Chief Revenue Officer – CRO

Role Overview

• Define and drive Siftwell’s revenue strategy, owning how the company wins in-market and scales, while maintaining full accountability for pipeline health, forecast accuracy, and enterprise deal conversion.
• Lead and orchestrate the full sales motion across the CEO, SVP of Growth, and broader team, ensuring alignment, clear ownership, and consistent execution.
• Personally lead and close high-impact enterprise deals, while advancing and supporting strategic opportunities across the team.
• Take ownership of the transition from a pre-Series A sales motion (which indexes on founder-led sales), bringing structure, visibility, and repeatability while effectively leveraging executive and cross-functional team involvement.
• Identify and resolve pipeline inefficiencies, improving deal velocity, conversion, and overall pipeline quality.
• Build and enforce a structured sales methodology and operating rhythm, ensuring disciplined qualification, accurate forecasting, and consistent execution.
• Lead, coach, and develop the growth/commercial team, elevating enterprise selling capabilities and preparing the organization to scale.
• Partner with Growth, Product, and Customer Success to align go-to-market strategy, refine value propositions, build and iterate upon ICPs, and drive expansion within payer organizations.
• Build the commercial foundation for scale, including playbooks, pricing, metrics, market expansion plan, tooling, and workflows to support growth through Series A and beyond.
• Provide clear visibility to leadership on pipeline, forecasts, and risks, while representing Siftwell with executive presence in key client and market interactions.

Requirements

• 15+ years of progressive experience in enterprise sales and commercial leadership, including ownership of revenue targets at a senior level (VP, CRO, or equivalent).
• Deep experience selling into health plans or risk-bearing healthcare organizations, with a strong understanding of how these organizations buy.
• Proven track record of personally closing complex, multi-million dollar enterprise deals within long sales cycles and multi-stakeholder environments.
• Demonstrated success in transitioning or scaling a sales function and bringing structure to founder-led or early-stage sales motions and driving improved predictability.
• Strong player–coach profile, with the ability and willingness to personally carry and close deals while developing and leading a team.
• Experience implementing and enforcing structured sales methodologies (e.g. MEDDICC) to improve qualification, forecasting, and execution.
• Background working in growth-minded, early-stage companies where commercial strategy, process-building, and execution matured in parallel.
• Experience selling care management, population health, analytics, SaaS, or workflow optimization products into health plans and other risk-bearing entities.

Benefits

• Comprehensive health, dental, and vision insurance
• Short-term disability coverage
• 401(k) retirement plan with company matching
• Unlimited paid time off to rest and recharge
• Opportunities for ongoing professional development and learning