Director, Sales Enablement

About Jobber

Jobber is dedicated to empowering small service businesses—plumbers, painters, landscapers, and more—by transforming how they operate through technology. The platform enables professionals to quote, schedule, invoice, and collect payments efficiently, delivering a seamless and professional experience to their customers. In a rapidly evolving market with increasing customer expectations, Jobber empowers these businesses to run operations flexibly, anytime and anywhere.

Renowned for a culture valuing transparency, inclusivity, collaboration, and innovation, Jobber has received multiple accolades including Great Place to Work and Canada's Most Admired Corporate Cultures. The executive leadership brings over 30 years of industry expertise, with significant growth milestones achieved since 2011.

Team Overview

The Sales Enablement & Operations team ensures the go-to-market organization maintains agility without compromising preparedness. They create systems, tools, and development programs translating strategy into execution—covering forecasting, planning, compensation, technology integration, and seller skill enhancement. The team is subdivided into Sales Operations, Revenue Technology, Sales Planning & Operations, and Enablement Programs pillars.

Role Summary

Reporting to the Senior Director of Sales Enablement & Operations, the Director of Sales Enablement leads the Enablement Programs pillar. This role is responsible for equipping every sales representative with the necessary skills, confidence, and readiness from onboarding through product launches. Leading a team of five to six professionals and collaborating with peers heading other pillars, the Director is focused on measurable outcomes such as ramp speed, pipeline growth, and revenue generation rather than mere activity completion.

Key Responsibilities

• Develop and execute strategies for onboarding, training, certification, and coaching across the sales organization.
• Manage and enhance ramp programs and certification standards, clearly defining the criteria for sales readiness.
• Oversee enablement initiatives for product, pricing, and process launches with detailed timelines aligned to launch dates.
• Create and maintain structured, repeatable playbooks and coaching frameworks adapted to evolving products and markets.
• Implement AI technologies to enhance enablement activities including content generation, coaching feedback, practice sessions, and knowledge management.
• Collaborate with Product, Product Marketing, Sales leadership, and Customer Success to align enablement priorities with business objectives and ensure successful launch adoption.
• Define and track success metrics extending beyond training completion to include ramp duration, certification success, and the impact on pipeline and sales results.

Candidate Profile

• Significant experience in sales enablement, revenue operations, or sales leadership, particularly in designing and managing onboarding, training, and certification programs at scale.
• Demonstrated leadership in managing managers and developing team capabilities alongside field performance improvement.
• Proven success leading enablement for product or pricing rollouts within B2B SaaS settings, including creating actionable workback plans.
• Proficiency with AI tools applied to enablement functions such as content creation, roleplay coaching, and knowledge sharing.
• Expertise in building scalable and structured learning frameworks beyond episodic training events.
• Strong skills in stakeholder engagement at the director level across multiple departments, influencing product roadmaps and go-to-market strategies.
• Comfortable navigating ambiguity and instituting foundational enablement processes.
• Excellent communication skills, both written and verbal.
• Results-driven mindset with an emphasis on impactful outcomes rather than mere activity metrics.

Compensation and Benefits

The role offers a transparent and competitive base salary range from $181,400 to $245,500 annually, reflecting various experience and expertise levels. Package components include equity, annual health and wellness stipends, retirement contribution matching, and fully paid extended health coverage addressing both physical and mental health. The position also provides access to career development, coaching, and leadership programs tailored to foster professional growth.

Location

This position requires physical presence in one of the company’s key hub cities: Edmonton, Toronto, Vancouver, or Kitchener-Waterloo, to facilitate collaboration and connection.

Why Join Jobber

• Comprehensive total compensation with benefits covering health, retirement, and equity participation.
• Supportive talent development initiatives including coaching and leadership development opportunities.
• Chance to innovate and impact a large, fragmented $400 billion industry.
• A culture marked by humility, collaboration, and deep customer commitment.

Equal Opportunity

Jobber values diversity and fosters an inclusive environment. They are committed to equal employment opportunities and provide accommodations throughout the hiring process as needed.