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Salary: CAD 165,000 - 0 / annual
Owner is an AI-native platform helping local business owners (starting with restaurants) succeed by replacing fragmented tools with a unified system covering websites, online ordering, CRM, POS, and more. The company has generated tens of millions in revenue since 2020, processed over a billion dollars in orders, and helped 20,000+ restaurant owners save nearly $200 million in fees. Owner is remote-first and globally distributed, with a sales hub in Toronto and headquarters in San Francisco.
You will own and mature the enablement program specifically for Owner's Account Executive organization. This is a hands-on role ideal for someone with lived closing experience as a top-performing AE or sales leader who understands deal cycles, discovery, and negotiation.
Key responsibilities:
- Design and execute an outcomes-focused AE enablement roadmap with quarterly plans and monthly sprints, ruthlessly prioritizing initiatives with the highest revenue impact.
- Build, deliver, and continuously refine the AE onboarding program. You'll spend significant time in-office driving hands-on training, coaching, and culture fit to set reps up to win.
- Develop competency-based training programs in discovery, demos, pipeline management, and negotiation. Create role-transition programs for BDR→AE advancement and leverage simulation tools for at-scale coaching.
- Build and improve eLearning modules, battlecards, playbooks, talk tracks, competitor guides, and process documentation. Create engaging, scalable content that drives adoption and measurable performance gains.
- Leverage AI tools to enhance training design, personalize learning paths, automate content creation, and drive measurable impact on sales performance.
- Partner cross-functionally with product, marketing, and RevOps to ensure enablement stays connected to business priorities, product updates, and frontline needs.
- Measure everything against revenue outcomes: rep productivity, deal velocity, quota attainment, and pipeline impact.
You'll work day-to-day with senior sales leaders, frontline managers, sales enablement leadership, marketing, and product teams. The role requires hyper-flexibility and collaboration—you're an activator, not a blocker.
REQUIREMENTS:
- 3–5 years of sales experience with real closing or quota-carrying exposure; ideally a top performer who understands deal cycles and the AE grind
- 6+ years in sales enablement, building and scaling programs that demonstrably drive revenue outcomes
- Track record of translating sales motion and rep challenges into scaled training and development programs
- Strong hands-on experience with Salesforce, Salesloft, Outreach, Avvara, and eLearning platforms (WorkRamp, etc.)
- Outstanding coaching and facilitation skills; comfortable training groups, 1:1 coaching, and translating feedback into development plans
- Passion for leveraging AI to transform how enablement is built and delivered
- Organized, adaptable, and hyper-collaborative with leadership
- Obsessed with measuring enablement's direct impact on revenue, pipeline, and quota attainment
