About SureCost

SureCost is transforming pharmacy procurement and inventory management for healthcare organizations nationwide. Our platform helps pharmacies and health systems reduce drug spend, improve compliance, optimize purchasing workflows and gain real-time operational visibility across the procurement lifecycle. Trusted by thousands of pharmacies and healthcare organizations, SureCost delivers measurable ROI in one of healthcare’s most operationally complex and highly regulated environments.

As the company enters its next phase of growth, SureCost is expanding its enterprise go-to-market motion and seeking an experienced Chief Revenue Officer to help scale revenue operations, enterprise sales execution and organizational maturity.

The Opportunity

SureCost is seeking a highly analytical, operationally rigorous and execution-oriented CRO to lead the company through its next stage of commercial scale.

This is not a “vision-only” executive role. We are looking for a proven operator who has successfully helped scale a B2B SaaS company from approximately $10M to $60M+ ARR within a complex, regulated industry such as healthcare, pharmacy, life sciences, fintech or other compliance-driven environments.

The ideal candidate combines strategic thinking with deep operational discipline. They are highly data-driven, grounded in metrics and forecasting accuracy, and capable of building scalable enterprise GTM systems across sales, customer success and revenue operations.

This individual will partner closely with the CEO and executive leadership team to professionalize and scale the company’s enterprise revenue engine while maintaining a high-performance, accountable and customer-centric culture.

What You’ll Do

• Lead and scale all revenue-generating functions, including Enterprise Sales, Account Management/Customer Success and Revenue Operations

• Build scalable forecasting, pipeline management and operational reporting frameworks with a high degree of predictability and rigor

• Develop and execute enterprise GTM strategy focused on acute health systems, large pharmacy organizations and strategic accounts

• Establish operational excellence across the revenue organization, including KPI management, territory planning, pipeline hygiene and sales process optimization

• Partner cross-functionally with Product, Marketing, Customer Success and Implementation teams to improve customer acquisition, retention and expansion

• Recruit, develop and retain top-tier GTM talent while raising the overall performance bar across the organization

• Implement scalable systems, processes and organizational structure appropriate for the company’s next phase of growth

• Help evolve pricing, packaging, segmentation and enterprise sales strategy

• Drive executive-level customer relationships and strategic enterprise opportunities

• Deliver accurate forecasting and actionable insights to the CEO, leadership team and board

• Create a culture of accountability, operational rigor and continuous improvement

What We’re Looking For

• Proven experience as a CRO, VP Sales or senior revenue leader within a B2B SaaS company that successfully scaled from approximately $10M to $75M+ ARR

• Strong preference for experience in healthcare technology, pharmacy technology, life sciences or similarly regulated industries

• Demonstrated success building and scaling enterprise sales motions with complex, multi-stakeholder buying processes

• Deep operational and analytical rigor with strong command of:

  • forecasting,

  • pipeline analytics,

  • revenue operations,

  • sales process design,

  • and KPI management

• Strong executive presence with the ability to build credibility across customers, leadership teams, and boards

• Experience building and leading high-performing revenue organizations through rapid growth phases

• Strong pattern recognition around organizational scaling challenges and GTM evolution

• Highly reliable decision-maker with sound judgment and data-backed recommendations

• Ability to balance strategic leadership with hands-on execution

• Experience working closely with founders and executive teams in high-growth environments

• Strong recruiting and talent development track record

What Success Looks Like

In the first 12–24 months, this leader will:

• Accelerate SureCost’s expansion into larger enterprise health systems

• Increase forecasting accuracy and operational predictability

• Build a scalable enterprise sales infrastructure and process rigor

• Improve pipeline quality, conversion efficiency, and revenue visibility

• Strengthen cross-functional alignment across the customer lifecycle

• Recruit and develop a world-class revenue organization capable of supporting the company’s next stage of growth