Head of Revenue Operations

THE OPPORTUNITY

Casechek is on a mission to innovate the implant supply chain and bring greater transparency to the cost of patient care. From procurement to payment, Casechek automates workflows for vendor supported surgical procedures. Our Bill Only Solution provides a comprehensive system of record for Hospitals and Health Systems to manage the complexity of surgical cases with implantable medical devices, expose hidden expenses and surface revenue opportunities.

The Head of Revenue Operations owns the systems, data and processes behind Casechek's commercial organization: Sales, Marketing, Customer Success, and Customer Operations. You'll build the infrastructure that makes our pipeline predictable, our forecasts accurate and our customer lifecycle measurable. This covers how we land health systems through multi-stakeholder enterprise cycles, how we onboard facilities and suppliers, and how we expand across a health system's footprint. You'll report to the President & Chief Growth Officer and work closely with Operations, Finance, and Product.

Casechek is a highly collaborative environment, but our team is also self-motivated and works independently. We strongly believe that great ideas are not created in isolation! Our team interacts with our healthcare customers to understand their needs and ultimately deliver the best user experience as possible.

About Us

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Casechek is based out of Chicago’s Fulton Market, but we’re a hybrid, remote and in-person team.

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We are highly motivated and passionate about solving healthcare’s messiest problems with new technologies.

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We value diversity, curiosity, and a passion for learning. The team has a lot of advanced degrees and even a few professional musicians.

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Innovating the implant supply chain is a marathon and not a sprint – we support each other in long-term growth and value developing transferrable skills.

About You

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Hands-on and results-driven, with a builder’s mindset: comfortable rolling up your sleeves as an individual contributor while shaping the long-term direction of the function.

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Scrappy, organized, and resourceful; thrives in a fast-paced, high-growth environment where much of the infrastructure is still being built.

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Deep Salesforce expertise, with a strong grasp of how systems, data, and integrations fit together, and a practical approach to using AI and automation to work smarter.

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Excellent communication and collaboration skills; able to partner across Sales, Marketing, Customer Success, Product, Finance, and Legal to build processes people actually adopt.

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Experience supporting complex enterprise sales motions with long cycles, multiple stakeholders, and procurement-heavy buyers. Healthcare or hospital-facing experience is a plus.

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Strong business and financial acumen, including fluency in forecasting, SaaS metrics, and quota, territory, and comp design.

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Data-driven and insight-oriented; able to turn complex data into clear recommendations that leadership can act on.

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Service-minded toward the commercial team: seeks to understand what creates friction for sellers and customer-facing teams, and builds systems that make their work easier.

Responsibilities

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Revenue strategy across the lifecycle –  Build and run a RevOps strategy covering acquisition, implementation and go-live, facility-by-facility expansion within IDNs, supplier enrollment and monetization, renewal and retention.

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Commercial tech stack –  Own and evolve the GTM stack (Salesforce, Pardot/Marketing Cloud Account Engagement and Gong) and their integrations with the Casechek platform, Google Workspace and Slack. Prioritize automation, a single source of truth and adoption by the team.

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Product to revenue data –  Partner with Product and Engineering to bring platform usage into the CRM (cases processed, Bill Only volume, supplier adoption, savings delivered), making expansion, renewal risk and ROI visible to Sales and CS.

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Supplier-side revenue –  Build the operating model, data and reporting for the supplier side of the platform, including enrollment, adoption and revenue opportunities with medical device manufacturers and distributors.

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Deal desk and contracting –  Build a deal desk with Sales, Finance and Legal that streamlines pricing, quoting, approvals and contracting, including health-system procurement requirements, GPO/IDN contracting nuances, BAAs, and security and vendor-credentialing reviews.

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Forecasting and planning –  Partner with the President and Finance on bookings and ARR forecasting, territory and account planning, building and tracking quota plans, capacity modeling and comp plan design that fit 6–18 month enterprise sales cycles.

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KPIs and insight –  Define and report the metrics that run the business: pipeline coverage and velocity, win rates by segment, time-to-go-live, net revenue retention, facility penetration per health system, and supplier adoption.

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Win/loss analysis – Partner with Product Marketing to build a win/loss process and make sure loss reasons are recorded consistently in Salesforce.

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Cross-functional alignment – Align Marketing, Sales, Customer Success, Implementation and Product on shared definitions, handoffs and lifecycle stages, especially the sales-to-implementation handoff, where most value is won or lost.

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Build the team over time – Start as a hands-on individual contributor running RevOps directly, then design the RevOps function across systems, analytics and deal operations.

Requirements

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10+ years in revenue, sales or business operations, with 5+ years leading a team, and comfort working hands-on as an individual contributor while building a team over time

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Experience scaling RevOps at a growth-stage B2B SaaS company; healthcare, health-tech or hospital-facing enterprise SaaS strongly preferred

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Experience supporting complex enterprise sales motions with long cycles, multiple stakeholders and procurement-heavy buyers

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Deep Salesforce expertise, with hands-on experience in Pardot and Gong (conversation intelligence, deal and forecast insights, marketing-to-sales attribution), plus a strong grasp of integrations, automation, data architecture and practical AI use in GTM workflows

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Fluent in forecasting, SaaS metrics (ARR, NRR, CAC, LTV) and comp/territory design

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Working knowledge of regulated-data environments (HIPAA, BAAs, SOC 2) and comfort partnering with Security and Legal

Why You'll Love Working Here

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Competitive Salary & Annual Bonus – The base salary range for this role is $160,000-$190,000

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Opportunity for Long-Term Incentives (LTI)  – Be part of our success with equity or long-term incentive plans that grow with the company.

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401(k) Match  – Invest in your future with our generous matching program to help you build long-term financial security.

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Work-from-Home Flexibility  – Enjoy the freedom to work where you're most productive with a supportive hybrid (Chicago) or remote setup (National).

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Flexible Time Off (Unlimited PTO)  – Recharge and focus on what matters most with unlimited paid time off tailored to your needs.

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Parental Leave  – Take time to bond and care for your growing family with fully paid parental leave options.

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Comprehensive Medical and Dental Benefits  – Prioritize your health and well-being with premium plans for you and your family.

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Brand-New Pro-Level Laptop  – Equipped with top-tier tools and technology to set you up for success from day one.

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Annual Education Budget  – Expand your skills and knowledge with dedicated funding for courses, certifications, and learning resources.