The B2B Podcast Index
Index
All categories
MarketingSalesSaaSFinanceHROpsLeadershipCustomer SuccessAI & DataProductStartups & FoundersRevOpsEngineering & DevTools
MethodologySubmit
Best of:MarketingSalesSaaSFinanceHROpsLeadershipCustomer SuccessAI & DataProductStartups & FoundersRevOpsEngineering & DevTools
An independent project byFame
SearchBest episodesGuestsInsightsMethodologySubmit a podcast
Index/Marketing/Executive Conversations
Executive Conversations artwork

Running sales and marketing as one engine with Dan Chapman

Executive Conversations · 2025-08-05 · 23 min

0:00--:--

Dan Chapman entered DocNow as a sales hire but quickly realized the company needed a coordinated marketing function to fuel the pipeline. Finding only 1-2 MQLs monthly in HubSpot, he created a "North Star spreadsheet" of 20-30 marketing ideas, prioritized them ruthlessly, and executed across 60-90 days before seeing dramatic results. His unique position as VP of Sales and Marketing - owning both functions - eliminates the traditional silo between these teams and forces every investment decision through a revenue lens. Chapman discusses how he justifies brand-building activities (like clarifying DocNow's positioning and visual identity) by tying them to lead generation outcomes and CAC efficiency. He also addresses the shifting buyer behavior post-2020, where some buyers demand more hand-holding while others avoid salespeople entirely. His core philosophy: transparency with stakeholders, consistent one-on-one connection with sales teams, and ruthless focus on metrics like MQLs and pipeline contribution rather than vanity projects or tool optimization.

Key takeaways

  • →Starting with lead generation metrics (MQLs) as the primary indicator, then expanding to CAC efficiency and pipeline contribution, creates a measurable framework that justifies marketing spend to executives.
  • →Brand-building activities are easier to fund when you can demonstrate how they reduce market confusion or perception gaps that directly impact lead quality and conversion.
  • →The sales leader's perspective on marketing emphasizes relationship-building with the sales team, transparency about work in progress, and delivering on stated metrics rather than pursuing passion projects.
  • →Context-switching between sales and marketing roles becomes manageable when a clear company priority (e.g., revenue target) re-prioritizes work daily and CEO accountability reinforces focus.
  • →Marketers serving sales should understand their buyer's priorities deeply, hold regular meetings, maintain transparency about progress, and deliver against stated expectations rather than assumed needs.

Guests

Dan Chapman

Topics in this episode

Sales and marketing alignmentABM (Account-Based Marketing)HubSpotLead generationMQLs (Marketing Qualified Leads)Product launch strategyDocNowCAC (Customer Acquisition Cost) efficiencyBrand positioning and rebrandingOutbound email and calling

Questions this episode answers

How many leads was DocNow generating when Dan Chapman arrived?

DocNow was generating only 1-2 MQLs per month when Dan reviewed HubSpot on his first day, which prompted him to take on marketing responsibilities alongside his sales role.

What was Dan Chapman's first marketing strategy as a sales leader?

He created a "North Star spreadsheet" with 20-30 prioritized marketing ideas, executed them over 60-90 days, and saw dramatic metric improvements around day 90 by focusing primarily on lead generation.

How does Dan Chapman justify brand-building investments to executives?

He ties brand investments (like clarifying company name, visual identity, and market positioning) to lead generation impact by showing how they reduce buyer confusion and demonstrating that even one incremental opportunity pays for the investment.

How does owning both sales and marketing change the relationship between these functions?

It eliminates silos by allowing Dan to immediately resolve cross-team conflicts, explain decisions transparently, and ensure all work - whether brand or lead gen - connects directly to revenue outcomes.

What does Dan Chapman prioritize when managing competing demands between sales and marketing?

He defaults to revenue targets set by the CEO, reasoning that brand and marketing initiatives can wait if they're not directly advancing that priority, unless they demonstrably support it.

