Head of Product - AI Services Rollup

WHO WE ARE

We are PEAK6, a leading investment firm, using technology to find a better way of doing things. The company’s first tech-based solution was developed in 1997 to optimize options trading, and over the past two decades, the same formula has been used across a range of industries, asset classes, and business stages to consistently deliver superior results. Today, PEAK6 seeks transformational opportunities to provide capital and strategic support to entrepreneurs and forward-thinking businesses. PEAK6’s core brands include PEAK6 Capital Management, PEAK6 Strategic Capital, Apex Fintech Solutions, FOCUS, We Insure, Evil Geniuses, Poker Power, Zogo, and Bruce Markets.

ABOUT THIS ROLE

PEAK6 AI Strategies is the AI investment and company-creation arm of PEAK6.

We’re building what the next generation of services companies looks like: real businesses, with real customers and real revenue, re-founded around AI.

Backed by PEAK6’s P6 AI Strategies, we acquire and operate companies in the insurance services and BPO space — then rebuild their core workflows with agents, automation, and software until the economics look like a technology company, not a services firm.

You’d be the founding Head of Product: the technologist-operator who decides what we build, ships it into live operations, and owns the transformation roadmap across the platform. You’re not selling AI to an enterprise and hoping they adopt it. You own the enterprise.

This team is onsite and based out of our Austin HQ. For this role, we are also open to candidates in Chicago and NYC.

What you’ll do:

• Own the product. Define and ship the agentic platform that runs underwriting support, claims, policy servicing, and back-office workflows across our operating companies. You set the roadmap.
• Deploy forward. Spend real time inside the operating businesses — sitting with claims processors and ops managers, mapping workflows, finding the 20% of the work that’s 80% of the cost. Then build against it.
• Move the P&L. Your success metric isn’t feature adoption or NPS — it’s margin. Every launch should show up in unit economics within a quarter. You’ll have a direct line from “we shipped this” to “the business makes more money.”
• Shape the thesis. As we evaluate acquisitions, you’re in the room — assessing which businesses’ workflows are most transformable, and what the platform needs to absorb the next one faster than the last.

YOUR EXPERIENCE

• 2+ years product ownership experience
• You’ve built something from nothing — a startup, a side project with real users, a scrappy internal tool that became load-bearing. You know what it feels like when there’s no playbook and no one above you to ask.
• You have genuine technical depth: you prototype your own ideas, you can read the code, and you have strong intuitions about what current models can and can’t reliably do in production.
• You’re energized (not deterred) by unglamorous, high-stakes domains, because you know that’s where the margin actually lives.
• Ambition is the baseline. Your grit and follow-through are what make it real.
• You move fast, hold a high bar, and want to work directly with people who do the same.
• Ability to be in our HQ 5x a week if located in Austin.

OUR REWARDS

We offer a robust package of employee perks and benefits, including healthcare benefits (medical, dental and vision, EAP), competitive PTO, 401k match, parental leave, and HSA contribution match. We also provide our employees with a paid subscription to the Calm app and offer generous external learning and tuition reimbursement benefits. As a hybrid workforce, we offer our employees the ability to work remotely up to two days a week depending on the role. The base pay offered may vary depending on job-related knowledge, skills, experience, and office location. This position also may be eligible for a discretionary annual bonus in addition to a range of health & wellness benefits.

PEAK6 is proud to be an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex (including pregnancy, sexual orientation, and gender identity), national origin, age, disability, veteran status, marital status, or any other protected characteristic. Our hiring practices ensure that all qualified applicants receive fair consideration without regard to these characteristics.

PEAK6 is committed to creating an inclusive and accessible workplace for all candidates, including those with disabilities. We are dedicated to ensuring equal employment opportunities and providing reasonable accommodations to qualified individuals with disabilities. If you require reasonable accommodations to participate in the application or interview process, please contact our HR department at View email address on click.appcast.io. We will work with you to provide the necessary accommodations to ensure your full participation in our hiring process.

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