Director, DoD Military Family & Benefits

Location: US Remote. Preference will be given to candidates in San Antonio, TX or the Washington, DC/N. Virginia area.

Base salary: $180,000 to $230,000, plus commission and performance-based equity.

Agile Six is a federal digital services company built on a decade of delivery excellence inside the VA, including benefits systems modernization, digital services, and applied AI. Our track record is strong: fixed-price contracts, high CPARS scores, and a delivery culture built on autonomous teams and real accountability.

We are at an inflection point. As we graduate from SDVOSB set-aside eligibility, we have structured JV partnerships to preserve our competitive positioning. But the harder truth is this: we built our business as a self-sufficient prime and never developed the sub and teaming relationships with mid and large firms that this next phase demands. The DoD military family and benefits market is dominated by other-than-small firms, and winning there requires relationship-driven BD from someone who already knows how these buying communities operate and how teaming decisions actually get made.

The person we are looking for has ideally lived inside this space, whether from the government side, inside a prime's BD or capture function, or both. Someone who can walk into a conversation with a capture manager at a mid-tier prime and be taken seriously. We know that person is rare. If you have most of what this role requires and are genuinely energized by building something from near-zero in a market where the methodology gap is real and the mission matters, we want to talk.

The Role

This is Agile Six's first dedicated BD role focused on the DoD military family and benefits market. You will own the strategy and execution for breaking into DHA, DMDC, MC&FP, Army IMCOM, MEDCOM, and related warfighter support agencies, a mission space where our VA modernization heritage translates directly.

Agile Six helped build the digital front door for 9 million Veterans. Several of our people built the predecessor systems for military families before that. DHA is today at the starting line of a transformation that VA completed between 2017 and 2022. The firms currently holding DHA contracts have the vehicles and the relationships. They do not have the methodology. We do.

You will build the teaming pipeline from near-zero. You will have full leadership support, a competitive compensation structure, and a direct path to meaningful ownership in a firm on an ESOP trajectory. If you have read about how the VA digital transformation happened, nodded along, and thought "we need this at DHA," we want to talk.

We care about what you bring in, but we care as much about what you walk away from. Bringing us revenue we cannot deliver well, or that does not align with how we operate, is worse than bringing us nothing. The judgment about which opportunities fit is part of the job, not an afterthought.

What This Role Actually Is

This is not a standard Director position at Agile Six. We are asking you to build a new book of business in a market where we have limited or no presence. You will operate with more autonomy than a typical hire and more accountability than a typical role. You will have direct access to company ownership, a seat in the strategic conversation, and an equity stake tied to what you build. In return, we expect real traction within the first year. If it is not working, we will say so. If it is working, the upside is real.

How BD Works at Agile Six

This is not a quota-driven, individual commission role. We are building a market development team that develops markets together, shares intelligence, and wins work we can actually deliver well. You will own your pipeline, but you will operate as part of a team. Senior leadership is active in relationship development and closing. Your job includes building presence, cultivating relationships, developing pipeline, and bringing the right people into the right conversations at the right time. Some days you will close deals yourself. Some days you will set the table for someone else. The measure is what the team produces together, not just what any individual brings in.

Delivery-informed BD is core to how we operate across every market we serve. You are not working in parallel to delivery. You are working from it. Our active teams are the source of truth for where the real opportunities are, what is actually working, and what we should avoid. If you are used to selling ahead of delivery, this will feel different. If you are used to working alongside delivery to shape better outcomes, this will feel like leverage.

Responsibilities:

• Own the Pipeline: Own end-to-end BD pipeline for DHA, MC&FP, Army IMCOM, MEDCOM, and warfighter family support agencies. Build the relationships, manage the pipeline, and identify the right opportunities before they become solicitations.
• Teaming and Prime Relationships: Identify, cultivate, and close teaming arrangements with mid and large prime contractors pursuing software modernization work in the military health and family benefits space. Prioritize partners who need modern HCD and AI-enabled delivery capability.
• JV Activation: Activate Intuitial Six and Theta Six JV partnerships for 8(a) task order pursuit at DHA and DMDC. Work directly with JV partners to identify and close the first DoD task orders with Agile Six as named delivery sub.
• Delivery-Informed BD: Work directly with delivery leadership to ensure every teaming arrangement and pursuit is grounded in what we can actually execute. Our methodology is the differentiator. Protect it in how you structure deals.
• Subcontract Structure: Prioritize FFP subcontract arrangements that preserve team autonomy. This is our cultural non-negotiable and it is reflected directly in how we structure compensation.
• Industry Engagement: Represent Agile Six at DHITS, HIMSS Federal, and other DoD health and military family program conferences. Be visible where DHA, DMDC, and MC&FP program managers go to learn and connect.
• Market and Competitive Intelligence: Serve as Agile Six's primary intelligence source on DHA and IMCOM procurement landscape, upcoming opportunities, and competitor positioning. Bring intelligence that shapes strategy, not reports that sit in a folder.
• AI-Informed Market Positioning: Represent Agile Six's applied AI capabilities credibly in program office and partner conversations. Use AI tools actively in your own BD practice including market research, pipeline analysis, and competitive intelligence.
• Pipeline Management: Own and manage the DoD BD pipeline in Groundwork, our internal CRM, with the discipline and transparency we expect across the Market Development team.

