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RegScale

Director of Legal

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Hiring Remotely in Boston, MA
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In-Office or Remote
Hiring Remotely in Boston, MA

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Top Skills: Artificial IntelligenceLegal Technology

RegScale is a continuous controls monitoring (CCM) platform purpose-built to deliver fast and efficient GRC outcomes. We help organizations break out of the slow and expensive realities that plague legacy GRC tools by bridging security, risk, and compliance through controls lifecycle management. By leveraging CCM, organizations experience massive process improvements like 90% faster certification times, and 60% less audit prep time. Today’s expansive security and compliance requirements can only be met with a modern, CCM based approach, and RegScale is the leader in that space.   

Position: 

We are seeking a practical, highly detailed, business-focused Director of Legal to serve as the primary legal owner of all our contracting. This role will be critical to enabling revenue and partnerships, mitigating risk, and building a scalable legal function from the ground up.

You will work closely with Sales, Partnerships, Product, Finance, Services, Security, and RegScale leadership to negotiate customer, partner, and vendor agreements, balancing speed and risk in a fast-paced startup environment.

This is a hands-on role ideal for someone who enjoys problem solving, negotiating, and helping a rapidly growing company scale effectively and responsibly.

Key Responsibilities: 

  • Draft, review, and negotiate a wide range of agreements, including:
    • Customer licenses and services agreements, including those incorporating FAR and agency-specific clauses to efficiently close deals
    • Vendor licenses and services agreements
    • NDAs, reseller, channel, and other partner agreements
    • Prime and subcontractor agreements, including purchasing vehicles and schedules
  • Develop and maintain contract templates, clause libraries, and negotiation playbooks
  • Maintain contract database and advise internal teams on key contract terms and requirements, including:
    • Renewal provisions
    • Data rights, IP ownership, and licensing restrictions
    • FAR/DFARS flow-downs
    • Audit, recordkeeping, and termination provisions
  • Identify and manage legal, regulatory, and operational risk across commercial and government contracts, ensuring contracting practices consistently align with RegScale policies, investor expectations, and applicable laws
  • Translate legal requirements into clear, practical guidance for non-legal stakeholders

Required Qualifications:

  • Juris Doctor (JD) from an accredited US law school
  • Active license to practice law in at least one US jurisdiction
  • 8+ years of experience in technology contracting, either in-house or at a law firm
  • Working knowledge of both commercial and public-sector contracting frameworks
  • Ability to operate independently with minimal legal infrastructure

Preferred:

  • Prior in-house experience at an early-stage or high-growth software company
  • Experience supporting both commercial and government sales motions and procurement cycles
  • Experience with reseller or channel models
  • Familiarity with cybersecurity or compliance market(s) a plus
  • Experience negotiating international contracts a plus

Key Competencies:

  • Strong commercial judgment with risk-aware decision-making
  • Excellent drafting, negotiation, and stakeholder communication skills
  • Extreme attention to detail
  • Ability to balance speed-to-revenue with risk-management requirements
  • Startup mindset: flexible, resourceful, and execution-focused while comfortable working in ambiguity

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Key Facts About Chicago Tech

  • Number of Tech Workers: 245,800; 5.2% of overall workforce (2024 CompTIA survey)
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  • Key Industries: Artificial intelligence, biotechnology, fintech, software, logistics technology
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