Air Force Strategic Planner Jobs (NOW HIRING)

Shift5 is building the data platform for onboard operational technology (OT). We deliver cybersecurity, predictive maintenance, and compliance capabilities that enable defense and commercial fleets to operate with greater readiness, resilience, and mission assurance.

We are seeking a mission-driven Air Force Strategic Account Executive to lead business development, capture strategy, and revenue growth across the U.S. Air Force. This individual will develop trusted relationships with senior Air Force stakeholders, identify and qualify strategic opportunities, and drive opportunities from early customer engagement through contract award.

This role sits at the intersection of customer engagement, mission understanding, product strategy, and business growth. The ideal candidate understands Air Force acquisition, operational priorities, and modernization efforts, and can effectively align Shift5's capabilities to mission needs.

This is not a transactional sales role. It requires strategic thinking, executive presence, and the ability to build long-term partnerships across government, industry, and internal teams.

Note: This position requires U.S. citizenship due to federal contract requirements and access to controlled information. An active security clearance is strongly preferred.

• Own and execute Shift5's Air Force growth strategy across assigned accounts, major commands (MAJCOMs), Program Executive Offices (PEOs), Program Offices (SPOs), and operational units.
• Build trusted relationships with senior Air Force leaders, acquisition officials, program managers, operational users, and industry partners.
• Identify, qualify, and mature strategic opportunities aligned with Shift5's growth objectives.
• Develop and execute account plans that align customer priorities with Shift5's product roadmap and strategic objectives.
• Lead opportunity strategy from early shaping through capture, proposal, negotiation, and award.
• Partner closely with Product, Engineering, Mission Delivery, Government Affairs, Marketing, and Capture teams to develop winning customer strategies.
• Develop customer engagement plans, executive briefings, capability demonstrations, and mission-focused presentations.
• Maintain an accurate opportunity pipeline and forecast while providing regular updates to Growth leadership.
• Support proposal development by contributing win themes, customer insights, competitive intelligence, pricing strategy, and technical differentiators.
• Monitor Air Force budgets, acquisition strategies, modernization initiatives, and emerging mission priorities.
• Represent Shift5 at industry events, customer engagements, conferences, and trade shows.
• Serve as the Voice of the Customer by providing continuous market feedback that influences product strategy and future capabilities.
• Develop strategic partnerships with prime contractors, system integrators, OEMs, and ecosystem partners supporting the Air Force.

• Develop trusted relationships across key Air Force organizations within the first 90 days.
• Build and execute a comprehensive Air Force account strategy with measurable pipeline growth.
• Consistently identify and mature qualified opportunities aligned with Shift5's strategic priorities.
• Increase pipeline conversion and win rates through disciplined account management and capture strategy.
• Become a trusted advisor to both customers and internal stakeholders.
• Drive sustainable revenue growth while expanding Shift5's footprint across Air Force programs.
• Influence product strategy through customer feedback and market intelligence.
• Establish strategic partnerships that create long-term growth opportunities.

• 7+ years of experience in defense sales, business development, account management, or capture management supporting the U.S. Air Force.
• Demonstrated success managing complex enterprise or federal sales opportunities with long sales cycles.
• Deep understanding of Air Force organizations, acquisition processes, budgeting, and modernization priorities.
• Experience selling software, cybersecurity, SaaS, data analytics, AI, or mission systems into the Department of Defense.
• Strong executive communication, presentation, and relationship-building skills.
• Experience leading opportunity shaping, capture strategy, and proposal support.
• Proven ability to work collaboratively across Product, Engineering, Marketing, Contracts, and executive leadership.
• Strong strategic thinking, negotiation, and problem-solving skills.
• Bachelor's degree or equivalent experience.

Preferred Qualifications

• Active Top Secret security clearance.
• Experience supporting Air Combat Command (ACC), Air Mobility Command (AMC), Air Force Materiel Command (AFMC), Air Force Sustainment Center (AFSC), or Space Force organizations.
• Existing relationships within Air Force acquisition and operational communities.
• Experience working within a defense technology startup or high-growth software company.
• Familiarity with Salesforce, GovWin, SAM.gov, and federal opportunity tracking tools.
• Military service or direct experience supporting Air Force operations is highly desirable.

• Base Salary: $175,000 - $190,000

• Bonus program and equity in a fast-growing startup

• Competitive medical, dental, and vision coverage for employees and their families

• Health Savings Account with annual employer contributions

• Employer-paid Life and Disability Insurance 

• Uncapped paid time off policy 

• Flexible work & remote work policy 

• Tax-deferred public transit benefits with Metro SmartBenefits (DC/MD/VA)  

We are committed to building an inclusive culture of belonging that embraces the diversity of our people and represents the communities in which we work and the customers we serve. We know the happiest and highest performing teams include people with diverse perspectives and ways of solving problems. We strive to attract and retain talent from all backgrounds and create workplaces where everyone feels empowered to bring their full, authentic selves to work.   

Shift5 is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sexual orientation, gender identify, national origin, disability, age, marital status, ancestry, projected veteran status, or any other protected group or class.