Head of Legal

This is Roofr's first dedicated legal hire, a high-impact, high-visibility role reporting directly to the CEO. You'll own the full legal function, building it from the ground up as a strategic partner to the business. We're not looking for a specialist; we need a sharp generalist who's comfortable across commercial contracts, employment matters, corporate governance, and everything in between. 

You'll work closely with Sales, People, Finance, and Product, getting into the details when needed, and shaping strategy when it counts. If you thrive in ambiguity, like building things, and want your work to have real company-level impact, this is the role.

This is an IC position for the foreseeable future, so this person will be hands-on. 

What You'll Get to Do:

Commercial & Contracts

• Draft, review, and negotiate customer agreements, MSAs, order forms, SaaS subscription agreements, and vendor contracts
• Maintain and evolve standard contract templates, playbooks, and fallback positions to enable Sales to move fast without sacrificing protection
• Advise the business on contract risk, commercial terms, and deal structures, including enterprise and partner agreements
• Own the contract lifecycle management process and tooling

Employment & People

• Serve as the go-to legal partner for the People team on employee relations matters, performance issues, terminations, and investigations
• Advise on employment law compliance across US and Canadian jurisdictions, including multi-province and multi-state nuances
• Review and maintain offer letters, employment agreements, equity documentation, and HR policies
• Support the build-out of scalable people processes as the company grows
• Support and advise on corporate insurance programs, including:

• Cyber liability
• Directors & Officers (D&O)
• Errors & Omissions (E&O)
• General liability and related coverage
• Vendor Risk
• Claims/Litigation coordination

Corporate & Governance

• Support corporate records, cap table documentation, and equity matters in partnership with Finance
• Support due diligence, financing rounds, and M&A activity as needed
• Support  entity compliance across jurisdictions and manage external counsel relationships

Privacy, IP & Compliance

• Support Roofr's privacy program, including CCPA, PIPEDA, and other applicable data privacy obligations
• Protect and manage Roofr's extensive IP portfolio, including trademarks, patents, software licensing, and open-source compliance
• Monitor regulatory developments relevant to SaaS, construction tech, and financial services (payments, financing features)
• Partner with Security and Engineering on data handling practices and vendor risk assessments
• Advise on privacy, security, and compliance matters across Canada and the US, including PIPEDA, CCPA, GDPR, AI tools and acceptable use policies, customer data usage, data retention, and internal security practices.
• Partner cross-functionally with Security, Product, Engineering, and GTM teams on vendor risk management, security reviews, incident response coordination, and scalable compliance frameworks that support business growth.

Legal Operations

• Build and maintain the legal infrastructure: templates, workflows, tooling, and playbooks that enable the business to scale without a large legal team
• Manage and direct outside counsel efficiently and cost-effectively
• Educate and train internal stakeholders on legal risk and processes

What You'll Bring to the Role:

• J.D. from an accredited law school and active bar admission in the US or Canada
• 8–12+ years of legal experience, with a mix of law firm and in-house tech or SaaS company experience strongly preferred
• Genuine generalist, you've handled commercial contracts, employment matters, and corporate work, and you're not looking to specialize
• Strong commercial instincts: you understand business context, not just legal risk, and you know how to find solutions that let the business move forward
• Experience supporting a scaling startup or growth-stage company (Series A through C or beyond); you know how to right-size legal work for the stage
• Comfortable with ambiguity and building from scratch — there's no playbook waiting for you here
• Clear, direct communicator who translates complex legal concepts into plain language without losing the nuance
• Cross-border fluency in US and Canadian employment and commercial law

Bonus Points:

• Experience with vertical SaaS platform businesses, construction tech, or fintech-adjacent products (payments, lending, insurance)
• Familiarity with revenue-generating contract structures like usage-based and subscription SaaS