Head of Sales

One Core Media is a Toronto-based digital marketing agency serving clients across North America in retail/eCommerce, B2B, home services, legal, and medical verticals. Since 1999, we've built an integrated offering spanning paid media, SEO, creative, programmatic, and marketing automation - and we're now investing in the growth of our sales organization.

We're hiring a Head of Sales - a role built to design and lead our commercial engine, not just execute against one. This hire will build the structure and lead the team that drives it.

This is a player-coach role for an experienced sales leader who has built a process before and wants to do it again, at a company where the results will be visible immediately.

This role requires a background in agency-side managed marketing services sales (not SaaS or programmatic media sales alone) and prior direct people management experience. Candidates without both will not be a fit for this particular role.

• Sell and support the sale of integrated digital marketing services (SEO, paid media, creative, marketing automation) to SMB and mid-market clients
• Design and implement a repeatable sales system: playbook, pipeline cadence, conversion tracking, and forecasting
• Hire, coach, and manage a team expected to grow
• Carry a personal new-business quota alongside management responsibilities
• Analyze conversion and pipeline data to identify structural gaps and drive process changes
• Own CRM hygiene and reporting discipline in Hub Spot

• 3-5+ years selling managed digital marketing services (agency-side strongly preferred) - SEO, paid media, creative, or marketing automation retainers sold to SMBs
• Direct people management experience - has hired, onboarded, coached, and managed sales reps
• Has personally built or significantly rebuilt a sales process, including CRM hygiene, pipeline cadence, and forecast reporting
• Track record of quota attainment, both personally and as a team leader
• Experience selling to marketing directors, CMOs, or founders/owners of SMB or mid-market companies
• Consultative selling experience with complex, multi-stakeholder deals and longer sales cycles
• Strong metrics literacy - conversion rate analysis, pipeline KPIs, funnel diagnostics
• Hub Spot proficiency or comparable CRM experience; familiarity with prospecting tools like Apollo, Clay, or Linked In Sales Navigator is a plus
• Comfortable presenting to senior stakeholders and driving process change with a team
• Comfortable building structure where none exists, to close necessary gaps

• A builder mentality - energized by creating process, not just running someone else's playbook
• Confidence to bring data and perspective to leadership conversations
• Ownership of team outcomes, not just personal numbers

• Competitive base salary plus performance-based OTE
• Real influence over how our sales organization is built
• Direct partnership with the COO and CEO, to create a long-term path to leading OCM's entire growth function
• A modern tech stack (Hub Spot, Apollo, Clay, Linked In Sales Navigator)
• A defined path to earning equity in the company as you grow with the role