VP of Enterprise Operations

SimplePractice; Oregon; Hybrid; USD 270,000 - 315,000; Full time

Benefits offered by this job

Medical, dental, vision

Life & disability insurance

401(k) match

Flexible Time Off

Parental leave

Mental health resources

Tuition reimbursement

Job summary

SimplePractice, LLC in the United States seeks a seasoned VP of Enterprise Operations to own the executive operating system, planning processes, and AI-enabled workflows. You will shape decision forums, align the ELT with ambitious priorities, and ensure timely execution while surfacing tradeoffs across the organization.

You will drive the integrated operating system end-to-end, partner with finance on resource envelopes, and lead cross-functional initiatives that scale a fast-growing software

Qualifications

• Minimum 10 years in Business/Enterprise operations, including running an annual planning cycle end-to-end at a software company.
• Proven track record of running a board cycle with private equity or growth equity investors.
• Experience holding senior operating or business-operations leadership seats (not staff/advisory).
• Demonstrated ability to hold senior executives accountable while maintaining strong peer relationships.
• Experience eliminating unnecessary meetings, reports, and processes to improve efficiency.
• Hands-on experience redesigning operational workflows using AI tools.
• Strong financial literacy to partner with Finance on resource envelopes and reallocation.

Responsibilities

• Run the ELT operating system: design and operate the forums used to decide and align leadership.
• Audit recurring executive meetings, write the ELT charter, maintain commitments log, frame recommendations, elevate cross-functional issues.
• Own the integrated planning process: connect long-term ambition to annual priorities, OKRs, and quarterly reallocations.
• Manage calendar sequencing and templates to ensure strategic decisions precede budgets and align plans.
• Run the board operating process: calendar, agenda architecture, and narrative across strategy, performance, finances, talent and risk.
• Prepare materials for the CEO and executives, anticipate board questions, track follow-ups, coordinate with investors.
• Redesign the AI-native executive operating system to improve signal, preparation, memory, and accountability.
• Lead select special projects: manage cross-functional, time-bound initiatives with clear charters and handoffs.

Skills

Business operations

Annual planning

Board cycle management

Cross-functional leadership

AI tools in operations

Financial literacy

Tools

AI tooling in ops

Job description

About Us

At SimplePractice, we are improving access to quality care by equipping health and wellness clinicians with all the tools they need to thrive in private practice.More than 250,000 providers trust SimplePractice to build their business through our industry-leading software with powerful tools that simplify every part of practice management. From admin work to clinical care, our suite of innovative solutions work together to reduce administrative burden and empowering solo and small group practitioners to thrive alongside their clients.Award-winning and people-first, SimplePractice is shaping the future of health tech. In 2026, we were recognized by BuiltIn as a Best Remote Company to Work For, Software Guru's Best Places to Code, Becker Healthcare Telehealth Companies to Know, and we won a MedTech Breakthrough Award for Best Practice Management Solution Provider.

The Role

We are a $400M+ ARR vertical SaaS and AI company serving solo and small healthcare practices, with a plan to double over the next three to five years. We are in building mode, and we want a culture of speed: process exists only where it makes a decision faster or removes a blocker.

The VP Enterprise Operations is the CEO's partner for how the company runs at the top. You own the executive operating system: which forums exist, what gets decided in each, what information they need, how tradeoffs get surfaced, how commitments are tracked, and how the CEO's time maps to enterprise priorities.

You own the integrated planning process, the board operating process, and the AI-native tooling underneath all three. You are a full member of the executive leadership team (ELT) and you report to the CEO.

What the role is not: you do not own functional results, originate corporate strategy, or break ties between executives. The functional leaders own their results, the CEO and ELT own strategic choices, and the CEO breaks ties. Your job is to make sure the choices get made, on time, with the tradeoffs visible, and that what was decided actually happens.

Responsibilities

Run the ELT operating system:Design and operate the forums the ELT uses to decide and to hold itself accountable.

Audit recurring executive meetings to cut what does not earn its time, write the ELT charter that sets decision rights and commitment norms, maintain the central commitments-and-decisions log, ensure decision items arrive framed with recommendations, and elevate open cross‑functional issues to the CEO.

Own the integrated planning process:Connect company choices into one coherent system from long‑term ambition to annual priorities, departmental plans, OKRs, and quarterly reallocation.

Own the calendar, sequencing, and templates, ensuring strategic choices are made before budgets are built and reconciling functional plans across the enterprise.

Run the board operating process:Own the annual board and committee calendar, agenda architecture, and the integrated narrative across strategy, operating performance, financials, talent, and risk.

Assemble materials, prepare the CEO and executives, anticipate board questions, track follow‑ups, and coordinate with investors.

Serve as business owner of the AI‑native executive operating system:Redesign executive workflows so AI improves signal, preparation, decision memory, and accountability (e.g., weekly ELT briefs, KPI commentary, commitment tracking, strategy‑to‑OKR traceability, board materials consistency and scenario analysis).

You decide what gets built, in what order, and drive adoption.

Lead select special projects:Manage time‑bound, CEO‑sponsored, enterprise‑level initiatives that cross functions and affect the value‑creation plan, each with clear charters, success measures, and handoff plans.

Desired Skills & Experience

• Minimum 10 years in Business/Enterprise operations including direct experience running an annual planning cycle end to end at a software company.
• Proven track record of running a board cycle with private equity or growth equity investors.
• Experience holding real operating or business‑operations leadership seats (not exclusively staff or advisory roles).
• Demonstrated ability to hold senior executives accountable to commitments while maintaining strong peer relationships.
• Experience eliminating unnecessary meetings, reports, and processes to streamline organizational efficiency.
• Hands‑on experience personally redesigning operational workflows using AI tools.
• Strong financial literacy to partner effectively with Finance on resource envelopes and reallocation.

Bonus Points

• Early career background in management consulting or investment banking.
• Experience running an annual planning cycle end to end at a SaaS technology company with 200M‑1B in ARR.
• Experience with small‑business customers, self‑serve growth models, or healthcare technology.
• M&A integration exposure.
• Previous experience acting as a product owner for internal tools.

Benefits

We offer a competitive benefits program including:Medical, dental, vision, life & disability insurance401(k) plan with company matchFlexible Time Off (FTO), wellbeing days, paid holidays, and summer FridaysMental health resourcesPaid parental leave & Backup CareTuition reimbursementEmployee Resource Groups (ERGs)

California Job Applicant Privacy Notice

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 privacy practices, please contact us at .

Base Compensation Range$270,000—$315,000 USD