Head of Legal at Roofr

Worldwide

At Roofr, we’re obsessed with our customers. We constantly gather feedback to shape, prioritize, and launch the products they truly need. That’s what makes Roofr’s CRM special. We started by building essential sales tools like aerial roof measurements and digital sales proposals. But when our customers asked for a simple, affordable way to manage and scale their entire businesses, we listened. So, we created a CRM that connects these solutions—along with payments, material ordering, and more—into a seamless, powerful platform. With a clear roadmap ahead, we’re excited to continue expanding and leading the market with innovative products. We have an amazing culture, strong financials, and best-in-class company metrics. It’s an exciting time to be part of an extraordinary startup that is already successful, yet still early enough to offer its team significant growth, equity, and the opportunity to make a real impact. This position is for an existing vacancy. 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 Our compensation ranges are built using multiple market benchmarks and reflect both the scope of the role and current market data. While many hires fall within the beginning to midpoint of the band to allow for growth over time, we tailor offers based on each candidate’s experience, seniority, and demonstrated impact. 🏠 What we offer (US + Canada) When you join our team, you’re not just accepting a job. You’re making a career move. Here’s how we’ll support you in doing some of the most impactful work of your career: 🏝️ Vacation/Paid Time Off: 1st week of employment is mandatory PTO! Start your journey with Roofr by decompressing and recharging - we will see you in week 2! 1 Friday off per month (we call those our laundry days!) Company wide paid shutdown for the week between Christmas and New Years Flexible time off 80% employer-paid benefits in the U.S. and 100% employer-paid premiums for Extended Healthcare and Dental in Canada RRSP/401k match Generous Parental Leave policy 🤝 Perks: We host an annual company retreat with great team building activities Ample learning and development opportunities to continue growing your career Home office setup stipend Internet and phone allowance Remote first culture Weekly Friday paydays! 🤖 AI Notice At Roofr, we’re big fans of AI. It helps us write job descriptions that don’t put you to sleep, takes notes during interviews so we can actually listen, and even helps us track down awesome humans like you. Feel free to use AI to prep, research, or get pumped up for your interview (we see you, ChatGPT power users 👀). But when it’s time to chat, we’d love to meet you, not your AI alter ego. Bring your real, unfiltered self, we promise we will too. And don’t worry, a real, live human is behind every part of our process. Every application is reviewed by a real person, and you’ll always speak with real humans throughout the interview process. No bots, just good people ☺️ ⚠️ Important Notice We’ve been made aware of an individual impersonating Roofr using a fraudulent domain: roofrr.com (note the extra “r”). Our company takes the security and privacy of job applicants very seriously. We will never ask for payment, bank details, or personal financial information as part of the application process. All our legitimate job postings can be found on our official career site. Please be cautious of job offers that come from non-company email addresses, instant messaging platforms, or unsolicited calls. To ensure your application is legitimate, please apply directly through our official careers page: https://roofr.com/careers. If you receive any suspicious messages or have questions, reach out to us at talent@roofr.com. Your safety and security are important to us — thank you for your vigilance! Roofr is proud to be an equal opportunity employer. We are committed to equal employment opportunity in the workplace regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or veteran status.