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 .

About the Company

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.

About the Role

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.

What You'll Own

• 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.

The Team

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.

What You'll Be Selling

The agency's core services include:

• SEO

• Paid Media

• Web Development

SEO and Paid Media represent particularly important areas of the agency's offering.

Typical customers are small and mid-sized regional businesses across industries including healthcare, medical and dental, legal services, home services, retail, and e-commerce.

The focus is on consultative sales of ongoing digital marketing engagements that produce measurable business results for clients.

What We're Looking For

The most important requirement is straightforward:

You have already sold digital marketing agency services and successfully managed salespeople selling those services.

This is not a role for someone moving into agency sales from an adjacent SaaS, technology, media, or professional-services environment. We are looking for someone with a proven track record in the same sales environment.

Required Experience

• Proven experience selling digital marketing services within an agency environment .

• Demonstrated success personally closing new business and carrying a sales quota.

• Proven experience managing and developing salespeople selling digital marketing services .

• Strong track record of closing recurring-revenue agency engagements.

• Experience selling to small and mid-sized businesses.

• Experience building or materially improving a sales process rather than only operating within an established one.

• Strong understanding of consultative, relatively short-cycle agency sales.

• Experience managing both inbound and outbound sales opportunities.

Particularly Valuable

• Strong experience selling SEO and/or Paid Media services .

• Experience selling Web Development.

• Experience selling across multiple digital marketing disciplines.

• Experience scaling a small sales team.

• Experience developing sales playbooks, scripts, training, and qualification frameworks.

• Experience improving CRM usage, pipeline management, and forecasting.

• Experience contributing to pricing, packaging, or go-to-market strategy.

• Knowledge of the Toronto digital agency market.

What Success Looks Like

You will be expected to:

• Generate meaningful recurring new revenue personally .

• Raise the performance of the existing sales team.

• Establish a clear and repeatable sales methodology.

• Improve conversion throughout the sales funnel.

• Create stronger visibility and discipline around pipeline management and forecasting.

• Build a scalable foundation for future sales team growth.

Ultimately, success means creating a sales organization that can consistently and predictably generate new recurring agency revenue .

Interview Process

1. Initial interview with the hiring manager.

2. Interview with the CEO.

3. Preparation of a 90-day sales plan.

4. Final panel presentation with senior leadership and an investor.