Leader Spotlight: Turning uncertainty into opportunity, with Jake Gutting

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Jake Gutting is the SVP of Product Management at Ncontracts, a leading provider of risk management and compliance solutions for financial services companies in the U.S. He has vast experience in financial services across a wide range of businesses, from Fortune 500 to startups.

In our conversation, Jake shared his experience working in a highly regulated industry that requires quick pivots in the face of uncertainty. He also provided insights around shifting strategies when things don’t go as planned and promoting a culture of trust in his teams.

Our conversation has been edited lightly for brevity.

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Navigating uncertainty

In your role at Ncontracts, how does the regulatory aspect of financial services impact the product management function?

There’s a massive impact — it’s constant and consistent. It’s really the reason we exist; our business and roadmap are driven by regulatory change. That change means we’ve got customers and we’ve got good business. We have to make tough decisions around when to invest in different features around forthcoming regulations.

For example, right now, due to section 1071 of the Dodd-Frank Act, there’s going to be a significant change to how our lenders and institutions interact with their customers. But the deadline came and went, we got some information, and now it’s going through the courts again. It’s challenging to know when to invest in these things because we want to time the market correctly and make sure product-market fit is there, but all these pieces are moving.

We try to find where we can provide immediate value and where we can engage with those customers for long-term roadmap ideas. Customers tell us what they think about software and features, and we’ll move that through as we understand more and learn how they’re going to incorporate the regulation into their businesses.

It can be very difficult to stay informed about market changes too, particularly with something changing both at the federal and state levels and in different jurisdictions, and incorporating that into the roadmap.

We have a model where teams that provide a lot of guidance and leadership to our customers as knowledge-as-a-service are also subject matter experts (SMEs). Having in-house expertise is something that actually drew me to the company. You don’t always have that luxury in a product management organization.

It does sound like you’re navigating a lot of uncertainty. Does this impact who you hire?

Yeah, we try to find a balance. For every seasoned product manager that we hire coming from another industry or a B2C business, we try to balance that with an SME coming into the organization, and the two can learn from each other. Maybe not directly as peers, but certainly as a group.

Opinions are irrelevant

So when you engage your customers and get insights from them, what is your process like for further ideation and research?

We’re starting to hit our stride with creating a culture of making a discipline and creating a playbook. We have a playbook for what a frontline product manager, product line lead, and designer looks like. This helps create discipline around processes.

In the playbook itself, we ask, “What’s the least amount of work we need to do to learn the next most important thing?” Asking that question at each step in the process helps break down complex problems into small pieces of work that we can solve and understand before we start solutioning things.

We work through that playbook, make sure we’re trying to find the smallest things, and then enforce learning and metric-tracking against that when we’re done.

Where do the ideas usually come from? Do you get ideas from your customers or from researching changes in the industry?

An instructor in a pragmatic marketing course I took a long time ago said, “My opinion, while interesting, is irrelevant.” I remind my team of that a lot and try to enforce that we are not the exact copy of our customers.

We try to be empathetic and understand what it’s like to live and work in a financial institution, and we try to stay close to that. But at the end of the day, they’re going to have the right answers. We try to get the bulk of our ideas from them.

Now of course, an executive or SME might have an idea, and we funnel all of that through tools and processes within our organization to make sure that we’re actually scoring those things and prioritizing them in the right way.

We’re about a 70/30 split: we get about 30 percent of our ideas from us and about 70 percent from the market — i.e., either customers have suggested it to us or we’ve been to a conference or show. We try to lean toward the market for idea generation.

When turning ideas into features, what approach do you use to understand the “why” behind them?

At Ncontracts, we use a triad concept. Each one of our product line, design, and development leads spends a significant amount of time each week in that triad having conversations about things that are coming three, four, or even 12 months out. They start ideating through those concepts so that everyone can understand why they’re doing what they’re doing.

Can you think of a particular product or feature you worked on where you really nailed product-market fit?

In 2019, when I was at Confirmation, we were acquired by Thomson Reuters. I was really proud of that.

We were a local Nashville tech startup. If you’re going through an external financial audit, the auditor needs to see the cash balances. Historically, they’ve been done through fax, email, scan, parcel, post, whatever that looks like, so our business model was an electronic platform to do that clearing.

When I joined, we started globalizing that product and had one of the largest exits in Nashville’s tech startup history. I was proud of how we took one idea and were able to globalize it from this core group of people in Nashville to five different countries with a product that served those different markets.

Pulling success from failure

Can you think of a time when you made a strategic decision and then had to change course?

An example is an acquisition that Ncontracts had. We bought what we thought was a complimentary product, but it was way outside of our core competency. The customers that we were trying to cross-sell and upsell had no interest in buying any of these products.

We had to pivot and figure out how to serve that product line in its own way — we were trying to wedge something in that just wasn’t needed.

We were being diligent about measuring customer success through things like NPS. Our product team and our success teams were working closely with those customers, understanding how this acquisition was working for them. We invested in building it out as its own product line, managed it and left it to its own roadmap, and stopped trying to make it something it’s not. We embraced it, and I think that’s a success coming out of initial failure.

How do you decide whether something can be salvaged or you need to walk away from it?

In this particular example, the due diligence we had done led us to understand there was a loyal customer base. We understood that the customers really did rely on that product, and so we realized it was a viable business to continue to invest in, even if we didn’t need to infuse our products and services into it.

So that’s how we’ve looked at it, we’ve continued to support it. We still challenge ourselves quite often as we look at new opportunities. How do we continue to bring those customers closer to the value we’re delivering? The market for that is very different and not a group that we want to focus on.

What I like about our approach is that we understand our core competency and want to stay there. We’ve created an entire structure around this other product line, so we’re managing that in that way.

Building trust as a leader

Let’s talk about company culture. How do you make sure your team members remain productive while also showing you care about their personal development and growth?

By knowing the team as best as I can. As the organization grows vertically, it becomes a little more challenging. But we do 1:1s weekly with direct line managers and biweekly with our skip levels. We make sure we are making those 1:1s as much about the growth, objectives, and opportunities, not just project statuses. This builds trust and encourages people that if they see a thing in the business that they’d like to go do, they have the trust to go do it.

I also tell my team a lot of times that if we’re doing a good job of growing you as product managers, I want you to have the trust in us to say we may not be the place for you to grow to the next step of your career. I actually see that as a good sign.

As a leader, what advice would you give to PMs who are early in their career? Do you suggest starting at a larger company for exposure to high-level projects or a startup where they can have a bigger impact?

What I would also tell product managers who aren’t really sure what that job looks like is that it’s going to be different every day, and that’s the cool part about it. It’s tremendously rewarding, it’s very dynamic, and so you’ve got an opportunity to sell, to listen, to build, and to work with lots of different people.

I definitely enjoyed and had the benefit of starting with a large company, but I also love the idea of jumping in at a small place and having lots of responsibility — if you’ve got the right mentor.

Where I felt like I had someone give me an opportunity was in that mentoring piece. The large company model does typically provide a little more structure, and that is certainly something I would look for if I were getting into product management. But I would also think the same way with a small company where you can do a lot of different things. I think I prefer that — being where the opportunity for impact is big — but you need the right mentor.

A big part of any product leader’s role revolves around cross-functional communication and collaboration. Could you talk about your approach?

In a product role, one of your biggest value-adds is aligning everyone on strategy and direction so that they can go and execute. To do that, you need to focus on those relationships and have those conversations before it’s launch day, release day, etc.

It starts with building those relationships and making sure that we ask teams what we can do to help them instead of telling them “I need you to do this.” By approaching situations this way, it becomes a much more mutually beneficial relationship.