Head of Customer and Commercial Operations

Pearl Health

7d•$220,000 - $240,000•Hybrid

About The Position

Pearl Health is dedicated to empowering primary care providers, health systems, and physician-led networks to succeed in the shift to value-based care. Our platform delivers the technology, financial tools, and expert services that enable practices to provide more proactive, effective care to their Medicare patients, ultimately lowering costs and improving health outcomes. Founded in 2020, we are backed by premier investors including Andreessen Horowitz, Viking Global Investors, and AlleyCorp. We partner with thousands of providers across 44 states to build a more sustainable future for American healthcare. The Head of Customer and Commercial Operations owns the full client lifecycle: from initial VBC assessment and business development support through onboarding, performance enablement, and long-term retention. This is not a traditional customer success leader role. It requires someone who can build the systems, relationships, and teams needed to drive measurable outcomes at every stage of the client relationship. We are looking for someone who understands that, in a risk-based model, performance and satisfaction are the same thing, and someone who can build the operating infrastructure to prove it. This role owns a unified commercial operations function spanning Growth Ops and Customer Success. The right person will mature the function from pipeline management to full-lifecycle VBC enablement: connecting first-introduction insights directly into post-sale transformation activities. This is a senior hire with a COO-level scope of impact. The Head of Customer and Commercial Operations reports to the National President and operates as a key member of the commercial leadership team. The CS function continues to operate in a matrixed model alongside regional Market Presidents to support the full client portfolio.

Requirements

The ideal candidate bridges two archetypes that are often hired separately: a senior relationship executive who is credible at the highest levels of a health system, and a systems-oriented operator who builds scalable infrastructure. We are looking for someone who holds both.
Senior enough to be the most credible relationship manager in the room with C-suite and clinical leaders at large health systems
Systems-design instinct: recognizes when manual workflows need to be codified and drives the team toward scalable solutions, without needing to build them personally
Genuine dual mandate: holds the conviction that driving performance in value-based care is the path to client satisfaction, not in tension with it
A strategic operator: capable of providing the execution layer with context, prioritization, and the 'so what' that calibrates how work gets done
10+ years in a high-performing healthcare customer success, market, or provider-facing leadership role
Deep fluency in value-based care, Medicare programs (MSSP, ACO REACH), and the clinical and financial levers that drive performance in risk-based contracts
Experience at an ACO, health system, or healthcare technology company operating in the value-based care space is strongly preferred
Track record of scaling a team and function while maintaining service quality and increasing operational efficiency
Experience leveraging data and internal dashboards to develop strategy, identify performance risks, and drive accountability
Demonstrated ability to present to and influence clinical and executive-level leadership
Comfort operating in a matrixed environment where influence matters as much as authority
Willingness to travel for in-person client engagement (up to 25%)

Responsibilities

Own the client relationship from first introduction through long-term performance: including initial VBC readiness assessment, business development support, onboarding, performance enablement, and retention
Partner closely with Market Presidents, who lead growth and own the P&L, to ensure a seamless transition into post-sale onboarding, performance management, and long-term client success
Design and own the operating model that connects pre-sale intelligence directly into post-sale transformation activities, eliminating handoff gaps between growth and customer success
Ensure that insights gathered during early client engagement inform program deployment, and that post-sale learnings feed back into growth strategy and pipeline qualification
Own a unified commercial operations function spanning Growth Ops and Customer Success, including pipeline systems, playbooks, tooling, and post-sale transformation infrastructure
Drive the shift from manual, relationship-dependent workflows to codified, scalable systems, including tooling, playbooks, and automation that reduce operational risk and compound institutional knowledge
Build and own the feedback loop: translate issues, escalations, and performance patterns into durable rules the team acts against consistently
Provide strategic leadership over the integration and evolution of Growth Ops and CS Ops into a single, high-functioning commercial engine
Own the day-to-day client relationships, developing and executing engagement and remediation plans in a high-touch or scaled manner as appropriate, activating the broader organization in a coordinated manner
Establish and hold a clear operating philosophy: performance in value-based care is the mechanism for client satisfaction, not a trade-off with it
Partner with the Performance function leadership team on programmatic design, and own the team and operational infrastructure that deploys those programs at the account level. This is a builder role, not a coordination role
Serve as the primary interface between clients and the Performance vertical, owning the feedback loop that informs program development, operational priorities, and outcome measurement
Own NPS as a lagging indicator of performance and engagement quality, not as a primary objective in isolation, and design feedback mechanisms that surface signal from the full client base
Serve as the most senior relationship manager on the team, credible with C-suite and clinical leaders at enterprise accounts as a player-coach or direct owner of key relationships
Recruit and build the right team to implement performance improvement programs, owning both the talent and the execution model
Lead and develop a team of CS and Growth Ops professionals and leaders, providing the strategic context and prioritization guidance that translates execution to outcomes
Partner closely with Market Presidents and their teams on key clients, portfolio strategy, renewals, and cross-sell opportunities within a matrixed commercial model
Serve as an escalation point for complex client challenges, partnership disputes, and renewal negotiations
Own the annual retention target, including renewal contract execution, escalation strategy, and negotiation enablement
Partner with Performance, Finance, Markets, and Product teams to align performance improvement plans with contractual outcomes
Drive cross-sell and expansion motions within the existing portfolio in coordination with Market Presidents
Own end-to-end strategy and execution for the digital-first client segment, building a scalable, lower-touch model that leverages automation and product-led engagement
Define segment-specific processes, service standards, and metrics distinct from enterprise relationship management