Head, Sales Enablement

The Role

Neo's Activations channel, face‑to‑face field sales across mall kiosks, campuses, and community locations, is one of our highest‑growth engines, and it is scaling fast. The infrastructure that makes that growth repeatable and sustainable does not yet fully exist. This role is here to build it.

The Director, Sales Enablement will own the full enablement stack for Activations: recruitment, onboarding, training, performance management, compensation design, and the tooling that ties it all together.

This is a builder role. You will be held accountable for outcomes, not just programs.

• Own recruitment pipelines and workforce planning for Activations, defining role profiles, partnering with Talent Acquisition, and flagging capacity gaps before they become performance gaps
• Design and own the end‑to‑end onboarding program for field reps, from pre‑day‑one through 30/60/90‑day milestones

• Build a modular, channel‑specific training infrastructure covering pitch delivery, objection handling, compliance, and product knowledge, and maintain a library of field playbooks for kiosk, campus, and community event environments
• Measure training effectiveness through ramp time and first‑90‑day performance, and drive continuous improvement based on results

• Build rep‑level scorecards and performance frameworks across Activations, and design the review cadence and coaching tools RSDs and District Managers use to develop their teams
• Partner with VP of Sales, Head of Sales and Finance to design and implement variable compensation programs, including volume tiers, SPIFFs, quality adjustments, and clawback mechanics, and own calculation logic and payout accuracy

• Evaluate, implement, and manage the tech stack that enables field rep productivity, scheduling, and performance visibility, and lead implementations end‑to‑end from vendor selection through adoption
• Design all systems and frameworks to scale across Neo's other Sales channels as the mandate expands

• 8+ years in Sales Enablement, Revenue Operations, or a closely related field, with at least 3 years in a senior leadership role
• Experience in fintech, financial services, B2B or a high‑growth D2C consumer business
• Background in a national field sales or Activations‑type environment would be considered an asset
• Demonstrated track record building and scaling enablement programs for high‑volume frontline sales teams, inclusive of field sales, retail, or direct‑to‑consumer environments strongly preferred
• Experience owning the full enablement lifecycle: recruitment, onboarding, training, performance management, and compensation
• Proven ability to build scalable infrastructure and frameworks, and to drive outcomes across various departments without direct ownership of those functions

• Salary: We provide a strong base salary aligned with market ranges, along with the flexibility to tailor your mix of cash and equity to match your longer‑term goals. Final compensation is based on your skills, experience, and scope. For exceptional talent, we’re prepared to go above and beyond.
• Equity Ownership (Where Eligible):
  As a full‑time team member, you share directly in the upside of one of Canada’s fastest‑growing companies. When we win, you win— with real ownership and meaningful long‑term wealth‑building potential tied to our success.

• Redefine the financial landscape and help Canadians win while growing quickly.
• Ownership structure that enables you to share in our path to victory (for eligible roles).
• Earn big with our short‑term incentive plans (STIP).
• Collaborate with the brightest minds on innovation, curiosity, and excellence.
• Flexible health benefits and life insurance.
• 21 days PTO plus statutory holidays and personal leave.
• Health and personal spending accounts.
• A wide variety of discounts through our partner network.
• Access to early use of products and discounts on fixed‑term Neo mortgages.
• Parental top‑up and equity vesting during long‑term leave.
• Neo night events.
• Company‑wide huddles and education.

We believe in equal opportunity and are committed to creating an inclusive climate where everyone can thrive. Customers trust us with their finances, so successful candidates for this position will be required to undergo a security screening, including a criminal records check and a credit check.