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Salary: CAD 120,000 - 140,000 / annual
Owner is an AI-native platform helping local business owners (starting with restaurants) succeed by consolidating tools for websites, online ordering, CRM, POS, and more. The company has generated tens of millions in revenue since 2020, processed over a billion dollars in online orders, and helped 20,000+ restaurant owners save nearly $200 million in fees. Owner is remote-first with headquarters in San Francisco and a sales hub in Toronto, with a team of several hundred including talent from Shopify, HubSpot, DoorDash, ServiceTitan, and Stripe.
The Revenue Enablement Specialist will own and evolve Owner's XDR (SDR & BDR) enablement program, serving as a bridge between sales frontline managers and the broader revenue organization. This role is ideal for someone with direct sales experience (SDR, BDR, AE, or sales leadership) who is excited to build training, onboarding, and development programs that drive measurable impact.
Key responsibilities include:
- Program Ownership & Strategy: Own the XDR Enablement Roadmap, Quarterly Plans, and Monthly Sprints. Continuously iterate on programs based on rep performance, manager feedback, and business priorities. Lead enablement projects and execute proper change management processes across the XDR team.
- New Hire Onboarding: Execute and continuously improve Owner's monthly XDR onboarding program in Toronto. Accelerate new XDRs' time to value and productivity by delivering a world-class XDR Academy and Onboarding Experience. Fundamentally impact the organization's ability to scale by reducing ramp time for new XDR team members.
- Rep Up-skilling & Development: Own and maintain all XDR training content, ensuring it stays relevant as Owner evolves. Build competency-based training that prepares top XDRs for promotion into AE roles. Create clear development paths for skill-building, performance improvement, and career growth.
- Knowledge Management: Own XDR-specific documentation within Owner's knowledge base. Ensure enablement content is easy to find, up to date, and actionable. Create new sales plays, talk tracks, and resources that help reps win.
- Cross-Functional Collaboration: Partner closely with XDR frontline managers to continuously improve training and program effectiveness. Collaborate with broader Revenue Enablement team and cross-functional stakeholders to move XDR initiatives forward. Act as a force multiplier for sales leadership by translating strategy into execution.
You will work primarily with XDR frontline managers, the Revenue Enablement team, and cross-functional stakeholders including AE Leadership, Product, Marketing, and RevOps.
Location: Toronto-based role with a hybrid schedule (2 days/week in-office). During monthly new-hire onboarding, this role is expected to be in-office 5 days/week (approximately 2.5 weeks per month).
Requirements:
- 3–5+ years of experience in sales (SDR, BDR, AE, and/or sales leadership) with a proven track record of exceeding quota
- Experience leading, coaching, or supporting SDR/BDR teams as a manager, senior rep, or enablement partner
- Demonstrated history of top performance in a quota-carrying SDR or BDR role
- Hands-on experience training sales reps, improving sales processes, or building scalable workflows that drive performance
- Proven track record of taking ownership of projects end-to-end and driving them to impact, not just completion
- Exceptionally detail-oriented and organized, with high standards for quality, consistency, and follow-through
- Clear, confident communicator who can navigate ambiguity, align stakeholders, and move work forward in a fast-changing environment
- High energy, positive, and deeply motivated by helping sales talent grow, win, and raise the bar across the team
