David Howland of Earnix on why marketing leaders leave startups

David Howland

Hello, Etgar. It's a pleasure and an honor to join you today.

David Howland

Sure, absolutely happy to. So I'm currently the CMO of Earnix. We are an Israeli-founded company that is multinational. We are considered more of a scaleup at this point in time, with significant success and growth. Earnix serves insurance and banking. We help with pricing, rating and underwriting. Essentially, we help insurance companies and banks align risk with price and product to build their customer base and customer satisfaction. This is my third time as a B2B SaaS CMO. I absolutely love the data-driven, data-centric approach that we now have as normal course in marketing. I've been at NASDAQ for over a decade helping to transform the brand and the business to really a pioneer in fintech, and prior to that I had a number of different roles on the nonprofit side, education, the art world, and started out as a cabinet maker back in the old days in Seattle.

David Howland

We're very fortunate today that we have the tools, the platforms, the processes available to us to be able to not just speak to goals and impact but to be able to support that through actual numbers. As I mentioned, I'm very data-centric, and I would expect that most CMOs would tell you the same. The ability for us today to be able to take a revenue number, to take a pipeline goal, and to look at the different campaigns and activities, the spend that's associated with those campaigns and various activities, and define how much intent, engagement, how much penetration within individual accounts based on the overall strategies are in play, allows us to be able to define very clearly: for X dollars USD, this has resulted in X amount of pipeline, and that pipeline has proceeded and closed at X rate. While we can't define every aspect of spend, we're actually at a point right now within Earnix where my team and I can define 85% of our overall budget spend and how that articulates directly to pipeline impact in year, but then also how we expect that pipeline to progress over the course of the next two, four and six quarters.

David Howland

It's a great question, and I don't think it's something that we'll ever truly solve for, in terms of nailing down the exact impact and metrics defined by that. I use a series of opportunities. There's case studies and anecdotes that we can always tell. There's an analyst coming up to me at a conference saying, "Wow, you guys are doing amazing things. The competition is scared." That's a great thing for the board to hear, but ultimately what does that mean and how does that relate to sales performance and revenue performance? I try to focus on the fact that everything we do, we want to tie it somehow to pipeline generation. So if there's thought leadership involved, we're thinking about how we're going to measure and track who's engaging with it and the impact that that might have. And what I found is that while we can't ever completely understand the impact, there is an opportunity for us to take it pretty much 90% of the way.

Analysts, we focus on: well, what's the research, how much are we appearing in research, and how is that research being digested by the market itself. We do win-loss analysis interviews after the fact so that we can tie back some of this as well. And then when it comes to the softness of it, what is our brand, what is the persona that we have in the market, ultimately that comes down to utilizing the sales team, their perspective, what they're hearing, and the fact that we've actually been able to move from "why would I trust Earnix with a mission-critical component of my revenue stack" as an insurance carrier, a bank, to "we know about you guys, we've been watching, we think there's some pretty amazing things you're doing, and we want to have a conversation." I've seen that shift take place over the last 3 years of activity of what we've been doing. As long as we can tie the bulk of what we're doing with the actual metrics, we can support that through defined case studies and quotable anecdotes, then I'm comfortable and the board is comfortable that we're doing the right things at the right time and seeing how we're actually engaging and growing the company.

David Howland

Well, before we get to the metrics, I think that the topic of trust is important not only with the market, but within your organization. You have to be transparent. You have to be fully accountable for everything that you and your teams are doing, whether you're the CMO or another leader or member of the company. And part of that is you can't oversell or overstate. You have to be honest about where there's impact that you're measuring and where there's impact that you believe from signals coming from the market.

