Our Talent team at Jobber will be offline for Jobber Impact
- our flagship event of the year, bringing Jobberinos together to connect, learn, and celebrate what we're building
- starting October 6th and extending until October 9th. This will be updated automatically on all job posts above our What you can expect from Jobber headline. Director, Sales Enablement Sales Enablement & Operations Jobber exists to help people in small businesses be successful. We work with small home service businesses, like your local plumbers, painters, and landscapers, to transform the way service is delivered through technology. With Jobber they can quote, schedule, invoice, and collect payments from their customers while providing an easy and professional customer experience. Running a small business today isn’t like it used to be—the way we consume and deliver service is changing rapidly, technology is evolving, and customers expect more. Our culture of transparency, inclusivity, collaboration, and innovation has been recognized by Great Place to Work, Canada’s Most Admired Corporate Cultures, and more. With an Executive team that has over thirty years of industry experience of leading the way, we’ve come a long way from our first customer in 2011—but we’ve just scratched the surface of what we want to accomplish for our customers. The Sales Enablement & Operations exists to make sure Jobber’s go-to-market org never has to choose between moving quickly and being ready. Sales Operations, Revenue Technology, Sales Planning & Operations, and Enablement Programs. Director, Sales Enablement & Operations, the Director, Sales Enablement You’ll lead a team of five to six, as a peer to the leads of Sales Operations, Revenue Technology, and Sales Planning & Operations. You’re accountable for outcomes,



not activity — whether reps are actually ready, whether launches actually land in the field, and whether the enablement investment shows up in ramp speed, pipeline, and revenue. The Director, Sales Enablement will: Set the strategy for onboarding, training, certification, and coaching across the sales org, and build, manage, and upskill a team of enablement managers and practitioners. Own ramp programs and certification standards across go-to-market roles, and hold the bar on what “certified and ready” actually means. Lead enablement for new product, pricing, and process launches, building workback plans that trace every training, content, and certification milestone back from the launch date. Build structured, repeatable playbooks and coaching frameworks, and keep them current as products, segments, and motions change. Bring AI into how the team builds and delivers enablement — content creation, coaching feedback loops, practice and roleplay, knowledge access — and into what reps are taught to use in their own workflow. Partner with Product, Product Marketing, Sales leadership, and Customer Success so enablement priorities match what the business needs next, and launches land with sales rather than at sales. Define success beyond completion rates, and report on ramp time, certification pass rates, and downstream impact on pipeline and revenue. Extensive experience in sales enablement, revenue operations, or sales leadership,



including building and running onboarding, training, or certification programs at scale. Demonstrated people leadership experience, including managing managers, and a track record of developing your own team’s skills alongside the field’s. Hands-on fluency with AI tools in enablement work itself: content generation, coaching and roleplay, and knowledge management. Experience building structured, scalable learning frameworks rather than one-off training events. Robust stakeholder management with director-level and senior partners across Product, Marketing, and Sales leadership, and the ability to influence roadmap and go-to-market timing rather than only execute against it. Comfort operating with ambiguity and building infrastructure where none exists yet. We design our compensation to reflect each new hire’s skills, experience against the complexity of the role, ensuring a fair and competitive salary. Our range is intentionally broad to support growth and long-term impact, with fully established hires typically starting around the midpoint. Base salary is just one part of a total compensation package that will include equity rewards, annual stipends for health and wellness, retirement savings matching, and an extended health package with fully paid premiums for body and mind. To support this, the role is open to candidates based in one of our hub cities: A dedicated Talent Development team and access to coaching, learning, and leadership programs to help you grow your career, reach your goals, and unlock your full potential. To work with a group of people who are humble, supportive, and give a sh*t about our customers. We are an equal opportunity employer, and we are committed to working with applicants reque

📌 Director, Data Sales (Canada)
🏢 Jobber
📍 Canada