Gary: I know I shouldn’t be surprised, but I still am surprised. Every time a sales leader tells me he needs more leads or an investor asks me how many MQLs are you going to deliver to sales? Or the CEO tells me she needs more pipeline, when the pipeline that’s been created is mostly languishing in early discovery in demo opportunity stages.

These attitudes are emblematic of the toxicity that’s endemic to the organization, where marketing is relegated to merely being a provider to the sales organization, and when, inevitably, those leads don’t close, the finger pointing begins. You’re not giving us enough leads! You’re not closing the leads we give you! There are better ways to do this.

When you have the right leadership team with an aligned CEO, CRO, and CMO, you can create and execute on a GTM strategy that ensures that your customer-facing teams, rather than pointing fingers at each other, work together to collaborate to drive revenue.

As the first head of Marketing for series A Ed Tech startup, Transfr. I built the go to market strategy that created sufficient pipeline for the company to triple its revenue during the time that I was there. The strategy featured alignment on key metrics. Not MQLs, although we did measure them, but on opportunities that we generated for and with the sales team.

I am delighted to be joined today by Chris Adams, a veteran B2B SAS sales leader with whom I enjoyed a tremendous alignment during the time that we worked together. Chris will discuss with me today how we collaborated to build a go to market strategy that allowed us to hit our goals as well as hitting company goals.

2:18

Gary: Chris, it’s great to have you on the What Great Looks Like podcast today. Tell us about yourself and a bit of what you’re up to these days. 

Chris: I’ve been very focused on an AI healthcare startup that’s changing the world of physical therapy and how people gain access to great care.

So it’s been a lot of fun. I’ve only been here for a few months. So it’s been a wild year of building and just having a great time. I feel like every company is going through tons of challenges in this turbulent economic time. But it’s a ton of fun to be in a high growth startup.

2:48

Gary: That’s awesome. And, you know, we did a little bit of high growth startup together. And you’re right, it is pretty much a really turbulent market. Yeah. And so you know, I think it’s perfect because the subject of what we’re talking about today is how sales and marketing leaders can align in this kind of market to make sure that you’re delivering, you know, that high growth.

So I’d love to talk about the process that we built at Transfr. You know, that company was a high growth startup. It was very aggressive. Yeah. Our goal was to triple revenue in the first year after the company raised its series A funding. You and I attacked the GTM strategy and plan together. What was foremost in your mind as we started the planning process?

3:31

Chris: I think we had a few things going for us and a few things going against us, like any startup or any newer company. Thing number one, I think, the thing that we had going for us the most to focus on the best and most positive part was we had a really clear idea of what was working in the sales process.

So not to give away too much of the secret sauce for the company, but effectively we knew really well who our ICP was and who was buying the solution, their motivations for buying it, and the people who bought it were very consistent from company to company or from organization to organization. So, we were starting with a very small number of customers, but it was very clear what the buyer looked like.

And then I would say the other big thing that we had going for us, that was maybe a challenge, was we really had an open opportunity. There weren’t a lot of there wasn’t a lot of revenue. We were starting with a few hundred thousand in revenue, not even millions. And our aim was to go and build that into millions of dollars in revenue.

And so it was a big, big challenge, big opportunity to build. We also had the fortunate opportunity to really start from scratch. There weren’t existing playbooks, there weren’t a lot of materials. So we were kind of afforded a blank canvas, which is a lot of fun. And, in my experience, to be able to go craft it how you want it versus trying to fix old issues or things that may not be as easy to go and solve for.

4:46

Gary: Yeah, you’re right about that. It was kind of fun building from that, you know, completely a blank slate. And while we understood the ICP, I think we were really trying to focus on a couple of groups. it was an Ed Tech company. We’re looking at, local government, right. Workforce development agencies, community colleges, which seemed to be the sweet spot.

And I remember we built lists of all of the workforce development agencies in all 50 states. We built a list of all the community colleges. And we were looking at taking over the world or taking over the US, at least, county by county. How did that impact how you structured and built the sales organization?

5:31

Chris: At least in that particular moment, like I said, we were in the good fortune of having two really successful sellers who had modeled out what worked well, what didn’t work well, you know, we knew what didn’t work well before I arrived or you arrived. But I would say the biggest thing that we had going for us is we were very crisp and very clear on who we were trying to sell to.

