How I got here: Matt Gallatin on Finance as a strategic partner

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Matt Gallatin is the Chief Financial Officer at Stack Overflow and is responsible for finance, accounting and corporate development functions. Matt brings over 20 years of broad finance leadership experience in strategic and financial planning, scaling high-growth companies, and corporate finance. Most recently he served as the Chief Financial Officer (CFO) of Reltio and he was previously the CFO at Drawbridge (acquired by LinkedIn), OneLogin, and ShareThis. Prior to his roles as CFO, Matt was the VP Finance at Brand.net, worked on the corporate finance teams at Yahoo! and Applied Materials, and began his career in investment banking at Merrill Lynch. Matt completed his MBA from Haas School of Business, University of California Berkeley, and graduated from Allegheny College with a Bachelor of Arts in Economics.

Welcome Matt. Please tell us about yourself. What do you do today and what company do you work for?

I'm the Chief Financial Officer at Stack Overflow. Stack Overflow is a community of roughly 100 million developers and technologists around the world who use our site to get questions answered: "How do I solve this problem in Python? How do I spin up an instance in AWS? How do I evolve from a back-end engineer to a front-end engineer?" It's really a community of technologists from around the world figuring out how to do their job better and more effectively.

When you were a kid, did you ever imagine yourself becoming a CFO?

When I was younger, I thought I wanted to be an architect until I figured out you had to be pretty good at drawing, which I’m not great at, so I had to course-correct and shift from there. My grandfather and dad were entrepreneurs, so I knew I wanted to go into business — whatever that meant.

I majored in economics as an undergrad and started to enjoy the intersection of data and analytics with the real-world issues, although some may argue economists live in a fantasy world of perfectly efficient markets. Seeing how qualitative and quantitative analysis can help to explain what is happening across different elements of the economy was really interesting. 

My first job out of college was at an investment bank which proved to be a great training ground for me to learn about corporate finance, build financial models, and make strategic recommendations based on the analysis that we had prepared.  I ended up spending almost eight years in banking, working in both New York and the Bay Area.

After this I went to business school and then transitioned to a corporate finance role at Yahoo! There, I started to focus more on execution and understand how finance supported business decisions across teams — from sales to product, to engineering — to really bring to bear whatever strategies that we recommended. That was about thirteen years ago, and I’ve been a startup CFO ever since. 

Going from investment banking to working at a company doing corporate finance must have been a big cultural shift. How did you navigate that?

In banking, you sit outside of the organization and you may be a strategic partner and work closely with a company, but you're never really as close to the people running the business and fully understanding their strategy, gaps in the product portfolio, or long-term vision and priorities for what they want the company to become. That all happens inside the four walls of the company. 

In the corporate finance function inside a company, you're part of the operating team and directly developing that strategy and executing against it. You’re able to experience the real impact that finance is making on strategic decision-making and execution.

I really wanted to build things from the ground up and understand what it means from a product, engineering, and go-to-market perspective. 

How does finance play a strategic role at Stack Overflow?

Stack Overflow has several products. The first is the public platform and our community that millions of users visit every month. We also have a SaaS product, Stack Overflow for Teams. For example, a large global bank has a lot of engineers and technologists inside their organization, and many of them already use Stack Overflow’s public platform in their day-to-day work. Stack Overflow for Teams offers a dedicated and private space for those folks to collaborate and share their institutional knowledge. Stack Overflow for Teams also offers integrations with other productivity platforms, including Slack and Microsoft Teams. 

Finally, we have our Reach & Relevance products, which consist of traditional online ads, as well as Employer Branding products for organizations looking to build their brand with developers and technologists.

On one hand, our business is simple in the value we try to deliver to our end customers, but it's also extraordinarily complex with different products and monetization strategies. And so that lends itself to finance being a strategic partner across the organization and being pulled into a lot of different discussions around where we can make the best trade-offs and the right investments and prioritize the right strategies.

Who are some of your business counterparts and how do you work with them?

We have a CRO who manages the monetization of Stack Overflow for Teams, our Reach & Relevance line of business, and our customer success function. We work pretty closely with him and his go-to-market teams, answering questions like: where do we allocate resources if we have a finite amount of capital? Is it best served putting it against that Team's subscription product, or against our Reach & Relevance products? Where is there more demand? Where is there more opportunity? And where is there more long-term value being created?

How is your finance team structured? How big is it?

I've been with the company for just about two years and I was incredibly lucky to inherit a really great team. I have a controller and a vice president of finance who both report to me and oversee teams of around ten people each. The team's only grown moderately and to their credit, the controller and vice president have done a great job building out a really high-performing team. We've had very little turnover, which is great, which I think signals there's a ton of opportunity to learn and grow at Stack Overflow and work on really compelling, interesting projects. 

Having a great team has given me a ton of leverage, and enabled me to focus more on strategy and execution versus having to rebuild a finance function. 

