Chief Revenue Officer (CRO)

Siftwell Analytics•Charlotte, NC

2d•Remote

About The Position

As Chief Revenue Officer (CRO), you will be joining a company that has found product-market fit and is executing on an effective go-to-market, with ARR growing 2x – 3x YoY. You will lead Siftwell’s next phase of growth, building and scaling a high-performing, enterprise GTM engine as the company approaches Series A. Reporting directly to the CEO, you will own how Siftwell competes, wins, and grows in a complex healthcare market. This is initially a player–coach role. You will step into an active, founder-led sales motion alongside the CEO and SVP of Growth, personally leading key enterprise opportunities while building the structure, rigor, and team needed to scale. You will manage, I develop and grow the existing team, hire additional sales leadership, and bring consistency and predictability to the overall revenue engine, with oversight of marketing to ensure strong alignment across positioning, demand generation, and enterprise sales execution. Success in this role requires both hands-on execution and strategic leadership, someone who can step into deals, coach teams, and shape how the company positions, sells, and expands within its market. You will operate in a complex, multi-stakeholder payer environment and bring a recognized presence and trusted relationships across the health plan ecosystem, including regional and national payers, Blues plans, provider-aligned plans, and key partners such as HPA networks and analytics vendors. This role operates primarily during U.S. Eastern Time business hours, with approximately 30-40% travel for client engagement and team collaboration.

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.

Nice To Haves

Experience selling care management, population health, analytics, SaaS, or workflow optimization products into health plans and other risk-bearing entities.
Experience strategically leveraging novel technology (e.g. AI) to enhance and automate the sales motion.
Familiarity with account-based strategies, payer segmentation, leveraging channel partnerships, and navigating procurement, contracting, and compliance pathways within regional and national health plans.

Responsibilities

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.