We had the accounts mapped out, the influencers, the different groups. It was very much an enterprise sale. We weren’t trying to pepper all of America with the message we had. I think if I recall, you know, six or seven hundred potential accounts that we could sell to. So we knew we had to be very precise with what we were saying and how we were going to market.

I think that led to the type of sales professionals we needed to hire, the types of people on our team that we needed, etc.. So it was a very crisp, very defined process for how we were getting started, which generally I think is really important, especially in the early days. You just don’t have the good fortune of trying lots of things,

You have to use your bullets very carefully. 

6:32

Gary: What were kind of the key things in that process that you found worked really wel?

Chris: I think being that crisp and clear, also getting out on the road, I mean, the first one of the first sellers that I hired, we went on a tour for one week to see the entire state of Louisiana all in one go. And then the next month, we did the entire state of Mississippi. We ate at every McDonald’s. I think that exists in Mississippi, frankly, because that’s the only choices there are in Mississippi. But, it was very enlightening and eye opening early in kind of our GTM process to not only to go town by town, city by city, which was very much kind of the process of all the different state and local entities in these states.

But it gave us on the ground knowledge to hear directly from buyers. And there wasn’t a – this is like right after Covid was opening up. I mean, a state like Mississippi and Louisiana were some of the first to even be willing to have on sites. And so, it was a very great experience to get out there. And, you know, as much as you like to hypothesize what a go-to-market structure looks like when you’re actually out there, you’re meeting with people, whether virtually or in person, it really does. Just open up your mind to exactly how to go to market and where the challenges are.

7:42

Gary: That’s interesting, because, you know, that leads me to thinking about messaging. And yeah, clearly, for what we were, we were dealing with something that was different. No one had really done before creating a product that was delivering skills in VR headsets.

I mean, it was really cool. It was very forward looking. What were the key things that you heard from, you know, during those tours that allowed us to to really tighten up the messaging and the go to market? 

8:11

Chris: Yeah. So as an example, one that I thought was very insightful and Gary, you just mentioned this, but we were basically selling a product to deliver training and enablement for blue collar jobs.

And it was done through the delivery of virtual reality, which is awesome. A lot of fun. It was super, super new, super cool for people. So going out into the field, we knew really well that, like, people would really love our message and our product. They would love putting on a headset and seeing what it’s like to, weld, you know, something.

As an example. And we also believed pretty strongly that it would resonate with them on how to educate a younger buying class. I think back to what you don’t always know. And we would get out into the field, and we learned at the time that many of the biggest concerns that people had, around buying these solutions wasn’t even the solution itself.

It was really about, how do we fund this? Like, how do we actually get funding? So in that world it’s, you know, difficult to get funding if you’re a two-year technical college or your state or a local agency. but the other part of it, too, was their biggest problem in these workforce zones that really needed the most help was how do we actually get people to go back to work?

I mean, this is right at the height of the pandemic. Lots of people had deep fears about going into, you know, a manufacturing plant as an example. And or were getting paid, you know, in some cases to maybe, not work, you know, which is maybe a little controversial, but that was the direct feedback that we were hearing on the ground.

And so we were able to take that information, think about it, tailor our message and change for that. And ultimately, it changed a lot of how we went to market. It also led to us hiring an entire, you know, grant writing team and helping to apply for these federal grants to help find funding, which was very appealing to these buyers where we were coming not only with an amazing product and service, but we were coming with a solution for how they could actually go about funding it.

So all the way from the very first pitch to why we could help them all the way to here’s how you can even fund this, I think was very innovative from start to finish. 

10:12

Gary: And did that create a complexity for the buyers because we were dealing with the community colleges, we were dealing with the workforce development agencies, we were dealing with the funding.

How did that and how did you work with, you know, me and, and the marketing team to build what you needed in order to execute that in the field? 

10:33

Chris: I think the thing that we did well, not to toot our own horn is, but we had a very regular frequency where we didn’t miss a lot of time.

I think we were either texting or talking multiple times a week, which, you know, sometimes candidly, in sales and marketing leaders, they can go weeks, maybe months without really spending deep time. And we were forcing ourselves and holding ourselves accountable to meet frequently, share feedback from the field, and really have joint goals that were from the very inception, locked at the hip all the way from the board to the C-suite.

