Head of Sales
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.
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
Vacancy posted 1 day ago
Similar jobs that could be interesting for youBased on the Head of Sales in Toronto, ON vacancy
- ...Head of Sales | Toronto Monex is a leading global financial solutions provider, offering a complete set of tools to support business growth and strategic financial operations. We specialize in FX risk management and international payments, helping corporate and institutional...SuggestedLocal areaWorldwideRelocation
- ...One of Canada's most recognized and trusted immigration brands is seeking a strategic, hands-on Head of Sales to unify their sales lawyer teams under a single leader and drive predictable revenue growth. With over 3 million monthly visitors across their digital media properties...SuggestedFull timeInternshipWork at officeVisa sponsorship
$178.2k - $236k per year
...The role / impact As Head of Sales, Canada, you will drive the overall performance and success of Xero across the region, with a primary focus on our accounting and bookkeeping partner channel. Reporting to the Country Manager, you will hold end-to-end accountability for...SuggestedPermanent employmentFull timeWork at officeLocal areaWork from homeFlexible hours$159.3k - $199.2k per year
...About the Team The Canada Ads Sales Team is responsible for the marketing vision, development, and growth of our advertising partnerships across CPG, New Verticals, and Restaurants. This team is rapidly growing, and is seeking additional team members to build an industry...SuggestedLong term contractFull timeTemporary workLocal area- ...Head of National Accounts & Institutional Sales Vanguard, a global leader in investment management, is seeking an accomplished and transformative Head of National Accounts & Institutional Sales for Vanguard Canada to develop and lead all B2B distribution strategies and...SuggestedLong term contract
- ...Monex Canada is seeking a Head of Sales to lead and expand its commercial FX and payments sales function nationwide from Toronto. This player-coach role will build and manage a high-performing team, own revenue delivery, and engage directly with strategic client relationships...
$200k - $300k per year
...authentic selves, you can do your best work and inspire others to do the same. About the role: We’re looking for a Founding Head of Enterprise Sales to own sales execution across strategic accounts, with a particular focus on Fortune 1000 brands, large enterprise design...Long term contractFull timeContract workFor contractorsInternshipImmediate startRemote workHome office- A leading wealth management platform is seeking a Head of Sales to drive pipeline growth and convert leads into agreements. This executive role requires 5+ years of sales experience in fintech or wealth management, with a proven track record in closing significant deals. Candidates...
- ...Head of Sales (Wealth Platforms – Canada & U.S.) We’re looking for a Head of Sales who knows how to close. Someone who’s built and run a real pipeline — fast-moving, high-volume, and full of serious prospects — and can turn qualified leads into signed, multi-advisor deals...Full time
$165k - $206k per year
...career opportunities across engineering, manufacturing, research, sales, and technology. As a foundation-owned company, ZEISS is committed... ...cinema lenses, and precision optical systems. What’s the role? The Head of Sales ZEISS Medical Technology Microsurgery is responsible for...Long term contractRemplacementContract workRemote workMonday to fridayFlexible hours- ...covering the most popular Linux distributions, end-of-life systems, programming languages, and much more. We’re looking for a Head of Direct Sales to lead TuxCare’s direct sales organization across North America and EMEA. Reporting to the Chief Revenue Officer, you will...Full timeRemote workWorldwideFlexible hours
- ...One Core Media, a Toronto-based digital marketing agency, is hiring a Head of Sales to design and lead our commercial engine. This player-coach role requires proven agency-side sales leadership and direct people management experience. You will build scalable processes,...
- ...Success Matcher Recruitment is seeking a strategic, hands-on Head of Sales to unify our sales lawyer teams under one leader and drive predictable revenue growth. With inbound leads and multiple practice areas, you will own revenue targets and build a scalable sales organization...
