Administrative Assistant; Scheduler

Overview

PEAK6 is a leading investment firm that uses technology to optimize business processes across industries. The company develops technology-driven solutions and seeks 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.

This role description outlines the responsibilities and qualifications for the Executive Scheduler who supports two founders. You will manage end-to-end scheduling for internal and external commitments, acting as the single point of contact for scheduling requests and coordinating with the principals’ calendars. You will report to the Chief of Staff and collaborate daily with the executive team. This is a demanding, career-level scheduling role requiring organization, judgment, and the ability to absorb context about two principals’ priorities to make independent decisions.

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, communicate with clarity and speed, and 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 the 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.

• 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.

• 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…