Leader Spotlight: Building strong foundations, with Matt Strozak

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Matt Strozak is a product leader who specializes in B2B SaaS and marketplace products. He was most recently the Vice President of Product Management at Upwork, a freelancing platform. Matt started his career as an analyst at Accenture before joining CareerBuilder, where he spent nearly 10 years in the product function. He then became VP of Product and Operations at PowerReviews before transitioning to Upwork.

In our conversation, Matt discusses his emphasis on building strong foundations to ensure the product supports current and future needs. He also talks about the importance of being both patient and stubborn in product management because of how quickly things change.

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Competition and focusing on your ICP

From your perspective, given your extensive experience in B2B SaaS, what’s your approach to ensuring product offerings stand out?

There’s a ton of competition when it comes to B2B SaaS. First, it’s important to acknowledge that there are multiple types of competition — adjacent competition and internal competition, or attention-takers. Adjacent competition includes the various tools customers could use alongside or in substitute of yours. Internal competition includes things like politics and budgets that create competition in an untraditional sense.

There are three things that B2B SaaS companies can do to stand out. The first is to solve the customer problem. There needs to be a clear and relevant ROI. What is the customer getting out of it? What are they doing? As a product leader, you need to be able to show, quantify, and continually point to that. Start with one area that you can do extremely well, own that area, and become embedded in it. The product needs to become a foundational pillar that can stand on its own. Once it’s standing on its own, you can move into different areas and become a trusted partner advisor. You also need to be embedded in the customer’s workflow.

The second is becoming commercially viable and building go-to-market excellence. You need to have a solid launch process, go-to-market, partnerships with marketing, sales, and support, and alignment across the board. Pricing needs to be logical and scaled, and there needs to be a clear, solid value exchange between the company and the product.

Finally, you need to do the basics extremely well. Your UX doesn’t need to win any awards, but it needs to be simple. You have to think about things like data security, data management, access controls, integrations, and reporting. If you don’t do those things well, you won’t even be considered in a competitive environment.

If an initiative is working well enough, sometimes the organization may not feel a sense of urgency to switch it out, even if change is needed. As a product leader, how do you handle that?

Sometimes, you have to acknowledge when you can’t win. You need to find the right opportunities to go after. That’s one of the main differences between B2B and B2C products — much more targeted and specific in your approach. In B2C, you can blanket things and find different audiences.

In B2B SaaS, sometimes it comes down to timing, creating the problem, or finding a different value proposition that aligns with your product. Finding that timing and decision to say, “We’re going after this part of the market, user type, or function” is super important and impactful when people are not considering different tools.

If existing tools are working OK and your reach is broad, you need to make sure that you are focusing on your core ideal customer profile (ICP) and your target segment as much as you can. I would be more concerned if you’re not able to move the needle in that ICP than if non-core customers aren’t using the product. If you’re not connecting with your ICP, that demonstrates a disconnect.

Being both patient and stubborn

What’s your approach to understanding the evolving needs of enterprise customers?

Feedback is critical to building a high-performing product. Typically in B2B SaaS, you’re making bigger, bolder decisions with less information. Figuring out that feedback loop and executing it is key. The best product teams are great storytellers. They can combine qualitative and quantitative feedback and weave together a story that speaks to the vision, strategy, and impact the product has in different areas. With feedback loops, it’s easier than ever to capture data, but finding that signal through the noise and turning that signal into a coherent story is crucial.

When it comes to enterprise users, it’s difficult to get feedback. There aren’t as many touch points compared to a B2C business. It all starts with identifying your target customer segment, because the foundation is built on getting feedback from the right customers. You also need to understand the difference between buyers and users. Buyers are looking at value propositions, while users are looking for more specific value.

When I think about feedback loops, there are two things that I try to get toward: breadth and depth. For breadth, I’m referring to things like high-volume data points, surveys, and metrics around adoption, usage, and NPS. For depth, this is where you rely on real user or customer feedback. You are either talking to them about their strategy, developing a client advisory board, or executing internal listening tours. You need to have both breadth and depth as they complement one another.

You’ve also talked about your preference for being a builder rather than a tinkerer. Could you say a little more about that?

This preference is inherent in many product leaders. Being a builder, in my mind, is about finding ways to drive progress. You are consistently analyzing the thing that you’re looking at and trying to make it better. Tinkerers focus on smaller details, such as, “We’ll change the paint on the wall and see if we like something like that,” while builders think, “Why is this wall here? What is it doing? If we move the wall, what opportunities would we have?”

You have higher success building a great product if you’ve already built a great team and have a great system in place. That’s why I focus on foundations — they build off each other and then you can build extensions on top of that.

In terms of scaling a B2B SaaS product, what approach do you take to ensure the product’s architecture supports both current and future needs?

If you have a builder mindset, you’re always thinking of the years ahead and the foundations you need now to get to. A lot of times when you’re in a B2B SaaS environment, you’re asking customers to make a multi-year commitment in their contracts. They want to know what they’re getting a few years from now, and builders think longer term about the foundation that they’re building for those customers.

You need to be able to understand where the market is going to start building the right things. You also need to be both patient and stubborn because things are going to come at you and change quickly. Stay vigilant with the vision that you have.

Having a medium to long-term vision and executing against that vision is one of the harder aspects of product management. There are always new opportunities to go after. Of course, you don’t need to be stubborn to the point of having blinders on, but you do need to have confidence in the information in front of you — that the long-term vision is the right vision. You know what the solid foundations are, and you can build on top of those.

