Talent Development Functional Leader (14-month contract)

Are you excited to shape how people grow, perform, and build the skills they’ll need for what’s next at Jobber?

Then Jobber might be the place for you! We’re looking for a Talent Development Functional Leader to be part of our People department. This is a 14-month contract (parental leave).

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. That’s why we put the power and flexibility in their hands to run their businesses how, where, and when they want! 

Our culture of transparency, inclusivity, collaboration, and innovation has been recognized by Great Place to Work, Canada’s Most Admired Corporate Cultures, and more. Jobber has also been named on the Globe and Mail’s Canada’s Top Growing Companies list, and Deloitte Canada’s Technology Fast 50™, Enterprise Fast 15, and Technology Fast 500™ lists. 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 team : 

The People team at Jobber builds an environment where the very best people can do amazing work. From your first point of contact with one of our recruiters, through your onboarding to your performance and time in the company, the People team is here to help you be successful during every aspect of your time at Jobber. 

A part of our larger People department, the Talent Development team focuses on helping the people who help small businesses to be successful. We ensure that Jobberinos are equipped to be successful by making sure they have access to the right support and resources, allowing them to maximize performance and impact in their roles.

The role : 

Strategic Talent Development Leadership

• Own and evolve Jobber’s Talent Development strategy, ensuring alignment with business priorities, performance goals, and future workforce needs.
• Be a trusted thought partner to business leaders (using insight and performance data to shape solutions that drive real impact, providing insight and recommendations that solve root causes, not just symptoms). 
• Proactively partner with People Business Partners, senior leaders, and teams to co-create solutions that address root causes and drive real performance impact.
• Design holistic solutions that move the dial on performance and growth (i.e. training,  coaching, facilitation, org design, process improvements, etc.)

Company-Wide Learning & Performance Enablement

• Oversee end-to-end employee learning across Jobber — from onboarding that ramps people fast, to functional skills training that closes real gaps. 
• Partner with teams and leaders to make learning stick, empowering them to connect development to real work, not just one-off events.
• Oversee Jobber’s coaching strategy: from individual coaching to building coaching capability in our leaders.
• Lead our annual company-wide Professional Development Day, partnering with Employee Experience to ensure it aligns with strategic priorities and reinforces a culture of connection and growth.
• Facilitate high-impact learning experiences for all employees to embed practical skills and mindset shifts.

Leadership Development

• Design, deliver, and facilitate leadership development pathways for new, emerging, and experienced People Leaders.
• Ensure our leadership programs build trust, clarity, and capability for high-performing teams.
• Own the design and delivery of our annual Leadership Team offsite, aligning it with business strategy and team effectiveness.

 Innovation, AI & Future-Ready Learning

• Pioneer new approaches for learning — blending AI, emerging tech, and human connection to make development more relevant, scalable, and accessible.
• Identify and test tools that enhance how we design, deliver, or measure learning, ensuring they add real value for our people and the business.
• Build foundational AI literacy capabilities, supporting a culture where AI is a trusted digital colleague.
• Stay ahead of trends in the learning space and test what works for Jobber.

Measurement & Performance Impact

• Define and track clear KPIs tied to performance, skills development, engagement, retention, and performance shifts.
• Connect all development efforts back to real business outcomes (i.e. retention, mobility, succession planning,  future readiness, etc.)
• Continuously gather feedback, iterate fast, and share learnings to raise the bar.

Team Leadership 

• Lead and develop a high-performing Talent Development team, fostering a culture of curiosity, experimentation, and accountability.
• Collaborate closely within the Talent team and the broader People Team to ensure Talent Development is integrated with Talent Acquisition, Internal Mobility, Coaching, and Employee Experience.
• Model how to break down silos and build a consistent, high-impact approach to developing Jobberinos at every level.

Who you are:

• You’re a strategic builder. You connect L&D to business performance, talent growth, and future workforce needs — not just training for training’s sake.
• You’re a trusted thought partner. Stakeholders count on you for insight, candour, and practical recommendations that solve real problems.
• You’re insight-driven. You turn metrics and data into meaningful stories, always asking what’s the root cause, what will actually drive impact — and you adapt fast when the evidence says you should to guide priorities and show results.
• You’re curious and innovative. You stay ahead of trends, experiment with new ideas (including AI and emerging tech), and share what you learn so everyone grows.
• You develop people. You lead by example, coaching your team and our leaders to stretch, grow, and deliver. You make complex ideas clear and bring people along for the ride.
• You’re humble, supportive, and you give a shit. You show up with empathy and trust, and you know that great talent development is a partnership — not a silo.

To be successful, you should have:

• Proven experience leading high-performing teams and functions in Talent Development, Learning & Development, Organizational Development, or a related field, ideally in high-growth, scaling organizations. 
• Expertise in building and delivering strategic, company-wide learning that drives real business impact (including Leadership Development, succession planning, high potential programs, etc.)
• Strong project management skills with the ability to juggle multiple priorities and work cross-functionally with stakeholders at all levels across the organization
• Excellent communication and facilitation skills
• Bonus: Experience implementing AI/ML tools or designing for digital-first learning ecosystems.

Compensation: 

At Jobber, we believe that compensation should be transparent, fair, and reflective of your experience and growth. This role has a minimum annual salary of $151,200, a midpoint of $177,900, and a maximum salary of $204,500, designed to show the progression from learning the ropes to truly excelling.

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. The higher end of the range is reserved for those who have demonstrated deep expertise and lasting contributions, while offers below the midpoint reflect strong potential with room to develop. This approach ensures that compensation aligns with both an individual’s current capabilities and their opportunity for future growth.

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. Your professional growth matters to us too! You’ll have access to a dedicated talent development program that includes career coaching and opportunities for career development.

We believe in transparency and open conversations about compensation. If you have any questions about our approach, we’re happy to discuss them throughout the hiring process!

Please note: This role will require North American travel, up to 20% to support our learning programs.

What you can expect from Jobber:

• A total compensation package that includes an extended health benefits package with fully paid premiums for both body and mind, retirement savings plan matching, and stock options.
• 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.
• Support for all your breaks: from vacation to rest and recharge, your birthday off to celebrate, health days to support your physical and mental health, and parental leave top-ups to support your growing family.
• A unique opportunity to build, grow, and leave your impact on a $400-billion industry that has no dominant player...yet.
• To work with a group of people who are humble, supportive, and give a sh*t about our customers. 

We believe that diverse teams perform better and that fostering an inclusive work environment is a key part of growing a successful team. We welcome people of diverse backgrounds, experiences, and perspectives. We are an equal opportunity employer, and we are committed to working with applicants requesting accommodation at any stage of the hiring process.

A bit more about us:

Job by job, we’re transforming the way service is delivered. Your lawn care provider, home cleaning service, plumber or painter could use Jobber to better connect with their customers, save time in the office, invoice faster, and get paid! We’re bringing tens of thousands of people together with technology to deliver billions of dollars a year in services to happy customers. Jobber exists to help make these small businesses successful, and when they’re successful we all win!