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 that values your expertise.‍
  • 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.
  • Health insurance and ClassPass coverage: supporting your well-being both inside and outside of work.
Hiring Flow
  • Interview with the Chief Strategy Officer: Meet with your direct manager to discuss your experience, the role, key responsibilities, and expectations.
  • Interview with the Chief Revenue Officer: A conversation focused on your experience, skills, and alignment with the team and business goals.
  • Interview with the CEO: An opportunity to discuss your experience and overall fit with the company.
  • Assignment & Presentation: Complete a practical assignment and present it to the team.
  • Offer: If successful, you’ll receive an offer to join our team.

Chemistry interviews with the SVP of Growth and/or COO may be scheduled as part of the process.

Location & Eligibility

This role is open to applicants from the United States and Canada.

Please note that we’re unable to consider applications from outside these locations.

Thanks for your understanding!

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