Executive Assistant (Operations Partner)

SimplePractice; United States; On-site; USD 90,000 - 125,000; Full time

Benefits offered by this job

Medical, dental, vision insurance

401(k) plan with company match

Flexible Time Off

Paid parental leave

Tuition reimbursement

Job summary

SimplePractice is seeking an Executive Assistant to provide comprehensive administrative support to the CFO and CPO. The role includes managing calendars, travel, and facilitating meetings while leveraging AI to improve efficiency.

The ideal candidate has over 4 years of experience in executive support roles and is proficient in Google Workspace and Slack. Competitive benefits include medical, 401(k), and flexible time off.

Qualifications

• 4+ years in an EA, Senior EA, or Operations role, ideally at a fast-growing company.
• Experience supporting C-suite or senior leadership across multiple functions.
• Track record of driving cross-functional workstreams to closure.

Responsibilities

• Manage calendars and travel for the CFO and CPO.
• Own agendas for leadership and full-team meetings.
• Maintain a tracker of key initiatives across organizations.

Skills

Calendar Management

Travel Coordination

Expense Processing

Meeting Facilitation

AI Adoption

Strong Communication

Tools

Google Workspace

Slack

Notion

Job description

The Executive Assistant provides comprehensive administrative and operational support to the CFO and CPO of SimplePractice. This pivotal role spans traditional EA duties— 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

• 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).

Base salary range: $90,000 – $125,000 USD.