---
title: 'Director, CMS & HHS Business Development at Agile Six Applications'
canonical: 'https://feeny.ai/job/director-cms-hhs-business-development-agile-six-applications-maryland-jej75cq8ve97'
type: 'job'
last_seen: '2026-10-17'
---

# Director, CMS & HHS Business Development at Agile Six Applications

- **Company:** Agile Six Applications
- **Location:** Maryland, United States / Northern Virginia, United States / Washington, D.C., United States
- **Work type:** remote
- **Posted:** 2026-10-07
- **Last confirmed live:** 2026-10-17
- **Apply:** https://job-boards.greenhouse.io/agilesix/jobs/8014958003

## Job description

## About the role

Agile Six is looking for a senior market development leader to grow our work across the Centers for Medicare & Medicaid Services (CMS), the broader U.S. Department of Health and Human Services (HHS), and the federal health information technology landscape.

We have more than a decade of delivery experience at CMS and HHS, including work in payment modernization, quality programs, agile transformation, and grants modernization. This role will build from that foundation, deepening our presence across CMS first, while identifying strategic opportunities across HHS and health IT where our experience and delivery model give us a meaningful advantage.

This is a highly autonomous role with significant responsibility for shaping where Agile Six invests, which opportunities we pursue, and how we develop relationships and partnerships in the market. As a self-managed organization, “Director” reflects the scope, accountability, and external leadership of the role rather than traditional people-management authority. Success is more than generating pipeline or revenue. We want to pursue work that aligns with our capabilities, values, and ability to deliver meaningful outcomes for government partners.

## What you'll do

Develop and execute our CMS/HHS market strategy

- Build and maintain a clear understanding of CMS centers and offices, decision-makers, modernization priorities, acquisition patterns, contract vehicles, incumbents, and upcoming opportunities.
- Translate market intelligence into a prioritized strategy for where Agile Six should invest time, relationships, and pursuit resources.
- Extend that strategy into adjacent HHS and health IT opportunities where our CMS experience creates a credible foundation.

Build relationships and shape opportunities

- Develop trusted relationships with government leaders, industry partners, primes, and other stakeholders across CMS and HHS.
- Represent Agile Six at relevant industry events, conferences, and partner conversations.
- Identify opportunities early enough to help shape stronger solutions and acquisition approaches rather than simply responding to released solicitations.

Own and develop a qualified pipeline

- Build and maintain a disciplined pipeline based on strategic fit, realistic win probability, delivery alignment, and potential impact.
- Make thoughtful pursue/no-pursue recommendations and be willing to recommend walking away from work that is not right for Agile Six.
- Connect pipeline planning with organizational forecasting and broader Market Development priorities.

Connect market development with delivery

- Work closely with Agile Six delivery teams to understand our existing work, client needs, lessons learned, and potential areas for expansion.
- Bring delivery expertise into opportunity shaping and ensure proposed work reflects what Agile Six can credibly and successfully deliver.
- Help create relationships and opportunities that give future delivery teams a strong foundation for success.

Develop partnerships and solutions

- Identify and develop teaming, subcontracting, and joint-venture opportunities that expand Agile Six's reach or capabilities.
- Lead or support strategic partner and teaming negotiations while protecting the integrity of our delivery model.
- Partner with Communications, Proposals, Delivery, Finance, Contracts, and company leadership throughout opportunity development and proposal work.

Strengthen how we do market development

- Use AI-enabled tools to support research, market mapping, pipeline analysis, competitive intelligence, and opportunity development.
- Contribute to shared Market Development practices, tools, intelligence, and strategy rather than operating as an individual sales function.
- Help improve systems and practices that are still developing rather than waiting for perfect infrastructure.

What success looks like

In this role, you will:

- Give Agile Six a substantially clearer view of the CMS market: where opportunities exist, where we have credibility, who we need to know, and where we should invest.
- Build and deepen relationships across CMS centers and the broader HHS ecosystem that lead to qualified opportunities.
- Develop a healthy pipeline of opportunities that balance growth potential with strategic and delivery fit.
- Identify partnerships and teaming strategies that meaningfully expand Agile Six's ability to compete and deliver.
- Help turn Agile Six's existing CMS/HHS delivery credibility into a larger, sustainable portfolio.
- Strengthen the way Market Development and Delivery share intelligence and shape opportunities together.
- Improve and make effective use of Agile Six's AI-enabled market development practices.

