Strategic Hiring, Measurement, and Cross-Functional Success with Jason Lyman of Customer.io

ABOUT THE GUEST

As the Chief Marketing Officer at Customer.io, Jason Lyman is responsible for product marketing, demand generation, growth marketing, content marketing, PR/AR, creative, and marketing operations. He has over a decade of B2B SaaS industry experience, scaling marketing functions globally and holding leadership positions at companies like Dropbox, Podium, Ethos, and BetterCloud. He holds an MBA from the University of California, Berkeley. In his downtime, he enjoys attending as many live music shows as possible, spending time with his family, and is a dedicated Bay Area sports fan.

EPISODE SUMMARY

On this episode of The Next CMO Podcast, Scott sits down with Jason Lyman, a three-time head of marketing with experience leading large marketing teams at companies like Customer.io, Ethos, BetterCloud, and Dropbox. Together, they dive into the complexities of scaling marketing teams, navigating the talent gap, and overcoming challenges CMOs face during high-growth phases. Jason shares his approach to prioritizing hires, fostering cross-functional collaboration, and maintaining messaging consistency. Tune in for actionable insights on balancing strategic alignment with operational efficiency and the importance of driving value for the business in a holistic, data-driven way.

TRANSCRIPT

Introduction
I am your host, Scott Todaro, and I’m here with Jason Lyman. I’m really excited to have Jason here for a lot of reasons. One, because I had a conversation with him prior to this, and he’s a good guy. This is going to be a lot of fun.

But also, on top of it, he’s got a lot of experience running fairly large marketing teams. One of the problems I hear over and over again talking to CMOs is they struggle hiring the right people, scaling their team the right way, prioritizing things. So when Jason reached out and said, “I want to be part of the podcast,” and told me what he wanted to talk about, I said, “We’ve got to get you on.”

Now, Jason’s got a ton of experience. He’s a three-time head of marketing.

He’s worked at great companies: Customer.io, Ethos, BetterCloud.

These are all great companies. They’re doing exceptionally well, and you had an opportunity to scale all those marketing teams. So I think as we’re going through our discussion today, you’re going to pick up a lot of great points on things like prioritizing, who to hire, how to hire, what to look for in people, and how to maintain consistency with your team as you add more people because we all know, unfortunately, marketing doesn’t scale in a linear fashion with sales. So it’s always very difficult to figure out what is that right next touch.

So, without any further ado, I’m going to turn it over to Jason. But the first question I wanted to ask is just how do you approach this? How do you set this up? I mean, can you share your experience in scaling any of the teams or all of them all at once?

Or was there a formula that you used?

Early Career and First Scaling Experience
Yeah. Absolutely.

I was really lucky that I had a chance to join a high-growth startup pretty early in my career. Just a little bit of context, I spent a few years as a strategy consultant, did a lot of work for technology companies, and realized that’s where I wanted to focus going forward. So I went back to grad school, did a couple of years at Berkeley, and actually started out at a really big company, Microsoft.

I worked in the Office 365 group up there. Pretty quickly, I realized that I’m not a big company guy. So I started looking for that next step after I felt like I had learned what I needed to learn. And after two years, I was lucky enough to join Dropbox pretty early.

When I joined, the marketing team was maybe ten or eleven people, and I was the second product marketer. Over the course of the four and a half years that I was there, that marketing team scaled to 120 people, and I was managing a team of 20 product marketers and seven campaign managers. It was a really amazing ride where I was able to see different phases of growth, develop a ton of best practices, and kind of caught the bug. Because for me, the challenges motivated me, and that’s what got me excited going into work every day.

Since that experience, I really sought out those roles, and you alluded to some of the companies that I’ve been at subsequently.

Key Themes and Challenges in Scaling Teams
One thing I noticed was there’s a lot of consistency as far as the key challenges I was facing while scaling these teams. So for me, the themes that kept coming up were how do you prioritize the right way? How do you get the right people to join your team and make sure you’re finding the right backgrounds that are going to be a fit? How do you maintain cross-functional alignment with key stakeholders and make sure you’re all swimming in the same direction?

