Head, Sales Enablement

Neo Financial; Toronto; On-site; CAD 140,000 - 160,000; Full time

Benefits offered by this job

Equity ownership

Health benefits

Life insurance

Paid time off 21 days + holidays

Health spending account

Discounts with partner network

Equity vesting during long-term leave

Early access to Neo products

Company events

Learning opportunities

Job summary

Neo Financial is seeking a Director, Sales Enablement – Activations to lead recruitment pipelines, onboarding, training, and compensation design for Activations across Canada. You will partner with VP of Sales, Finance, and Regional leaders to drive scalable enablement programs and measurable outcomes.

You will own the full enablement stack—from recruitment and onboarding to training, performance management, and tooling—while scaling the framework for Neo’s other sales channels as the mandate

Qualifications

• 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 is an asset.

Responsibilities

• Own the recruitment pipelines and workforce planning for the Activations channel, defining role profiles, partnering with Talent Acquisition, and flagging capacity gaps before they become performance gaps.
• Design, develop, 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; 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 representative-level scorecards and performance frameworks across Activations; design the review cadence and coaching tools that Regional Sales Directors 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; own calculation logic and payout accuracy.
• Evaluate, implement, and manage the technology stack that enables field rep productivity, scheduling, and performance visibility; lead end-to-end vendor selection and adoption.
• Design all systems and frameworks to scale across Neo’s other Sales channels as the mandate expands.
• Own the full enablement stack for Activations – recruitment, onboarding, training, performance management, compensation design, and tooling that ties it all together.

Skills

Sales Enablement

Leadership

Revenue Operations

Fintech experience

Cross-functional collaboration

Job description

Director, Sales Enablement – Activations at Neo

Responsibilities

• Own the recruitment pipelines and workforce planning for the Activations channel, defining role profiles, partnering with Talent Acquisition, and flagging capacity gaps before they become performance gaps.
• Design, develop, 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; 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 representative‑level scorecards and performance frameworks across Activations; design the review cadence and coaching tools that Regional Sales Directors 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; own calculation logic and payout accuracy.
• Evaluate, implement, and manage the technology stack that enables field rep productivity, scheduling, and performance visibility; lead end‑to‑end vendor selection and adoption.
• Design all systems and frameworks to scale across Neo’s other Sales channels as the mandate expands.
• Own the full enablement stack for Activations – recruitment, onboarding, training, performance management, compensation design, and tooling that ties it all together.

Qualifications

• 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 is an asset.
• Demonstrated track record building and scaling enablement programs for high‑volume front‑line sales teams, including field sales, retail, or direct‑to‑consumer environments.
• 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.

Benefits

• Competitive base salary aligned with market ranges; flexibility to tailor cash and equity mix to match long‑term goals.
• Equity ownership eligibility for full‑time team members, providing long‑term value tied to company performance.
• Health benefits and life insurance.
• Paid time off: 21 days plus statutory holidays, with additional personal leave.
• Health and personal spending accounts.
• Discounts through partner network.
• Equity vesting during long‑term leave and parental leave top‑up.
• Access to early use of Neo products and discounts on Neo mortgages.
• Regular company events and learning opportunities.
• Compensation Range: CA$140K - CA$160K.

Equal Opportunity & Screening

Neo Financial is an equal opportunity employer. All qualified applicants will receive consideration without regard to race, color, religion, sex, national origin, disability, or veteran status. Candidates for this position are required to undergo a security screening, including a criminal records check and a credit check.