If you don't mind giving us a little bit more background on, on, um, on business, um, and your efforts to essentially rebuild the GTM organization. 

[00:02:20] James Kaikis: Yes.

Uh, and I appreciate that. I, I think at this point, I've been no stranger to disruption over the last couple of years and some people love it. Some people don't love it, but that's the reality of business, right? So a little bit about the impetus of test box and how I know about test boxes. Uh, I'm an LP and go to market fund that actually invested in test boxes, uh, seed round in 2021.

And test box was born of a beautiful idea to be a marketplace for buyers and sellers. It was a place where you could go and test out software as like a proof of concept amongst different vendors. And then when you decided which. You know, software you wanted to buy, you click a button and get route to the sales team.

Amazing idea. They call it the utopia of buying and selling, uh, really hard to execute on, right? Really hard to execute on, really hard to monetize. Uh, but what was, what was really interesting about TestBox is Zendesk was an early big customer and Zendesk said to the team, Hey, you guys can demo our software better than us right now.

Could we use you for Demos and proof of concepts. And the team made a decision like, Oh, let's do this. And once they did that and they saw a lot of success and the demo automation category was growing. Right. And I know it really well because at pre sales collective, a lot of our partners were in the space.

And they said, Hey, I think the way we're doing this, um, is really, really good. And so they started making a transition in Q3. I signed on to be a consultant for a couple of months. We joked that we said we were kind of dating each other to see if it was a fit because me taking a job was almost like a founder level job without the without the co founder title, right?

And once I learned how TestBox was solving the problem, I say if transportation was being solved with bicycles and cars, TestBox showed up with an airplane. It's a radically different approach to demo automation. It's live, it scales, but what's so interesting is we had some really amazing customers In Q4, as we started pivoting and essentially the business went through a massive transformation.

There are only a couple people left from the marketplace. And so when I joined in December, we've been rebuilding the entire go to market motion. Uh, we've been actually rebuilding most of the entire organization from a product and engineering perspective. Uh, so one from an organization perspective, I thought it was really important if we were going to make a pivot.

We needed to, to get focused. We needed to have a niche and we needed to execute as quickly as possible. And so bringing in high caliber people to, and, and really figuring out what is the org structure that we want to do to deliver the best customer experience. And I could, I could dive into that. And then, um, what we were also looking at is the market.

Like, how do we educate the market that like, this is a different approach. I joke about the transportation example, because you could drive. From Los Angeles to New York, it just takes a long time, but now you can get in this machine and fly through the sky to get there. And that's a change. And that's scary for a lot of people as well.

And so it's been really amazing to see that. And so we at test box, um, you know, we've, we've grown in the last six months, over 150%. Uh, and it's just continuing to grow, which is amazing. We have something here, but the biggest thing for us is we are trying to deliver a premium experience, right? In a market where, you know, a lot of technology is, there's a lot of categories are saturated.

There's not a lot of differentiation. We're trying to figure out how we zag while everyone's digging. Right. And, um, from an org structure perspective, from a marketing perspective, uh, from a market presence perspective, and even from a product perspective. Uh, so happy to dive into any of those, but it's, it's been a really fun journey over the last couple of months.

[00:05:45] Aaron Janmohamed: Yeah, I mean, you mentioned to me that you've calibrated as you're going through this GTM build, you've calibrated the machine, um, towards the customer journey. And, and so what does that actually mean in practice? Like what, what, what, what would be different about the way that you're approaching it? That such that you are calibrated towards building customer alignment in a way that most organizations.

Yeah. Who claim to be customer journey oriented are not like I want to understand the difference there. 

[00:06:10] James Kaikis: Yeah. So, and I mean this respectfully, right? I've grown up in software. I've worked at startups. I've worked at awesome large enterprises. We say the customer matters, but internally it doesn't right. The customer doesn't matter.

Revenue matters. Renewals matter. Right. And we've kind of lost sight of the customer. And so if I, if I look back at. The overall buying experience. And I give you credit when you were at ConsenSys. ConsenSys did a really good job of bringing awareness to this. And I, I say that I've got a lot of my methodologies.

Uh, from consensus and Garen and the team, but you, a buyer has all these options online, right? There's so much information out there. Then they go through, uh, sometimes a really bad sales process, right? And then they're beat down by the end of it because they're talking to vendors. They're talking internally.

