Chief of Staff

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