Executive Assistant

About the role

PEAK6 is a leading investment firm that uses technology to find better ways of doing things. Founded in 1997 with a tech‑based solution for options trading, the firm now applies that formula across industries, asset classes, and business stages to deliver superior results. 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. The Executive Assistant will support a leadership team whose work is externally facing — client meetings, sales cycles, partner relationships, and revenue‑driving activity. This is not a purely administrative role; you will act as a trusted extension of the executive(s), often serving as the first point of contact for clients and prospects, and must keep pace with fast‑moving deal cycles.

Responsibilities

• Manage complex, high‑volume calendars across multiple time zones, prioritizing client meetings, prospect calls, and internal commitments with sound judgment on trade‑offs
• Coordinate multi‑city and international travel, including last‑minute changes when client schedules shift
• Serve as a professional, polished first point of contact for clients, prospects, and partners — via phone, email, and in person
• Prepare and maintain CRM records (e.g., Salesforce, HubSpot); pull pipeline reports and prep materials ahead of client meetings, QBRs, and renewals
• Manage T&E, including client entertainment, gifts, and event‑related expenses, in line with compliance and budget guidelines
• Plan and coordinate client‑facing events: dinners, offsites, conferences, and trade show logistics
• Draft, proofread, and manage correspondence with external stakeholders, exercising discretion on what to escalate vs. handle directly
• Anticipate needs before they're voiced — from prepping briefing materials before a client call to flagging a scheduling conflict before it becomes a problem
• Maintain strict confidentiality around deal terms, pricing, competitive intelligence, and account‑level details
• Partner with sales operations, marketing, and other internal teams to ensure the executive is prepared for every external touchpoint

Requirements

• 3–5 years of experience as an Executive Assistant, ideally supporting sales, business development, client success, or other externally facing leadership
• Proficiency with CRM tools (Salesforce, HubSpot, or similar)
• Advanced calendar and travel management across multiple time zones
• Experience managing complex travel logistics, including international travel and visa requirements
• Expense management and T&E reporting, including client entertainment policies
• Event and conference coordination experience
• Executive presence — comfortable representing the executive and the brand in front of clients and prospects
• Fast, sound judgment under time pressure; able to make real‑time calls with limited information
• Strong relationship‑building instincts with people outside the organization, including cultural fluency for global clients
• Diplomatic communication style, especially when managing external parties who can't be