Head of Commercial Strategy and Operations

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—empowering solo and small group practitioners to thrive alongside their clients. Recognized by MedTech Breakthrough as the Best Practice Management Solution Provider in 2024 and the Digital Health Awards in 2023, SimplePractice is proud to pave the future of mental health tech. The Role We are seeking a strategic and operationally strong leader to own end-to-end revenue and commercial strategy and operations across Sales, Onboarding, Account Management, and Customer Support. This role owns the systems, processes, and operating cadence that run these functions today, and leads the strategy and execution behind where they need to go next. Reporting to the Chief Commercial Officer, the ideal candidate brings real strategic depth alongside direct, hands-on execution experience in customer facing functions, and is comfortable both setting direction and running the operating machinery themselves. Responsibilities Own Revenue Strategy and Planning: Partner with the CCO to set commercial and revenue strategy, and translate it into annual and quarterly plans across Sales, Onboarding, Account Management, and Support. Own End-to-End Revenue Operations: Directly own the systems, tooling, processes, and reporting infrastructure that run Sales, Onboarding, Account Management, and Support, including pipeline management, forecasting, and handoffs between functions. Diagnose and Rebuild Customer Facing Functions: Assess what's driving current performance in a given function, for example what's behind today's Support satisfaction and churn dynamics, then design and lead execution of the operating model the function needs going forward. Build and Own the Customer Lifecycle View: Develop a holistic view of onboarding and product adoption across the customer lifecycle, and partner with Product and Marketing to design and execute a lifecycle expansion plan. Run the Commercial Operating Cadence: Own business reviews, KPI reporting, and follow-through on decisions for the commercial leadership team. Lead AI Strategy for Revenue Operations: Identify and lead the build-out of AI powered workflows across Sales, Onboarding, Account Management, and Support, drawing on direct prior experience implementing AI tools, not just evaluating vendors. Drive Cross-Functional Alignment: Partner closely with Product, Marketing, Finance, and other functions to align on shared goals, and influence outcomes without direct authority over every team involved. Present to Senior Leadership: Provide regular updates and strategic recommendations to the CCO and executive team on commercial and revenue performance. Desired Skills & Experience Experience: Minimum 10 years in strategy, revenue operations, or commercial operations, with direct experience owning functional execution such as Sales Operations or Revenue Operations. Strategic and Operational Range: Strong strategy background paired with a real track record of running revenue operations end-to-end, not just advising on it. Track Record of Execution: Demonstrated ability to execute strategy within and across teams and see it through to results. Customer Facing Process Background: Direct, firsthand experience building and running operational processes inside customer facing functions such as Sales, Support, Onboarding, or Account Management. AI Implementation Experience: Direct, firsthand experience building or rolling out AI powered processes or tools inside a business function, with real adoption results. Cross-Functional Influence: Comfortable working across t…