Executive Assistant (Operations Partner)

SimplePractice

8d•$90,000 - $125,000

About The Position

The Executive Assistant provides comprehensive administrative and operational support to the CFO and CPO. This pivotal role spans traditional EA excellence: calendars, travel, events and the operational infrastructure both teams depend on: meeting rhythms, initiative tracking, and OKR accountability. The right person actively uses AI to eliminate routine work while being a strong culture facilitator. We are hiring for two Executive Assistant roles, one to support the Finance and People & Culture teams and another to support GTM, Customer Success, and Clinical Strategy. While this description reflects the scope for Finance and People, we welcome candidates with a range of EA experience and backgrounds to apply.

Requirements

4+ years in an EA, Senior EA, Operations, Business Operations, or Chief of Staff adjacent role — ideally at a fast-growing company
Demonstrated experience supporting C-suite or senior leadership across multiple functions simultaneously
Track record of driving cross-functional workstreams to closure without formal authority
Genuine AI curiosity with hands-on adoption of emerging tools
Exceptional organizational instincts — builds structure where ambiguity exists
Strong communicator; comfortable influencing senior leaders without formal authority
Discreet with sensitive information. Low ego, bias for action
Proficient in Google Workspace, Slack, Notion or equivalent

Nice To Haves

Exposure to Finance or People/HR functions is a plus — familiarity with concepts like close cycles, OKRs, or headcount planning will accelerate your ramp

Responsibilities

Proactively manage calendars and travel for both executives, anticipating conflicts, protecting focus time, and ensuring both are prepared for every commitment.
Process expense reports accurately and on time.
Own agendas for all leadership and full-team meetings — gather topics in advance, synthesize priorities, and distribute pre-reads.
Facilitate leadership meetings; capture decisions in real time and maintain a living action item log with owners and due dates.
Surface open items and follow through to closure without being asked.
Maintain a living tracker of key initiatives across both orgs — flag risks and delays before they become surprises.
Own OKR submission and review cycles; hold leaders accountable for timely inputs.
Keep core documents current: OKRs, strategic priorities, and operating frameworks.
Automate repetitive work using AI — meeting summaries, agenda drafts, status reports, and follow-up tracking.
Model a modern, AI-augmented operating style and bring forward practical tool recommendations.
Plan and execute team offsites, quarterly events, and all-hands gatherings for both organizations.
Partner with L&D and Workplace to build meaningful, consistent culture moments throughout the year.
Collaborate with other EAs to share best practices and create cross-team connection.