The thing that I see B2B SaaS companies struggle most with is patience. Building a B2B SaaS product is complex. It takes a long time. Engaging with a B2B customer goes through a long sales cycle. Oftentimes, you’re making a bet. You’re releasing something and you won’t see anything come in for six months or longer. That feedback loop that we talked about earlier is slow, and this is certainly where patience comes in.

The way that you get through that is by finding ways to show short-term wins or leading indicators — whether that’s client feedback, market analysis, or market trends that you’re going after. You need to bring those things into that vision and data storytelling.

Earning the right to build

In your career, you’ve led strategic shifts up-market. What insights can you share about understanding and meeting the needs of enterprise customers?

At some companies, traditional customers were individual users, and dealing with a user is very different from dealing with a corporate buying committee. Each of those entities has different personalities and needs. Once you realize that you’re ultimately servicing a company, it changes your mindset on how you’re going to win business. You need to build for the company entity first, and then the user second.

There are different questions that you’re asking as you’re going through that transition. If it’s a user, it might be a specific workflow they’re asking a question on. If it’s a company, how does this fit in their ecosystem? Every enterprise customer has different tech stack variations. That’s important because when you plug into an ecosystem, you’re dealing with a lot of internal competition.

Decision-making at enterprise customers is different. Budgets come into play along with tech and resource constraints. There are company dynamics and politics that you might not even be aware of. It’s not a transactional decision, it’s a relationship-based decision. Enterprise customers are going to have higher expectations. You have to be able to demonstrate your ROI through different channels and mediums.

How do you use directional signals to make sure that you are being patient yet staying on track?

I’ve found that the most successful long-term initiatives result in you earning the right to build. You can’t put all of your eggs in the first six-month basket and assume it’s going to hit. If you don’t have something that’s coming three months after that, you can’t have that perpetual cycle of value that you’re driving your customers toward. If you’re consistently showing that you’re delivering value because everything builds off each other, you’ll create a flywheel.

Getting started is the hard part. The first six months of an initiative are critical for showing value. It’s typically a blend of financial and usage metrics along with storytelling. Go back to your feedback loops — call recordings, keywords, and sentiments are all directional indicators. You want to go in saying “We did these foundational things and now, it’s easier to get through deals. We have more opportunities for these types of customers.”

Scaling teams and hiring at different stages

Can you share the hurdles you went through growing your enterprise R&D team from 10 to 100?

At the onset of leading a team, you want to make the team successful so there is a lot of doing. I was sitting with teams in the details, writing tickets, and helping QA. When you realize that there isn’t as much leverage as a leader because you’re building the team, you need to move into guiding. Knowing when to move out of the doing and into the guiding phase is a big hurdle.

Further, direction and prioritization are higher leverage in larger organizations. The bigger the team, the higher the investment. This means that the company is looking for a higher ROI. Your bets need to be solid and you need to have a high confidence that they will pay off. It’s easy to fail with a small amount of resources and communicate that failure. Communicating failure with a large amount of resources is much more painful. To avoid this, prioritization of the right things and decisiveness to drive action are key.

Another hurdle is team and skill building. When you have a smaller team, you need generalists so they can move in multiple different directions. We did this when we were hiring for this R&D function. Then, as we grew the team, we started identifying specific skills that we needed. The bigger the team, the more specialized skills you need.

Finally, balancing the long-term vision versus the short-term results is vital. Your communication style needs to change. You need to go broader and be more visionary. Your communication has to hold more weight. You need to continually evangelize for your customers the results that you’re putting out. Organizations always have different areas that they can prioritize, and making sure that you’re focusing on the right customer set is important.

Are there certain traits or characteristics that you look for when hiring, and does your wishlist change based on team size?

The most successful teams are the ones that come from a diverse set of backgrounds, experiences, and skill sets. You can do that with a team of two or three, but you need to be continually looking at and understanding the team dynamics. The best teams that I’ve worked on are ones that had individuals who came from different areas of the business. For example, a solid team I managed had a PM who grew up in the customer support organization, an outside hire from a B2B SaaS company for 10 years, and a former engineer who moved into product.

This team composition will help foster a community that has a willingness to learn and be open to different perspectives. I find that’s more important than the individual skills. While the movement from generalist to specialist is important when it comes to team size, bringing in diverse backgrounds and experience is agnostic.

Marrying baseline and initiative-based metrics

Lastly, what KPIs do you tend to focus on when you’re looking at measuring the success of your product strategies?

There are two components: baseline metrics and initiative-based metrics. There’s always a baseline set of metrics that you need to have for B2B SaaS, including business metrics like revenue, cost, etc., and product metrics, such as engagement, adoption, usage, and ROI. There are also operational or engineering metrics. Whether it’s page speed or load speed, those go into the operational metrics. Those are the baselines for understanding how your product area is performing.

Then, you need to couple those baseline metrics with what I’ll call initiative-based metrics. Those are a little bit more specific. You might have hypotheses like, “If we are doing X, it will drive Y.”

The key thing here is to marry the two together. As initiatives come through, you should see improvements permeate throughout your baseline metrics. You should see revenue go up or down, for example. Baseline metrics are more evergreen — they shouldn’t change as much. Though you shouldn’t see the same thing every year, the foundations shouldn’t change dramatically every quarter, meanwhile initiative-based metrics can change dramatically in a short time.

You need to couple those two together, because that will help you navigate the short term and set the stage for the long term.