As a Director of Sales, you will sell digital advertising, first-party audience data, and Healthcare AI solutions to U.S. pharmaceutical companies and healthcare media agencies. You will primarily be selling to pharmaceutical product managers, omnichannel commercialization teams, and media agency buyers (VP/Director of Media, media planners and strategists). This role is 75% new business development and 25% account management in Year 1. You will start with a small existing book of accounts to upsell and cross-sell, but must build your own net-new pipeline. Approximately 50% of leads are list-supplied, 25% are warm leads, and 25% are self-prospected — expect to drive close to 100% of your own outreach in the first three months as you ramp. This is an expansion hire on a succession track, reporting to the Sales Manager. The base salary is $95,000 – $110,000 CAD, plus commissions and bonuses.
• $90,000 – $110,000 CAD base salary
• Year 1 OTE: $150,000 – $180,000 CAD
• Year 2 OTE: $150,000 – $220,000 CAD
• Residual commission on collected revenue from assigned accounts — accounts you build continue to pay you as long as you retain them
• Commission is paid quarterly and annually
• Top performer on the current team earns approximately $250,000 annually, reached over roughly five years
• Health benefits — partially company-paid — plus a health benefit allowance
• Laptop provided
• Expense account
• 15 vacation days, 3 sick days, 3 personal days
• Flexible extended summer vacations
• Office closed between Christmas and New Year’s
• Quarterly contests and prizes
• Company social events
Our client was founded in approximately 2006 and is privately held with founder majority. Based in North York, Ontario, they are an owned-and-operated digital media publisher with 19 employees company-wide and approximately 10 staff in the North York office. They are in an established growth stage, with 25 to 50% annual revenue growth. The company owns and operates 25+ digital sites with reach across 2,000+ partner sites and more than 100 million web pages. They deliver digital advertising, first-party audience data, and Healthcare AI solutions exclusively to the U.S. healthcare and B2B markets. Because they own their sites outright, they own their data — giving clients proprietary audience and identity data, lower cost-per-reach, and true omnichannel capabilities including content syndication, email, site sponsorships, and audience-segmentation data. Their client list includes Sanofi, Kaiser Permanente, Lundbeck, Takeda, IBM, and Oracle. The culture is driven, results-oriented, and highly collaborative. It is a flat organization where the CEO and COO engage with all levels project-by-project. Strong emphasis on accountability and compensating people well for hitting targets.
• Head Office: North York, Ontario
• Work arrangement: Office-based — 5 days per week. This is not a remote or hybrid role.
• Sales territory: Assigned accounts (not geographic). Primarily the U.S. healthcare market — approximately 75% direct pharmaceutical companies and 25% media and advertising agencies.
• Overnight travel: 5 to 10% (approximately 1 to 2 days per month). Planned U.S. trips to New York, Philadelphia, and Boston; may also include client meetings, industry conferences, and events.
• Hours: Approximately 50 hours per week, Monday to Friday. No regularly scheduled evening or weekend client calls.
• Driver’s licence: Not required.
• 5 to 15 years of direct B2B sales experience
• Consultative, solution-based selling of an intangible product — digital media, advertising, ad-tech, programmatic, or a closely related marketing services product is strongly preferred
• Healthcare media or pharma media background is a home run; DSP, programmatic, or digital publisher experience is ideal. Industry experience is not strictly required — the client will train the right candidate.
