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

As a Chief of Staff, you are the Principal's trusted operational partner — the person who keeps them organized, informed, and effective across their 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 their work. Think of yourself as the conductor of corporate and strategic processes — a credible representative internally and externally, and a thought partner the Principal can rely on to keep things moving.

This is a destination role, not a stepping stone. The ideal candidate has already done this job for an individual before — knows what the role really requires, and is ready to build their own function from day one. This person loves being a Chief of Staff and wants to be a long-term strategic and execution partner, not someone using this seat as a path to running a portfolio company.

What You’ll Do:

● Communications & Relationship Management: Monitor and triage inbound
communications, draft correspondence on the Principal's 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 the Principal's schedule reflects their 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 the Principal's 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, corporate development, or the family office world

● Prior experience as a Chief of Staff to an individual is highly preferred — rather that solely for a team or department — given the know-how it takes to build the function from scratch and be effective from day one

● MBA Preferred

● Markets fluency is non-negotiable. If you don't already follow the markets closely, you need to be genuinely excited to invest real time getting there — 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 the Principal credibly

● Calm under pressure; flags problems early and comes with solutions

● This is the destination, not a stepping stone — you love being a Chief of Staff and want to be a long-term strategic and execution partner, not a future portfolio-company CEO

● 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 the Principal's presence

● Occasional travel between Austin, Chicago, New York, and select conferences;
candidates based outside Austin will only be considered if based in Chicago or New York, and must be open to extensive travel — particularly in the first several months — to build the in-person relationship with the Principal

● Reports directly to the Principal, with a meaningful dotted line to one co-founder'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

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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