Head of Revenue Operations

Casechek

11h•$160,000 - $190,000•Hybrid

About The Position

Casechek is seeking a hands-on, results-driven Head of Revenue Operations to own the systems, data, and processes supporting Sales, Marketing, Customer Success, and Customer Operations. The role will build the infrastructure for predictable pipeline, accurate forecasts, and measurable customer lifecycles, spanning enterprise health-system sales, facility and supplier onboarding, and expansion across health-system footprints. The Head of Revenue Operations will develop and run revenue operations strategy across acquisition, implementation and go-live, expansion, supplier enrollment and monetization, renewal, and retention. The role will own and evolve the commercial technology stack, connect product usage data to the CRM, build supplier-side operating models and reporting, and establish deal-desk, forecasting, planning, KPI, and win/loss processes. It will align commercial and product teams around shared definitions, handoffs, and lifecycle stages. The position begins as a hands-on individual-contributor role, with the opportunity to design and build the RevOps function over time. The Head of Revenue Operations reports to the President & Chief Growth Officer and works closely with Operations, Finance, Product, Engineering, Sales, Marketing, Customer Success, Implementation, and Legal. Casechek describes its culture as collaborative, self-motivated, and supportive of long-term growth and learning. The company is based in Chicago’s Fulton Market and supports a hybrid Chicago or remote national setup.

Requirements

10+ years in revenue, sales, or business operations.
5+ years leading a team.
Comfort working hands-on as an individual contributor while building a team over time.
Experience scaling revenue operations at a growth-stage B2B SaaS company.
Experience supporting complex enterprise sales motions with long cycles, multiple stakeholders, and procurement-heavy buyers.
Deep Salesforce expertise and hands-on experience with Pardot and Gong, including conversation intelligence, deal and forecast insights, and marketing-to-sales attribution.
Strong understanding of integrations, automation, data architecture, and practical AI use in go-to-market workflows.
Fluency in forecasting, SaaS metrics such as ARR, NRR, CAC, and LTV, and compensation and territory design.
Working knowledge of regulated-data environments, including HIPAA, BAAs, and SOC 2, and comfort partnering with Security and Legal.

Nice To Haves

Healthcare, health-tech, or hospital-facing enterprise SaaS experience is strongly preferred.

Responsibilities

Build and run a revenue operations strategy covering acquisition, implementation and go-live, facility-by-facility expansion within IDNs, supplier enrollment and monetization, renewal, and retention.
Own and evolve the go-to-market technology stack, including Salesforce, Pardot/Marketing Cloud Account Engagement, and Gong, and manage integrations with the Casechek platform, Google Workspace, and Slack.
Prioritize automation, a single source of truth, and adoption of commercial systems by the team.
Partner with Product and Engineering to bring platform usage data into the CRM, including cases processed, Bill Only volume, supplier adoption, and savings delivered, so expansion opportunities, renewal risk, and ROI are visible to Sales and Customer Success.
Build the operating model, data, and reporting for supplier enrollment, adoption, and revenue opportunities with medical device manufacturers and distributors.
Build a deal desk with Sales, Finance, and Legal to streamline pricing, quoting, approvals, and contracting, including health-system procurement requirements, GPO/IDN contracting nuances, BAAs, and security and vendor-credentialing reviews.
Partner with the President and Finance on bookings and ARR forecasting, territory and account planning, quota plans, capacity modeling, and compensation-plan design for enterprise sales cycles.
Define and report business metrics, including pipeline coverage and velocity, win rates by segment, time-to-go-live, net revenue retention, facility penetration per health system, and supplier adoption.
Partner with Product Marketing to establish a win/loss process and ensure loss reasons are consistently recorded in Salesforce.
Align Marketing, Sales, Customer Success, Implementation, and Product on shared definitions, handoffs, and lifecycle stages, especially the sales-to-implementation handoff.
Start as a hands-on individual contributor running RevOps directly, then design the function across systems, analytics, and deal operations.