Heather McCracken has never been one to follow a conventional path. She’s helped launch a cruise ship, lived and worked from an RV while traveling the country, and built a career around problem-solving and fixing complicated user problems. Today, as a Senior Product Manager at Tinubu, she brings that same curiosity and user-obsessed mindset to Surety modernization — helping transform manual, fragmented workflows into ones that are simpler, faster, and more intuitive. Her focus: understanding real user pain points and translating them into thoughtful, high-impact features that move the entire industry forward.
Q: What’s your day-to-day like at Tinubu?
A: My role centers on understanding what our customers truly need — not just what they ask for — and transforming that into clear, buildable requirements for our engineering teams. On any given day, I’m talking to users about their workflow challenges, defining requirements for new capabilities, and helping guide our broader platform modernization efforts. At the core, I’m here to make sure we’re solving the right problems in ways that genuinely improve their day-to-day work.
Q: You’re fairly new to Tinubu. Where were you before?
A: I have nine years of B2B SaaS platform experience as a product manager. Directly before Tinubu, I was working at Disney Cruise Lines on the back-end systems and helping them launch a new ship called the Adventure. Before that, I was a head of product and worked as a management consultant at McKinsey.
Q: Do you feel any attachment to the Disney Adventure ship?
A: It’s launching soon, and I want to see it so bad. I have a lot of friends who still work there, and I’ve asked them if there’s any way to get a preview cruise. They say the spots are all taken. I mean, someone's got to have one spot on one of the preview cruises for me, right?
Q: How was Disney in general?
A: Disney is a magical land. I really enjoyed being part of a larger organization with established processes. When I’ve worked at smaller companies, I’ve had to set up product processes and standardize workflows. Being at Disney, I was able to go back to an individual contributor role, and I liked that.
That’s part of what I enjoy at Tinubu, too. I really like talking to our customers, defining their challenges, and brainstorming solutions to ease their day-to-day workflow pain points. It delights me to say, “OK, here are the obstacles they’re facing, and here’s how we can fix them.”
Q: What draws you to that kind of role?
A: I’m obsessed with users and how things work. Even in my day-to-day life, I look at well-designed products and think, “OK, the product manager really understood the pain points here.” I’m always thinking about the what-ifs and the future. Users know what they need, but they don’t always know what the solution should be, and that’s our job to figure out.
I always say, if you had asked me in 2002 what I wanted for music tech, I would’ve said, “A better CD player.” I never would’ve said, “I want digital music I can stream anywhere without carrying CDs.” So when users ask for a faster version of what they already have, we also have to ask ourselves whether there’s something even better we can build — something that truly delights them and makes their work easier.
Q: Where are you based?
A: I’m in Orlando now, but I lived in an RV for three years and traveled full-time before I worked at Disney. I was 100% remote, working for a market research platform. I have seen every mile of coastline from South Padre Island, where we saw SpaceX launches, to the Florida Keys and then all the way up to Pennsylvania. Although, we skipped Miami.
Q: Why did you skip Miami?
A: It’s not like you can park an RV easily in Miami, and where you can park it, you might not want to sleep at night.
Q: How was the overall RV experience?
A: It was the most epic journey ever. The goal was to see a lot of the Southeast United States and have the freedom to explore what we wanted. We saw a lot of breweries. We saw a lot of wildlife. We saw every beach we could possibly imagine. We had the freedom of being able to explore places with our own house and at our own pace.
We put 27 tires on vehicles in five years. And most of them were on the trailer. Because when you’re towing and you’re putting that many miles on a recreational vehicle, things just happen.
Q: This is your first time working in Surety, how are you finding it?
A: It’s a very interesting industry. It’s very niche. There’s a lot of growth potential, a lot of white space, and a lot of ways that Tinubu can improve Surety operations in ways that other software providers have never been able to. There are platforms out there, but I don’t think anyone has come in with a product mindset and tried to really define what the user experience should look like for somebody that is an underwriter or, say, an admin at a carrier.
For me, there is an opportunity to leverage my B2B SaaS platform background and think about what should be standard for a good SaaS platform and how we can bring that to Surety.
I’m interested in how we make things better for everyone in the industry and give them a high-functioning, enterprise-level platform. In Surety, there is so much variety based upon different types of bond, how various carriers work, and so on. Part of our job is to work out how we take multiple processes and standardize them for people in ways that work for them. That’s one of the most interesting parts of the job.
Q: What's something you are working on now that you're really excited about?
A: While I have been working mostly on refining our new Status Inquiry feature, I'm excited to move onto what we are calling an Underwriter Workbench because it significantly expands Tinubu’s capabilities: it turns the platform into a powerful underwriting platform that our contract Surety customers will really benefit from. Right now, senior underwriters have to do a lot of their work (such as WIP trending, financial ratio analysis, gross-profit fade tracking) using a mix of spreadsheets, email and other tools. The Underwriter Workbench changes that and provides a comprehensive solution for one of their biggest pain points.
We'll start by tackling the biggest daily challenges with smarter data handling, clearer visibility into accounts and jobs, and better tools to reduce manual effort — pulling more of the underwriting process inside Tinubu where it belongs. The result will be that underwriters spend far less time on grunt work, spot risks faster, collaborate more securely, and can focus their time and energy on high-value tasks. It's a game-changer for contract underwriters that will cement our leadership in the space.