And how do you maintain consistency in storytelling and messaging? These were all consistent challenges, and I think it’s important to have a point of view and a mental model you can use when faced with those situations.

Prioritization and Goal Alignment
Very good. I mean, it’s interesting when we start talking about prioritization.

I think you can probably provide some advice to early-stage heads of marketing. Where do you look at the starting point, and how do you prioritize the order of the types of hires you want to bring into your company?

Yeah. I think first and foremost, make sure you’re clear around what your company’s top priorities are, and ensure that you then have clear alignment on how marketing is going to support those initiatives. Because in the end, that’s how value is going to be perceived by your CEO and the broader executive team. So as you look at that, start to focus around the big rocks that you want to deliver as a CMO.

Because I think in the end, it’s so easy to get distracted by ad hoc requests. You don’t want to be subservient to the person who’s banging on the table the loudest. You always want to stay focused on how you can deliver the most value. By having those big rocks in place, you maximize the return on the resources available to you and the investment dollars you’re going to put to work.

Then you need to ensure you have strong measurement in place for those big rocks. Because in the end, you need to tell a story about the impact you’re delivering. So measurement is crucial as you try to figure out where to double down or pivot, and you need that signal. Being a CMO is hard enough, so you need these gauges in place to help you be reactive when needed.

The last thing I’ll say is to keep a “less is more” mindset. A lot of times, you’ll have more good ideas than you have the time, budget, and energy to pursue. I think of myself almost like an investor, where I have a limited amount of dollars to put to work. You have to be opinionated about which projects or marketing initiatives will drive the biggest upside. Once you have that in place, it translates into these bigger decisions about who to hire and where to prioritize budget to deliver impact.

Working Cross-Functionally and Building Relationships
I couldn’t agree with you more. In fact, we talk about it on this podcast all the time: starting with goals and then doing measurement. A lot of CMOs struggle with defining their goals. One thing I liked that you talked about with the big rocks is looking at your company goals and making sure you’re meeting what the company demands are, what you’ve set as an executive team, and then working with cross-functional teams. Tell me about working with cross-functional teams, because I’m sure as you’re going through the hiring process, you’re getting feedback from the head of sales, the CFO.

How do you prioritize and work with cross-functional teams to ensure you’re satisfying all requirements?

Yeah. I mean, I think you nailed it in that collaboration is key, especially when you’re going through this high-growth phase. One thing you have to be comfortable with as a CMO is that change is inevitable. It’s important to have clear communication and touchpoints with your key stakeholders.

It’s also important that the CMO isn’t the primary point of contact for everything going on inside the marketing organization. So it’s essential to distribute that communication and ownership across all the different layers.

I almost think about it as a cake where, as the CMO, you’re the frosting and you’re interacting with your peers—your head of sales, head of product, CEO, CFO. But you also need other layers in the cake to be aligned. You have the director running your demand gen or your leader running product marketing. They need to be interacting with their peers in their respective functions. Then your individual contributors need to know their cross-functional partners. While they might not have formal touchpoints, they should know who to reach out to, who to build relationships with. One of the best ways to do that is to integrate into the existing rhythms of those cross-functional partners.

In the end, they’re always going to default or prioritize communication with their direct reports. But success comes when you’re proactive, getting ahead of what needs to be done, and having visibility. For example, when I was at Dropbox and Podium, I was leading the product marketing function. I was a weekly participant in the product leads meeting and a member of the extended leadership team for the sales organization.

In those meetings, they sometimes discussed topics not applicable to me, but the 20 to 30 percent that did apply were hugely impactful. It allowed me to be more agile and adjust as needed. In turn, they saw that responsiveness, which strengthened the relationship and justified my interactions at that more granular level. I encourage people to snap into the consistent operating motion of cross-functional partners for more success in building relationships, communicating more effectively, and adapting as needed.

Hiring and Developing the Right Team
And it’s interesting. You mentioned structuring and delegating authority. When you talked about layers of a cake, it made me hungry but also sounded very delicious, so we should talk more about it.