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Share of words spoken

  • Speaker A77%
  • Speaker B23%

Most-used words

marketing32sales31interesting11lead11trying10brand9side9team8different8important8start7building7started7first7back6market6

Episode notes

In this episode of Executive Conversations, Maeva Cifuentes speaks with Dan Chapman, VP of sales and marketing at DocNow. Dan tells the story of walking into a startup that was generating one or two MQLs a month, then building a 90-day lead-gen engine that lit up the entire pipeline. He explains how owning both sales and marketing forces a single-funnel mindset, why every project must prove its revenue impact fast, and how he justifies brand spend by showing that one closed deal covers the cost. Dan shares his “north star” spreadsheet of thirty ranked experiments, describes hiring creatives who can tie design to bookings, and details how constant calls with reps eliminate silos. He also digs into measuring success with CAC efficiency, balancing short-term pipeline with long-term credibility, and adapting to buyers who either want total handholding or zero contact. The conversation is a blueprint for making marketing accountable without killing creativity.

Full transcript

23 min

Transcribed and scored by The B2B Podcast Index.

Speaker A: Foreign.

Speaker B: Hey, everybody. Welcome back to another episode of Executive Conversations. I am your host, Maiva Cifuentes. In this podcast, I like to talk to go to market leaders about behind the scenes of marketing. So how are we getting buy in from our team, from our leaders? How are we doing internal marketing? And how has the role of marketing changed over the years? Um, I'm very excited today to talk to Dan Chapman, who is the VP of marketing at DocNow. And he has quite an interesting role because he is VP of sales and marketing. And I don't think I've had another person on this podcast yet who owns both of those. So this is going to be a really interesting conversation. Hi, Dan, how's it going? Hi.

Speaker A: It's going really well. Thank you.

Speaker B: Yeah. Um, I'm really excited to have you on. I know we've been trying to get this in the books for quite a while and we finally did it, so I'm really excited to dive into it with you. So you have a background in sales and then you came into marketing. Um, and I, I want to hear this kind of story about how that's been for you. And we'll start with, we'll start with that experience and then we can dive into the whole building this kind of sales and marketing plan, getting by and like how you manage the team and all those kind of things.

Speaker A: Yeah, thank you. Yeah, it's been a really fun, interesting journey. I've worked in mostly in, you know, officially sales roles, uh, most of my career. And, um, it's, you know, I've mostly worked for startups, small companies. So you kind of are involved in a lot of things that aren't your official job title per se. So I've always kind of dealt with marketing or helped with marketing, you know, events or ideas or, you know, different things. We were trying to do outreach, uh, you know, back in the day, a lot of the SDRs, ABM style marketing, a lot of that was also part of the sales thing. So, you know, things sort of got separated along the way. But, uh, a lot of the stuff that would be like traditional brand building and stuff like that haven't really been part of my wheelhouse. So those are the things I've really been learning lately. And it has been really interesting because, uh, because I come with that background. I think I started on the other end that most marketers would have started on when they would join a role. You know, I've seen like a lot of different types of playbooks and know, 90 day plans when you start a new Job and stuff. And usually a lot of those start with kind uh, of like, you know, assessing the brand and doing a bunch of stuff that I think is, is actually quite important and quite good. But I started with uh, lead generation, which is probably selfishly it was on the sales side and then I kind of worked backwards from there. Um, so. So yeah, it comes with a little bit of a different hat, but I've really, uh, tried to come at it and from a very humble perspective. Lots of learning. I try to meet with a lot of people, talk with people. I've been taking courses to learn as much as I can. And so I feel like I'm, I'm kind of getting my hands around it. But it's been, yeah, it's been unique.

Speaker B: I mean it's so interesting is the last conversations that I've had. Everyone is like, when I start the role, the first thing I need to do is connect with the sales leader and make sure the sales leader likes me because the sales leader is more, is considered more important. And so it's, it's just very interesting where like, do you have. I don't even know how to, how to frame this because yeah, a lot of the other marketers are like, I have to get on the sales leaders good side so that I'm doing things that's going to be more valued at the company.

Speaker A: Yeah.

Speaker B: Um, so like, what is, what is that like for you and your position as VP of sales and marketing? What, what's your relationship like with the CEO or the board or like the expectations of you?

Speaker A: I thought you were asking me how's my relationship with myself? And I was like, yeah, that's pretty, that's good.

Speaker B: That's for my other podcast.

