Director, Software Engineering (AI Workflows & Ecosystem)
Are you driven to bring people, technology, and strategy together to build impactful software?
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!
THE PROBLEM YOU’D OWN
Jobber has AI in production, but not yet at its full potential.
We already have AI answering calls, drafting responses, and powering parts of our product. But today, those systems are still fragmented. Some teams are ahead. Others aren’t. Some workflows are intelligent. Others are still manual. And most importantly, the system doesn’t yet think across the product.
A service pro still has to:
Manually follow up on jobs
Piece together context across workflows
Decide what to do next
The platform doesn’t proactively help them run their business. That’s the gap.
The opportunity is to evolve Jobber from: AI-powered features → AI-powered workflows → AI-powered business operations
This role owns that shift. Not a team. Not a feature. The system.
THE CUSTOMER
You’re building for people who don’t have time to think about software.
A plumber finishing their last job at 6 pm
A cleaner managing 30 clients and 5 employees
A landscaper juggling scheduling, payments, and follow-ups
They’re not asking for “AI.” They’re asking:
“What should I do next?”
“Why didn’t this job convert?”
“Who should I follow up with today?”
And eventually:
They shouldn’t have to ask at all.
The Director who succeeds here will understand:
This isn’t about building clever systems; it’s about building systems that remove thinking from already overwhelmed people.
WHAT YOU’D OWN
End-to-end ownership of Jobber’s AI system layer. You’re not owning a single team. You’re owning how intelligence flows across the entire product.
Product + Platform Scope
AI Foundations (models, orchestration, evals, guardrails)
Copilot (user-facing intelligence layer)
Automations (workflow execution layer)
Platform Experience / Marketplace (integration + ecosystem surface)
Emerging surfaces (voice, messaging, cross-product intelligence)
What this actually means
You are responsible for:
How decisions get made inside the system
How context moves across workflows
How actions get triggered (and when they shouldn’t)
How we evaluate whether AI is actually working
This includes:
Agentic workflows (reason → decide → act → evaluate)
Cross-product context (jobs, customers, payments, communication)
Reliability, safety, and failure modes
Developer experience for building on top of AI systems
Team Structure
~30 engineers across 4–6 teams
4–6 EMs / Sr EMs reporting into you
Close partnership with Product, Design, Data
WHAT “GOOD” LOOKS LIKE
Not “we shipped AI features.”
Instead:
The system proactively recommends and takes actions
Teams build on shared AI primitives, not reinventing them
AI output is reliable, measurable, and improving over time
Engineers trust the system, and move faster because of it
Customers feel like the product is working for them, not just responding
THE AI BAR (THIS ROLE IS DIFFERENT)
We are not looking for:
Someone who rolled out Copilot internally
Someone who used LLM APIs for features
Someone adjacent to AI
We are looking for someone who has:
Built real systems where AI makes decisions and takes actions in production.
That means experience with:
Agent orchestration (not just prompts)
Tool use and workflow execution
Evaluation (offline + online)
Observability and failure handling
Guardrails and safety in real systems
Tradeoffs between autonomy vs. control
You don’t need to code daily, but you must be able to reason at the system level.
WHAT YOU’LL ACTUALLY DO
Define how AI should work across Jobber, not just within a team
Build and evolve a multi-team org to execute on that vision
Make tradeoffs between speed, quality, and safety
Push teams beyond feature thinking into system thinking
Challenge assumptions, including leadership’s
Drive adoption across engineering, product, and the company
WHAT WE’RE LOOKING FOR
Leadership
You’ve led orgs through complexity, not just growth.
Managed managers across multiple teams
Built organizations that scale (not just teams that ship)
Driven cross-org alignment in ambiguous spaces
Product + Systems Thinking
You think in systems, not features.
You understand how user workflows connect end-to-end
You’ve partnered deeply with Product and Design
You care about customer outcomes, not just technical output
AI Depth (non-negotiable)
You’ve built or led production LLM/agentic systems.
