Executive Assistant

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
We're looking for an experienced Executive Assistant to support a leadership team whose day-to-day work is externally facing — client meetings, sales cycles, partner relationships, and revenue-driving activity. This is not a purely administrative role. You'll be a trusted extension of the executive(s) you support, often serving as the first point of contact for clients and prospects, and you'll need to move at the pace of a deal cycle: fast, high-stakes, and occasionally with very little notice.The ideal candidate has supported client-facing or sales leadership before, is comfortable being "on" in front of external stakeholders, and can make sound judgment calls under time pressure without needing constant sign-off.
You'll be responsible for:
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
YOUR EXPERIENCE:
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 "managed" the way internal stakeholders can
Airtight discretion with deal-sensitive and client-sensitive information
High tolerance for ambiguity and last-minute change, without losing composure or organization
Proactive, anticipatory mindset — sees around corners rather than reacting
What Success Looks Like in the First 90 Days:
Full ownership of calendar and travel management with minimal escalation needed
Established rapport with key clients and internal stakeholders
Comfortable navigating CRM systems and pulling relevant reports independently
Demonstrated ability to handle a last-minute client fire drill calmly and effectively
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.
Base pay offered may vary depending on job-related knowledge, skills, experience, and office location. This position also may be eligible for a discretionary annual bonus in addition to a range of health & wellness benefits, enhancing your overall compensation package.
Base Salary Range
$80,040-$100,050
PEAK6 is proud to be an equal opportunity employer that does not discriminate on the basis of 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 hr@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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