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The Role 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. Responsibilities: Executive Administrative Support 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. Meeting Infrastructure & Facilitation 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. Initiative Tracking & OKRs 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. AI-Enabled Operations 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. Culture & Events 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. Desired Skills & Experience 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 Exposure to Finance or People/HR functions is a plus — familiarity with concepts like close cycles, OKRs, or headcount planning will accelerate your ramp Benefits We offer a competitive benefits program including: Medical, dental, vision, life & disability insurance 401(k) plan with company match Flexible Time Off (FTO), wellbeing days, paid holidays, and summer Fridays Mental health resources Paid parental leave & Backup Care Tuition reimbursement Employee Resource Groups (ERGs) California Job Applicant Privacy Notic e Thank you for your interest in opportunities at SimplePractice LLC (“SimplePractice” or “us” or “we” or “our”). Please note that when you submit your resume or application materials to us for employment purposes, you are subject to the SimplePractice California Job Applicant Privacy Notice. For more information about our