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 This Role
PEAK6 Trials is a brand-new program with massive potential - and you'll be on the ground floor. You'll have a front-row seat to some of the most ambitious fintech founders in the country, direct access to PEAK6's leadership and infrastructure, and the opportunity to build a program that could define how the next generation of fintech unicorns are created. At PEAK6, we see ambiguity as opportunity. If you do too, let's talk.
PEAK6 Trials is growing, and we need an operator to match our ambition. As Program Manager, you will be the organizational backbone of the Trials program. You'll be the connective tissue between our residents, internal teams, leadership, and external partnerships with VC/ startup ecosystem, ensuring every founder has what they need to move fast and build well.
This is not a coordinator role. This is a builder role - for someone who thrives in ambiguity, has a bias toward action, and can design structure where none yet exists.
What You'll Do
Program Architecture & Operations
Execute the operational framework for how PEAK6 Trials and Strategies teams runs day-to-day, including onboarding, milestone tracking, resource allocation, and reporting cadences
Build and own the systems, tools, and processes that keep the program organized and scalable as it grows
Develop and maintain a program playbook that can evolve as the program matures
Founder Support & Coordination
Serve as the primary point of contact for Trials residents, managing their access to PEAK6 internal resources (engineering, legal, compliance, business development)
Anticipate founder needs and proactively remove friction - connecting the right people at the right time
Track each resident's progress and surface insights and blockers to the Head of AI Strategies
Strategic Support to Head of AI Strategies
Act as a force multiplier for the Head of AI Strategies - owning projects, preparing briefings, driving follow-through, and representing the program in key meetings when needed
Help shape the program's long-term strategy by synthesizing learnings across resident cohorts and identifying areas for improvement
Manage the Head of AI Strategies' priorities by filtering, triaging, and executing on operational needs
Cross-Functional Collaboration
Coordinate across PEAK6 business units (Apex Fintech Solutions, PEAK6 Capital Management, Strategic Capital, etc.) to connect residents with the right internal resources and potential design partners
Maintain strong relationships with PEAK6 leadership and key stakeholders to ensure the program has ongoing organizational support
Partner with legal and compliance teams to ensure resident activities align with PEAK6's standards
Communications & Reporting
Own internal reporting on program health, founder milestones, and resource utilization
Draft communications on behalf of the Head of AI Strategies for internal and external audiences
Manage any external-facing program communications in partnership with PEAK6's marketing team
What We're Looking For
3+ years of experience in program management, operations, or chief of staff roles - ideally in a high-growth startup, venture studio, or financial services/fintech environment
Proven ability to build programs and processes from scratch with minimal direction
Exceptional organizational skills with a sharp attention to detail and the ability to manage multiple priorities simultaneously
A collaborative communicator who can work effectively across all levels of an organization - from residents to C-suite
Comfort operating in ambiguity; you see a gap and you fill it
Experience supporting senior leaders in a fast-paced, high-accountability environment
Genuine curiosity about AI, fintech, and entrepreneurship - you don't need to be a builder yourself, but you need to understand and respect the people who are
Strong judgment, discretion, and the ability to represent the program and its leadership with professionalism
Bonus Points
Familiarity with fintech, options trading, or financial technology broadly
Background in AI-adjacent industries or products
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 [email protected]. We will work with you to provide the necessary accommodations to ensure your full participation in our hiring process.
#PEAK6
Skills Required
- 3+ years of experience in program management, operations, or chief of staff roles
- Proven ability to build programs and processes from scratch
- Exceptional organizational skills with a sharp attention to detail
- Experience supporting senior leaders in a fast-paced environment
- Genuine curiosity about AI, fintech, and entrepreneurship
PEAK6 Compensation & Benefits Highlights
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Healthcare Strength — Health coverage includes medical, dental, and vision insurance alongside mental‑health resources and an Employee Assistance Program. Plan options such as PPO/HSA indicate a comprehensive healthcare offering.
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Retirement Support — A 401(k) with company match is explicitly highlighted as “robust.” This points to meaningful employer-supported retirement savings as part of the core package.
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Leave & Time Off Breadth — Time off includes “generous PTO,” paid holidays, and two paid volunteer days, with an eight‑week sabbatical available after long tenure. Paid parental leave and adoption assistance further expand the leave portfolio.
PEAK6 Insights
What We Do
PEAK6 is not your typical investment firm. Here, we build and invest in businesses that span from finance and insurance to esports and education — and we're always seeking new opportunities. We're not defined by one industry or market. We activate "what is" into "what ought to be" through world-class technology, operational excellence, and purposeful design. We're in the business of doing, creating, and building the world with innovation and democratization in mind. Our team of opportunistic thinkers are generating new ideas while constantly improving, refining, and activating past ones. At PEAK6, it's not just our investments that make use great, but our people that make us valuable.
Why Work With Us
Ordinary doesn't apply here. We look for people who aren’t afraid to take chances, who bet on themselves and do it with confidence. People that dream up big ideas and ways to execute them. Epic storytellers, nimble problem solvers, imaginative entrepreneurs, and change-makers are all welcome.
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PEAK6 Teams
PEAK6 Offices
Hybrid Workspace
Employees engage in a combination of remote and on-site work.
As a hybrid workforce, we offer our employees the ability to work remotely up to two days a week.















