Vice President of Sales

Vice President of Sales

Chameleon Digital Media – Toronto, ON (Hybrid)

Are you a visionary sales leader ready to shape the next phase of growth at a company

that’s redefining how digital media connects with the real world? At Chameleon Digital

Media, we’re looking for a Vice President of Sales to lead, inspire, and scale a high-

performing team, while enjoying the flexibility and autonomy that come with a senior

leadership role.

Chameleon is an independent, data-forward digital media company turning real-world

behavior into actionable insights and addressable audiences. As we continue to grow,

we need a VP who brings strong strategic thinking, deep industry relationships, and the

leadership skills to unlock new opportunities and elevate our market position.

This is a unique opportunity to take ownership of our sales vision, lead and mentor a

growing team, and work closely with the C-suite to shape company strategy. We value

results, but we also believe in balance. This role offers a flexible hybrid schedule, built-

in autonomy, and a culture that prioritizes well-being and trust.

What You'll Be Doing:

 Lead and scale a team of digital media sales professionals, coaching and

supporting them to reach revenue goals

 Shape and execute a sales strategy focused on both agency and direct client

growth across Canada

 Strengthen Chameleon’s presence in the market by positioning our audience-

first, data-driven capabilities in a way that resonates with senior decision-makers

 Collaborate cross-functionally with product, marketing, and operations teams

to align solutions with client needs

 Represent the company at key industry events and conferences, acting as a

senior spokesperson and thought leader

 Forecast, track, and optimize pipeline performance using our CRM and

reporting tools

 Foster a positive, collaborative, and high-accountability team culture that

aligns with our values and ambition

What We Are Looking For:

 8+ years of experience in digital media sales or strategy, with at least 3+ years in

a senior leadership role

 Proven ability to hire, lead, and develop high-performing teams

 Strong agency and client relationships at the VP/CMO/Director level

 Deep understanding of digital channels (Programmatic Display, Video, DOOH)

and how data powers performance

 Strategic thinker with a passion for innovation, who can translate insights into

action

 Exceptional communication and storytelling skills, able to inspire clients and

teams alike

 Based in Toronto or willing to travel regularly to our office and key client markets

Why Join Us:

 Leadership Autonomy – We trust our leaders to lead. You’ll have a voice in

shaping our future and the freedom to do meaningful work, your way.

 Hybrid Flexibility – Work where you’re most productive, with core collaboration

days at our Toronto office.

 Work-Life Balance – We believe performance and well-being go hand in hand.

Expect clear goals, smart priorities, and a culture that respects boundaries.

 Growth & Recognition – Join a team that celebrates wins and supports

continuous development at every level.

 Competitive Compensation – Base salary, performance bonuses, and long-

term growth potential.

Job Type: Full-time

Benefits:

• Extended health care
• Work from home

Schedule:

• Monday to Friday

Experience:

• digital media sales or strategy: 8 years (preferred)
• senior leadership role: 3 years (preferred)

Work Location: Hybrid remote in Toronto, ON M6K 1X9