Director of Legal @ KEV Group

Counselwell Inc.; Toronto; On-site; CAD 150,000 - 175,000; Full time

Benefits offered by this job

Stock options

Flexible PTO

Professional development opportunities

Job summary

Counselwell Inc. seeks a leader to manage legal, compliance, and security governance. You will oversee commercial contracting and compliance processes while collaborating across teams and ensuring regulatory obligations are met.

The ideal candidate has over 7 years of experience in legal and compliance roles, ideally within B2B SaaS or fintech. The position offers competitive compensation of CAD 150,000–175,000, stock options, and a flexible hybrid work model.

Qualifications

• Proven experience in legal, compliance, and security governance.
• Experience in a high-growth environment without cutting corners.
• Ability to work cross-functionally across departments.

Responsibilities

• Lead commercial contracting, drafting, and negotiation.
• Oversee compliance function and security governance.
• Build and maintain a comprehensive compliance program.

Skills

7+ years of relevant experience

B2B SaaS or fintech experience

Team leadership

Sharp judgment

Familiarity with privacy regulations

Education

Law degree (LL.B. or J.D.)

Job description

What You'll Be Doing

Own commercial contracting end-to-end, drafting, reviewing, and negotiating customer agreements while keeping deals moving efficiently. Work hand-in-hand with Sales and GTM teams to balance speed and risk and help build and scale the contract workflows and CLM system to support growth.

Provide legal support on corporate governance matters including board and audit committee materials, financings, and strategic transactions. Selectively manage external counsel relationships and weigh in on employment matters with the People & Culture team.

Lead the compliance function, overseeing a team that ensures KEV meets obligations across all jurisdictions, including privacy regulations such as GDPR and FERPA and financial compliance requirements tied to our role as a registered ISO and payments processor.

Build and maintain a compliance program that is rigorous yet pragmatic, scaling with the business and giving our school customers confidence that their funds and data are in safe hands. Work cross‑functionally with Product, Finance, and People & Culture to embed compliance thinking into product development and operations.

Oversee KEV’s security governance, collaborating with the Technology team to keep policies, frameworks, and certifications (e.g., SOC 2) current, credible, and operational. Manage vendor risk assessments, support security audits and customer due diligence requests, and ensure KEV’s security posture keeps pace with growth.

Lead and develop a team spanning legal, compliance, and security governance—setting direction, removing blockers, and creating an environment where people do their best work.

Shape what a modern, high‑functioning legal, compliance, and security team looks like at KEV—building scalable processes, identifying automation opportunities, and leveraging legal tech to punch above your weight.

What You Bring

• 7+ years of relevant experience spanning legal, compliance, and/or security governance, with a solid foundation in commercial contracting and corporate matters, plus a law degree (LL.B. or J.D.).
• B2B SaaS or fintech experience is a big plus—demonstrated ability to work fast in a high‑growth environment without cutting corners.
• Experience leading or growing a team, building a high‑performing and enjoyable culture.
• Sharp judgment, a practical approach to risk, and the communication skills to be a trusted partner to stakeholders across Sales, Finance, Product, and the C‑suite.
• Comfortable in ambiguity, excited to build, and genuinely interested in using tools and tech to scale impact.
• Familiarity with privacy regulations (GDPR, FERPA), payment compliance frameworks, and security standards like SOC 2 is a strong asset. Technical expertise is not required, but you understand the language and how to get things done cross‑functionally.

What's In It For You

This is a rare opportunity to build something—a modern legal, compliance, and security function powered by smart systems, great people, and a company that values you. You’ll have real ownership, real impact, and a front‑row seat to KEV’s next phase of growth.

Competitive base salary of CAD 150,000–175,000, stock options, and a benefits package designed to support you and your family. Hybrid work model: three days in‑office, two flexible.

What We Offer

Competitive compensation – We believe in rewarding great work with fair, competitive pay.

Meaningful benefits – Because your well‑being matters, both at work and at home.

Retirement Savings Support – Company‑matched RRSP in Canada and 401(k) contributions in the U.S.

Professional development – Ongoing learning, stretch opportunities, and continuing education through KEV Academy and KEV University.

Hybrid model – 3 days in the office to collaborate and connect, with flexibility the rest of the week.

Flexible PTO – Close to 4 weeks of vacation plus company‑wide holiday closures.

Office perks – Fully stocked snack bar and occasional catered lunches.

Accessibility & EEO

KEV Group accommodates individual needs in accordance with the Accessibility of Ontarians with Disabilities Act, 2005 (AODA), within our recruitment process. If you require accommodation at any time during recruitment, please speak with your recruiter.

KEV Group is an equal‑opportunity employer. We do not discriminate against any employee or job applicant because of race, color, religion, national origin, sex, physical or mental disability, or age.

KEV may use AI‑enabled tools to support components of our recruitment process. All hiring decisions are made by our People and Culture team in partnership with Hiring Managers.