Lindsey Bailey joined Middesk in 2022 and recently stepped into the Head of Finance role. Since joining, she has built the finance function from the ground up, creating the systems, structure, and foundation needed to support Middesk’s growth.

Before Middesk, Lindsey spent more than seven years at J.P. Morgan in Business Management and Strategy and began her career at Goldman Sachs, focusing on operational and regulatory risk. Her experience across large institutions and high-growth startups shapes how she builds today: with rigor, adaptability, and a bias toward ownership.

In this conversation, Lindsey shares what it takes to build finance from scratch, how the role evolves as a company scales, and why context, curiosity, and trust matter just as much as the numbers.

You started your career in traditional finance institutions like Goldman Sachs and J.P. Morgan. What drew you to an early-stage company like Middesk?

I knew I wanted something smaller where I could have a bigger impact, but I wasn’t exactly sure what that looked like. I spent months talking to people at startups to understand what they were building and what they loved about it. I initially thought I’d join a later-stage company because the jump felt big.

What changed was meeting the team at Middesk. I connected immediately with both the people and the problem. Coming from banks, I understood how painful KYB could be, so it was easy to see why the work mattered. The team felt like the kind of group that would support each other through the messy parts of building, which made the leap exciting.

When you joined Middesk, what did you see as the biggest opportunity within the finance function?

At the start, the biggest opportunity was building structure. There was very little infrastructure in place, and a lot of work was manual. We needed systems we could trust, more consistency in billing and collections, and clearer sources of truth.

Once that foundation was in place, finance could become more forward-looking and strategic. Instead of asking, “How do we clean this up?” we could start asking, “How do we help the business make better decisions?”

Over the past few years, you’ve grown into the Head of Finance role. What shaped that journey?

One of the biggest moments happened about three weeks after I joined, when we started raising our Series B.

I was still learning the business and suddenly deep in the numbers, going invoice by invoice to build confidence in our ARR. It was intense, but incredibly formative. It taught me that even when things are messy, you can figure them out through grit, ownership, and attention to detail.

I’ve also learned a lot about leadership, especially how to balance financial discipline with kindness and make thoughtful decisions while remembering that a company is its people.

From your perspective, what is a finance team’s role in an organization like Middesk?

Finance touches almost every part of the business, from product to go-to-market to hiring.

That means the role goes beyond reporting numbers. The team needs to understand the business well enough to guide decisions, weigh tradeoffs, and connect details to the bigger picture. As we’ve scaled, finance has become a more strategic partner across the company.

What might surprise people about finance at Middesk, and how do you hire for it?

The amount of context switching. You can go from pricing to hiring to data to audit topics all before lunch, and you’re expected to keep up across all of it.

Because of that, I look for people who can operate like Swiss army knives. At this stage, finance isn’t narrow. You have to stay close to the details while also understanding how your work impacts the broader business.

Strong judgment, curiosity, and attention to detail matter a lot, along with understanding the “why” behind the numbers. That’s what helps people catch issues, ask better questions, and be a strong partner.

I also believe in hiring people who are stronger than you in their areas of expertise. That’s how great teams get built.

Of Middesk’s values, which one shows up most in how you lead the finance team?

Win Together.

I never want to ask someone to do something I wouldn’t do myself. I want to be in it with the team, not directing from a distance.

It also means creating an environment where people can be honest, support each other, and do their best work, knowing when to step in and when to step back.

What experiences have shaped how you approach leadership?

One of the biggest things for me is authenticity. Startups have high highs and low lows, and people can tell when a leader isn’t being real. I’ve learned it’s more effective to be honest about what’s hard while still helping the team move forward. That builds trust.

Earlier in life, I worked in an emergency room coordinating trauma intake. It taught me how to stay calm under pressure and keep perspective. On hard days, I remind myself that while the work is important, we’re going to be okay.

How do you recharge outside of work?

I love being outdoors. I’m from Colorado and now live in Washington, so hiking, camping, snowboarding, and paddleboarding are all favorites.

I also love hosting dinner parties with my husband. He does most of the cooking, especially the slow-cooked dishes, and I’m happy to play a supporting role.

What keeps you most excited about this next chapter at Middesk?

There’s a lot of momentum right now. We have exciting product innovation underway, especially around fraud, and it feels like the right mix of people, products, and customers is coming together.

Middesk is solving durable, important problems. Fraud and business identity aren’t going away, they’re becoming more urgent, which makes the work feel meaningful and lasting.

If you’re excited by building, learning fast, and shaping what comes next, it’s a really rewarding place to be.