About Shift5

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.

As a Proposal Manager, you will lead the development of compelling, compliant, and high-quality DOW proposals that drive Shift5’s growth in government markets. You’re the owner of the proposal lifecycle, from initial kickoff through compliance reviews and delivery, ensuring our responses resonate with evaluators and articulate why Shift5 is the partner of choice for defense customers.  You’ll collaborate closely with capture, product, engineering, finance, legal, and executive leadership to deliver winning proposals.

This role is ideal for someone who thrives in fast-paced environments, can flex between strategic storytelling and tactical compliance, and enjoys building scalable proposal processes in a growing company.

What You’ll Do

• Own and manage the full proposal lifecycle for DOW opportunities, including RFPs, RFIs, white papers, BOAs, OTAs, SBIR/STTR, and unsolicited proposals.

• Serve as the single-threaded owner for proposal execution, including schedules, outlines, compliance matrices, reviews, and final submissions.

• Lead proposal kickoffs, color reviews, and final production reviews to ensure high-quality, on-time deliverables.

• Collaborate closely with capture, business development, engineering, product, finance, legal, and executive leadership to develop winning storylines and technical narratives.

• Translate complex technical solutions into clear, persuasive proposal content that highlights Shift5’s value and differentiators.

• Partner with capture and BD to shape win themes, discriminators, and messaging strategies aligned with evaluator priorities.

• Ensure strict compliance with solicitation requirements, evaluation criteria, and formatting instructions.

• Coordinate inputs from subject matter experts, executives, and external partners throughout the proposal process.

• Develop, curate, and maintain reusable proposal content, templates, and best practices to support scalability and consistency.

• Support post-submission activities, including Q&A responses, clarifications, and proposal debriefs.

What Success Looks Like 

• Fully own proposal lifecycle from kickoff to submission.

• Manage multiple simultaneous bids.

• Improve submission quality and compliance consistency.

• Establish a 6–12 month proposal maturity roadmap.

What We’re Looking For

• Bachelor’s degree in business, communications, engineering, or related discipline.

• 5+ years of experience managing DOW or federal government proposals and RFP responses.

• Deep understanding of DOW acquisition processes and compliance requirements (FAR/DFARS).

• Proven success crafting technically accurate and persuasive proposal narratives.

• Exceptional project management skills and ability to lead cross-functional contributors under tight timelines.

• Experience with OTAs, CSOs, or other non-traditional DOW vehicles.

• Familiarity with cybersecurity, software/SaaS, or defense-tech offerings.

• APMP certification or similar professional proposal credentials.

• Strong written and verbal communication skills, including the ability to translate complex technical content for non-technical audiences.

• Experience with proposal management tools and collaborative review workflows.

• U.S. citizenship required and ability to obtain a security clearance.

Compensation & Benefits

• Base Salary: $130,000-$170,000

• 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.  

About Shift5

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.

Shift5 is looking for a highly motivated, self-driven, and experienced Account Executive, Air Force/Space Force interested in helping our Armed Forces defend national infrastructure, weapons platforms and operational threat (OT) systems from malicious attackers. In this role, your primary focus will be introducing Shift5’s product capabilities and value to potential clients within the U.S. Air Force/Space Force. You’ll match our capabilities and strengths to clients' needs, and help our partners and clients understand our product’s ability to identify, detect and prevent threats from the most advanced attackers in the world. As our Account Executive, Air Force/Space Force, you will report directly to our Vice President of Federal and work across our sales and product team to meet (or exceed) sales goals and client requirements.

We’re looking for someone with executive level contacts in the U.S. Air Force/Space Force weapons systems community (program offices for land and air) who can craft an engagement strategy and drive opportunities within the space. Someone who embraces uncertainty, thrives in the unknown and views incomplete information as an opportunity. You must be self motivated, impact driven, customer focused, technologically savvy, and innovative at building internal relationships and external partnerships to attack the market with passion.

What You’ll Do

• Serve as the primary sales lead for customers within the U.S. Air Force/Space Force

• Identify, develop and execute account strategy to close new business opportunities and expand sales with clients across the U.S. Air Force/Space Force

• Meet (or exceed) revenue quota targets 

• Target, build and maintain relationships with key decision makers in the assigned territory 

• Engage and collaborate effectively with other areas of the business (Field Engineering, Product Development, Marketing, Operations) to create visibility with target accounts and drive engagement of target prospects at both the individual contributor and executive level

• Work cooperatively with system integrators and other key partners to leverage their established account presence and relationships

• Capture, maintain, and disseminate accurate and relevant prospect information to Shift5 colleagues

What We're Looking For

• 5-7 years of technology sales experience, specifically selling software security and/or infrastructure security products to corporate enterprises 

• Demonstrated experience forecasting sales, managing sales expenses and successfully closing new business

• Built and expanded business opportunities as an individual contributor as a member of a team member

• Demonstrated experience with target account selling, solution selling, and/or consultative sales techniques

• Experience with U.S. Air Force weapons systems requirements, deployment, and procurement activities.

• Strong problem-solving skills, ability to analyze complex multivariate problems and use a systematic approach to gain swift resolution.

• Strong understanding of Cybersecurity technologies and competitive offerings in the marketplace.

• An effective communicator with the ability to explain complicated concepts to a variety of audiences and skill levels

• Outstanding presentation, written, verbal and closing skills

• Exceptional time management, organizational and decision-making skills

• Ability to work remotely and able and willing to travel on short notice, up to 50% of the time

• Possess the drive to succeed and to participate in the growth of an exciting, fast-paced company

Compensation & Benefits: 

• Base Salary: $175,000-$200,000

• 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.