Director, Business & Legal Affairs

Reports to: Chief of Staff & Strategy Location: Hybrid / Toronto or Montreal

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 of 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 qualified 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

Benefits

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.

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📌 Legal and Business Affairs Director (Toronto)
🏢 Ingressivecapital
📍 Toronto