About Clutch: 

We’re on a mission to reinvent the way people buy, sell, and own cars. Are you game? 

Clutch is Canada’s largest online used car retailer, delivering a seamless, hassle-free car-buying experience to drivers everywhere. Customers can browse thousands of cars from the comfort of their home, get the right one delivered to their door, and enjoy peace of mind with our 10-Day Money-Back Guarantee… and that’s just the beginning. 

Named five years in a row to the Globe & Mail’s list of the Top Growing Companies in Canada and also awarded spots on Deloitte’s Technology Fast 50™ and Fast 500™ lists, we’re looking to add curious, hard-working, and driven individuals to our growing team. 

Headquartered in Toronto, Clutch was founded in 2017 and currently services Ontario, New Brunswick, Nova Scotia, British Columbia, and Prince Edward Island. Clutch is backed by several world-class investors, including Altos Ventures, Canaan Partners, BMO Capital, iA Financial, and FJ Labs. To learn more, visit clutch.ca. 

About the role: 

We are on a mission to build a world-class company that is trusted by customers, employees, partners, regulators, and investors. As we scale rapidly, we are looking for a strategic, business-minded VP & General Counsel to lead Clutch’s legal function and serve as a trusted advisor to the CEO and executive team. 

Reporting directly to the CEO, this high-impact role will own the company’s legal strategy and day-to-day legal execution across commercial contracts, employment and HR matters, privacy and data security, consumer protection, regulatory compliance, corporate governance, risk & insurance program oversight, and automotive retail compliance, including OMVIC and applicable provincial requirements. You will operate at the intersection of legal, business, product, operations, finance, and risk — helping Clutch move quickly while building durable, scalable processes that protect the company and support growth. 

This is a unique opportunity for a builder: someone who brings strong legal judgment, pragmatic business instincts, and the ability to create a modern legal function for a category-defining Canadian company. The right person will help us Deliver Wow by making complex legal and regulatory work feel simple for the business, Take Extreme Ownership of outcomes, Check the Glovebox by building strong legal fundamentals, and Win Together with teams across Clutch. These values are part of Clutch’s cultural framework, alongside Experiment Relentlessly and Refuse to Settle. 

Importantly, this is a hands-on, build-from-zero role. For the foreseeable future you are the legal function — drafting the agreements, writing the playbooks, and making the judgment calls yourself — before you build a team around you. 

What you'll do: 

• Legal Strategy & Executive Counsel: Serve as the company’s senior legal advisor, partnering closely with the CEO and executive team on strategic initiatives, risk management, regulatory matters, governance, and high-impact business decisions. 
• Commercial Contracts & Negotiation: Lead review, drafting, and negotiation of key commercial agreements, including vendor contracts, SaaS and technology agreements, marketplace and automotive partnerships, financing-related agreements, real estate and operations agreements, and other strategic business contracts. 
• Consumer Law & Advertising Compliance: Own legal oversight of consumer-facing policies, disclosures, advertising claims, purchase and sale processes, warranty and protection products, refund policies, and customer communications to ensure compliance with applicable consumer protection laws and regulations. 
• Automotive & Dealer Regulation : Lead Clutch’s compliance approach for OMVIC and applicable provincial motor vehicle dealer requirements, including licensing, advertising, disclosures, sales practices, complaints, audits, and internal training. 
• Privacy, Data Security & AI Governance: Build and maintain a scalable privacy and data governance framework, including policies, consent flows, incident response, vendor risk review, data retention, privacy impact assessments, and practical guidance on product, analytics, AI, and customer data use. 
• Employment & HR Legal: Oversee employment matters in partnership with People Operations and external counsel — exercising sound judgment on sensitive issues such as terminations, investigations, and policies, and managing specialists where deeper expertise is needed. 
• Risk Management & Process Development: Build practical legal processes, templates, playbooks, approval workflows, and training programs that help teams move faster while managing risk consistently. You’ll help Clutch “check the glovebox” by mastering the basics, avoiding skipped steps, and creating repeatable processes that earn trust. 
• Corporate Governance & Board Support: Support corporate governance, board materials, investor matters, financings, entity management, policies, and other corporate legal requirements as Clutch continues to scale. 
• Cross-Functional Collaboration: Work closely with Product, Engineering, Operations, Finance, People, Marketing, Sales, Customer Experience, and Marketplace teams to embed legal thinking into business execution without creating unnecessary friction. 
• External Counsel Management: Manage external counsel efficiently across specialized matters, ensuring high-quality advice, clear accountability, and disciplined legal spend. 
• Team Leadership: Build, mentor, and develop a high-performing legal function over time, fostering a culture of strong judgment, ownership, speed, high standards, and practical problem-solving.

What we're looking for:

Must have

• Education: JD, LLB, or equivalent law degree; licensed and in good standing with the Law Society of Ontario or another Canadian law society.
• Experience: 15+ years of legal experience, ideally including a mix of top-tier law firm training and in-house leadership at a high-growth technology, marketplace, fintech, automotive, consumer, retail, or regulated business.
• Deep experience reviewing, drafting, and negotiating a broad range of commercial contracts with strong business judgment and a bias for practical, scalable solutions.
• Entrepreneurial mindset with a bias for action — comfortable operating in ambiguity, building from scratch, and improving how legal work gets done.
• This is an in-office role based out of our downtown Toronto headquarters or our Mississauga flagship facility.

Strong assets

• Experience overseeing or partnering closely on corporate insurance programs, including broker management, policy adequacy, renewals, claims, and coverage across D&O, cyber, E&O, property, garage liability, and other business-critical insurance lines.
• Familiarity with Canadian employment law and experience partnering with HR and business leaders on sensitive employee matters is an asset.
• Experience advising on privacy, data security, data governance, and technology-related legal issues, including practical application of Canadian privacy laws.
• Strong understanding of consumer protection, advertising, e-commerce, and customer-facing compliance obligations.
• Experience with automotive retail, OMVIC, vehicle sales, consumer financing, insurance/warranty products, or regulated consumer marketplaces is a significant asset.

Why you'll love it at Clutch:

• Autonomy & ownership – opportunity to build the legal function, influence company strategy, and create scalable processes across the business.
• Help shape the future of car buying and selling in Canada by leading a critical function for a fast-growing, consumer-facing technology company.
• Direct partnership with the CEO and executive team on complex, high-impact business, legal, and regulatory decisions.
• Work on meaningful and challenging projects across contracts, product, employment, privacy, consumer compliance, automotive regulation, and corporate governance.
• Collaborate with a talented and passionate team in a dynamic, fast-paced environment that values ownership, experimentation, high standards, trust, and winning together.
• We are dedicated to attracting and retaining top talent with top-of-market compensation packages.
• Above-market health & dental benefits.

Compensation & Benefits: 

• Benefits: Comprehensive benefits plans include healthcare, dental care, vision care, prescriptions, life insurance and dependent coverage; start from day 1. Applicable for Permanent Full-Time.
• Pay decisions reflect objective criteria: skills, performance, market benchmarking, responsibilities and working conditions.
• This posting is for an existing, open vacancy.

Clutch is committed to fostering an inclusive workplace where all individuals have an opportunity to succeed. If you require accommodation at any stage of the interview process, please email talent@clutch.ca.  We use AI-assisted tools to help screen and assess applications. Final hiring decisions are made by our team.