Full TimeEN
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
The Executive Scheduler owns end-to-end scheduling for our two founders across all business and personal commitments. You are the single point of contact for all inbound scheduling requests — internal and external — and you are responsible for managing them from first inquiry through confirmation, reminder, change, and follow-up. You operate in real time, you communicate with clarity and speed, and you bring genuine judgment to every decision about how the principals' time is allocated.
You will report to and work closely with the Chief of Staff, and will collaborate daily with executive team. You are not an EA — but you need to work fluidly and without ego alongside that team, sharing information and coordinating logistics in real time. This is a career role for someone who takes scheduling seriously as a discipline — who finds genuine satisfaction in bringing order to complexity, who is energized by the pace and stakes of working at the top of a high-performing organization, and who wants to build something lasting. The right person will be deeply organized, technically curious, and able to absorb a very high degree of context about two principals' lives and priorities in order to make smart, independent decisions every day.
Your Responsibilities:
Serve as the first point of contact for all business scheduling requests for Jenny and Matt — internal and external — and own each request through to resolution.
Respond to scheduling inquiries promptly and proactively, never leaving requests in limbo. When something can't be confirmed immediately, acknowledge receipt and provide a clear timeline.
Maintain a thorough, real-time understanding of both principals' calendars, priorities, and constraints — so that every scheduling decision reflects their actual needs, not just open time slots.
Manage the full lifecycle of every meeting: request intake, coordination with all parties, confirmation, pre-meeting reminders, day-of logistics, and post-meeting follow-up as needed.
Apply strong prioritization judgment across competing requests, weighing business priorities, personal commitments, travel logistics, energy, and the principals' stated preferences to make smart recommendations.
Proactively identify conflicts, sequencing issues, or gaps in the schedule and surface solutions before they become problems — don't wait to be asked.
Maximize time in key cities (Austin, Chicago, New York) by clustering related meetings and commitments intelligently when Jenny and Matt are traveling.
Build and maintain scheduling trackers and dashboards that give the broader executive team clear, shared visibility into the status of all scheduling items — confirmed, pending, changes in flight, and outstanding follow-ups.
Actively explore and implement AI and technology tools to make scheduling workflows faster, more accurate, and easier to manage at scale.
YOUR EXPERIENCE
3–6 years of experience in executive scheduling, calendar management, or high-level administrative coordination — ideally supporting multiple senior executives simultaneously.
Prior experience working with high-profile, high-demand executives in a fast-paced environment. Familiarity with the rhythms, sensitivities, and protocols of supporting founders, C-suite principals, or similarly prominent individuals is a meaningful advantage.
Experience navigating private air travel logistics, high-profile external relationships, and confidential scheduling matters is strongly preferred.
Active and curious user of AI tools — you use them in your own workflow already and are excited to apply them to scheduling systems and team coordination.
Expert-level proficiency in Google Calendar and Google Suite (Gmail, Docs, Sheets, Drive).
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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