As I'm thinking about the ability for us to put someone on stage, when I'm thinking about our LinkedIn presence, of course we can measure that, not clearly in terms of impressions in someone's feed, but a big part of this is we're building category leadership. And category leadership comes from being a leading voice. It comes from being an innovator, a disruptor, a transformer. And that category leadership is something that lifts the whole company. It's really hard to be able to put a metric to that. But again, when I see how our engagement levels in what we can measure is increasing, how the uptake in the number of meetings that our sales teams are able to schedule, these are all directly related and can be attributed, in a soft form, to the overall category leadership that we're pushing.

David Howland

So we've become intent-obsessed over the last couple of years, and the ability to measure signals and define the KPIs around that relates directly to what the individual from Gong had stated. In part of your question, we see the mentions we hear from the analysts, the increasing mentions we see on the PR side, not just the activity we are doing in terms of outbound but the number of interview requests coming inbound. Just even today, in the last 24 hours, I've had three new requests for interviews from French publications for our executive leadership, our CEO, specific to what we're doing. And these are all highly measurable. You can track these trends over time. And it all speaks to the growing presence, the growing share of voice and mind share within the markets that you serve.

David Howland

So the CEO, without question, is the one who is setting the tone, setting the strategy, who is really guiding the company both operationally and strategically into the next chapter, through the current and into the next. My role as CMO is to of course support that, but also I've got a responsibility as the CMO to bring in the inputs and the perspectives that are going to help shape that strategy. To put it into actual practice: a CEO has an executive team. They have very little time in the day, essentially, and are trying to maintain a broad and deep understanding of the company in a way that is exceptionally challenging to do from the top.

My role is to make sure that the CEO understands what's happening in the market, the trends in the market, performance that we're seeing, interactions with prospects, customers, and so on, to bring in research that's happening both from a PR perspective and the analyst perspective, from the overall thought leadership that's taking place, and to position the CEO so that they can go on stage, go to a media interview, and speak with authority, articulately, to any of the relevant topics. So that's part of it, but ultimately I view myself as the chief evangelist in the company. I want to be the one who is cheering from the sidelines and from the stage on behalf of the company and promoting the CEO as the unique industry thought leader, not just the leader of the company. Because ultimately, in most cases in which I've been an executive member of the team, the CEO has been the face of the company, and ultimately we need to make sure that the trust with the industry starts first and foremost with the trust and the authenticity of what the CEO is communicating, both externally and internally across the employee base.

David Howland

So obviously it starts with communication and alignment. I've entered into positions where the goal was to grow revenue for the company, grow the company. I've entered into roles where the goal was actually to prepare for an exit, to new investors, in a very short period of time. And those are two very different sets of marching orders. One is based on long-term growth with short-term impact. The other is focused specifically on repositioning the company, its strategy, even its product structure, so that the available TAM and future promise of growth is clearly established. So communication and alignment of expectations is where you have to start. But ultimately, my advice to CMOs and CEOs is you have to look at not just the next couple quarters, but you have to look at what's further out. What are you trying to accomplish?

I'm as interested today in 2027 and 2028 as I am in Q3 and Q4 of 2025. And that has to be understood and agreed upon, that this is the strategy and the approach, because ultimately if you want strong double-digit growth today and tomorrow, you have to be working on both simultaneously. I've left a position previously because of an overemphasis on shortcuts and guerrilla activities and the expectation of this, and I'm not against guerrilla activities, that's not a strategy, that's a tactic within a larger strategy that one has in place, because ultimately, again, there are no shortcuts. You have to put in the investment, the commitment, to be able to grow effectively. And what I've seen, again and again, is that startup situations and environments tend to focus on a hero mentality.

There's a hero sales, there's a hero marketing, and all activity is one individual through a cult of personality moving the needle, and that doesn't last. You have to focus on the bigger picture and you have to focus on scalability within the context of where you are. Are you trying to get to 5 million? Are you trying to get to 20? Are you trying to get to 50? The dynamic within which of those areas you fall is going to differ in terms of the strategy. But the fact that you have to move beyond shortcuts, guerrilla marketing, and a hero mentality is imperative, to have someone who can come in, implement, continue to learn and grow, and build further sophistication. What I'm able to do today at Earnix, by virtue of being there almost five years, versus what I was able to do after one or two years, is significantly different, in a very positive way, and that comes with time. It comes with further sophistication and understanding of how best to pivot, to adjust, and continue to evolve.

