REMOTE - Senior CMS Business Development Lead at Wilcore Technologies Inc.

Wilcore Technologies is a Service-Disabled Veteran-Owned Small Business (SDVOSB) delivering digital services, software engineering, product management, and human-centered design to federal health agencies including VA, CMS, DHA, DoD, and SEC. Founded in 2024, Wilcore has grown from 6 to 77 employees in 15 months and is one of the fastest-growing SDVOSBs in federal health IT.

We hold an active Secret Facility Clearance and a growing credentials stack in quality, security, and process maturity. We are a SECAF Government Contractor of the Year finalist and are executing on a deliberate strategy to grow into a leading federal health IT prime contractor by 2029.

This is not a maintenance role. It is a growth role at a company that is genuinely building something.

The Opportunity

We are hiring our first dedicated CMS Business Development Lead — a senior professional who will own and build Wilcore's CMS pipeline from the ground up. This person will serve as the primary relationship owner within CMS, work in lockstep with our Director of Capture on every pursuit, and be instrumental in positioning Wilcore as a trusted digital services partner at one of the federal government's largest and most complex health IT buyers.

You will be the person who walks the halls of CMS, knows the stakeholders, understands the acquisition environment, and brings opportunities to the table that the rest of the team can execute against. If you thrive in a fast-growing company where your work directly shapes the company's trajectory, this role was built for you.

What You'll Do

Pipeline Development

• Own and build Wilcore's CMS opportunity pipeline from identification through qualification, with a focus on the Web and Emerging Technologies Group (WETG) and adjacent CMS program offices
• Identify, track, and shape opportunities 12–24 months in advance of solicitation using Shipley growth cycle principles
• Develop and maintain a rolling qualified pipeline that supports Wilcore's revenue growth targets
• Leverage AI-enabled market intelligence tools (e.g., GovWin, Bloomberg Government, or equivalent) to enhance pipeline visibility, competitive intelligence, and opportunity assessment

Relationship Management

• Cultivate and maintain active relationships with CMS program managers, contracting officers, and CORs — particularly within WETG and the Office of Acquisition and Grants Management (OAGM)
• Serve as Wilcore's face at CMS — attending industry days, capability briefings, and one-on-one meetings that create proximity to requirements before solicitations are released
• Manage teaming relationships with large primes and SDVOSB peers relevant to CMS pursuits

Capture Partnership

• Work in lockstep with the Director of Capture on all CMS pursuits — from opportunity identification through proposal submission
• Lead or support bid/no-bid decisions, capture planning, competitive landscape analysis, and win theme development
• Contribute to and review proposal sections, including executive summaries, management approaches, and past performance narratives
• Maintain CRM records and opportunity status reporting with discipline and accuracy

Strategic Growth

• Provide market intelligence and customer insight that informs Wilcore's CMS positioning, capability investments, and contract vehicle strategy
• Support positioning Wilcore for multiple award IDIQ vehicles relevant to CMS digital services work
• Identify and develop teaming arrangements that strengthen Wilcore's competitive position on target pursuits

What We're Looking For

Required

• 8+ years of federal business development experience, with a significant portion focused on CMS
• Active, existing relationships within CMS — specifically within WETG, OIT, or OAGM — that can be leveraged immediately
• Deep familiarity with the Shipley Business Development and Capture Lifecycle — from opportunity identification and shaping through proposal submission and debrief
• Demonstrated track record of winning federal digital services contracts at CMS or HHS
• Understanding of CMS contract vehicles including CMS SPARC, CMMI, GSA MAS IT, and related IDIQs
• Experience leveraging AI tools and digital market intelligence platforms to accelerate pipeline development and competitive analysis
• Ability to obtain a Public Trust clearance
• Willingness and ability to travel regularly to CMS facilities in Baltimore, MD and Washington, DC

Strongly Preferred

• Experience at or with SDVOSB, 8(a), or small business federal contractors
• Familiarity with CMS WETG's portfolio — including HealthCare.gov, Medicare.gov, and supporting digital infrastructure
• Experience in Agile and DevOps service delivery environments and the ability to speak credibly to technical delivery teams
• Knowledge of CMS acquisition cycles, procurement timelines, and key decision-making processes within OAGM
• Existing familiarity with or experience on CMS SPARC, MACBIS, or digital services task order vehicles
• Veteran status or demonstrated commitment to veteran-serving mission