Head of Sales Enablement

Growth
Director
USA & Canada (Remote)
What You'll Do
  • Build and lead AI Digital's Sales Enablement function — strategy, processes, and operating model from scratch.
  • Design and scale onboarding, training, and certification programs across Sales, Client Success, and other client-facing teams — reducing ramp time and ensuring consistent knowledge of products, methodology, and competitive positioning.
  • Become a subject matter expert on AI Digital's products — Elevate, AI Labs, Managed Service, Smart Supply, and beyond.
  • Partner with Product, Product Marketing, Client Service, and Strategy to translate new releases into effective training materials — and maintain a centralized knowledge base with up-to-date collateral, battle cards, FAQs, and product documentation.
  • Coach sales teams on presentations, storytelling, and executive conversations — using performance data to identify gaps, drive training initiatives, and manage the tools and platforms that support it all.
  • Work with Sales Leadership to establish KPIs and optimize programs — and create the collateral, battle cards, one-pagers, and demo scripts that support the team day to day.
  • Build and scale the Sales Enablement team as the organization grows.
What You Bring
Must-have
  • 10+ years in Sales Enablement, Revenue Enablement, Sales Training, or a similar leadership role within AdTech.
  • Proven experience building or significantly scaling a Sales Enablement function from scratch.
  • Strong understanding of B2B adtech and media sales, complex solution selling, and consultative sales methodologies.
  • Experience designing onboarding programs, certification frameworks, and continuous learning initiatives.
  • Track record of cross-functional partnership with Growth, Product, Marketing, and Executive Leadership.
  • Hands-on — able to personally create training materials, presentations, and sales collateral when needed.
Nice-to-have
  • Experience in programmatic advertising, AdTech, or digital media.
  • Hands-on experience with sales enablement platforms (Highspot, Seismic, Showpad, Mindtickle) and revenue intelligence tools (Gong, Chorus, Clari).
  • Experience implementing LMS and certification platforms.
  • Background in product marketing, sales engineering, or enterprise software training, ideally in a high-growth environment
What You Get
  • Competitive salary
  • Work from anywhere: Fully remote to suit your lifestyle.‍
  • Unlimited PTO that we actually encourage you to use — for adventures, recovery, or just because.
  • Growth-focused environment: Access to learning resources and clear pathways for growth.
  • Fun team events: From virtual pasta-making to yoga sessions, we make remote feel close.‍
  • A culture of trust: We cut the red tape — open talk, ownership, and getting things done together. Results over rules, always.
Hiring Flow
  • First Round: Interview with direct manager Chief Strategy Officer
  • Second Round: Interview with Chief Revenue Officer
  • Third Round: Interview with the CEO of the company
  • Forth Round: Assignment completion & presentation to the team

Additional Chemistry Interviews might be conducted with SVPs of Growth and COO

AI Digital does not discriminate on the basis of race, color, religion, gender identity or expression, national origin, age, military service eligibility, veteran status, sexual orientation, marital status, disability, or any other protected class in terms of employment. We support workplace diversity and believe strongly that it contributes to a broader collective perspective that consistently leads to better products and a better company. We are working hard to increase the diversity of our team.

Location & Eligibility

Note: This role is open to applicants from:

  • Canada
  • USA

Please note that we’re unable to consider applications from outside these regions. Thanks for your understanding!

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