Head, Sales Enablement

Neo Financial•Calgary, AB

13d•Onsite

About The Position

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.

Requirements

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
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

Nice To Haves

Background in a national field sales or Activations-type environment would be considered an asset

Responsibilities

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

Benefits

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): At Neo, you don’t just work here, you own a piece of what we’re building. 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.
Earn BIG with our short term incentive plans (STIP)
Flexible health benefits & life insurance
21 Days PTO + stat holidays, and personal leave
Health & 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 & equity vesting during long term leave
Neo night events
Company wide huddles, and education