## What we expect at this level

As a senior leader at Agile Six, you will be expected to:

- Operate with significant autonomy and make sound decisions in areas where the path is not already defined.
- Translate broad organizational goals into strategy, priorities, and measurable action.
- Work effectively across organizational boundaries and influence outcomes without relying on positional authority.
- Exercise judgment about where Agile Six should and should not invest.
- Build alignment among people with different expertise, incentives, and perspectives.
- Surface risks, gaps, and changing conditions early and recommend a path forward.
- Strengthen organizational capability through what you build, learn, document, and share.
- Represent Agile Six's values and interests thoughtfully in high-stakes external relationships.

## What you'll bring

Required

- Significant experience in business development, market development, partnerships, or a similar strategic role in federal technology, digital services, or consulting.
- Deep familiarity with the CMS ecosystem, including how its centers operate, how technology services are procured, and the vehicles, partners, and incumbents that shape the market.
- Working knowledge of the broader HHS landscape.
- An established network within CMS and/or among organizations that work extensively with CMS.
- Strong relationship-building and communication skills, with demonstrated ability to turn relationships and market knowledge into meaningful outcomes.
- Experience working cross-functionally with delivery, contracts, finance, proposal, and/or other business functions.
- Ability to evaluate opportunities strategically rather than simply maximize pipeline volume.
- Experience using AI-enabled tools in your work, with sound judgment about where human expertise and context remain essential.
- Comfort operating in a small, evolving organization where systems and processes may still be developing.

Helpful experience

- Previous federal service at CMS or another HHS operating division.
- Experience navigating CMS/HHS procurement and acquisition environments.
- Familiarity with joint ventures, SDVOSB/8(a) partnerships, set-aside strategy, and federal teaming.
- Experience with health IT domains such as quality measurement, payment modernization, interoperability, or grants.
- Understanding of the relationship between federal health programs and state-level implementation.

## How you'll work

Market Development at Agile Six is a team effort. You will own significant areas of strategy and pipeline, but you won't operate as an isolated salesperson. You'll work with company leadership, Market Development teammates, delivery teams, and organizational partners to bring the right expertise into opportunities at the right time.

Our strongest growth comes from work we understand and can deliver well. That means staying close to Delivery, sharing intelligence openly, and measuring success by the quality and impact of the work we win.

Employment & Compensation

Engagement: Full-time; open to W-2 employment or an initial contract-to-hire arrangement. Compensation: Compensation will depend on the final level and engagement structure. For W-2 employment, Agile Six's current base salaries for the levels under consideration range from $182,767–$250,460. Contract compensation would be established separately based on the engagement structure. Location: US Remote. Preference will be given to candidates in the MD/N.VA/DC area.

Sixer Benefits

Our benefits are designed to reinforce our core values of Wholeness, Self Management and Inclusion. 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”.

- Self-managed work/life balance and flexibility
- Competitive salary
- Employee Stock Ownership (ESOP) for all employees!
- 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.

## About Agile Six Applications

## Company Overview
- **One-liner**: Agile Six is a people-first, fully remote digital services company that partners with U.S. federal agencies to build modern, human-centered government technology.
- **Entity Type**: Private (Bootstrapped, no outside venture capital)
- **Headquarters**: San Diego, California, United States
- **Founded**: 2015
- **Founders**: Robert Rasmussen (Co-Founder/CFO) and Ernie Ramirez (Co-Founder/CEO)

## Core Business
- **Primary industry**: Civic Tech / Government Digital Services
- **Target customers**: U.S. federal government agencies (B2G)
- **Mission statement**: "We build better by putting people first." The company's "Just Cause" is to create government digital services that are as powerful and easy to use as the best commercial apps.

