Join Our Innovative Team at Mile Two!

Are you into solving tough problems and building cool tech? Do you thrive in a team where your ideas are heard and your creativity is encouraged? If you're nodding along, Mile Two might be the place for you.

We're all about creating advanced solutions that really make a difference for our government partners. Our team uses the latest technologies to make a tangible impact, creating seamless integrations between human expertise and machine capabilities to tackle complex challenges.

Our values guide everything we do: Supported Autonomy: We trust you to take initiative and make decisions, but we've always got your back. Humble Expertise: We respect everyone's knowledge and skills, creating an environment where we can all learn and get better together. Success is a Team Effort: We believe that we can only achieve great things when we work as a team. Tangible Results: We're motivated by the desire to create real, measurable impacts through our work.

When you join us, you'll work on meaningful projects that challenge you and help you grow. We offer a supportive and inclusive environment, competitive benefits, and plenty of opportunities to advance your career. If you're ready to level up your career and be part of something special, check out our current openings and apply today.

Our Approach to AI in Hiring

At Mile Two, applications are reviewed by real people—not filtered out by bots. Authenticity matters more than keyword tricks. 

We know you're probably using AI tools to help draft or polish your resumes, and that’s fine! We're using AI to write this blurb about AI!  But we expect you to make it your own. Resumes that feel copy-pasted I —repetitive, oddly phrased, “too perfect” matches to our job description— may hurt your chances. Adding personal touches and real examples of your work will make your application stronger.

We look forward to meeting the real you!

A Note About Our Application Process

Please answer our screener questions honestly and thoroughly (rather than writing “see resume”). These are reviewed by real people—not bots—and play an important role in our selection process. Thoughtful responses will strengthen your application.

The Role

The Proposal Manager is responsible for leading the end-to-end development, management, and delivery of compliant, compelling, and winning proposals across the DoD, Federal Civilian, and State markets. This individual will collaborate closely with Capture Managers, BD leads, and Subject Matter Experts (SMEs) to drive high-quality RFx responses aligned with company strategy and customer mission needs.

The ideal candidate brings deep experience managing complex proposal efforts, developing content for technical volumes (Cloud, Cyber, AI/ML, IT Services, Data, and Engineering), and implementing process excellence through Shipley-based best practices and modern AI-assisted tools.

Key Responsibilities

• Lead and manage all aspects of proposal development across multiple simultaneous RFx efforts (RFI, RFP, RFQ, Sources Sought, White Papers, etc.)
• Partner with Business Development and Capture to support opportunity qualification, bid/no-bid recommendations, and pre-RFP shaping.
• Develop, manage, and enforce proposal schedules, color review timelines, and compliance matrices to ensure timely, compliant submissions.
• Facilitate and lead proposal kick-off meetings, daily stand-ups, and Pink/Red/Gold reviews with internal and external stakeholders.
• Author, edit, and format proposal content, including technical, management, and past performance volumes.
• Collaborate with SMEs, subcontractors, and teaming partners to gather technical input and translate into clear, persuasive narratives.
• Create and maintain proposal templates, outlines, capability statements, staffing matrices, and standard proposal artifacts.
• Leverage AI tools (e.g., VisibleThread Docs, ChatGPT, TechnoMile) to automate and enhance compliance, writing, and review efficiency.
• Manage corporate proposal repositories, past performance library, resumes, and graphics library.
• Support post-submission activities including lessons learned, debriefs, and process improvement.
• Develop proposal graphics, charts, and illustrations that visually communicate key technical and management concepts.
• Provide capture support, including industry day participation, customer engagement materials, and question submissions to Government POCs.

• Bachelor’s degree in English, Communications, Business, or related field.
• 7+ years of experience in proposal management and writing for Federal/DoD contracts.
• Demonstrated success leading multi-volume proposal efforts resulting in awarded contracts valued at $20M+.
• Strong understanding of Shipley proposal processes and compliance frameworks (Shipley Certification preferred).
• Experience with tools such as VisibleThread Docs (VT Docs), TechnoMile, Pipedrive, SharePoint, Adobe Creative Suite, and MS Office.
• Proven ability to manage multiple concurrent deadlines in a fast-paced environment.
• Excellent written and verbal communication skills with a focus on clarity, compliance, and persuasion.
• Experience creating and managing proposal graphics and document layout in Adobe Illustrator, Photoshop, or InDesign.
• Familiarity with AI tools for content generation and proposal automation.

Preferred Experience

• Background in cloud computing, cybersecurity, data management, IT modernization, or AI/ML technologies.
• Experience supporting GSA Schedules, SBIR/STTR, OTA, and Phase III proposals.
• Prior work within small to mid-sized GovCon organizations (SDVOSB, 8(a), HUBZone, WOSB).
• Track record of sole-source or strategic win contributions (>$50M+).
• Experience mentoring or managing proposal writers.