- ...revenue per visitor. Catch conversion drops the same day and bring the cause and the fix. Manage our CRO agency and decide with the Head of Growth when work moves in-house. Report CRO KPIs weekly and run the weekly CRO & Funnels meeting. Requirements Fully...Full timeRemote workWeekend work
$200k per year
...Position: Head of Go-To-Market Salary: $200,000 base salary to $400,000 on-target earnings (OTE) Location: This role is Toronto-based... ...our revenue engine. Reporting directly to the CEO, you will own sales, marketing, customer success, account management, and partnerships...Work at office- ...go-to-market strategy in North American sports and culture market (Canada, US). Build and lead a high-performing commercial team (sales, business development, marketing). Drive revenue growth by identifying, targeting, and closing opportunities with sports clubs, entertainment...Long term contractLocal area
- ...insights, and stay ahead of the curve in a rapidly evolving world. Head of Platforms, Americas Your Mission As Head of Platforms for... ...: Drive the full lifecycle of cutting-edge platforms - from pre-sales and strategy to active deployment in production. Engineering-...Work at officeRemote workHome office
- ...Join to apply for the Head of Customer Success role at Kinsta® Kinsta is one of the top‑managed WordPress hosting companies, with a... ...such as upsells and renewals. The Account Management team within our Sales department is responsible for these efforts and is one of the...Remote workFlexible hours
- This role is open to Canada based candidates Only About Search Atlas Search Atlas is an agentic marketing platform. We combine SEO, content, site management and AI automation into one system. ~$30M+ ARR, 215 employees, thousands of active customers ~ Category creators...Hourly payRemote work
$160k - $180k per year
...and we are looking for ambitious people to join our mission. About The Role Hi, I’m Sarah, Chief of Staff at Loop. I'm hiring a Head of Risk to take ownership of the day-to-day risk function at Loop, owning everything from KYC/B and AML to credit risk, collections, and...InternshipLive InWork at officeImmediate startTrial period- ...We're looking for an exceptional Head of Growth to own paid customer acquisition across our portfolio of youth and adult sports brands, including soccer, basketball, and volleyball, operating throughout the Greater Toronto Area and South Florida. You'll take full ownership...Local area
- ...Reports to: CEO Location: Toronto (Hybrid) Compensation: 180k + performance bonus We’re looking for a Head of Partnerships to help lead CanadaVisa’s next stage of growth. You’ll build on our audience, established relationships and technology to grow our partnerships...Internship
- ...Head of Risk, Payments Location: Toronto Department: Product and Engineering Reports to: SVP of Product and Engineering Build trust into the future of global payments Veem helps businesses move money across borders with greater speed, visibility, and control...Long term contract
- ...Overview Head of Technology role at Kainos. Join to apply for the Head of Technology role at Kainos . At Kainos, we’re problem solvers, innovators, and collaborators, driven by a shared mission to create real impact. We are a people-first culture where ideas are...Long term contractFull timeLive InShift work
$170k - $220k per year
...across several leaders and, often, the CEO. We're hiring a full-time Head of Operations to become the operational backbone of the company:... ...full-time operational anchor alongside a fractional CFO and VP of Sales , and a true partner to the CEO through a pivotal growth chapter....Full timeInternshipRemote workFlexible hoursShift workWeekend work- ...puts into building products that nonprofits trust. The Role As Head of Product Marketing, you'll build and lead the product marketing... ...Product-Led Growth strategy, and partner closely with Product, Sales, Customer Success, and Marketing to bring launches to market. This...Local areaRemote workWorldwide
- ...we partner with Aeroplan and other leading Canadian financial and telecom brands. About the role Chexy is hiring its first CMO / Head of Marketing to own how Canadians come to know, try and stick with Chexy. You report to the CEO, sit on the leadership team, and own...For contractorsWork at office
- ...driven environment, we want to hear from you!**The Opportunity**The Head of Portfolio & Brand Strategy is responsible for defining and... ...Manager while partnering closely with the Head of Innovation, VP Sales, and Director of Trade Marketing to develop integrated commercial...Long term contractFull timeInternshipRemote workShift work
- ...companies lose revenue. We fix that. Now we’re installing a Head of GTM to turn founder-driven strategy into repeatable enterprise... ...Publishing ICP Turn positioning into enterprise-grade messaging Arm Sales with narrative that wins Build case studies that actually...InternshipWork at officeRemote workHome officeFlexible hours
- ...an individual You are passionate about technology, innovation, and investment RECRUITMENT PROCESS: ~ Introductory call with our Head of HR ~ Pre-case with our COO & MD ~1 Case Study with our VP ~ Final on-site interview with Managing Director, CEO, and coffee...Full timeWork at officeLocal areaWorldwide
Do you want to receive more vacancies?
Subscribe and receive similar vacancies to Head of Sales. Be the first to apply!
