[Hiring] VP of Enterprise Operations @SimplePractice

Role Description

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.
  • Escalate 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.
  • Reconcile 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.
  • 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.

Qualifications

• 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

• 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).