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 up-to-date 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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📌 Head of Sales (Winnipeg)
🏢 One Core Media
📍 Winnipeg