SELLEST OSAST
Everybody talks about GTM alignment. Sales, marketing, and customer success all working together around the customer. But actually making that happen changes how teams work together, and that’s where most alignment efforts quietly stall.
In this episode, Brian talks with Martha Mathers about where GTM alignment breaks down and what it really takes to fix it. Martha starts with pipeline first and top of funnel second, because pipeline is the one thing sales, marketing, and success can all agree on.
From there, she walks through mapping the journey from the customer’s side, what happened when a new sales team at OPEXUS kept jumping straight to the demo, what thousands of sales conversations taught her, and why she listens first (and says as little as she can) when she steps into a new role.
Here’s the thread running through the whole conversation: the problem you see when you walk in usually isn’t the whole problem.
About Martha MathersMartha Mathers is the CEO of TrueComp and a B2B marketing and go-to-market leader. Previously, she led marketing at Bloomberg Industry Group, BigTime Software, and OPEXUS. Her experience spans marketing, sales, customer growth, and leading cross-functional GTM teams.
Update (October 2026): Congratulations to Martha on becoming CEO of TrueComp! During our conversation, I asked what marketing leaders need to do to become CEOs. Now she’s made that move herself. Pretty awesome to see, and her advice is worth revisiting.
What We Cover- Why Martha starts with pipeline before top of funnel
- Getting sales, marketing, and customer success working around the customer journey
- What changes when you think beyond the funnel and include expansion
- Enablement as the connective tissue across GTM
- What Martha learned from listening to thousands of sales conversations
- Using AI to learn from more data and conversations, not just create more content
- Why experience can get in the way when a leader walks in thinking they already know the answer
- How much consensus it really takes to make change in a large company
- Making change a step at a time instead of trying to do everything at once
- What marketers need to learn outside of marketing if they want to eventually lead the business
- Pipeline gives sales, marketing, and success something they can agree on. Start there and work backward.
- Look at the journey from the customer’s side. That’s where the gaps between teams become easier to see.
- Listen to what customers and salespeople are actually saying. You may find that the story being told in the market isn’t the one marketing thinks it’s telling.
- Experience can create blind spots. Martha’s approach is to ask questions before assuming the answer that worked somewhere else will work here.
- Big companies take more consensus than you think. Knowing who needs to be involved is part of making the change.
- Change doesn’t have to happen all at once. Sometimes the better question is, “What is the change I can make this week?”
- “I’ve seen many leaders come in and assume by telling stories of everything they’ve done in the past, they will be able to fix the problem ahead of them.”
- “I listen first, ask a ton of questions, and share honestly as little as I can.”
- “Those are all different owners and different initiatives, but at the end of the day they all go back to the same account.”
- “We have a tendency to lead with the shiniest thing we can.”
- “I tend to value it, you know, more from an intelligence perspective than perhaps a content creation perspective.”
- “What is the change I can make this week?”
- Matt Heinz, whom Martha credits with the line “an MQL can’t buy you a beer”
- Gartner’s research on the B2B customer journey
- 00:00 Why GTM alignment breaks down
- 00:56 Where GTM alignment gets disconnected
- 02:33 Why pipeline should come before top of funnel
- 03:45 Aligning GTM around the customer journey
- 05:17 Expanding customer relationships after the sale
- 06:49 Why enablement is the connective tissue of GTM
- 10:30 What thousands of sales conversations can teach you
- 13:26 How AI can improve GTM alignment and enablement
- 15:53 The biggest mistake leaders make with GTM alignment
- 19:36 Stakeholder consensus and leading GTM change
- 23:34 How marketing leaders can prepare for the CEO role
Brian Carroll (00:01)
Welcome to the B2B Roundtable. I’m Brian Carroll, So everyone talks about GTM alignment. That’s from marketing, sales, customer success, all aligning around the customer. But actually making that happen changes how teams work together. And so the question I wanted to ask is: what really works? How do we actually make this happen in reality? And that’s why we have our guest today, Martha Mathers.