Speaker A: That would be a good one. That would be a longer format. Um, so, um, it's, it's interesting because I, I have folks, uh, stakeholders on, well, uh, you know, people on the marketing and sales side. So sometimes let's say one of my, uh, team members on the sales side, a sales rep comes to me with something that they might, you know, complain or have a suggestion about marketing. They're like, oh, this didn't whatever. And then I'll say, well, that's also me. So then I'll pop over here and be like, well, let me fix that. Or is it valid? Or I'll be able to explain very clearly why we did something a certain way and you know, kind of talk through it, which I think is normal. But there might be usually those silos m. Might exist. Um, and then similarly, on the marketing side, when we're doing something, a lot of times people come to me with ideas and they were like, what if we spend the money and do, you know, insert project? And I'll say, well, let's, you know, how will that impact, you know, our overall vision, our overall goals, Sales, you know, that they go so hand in hand that you kind of can't do one without the other. And when I've interviewed people on the marketing side, particularly for, you know, roles with us and stuff, that's the part that's been really interesting is like the people that come to me with that bigger understanding of how it all works. Those people are very interesting to me. Uh, the folks that kind of come in and they just do one thing and they just can't kind of see, well, like, why are we building a brand? Like why, you know, like, what, what is the goal? And it's like, oh, it needs to be pretty or something. That's not really the goal. There's a bigger picture to all that. M. So then when you kind of go out from beyond that to, you know, uh, board members, CEO, you know, uh, you know, the C suite executives, um, a lot of times, depending on what is going on, I get a lot of um, glazed over looks on the actual tactical things we're doing. So like I want to do this type of advertising or SEO this or we need to do this branding project or whatever. But what they really care about, really care about are the results. So when I talk to those folks, I do, I like to give them kind of the highlights of what we're doing. Cause that a lot of times is the fun stuff. It's creative, it could be beautiful, it could be like really weird concepts that you distill down into something interesting. But at the end of the day they want to know, are you driving interest that will lead to funnel creation, that leads to revenue, you know, so you just, I don't, I don't really think you can get away from that unless you're just a totally different type of company or bigger or something.

Speaker B: I think you just can't get away with it anymore. But you have always come from that background of like everything I do has to lead to pipeline. So that came kind of naturally too. It, the company, um, Doc. Now, did they always have it? Was it always sales and marketing together or was there a shift where they said we need to get a sales guy to run marketing?

Speaker A: It was, it was a startup. I mean, uh, it was a startup before I joined. When I joined so there wasn't really, there wasn't a sales leader or a marketing leader. So there was a, you know, a small team of people that were all working together to do stuff. And they, they did a lot, uh, uh, an amazing amount before that. When I showed up, I just brought a lot of structure to the sales side. But my first, it was funny, my first day I had a meeting to just understand what they were doing. I, I knew a lot about them already, but I said, all right, let's talk about the, the marketing side. You know, like, how many, My first question was like, how many leads are getting generated for per month? And there wasn't a great answer. We went and looked in HubSpot and I pulled, I, uh, quickly did some reports and, and they were getting like one to two MQLs a month. And I was like, I think you need someone in marketing. Should I do that as well? And that's how I became head of sales and marketing.

Speaker B: Oh, wow. Okay.

Speaker A: Yeah. So it wasn't, it wasn't, I wasn't supposed to do marketing. But then I quickly realized that if we didn't do something in marketing, the sales side didn't matter. So I quickly jumped into marketing and then I spent the first 90 days creating an engine that would build lead generation engine.

Speaker B: Okay. So brave. He like, I applaud you doing that because you're just like, this needs to happen. I'm gonna make it happen. Yeah. Ah. So coming in from that perspective, where you're hired for sales initially, you have a sales background, and then you say this needs marketing. Obviously you've always worked very closely with marketing as well, so it's not like you're coming in with, with nothing. But.

Speaker A: Yeah.

Speaker B: To then build the pitch of, like, here's how I think we need to do marketing. Um, how. What was your experience with that, doing that?