We were sitting down and reviewing collectively what the goals were, and there wasn’t a lot of misalignment where I think a lot of problems in, you know, marketing and sales come down to just misalignment on goals and what we’re all trying to achieve. 

11:14

Gary: it was great working with you on that because we were so aligned.

And you’re right, the communication was constant. And that, I think really helped us because we did have to pivot, you know, a handful of times. And if we didn’t have that level of close communication, it would have been a nightmare and a disaster. But that kept us really moving. And I think one of the key things you hit on was the metrics, you know, that we aligned on.

I’ve spoken with others on this podcast around hearing sales leaders focus on leads. How are you going to give us leads? And I think you and I never, ever had that conversation because what we focused on were outcome driven metrics.My OKRs were opportunities, qualified opportunities that your sales team could then go run after.

Tell me talk to me about, you know, about that and how we really got aligned on that because I think that was a big component of, of what kept us, you know, and our CEO all focused on the same things.

12:19 

Chris: You know, it’s such a great point. I thought about it a lot. And I’ve always had such great partnerships with my friends and colleagues in marketing.

But I think part of the reason why is because I’ve made it really clear and also, I think I’ve been a good partner for saying, hey, we’re in this together. Like our revenue number is the ultimate goal and trying to take the time and energy to step aside and talk more deeply about what are the ultimate targets and what are the ultimate goals.

And I think that makes you it helps lead you to making tradeoffs that sometimes are controversial. So an example of a controversial trade off that sometimes happens is should an SDR team live within sales or should it live within marketing? And at least in our case, I think there’s lots of ways to structure it. But as we took a step back and said, hey, look, what are we trying to accomplish?

Well, we’re trying to make sure that the marketing efforts and the funding and the deployment, the leads, all the things we’re doing are to ultimately make sure that the sales team is doing cold calling efforts and trying to do outreach. But we want to have this really crystal clear path of communication when something becomes an opportunity. And so we decided that ultimately that SDR team should live within marketing.

But that didn’t mean that I didn’t talk to the SDRs. I actually recruited some of the first SDRs, and they were, you know, in our office and working with us closely. But back to the, you know, truly in the line of the sand, I would think at night, hey, Gary needs to be able to have full control to coach and and help them do the great work that they need to do, where he’s not hampered by their ability to drive, qualified meetings.

And at the same time, I would go and have a coaching session with them as well. And so I think it was trying to just think about alignment at the company level and then, softer reporting line of who do you actually report into? But we’re all working really closely as a team. 

14:07

Gary: Yeah, I remember that, you know, the conversations we had to get started.

And I’m pretty sure some of the guys that you hired way back then are still there and just driving, you know, some real success with the business. But, I think where we ended up was we created that handoff and, you know, the SDRs and the AEs became that handshake and almost that forcing function of alignment between marketing and sales, because we didn’t pay the SDRs on creating meetings.

Anybody can create meetings that don’t necessarily go anywhere. And so what you and I aligned on was let’s get them targeted to create meetings, even though we weren’t paying them on that. What they were incentivized were meetings at the A’s would say, yep, I accept that as an opportunity. And so, you know, the SDR could argue they’re not in control.

But in a sense, they were, because it forced them to really work hand in hand with your AEs. and learn from them. We created that great mentor-mentee kind of relationship. 

Chris: Completely agree. Completely agree. 

Gary: Great. So you know, so what we had was that initial qualifying meeting, at Transfr. Can you talk about how that was structured and what we were aiming for, at that business?

15:25

Chris: Yeah, I would say that at least in that particular business, the handoff point was quite straightforward. It was truly about getting somebody to agree to a time to meet, giving a little bit of basic information, and then ultimately getting an account executive to have a conversation with them to go in a lot more depth. So this is a product where not a lot of complexity and also a lot of excitement.

So you have a publicly available list of people to reach out to. Every single community college in the country, state, local government, has phone numbers, emails posted on the website. There’s no need to pay for Zoominfo or some of these more expensive solutions. So it was a very clean, very clear ask. And so we felt like, hey, in that case, that should be a very marketing driven approach.

And building the assets, the materials, the things that we need to be there. And we deemed the handoff on a time schedule from that, you know, SDR, BDR, and then ultimately from an account executive taking it and and then after having met with them, agreed to continue to meet with them. So as long as the meeting happened and they continued to agree to meet with them, we would create an opportunity.