## Products & Services
Agile Six is a full-spectrum digital services firm, not a product company. Their offerings are service-based:

- **VA.gov Modernization**: Partnering with the Department of Veterans Affairs to overhaul veteran-facing digital services, making them more accessible and user-friendly.
- **Diffusion Marketplace**: A platform helping the VA share best practices and innovations across the organization to save lives and improve care.
- **CCSQ Agile Coaching and Digital Transformation**: Coaching services for agencies like the Centers for Medicare & Medicaid Services (CMS) to shift culture, procurement, and delivery toward Agile best practices.
- **Digital Transformation Consulting**: End-to-end services including human-centered design, product development, DevOps, and cloud-based CI/CD to help agencies modernize legacy systems.

## Market Standing
- **Valuation/Market Cap**: Not publicly available (privately held, bootstrapped)
- **Key Metric**: ~85 employees (as of mid-2025, +8.5% YoY growth)
- **Notable Clients/Partners**: Centers for Medicare & Medicaid Services (CMS), Department of Veterans Affairs (VA), Centers for Disease Control and Prevention (CDC), Office of Personnel Management (OPM). Founding member of the Digital Services Coalition.
- **Growth Signals**: Active job postings up 400% year-over-year; LinkedIn follower growth of +19.1% annually; expanding into new federal markets (DoD, HHS).

## Competitive Advantages
- **Purpose-Driven Mission**: Only works on projects that align with its "Just Cause" — improving government services for citizens, veterans, and public health. This creates high employee engagement and retention.
- **Bootstrapped & Independent**: No VC funding or outside investors means the company can prioritize mission over profit, and has never had to "sell out" for a quick exit.
- **Founding Member of the Digital Services Coalition**: A charter member of a group of elite firms that have transformed government digital services, giving them deep credibility and relationships within the federal ecosystem.
- **Service-Disabled Veteran-Owned Small Business (SDVOSB)**: This status provides preferential access to government contracts, particularly with the VA.
- **No Middle Management Structure**: Operates with self-managing teams, coaching, and local decision-making rather than traditional hierarchy — a rare and attractive structure.

## Strategic Focus
- **Expanding into New Federal Markets**: Currently hiring Directors for Social Services (HHS), DoD Military Family & Benefits, and adjacent markets, signaling a push beyond their core VA and CMS work.
- **Deepening VA & Federal Health Partnerships**: Continued focus on the VA.gov modernization and Diffusion Marketplace, with dedicated Director roles for VA and Federal Health.
- **Scaling the Coaching Model**: Helping agencies shift their internal culture and procurement toward Agile best practices, not just delivering code.
- **Maintaining a Fully Remote, Self-Managed Culture**: As they grow, they are investing in structures that preserve autonomy, trust, and wholeness — no middle management, no hierarchy.

## Why Work Here
- **Fully Remote**: 100% remote-first company with team members across at least 28 U.S. states. No plans to return to an office.
- **No Middle Management**: The company operates with self-managing teams, coaching, and local decision-making. No traditional hierarchy or jockeying for status.
- **Generous Benefits**: 90% of medical, dental, and vision premiums paid (80% for family); 401k with 100% match up to 4%; Employee Stock Ownership Plan (ESOP) for all employees; employer-paid life and disability insurance.
- **Time Off**: 30+ vacation days (18 accrued + 11 holidays + 2 floating), plus flexible wellness days.
- **Parental Leave**: Company-paid leave for all new parents (birth or adoption).
- **Professional Development**: Company-paid, self-managed continuing education budget.
- **Culture**: Strong emphasis on "wholeness" — the company explicitly discourages working late nights, weekends, or answering emails on vacation. No glorification of overwork.
- **Remote Policy**: Fully remote, with team members across at least 28 U.S. states.

## Sources
1. [agile6.com](https://agile6.com/)
2. [agile6.com/about](https://agile6.com/about/)
3. [agile6.com/careers](https://agile6.com/careers/)
4. [agile6.com/team](https://agile6.com/team/)
5. [linkedin.com/company/agilesix](https://www.linkedin.com/company/agilesix)