Chief of Staff

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

Matt Hulsizer is Co-Founder and Managing Partner of PEAK6. As one of the firm's two principals, Matt plays an active role across PEAK6's capital markets activities, portfolio company oversight, external relationships, and dealflow. While each of PEAK6's operating companies has its own CEO, Matt provides strategic counsel and is deeply engaged in the investment decisions, partnerships, and key relationships that shape the firm's trajectory.

As a Chief of Staff, you are his trusted operational partner — the person who keeps him organized, informed, and effective across his business and personal priorities. This is not a purely administrative role, nor is it a pure strategy role. It sits in a deliberately productive middle: you will own the systems and communications that keep the principal sharp, while also contributing meaningfully to the substance of his work. Think of yourself as the conductor of corporate and strategic processes — a credible representative internally and externally, and a thought partner he can rely on to keep things moving.

This role is a genuine launching pad for someone with the ambition and follow-through to earn it.

What You’ll Do:

Communications & Relationship Management: Monitor and triage inbound communications, draft correspondence on his behalf, manage follow-ups, and maintain a living contacts log. Prioritize dealflow and relationship requests intelligently — understanding what's worth the principal’s time and what isn't.

Meeting Preparation & Execution: Prepare for every significant meeting — research the people, context, and background; attend when appropriate; and ensure outcomes and follow-ups are captured and actioned. Coordinate with the EA team to ensure his schedule reflects his true priorities.

Project & Priority Management: Maintain a clear view of active projects and commitments across business and personal domains. Own trackers, ensure accountability, and keep initiatives moving. Liaise with portfolio company contacts and external partners on defined workstreams.

Content & Brand: Support occasional LinkedIn posts or internal content. Light lift, but requires the ability to capture his voice accurately. Flag moments where visibility could add value internally or externally.

Personal Priorities: Work in coordination with the EA team (who manage personal/family/home logistics and travel booking) to ensure the full picture — work and life — is coherent and well-sequenced.

WHO YOU ARE

5–8 years of experience in a demanding professional environment with career exposure to investment banking, capital markets, consulting, or corporate development

MBA Preferred

Markets fluency is non-negotiable. A genuine understanding of and interest in capital markets is essential — those who don't have it or aren't actively building it won't thrive in this environment

Exceptional written communication skills and sharp judgment on when to act vs. escalate

Low-ego, results-oriented, and takes pride in follow-through

Comfortable in high-stakes rooms and able to represent Matt credibly

Calm under pressure; flags problems early and comes with solutions

Actively curious about AI tools — PEAK6 is a leading AI investor and expects this role to be an early adopter

Additional Details

Based in Austin, TX; in-office 3–5 days/week depending on Matt's presence

Occasional travel between Austin, Chicago, New York, and select conferences

Reports directly to Matt with a meaningful dotted line to Jenny Just's Chief of Staff, who will lead onboarding and operational oversight

Coordinates with the full EA team; this role sits above the EA function in scope and judgment — but executes across all levels without ego

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.

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 hrpeak6@peak6.com. We will work with you to provide the necessary accommodations to ensure your full participation in our hiring process.

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