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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.
The Opportunity
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.
Important
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.
What You'll Do
- 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 HubSpot
What We’re Looking For
Experience & Background
- 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
- HubSpot proficiency or comparable CRM experience; familiarity with prospecting tools like Apollo, Clay, or LinkedIn 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
What Sets Successful Candidates Apart
- 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
What We Offer
- 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 (HubSpot, Apollo, Clay, LinkedIn Sales Navigator)
- A defined path to earning equity in the company as you grow with the role
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