There's all kinds of battles internally. And then the contract sign. And I think what we've, we've been thinking the last 10 years is great. Things are good, right? But we're just starting a journey, right? And so many companies that I've talked to over the last couple of years. You know, they buy something, it's, you've had broken promises, companies haven't been able to deliver, they go through a tough onboarding process, and they're not realizing value.

And if we think about the market today and the shift toward efficiency, the, the scrutiny on, on, on spending, You have to be delivering value and really immense value and more value than the rest of the tech stack directly and non, uh, directly. So what does that mean for, for us? We wanted to, uh, take an approach that was customer centric.

So I think the biggest. The most important aspect of this is we have killed the word handoff in our business. You are not allowed to use the word handoff. We have an integration. Everybody has joint responsibilities across the customer journey. So what traditionally was a BDR ask questions and pass it to the AE who ask questions who pass to the SC who ask questions and then think about it, right?

I used to joke about an example in my like B2C world where I went to a vet and got asked the same question by five different people, right? Then the PS and CS team were asking the same question. And you're as a customer, like, I've already told you this. And so we've got a really aligned journey where everyone has joint responsibilities.

Our account executives are full lifecycle, right? Does that mean they're doing account management? Not necessarily, but they own the customer journey. Think about it. You build all this trust in the sales process, and then all of a sudden you hand it off to somebody else. And you say, see you later, right?

You have to transition trust within an organization, right? You're transitioning it between people. And that just doesn't come with a hard line and the email that says, thank you very much. So our account executives are full cycle. Um, they really have a point of view. They understand the market. They understand test box.

They understand customers products. And then we have a solutions engineer who builds out POCs and technical validation. What's interesting about that as a solutions engineer, actually, once someone becomes a customer. Leads the initial go, uh, solution delivery is what we call it. We have a solution design process.

And then solution delivery. So they have responsibilities to get the solutions architect and solution analysts and solution specialists up to speed on the customer and start transitioning that trust and the solutions architecture team is doing delivery, and then we have a value optimization team. So, uh, you know, maybe a controversial take his customer success is a company wide initiative for us.

We don't necessarily have a customer success team because it's company wide. We have a value optimization team who works with our solution delivery team, and we are taking a programmatic approach to making sure that customers are very successful, right? Customers come to us and they say, James, how do we make sure that we are utilizing test box effectively?

We, we see it across our install base. Why can we not tell you what a best practices we've got companies who, you know, need to make sure this technology works well for them. What can we do that? We've learned from, you know, dozens of other customers say, this is how you're going to get the most adoption utilization within your organization again.

So one, it's org structures. But two it's mindset and methodology, right? It's just a mindset within our business. We don't want to spray and pray. We don't take any business that isn't going to be wildly successful. And really if a company is not ready for us. Come back to us later. 

[00:10:16] Aaron Janmohamed: Were there any signals before you started going down this path?

Um, as you said, it's one thing to say that you're customer oriented, but then to actually put it into practice to execute on that is really difficult. And I would imagine has to be somewhat unique to your business. So this might be a stretch of a question. Were there any signals from your customers that helps you determine how you needed to structure things?

Like, what did you observe from From what TestBox was doing with its existing install base that helped you calibrate the thing the way it needed to be calibrated. 

[00:10:50] James Kaikis: I, it's a great question. And being super transparent and open is I think that we had, oh, uh, under, or excuse me, over promised and under delivered in a couple of cases, right?

Where, you know, we said we were delivering a premium experience, but we really didn't set the customer up for success. Uh, I would say also internally, we weren't set up very well. To make sure that the, the team, uh, was supported to be able to get the information that need from a sales process and then what the customer needed.

So we have a complex product. I'm not afraid to say that we have a complex product. We have customer engineering team, but what we do works. And what I saw, what I observed is like, what was sold in the sales process, right, to the handoff, right. The post sale without an SOW, even when we did like debriefs.

The information was not passing over. And I was having nightmares because I've started in PS. I've been an SE leader in my life. And I'm like, Oh my gosh, this is terrible. Like, you know, all this information is living in somebody's head. They try to put it down on paper and then they're trying to give it to somebody else in the org to make them successful.

And I found that like, We had deployments that when I was like first starting that we're taking a long time, there was missed expectations. Oh, they said that we promised this in the sales process, but we, you know, having to do this and real life, you know, friction with the customer. And I was like, this doesn't make any sense.