Describe that ‘aha’ moment of becoming a CFO?

My experience at Yahoo! was very eye-opening from the perspective of being that bridge between corporate finance with more operational finance and really shining a light on the fact that operations and execution really influence financial outcomes versus building a financial model to drive towards operational outcomes. The more projects I worked on and the more we were able to bring in product teams, engineering teams, and sales teams to be involved at the front end of the process versus dumping something onto them at the back end of the process just highlighted that the more finance was engaged, the higher the likelihood of success. Figuring out the operational elements of a partnership or a particular initiative was as important as penciling out the financial forecast. 

With that mindset, I really try to be a strategic partner to my peers on the leadership team, whether it's the CRO, the Chief Product Officer, the CEO in particular, or Chief People Officer. My role as a CFO is to be a resource to help my colleagues think through some of the operational complexities where some of the risks might be. 

When I left Yahoo! and joined my first startup, I encountered a lot of new ground. What does it mean to go through an audit? What does it mean to do a foreign audit evaluation? What does this planning process look like? All of these things that you never really think about being in a corporate role that really the finance team leads at these smaller companies. And then there's sort of everything else that no one else wants to do, real estate, benefits, insurance, all of these things that all fall under the finance remit. And so it's a little bit of what you can take on as much as you want, which to me is really compelling and interesting.

What advice do you have for FP&A analysts or managers who want to advance their careers?

There's no lack of opportunities, whether it's at a startup or a smaller company or a large enterprise for a smart finance person to be part of a broader team looking at entering a new market, or launching a new product. One of the benefits that finance people have is they see the outcomes of the operational decisions that are made, whether that's in a specific segment or company-wide. Being able to connect those two things together and understand where the financial risks might manifest as a result of operating risks is not necessarily a lens that other operators may be able to bring to an initiative or a project. 

There's always an opportunity for smart, thoughtful finance people to be part of a project — from running a financial model and building out the forecast, partnering with product marketing to figure out TAM, or defining the ideal customer profile. Raise your hand and ask for those kinds of projects or even take the lead on them. 

By doing so, you’ll also find yourself more integrated with other parts of the organization, and forced to think a little bit differently around operational risks and considerations. The more you can do that and work cross-functionally, the better off you'll be as you evolve into a more seasoned finance leader.

Being great in finance goes beyond technical expertise. What is the most critical soft skill that is the hardest to master?

Finance is a service organization — we support the rest of the functions across the company. Ironically, most of what other parts of the organization want to do are the exact opposite of what finance wants to do. Sales and marketing wants to spend more money. Finance doesn't want to spend more money? There's inherent tension there, which in some ways is healthy?

That said, finance can best serve the company by being good partners  — and that means putting yourself in the other person's shoes and understanding their rationale and why they want to take a specific perspective.

It’s okay to say no as long as you're having some dialogue and provide context as to why you're saying no. Put some effort into understanding the other person's perspective and identifying the risks and opportunities associated with that and be very clear. That's half the battle in working with other stakeholders. They may not like that you said no, but I think they'll appreciate understanding how you came to that decision. Then you can figure out ways to address the risk and concern, and then course correct and pivot. 

Mastering active listening and building trust becomes more and more important as you become more experienced with a broader remit.

This also helps build trust so that you can have the tough conversations and people feel that they're in a safe space and open up on what their real motivations and goals are. That's a much more effective dialogue — and where I've found the best relationships I've had with other members of the leadership team is being able to have those conversations. I'm not going to hold it against them in the budget process, but rather be a trusted partner for them when they're trying to make decisions. At the end of the day, we’re all working together to do what's best for the organization, but there's certainly an element where we all tend to think about things that are best for ourselves. Letting them do that and being respectful of that is an important part of the collaboration process.

What are your priorities for 2023?

We actually just had our company-wide meetup a couple of weeks ago. We're a remote first organization and every year we bring together the whole organization in one location. It’s a great event because it's the first time a lot of people have seen each other outside of a Zoom screen and it’s more effective to be collaborating in person. A key theme at our meetup — similar to many other companies — was a  shift from “grow, grow, grow” to “grow, but efficiently.” 

So one of the things that the finance team is prioritizing is how do we make sure that we're making the right investments, that we're tracking our investments, and holding ourselves accountable to make sure we're investing in the most efficient things, the things with the highest probability of outcomes, and how do we do it in a way that's open and transparent. 

As an organization we’re already pretty transparent but this new focus requires even more transparency and openness as it relates to what we're communicating out to the rest of the organization. How can we make sure that we're providing the right insights and the right analytics on an ongoing basis so that we collectively can make the right decisions? Because if it waits for me to read out last quarter's performance to make a decision, that's too late. And so that's a big thing that we're working on this year.

I don’t want finance to slow down the business — we want to help the operating teams execute more efficiently. I want to give operators discretion to work within guardrails and parameters because they know their business better than I will ever know. The finance team ensures they're staying within the guardrails and provides them with the right information, but we don’t want the operators to have to wait for finance to approve everything. 

