Head of Sales — Digital Marketing Services
About The Position
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.
Requirements
- 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.
Nice To Haves
- 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.
Responsibilities
- 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.
Benefits
- Corporate medical and dental benefits.
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What This Job Offers
Job Type
Full-time
Career Level
Senior
Education Level
No Education Listed