Right. Like we, we, if we want to be delivering a premium offering, right. At a, at a premium price point, we need to have our shit together. Right. Like we just have to have it together, deliver a good customer experience. And I think that was the biggest thing. Um, but really figuring out roles and responsibilities was a massive aspect of our business because as any early stage company, especially one that had a pivot, you're just kind of playing hero ball internal.

Right. And that was an observation of mine was like, we had a lot of really great. employees that were just, um, you know, would do whatever it takes for the customer. But like, that's not scalable and that starts to break. And as you know, I talk about transitioning to trust, right? As you start transitioning responsibilities as well, you start to see the cracks.

And I'm very operationally minded, right? Before I got into tech, I've been in ops most of my career. And so I just can naturally see these things. And I realized the friction points and what it meant for our customers. And if I go back to an earlier point that I made, if I think about that, we are competing in the tech stack to be like above the line and below the line, right?

If CFOs, you know, looking at the list, like how do we make sure we are a must have technology? And it's not just our product. It's how we support our customers. It's how we deliver value. It's the experience that they go through both in the selling process and the customer process. And so aligning that journey to just make sure that that was front and center.

has been super pivotal to our business. And we've seen a lot of successes since we've made that change. It's not perfect, but we've made a lot. We've seen a lot of success. Yeah. Yeah. Let's talk about that. What, 

[00:13:40] Aaron Janmohamed: what are some metrics and measures that are, uh, that give you an indication that things are working the way that they should, like, what do you look at as an, as a signal for, yeah, this is going well.

[00:13:50] James Kaikis: Yeah. So I think for us, uh, we are looking at adoption utilization, right? So taking a step back. I have felt that customer success teams, and it's not every team. It's it's not everybody, right. Have been very reactive in the way that they approach customers and some companies, it can be glorified support.

And I never wanted it to be that right. And so we've been looking at ways of why did they buy, what are they trying to influence in their business? And how are we supporting that? So looking at to say, like, you know, we have a couple of customers that the entire sales team is, is on test box. Right. We can go and see how they're utilizing test box and how often they're utilizing test box.

And then I, we've taken a step further. It's not just looking at the person. It's looking at the team. It's looking at the segment. Are they high performers? Are they medium performers? Are they low performers? And then creating customized paths and plans to support those people. If I'm at, you know, one of our bigger customers and the top AEs are not using my product.

That is a massive risk. And so we need to be proactive to understand why they're not using it. Get their feedback, roll that feedback into our product roadmap, roll that into solution delivery. And what we've actually seen, though, is sometimes middle or bottom performers are not using our product as much.

And so we go have some discovery with them to see what's happening. And they're like, Oh, I, I haven't been enabled on this, so I'm just not confident. And so we just take that a proactive approach. And so that's a very tactical example. But one of the things that I tell people all the time is if you're creating an aligned customer journey, you need to figure out what that value metric is.

You need to build plans around that adoption, utilization, whatever that metric is, and build proactive plans to handle that. And I think that has been a big one for us. Uh, we have started, uh, to see like. the effect on the business. I mean, we all want to talk about the business and the metrics. And controversially, I will say that everyone tries to claim that they influence win rate, right?

So if you, if everybody is, is, is influencing win rate, you know, what is, and, and, and how is it actually? And so we've taken some approaches to understand how we're influencing win rate, but actually how we're influencing deal acceleration. That's been our big thing. We had a customer who ran a whole new sales motion with our product and saw that their.

Uh, POCs went from 60 days to two days, right? And that is a really crazy change because they create a whole new motion in their business with workshops. So we're like, okay, that is working. And so we were able to see like the acceleration and new logo, velocity, acceleration, and deals. And so trying to take it as like a.

One, what are we doing from the business perspective? What are we doing from a proactive adoption utilization perspective? And what are we also doing from an overall customer experience? I think a lot of times teams want to justify their existence, right? So like, how are we multi threaded within an account?

So I can let the GVP, uh, of a business or an EVP know like, Hey, This is how your team is utilizing it. And these are the wins that we've heard recently. I just want to make sure that you're aware of that, right? So that we are ahead of renewals. We are ahead. We become that must have technology. You know, we've been invited to companies, uh, sales kickoffs, the, uh, you know, the president's club.

It's been really cool to see that because we are becoming an integral part of everything that they do. 