We often hear about product or go-to-market teams operating against OKRs, but it seems like that's hard to pin down on finance. What's your take on OKRs for the finance team?

I'm a fan of OKRs. We don't necessarily have an OKR structure at Stack Overflow, but I try to set high level goals in collaboration with our controller and VP of Finance. 

One of the challenges in setting OKRs for a finance team is around how to set objectives without them becoming a glorified to do list. So what I try to do is to set our department goals to create focus beyond the day-to-day tasks and to use the goals as ways to optimize our core responsibilities and to expand our capabilities. These goals are thematic across the finance function, whether it's process improvement, improving analytics, or onboarding a new tool. Then the key results are how we will measure improvements against our existing capabilities.  OKRs can help finance teams get alignment and prioritize efforts to improve the regular and routine parts of the function and to identify the projects that can have a meaningful impact on processes.  

What or who inspires you?

I was at dinner last night with a friend of mine, and we were talking about our families. He asked what my parents did professionally, and I started to go through the litany of things that my dad has done. He’s run a family business, sold that, built his own business, sold that, and ran a community hospital for a while, along with several other projects.

He's done a lot professionally and just figured out how to make things work and did it in a way where he's been successful in his outcomes, but also being incredibly well respected in his community. They live in a small town in Western Pennsylvania, and he's been on several boards and involved in different community-based organizations. Over the 50 years of his professional career, he's built a lot of trust, goodwill, and respect in his community, which matters as much as any sort of financial or business outcome that he might have. I aspire to that.

I've tried to take a page out of his playbook. I'm on the board of a nonprofit and on the board of a small book publisher. With all that has happened over the last year with the economy and changing business focus, I haven’t been able to devote nearly as much time to those things as I would like. One of my objectives is to spend more time on those organizations this year.

What advice would you give your 18-year-old self?

My daughter's graduating from high school and starting college in the fall. And so I've been thinking a lot about this as of late.  What I’ve told her is that it's okay to not know what you want to do with the rest of your life when you're 18 or 20 or 22 years old.

In fact, that’s more normal than knowing what you want to do for your career. And the reality is, you're probably not going to be doing what you think you're going to be doing 20 years from now. So take some time to figure it out — it's okay to think about a gap year, living abroad for a time, or volunteering.  

Take a beat and figure out what you are really passionate about, and then build your career trajectory around that.

Eventually you'll get there and it's okay to get there after a while — it doesn't have to be six months after graduation from high school or college. Reflect a little bit and be patient. You have your whole life to figure this thing out. A career can be many different things; it’s not just your job.

Did you have key people who played a role in your life?

When I first started working in banking, there was a young managing director who pulled me aside and showed me a big deal binder. He spent about three hours walking me through the different agreements — what they looked like, what certain terms meant, and why it was an important part of the deal process. I appreciated that he took the time to invest on the front end and gave me context around all of the elements of the deal process. Not just the financial modeling, that was table stakes.  But he knew over time the scale and leverage I could give him would only be if he invested that time in me up front. 

I really took his approach to heart in terms of how I try to work with my team today at Stack Overflow. I try to give them context on why we're looking at something or why it's important for us to change the way we approach issues. What is the macro theme or the macro issue that we're trying to address? I then try to leave it to them to figure out, ‘Okay, what are the right analytics? What's the right process?’ 

Ideally, I’m building trust and accountability with my team by giving them the 10,000-foot view and letting them execute because they're much closer to it than I will be and much more equipped than I would be to make a recommendation or define a process. And so that's something I very much took away from that experience.

What is your passion outside of work?

I'm a huge sports fan. Growing up in Western Pennsylvania and I am a longtime supporter of the Steelers, Penguins, and Pirates.  I love to watch sports. I've been to European soccer matches, Formula One races, and golf tournaments. I'll even go watch local high school baseball games.  I read books about it.I watch it on TV. I've convinced my kids to be sports fanatics too. 

What's your favorite F1 track or race?

The one in Azerbaijan in Baku is actually a really good race, despite being new. It is a good mixture of speed, technical elements and the visuals of a street circuit. And then Silverstone is a great track because it is really fast and there's a lot of opportunity to pass given all of the corners.  And there's a ton of history there. 

What book are you reading right now? Or is there an audio book or podcast that you particularly like listening to?

I'm reading a book called “Expected Goals” by Rory Smith. He's a New York Times writer covering soccer, and it's about the rise of data and analytics in soccer. It's a nice blend between the finance guy and the sports fan. As for podcasts, I generally tend to listen to lighter entertainment to unwind when I'm taking the dogs for walks. There's a really funny one called “Smartless”, which is hosted by Will Arnett, Jason Bateman, and Sean Hayes. I also listen to a lot of sports podcasts, in particular European soccer and golf podcasts.

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