Executive Assistant

Kin is redesigning insurance to be smarter, faster, and centered on the customer. We use intelligent pricing, offer seamless bundling, and make every step (from purchasing, servicing to claims) simple and friction-free, especially in the places traditional insurers often ignore.

We empower people to protect what matters most, starting with their homes and expanding to all they value, in a world where climate risks, rising costs, and outdated systems leave too many behind. Our approach has fostered amazing growth, attracted marquee investors, and earned us accolades, including being named to:

• Built In Chicago's Best Places to Work, Midsize Companies (2021-2025).

• Forbes' America's Best Startup Employers (2021- 2024, Ranked #37 in 2024).

• Inc. 5000 Fastest-Growing Private Companies.

• Forbes’ Fintech 50.

Simply put, our people are what make us great – we need forward-thinking, inspired game-changers like you to join us in our mission.

So, what’s the role?

We are looking for an Executive Assistant who will be a true force multiplier for both the CEO and the executive team. This is not just about scheduling meetings and booking travel. This role is about creating leverage, making sure the CEO is focused on the highest-impact work, and enabling the Chief of Staff to scale leadership priorities across the company.

The right person will thrive in a fast-paced environment, know how to operate with judgment and discretion, and take pride in making complex operations look simple. You’ll be embedded in the center of our executive team’s workflow and will play a key role in ensuring the company runs smoothly at the top.

This role is based in Chicago with an expectation of 2–3 days a week in the office.

Core Capabilities

• Organizer: Keeps operations tight, with systems and processes that prevent things from slipping through the cracks.

• Problem-Solver: Anticipates challenges and resolves them before they escalate.

• Communicator: Clear, crisp, and professional in both written and verbal communication. Able to represent leadership effectively.

• Trusted Partner: Handles confidential matters with discretion, maturity, and sound judgment.

• Tech-Savvy: Highly proficient in Google Workspace, Slack, Navan, and willing to adopt productivity tools like ChatGPT/Claude to increase leverage.

What You’ll Own

Calendar & Scheduling

• Fully own and optimize the CEO’s calendar.

• Anticipate and resolve conflicts before they become issues.

• Protect time so priorities, not noise, drive the agenda.

Communication & Coordination

• Serve as the first line of triage for inbound requests to the CEO, Chief of Staff, and executive team as a whole.

• Ensure timely and accurate communication with internal leaders, external partners, board members, and investors.

• Draft and polish communications when needed.

Meetings & Travel

• Prepare agendas and ensure pre-read materials are distributed.

• Capture notes, track action items, and track outcomes/completion.

• Manage all travel logistics end-to-end for the executive team.

• Effectively manage logistics for in-person board and investor meetings.

Project & Task Management

• Track and follow through on key deliverables across the executive team.

• Partner with the Chief of Staff to keep executive operating rhythms (executive meetings, board prep, all-hands) running smoothly.

• Spot where processes can be tightened and improve them.

Confidentiality & Discretion

• Handle sensitive information, conversations, and decisions with the highest level of professionalism.
  

What Success Looks Like

Within the first 6–12 months, success in this role means:

• The CEO’s calendar consistently reflects strategic priorities

• The Chief of Staff is spending the majority of their time on strategic projects, not chasing follow-ups

• Board meetings, leadership meetings, and external engagements are well-prepared, seamless, and productive

• Action items don’t get lost; follow-through is consistent

• Executives and staff alike feel the benefit of clarity, focus, and efficiency

• Executives feel appropriately supported with calendars, travel, and deliverables

What We’re Looking For

• 7+ years of experience supporting a CEO and/or senior executives

• Strong organizational systems; ab