We're back with another interview this week, chatting with Elaine Milardo, CTO at Odditt, which is a sports data and analytics platform and her most recent product launch: BetFlow.
Elaine knows what she talks about. She has over 25 years of experience driving data-driven innovation in technology, analytics, and strategy. Previously VP of Engineering at DraftKings, she now leads Odditt’s data aggregation efforts to deliver accurate, actionable insights across the sports ecosystem.
Tell me a bit about your background and how you ended up founding Odditt.
Elaine. I’ve been working in data for over 25 years now, and it’s been fascinating to watch how much the field has evolved from simple reporting systems to massive-scale, personalized, highly enriched data products. It’s been amazing to see that transformation from the inside!
I like bringing order to chaos. Data lives in so many places, in different formats, at massive scales, owned by different teams, and I love the challenge of connecting those dots. Whether it’s building relationships across teams, aligning contracts, or turning vast data into something people or systems can use fast and accurately, that's exciting (and, of course, challenging!) for me.
I’ve been really lucky to work at technology companies like Vistaprint and DraftKings, where data is the foundation and keystone to the entire business. It’s a lot of responsibility but a huge impact. When my co-founder Matt Bresler approached me with a vision to turn Odditt into a data company, I was hooked.
Since joining Odditt in April 2024, I have been putting all those lessons back into practice. We’re building something that’s technically serious but still genuinely welcoming; a product that’s elegant in both its design and its data. It’s rare to get the chance to shape something from the ground up twice in a career, and I feel really lucky to be doing that again here.
You’ve just launched Betflow. Congrats! Give me the elevator pitch, and tell me how it stands out from the many betting products in the US today.
Elaine. Thanks! Betflow is really about making sports betting accessible and fun to all sports fans. Most sportsbook apps hit you with a wall of odds and lines. We wanted to offer something that felt more authentic, easy to understand, and tailored to each fan’s interests.
From exploring bets through historical stats and data-driven storylines to exploring teams and players' fun facts, Betflow has it all. We do this across more than 100 global leagues, with extensive coverage of women’s sports, too!
Our goal is to make sports betting easier, faster, and more engaging by turning complex data into something visual and approachable. It’s still about structure, clarity, and insight—but wrapped in a product that’s genuinely enjoyable to use. That’s the sweet spot for me: blending solid data engineering with creativity and a terrific user experience.
What sets Betflow apart is how it uses data not just to show numbers, but to uncover the stories, patterns, and connections that make sports interesting. We surface trends, fun facts and trivia, and unique tidbits that most other platforms overlook.
It’s built on serious data, but it feels approachable - it’s super fast, visual, and easy to use - a product that’s both technically serious and genuinely welcoming.
What first sparked your interest in using data to solve problems in the betting industry?
Elaine. My interest really took off when I realized how central data was to building products people actually use, and nowhere was that clearer than when I was at DraftKings.
When I joined the company, it was still early in its growth, and my team owned the data platform, which was the foundation that supported analytics across every part of the business. The breadth of problems to solve was enormous. We were supporting marketing, product, finance, fraud, compliance, risk, and sports analytics teams, each with its own complexity and pace. It was a challenge, but an incredible one.
What fascinated me was how data powered every part of the company. There was, and still is, an enormous analytics organization driving insights across all of these areas, which turns raw data into data intelligence and data products that are critical to the success of the business. Coming from e-commerce, that level of speed and interconnection in sports betting was a bit of a shock! Sports data is volatile and fast, and I loved turning that volatility into high-quality, speedy, and reliable building blocks that other people could anchor to and ship products on.
What’s a data point (or points) more bettors should be paying attention to when betting?
Elaine. Over the years, I’ve learned a ton from really great DFS players, sports bettors, and friends who always have many opinions, and it’s helped me refine my own strategies. Here are two areas worth keeping on the radar.
I like to look at a few things that aren’t as common or easily accessible (and yes, that’s a bit of a pitch toward Betflow’s data!). Some trends show performance over time, but I like to slice and dice across a bunch of dimensions like weather, grudge matches, days of rest, and other conditions that might signal where to dig deeper.
Preferred pace is another big one. It’s basically the tempo a team wants to play - fast, slow, or somewhere in between, and how often they actually get to play that way. It’s a great way to read how a game might flow. When a fast team can dictate tempo, they can run away with it. When a slower team falls behind, they often have to speed up, which changes everything. Games where those mismatches happen tend to swing totals, props, and live betting angles more than most people realize. Once you start watching for them, you’ll see how often they explain those “how the heck did that team go over?!” moments.
When you’re dreaming about the future of Odditt and Betflow, what’s something you’re really excited to build? What’s the north star?
Elaine. For me, it’s about deepening people’s connection to sports, teams, and players. I love the idea that someone could open Betflow, start exploring, and end up following a league they’ve never paid attention to before - maybe Finnish hockey, the DEL, Liga MX, the Brasileirão, or even the Irish Premier Division - because some emoji or trivia or stat caught their eye and made them curious. I’ve found myself doing the same thing; I’ve played those leagues this week, and honestly, I never would have otherwise. I see something new and interesting, and start digging deeper each time I open the app.
I want Betflow to make that kind of discovery feel natural and fun and not at all like homework. Some days you might dig into stats; other days, it’s been a long day and you just want to build a ridiculous long-shot, random, emoji-driven parlay to sweat and dream like a lottery ticket.
I’m excited to keep building Betflow with more leagues, more community, deeper personalization, and to spread it globally - so fans and soon-to-be-fans everywhere can find something new, learn a lot, and enjoy the experience each time they open the app.
What do women want in sports betting?
Elaine. Women want what most bettors want: something that feels clear, intuitive, and actually works the way people think. But women aren’t a singular audience. Some serious bettors build models and dig deep into data, and there are people who are just curious or looking for a fun way in, and the spectrum of folks in between. I want to build an app that does justice to all of them.
A lot of betting apps feel loud or chaotic. I think there’s real value in products that are calm, direct, and easy to explore, where you can see the data clearly if you want it, but you’re not forced through noise or complexity to get there. That clarity makes the experience more inviting and accessible, especially for anyone new to it.
One of the biggest things we focus on is making betting feel understandable. We use integrated tooltips that explain what’s happening in plain language and make sure people have resources to learn as they go. We also use tags like “Likely,” “Possible,” and “Longshot” to show risk and reward at a glance without needing to know how to read different odds formats. The goal is to build confidence and curiosity at the same time, so people can explore, learn, and have fun without feeling lost.