Speaker A: It was, uh, it was really sort of, I mean, to be honest with you, it was a little bit scary. I, I, I basically sat down and just started just writing down all the ideas of things that I think thought could work, but I had no idea if they would actually work in this particular market and so forth. So I still have it. I called it like my North Star spreadsheet or whatever. And I just wrote down like, I think I had about 20 to 30 ideas. Um, I prioritized them and then I just was like, kind of showed everyone, everyone was like, cool, whatever. And then I just started executing, um, and it took about 60 to 90 days, so we didn't have a lot to show the first few months and then it was like literally on the 90 day mark, it just popped. Like it just like we just, it was a metrics just went off the charts and it started happening and then from there it was like tinkering, tweaking, trying different stuff and it was really cool to watch. And then a year and a half in or so it was like everything got ratcheted up. We got to do more. So then it's been like, how do we do more? And then it was again another kind of scary moment because it's like we've been consistently at uh, kind of this mark and then it's like, how do we get to this next mark? Well, let's try a bunch of stuff. You see what I've been seeing, what works and now it seems like it's popping again, you know, beyond what we were doing before. So that's exciting. So yeah, that's my simple but honest strategy.

Speaker B: Sounds like a winning one. You mentioned prioritization. I'm curious, do you have, do you use any kind of prioritization framework or how do you do that?

Speaker A: Yeah, a lot of it, um, you know, it's changed. At first it was really tactical. It was all about uh, it was literally about lead generation. So I would do, you know, whatever five to 10 projects, have them all running and then I would see what the results were and report on those and say, say I thought this would do more. Can I tweak it, do something or I'm going to abandon this, this project, uh, and then try something else. Um, so really it was like MQLs were my number one indicator. And then I started looking at other things. Um, from there we've been like looking, um, I mean we're starting to look at things like CAC efficiency and like trying to look at different ways that we can measure marketing in a more, you know, kind of more of an executive level way to make sure we're not like over under investing and doing different things. And frankly some of the stuff we've had to do. I haven't had a very good framework. I've just, I mean some of the things, to be honest with you, I've just sort of like steamrolled and said we're doing this, it's going to cost this much, roughly try and stop me, you know, kind of thing. And uh, I just start doing it. And then a few things, uh, I did get, you know, like with our team we decided to, you know, can a few things that I thought could be helpful. But in Retrospect, I don't know if they would have been great or not. Uh, yeah, I'll never know. But like, the, um, you know, there's hiring decisions you have to make along the way. You have to decide, like, I have this much money, what, where am I going to put it? When you're in, in control of it that way, it makes it to where it's like you have to really back it up. Like, why did you spend X amount of dollars on this thing?

Speaker B: Yeah.

Speaker A: And it didn't turn into anything. Then you look like didn't do your job well. So it's, uh, it's a little, there's some pressure there.

Speaker B: And it's also interesting that you mentioned, like a big focus of what you're doing is brand building.

Speaker A: Yeah.

Speaker B: Because in a lot of the conversations I've been having, and what we're seeing on LinkedIn is a lot of the marketers are saying, I want to do brand building, but, you know, I'm not getting budget for it. And the sales team is getting budget for all this lead gen and sales stuff. But you as a sales leader saying, I want to invest in brand building. Did you get any pushback?

Speaker A: Some, um, I think the way, yes. Some because of other, you know, like, larger financial goals for the company. So there's always like a bit of a balance there. But I really think it's important and I would love to. I mean, this is a good discussion to have with anyone. Like, the why is like the most important thing. So whenever I pitch something, I always have a reason, try to have a reason why we're doing this, you know, And I do, I do try to tie it back to lead generation. So some of the things that we were doing were like our name, you know, like, it's as simple as, like, our name is sort of not working great and there's some confusion in the market about who we are. And there's other companies that are very, that are called like, us and does it make sense? So some of those conversations are, uh, fairly logical. So it's like, can I change the name to this where it makes more sense. I thought about changing the name to something totally crazy, like, let me come up with a new word for the company. And then I realized if I just simplify this and solidify this name, that is a brand building activity that's not very sexy, but it's actually like, it's actually quite good. You have a brand that I think is very creative and unique and it sticks in your mind. But that's something you might sit around sometimes and be like, all right, what if I change it to fc? Or what if I just. What if it's just a cat or something? You know, those things. But why, why would you, why would you take the time, energy, money to do that? But then when you start putting like, larger numbers behind, hiring graphic designers and artists and this and that, and changing the color palette and all this stuff, that can be a little harder to sell until you put it up next to what you currently have. If you say, here's what it looks like today. This is how we're. And you know, I did some surveys. How are we being perceived in the market? I had plenty of people come to us and look at our website and say, you don't look like a tech company. I can't understand what you do. It's, uh, not clear to me what it is that you're actually providing. All these are like very basic things that you say. I think we should change these things and our perception will go up in the market that we're of, uh, who we are. And then if you have competitors and put it there so you kind of have to build the case and it doesn't always work. But if you tie it back to like, if we do this and we spend X amount of dollars and that leads to one opportunity that pays for itself, would that be worth it? The bar is fairly low, you know, that kind of thing.