Now, Martha has been the head of marketing at companies from Bloomberg Industry Group to Big Time Software to OPEXUS And I wanted to talk with her because she understands this. And something I saw her talk about recently in a panel discussion on YouTube is that for her, they started by focusing on the pipeline first and top of the funnel second. So, Martha, welcome.
Martha Mathers (00:53)
Thank you so much, Brian. I’m really excited to be here.
Brian Carroll (00:56)
I wanted to ask you when you think about companies that you’ve worked with, where do you see GTM alignment getting the most disconnected?
Martha Mathers (01:05)
Yes, a great question. And I think it can happen in a couple different places. To your your first point, I think in terms of beginning with pipeline, I always think about where are those places where sales and marketing come together could be success as well, thinking about all of those combinations. But what is the thing that everybody cares about?
As a our friend Matt Heinz once said a long time ago, an MQL can’t buy you a beer. I believe that is that remains true. And now there are all kinds of debates about MQLs. But from a pipeline perspective, that is something that marketing can typically see their way easily to sales needs and must have in order to hit their number. And often with expansion motions, you have success thinking about quite a bit as well.
And so I always start there. Can I see where pipeline is coming from? Can I see how marketing is contributing to it? and just depending on where I’ve been in the stage of the company, OPEXUS was one without a go-to-market function. And so we started by building pipeline and thinking about how each capability would begin to execute against it.
I’ve been in other organizations that are bigger and at greater scale, but they don’t have that shared understanding. So just establishing that layer first of where does pipeline come from and where should it come from, and how can marketing contribute is is something I try and do as early as possible when moving into a new.
Brian Carroll (02:33)
Well, it as you were talking about thinking pipeline first and top of the funnel second, was there something that changed for you that made you look at it that way?
Martha Mathers (02:41)
Yeah, I I think there’s, you know, the debates that you can often have as a marketing leader with a head of sales around the quality of an MQL. And it at the end of the day, it’s finding that common currency and that that lingua franca in terms of I may be very excited about what’s happening on LinkedIn. And that matters a ton. Don’t don’t get me wrong there. That helps a ton in terms of brand awareness and reach and just how someone thinks about your company. and
As does every dollar and investment that brings a a new kind of contact or buying group in the door. but that was something that sales didn’t necessarily care about unless they’d maybe been on the ground at an event and had a good quality conversation. So by starting with pipeline and showing where a marketing investment actually turned into a quantity of dollars that maybe then turned into a quantity of dollars booked was something that we could hold hands around and agree on. And then once I had
that data layer, I can back my way into how to invest at different points in the funnel to get the pipeline that we need to grow the business.
Brian Carroll (03:45)
what’s it take to get sales, marketing, and the post sales teams all working around the buyer journey?
Martha Mathers (03:54)
Yeah, one thing that we did at OPEXUS was we really had a lot of missing capabilities when I started, as well as a couple of other executives. And for us, it was starting with a customer and starting with the customer journey. That’s something that you’ve you’ve heard, we’ve both heard Gartner talk about quite a bit over the years.
Brian Carroll (04:14)
Yes.
Martha Mathers (04:14)
and I had the I had the opportunity to do a good bit of research around too. It’s not mapping your sales and marketing and success activities. It’s
really considering that journey that the customer is is navigating throughout. And so I think if you can start there and think about what brings a new buyer to us, what engages them in a conversation, what makes them consider our solution, and then how do we get started and onboard someone? Those are all different owners and different initiatives, but at the end of the day they all go back to the same account.
And so I I always look at start with that buyer, map those key touch points, understand if you have the data to get underneath what’s happening at each and every one of those stages. And then those places where you can build that strong cross-functional coordination and handoff, I think become much more apparent, both in sharing information across teams, but also pinpointing the areas. for example, just a kind of quarterly business review where there could be sales marketing.
and success implications.
Brian Carroll (05:17)
Well, and after someone becomes a customer, this is an opportunity I hear a lot of companies miss, So do you have any advice or things you’ve learned that helps expand customer relationships?
