Head, Sales Enablement

Job description

Join us to build a more rewarding financial future for all Canadians At Neo, we’re on a mission to build a more rewarding financial future for all Canadians. Life at a rapidly scaling tech startup isn’t for everyone. It’s complex, fast-paced, high-pressure, but also incredibly fulfilling. Since its founding in 2019, Neo has gained incredible traction and is one of the fastest-growing fintech companies in Canada. - #1 on Deloitte’s Technology Fast 50 for 2023, 2024, and 2025 https://www.newswire.ca/news-releases/neo-financial-achieves-first-ever-three-peat-win-as-number-one-on-deloitte-s-technology-fast-50-list-889692540.html — the first company ever to achieve a three-peat at the top! - #1 Fastest Growing Company in Canada for 2024 by Globe & Mail https://www.businesswire.com/news/home/20240927952651/en/Neo-Financial-Ranks-No.-1-on-The-Globe-and-Mail%E2%80%99s-2024-List-of-Canada%E2%80%99s-Top-Growing-Companies - Top-ranked mobile apps and credit cards - Team of 500+ people - 1M+ customers - 10K+ retail partners 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? 🇨🇦 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 WORKING AT NEO: The people who thrive at Neo are resourceful, growth-oriented, and driven to win. We hold ourselves to high standards because we’re on a mission that matters: to build a more rewarding financial future for all Canadians. As individuals and as a team, we constantly challenge ourselves and each other to raise the bar and deliver exceptional experiences for our customers. Our commitment to customer success drives everything we do, from building world-class products to providing exceptional support at every step of their journey. If this resonates with you, keep reading. We trust, respect, and support each other. This means honest conversations, constructive input, and empowering each other to move fast and think big. You’ll be surrounded by people who push you to be your best. We primarily collaborate in person across our Calgary, Winnipeg, and Toronto offices, where ideas move quickly and teams build momentum together. As we continue to scale and evolve, we’re looking for builders, innovators, and problem solvers who thrive on challenge–people who would rather blaze a trail through uncertainty than follow a well-paved path. At Neo, ownership is part of how we think and operate. For select roles, equity participation reinforces that mindset by giving employees a direct stake in the company’s long-term success. Regardless of role, every team member is expected to think like an owner and make decisions that move the business forward. APPLY WITH US: 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. By continuing with your application, you agree to the Candidate Privacy Notice https://www.neofinancial.com/candidate-privacy-policy.pdf, which guides how we process your personal information for the purpose of your application. Neo Financial leverages artificial intelligence (AI) to reinforce our candidate evaluation process, including the initial assessment of applications and screening of candidates. These tools support our recruitment team; however, all final hiring decisions are made by humans and are not based exclusively on automated processing. If you require further information regarding our data processing practices, please contact us. We are hiring for an open, vacant position.