David Howland

Him or her, exactly. The questions that I'm asking, first and foremost, are around my need to understand their goals, and to push back. That's the other component of this that's very important. If there is a misalignment, or a lack of full agreement about how, and what the goals are, and how best to get there, then you have to be transparent and have an honest conversation about how to get there. I've had this again and again with different CEOs. You can say something, you can hear something, that doesn't mean that there's agreement. You have to really explore and set the table for future success. And what I'm focused on is there are moments in time. Your budget season is always a very fun time, and it should be. There should be very difficult conversations taking place around budget season, and when you're setting up the forecast for the following year. And if there is a lack of confidence that the expectations from a pipeline and revenue growth perspective exist, that there's a lack of ability to tie from one to the next, that conversation has to take place.

But I'm also interested always in continuing to refine my understanding of where the CEO is today in their thinking. Just because your CEO has shared with you their priorities on April 1, it doesn't mean that their priorities are still consistent in place on the 2nd of May, because that will change and it has to change. And the final thing I'll bring into this is it's always important to recognize that you don't know what the other person's world is. I have a very clear understanding of part of what my colleagues, whether it's people who report to me, whether it's other members of the leadership team, the CEO, members of the board, I have a clear understanding of a small part of their world, and the priorities, the inputs, the pressures that they're facing that I'm not aware of, are going to have an impact on their expectations of me. So I'm always trying to see around corners. What do I not know? How do I find the right question that's going to help me understand, so that I can pivot and adjust, or just provide support and expertise?

David Howland

Yes, I've seen this before, and it's interesting. I don't think it's any different when you're working for a $4 billion ARR company than when you're working for a $4 million ARR company. There's never enough budget. The expectations are always, let's just say, outsized based on the resources people spend that you have in place, and that pressure, I think it's a good pressure to have, you always want to be ambitious in your goals, and the expectations of each of us should be pretty steep.

On a side note, I believe that every day we prove ourselves, and every day the companies that we work for prove themselves to us, it's a symbiotic relationship, where I start with, to get specifically to addressing your question: start with value, start with the people, a segment that is most in need of your value, as you define it. It's not about total addressable market. It's about serviceable addressable market, and prioritizing that based on where you are, which stage, and the resources that you have to spend. It's not about low-hanging fruit and shortcuts. It's about understanding where you can have the most impact in the immediate term, by prioritizing effectively and growing from there. I don't think that it's a budget question. It's a strategy question. It's a question of understanding: okay, maybe we can't spend lots and lots of budget on events, but what we can do is invest in more direct personal engagement, personalized engagement, or digital display, in things that will help us get what we need from this very clearly defined audience and prioritized persona, and build from there.

David Howland

I'm going to take that not as an individual campaign, but in the direction of a fundamental shift of what we've done. A couple years ago, we moved to intent, and not just ABM but ABM to ABX, with an intent-centric approach, and that has really changed things for us, because as a B2B SaaS company serving large insurers and banks, we're not interested in MQLs. Leads are great, fine, an individual is interested, but we serve companies with buying committees of two dozen people and more, where there are hundreds of people who have potential impact on the deal. So I'm interested in qualifying accounts. I'm interested in building champions, building advocates, and making sure those who can influence a deal are positively engaged with us.

And that means that we're not just focused on one person or even 10, 20, 30 people, but I'm focused on trying to get broad and deep traction that could involve as many as hundreds, if not thousands, within large accounts. Usually it's a few hundred. And the campaigns that are most successful around that are the intent-based campaigns, driven based on where they are in their buying journey. Is there high intent representing significant interest around a purchase or decision stage? And how do we identify and direct personalized digital, and really outbound campaigns that, thanks to the tools we have in place, using GenAI to develop relevant content, we can provide the thought leadership, the engaging value drivers addressed to their specific needs, in order to build the overall engagement. And I know it's not an individual campaign, but for us, we have over 150 touches with an account before we even get a meeting, on average.

