Head, Sales Enablement

Neo Financial

• $120K — $150K *
Finance & Insurance
8 - 10 years of experience
Job Overview by Ladders

Qualifications

  • 8+ years in Sales Enablement, Revenue Operations, or a related field, with 3 years in a senior leadership role
  • Experience in fintech, financial services, B2B or high-growth D2C business
  • Background in national field sales or Activations-type environment preferred
  • Track record of building scalable enablement programs for high-volume frontline sales teams
  • Experience owning the full enablement lifecycle: recruitment, onboarding, training, performance management, and compensation
  • Ability to build scalable infrastructure and drive outcomes across departments without direct ownership

Responsibilities

  • Own recruitment pipelines and workforce planning, defining role profiles and addressing capacity gaps
  • Design and manage end-to-end onboarding for field reps, covering pre-day-one to 90-day milestones
  • Build modular training infrastructure covering pitch delivery, objection handling, compliance, and product knowledge
  • Measure training effectiveness and drive continuous improvement
  • Develop rep-level scorecards and performance frameworks for the sales team
  • Collaborate with senior management to design variable compensation programs
  • Evaluate and implement tech tools to enhance field rep productivity

Benefits

  • Equity ownership opportunities to share in company growth
  • Flexible health benefits and life insurance
  • 21 days PTO plus public holidays and personal leave
  • Health and personal spending accounts
  • Discounts through partner networks and early access to Neo products
  • Parental top-up and equity vesting during long-term leave
  • Opportunities for team events and company-wide education huddles
Full Job Description
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.

What You'll Do

People & Pipeline
  • 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


Training & Development
  • 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

Performance & Compensation
  • 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


Systems & Tooling
  • 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
What You Bring
  • 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


Total Rewards

As Neo continues to grow, we're committed to offering a competitive, market-leading rewards program that reflects the impact our team members make. In addition to salary, our program includes equity - empowering employees to share directly in our momentum today and in the meaningful value we create for years to come.
  • 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.


What does life as an Owner at Neo Include?

C🇦 You will redefine the financial landscape with top talent in Canada to help everyday Canadians win, and grow quickly while doing it

For eligible roles, ownership structure that enables you to share in our path to victory

Earn BIG with our short term incentive plans (STIP)

Collaborating with the brightest minds to build something meaningful, united by a shared commitment to innovation, curiosity, and excellence

♥🩹 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

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