Head of Sales Enablement

USA & Canada (Remote)

Director

WHAT YOU' 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:

  • 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 WE OFFER:

  • 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.

STEPS OF THE SELECTION PROCESS:

  • 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.

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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GET TO KNOW US

Explore our journey, the guiding principles that shape our work, and meet the talented individuals who make it all happen.
We'd love for you to get to know us!

EXPLORE WHO WE ARE

Our
Values

  1. Responsibility
  2. Respect
  3. Radical Curiosity

Our values are more than words on a wall. They're the foundation of how we work, create, and collaborate. Since our early days, these core principles have shaped our culture. We embrace our values and we use them as a compass to as we navigate our work, team interactions and most importantly, our client communications.

  1. RESPONSIBILITY

    We have a responsibility to the marketplace and our clients to demand better from the digital ecosystem and leverage the digital ecosystem for better, minimizing ad fraud and invalid traffic and improving brand safety and viewability.

  2. RESPECT

    Respect for our colleagues and people/the consumer by delivering experiences at their specific level of need, with the right creative messaging, at the right time, regardless of channel — and inclusive of where they are spending more of their physical and media time as those touch points converge rapidly.

  3. RADICAL CURIOSITY

    Radical curiosity drives innovation and results for our clients, constantly testing and learning the technology and optimization levers in a platform that will drive results underpinned by people-optimized data and technology.