Head of Sales — Digital Marketing 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.

• 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.

• 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.

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.

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.