Director of Capture (CMS Focused)

Join Sky Solutions, LLC - Pioneering Digital Transformation Excellence!

Sky Solutions is a trusted partner in government contracting, empowering federal agencies with cutting-edge IT solutions. Our expertise spans AI-first enablement, advanced cybersecurity, digital transformation, low-code
o-code development, cloud solutions, and agile delivery. We simplify complex processes and deliver breakthrough results for federal clients through healthcare, financial services, and national security.

Position: Director of Capture, CMS

Location: Tysons Corner, VA Hybrid

Employment Type: Full-time

ABOUT THE OPPORTUNITY

Sky Solutions is seeking a seasoned Director of Capture to lead capture strategy across our CMS and federal health IT growth portfolio. This role will support strategic pursuits within the Centers for Medicare & Medicaid Services, with an immediate focus on mission-critical digital services, eligibility, appeals, case management, and modernization programs that directly impact millions of Americans.

This is a senior-level growth role with strong executive backing, visibility across the leadership team, and the authority to shape capture strategy, teaming, customer positioning, solution alignment, and win themes. The right candidate will not simply support pursuits; they will help define how Sky Solutions competes, positions, and wins within CMS.

ROLE OVERVIEW

The Director of Capture will drive the full capture lifecycle for high-value CMS and federal health IT opportunities, from early identification and qualification through proposal submission. This individual will lead capture planning, customer engagement, competitive analysis, teaming strategy, price-to-win coordination, and proposal readiness.

The role requires a strong understanding of CMS, HHS, federal health IT, small business competitive dynamics, and structured capture methodology. The ideal candidate has a proven record of shaping and winning federal health IT pursuits, including recompetes and opportunities involving entrenched incumbents.

KEY RESPONSIBILITIES
Develop and execute comprehensive capture plans aligned to customer priorities, opportunity timelines, competitive landscape, and Sky Solutions' growth objectives.
Lead capture strategy for CMS and federal health IT pursuits, including qualification, pursuit planning, customer engagement, competitive positioning, teaming, and proposal transition.
Engage with CMS stakeholders, industry partners, advisors, and the federal health IT contractor community to gather actionable market and customer intelligence.
Conduct competitive analysis, including incumbent assessment, SWOT analysis, price-to-win inputs, customer hot buttons, and discriminator development.
Build and manage teaming strategy by identifying, qualifying, and negotiating with subcontractors and teaming partners with relevant past performance and customer credibility.
Translate capture intelligence into proposal-ready win themes, solution concepts, staffing strategies, transition messaging, and evaluation-aligned discriminators.
Collaborate with executive leadership, technical leads, pricing, contracts, recruiting, and proposal teams to develop compelling, compliant, and competitive responses.
Lead internal capture reviews, brief executive leadership on pursuit status, and drive decisions around bid strategy, teaming, pricing posture, and solution positioning.
Maintain opportunity pipeline tracking and provide regular updates to leadership on capture progress, risks, gaps, and recommended actions.
Represent Sky Solutions at relevant industry events, conferences, partner meetings, and pre-solicitation activities.
REQUIRED QUALIFICATIONS

7-10+ years of GovCon business development, capture, or growth experience with a focus on federal health IT.
Demonstrated capture wins on CMS, HHS, or CMMI contracts in the $25M-$100M range.
Deep familiarity with the ACA Marketplace, eligibility systems, or CMS digital services ecosystem.
Experience leading recompete captures, including incumbent positioning, transition risk messaging, customer shaping, and price-to-win strategy.
Working knowledge of GSA MAS as a contract vehicle and small business competitive dynamics.
Proficiency in Shipley or equivalent structured capture methodology.
Strong relationship network within the federal health IT contractor community.
Ability to lead cross-functional pursuit teams and drive accountability across capture, solutioning, pricing, proposal, contracts, and staffing functions.
Excellent written and verbal communication skills, with the ability to brief executives, partners, and customer-facing stakeholders.
PREFERRED QUALIFICATIONS

Existing relationships within CMS, CCIIO, the Marketplace Appeals Group, or related federal health IT organizations.
Experience with Pega BPM, case management systems, eligibility systems, appeals platforms, or digital services platforms in a federal context.
Prior employment with, or competitive experience against, small, mid-sized, or large organizations supporting CMS programs.
Familiarity with WOSB, 8(a), HUBZone, and small business set-aside competitive dynamics.
APMP certification, Shipley training, PMP, or equivalent capture/proposal credentials.
Understanding of CMS IT governance, including ATO processes, CMS TRA, FISMA compliance, cloud security, and federal modernization requirements.
WHY THIS ROLE

Lead CMS capture strategy, not just proposal execution.
Shape Sky Solutions' positioning across CMS and federal health IT modernization opportunities.
Work with direct executive access and strong leadership support.
Influence teaming strategy, pricing posture, solution alignment, and win themes.
Own high-priority pursuits with meaningful impact on Sky Solutions' growth trajectory.
Join a collaborative team with experienced GovCon growth, technical, pricing, recruiting, and proposal professionals.
Competitive compensation with performance-based bonus opportunity tied to strategic outcomes.
WHAT SUCCESS LOOKS LIKE

Strengthened CMS pipeline with qualified, strategically aligned pursuits.
Improved capture discipline, opportunity qualification, and measurable win probability.
Development of strong customer, partner, and industry positioning within CMS.
Successful execution of capture strategy for priority CMS and federal health IT pursuits.
Securing one or more strategic CMS prime awards within 12-18 months.
Elevated visibility and positioning of Sky Solutions within CMS modernization initiatives.
Interested candidates should be prepared to discuss specific CMS or HHS capture wins, recompete strategy experience, customer engagement approach, and how they have helped displace or compete against entrenched incumbents.

COMPENSATION:

The expected compensation range for this position is $130,000 - $220,000 annually. Compensation is determined in good faith and may vary based on job-related factors, including relevant experience, skills, education, certifications, clearance level, labor category alignment, contract requirements, work location, internal equity, and business needs.

The posted range reflects the Sky's reasonable estimate at the time of posting and does not guarantee a specific salary or rate. Final compensation will be determined based on the selected candidate's qualifications and applicable contractual and business considerations.

Sky Solutions Benefits & Culture at a Glance

Healthcare & Wellness

Medical, dental, and vision coverage tailored to your needs.
Supplemental options like life insurance, disability, HSA/FSA available.
Time Off & Work-Life Balance

Starting at 15 PTO days per year, increasing with tenure.
Plus 11 paid holidays to recharge and spend time with loved ones.
Professional Growth & Development

Annual education stipend.
Access to thousands of online courses.
Formal mentorship programs for career advancement.
Inclusive Culture

"One Team" mentality focused on collaboration and belonging.
Recognized as a Great Place to Work® for six years straight.