Because one of the things I hear from CMOs is, “Am I going to be able to hire the right people underneath me?” Hiring is challenging these days. There’s a talent gap. Good talent costs a lot, and in B2B marketing, budgets have been cut for hiring top talent under the CMO. This puts more pressure on the CMO to make all the decisions, to be that liaison with other groups, and that becomes daunting. So how do you find the right people, prioritize those roles, and determine which roles get that responsibility and can network with the organization to get things done?

Yeah. I think there are a few principles I’ve had success with. First, make sure you’re hiring based on the maturity of the business. If you’re an early-stage business or smaller, you need people who are adaptable and flexible. I think of these people as Swiss army knives; they may not have deep experience, but a lot of what you’re doing is straightforward. You need someone scrappy, comfortable with ambiguity.

Those people deliver significant ROI for the business. So when resources are tight, they’re the most effective.

However, you’ll eventually hit an inflection point where you have to switch from generalist to specialist. This isn’t the same for every company, so it’s hard to say when, but typically it’s when the problems become more sophisticated, and you need someone with a wealth of knowledge who’s focused on a specific area. That’s an essential insight to constantly assess.

When you start hiring specialists, focus on people who have been specialists at that stage in the company’s lifecycle. One issue I’ve seen often is leaders get excited about someone with a big brand—they’ve worked at a market leader in your space, probably a company of a thousand, ten thousand, or a hundred thousand people. But they only know how to operate in that stage of the business. So if they’re used to unlimited budgets and resources, they might struggle in a high-growth situation.

And vice versa, it doesn’t work if you bring someone who’s only been a Swiss army knife into a structured environment. It’s essential not to get distracted by flashy brands or someone with a pedigree misaligned with where you are in the company’s stage. You need people who know their bread and butter. For some, that’s early-stage. For others, it’s mid-stage high growth or big company experience. Looking through this hiring lens will help avoid bringing in people who can’t adapt to the business’s needs. It gives you conviction they’ll succeed in the environment you’re operating in.

Transitioning from Generalists to Specialists and Maintaining Morale
That’s incredible. But I want to focus on something specific you said that I think is the biggest challenge, and I’d love to hear if you were able to overcome it or if you just dealt with it like we all do. You talked about moving from generalist to specialist.

The question is, you’ve got generalists who have been doing lots of things at your company, know the products well, and maybe were there at the beginning.

And now you’re moving to specialists who know how to do one thing. Right? We know that with specialists, especially new people coming in, you talked about message consistency.

Right?

That gets hammered. Right? You have new people coming in who only know one thing, and you have generalists whose roles get minimized, and you have to repurpose them into specialized roles. Their morale usually starts to drop. How do you get generalists with more control and power to accept a lesser role, while bringing in new people who, initially, don’t add much value until they understand the business? And then how do you ensure message consistency across functions?

That, I think, is the biggest challenge in growth I’ve found, but I’d love to hear if you’ve tackled it.

Maintaining Morale and Building Depth in Roles
Yeah. I mean, it’s a good call out because this is one of the trickier aspects to navigate. I think the important thing as you start to bring in specialists who, in some cases, might create layers that didn’t exist before, is to frame for the generalists how this is going to benefit them.

What I’ve typically found is that a lot of times, while the generalists might enjoy the flexibility of their roles, they also realize that they need to be clearer on their career growth and progression. So it’s essential to sell them on the depth they’ll gain through this new leader who will train and enable them, making them even more valuable in the future. We talk a lot about the concept of a T-shaped marketer.

To be truly successful, especially if you want to be a CMO, you need a T-shaped skill set: deep in one area but dangerous across multiple areas. So I tell these generalists, look, you’ve started on that journey of breadth, but to be successful, you also need depth. We then have open communication to determine where they fit within the different teams and specializations that we’re building up.

As for growing them and maintaining consistency, it centers around a willingness to go slow to move fast. Sometimes, it takes time to align around the foundational frameworks that will guide marketing strategy. A lot of specialists want to ensure they’re anchored around key insights driving the strategy. You need to invest that time in getting alignment.

For example, bringing in a product marketing leader means they’ll quickly want to drive consistency in storytelling. That might mean building out the messaging architecture, rather than rushing to update the website and sales materials. Without that foundation, they’ll make mistakes that slow them down. Investing in alignment around those North Star frameworks benefits the team as they go through this maturity and sophistication process.