[00:17:03] Aaron Janmohamed: When I talk with RevOps leaders, two of the primary categorical problems they, they, they say they have to contend with include the visibility piece, which I think you've addressed, that's having access to data, trusting the data and knowing how to interpret the data to make decisions.

The other part of it is, is accountability, which you never get to without visibility. So let's, let's assume you've been able to see into the business. And, and kind of the impact that this new direction is, is had on, on, on things. Now you have to hold people accountable. You have to change the way that you hold reps accountable, the way that you hold yourself accountable, especially when you have this As a company wide initiative rather than an individual function within the GTM team.

So can you talk to me about how accountability has shaped and formed over the course of this organizational transformation? 

[00:17:54] James Kaikis: Yeah, wonderful question. Uh, one of my favorite words is accountability, right? You know, you could talk about these things all day long, but if you're not Making it part of your organizational DNA.

It's just words on paper, right? It's just words on paper. And so we at least go through a number of, I would say we, we, I'm not going to say we have a lot of meetings, right? But we have a lot of touch points internally where you are held accountable for certain aspects of your business. And you're not necessarily led off the hook, right?

We understand that things happen. But you're not necessarily let off the hook. And I, again, I use the word programmatic because we've been trying to take a programmatic approach, right? I, uh, maybe cause I'm a solutions engineer at heart, right. Or an operations person at heart believe that there are a fundamental.

Uh, repeatability aspects in the business, right? Like we can know, and we can look at the data, and we can look at the trends to see where there are similarities. And so how do we make sure that we are programmatically doing that? And look, like talk about accountability, the AEs who sell the deal are still responsible for the deal, right?

They're responsible for the ongoing success. Sure. Again, they're not doing account management. They're not answering questions on a daily basis, but they are responsible. For the health and again, proactively proactive reports, proactive metrics, having meetings where we talk about, Hey, this is where things are.

This is where a customer is trying to see ahead of churn and adoption issues. I think one of the things too, is like. A lot of companies are moving to AI right now, and this has like been our sweet spot. And so how are we kind of, you know, um, uh, for a hockey reference, right? It's games where the puck is, right?

So we see our customers are doing some things with AI. How are we proactively reaching out to their team, reaching out to their execs? Figuring out what we need to do. So that again, we are not reactive. That has been a big thing in my business. It's like proactive, proactive, proactive. Like it's hard to do, but again, a level of accountability and scrutiny.

Right. I, and scrutiny lightly, I would say throughout my career. Um, sometimes I've been known as a micromanager. Sometimes I haven't, but I tell people I micromanage the process. I have found that a lot of times in my career, someone could be really talented, but they just maybe run a poor process. And so I think we've got mechanisms in our business to hold folks accountable, to help folks responsible.

And it's a team effort, right? It's not easy. And especially like at our size, we're growing, we're rapidly growing. How do we make sure we're holding each other accountable culture of feedback at all times? Uh, that's been something that's been really imperative and it takes a leadership team to like all be aligned and all drive that and then everyone up from the bottom up to do the same.

[00:20:31] Aaron Janmohamed: So I, I have two final questions that I'm, I'm hoping to, uh, To get through before we, uh, we conclude the first one is really directed at people that might be going through a similar transformation, right? I, I'm sure there are a lot of people that are trying to build their, their organizational structures in a way that create that customer alignment as you talked about.

Yeah. So my first question is what's the biggest hurdle that you face if you, as you've gone through this process, like the, the, the biggest challenge you've encountered that you've had to fight through. Yeah. 

[00:21:00] James Kaikis: I would say the traditional norms, right? I, I believe in a concept right now called the rise of the generalist, right?

I think in a lot of organizations and a lot of tech companies, the past of the last 10 years of like having a lot of roles and responsibilities. I was talking to an executive, a really big company about this the other day, who it was a introduction from our, our VC who said like, we created all these roles and these responsibilities and these swim lanes over the last 10 years when it was growth at all costs, money was cheap.

And so there's just a fundamental way of how people approach things. And you have to actually take the layers back to understand why we think the way that we do. So for example, right. Um, just be brutally honest when I came into the business, right. Okay. I was told we have a pretty inbound business. I mean, mostly inbound at this point, um, moving a lot more toward that near bound, I was told leads are not the issue.

I was like, leads are not the issue because we have all this web traffic. We have demo requests, but I went a couple of layers deeper and started to find out what were the sources of the web of the traffic, what were the sources of the demo requests and how far did they move in the sales process? And I actually found that most of our business was fairly unqualified.

