Head of Sales — Digital Marketing Services

Location: Toronto / North York, Canada
Work format: Hybrid — 3 days in the office, 2 days remote.
Non-negotiable.
Employment: Full-time
Compensation:
Up to CAD 200K OTE — approximately 50% base / 50% performance-based compensation Why This Role

• Up to CAD 200K OTE with significant upside tied directly to performance.

• Direct ownership of the sales function with a mandate to improve, structure, and scale it.

• A true player-coach position
  : lead the team while continuing to close meaningful business yourself.

• Direct access to the CEO and real influence over sales strategy, process, positioning, pricing, and growth.

• An existing sales team to lead, with the opportunity to expand the function as performance grows
  .

• Sell a broad portfolio of established digital marketing services, including SEO, Paid Media, and Web Development
  .

• Work with an integrated agency team across SEO, Paid Media, Creative, Brand Strategy, CRO, Data Analytics, and Web Development.

• Corporate medical and dental benefits
  .

• Hybrid schedule with a comfortable office in North York
  .

Our client is a fully integrated performance marketing agency combining SEO, Paid Media, Creative, Brand Strategy, Web Development, CRO, and Data Analytics under one roof.

The agency works primarily with growing small and mid-sized regional businesses across Canada, supporting clients throughout the full digital growth cycle — from strategy and customer acquisition to website development, conversion optimization, and long-term account growth.

The company is growing and is now looking for a hands-on Head of Sales to build a more structured, predictable, and scalable sales function and lead the next stage of commercial growth.

This is a senior player-coach sales leadership role combining personal revenue generation with ownership of team performance.

You will personally lead and close new business while managing and developing the existing sales team. The goal is not simply to operate an established sales process — you will have the authority and responsibility to make it better.

You will define sales standards, improve the full sales cycle, coach the team, strengthen pipeline discipline and forecasting, and create a repeatable methodology for generating recurring agency revenue.

You will report directly to the CEO.

• Own and deliver against personal new-business revenue targets.

• Personally lead opportunities from initial conversation and discovery through proposal, negotiation, and signed agreement.

• Manage, coach, and develop the existing sales team.

• Ensure the team consistently progresses toward individual and collective revenue targets.

• Build and continuously improve the end-to-end sales process.

• Establish clear standards for intro calls, discovery, qualification, proposals, follow-ups, negotiation, and closing.

• Coach team members on sales execution, pipeline management, deal strategy, and closing.

• Manage both inbound and outbound opportunities.

• Review pipeline quality, conversion rates, sales activity, and forecasting.

• Introduce greater structure, accountability, and measurable performance expectations.

• Partner closely with the CEO and internal SEO, Paid Media, Strategy, Creative, and Web Development teams.

• Provide commercial input into positioning, packaging, pricing, and client acquisition strategy.

• Help scale the sales organization as revenue and lead volume grow.

You will initially lead a small sales team consisting of:

• 1 BDR focused on appointment generation.

• 1 Sales Representative / Account Executive responsible for progressing opportunities from introduction through close.

The team is expected to expand once the sales function is consistently meeting its targets.

The agency's core services include:

• SEO

• Pai…