Legal Director

Job Title: Director, Business & Legal Affairs
Department: Business & Legal Affairs
Location: Hybrid / Toronto or Montreal
Reports to: Chief of Staff & Strategy

About Kensington Grey 

Kensington Grey is a leading influencer management firm specializing in representing diverse talent across various platforms and amplifying underrepresented voices. We work with top-tier talent to develop their brand, negotiate partnerships, and maximize their impact in the digital space. Our mission is to foster diversity, equity, and inclusion within the influencer landscape, amplifying underrepresented voices and driving meaningful change in the media and entertainment industry.

Position Overview

The Director, Business & Legal Affairs is a strategic and operational leader responsible for overseeing the organization’s legal function while acting as a key business partner across departments. This role combines legal expertise with commercial acumen to support contract negotiations, mitigate risk, and drive efficient, scalable processes. The Director will play a critical role in shaping deal structures, improving legal workflows, and ensuring timely execution of agreements in alignment with business objectives.

Key Responsibilities

• Support a team of Contract Specialists in the execution a high volume of commercial agreements, including talent, brand partnership, and vendor contracts
• Responsible for improving our MSA list with major partners for expedited contract processing 
• Provide practical, business-oriented legal advice to internal stakeholders
• Partner with teams to structure deals that balance risk while supporting revenue growth and strategic priorities

• Evaluate and improve the contract redline review process to increase speed, consistency, and accuracy
• Implement scalable systems and best practices to streamline contract workflows and approvals
• Drive continuous improvement across the full contract lifecycle
• Assess legal and business workflows to identify inefficiencies and implement solutions

• Collaborate with cross-functional teams to ensure seamless contract execution and communication
• Support the integration of tools or technologies to enhance legal operations

• Lead, mentor, and develop Contract Specialists, fostering a high-performing and solutions-oriented team
• Provide clear direction on priorities, workload management, and professional growth
• Oversee daily legal operations to ensure timely and high-quality output

• Develop and maintain standardized templates, playbooks, and process documentation
• Educate internal teams on contract standards, negotiation guidelines, and legal best practices
• Promote consistency and efficiency in how agreements are managed across the organization

• Collaborate closely with Finance, Talent Management, Brand Partnerships, Campaign Management, and PR teams
• Align legal processes with broader company goals and revenue-driving initiatives

• Monitor and report on key metrics such as contract turnaround time, deal cycle efficiency, and bottlenecks
• Use data to inform process improvements and support strategic decision-making
• Provide insights and reporting to senior leadership

• Ensure all agreements and processes comply with applicable laws, regulations, and internal policies
• Identify potential legal and business risks and recommend mitigation strategies
  Maintain strong governance and oversight of contractual obligations

• Review and provide oversight on all fully executed agreements (FEAs)
• Ensure accuracy, completeness, and proper documentation of all finalized contracts

Qualifications

• 8+ years of experience in business affairs, legal counsel, or a similar role (in-house or law firm)
• Strong experience negotiating commercial contracts, ideally within media, entertainment, or influencer marketing
• Demonstrated ability to balance legal risk with business objectives
• Experience leading and developing teams, with a history of 2+ direct reports
• Proven track record of improving legal processes and workflows (experience developing within a start-up organization is an asset). 
• Strong stakeholder management and cross-functional collaboration skills
• Excellent communication, negotiation, and problem-solving abilities
• High attention to detail and sound judgment in fast-paced environments
• Demonstrated competency in risk assessment and mitigation, while exercising business-minded legal judgement

At Kensington Grey, we believe in fostering a dynamic and rewarding work environment where talent thrives.

As a valued member of our team, you’ll enjoy:

✅ Competitive Compensation – We recognize your expertise with a salary and bonus structure that reflects your impact.

✅ Exciting Brand Collaborations – Work with top-tier talent, global brands, and high-profile campaigns that shape the entertainment and digital landscape.

✅ Innovative & Collaborative Culture – Join a passionate team that values creativity, fresh ideas, and a hands-on approach to success.

✅ Comprehensive Benefits Package – Enjoy health insurance, retirement plans, and additional perks that make a difference.

✅ Networking & Industry Access – Gain exclusive access to industry events, brand partnerships, and top-tier connections that fuel your professional growth.

Be part of a company that values your contributions and empowers you to make an impact.

Ready to grow with us?

Only applicants selected for interview will be contacted.

Thank you!