Speaker B: Now, as somebody leading sales and marketing, do you think, uh, that it should be one person managing it? Like, are you, how are you managing the context switching and all of those kind of things?

Speaker A: It's. Oh my gosh, what a great question. Um, I think there's pros and cons, and I think it, it, it really helps to have, uh, folks in your team that keep you in check a little bit. Uh, I sometimes go a little too off the marketing end. And you know, people are like, you're look, you know, basically like you're looking at swatches. What are you doing? And it's like, okay, m a little over here. And then like, you know, I have a, I work for a really fantastic, uh, CEO. He's a, he's a great guy. He's a good friend of, of mine. And occasionally he'll be like, how are we doing on revenue this month? And I'll go and look and I'll be like, m, we're a little behind. He's like, what do you think? I'm going to go work on that. And it's just like, it's an easy shift to say, like, you know, again, what is your priority? Because if your priority is revenue, uh, and then versus looking at swatches, it can be really easy to say, if I can get to the revenue part, then I'll look at swatches.

Speaker B: Yeah.

Speaker A: Sometimes you might say looking at these things might lead to revenue. So maybe that is a priority. But, I mean, that's how I do it. It's like today we did a really big product launch for us anyways. It was like a very organized, uh, way of doing it, which is before we've done it more chaotically. And I spent a lot of time on it, not because I just am really concerned with it being beautiful. It's like, this will lead to lead generation, that will lead to revenue. So it's prioritized. If it was just like an exercise and like, this is fun for me, I would probably go do something. Go focus on something.

Speaker B: Yes. In the two years that you've been in Doc now, um, do you feel like this, the role has changed, especially with everything that's been going on in the last two years?

Speaker A: Yeah, yeah, it has. Uh, I don't. That's a great question. I don't know if I have a very succinct answer for you. The way people want to interact with the brand and salespeople, I can feel it very much shifting. Um, sometimes, weirdly, people seem to want more hand holding, and other people just don't. Don't want to talk to anybody. So there's this odd balance I'm trying to figure out. Um, and, you know, I think everyone's trying to do more with less, but then also with some really unique tools that are coming out. You know, a lot of the AI stuff is really exciting to work with, uh, in many different ways. Um, but I think fundamentally, um, we're still talking about a lot of the same stuff. So the roles are shifting a little bit in our group because of my joint, you know, dual role. It's very focused on this leads to this, leads to this. And I think we're trying to drive that through the whole company, honestly. So I think that's what kind of the CEO is supposed to do, is say, hey, folks, our number one thing is X. And then everyone in the company should be saying, okay, if I'm the cfo, how do I help with X? You know, not I want to go work on a payroll project. No, no. How do you get to X?

Speaker B: That's actually, I mean, priority prioritization. And then you following that, I'VE also been hearing this too, that it's trending, that fewer and fewer buyers want to actually talk to a salesperson.

Speaker A: It seems to be that way in our market because we work with a lot of, uh, providers, doctors and nurses and stuff. They are very much like phone people. So some of them don't, but a lot of them still really, really want. They don't want to read something, they just want to pick up the phone while they're driving and talk about it. So it's a little bit unique for us, but I can easily see that in almost any other space that, that's the, that's the trend.

Speaker B: Okay, so last question for you. Um, you used to work with marketing as a salesperson. Now you're both. Now that you've put yourself in the shoes of how does marketing support sales? How do I put this? Do you have words of wisdom for, for marketers who are not able to be the salesperson but are trying to serve sales the best they can? Do you have any words of wisdom to, to share with them or like, what your biggest lessons were that you think can be transferred to others?

