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Chief of Staff, Care Transformation & Customer Enablement

175k – 233kSan Francisco, CABusiness OperationsRemote5+ YOE
Summary

Operates Care Transformation team infrastructure, builds enablement systems bridging Marketing and customer-facing teams, owns OKRs, dashboards, and operating rhythms. Requires 5-8 years in strategy/ops or enablement at high-growth B2B, healthcare familiarity, and operational rigor.

About the role

What You'll Do

  • Run the CT operating system. Own the meeting cadence, the agenda, the decision log, and the follow-through. Leadership syncs, all-hands, account reviews — you set the rhythm, prep the materials, and make sure the right people are in the room with the right information. No meeting happens without a clear purpose. No decision gets made without an owner. Nothing falls through the cracks because you are the person who catches it.
  • Give CT leadership real-time visibility. Build and maintain the dashboards, trackers, and weekly briefs that tell the CT leadership team exactly what's green, what's at risk, and what needs their attention — without them having to ask. Own the CT headcount model. Track the budget. Translate account pipeline into staffing plans. Keep the VP of CT oriented on the full portfolio at all times.
  • Own OKRs and improvement initiatives. Track the team's progress against CT OKRs, surface blockers before they compound, and drive the quarterly retrospectives that help the team learn from each cycle. Own the inventory of improvement initiatives from inception through completion. Be the person who asks: are we working on the right things?
  • Be the bridge between CT and Marketing. Build the operating rhythm that ensures CT teams receive information before they face customers — not after. That means owning a 4-stream sequencing model (company vision → product narrative → feature update → release note) so CTEs and CSMs know exactly when and how updates are coming. It means building and maintaining the centralized CT enablement hub: a single source of truth for messaging, pitches, battle cards, competitive positioning, and product context. The first concrete deliverable is a gold-standard inpatient pitch that does not currently exist.
  • Anticipate needs before they become urgent. QBR narratives, renewal messaging, product change explanations — the best version of the role means CT teams never have to scramble because you saw it coming. Within 30 days, establish a standing mechanism for CT to surface upcoming needs to Marketing. Within 60 days, demonstrate that you have anticipated and addressed at least two needs before anyone had to ask.
  • Own major moments. CT's operational contribution to HFMA Annual Conference (June 2026), ViVE, and similar events is yours. That means customer speaker prep, CTE briefing, and account-level message alignment — coordinated in advance, not the week before.

Who You Are

  • 5–8 years in roles that required both operating rigor and content or enablement judgment — strategy & ops at a high-growth B2B company, customer success operations, RevOps, or enablement leadership in healthcare tech.
  • Built something from scratch before — a team function, an information system, an operating cadence — in an environment that didn't hand it to you.
  • Familiar with health system sales cycles and the dynamics of enterprise post-sale relationships.
  • Strong written communicator. Can translate a complex product update into a crisp, audience-specific brief without losing fidelity.
  • Operationally literate: comfortable owning a dashboard, a budget tracker, a planning model, and an agenda simultaneously.
  • Moves work forward through clarity and trust, not positional authority.
  • Low ego and high follow-through.
  • Thrives in ambiguity.

Compensation

Base compensation range of approximately $175,000–$233,000 per year, exclusive of equity. Compensation philosophy prioritizes meaningful equity grants.

Skills
OKRsDashboardsOperationsEnablementCustomer SuccessRevOpsBudget TrackingStrategic PlanningCross-functional CollaborationHealthcare Tech
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