David Howland

Sure, absolutely, we want to learn from you. Our most successful tools, and a tool is just a tool: now we're using 6sense for intent, we're actually moving to HubSpot as our marketing automation platform, something I wish we'd actually done earlier. And we have a number of different sales platforms that we've started using, and Gong is probably the most valuable for us, just tying together the insights from the recordings between SDR, sales and prospects, pulling the transcripts and the insights out of that, connecting that to what we're seeing from an intent perspective in accounts, being able to pull all that together through dynamic digital display advertising, outbound through our email, LinkedIn targeting.

Just that alone is incredibly successful for us in engagement, in building out not just net new pipeline but also pipeline that is ultimately built off of cross-sell opportunities within existing customer accounts. We're fortunate in that events are very relevant in the insurance industry, but that's a very costly endeavor. So I am not skeptical about events, but very careful. You can spend far too much budget trying to be present on a consistent basis, whereas I can make sure that we are, through our strategy that we put in place, present consistently on other channels and platforms, and then present in the right way at the right events, that clearly identify us as a viable and compelling partner for our customers and prospects.

David Howland

So you want me to give away my trade secrets, is what you're saying.

David Howland

Relationships are key, without question. And again, focusing on where I am today, in a company that's serving insurance, people don't leave the insurance industry. People don't necessarily intend to join the insurance industry, but once they're there, they stay there for life. Relationship building is incredibly important, and right now I can pick up the phone, I can shoot off an email to dozens of different executives at different insurance companies, because we've hosted them in small, bespoke thought leadership environments that we've hosted. We're building relationships through very well-crafted bespoke engagements, but a big part of that is thought leadership. We're not bringing people together to sell. We're bringing people together so that they can hear each other, listen, and build and network within the industry. We are a facilitator on a grand scale. I took our annual customer event that we've been running in London for more than 10 years, and post-pandemic I turned that into an industry event that we happen to host. So we bring customers, thought leaders, prospects on stage. We also bring the customers of our competitors on stage, and the overall approach is we're inviting people to listen and share and network with each other, not to listen to us, and I think it's a very important dynamic to set in relationships, that pays tremendous dividends moving forward.

David Howland

I love this, it's been very successful and it's really helped. I can look at moments in time over the last four, just over four years, and there are moments in time that have been pivotal for us in our company from a marketing perspective, and one of those is the change of our annual event.

David Howland

This is an interesting one, because it's always good to recognize your mistakes. It's harder to verbalize your mistakes, but I think we have to own them and recognize that part of what we do is not "move fast and break things." What we need to do is move aggressively with eyes wide open and recognize that sometimes things don't work as we expected them to, and to do that self-retrospect, or introspection rather, and try to understand. One of the campaigns I come back to is the strategy that I tried to implement for conversational marketing at a previous company. We had a number of campaigns that we were trying to launch that were all based on supporting and built through conversational marketing, and I made the classic mistake of bringing in a tool, bringing in a platform, without the right resources, primarily time, and the proper infrastructure internally to be able to implement it effectively. So we ended up with a tool. We knew what we wanted to do.

We knew how to do it, but we weren't able to get there. I just had to eventually pull the plug on it, because I recognized that we were struggling to execute and that there was no path forward within which we would, or upon which we would be able to achieve our goals without significant harm to other activities. And even that being said, I wasn't confident that we'd ever reach our goals. So it comes back to: a tool is just a tool. Whenever you are implementing a new strategy, a campaign framework, the launch of a new campaign framework, you have to make sure that you not only have the strategy and the goals in place, but you have a clear line of sight in terms of what it's going to take, who needs to do what, and how you can get there. I consistently, as a leader, expect a tremendous amount of myself. It's one thing to expect of yourself, working long hours and many days. You have to also, though, respect the impact that that has on others, and be realistic about what's ahead.

