Proposal Manager

Shift5 is redefining the future of onboard operational technology (OT). As a fast-growing scale-up, we specialize in cutting-edge cybersecurity, predictive maintenance, and compliance for OT systems across defense, aerospace, and rail. We are a team of passionate, innovative professionals who thrive in a collaborative environment, driven by a shared mission to revolutionize how fleets operate. By unlocking and democratizing the vast potential of onboard OT data, we help our customers’ fleets run smarter, safer, and more efficiently. Ready to be part of the next frontier in transportation and critical infrastructure? Come join us.

Our Values:

• Mission First Mindset: We exist to protect the service members who defend our nation and secure the critical systems that keep our economy moving.
• Relentless Innovation: We are motivated by the challenge of solving the toughest problems facing transportation and defense industries. 
• Data Driven Decisions: We make decisions rooted in data. Giving our team and stakeholders a more informed perspective possible when lives and missions are on the line.

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 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.