Principal Contracts Strategist

Onebrief is collaboration and AI-powered workflow software designed specifically for military staffs. By transforming this work, Onebrief makes the staff as a whole superhuman - meaning faster, smarter, and more efficient.

We take ownership, seek excellence, and play to win with the seriousness and camaraderie of an Olympic team. Onebrief operates as an all-remote company, though many of our employees work alongside our customers at military commands around the world.

Founded in 2019 by a group of experienced planners, today, Onebrief’s team spans veterans from all forces and global organizations, and technologists from leading-edge software companies. We’ve raised $320m+ from top-tier investors, including Battery Ventures, General Catalyst, Sapphire Ventures, Insight Partners, and Human Capital, and today, Onebrief is valued at $2.15B. With this continued growth, Onebrief is able to make an impact where it matters most.

We’re hiring a Principal Contracts Strategist to join our Contracting Team. This is a foundational, senior individual contributor role focused on owning complex, high-impact contract strategy and execution while shaping scalable systems that enable our sales and growth goals.

You'll report to our Head of Contracts and work closely with teammates across contract administration, partnerships, legal, finance, sales, and customer relations. This role blends deep hands-on execution with strategic ownership, serving as a point of leverage for the organization’s most critical contracting decisions.

We're looking for someone who understands that organizational scaling is a mind-set, not a final destination, and gets excited about the opportunity to tackle issues for the short and long term.

You have led complex and critical contract negotiation internal and external to the federal government, executing multiple layers of tasks yourself while effectively collaborating and managing work with other stakeholders to ensure alignment, resolve blockers, and drive high-quality outcomes. You know the demands and context of Federal acquisitions, as well as commercial products and contracting.

You understand the sales cycle of our clients and the lifecycle of contracts, and have a customer-centric mindset relating to our team’s function within the rest of the organization. You have enough technical and contracting fluency to speak confidently with different organizational layers, as well as the presence to lead clients through the ambiguity, solutioning, deadlines, and constraints of contracting.

You have the ability to build new systems and processes and inspire for iterative refinement and fine-tuning of those systems and processes. You’re extremely detail-oriented and able to break larger tasks and problems into smaller, quickly actionable items for rapid results. You work effectively across functions, adapt to evolving constraints, and build trust through consistent, reliable contract administration.

This role does not have direct people management responsibilities, but carries significant ownership, visibility, and influence across the organization.

• Work directly with the Head of Contracts to support the vision and execution for transparent and seamless contract award.

• Align contracts with business goals, involving analysis, negotiation, risk mitigation, and lifecycle management.

• Create a roadmap to contract strategy and turn it into clear, sequenced priorities.

• Ensure pre-award contracting workflows are reliable, scalable, and thoughtfully created and maintained. Solving for best-in-class while constantly improving to streamline with automation and efficiency.

• Work with contract administration team, partnerships, legal, finance, sales, and customer relations to stay aligned on priorities and outcomes. Proactively engage to identify dependencies and mitigate risks.

• Define and maintain contracting frameworks, playbooks, and decision models that scale across the organization.

• You are able to obtain a US Government Security Clearance (US Citizenship required)

• Bachelor's Degree in a relevant field plus a minimum of 10 years of related work experience as a contract professional supporting contract strategy and administration

• Deep expertise in federal government contracting (acquisition processes and regulations) and experience supporting software or technology-enabled products, including contracting models that support rapid delivery, enterprise adoption, and long-term mission outcomes.

  • Bonus: Previously a contracting officer within the federal government, preferred to have 8+years experience

• Business acumen with ability to think critically and develop creative and practical solutions

• Excellent written, verbal, and time-management skills, especially in distributed or async-first environments

• Strong analytical, problem solving, decision making, negotiation, communication and interpersonal skills

• Proven ability to translate strategy into roadmap into delivery with attention to detail and organization

• Experience designing and executing flexible acquisition approaches (e.g., OTAs, hybrid vehicles, novel contract structures) to accelerate outcomes while managing risk.

• Experience scaling contracting functions in a high-growth environment

  • Bonus: Someone who has scaled contract strategy and execution internationally

• Ability to lead through influence, align cross-functional partners, and operate effectively without direct authority

• High integrity, adaptability, and comfort operating independently in fast-paced environments

• Willingness to travel as needed

• You are willing and able to work out of the United States

Notice to Third Party Recruitment Agencies
Please note that Onebrief does not accept unsolicited resumes from recruiters or employment agencies. In the absence of an executed Recruitment Services Agreement, there will be no obligation to any referral compensation or recruiter fee. In the event a recruiter or agency submits a resume or candidate without an agreement Onebrief explicitly reserves the right to pursue and hire those candidate(s) without any financial obligation to the recruiter or agency. Any unsolicited resumes, including those submitted to hiring managers, shall be deemed the property of Onebrief.