• Strong self-sourced hunting track record — must be comfortable generating your own pipeline through outbound prospecting
• Experience selling to marketing, media, or pharmaceutical buyer profiles is an asset
• Stable career history — progressive advancement within companies is a positive signal
• Post-secondary diploma minimum; a degree in Commerce, Marketing, Communications, or a related field is preferred but not a hard requirement
• Must be within approximately 30 to 45 minutes of the North York office (commute over 1 hour is not workable for this role)
• Microsoft PowerPoint — Intermediate (required; you will build tailored pitch decks and follow-up presentations)
• Microsoft Excel — Intermediate
• Microsoft Word — Basic to Intermediate
• Google Drive / Google Docs — Basic
• Salesforce CRM — Basic to Intermediate (asset; training provided)
• Comfortable running online demos and video presentations
• Digital advertising — display, content syndication, email, and exclusive site sponsorships across 25+ owned sites and 2,000+ partner sites
• First-party audience data and audience-segmentation solutions — proprietary data reaching healthcare professionals by specialty and location, plus U.S. consumers, patients, and caregivers
• Healthcare AI solutions — sold into pharmaceutical, hospital network, and healthcare enterprise buyers
• Campaign coverage spans therapeutic areas including diabetes, hepatitis, hemophilia, and women’s health, as well as major U.S. hospital markets
• Primary customers: U.S. pharmaceutical companies (approximately 75% of revenue) and U.S. media and advertising agencies (approximately 25%)
• Industry verticals: pharmaceutical, hospital networks, medical device, health insurance, CPG, and enterprise software and services
• Direct pharma decision-makers: pharmaceutical product managers, omnichannel and commercialization teams, activation teams
• Agency decision-makers: VP and Director of Media, media planners, buyers, and strategists
• Account size: approximately $15,000 to $20,000 USD per month average; $250,000 to $1,000,000+ USD annual account value
• Average sales cycle: 1 to 9 months depending on account size and buyer type
• Typical path to first order: approximately 2 calls or meetings
• Average monthly account spend: approximately $15,000 to $20,000 USD
• Average annual account value: $250,000 to $1,000,000+ USD
• Owned-and-operated publisher model — the company owns its sites and therefore owns its data, providing clients with proprietary first-party audience and identity data
• True omnichannel reach: 25+ owned sites, 2,000+ partner sites, and 100 million+ web pages
• Lower cost base to reach healthcare professionals and consumers compared to third-party data providers
• Residual commission model — reps build a book of business that pays them for as long as accounts are retained
• 20 years in business with a stable, established client base including Sanofi, Kaiser Permanente, Lundbeck, Takeda, IBM, and Oracle
• Growing at 25 to 50% annually with a clear succession and leadership path for the right hire
• 75% New Business Development
• 25% Account Management
On a typical day you will be building and working a self-sourced pipeline of pharmaceutical and agency prospects through personalized outbound outreach (email, LinkedIn, phone). You will be qualifying responses, booking and running consultative meetings (working toward approximately 2 meetings per day across 4 days per week as you ramp), producing tailored follow-up materials including slide decks and written proposals, advancing deals through the funnel, and closing insertion orders and licensing agreements. You will also manage and grow a starter book of existing accounts through upsell and cross-sell activity, maintain Salesforce CRM pipeline discipline, and collaborate with BDRs, customer success, and marketing. In Year 2, this role transitions to approximately 50% selling and 50% player-coach leadership as the CEO steps back from day-to-day sales.
• Approximately 50% list-supplied (target account lists provided)
• Approximately 25% warm leads supplied
• Approximately 25% self-prospected
• Expect to drive close to 100% of your own outreach in the first three months; BDR support scales toward a 50/50 split as the role ramps
• A BDR team provides support over time, but this role requires a genuine self-starter in the early period
• 5 to 10% (approximately 1 to 2 days per month)
• Planned U.S. blitz trips to New York, Philadelphia, and Boston
• May also include U.S. client meetings, industry conferences, and events as required
• Direct mentorship and collaboration with the Sales Manager (10+ years managing this team; also WebHealth’s top sales performer) and the CEO, who currently drives day-to-day sales
• You will shadow and directly inherit knowledge of existing client relationships and sales processes from the CEO as part of the succession plan
• Full product, service, and market training provided — healthcare media industry experience is not strictly required
• BDR support that scales over the ramp period
• Salesforce CRM training provided
• A small existing book of accounts is assigned from Day 1 — you are not starting from zero
• Residual commission model — accounts you build pay you for as long as you retain them; top performer earns approximately $250,000 annually
• Real succession hire — this is not a title change; the CEO is actively planning to transition day-to-day sales responsibility to this person by Year 2
• Established company with 20 years in business, fast-growing (25 to 50% annually), and a named client list that includes Sanofi, Kaiser Permanente, and IBM
• You are not starting from zero — a starter book of existing accounts is provided on Day 1
• Flat organization with direct access to CEO and COO — your ideas and results are visible at the top from Day 1
Just Sales Jobs and our clients are equal opportunity employers. We do not discriminate. All candidates are evaluated solely on performance merit and organizational fit.
If this particular role isn’t the right match, we encourage you to browse our other open positions at https://justsalesjobs.ca/jobs-opening/ and apply for any that interest you. Our recruiters review every resume we receive — and if we have another role that could be a great fit for your background, we will reach out to you directly.
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