Martha Mathers (05:31)
Yeah, most recently at one of the larger companies I’ve been with, we began the work to design and build out a customer marketing capability. I think often those expansion motions can be, you know, added onto demand gen float and all of a sudden you’re you’re pulling someone in a couple of different directions, starting with different buyers, depending on the size of the company that often
Brian Carroll (05:53)
Mm-hmm.
Martha Mathers (05:53)
can make sense as well as how the company grows.
But in this instance, we were struggling a little bit with some retention issues in one part of the business and had just a ton of new products to sell in another part of the business. And so we looked at, you know, how do how do we move away from thinking in funnel terms to thinking in bowtie terms? and what is the role that marketing can play from getting somebody onboarded to into the product and using the product? and then once you have those signals of strong health.
How do you start to lay the groundwork to grow that relationship? Can be at scale really easily if you if you have those kind of natural expansion points that are customer activity based, but it can also be a very sophisticated and maybe kind of detailed account-based motion in terms of thinking about exactly what the expansion path can and should look like for a specific account.
Brian Carroll (06:49)
And connecting all these pieces together, I’ve heard you say that enablement is the connective tissue around GTM. So what does great enablement look like?
Martha Mathers (07:02)
Yeah, I I have seen enablement live in all different all different places. And at the end of the day, I don’t think it really matters where they live because enablement really just like the customer has to work as that that connective tissue. You can build great messaging from a product standpoint. You can have all star reps and fantastic renewal conversations, but if that messaging never leads
leaves product marketing, if nobody is studying what those best reps are doing, those stories get a little bit lost along the way. And so I think of enablement as really taking the most valuable assets you have across all of all of GoToMarket, curating them, and figuring how how do we get these in people’s hands, how do we make them better? How do we use data to learn and iterate and ensure that we’re continuing to put the most powerful resources we have as a company.
in every go to market operator’s hand.
Brian Carroll (07:59)
So as you’ve had the experience over your career, can you maybe think of a story of where something wasn’t really working great and that you needed to work with the team to fix where there were misalignment or issues?
and where revenue is getting lost between the seams.
Martha Mathers (08:17)
One thing I go back to is you know, starting with the customer journey, so many of us see so much turnover across go to market, but in particular with sales teams. when I was at OPEXUS we had a relatively new sales team that we had brought on board and we were really trying to ramp up not only their company skills but their selling skills, and finding that we were quick to jump into the product, quick to jump into a demo, and so we
Started with that customer journey and worked backwards to say, how do we create the right plays for every stage from qualification to discovery to demo, all the way through into the post-sales experience? It was a a fun project to dive into because we needed data from all over the company. So, you know, helpful to have a good RevOps person doable even if you don’t, because we were looking at those touch points and those.
questions and what could we curate from all the conversations that we had to design a playbook that then informed our content strategy, helped with discovery questions, helped with the demo narrative that you would put in front of anybody all the way through to our retention plays. And so really impactful initiative in terms of aligning the whole go-to-mo-to-market motion from start to finish.
It allowed us to really pinpoint helpful things like exit signals when you’re moving from one stage to the next, and
Brian Carroll (09:39)
Mm.
Martha Mathers (09:40)
really start to learn and see a lot more about that customer journey and those key transition points. And actually, just to take it a little bit further, was a really helpful place at which we started to think about: hey, so many of these conversations that we’re having with existing customers point in one of three directions.
So that allowed us to kind of take what had been a new business focused effort and migrate it into an account expansion effort.
Brian Carroll (10:07)
Wow. And so as I’m listening to you, what what I’m hearing you did is you started with the data and that gave you the areas to focus. And and then from there you started listening and and talking to the frontline team to see where things were breaking down and then use that to help inform what you’re doing. Is that what what I’m understanding correctly?
Martha Mathers (10:28)
I I think well summarized, yes.
Brian Carroll (10:31)
Okay, very good. So one of the things you’ve talked about is you’ve listened to thousands of sales conversations. And this is something that is near and dear to my heart because I think this is something a lot of marketers we have the ability to listen, but I don’t know how much time you know spent there. So I wanted to say, what did that teach you? What did you learn?
