Senior Learning Specialist

Are you excited by the prospect of having an impact on the performance and development of employees by building a culture of learning?

Then Jobber might be the place for you! We’re looking for a Sr. Learning Specialist to be part of our People department.

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: 

Reporting into the Senior Manager, Talent Development, we’re looking for a strategic, forward-thinking Sr. Learning Specialist to help shape the future of learning, leadership, and organizational capability at Jobber. This role goes beyond traditional L&D—it’s about embedding innovation into the DNA of how our people grow. You’ll work cross-functionally to identify emerging skill needs, architect transformative learning experiences, and build future-ready leaders who can thrive in a rapidly evolving landscape.

The Senior Learning Specialist will:

• Drive Learning Innovation
  • Design and implement next-gen learning programs using modern methodologies (e.g., cohort-based learning, e-learning, microlearning, AI-enabled platforms).
  • Pilot and scale new learning technologies and modalities that personalize development experiences.
  • Establish metrics to measure learning efficacy, adoption, and ROI; iterate programs based on insights.
• Strategic Capability Building
  • Conduct deep organizational needs assessments to surface future skill gaps tied to business strategy.
  • Partner with business leaders to co-create targeted development interventions that future-proof critical teams.
  • Leverage market intelligence and workforce trends to address capability shifts proactively.
• Foster a Culture of Growth
  • Champion a continuous learning culture rooted in experimentation, agility, and innovation.
  • Build internal communities of practice, peer learning forums, and mentorship networks.
  • Equip managers and leaders to become coaches and learning accelerators for their teams.
  • Design and facilitate engaging workshops, learning sessions, and leadership offsites that spark dialogue, reflection, and behavior change.
• Leadership & High-Potential Development
  • Support succession planning efforts by identifying, assessing, and accelerating top talent.
• Embrace Data & Technology
  • Use learning analytics and talent data to inform personalized journeys and strategic decisions.
  • Explore AI, automation, and digital tools that amplify learning reach and impact.
  • Stay ahead of innovation trends and proactively introduce ideas to evolve our Talent Development strategy.

Who you are :

• A Futurist & Learning Designer: You blend instructional design with trend forecasting to create innovative, human-centred development solutions.
• A Change Agent: You’re energized by change and skilled at influencing mindsets and behaviors across all levels of an organization.
• A Collaborative Partner: You thrive in matrixed environments and are trusted by stakeholders as a consultative, strategic partner.
• An Agile Operator: You bring a startup mindset—test quickly, learn fast, and adapt to feedback.
• Insight-Driven: You use data and storytelling to advocate for bold ideas and continuous improvement.

To be successful you should have : 

• Proven experience in Talent Development, Learning & Development,  Organizational Development, or a related field.
• Proven experience designing and scaling innovative development programs in high-growth or fast-changing organizations.
• Strong understanding of adult learning principles, learning technologies, and workforce of the future trends.
• Experience with leadership development, succession planning, and high-potential programs.
• 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 $98,300, a midpoint of $115,700, and a maximum salary of $133,100, 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!

Where you can expect to work:

Our product provides entrepreneurs the flexibility of working in their office or the field and we offer that same opportunity to our employees. You will have the choice to work in either our Edmonton or Toronto offices or remotely anywhere within Canada. We’re committed to ensuring the best experience for all Jobberinos to do impactful work. 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!

Apply now >