VP of Enterprise Operations

SimplePractice; United States; Remote; USD 270,000 - 315,000; Full time

Benefits offered by this job

Medical benefits

401(k) plan with company match

Flexible time off

Mental health resources

Parental leave

Tuition reimbursement

Employee Resource Groups

Job summary

SimplePractice LLC is seeking a VP Enterprise Operations to lead the executive operating system and drive aligned, data-driven decisions across the company. You will own the integrated planning process, the board operating rhythm, and AI-enabled workflows that accelerate execution at scale.

You will partner with the CEO and ELT to ensure commitments are tracked, decisions are surfaced with context, and cross-functional programs advance the enterprise priorities.

Qualifications

• 10+ years in business/enterprise operations with end-to-end annual planning in software
• Proven track record running a board cycle with PE/growth investors
• Experience holding senior operating leadership seats
• Ability to hold executives accountable while maintaining peer relationships
• Experience removing unnecessary meetings/reports to improve efficiency
• Hands-on design of operational workflows using AI tools
• Strong financial literacy for partnering with Finance on resources and reallocation

Responsibilities

• Run the ELT operating system: design forums, govern decision rights, log commitments, and surface tradeoffs for the CEO
• Own the integrated planning process from long-term ambition to OKRs and annual budgets
• Run the board operating process: calendar, agenda architecture, and narrative across strategy, performance, financials, talent and risk
• Be the business owner of the AI-native executive operating system: drive AI-enabled signal, prep, and accountability
• Lead select enterprise-wide projects with clear charters, milestones and handoffs

Skills

Annual planning

Board governance

Leadership roles

Accountability

Process optimization

AI workflows

Financial acumen

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 escape 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, decision‑memo preparation, 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 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 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 [e-mail].

Notice to Candidates

Base salary is one component of total compensation. Employees may also be eligible for an annual bonus or commission. Some roles may also be eligible for overtime pay.

The amount below represents the expected annual base compensation range for this job requisition. Ultimately, in determining your pay, we’ll consider many factors including, but not limited to, skills, experience, qualifications, geographic location, and other job‑related factors.

Base Compensation Range

$270,000—$315,000 USD