Chief Revenue Officer (CRO)

About Us Siftwell Analytics is a fast-growing company that combines healthcare operator expertise and artificial intelligence to equip managed care health plans with better insights to drive earlier and more precise health interventions for members. Siftwell was founded with a fundamental commitment to address the unique challenges faced by health plans, beginning with Medicaid, Marketplace, and Medicare plans, who are entrusted with the care of our most vulnerable and complex populations. At Siftwell, we hire “Humble Killers” – individuals with a deep commitment to the mission, high ownership, and low ego. We are committed to providing a mutually respectful work environment where diversity and inclusion are critical to our success. We seek to recruit, develop, and retain talented professionals from a broad range of backgrounds, and to foster a culture where individuals can grow, contribute meaningfully, and thrive. About the Role 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. 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. Requirements Required: 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. Preferred 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. Application Timeline and Details We anticipate the application window for this opening will close on: June 5th, 2026. Submission does not guarantee selection, and Siftwell reserves the right to modify or close the hiring process at any time. Only shortlisted candidates will be contacted. All applications will be retained for future consideration. Candidates advancing beyond initial screening will be asked to submit a brief executive video. Additional stages may include panel interviews, with select finalists invited to in-person meetings with senior leadership. Disclosures Location & Hiring Eligibility This role is remote within the United States. We have an established presence in CO, FL, MA, MD, NC, NJ, NY, PA, and TN, and candidates in these states are encouraged to apply. If you're based elsewhere in the U.S., we'd still love to hear from you, we evaluate out-of-state candidates on a case-by-case basis. This role operates primarily during U.S. Eastern Time business hours. Benefits Overview At Siftwell, we hire Humble Killers — talented, mission-driven teammates who value impact, collaboration, and ownership. Our goal is to support that commitment through competitive pay, meaningful equity, and benefits that promote well-being, growth, and flexibility. Full-time Employment Opportunities include: 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 Benefits may vary based on location and employment status. Equal Opportunity Statement Siftwell celebrates diversity and is proud to be an Equal Opportunity Employer. We consider all qualified applicants without regard to race, color, religion, sex, national origin, disability status, veteran status, or any other characteristic protected by law. Qualified applicants with arrest or conviction records will be considered in accordance with applicable laws, including the California Fair Chance Act. ADA Accommodation Statement If you require a reasonable accommodation during a selection process, please let us know through our general contact form or indicate this in your application. Security Requirements Adhering to the Company Security and Privacy Policies and the associated security standards Maintaining the security of the Information assets and resources to which they have been granted access Ensuring direct reports are aware of and adhere to Company Security and Privacy Policies Ensuring the security of information and managing risks to assets and resources owned by their functional area Ensuring that contractors, consultants, partners and other third parties under their sponsorship operate in compliance with Company policy Monitoring compliance related to business assets owned by their functional area and taking corrective action as necessary #Siftwell