Martha Mathers (10:55)
Yeah, I think we now are are lucky to have just so much great technology at our fingertips that can make that listening act that much more powerful. But you know, more more recently have spent a lot of time listening in terms of we want our ICP to look like this. How do those conversations stack up? and I think you can find, you know, multiple flavors of very helpful feedback, some of which is, wow.
I didn’t know we were positioning our product in this way. And that’s probably not exactly what we want to do because our competitor is stronger there. On the flip side, I think you can uncover gold in terms of customer pain points that you didn’t know necessarily were the the thing coming up as frequently as they were, and those talk tracks that your star reps use that you wish and hope you could curate and build into your pitch deck and every other reps talk track as well.
and so listening to all those conversations, there’s a little bit of good, bad, and ugly in terms of what do I want to take in scale? What is gold that needs to make its way back to product and into the hands of every single rep? And what are the things we need to course correct so that we
Brian Carroll (12:01)
Mm.
Martha Mathers (12:01)
can put together more compelling stories, more compelling content, and and position in a way that just sets us up for greater success.
Brian Carroll (12:11)
As you’ve done this, is there any surprising things, ahaas or counterintuitive things you took away from listening to all these conversations?
Martha Mathers (12:20)
It’s a great question. I think, you know, sometimes in in marketing and vice versa as well, it’s easy to say, you know, we’ve built this great story, but nobody is is sharing it or or telling it. And I think, you know, thinking about the reality of catching someone on the phone and having a quick 10 minute conversation, especially for an earlier career marketer, is a really impactful moment of just listening to yes, you can design the perfect.
Choreography, the perfect story, but your ability to deliver that isn’t always exactly what you want it to be. So in in terms of really uncovering one, how do you flex that narrative and and teach people that storytelling arc? If you can plant a narrative, you know, plant it here and there. but also all the way to wow, we really thought that we should lead with this, you know, AI-powered XYZ platform.
But every other competitor is doing that or no buyer cares about that. It’s really about the fact that you reduce risk by XYZ or you can increase revenue by a certain amount.
Brian Carroll (13:26)
It’s interesting as you talk about the what’s resonating with customers and hearing the words they say and how that can be applied back in. And you said the word AI and I was just wondering, you know, right now, where do you think there’s opportunities as as you think about this whole process of getting alignment? Where can AI help or where have you personally used it as is part of this enablement or to help you be more effective at getting alignment?
Between all these teams.
Martha Mathers (13:56)
Yeah. And maybe two different flavors to that in terms of internal
Brian Carroll (13:59)
Yeah.
Martha Mathers (14:00)
versus external. I think on the external side, we all, you know, as we innovate and build incredible new products, we have a tendency to lead with the shiniest thing we can. and I’ve worked with teams, you know, across multiple companies to say, but what is the thing, what is the problem the buyer is is struggling with? And I think that’s rarely they need AI.
Now on on the flip side of that, there are some in house legal buyers that I’ve worked with who have company mandates that they need to be using AI. and in that case, thinking about how you can position your solution in a way that solves their problem and helps them get work done can be impactful. So, you know, I I I think you just have to be careful not to introduce yourself just like everybody else in your category is and to figure out exactly how it can
it can impact impact your your buyer. On the from an internal perspective, I think it’s just incredible how much information that myself, my leaders can consume at scale. everything from you know quickly looking in Salesforce to be able to do a a quick and dirty win-loss analysis
To your point, curating the thousands of sales conversations with different types of buyers and and really having those insights to to dive more deeply into. I tend to value it, you know, more from an intelligence perspective than perhaps a content creation perspective.
Brian Carroll (15:28)
Mm-hmm.
Martha Mathers (15:29)
where I think it while I think it can be powerful there, I think it can also generate some not so great outcomes as well.
and so I tend to coach teams towards where can it make you smarter, where can it help you examine the data in new ways and perhaps give you a running start. but really, you know, encouraging individuals to put that human touch on on things that require more creative capacity.
