At a Glance
- Tasks: Lead and design our sales strategy while managing a dynamic team.
- Company: Join One Core Media, a leading digital marketing agency in Toronto.
- Benefits: Competitive salary, performance-based bonuses, and equity opportunities.
- Other info: Collaborate closely with the COO and CEO for career growth.
- Why this job: Make a real impact by shaping our sales organization from the ground up.
- Qualifications: 3-5 years in digital marketing sales with direct management experience.
The predicted salary is between 90000 - 110000 $ per year.
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
Head of Sales in Toronto employer: One Core Media
At One Core Media, we pride ourselves on being an exceptional employer in the heart of Toronto's vibrant digital marketing scene. Our collaborative work culture fosters innovation and growth, providing employees with direct influence over their roles and the opportunity to shape the future of our sales organization. With competitive salaries, performance-based incentives, and a clear path to equity, we empower our team members to thrive both personally and professionally while making a tangible impact in the industry.
