Head Of Revenue (B2B Media)

TL;DR

Head Of Revenue (B2B Media): Leading the transition from demand gen products to integrated brand-to-demand programs for enterprise clients with an accent on revenue system design and strategic deal closing. Focus on building repeatable revenue products, aligning sales and delivery functions, and scaling predictable revenue growth.

Location: Must be based in Canada (Remote or Hybrid)

Salary: $200,000 - $245,000 CAD per year

Company

A rapidly growing independent media tech company helping professionals succeed in the age of AI through a portfolio of influential digital publications.

What you will do

• Pitch, negotiate, and close high-value strategic deals for complex integrated programs.
• Design custom multi-channel campaigns and convert patterns into repeatable packaged offers and pricing.
• Establish a Program Delivery function with clear SLAs and reliable handoffs from sales.
• Audit and restructure the sales organization, aligning segmentation, targets, and compensation.
• Implement operating cadences including weekly pipeline reviews, forecasting, and KPI dashboards.
• Coach the sales team on integrated program selling, deal structuring, and pricing discipline.

Requirements

• VP-level experience leading a revenue or commercial function, preferably in B2B media or marketing services.
• Proven track record of personally closing six-figure strategic deals.
• Expertise in integrated marketing and media campaign sales (newsletters, lead gen, sponsorships).
• Experience transforming custom deals into repeatable revenue products and sales playbooks.
• Ability to synchronize Sales, Product, Delivery, and RevOps into a single operating system.
• Must be based in Canada.

Nice to have

• Direct experience in the events industry.
• Experience selling to B2B SaaS or tech buyers.
• Experience scaling a Program Delivery or AdOps function from scratch.

Culture & Benefits

• Impact-driven environment combining startup agility with agency creativity.
• Full-time employment with a comprehensive benefits package.
• Eligible for a discretionary bonus.
• Flexible work arrangements including remote or hybrid options depending on location.