What Success Looks Like in the First 12 Months:

In your first year, you will have established active, productive relationships with program office contacts at two or more of DHA J-6, DMDC, MC&FP, or Army IMCOM. Not introductions. Real conversations about real requirements. You will have helped close at least one 8(a) task order where Agile Six is the named delivery sub, giving us our first citable DoD past performance reference. You will have initiated at least one subcontracting conversation with a prime holder that has advanced to a teaming agreement or active pursuit. You will own a pipeline with sufficient coverage to sustain the DoD practice through its early phase, typically in the range of three to five times your near-term revenue target. You will have shaped our DoD market entry strategy in ways that reflect your own intelligence about this space, not just the plan you were handed. And you will have done all of this in a way that feels like Agile Six: direct, honest, values-forward, and genuinely interested in the mission.

We will know within the first six to nine months whether this is working. If it is not, we will have an honest conversation and we will act on what we see. That honesty works in both directions. If you are not getting what you need from us, we expect you to tell us.

Qualifications and Expectations: 

• 8+ years in business development, capture, or program management in DoD digital health, military family, or benefits. Not a generalist BD background.
• Active, current relationships inside DHA J-6, DMDC, MC&FP, Army IMCOM, or MEDCOM program offices. Not historical. Not aspirational.
• Direct experience inside a mid or large prime's BD or capture function, or as a government program manager with direct prime relationships. Someone who can walk into a capture conversation at a mid-tier prime and be taken seriously, because they already know the programs, the people, and the procurement landscape by name.
• Demonstrated history of successful teaming arrangement execution, not just pipeline building.
• Fluency in GovCon BD mechanics: PTW analysis, gate reviews, capture strategy, teaming agreements.
• Fluency with the programs we are targeting: milConnect, MHS GENESIS, MySECO, DHA CDAO initiatives, caregiver and survivor benefits. You should not need these explained to you.
• Entrepreneurial orientation. You are here to build, not maintain.

Strongly Preferred Qualifications: 

• Experience in benefits, case management, or health IT in a DoD or federal health context.
• Familiarity with USDS-style delivery, agile at scale, or digital services modernization.
• Prior work with SDVOSB, 8(a), or other socioeconomic JV structures.
• Experience on task order vehicles: CIO-SP4, OASIS+, DHA IDIQs, or similar.
• Track record recruiting and managing sub BD relationships at the small business level.
• Demonstrated ability to use AI tools in your own work: research, pipeline analysis, competitive intelligence.
• Comfort with ambiguity and appetite for building in a market where the infrastructure does not yet exist.

Compensation and Ownership: 

Base salary: $180,000 to $230,000, plus commission and performance-based equity.

This role is compensated differently than most positions at Agile Six, and for good reason. We are asking you to build something. The upside should reflect that.

You will have a direct equity conversation with company ownership as part of the offer process. Equity vests on performance, not tenure. Bring in meaningful, aligned revenue and you participate in the long-term value you helped create. Produce nothing and the equity does not vest. The structure is that direct.

If your background is exceptional, we are open to discussing compensation structure from the start. For strong performers, we also revisit as results come in. Few firms in this space will have either conversation. We will.

Sixer Benefits

Our benefits are designed to reinforce our core values of Wholeness, Self Management and Inclusion. The following benefits are available to all employees. We respect that only you know what balance means for your life and season. While we offer support from coaches, we expect you to own your wholeness, show up for work whole, and go home to your family the same. You will be seen, heard and valued. We expect you to offer the same for your colleagues, be kind (not controlling), be caring (not directive) and ready to participate in a state of flow. We mean it when we say “We build better by putting people first”.

All Sixers Enjoy:

• Self-managed work/life balance and flexibility
• Competitive and equitable salary 
• Employee Stock Ownership (ESOP) for all employees!
• Annual performance bonuses tied to team and individual objectives (details shared during the hiring process)
• 401(k) matching
• Medical, dental, and vision insurance
• Employer paid short and long term disability insurance
• Employer paid life insurance
• Self-managed and generous paid time off
• Paid federal holidays and two floating holidays
• Paid parental leave
• Self-managed professional development spending
• Self-managed wellness days

Hiring practices

Agile Six is an Equal Opportunity employer. All qualified applicants will receive consideration for employment without regard to any factor protected by applicable federal, state or local laws.

Note: We participate in E-Verify. Upon hire, we will provide the federal government with your Form I-9 information to confirm that you are authorized to work in the U.S. Unfortunately, we are unable to sponsor visas at this time.

If you need assistance or reasonable accommodation in applying for any of these positions, please reach out to careers@agile6.com. We want to ensure you have the ability to apply for any position at Agile Six.

Please read and respond to the application questions carefully. Interviews are conducted on a rolling basis until the position has been filled.