So we tried not to have too high of a definition of what an opportunity was, or too much complexity. Just to have a very clear way to measure what success ultimately look like. 

16:42

Gary: That’s cool. And what other approaches have you used, you know, for that, that, that still drive, that kind of, you know, alignment between the groups?

16:48

Chris: I mean, we’re talking about this a lot at my current organization, I mean, the pie is similarly concentrated and focused. It’s a lot bigger here at the company that I’m at now. But we have a very specific group of employers. We know we can basically sell to employers that are 2000 employees and larger across the U.S. These are very large enterprises.

They’re very complex. We play in the healthcare ecosystem, which means we also have brokers and consultants and partners that play some type of role within this ecosystem. So because this is much less about just going around and scheduling a meeting, but we have to develop partnerships and relationships. We’ve actually chosen to have a sales-led SDR team, and that has more to do with trying to go after strategic accounts, being very thoughtful about, you know, if you go to, you know, Georgia, in Atlanta, there’s one person that’s in charge of, you know, Coca Cola, you know, Delta Airlines and all major companies that are in that area that represent them to pick and choose their health plans and all healthcare solutions. So in our particular case, it’s a lot easier to align SDR, to individual teams and organizations to try to drive demand. But in that particular case, it’s just a lot more strategic and a lot more thought goes into how are we go and craft those relationships?

So there’s a lot of ways to do this. But I think, again, that’s why it’s so important to take a step back and to think about what it is that you’re ultimately trying to achieve and not just have one singular playbook. I think people and organizations that take one playbook that they had from one company and just try to go and copy and paste it into another, it’s usually a recipe for disaster.

18:24

Gary: At this point in the podcast, I ask my guests to share the best practices that they’ve learned throughout their career. So what would you say are the three most important qualities or considerations that you look for from your marketing peers to ensure that together you hit your revenue goals?

18:47

Chris: Yeah, it’s such a great question. I’ll try to consolidate it into three, but there might be more than three when you really think through it. So I’ll start with this one. I kind of mentioned this already, but I, I really believe in having joint OKRs and goals and really taking the revenue targets and walking backwards from that.

Yes, I’m a sales leader, but at the same time, I think, you know, if you think about a time where a revenue target is missed in those terrible moments where revenue targets missed and the CRO and the CFO aren’t very happy. But if you’re a marketing leader and you’re happy because you hit your MQL target, but nobody hit the revenue targets, nobody in the company is really happy and so, well, it’s really easy, especially as a marketer, to get excited and be artistic with sales assets and materials and great things, ultimately, if the company is not finding success collectively, you know you are a part of that team. And I think the best marketing leaders I’ve ever worked with, they really know the role of being a revenue leader, even if they don’t carry a direct quota, very well, and they’re very aligned with how they fit into the total, total ecosystem.

So I think that’s a really crucial one. I think another just kind of, you know, simple one is, you know, marketers tend to be really great at wanting to know what the market thinks and creating buyer personas. But depending upon the size of the organization, the maturity of the organization, they may not always be as apt to going to the best sellers and asking, what’s working in the sales process?

You know, some of the best sellers take the pitch deck that’s been built and they tear it up and they go and build their own or talk through it. And it can be really frustrating for a marketer who’s spent, you know, weeks to months on end building a great pitch deck. But in that insight, especially from your very best salespeople, there are great lessons to be learned.

And as a sales leader who’s very process oriented and very, you know, like I’m thinking about Salesforce and territories and how do I like, use my finance and ops background to go and build the perfect thing. I have to force myself sometimes to stop and say, what is it that’s working? And these people have a quota. They are trying to make money and they’re trying lots of things.

And so if somebody lands on something, they all find out about it. It starts to become knowledge. And so I think as a marketer, it’s really crucial that you’re watching what they’re doing. You’re seeing how they’re operating and trying to, you know, align with what they actually need to be the most successful on. That could be slides. It could be, you know, assets on the side.

It could be case studies. It could be a lot of different things. But I think that there is so much insight. I’ve also been a huge fan in the last 5 to 10 years of great technologies like Gong and Chorus and Avoma, and all these great platforms to record calls. And I’ve kind of lovingly referred to it as watching game film.

