Head of M&A, AI Services Roll-Up - Insurance BPO

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
ABOUT AI STRATEGIES
AI Strategies is the incubator group at PEAK6. We go after big new opportunities: (1) zero-to-one businesses built on PEAK6's fintech distribution, (2) software transformations, and (3) our latest thesis, AI services roll-ups, where we acquire services businesses and rebuild how they operate with AI. A central team of engineers at the cutting edge of applied AI is deployed across every initiative. We hire for entrepreneurial instinct and an insane work ethic, we bet on talented people early, and we put them on a track to lead. We are starting the roll-up in insurance BPO, and this role is one of the first hires to build it.
THE ROLE
You will source, underwrite, and close the acquisitions that build PEAK6's insurance BPO roll-up. You are a private equity or investment professional with a real insurance network, roll-up experience, and the conviction that AI is about to change what a services business is worth and how it is run. You will work directly with our applied AI engineers on the transformation case for every target.
As an early joiner you will hold equity in what we build, with upside that looks like a venture exit.
WHAT YOU'LL DO

• Build and own the acquisition pipeline: insurance BPOs, TPAs, and adjacent services businesses where AI changes the margin structure.
• Source directly through your insurance network, brokers, and outbound to owners ready to sell or partner.
• Lead diligence and underwriting with an AI-transformation lens, sizing with our engineers what automation unlocks in each business.
• Structure, negotiate, and close, then support integration into the platform.
• Shape the roll-up strategy: sub-sectors, sequencing, and what the platform looks like in three years.

WHO YOU ARE

• Private equity, investment banking, or corporate development background with hands-on roll-up experience. Having joined or built an existing roll-up is ideal.
• Deep insurance industry knowledge and relationships you can call on to find deals.
• You expect AI to reshape your own profession and want to be on the side doing the reshaping.
• Big ideas, insane work ethic, and the ambition to build something that lasts.

On experience: we would rather hand the reins to someone ambitious with two to six years of experience, give them real autonomy, and let them grow into the role than hire a résumé. We will also hire someone experienced, if they are at the point in their career where they want a defining challenge, are willing to fundamentally rebuild how they work with AI, and have something to prove. This is not a role for anyone who is not motivated by the size of the opportunity and the growth in scope that comes with it.
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 [email protected]. We will work with you to provide the necessary accommodations to ensure your full participation in our hiring process.
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