Head of Revenue Operations

The posting, as Casechek wrote it

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

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

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

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

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

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.

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

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.

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

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

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

Data-driven and insight-oriented; able to turn complex data into clear recommendations that leadershi
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, and comfort working hands-on as an individual contributor while building a team over time

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

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

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

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

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

Why You'll Love Working Here

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

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

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

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

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

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

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

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

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