Brian Carroll (15:53)
Yeah, I agree with what you’re saying in terms of from the content standpoint, avoiding the sameness and looking at how do we have our voice and do things that are uniquely human. And as you’re talking about the the research side of things, the enablement side of things, I was wondering as you’ve reflected back on all all the learnings you have, where do you think that companies make the biggest mistake when it comes to trying to get
Alignment.
Martha Mathers (16:22)
good question. I have to think about that one for a minute. I I think often there are hiring decisions made. You know, this person will be able to, you know, get alignment because they have done it before. and I’ve seen many leaders come in and assume by telling stories of everything they’ve done in the past, they will be able to fix the problem ahead of them.
Brian Carroll (16:46)
Hmm.
Martha Mathers (16:47)
I tend to personally think a lot more about why is the problem the way it is and push deep into kind of questions before I do anything. I I, you know, time creates lots of biases and hypotheses, and I really try and push those into the back of my head so that I can sit down perhaps with the head of sales just push to understand. Tell me about your experience with my team.
Tell me, you know, what the good, the bad, the ugly is. Help me understand what better would look like and what your team needs. And I think that often, one, it helps build trust just because you’re not racing in with a beautiful deck of here’s what the future will look like. but two, it I think it can help uncover education opportunities as well once you are ready to deliver that that roadshow deck as well.
And so I listen first, ask a ton of questions, and and share honestly as little as I can so that I can then take that information back and come back with something that that actually has a prayer of of solving the problem.
Brian Carroll (17:52)
Well, I appreciate you talked about looking at the evidence and really trying to understand what is the problem, you know, rather than trying to jump in as you’re talking about trying to fix it. And I think there’s something we all could take away from that because you know, maybe the problem you see isn’t actually the problem.
and I was wondering if you had any advice for someone who may not have done that. Maybe they’ve had a successful track record and they’re stepping in a new role. So
Is there any advice you’d want to give to peers who are listening out there on how they might be able to tackle this going forward?
Martha Mathers (18:26)
Yeah, if I if I think a little bit about a playbook, it’s you’ll probably walk into a lot of data. Some of it might be good data, some of it might be bad data, but take what you have and see what you can gather from it. And then I I really overinvest in building out you know, what are this, what’s the set of things that I would like to learn from this person? it could be where it could be completely unrelated to marketing in terms
Brian Carroll (18:48)
Mm-hmm.
Martha Mathers (18:49)
of where do your
customer conversations start.
What do you wish that you know had over the course of a discovery conversation? Where would you like to see more leads come from? why do our customers churn? you know, what have you what do you think of our competitor? But you could go in any direction. I tend to build out that detailed list and just think about I can probably learn something different from Brian than I can from this person, than I can from that person. Each of those things will give you a great angle on the business.
And then as you go and synthesize and think about the pieces you picked out from each person, each one of those has value. Not no
Brian Carroll (19:25)
Mm-hmm.
Martha Mathers (19:25)
one of those will be a hundred percent correct. And so that synthesis activity in terms of thinking about how to move forward is beyond the questions where I also spend a ton of time.
Brian Carroll (19:36)
Well, and as as I’m listening to you, I was wondering, looking back over your career, is there’s an area that you underestimated about making this kind of change and and doing it at a scale?
Martha Mathers (19:49)
That’s a great question. I think, you know, I’d I’ve had experiences at companies from 10 million up to many billions. and if I’m coming from more of a mid-market company to a larger one, I always underestimate the amount of consensus required to to kind of push things forward, which it probably seems obvious to anyone that’s only lived in large enterprise. but that
That whole act of ensuring you’ve identified all of the stakeholders who will have an opinion, who want to weigh in, and making the time for that. Everything from product naming to positioning a new solution to how you show up at an event can just have such a wild range of opinions that I think you can almost never overplan or over gather input thinking about the approach that you want to take.
Brian Carroll (20:43)
And I imagine and this is implied in what you’re saying, but this consensus also is about getting people on board with change and this whole
Martha Mathers (20:53)
Mm-hmm.