Measurement and Scaling Marketing Operations
One of the things you brought up is measurement. Measurement is increasingly important in marketing these days. A question I get asked a lot, and I’d love your opinion, is: at what point do you hire the marketing ops person?

Unfortunately, in some organizations, the CMO might report to a CRO who gives them a rev ops person who doesn’t know or care about marketing. They don’t look at ROI correctly, focusing solely on sales metrics. So when do you bring in an ops person, and how do you scale from there?

Yeah. I think, as a CMO, you’re responsible for communicating value back to the business. Personally, I lean towards bringing in that ops person as soon as possible. In the early stages, your head of demand gen can wear that hat because they often have a technical skill set paired with a strategic one, which allows for scrappy operations.

But once you see traction and momentum around effective tactics, that’s the signal to bring in an operational resource. They quantify the impact of initiatives. While a demand gen person will focus on core metrics, ops provides the nuance. For me, once you have two or three demand gen folks, that’s when you bring in an ops person. It removes the operational work from demand gen, creating scalability and helping you quantify impact, which can lead to further investment.

Scaling Product Marketing and Cross-Functional Alignment
You’re deep in product marketing, which is challenging to hire for. If you’re a one-product company, hiring several product marketers can be tough because segmenting the role too much dilutes product marketing’s value. How have you scaled product marketing in single-product organizations?

Investing in product marketing consistency is crucial for a small team. I focus on building out core messaging frameworks, from mission and vision to brand story, product value props, and differentiators. Even if you’re multi-product, it’s important to do this at the platform level.

When scaling, look for nuances in your product’s go-to-market role. If one product is your entry point, that signals when to tell a more granular story. I assess both upstream and downstream to determine when that nuance develops. When product management structures their teams for personalized partnership, or when sales needs specific product story alignment due to competitive factors, that’s when you break down responsibilities.

A strong framework as a North Star sets up new hires for success, anchoring them as they build product-specific components that ladder up to broader positioning.

Hiring for Diverse Skills and Team Cohesion
Another challenge CMOs face is needing a wide variety of skills to succeed. In marketing, you need visionaries, strategists, detail-oriented tacticians, creatives, writers, and analytics experts. These people have different personalities and don’t look at the world the same way. How do you get such a diverse team to work together?

You have to establish consistent values across different marketing teams. For me, I prioritize customer-centricity, metrics-driven focus, and strategic alignment.

Customer-centricity brings empathy to roles; great marketing is rooted in understanding our customers, their pain points, and how we communicate our solutions. I value data-driven individuals because marketers can fall into a binary way of thinking, such as, “Did I deliver this asset?” We’re here to deliver business impact, so being data-driven enhances that perspective.

Strategic alignment ties everything together. Seeing the big picture and connecting work to broader goals ensures motivation and avoids narrow focus on individual objectives. In the end, we’re here to win as a business. Defining these values ensures that even with diverse personalities, there’s cohesion in approach.

Advice for Aspiring and Current CMOs
What is the greatest advice you can give to existing CMOs or those aspiring to the role? What’s the best thing you’ve learned that can make an impact?

It ties into this last question: We win together or lose together. As a CMO, you must understand how interconnected your work is with other departments. Marketing sits in the middle of many functions, so it’s hard to succeed without others succeeding alongside you. Embracing this mindset ensures success because it drives shared accountability.

It also improves your collaboration and fosters openness with cross-functional partners. This mentality provides the runway to showcase your impact and success. Keeping a positive attitude around broader business success, rather than focusing on isolated wins, helps overcome challenges and keeps you motivated.

Conclusion
This was awesome. Thank you so much for your time today. Really insightful points here. For those of you on this podcast, take these words to heart. Jason’s approach to the holistic picture brings together different elements needed for a successful team.

One last note: be judicious in hiring. In high growth, if the CFO says, “We’re hiring a hundred salespeople, so you have ten new hires this year,” you don’t want to hire just to make a quota. Think carefully about personalities and structure, as Jason did, to ensure everyone works in harmony. Jason, thank you again. Hopefully, we’ll get you on another podcast soon, and good luck at Customer.io.

Thanks, Scott. Appreciate it.