About One Core Media

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.

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 current-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

Skills & Competencies
- 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

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 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

📌 Head of Sales (Toronto)
🏢 One Core Media
📍 Toronto