Contracts and Compliance Specialist-Remote

Flexion • Madison, WI

2d • $120,000 - $130,000 • Remote

About The Position

We’re looking for a Contracts and Compliance Specialist with deep expertise in federal and commercial contracting and an unwavering commitment to regulatory excellence. Most of the work we do supports large-scale, enterprise-wide systems for commercial clients or government agencies—this role in particular ensures that every engagement we take on is delivered with integrity, full compliance, and minimal risk.

At Flexion, an agile software company that’s been delivering excellence for over 30 years, our company culture is built on autonomy, trust, and transparency. We empower teams to remain self-sufficient and self-directed by hiring people who can solve complex problems through collaboration—this means lending a hand and flexing your multi-skilled muscles (legal coordination, risk analysis, proposal support, etc.) as needed. Every member of a cross-functional team is a leader who takes responsibility for the entire team’s success, mirroring the company’s overall low-bureaucracy structure.

We believe that growth comes from working together—and that includes supporting each other through thoughtful, constructive feedback. Flexion team members are expected to help each other grow, challenge ideas respectfully, and integrate feedback as a normal part of the workday.

Requirements

• At least 4 years of experience in federal contract administration or compliance, ideally at an IT services or government contracting firm
• Strong working knowledge of FAR, DFARS, and associated agency supplements
• Experience managing GSA Multiple Award Schedule (MAS) contracts and/or GWAC vehicles
• Familiarity with DCAA audit processes and government-wide compliance expectations
• Experience drafting, reviewing, and negotiating subcontract agreements and teaming arrangements
• Proven ability to track contract milestones, deliverables, and funding across multiple simultaneous contracts
• Excellent written and verbal communication skills—you can explain complex regulatory requirements to non-specialists
• Strong organizational skills and a meticulous eye for detail
• A bachelor’s degree in business, law, public administration, or a related field—or commensurate experience

Nice To Haves

• Experience with contract lifecycle management (CLM) tools or similar systems is a plus
• NCMA CPCM, CFCM, or equivalent professional certification is a plus

Responsibilities

• Draft, review, and negotiate contracts, subcontracts, NDAs, teaming agreements, and modifications
• Support full contract lifecycle management (RFP through closeout), including amendments and renewals
• Maintain contract files, documentation, and audit-ready records
• Coordinate with legal, finance, and delivery teams on contract terms, risks, and obligations
• Ensure compliance with federal regulations (FAR, DFARS), agency policies, and contract requirements
• Monitor contract performance (CPARS) and ensure adherence to terms, conditions, and reporting requirements
• Track and support compliance with government-wide contract vehicles (e.g., GSA MAS, GWACs)
• Maintain awareness of regulatory updates and assess impact to the business
• Identify, analyze, and track organizational conflicts of interest (OCI) and mitigation strategies
• Conduct internal compliance reviews and support external audits (e.g., DCAA, agency audits)
• Investigate and resolve contract compliance issues, disputes, or findings
• Assist in developing and issuing Statements of Work (SOWs), task orders, and subcontract agreements
• Evaluate subcontractor compliance and ensure flow-down of federal requirements
• Support proposal efforts by reviewing contract terms, representations, and certifications
• Track key contract milestones, deliverables, funding ceilings, and periods of performance
• Prepare compliance reports, dashboards, and documentation for leadership and clients
• Maintain systems for contract lifecycle management and compliance tracking
• Coordinate and track annual compliance training (e.g., ethics, security, procurement integrity)
• Provide guidance to internal teams on contract requirements, compliance expectations, and best practices
• Serve as a liaison between internal teams, subcontractors, and government stakeholders
• Support communication during contract negotiations, execution, and issue resolution

Benefits

• employees enjoy comprehensive health, dental, and vision coverage, along with life and disability insurance, flexible spending accounts, and a 401(k) plan
• generous paid time off
• referral bonuses
• commitment to well-being and career success

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Number of Employees: 101-250 employees