Brian Carroll (20:53)
notion of change management. Is there some things that you’ve taken away on what’s been effective and helping support change?
Martha Mathers (21:02)
I actually recently had one of my leaders point out to me something that I think actually is quite crucial to my approach. I tend to generally avoid a big bang type of change and look more for how can I incrementally build in the direction that I know that I need and want to go. And so I I think especially if you’re trying to quickly build credibility with a large team, thinking about, okay, what is the change I can make this week?
And then maybe, you
Brian Carroll (21:30)
Mm.
Martha Mathers (21:31)
know, another week later it’s another change. And I’ve applied that everywhere from how I’ve run leadership team meetings to how I’ve approached marketing planning, to how I’ve approached, you know, naming at a company like Bloomberg Industry Group and and thinking about just all the opinions and things like that that matter and are critical. And so to me it is, it is really, you know, how do you design a journey where every step of change, you know,
They feel it. They may not love it, but it it feels like a digestible move forward. And then all of a sudden you look back, you know, the the past six months and you can point to some massive moves that you’ve made for the business. Not doesn’t work for everybody, but that is, I think, an approach that I that I’ve used again and again.
Brian Carroll (22:17)
Yeah,
and as you were talking about, this is something people underestimate is how long it takes to drive change. And I really liked what you’re saying is what incremental changes can we make? How can we move forward and answer or ask that question? What’s the next best step?
What should we be focused on now? Is that what you’ve been saying?
Martha Mathers (22:39)
think that’s exactly right. And sometimes it is pretty thoughtful in terms of if I know the path from A to B, you know, exactly what that looks like, I try and break it down into the ten things that will take me there or the five things, depending on the the size of the change. I think big bang changes can make sense given the time and the place, but they can also be pretty disruptive in terms of the things that you need to get done day in and day out. And so
I the question I would, you know, guide many to is think about, you know, how quickly do you need to move? How big is the risk of disruption? and does the does the pain of the change, you know, outweigh it? And if it’s risky, thinking about how you can move a bit at a time can be, you know, a a much more practical approach in terms of just aligning your team and bringing them along with you and empowering them to drive small change as well.
Brian Carroll (23:35)
Well, I’ve loved talking with you. Martha, that as I’ve talked to a lot of different leaders, something about you that stands out to me is how you bring the strategic perspective to how you’re operating the business. And one of the things that I wanted to ask you about from a marketing leadership standpoint is the path to being the the top.
most leader in an organization, the CEO and B2B companies typically doesn’t happen by going through marketing. And I wanted to ask you, why do you think that is? And for those that may want to move into the topmost seat, what do they need to be doing differently to do that today?
Martha Mathers (24:15)
Yeah. I think, you know, if I think about that journey overall, one of the best experiences I’ve had in my career was managing sales and marketing together for a couple of years. it was great in terms of the customer’s experience as well as sales and marketing alignment, but it it also expanded my perspective. It was certainly helped by having that leadership seat. I don’t think that’s a must-have. That could just be
Ensuring you’re added to pipeline calls or forecast calls or diving deeply into the sales process. Similarly, if there is a retention priority at your company, how can marketing support? Many marketers spend a lot of time thinking about the product roadmap and you know how to what should be on it. Maybe try and gain some exposure to how to prioritize what goes on it and how it’s resourced and that sort of thing.
And then I would also say just being constantly curious from a financial perspective and understanding the financials of the business and exactly how and where sales and marketing spend fits in is another area that can help. So pushing if if I sum that up, looking
Brian Carroll (25:23)
Yes.
Martha Mathers (25:23)
for areas where you can expand your skill set, expand potentially your ownership through cross-functional initiatives. then
approaching the business with that constant curiosity would would be my my top takeaways.
Brian Carroll (25:37)
Well, thank you, Martha. I’ve loved this conversation. I’m really glad you were able to join us today.
Martha Mathers (25:43)
Thank you so much, Brian. It’s been a lot of fun.
Brian Carroll (25:46)
Thanks everyone for listening to the B2B roundtable. We’ll see you next time.