You know, if you’re a professional athlete, you spend more time watching game tape than you do playing the actual sport. And you listen to the great football players. Tom Brady, Peyton Manning, whoever. I mean, I watched a podcast of the night where Peyton Manning talked about how he built an entire, like, you know, virtual studio in his house to be able to watch highlights of, you know, Ray Lewis, you know, what he’s going to try to do.

So I just think there’s so much value that can be garnered and what an actual sales conversation looks like versus, you know, a hypothetical one. 

22:07

Gary: I agree with that 100%. I’ve been in sales, I’ve been a salesperson. And in those organizations where marketing was in the ivory tower is what I called it. And I did the same thing.

We ripped up the slide decks because what they gave us didn’t work. And so having… and you’re right, you know, I think at Transfr we looked at Gong videos and so on. And what I find works is testing with the sales organization. How is this messaging going to resonate? How would this work for you? What do you hear?

Right. That works because at the end of the day, your sales spends more time with customers and prospective customers than anybody else with the business. And it’s a crime not to leverage that knowledge, creating your messaging. And like you say, it can involve all the collateral, the website messaging. because you need people to look at the website before they’re ready to talk to sales.

So everything’s got to be aligned for that. What else you got for me? 

23:08

Chris: Yeah. No doubt. I think though, the last one, you know, it was really interesting because I worked at, you know, a company called ClickUp. And ClickUp is such an interesting company because they grew from almost nothing to, you know, hundreds of millions in revenue.

And, you know, there was a viral LinkedIn ad that came out recently where it was like they were doing a, you know, an HR spoof. And it I think it hit like 100 million views on TikTok. And they’re so creative and thoughtful about their marketing. But it’s funny because we actually spent over $10 million doing a Super Bowl ad while we were there, and it was a big expense.

So much time and energy went into it. And honestly, like, I wasn’t sure we should do in the first place, but it really fell on its face, didn’t work that well, didn’t drive that much value. And I mean, I’m no longer at ClickUp, but watching from afar, they did this TikTok, you know, video that probably cost a few hundred dollars, maybe max to, you know, go put together.

And they had an instant, you know, massive hit for, across TikTok that cost virtually nothing and got way more views and way more excitement and LinkedIn posts and, you know, reshare and everything. And the reason why I share that is, like, I’ve seen so many different versions of marketing and at least in that particular case, that wasn’t your MQL driven thing.

It wasn’t it wasn’t, you know, the exact, you know, perfect thing on the website. But ClickUp really has a very specific identity of how they’ve kind of built their brand, and they’ve driven a lot of the efforts on marketing to try to drive awareness for sales and, you know, for their particular product. It is not a B2C product, I wouldn’t call it that, but it’s pretty close to it.

It’s a B2B2C type of product where they’re trying to create virality. They’re trying to get people into the platform. They know, you know, 95% of users are going to be free users. So I think you just have to take a step back, walk into what your ICP looks like. What are you trying to facilitate? Talk to sales have really good joint goals, but I’ve seen so many different versions of how these playbooks can work, and I think it’s just crucial that you’re really thoughtful about how you’re going to market.

But I guess my final one, you asked for three. I think I’ve shared this a bunch of times, but marketing is a revenue function. You know, it’s to drive revenue and there’s lots of different ways to go do that, whether it’s, you know, what we built and what we what we created to drive revenue, that particular business to what I’m trying to do now of, you know, going across healthcare to what I helped build a ClickUp, which is this viral marketing machine, to try to get the world to know that ClickUp’s the best project, project management solution in the marketplace.

So, I just think you have to take a step back and be really thoughtful about what you’re trying to build and create it together. Sales and marketing should be best friends, and sometimes they weirdly are not as close. But I’ve had the good fortune of working with incredible marketers over the years who have made a huge impact on my ability to to sell and be successful.

25:51

Gary: Right, Chris, well, thank you so much for joining me today. And it’s really, really instructive on things that we need to consider as leaders to build that kind of alignment and build a structure that’s going to keep us swimming together in the swim lanes and not pointing fingers at each other, which, I think you and I really enjoyed that working together component, when we did.

For our viewers, I want to thank you for staying with the podcast today. Thank you for attending. And just remind everybody to subscribe to What Great Looks Like on YouTube. Don’t forget to like and comment and share and, be sure to join us for the next one.

Chris Adams, again, thank you so much for joining me today. 

Chris: No problem. Thanks, everybody. And thank you, Gary.