David Howland

The top quality I'm looking for, by far, is curiosity. I want people who have a thirst and a hunger to grow, to learn, to expand, to evolve. Not someone who's going to come in with their expertise and think that this is where they can help us. I want someone to come in and be so curious about what we do and who we serve, and how they can learn and grow by virtue of the role. Number one. Number two is enthusiasm. You mentioned in our chat before we started that you want to have fun. You do this because you want to enjoy it and have fun in what you do. I don't know about you, but I'm pretty sure you're the same way.

You spend more time working with colleagues, new and existing, than you do with the other people in your life, your family, and potentially others. So I want to be around people who I enjoy being with. I want to have fun in the work with them. Even when times are tough, you have to be able to enjoy what you do. And that comes, in my mind, from the people you do it with. And then the third is humility. We have to work together effectively. And humility is something, recognizing, as I said earlier, you always need to see around corners because we don't know everything. We have no idea how exposed we are at any given point in time, and how much we actually need to grow and improve. So with humility comes that passion for constant learning through the curiosity, constant engagement through the enthusiasm, and constant re-evaluation through recognizing that we are always evolving and always improving.

David Howland

I think the biggest mistake comes back to something I mentioned before, more of a hero mentality, that the one thing that you're trying to do is going to pave the way to the growth that you're expecting to achieve, or you're vying to achieve. We're always building a foundation, whether it's at the very beginning or much further along in the journey, and the biggest mistake is thinking that if we just do this, we'll be successful. You have to step back and recognize that there are many ways to approach the market, and there is no one right answer.

But ultimately the guide that I think marketing teams or individuals in startups need to start with is: who are you trying to sell to, and why should they buy from you? And if you're starting from that point, any mistakes in terms of priorities, or thinking that you've got the answer through this one activity that's going to suddenly unlock everything, becomes much easier to navigate successfully. Because ultimately, if we don't understand the value we provide, if we don't understand the pain points of the person we're trying to help, or the industry we're trying to help, we don't put ourselves in their shoes. We're not going to be able to build something that is not just a single engagement today, but also that lasting trust that we're building, and presence in the market.

David Howland

I would say that it's setting a mandate that's not aligned with market signals. I've seen this again and again, for companies at many different stages, but I think it's especially prone, or a risk, for startups, where you have a founder or CEO who has come up with an idea, and they love their idea, but they need help from their marketing teams and others, their marketing leadership specifically, to be able to understand how to best translate that idea that they're so passionate about to the market. And oftentimes there is a significant misalignment, based on where that idea generated from, to the moment in time where you're trying to develop that product-market fit, that urgency, and that uniqueness.

David Howland

Never underestimate the importance of hiring the best talent. It is, in my mind, the single most important thing that we as leaders can do: hire the best and the brightest, and never accept anything but, and

David Howland

What happens after, for a CMO? The answer is, I don't know. I do know that the CMO role has shifted significantly, much more strategic. I am, and have been, for several companies now, deeply involved in all aspects of the company, from operations, strategy, product strategy, sales. I didn't even talk about the fact that I am so focused on go-to-market, not sales versus marketing, but go-to-market. The role itself has become something that is significantly expanded, and I actually think that the CMO is very well positioned as a future leader, as a CEO, even more so than ever before. So I think there's a lot of opportunities for CMOs that exist today that haven't existed before. The question is, and I hear it from a lot of my CMO colleagues: how do you move from being a scarred and damaged former CMO, to being a CMO who has been able to build and cultivate to become a leader in another context within the company, whether it's B2B SaaS, B2C, or otherwise.

David Howland

It's my pleasure, Etgar. I really enjoyed speaking with you and I look forward to networking down the road.