You understand what actually works (and what doesn’t)
You’ve seen systems fail and improved them
You have opinions about evaluation, reliability, and safety
Execution
You can move fast without breaking everything.
You’ve balanced shipping vs infrastructure vs tech debt
You know when to iterate and when to redesign
WHY JOBBER · WHY NOW?
This is not “AI theatre.”
We already have:
AI Receptionist (live, handling real customer calls)
AI features embedded across the product
250,000+ businesses using the platform
What we don’t have yet is: A unified, intelligent system across the product.
That’s what this role builds.
TLDR:
Most Director roles optimize delivery. This one defines: How an entire product becomes intelligent.
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, matching in RRSP, TFSA or FHSA, 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.
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!
Fintech Operations Lead
Does standing up operations for brand new financial services excite you?
Then Jobber might be the place for you! We're looking for a Fintech Operations Lead to be part of our Fintech Operations team.
About Jobber:
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 .
The Team:
We’re building the financial backbone for field service businesses. Our Fintech team is one of the most strategically important and fastest growing parts of Jobber. We help businesses get paid, access capital, understand their financial health, and ultimately stay in business longer.
The future of financial services is embedded, and we’re still early. Small businesses increasingly rely on vertical SaaS platforms like Jobber not just to run their operations, but to manage their money.
You'll report to the Senior Director of Fintech Risk & Operations and work as a peer to our Senior Fintech Operations Manager, collaborating closely with senior leadership including the VP of Fintech and the Senior Director, Fintech New Bets. Flexibility and the ability to thrive in ambiguity are key—the fintech space is constantly changing, and we're looking for someone who can lead through that change while keeping a team grounded and high-performing.
The Role:
Jobber is looking for a dynamic and experienced Fintech Operations Lead to own two critical pillars of our fintech business: bookkeeping operations and capital operations. This role is central to how Jobber scales its fintech business responsibly, and the person who takes it on will shape not just the processes but help build the business.
This is a rare opportunity to build from the ground up in a high-growth fintech environment. We're looking for a self-starter who sets the standard through their own work, cultivates relationships, and is genuinely energized by turning complex operational problems into clean, repeatable systems. You have a bias toward action, data, and automation; you're comfortable with AI tools; and you know how to run multiple workstreams without anything slipping through the cracks. You work well cross-functionally.
The Fintech Operations Lead will own:
Bookkeeping Operations: Build and lead the operational foundation for Jobber's bookkeeping product. This means standing up the function from scratch, one that supports Jobber customers day-to-day through customer support, issue escalation, and vendor support, while also designing the processes and systems that allow the operation to scale. You won't just be running this function; you'll be influential in shaping its strategy and direction, working closely with Product and leadership to define what great looks like for this part of the business.
Capital Operations: Run the operational backbone of Jobber's lending products. This covers the end-to-end lifecycle of merchant loan activity. As the product grows, you'll ensure the operational infrastructure scales with it. This requires working closely with our lending partners and their compliance and regulatory teams.
Data, Reporting and AI-Assisted Operations: Build and own the reporting that gives leadership real-time visibility into capital performance, and bookkeeping health. You're comfortable working with data directly, writing queries, interpreting results, and surfacing what matters. You actively use AI tools to cut down on manual work and improve output quality, and you build that same orientation into your team's day-to-day.
Policy and Process Development: Design and document the policies, controls, and standard operating procedures that underpin your areas of ownership. You see process documentation as a strategic asset, something that reduces key-person risk, enables scale, and holds up to regulatory scrutiny. You build things that outlast any single person.
Cross-Functional Partnership: Partner closely with Support, Legal, Finance, Product, Analytics and Engineering to ensure compliance and operational requirements get embedded early, not as an afterthought. You communicate clearly across functions and can translate complex regulatory or operational constraints into practical guidance for people who don't live in your world.
