Executive Assistant to the Founders

As we prepare for our next phase of growth, we're hiring an experienced Senior Executive Assistant to be the operational backbone of our executive team. This is a high-trust, high-autonomy role for someone who anticipates needs before they're voiced, protects our leaders' time, and keeps the details moving so the business can move faster. This role reports directly to the CEO and additionally supports our Co-Founder while working closely with the executive team, Chief of Staff, and People and Operations across the organization.

Responsibilities

Own complex, ever-changing calendars for the CEO and executive team, resolving competing priorities and protecting time for what matters most; Manage high-volume scheduling across time zones, including internal meetings, external partner sessions, board interactions, and interviews; Coordinate domestic and international travel end to end—flights, hotels, ground transport, and detailed itineraries; Prepare and process expense reports, reconciliations, and reimbursements with accuracy and on time; Plan and execute leadership offsites, team events, and board meeting logistics from concept through day-of run of show; Draft, proofread, and manage sensitive communications and documents on behalf of executives, handling confidential information with discretion; Partner with the Chief of Staff to prepare agendas, track action items, and follow up on decisions across leadership meetings; Serve as a welcoming, organized point of contact for internal teams and external partners interacting with the executive office; Drive ad hoc projects and process improvements that make the executive team more effective

Requirements

6+ years of executive assistant or administrative experience, including direct support of C-level leaders; Proven ability to manage complex calendars, travel, and logistics in a fast-moving environment; Exceptional organizational skills and meticulous attention to detail—nothing slips through the cracks; Strong written and verbal communication skills, with sound judgment about tone and audience; Discretion and integrity when handling confidential and sensitive information; A proactive, resourceful mindset—you anticipate needs, solve problems independently, and thrive amid ambiguity and shifting priorities; Fluency with modern productivity tools (Google Workspace, Slack, and expense/travel platforms)

Nice to have

You've worked in EdTech, healthcare, or another mission-driven industry; You've supported a founder or CEO at a high-growth startup

Benefits

Meaningful Equity Stake; Subsidized Medical, Dental, and Vision insurance plan options; 401(k); FSA, HSA and commuter benefits; Open vacation policy, including guidance of 15 days PTO annually; Stepful closed the last week of December; 15 work-from-anywhere days; 10 public holidays observed for 2026