Almost all of it was unqualified, right? Just because the big company comes in, if it's an intern, who's like working on a summer project, that doesn't mean that that company is, is actually inbound, right? Um, and so I think like fighting those traditional norms and being like, we don't care about MQLs in our business.

I don't even care about SQLs in our business. We care about pipe gen, right? We care about pipe gen and we care about pipe progression and being able to identify lead sources. And even on that aspect too, let's talk about CS. Uh, originally when I walked into the business, it was like CS owns accounts after 60 days.

They own the relationship. They own the renewal. They own the upsell. No, absolutely not. Right. That is not something I'm interested in because we know that we have a land and expand motion, right? We've already seen customers who've had multiple upsells, even on a decent sized land. And so I think fighting these traditional norms and understanding, like, why do you believe that?

Why do you think that? Why is that your approach? And like digging into deeper, and I just find that You know, again, I'm a, I'm a product of this too. It was like the Latin, like golden era of SAS for the last 10 years. We just like think things are a certain way and we're running very similar playbooks.

And so, you know, a long answer to this is like always challenged traditional norms, because I personally believe we're going through this next wave of B2B SAS. I think we're going to see a lot of M& A. I think we're going to see a lot of, of ghost companies and, you know, it is what it is. And so how do you zag when everyone's zigging and how do you think about things differently to stand out when everyone's running the same playbook?

[00:23:41] Aaron Janmohamed: So the last question I want to ask is about what, what comes next? Um, I, you know, what are those alligators closest to the canoe that you have to kill in order to achieve the next phase of your, your customer aligned organizational structure objectives? 

[00:23:56] James Kaikis: Yeah, that that's definitely a question that's kept me up at night, right?

Because I always think like, what are we doing now? What are we solving for now versus what do we need to be solving for in the future? And it's finding that balance at all times. And I think. I've said this a couple times that we've got a complex product. I've got a customer engineering team, got very technical resources, right?

And we've had a great wave. We've been very fortunate, as I've mentioned, to have a growing business, especially in like this summer months that are typically slow. But what's ended up happening is because of capacity and we want to deliver a premium experience. You know, we're having to throw people at the problem, right?

We're going to have to just continue to add capacity, and that's not going to scale long term. And so how do we figure out, you know, things within our platform to find efficiencies? How do we find, you know, different programmatic approaches? To our business because that, you know, as I've been talking about, like we're scaling, but the more I add people, the, the more it affects my gross margin, my cost of sale, you know, our just employment costs, it affects our runway, right?

There's all these things that just adding people to the problem, um, causes downstream effects. And so we're trying to figure out. How do we do what's best for the customer? Deliver on a premium experience, but start to do that programmatically. Where can I find efficiencies? Where can we save four or five, six hours a week on a deployment, right?

Where can we find three or four hours on the ongoing value optimization aspects of our business? I think that's where we're at because. Again, very fortunate situation that we we've got some really great things in the pipeline, great big customers who have closed. How do we support them effectively without burning out our team and giving our team the resource?

I think one thing I highlight too is that about the traditional norms of things. There's a lot of ways of like, Oh, we need to solve it this way. It's like, why do we need to solve it this way? What is this noise? Or is this repeatability, is this just affecting one customer? Is this affecting 10 customers and really having that lens on everything that we do has been mission critical, right?

Cause we don't want to slow the ship down. We want to continue to do things what we knew need to do in the short term, but also focus on that medium to long term to make sure that we've scaled the business effectively, uh, you know, for three, four or five years from the line down the line. 

[00:26:07] Aaron Janmohamed: That's really helpful, James.

Thank you so much for your time. Uh, anyone listening to this, you got to follow James. His advice on LinkedIn is probably the one of the most helpful, um, that, that, that I find in that massive ocean of, uh, of people throwing out their ideas. So, uh, definitely worth, worth a follow. Uh, thank you so much, James.

[00:26:25] James Kaikis: Yeah, Aaron, thanks for the opportunity. I appreciate the kind words, always a fan of what you're doing and what your teams are doing, and thanks for the opportunity to share what we're doing here. I want to continue to, you know, help lead this charge, uh, to help go to market professionals, be able to work through this next wave of B2B SaaS.

[00:26:43] Aaron Janmohamed: Awesome.