Speaker A: Yeah, uh, for sure. Um, so I think at the end of the day, you, you, um, it's good to have a good relationship. I think that goes a long way. So I, you know, I always think like, having, being able to pick up the phone, having regular meetings, and making sure you really understand who you're trying to serve is really important and that can get missed. You, you go work in a silo and you think you're doing something great, but the person you're, if you're trying to serve the sales team or the sales leadership, then you should be like, with them, uh, you know, on a, you know, talking to them often, uh, and being very transparent about what you're working on and doing and making sure that translates into what they want. And then it's a, it's genuinely, it's a relentless, you know, metrics driven work towards those goals. Um, I just can't impress enough on how, like sometimes we work on things that we think, you know, that maybe we really have a passion for, but other people that really matter a lot don't care that you did that thing.

Speaker B: Yeah.

Speaker A: If you just delivered the thing that they wanted, you would be a rock star in their eyes. So it's really important to zone in on, like, hey, what is this person wanting of, uh, me and how do I do that thing?

Speaker B: I think that's everything that's actually so important. I have seen that where people are working on projects where they're like, isn't this awesome? And then you're like, yeah, but what about the thing I told you it was important.

Speaker A: That's what I tell, like, you know, folks on that work, you know, that have deliverables for me, I tell them the same thing. I try to be very transparent. I say, like, you know, if you're doing outbound email and calling for me or something, like, what might. What. What should our expectations be? Okay, it's this number. Okay, well, at the end of the month, I don't want to hear about all the HubSpot optimizations you did. Like, that's cool, and that could be valuable, but I really want to see, like, did you get this many MQLs or not? And if not, let's talk about how we can make that happen. Or do we have, uh, something else, you know, going on? And if not, we spend all our time talking about HubSpot or Salesforce or whatever, and meanwhile, the problem still persists.

Speaker B: Yeah, um, Dan, this feels like a good place to wrap it up. This has been great. Thank you so much for talking to me today.

Speaker A: Thank you. And thanks for the great questions. It's great talking to you too.

Speaker B: Yeah. And, um, can I tell people to connect with you on, um, LinkedIn or is there someone better?

Speaker A: Yeah, LinkedIn's good. Uh, yeah, LinkedIn's probably the easiest. Um, easy to find and happy to connect with anyone on there and always, always happy to share insights and learn more. So feel free.

Speaker B: Love it. If those listening or watching enjoyed this episode, please remember to share. Give it a like. Let me and Dan know that you enjoyed the episode. I do love to hear back from the listeners and. And, uh, we will see you next time. Goodbye.

Related episodes across the Index

Other episodes covering the same guests and topics, from across The B2B Podcast Index.

  • How to Hire a VP of RevOpsGTM Science · on HubSpot83 / 100
  • The End of Software as We Know It: How AI Agents Are Rewriting HR, SaaS, and Organizational DesignAI First with Adam and Andy · on HubSpot81 / 100
  • From the moshpit to the marketing plan | What a decade in the music business taught Jason Miller about attention in B2BTrust & Influence in B2B · on HubSpot81 / 100
  • Ep. 280: Mid-Year Marketing Check In - Same Tactics, New SteroidsOut of the Hourglass · on Lead generation80 / 100
  • Why Your Marketing Problem Is Not the Real Problem | Maylee Jacob, Maylee Jacob MarketingStraight To Voicemail · on Sales and marketing alignment79 / 100
  • John Suarez on How Businesses Should Actually Use AI Without Losing Human JudgementMarketing for SMEs · on HubSpot78 / 100

More from Executive Conversations

All episodes →
  • From IPO prep to mid-market leadership: hard lessons in accountability with Rob Freedman63 / 100
  • CMO-to-CRO isn’t capitulation with Kathleen Booth
  • Building tech-savvy marketing leadership with Rick Egan
  • Leading without authority with Igor Kranjcec
  • Aligning marketing, sales and CS with Janet Jaiswal
Explore the best B2B Marketing podcasts →
All Executive Conversations episodes →