REMOTE - Senior CMS Business Development Lead

Wilcore Technologies Inc.

1d•Remote

About The Position

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. 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.

Requirements

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

Nice To Haves

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

Responsibilities

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
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
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
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