To be successful, you should have:
Strong working knowledge of compliance operations including KYC/KYB, AML/ATF, and PCI DSS, ideally across both Canada and the US.
Hands-on experience with bookkeeping or financial operations, including reconciliation and close collaboration with Finance to ensure ledger accuracy.
Familiarity with lending or capital products and how loan disbursement, repayment, and delinquency workflows operate in practice.
A data-first mindset with practical SQL/Python or analytics skills and comfort building and interpreting operational dashboards.
Familiarity with credit risk management, and comfort with concepts such as credit exposure, probability of default, and loss given default.
A genuine track record of using AI tools to improve output and operational efficiency, and enthusiasm for pushing this further.
Demonstrated ability to build policy, process, and controls from scratch in a fast-moving environment.
Strong project management skills with the ability to manage multiple workstreams simultaneously.
Familiarity with operational tooling such as Jira, Asana, Salesforce etc.
A willingness to grow into people leadership as the business scales.
Bachelor's degree in a relevant field (Business, Finance, or similar) is required. Advanced certifications or degrees add bonus points.
Location:
This role can be fully remote from anywhere in Canada. : if your home is within commuting distance of one of our hub cities — Edmonton, Toronto, Vancouver, or Kitchener-Waterloo — you'll be expected to come into that office regularly, since in-person collaboration matters to us.
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 $121,000, a midpoint of $142,200, and a maximum salary of $163,600, 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!
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, matching in RRSP, TFSA or FHSA, 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.
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!
Director, Software Engineering (AI Workflows & Ecosystem)
Are you driven to bring people, technology, and strategy together to build impactful software?
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!
THE PROBLEM YOU’D OWN
Jobber has AI in production, but not yet at its full potential.
We already have AI answering calls, drafting responses, and powering parts of our product. But today, those systems are still fragmented. Some teams are ahead. Others aren’t. Some workflows are intelligent. Others are still manual. And most importantly, the system doesn’t yet think across the product.
A service pro still has to:
Manually follow up on jobs
Piece together context across workflows
Decide what to do next
The platform doesn’t proactively help them run their business. That’s the gap.
The opportunity is to evolve Jobber from: AI-powered features → AI-powered workflows → AI-powered business operations
This role owns that shift. Not a team. Not a feature. The system.
THE CUSTOMER
You’re building for people who don’t have time to think about software.
A plumber finishing their last job at 6 pm
A cleaner managing 30 clients and 5 employees
A landscaper juggling scheduling, payments, and follow-ups
They’re not asking for “AI.” They’re asking:
“What should I do next?”
“Why didn’t this job convert?”
“Who should I follow up with today?”
And eventually:
They shouldn’t have to ask at all.
The Director who succeeds here will understand:
This isn’t about building clever systems; it’s about building systems that remove thinking from already overwhelmed people.
WHAT YOU’D OWN
End-to-end ownership of Jobber’s AI system layer. You’re not owning a single team. You’re owning how intelligence flows across the entire product.
Product + Platform Scope
AI Foundations (models, orchestration, evals, guardrails)
Copilot (user-facing intelligence layer)
Automations (workflow execution layer)
Platform Experience / Marketplace (integration + ecosystem surface)
Emerging surfaces (voice, messaging, cross-product intelligence)
What this actually means
You are responsible for:
How decisions get made inside the system
How context moves across workflows
How actions get triggered (and when they shouldn’t)
How we evaluate whether AI is actually working
This includes:
Agentic workflows (reason → decide → act → evaluate)
Cross-product context (jobs, customers, payments, communication)
Reliability, safety, and failure modes
Developer experience for building on top of AI systems
Team Structure
~30 engineers across 4–6 teams
4–6 EMs / Sr EMs reporting into you
Close partnership with Product, Design, Data
WHAT “GOOD” LOOKS LIKE
Not “we shipped AI features.”
Instead:
The system proactively recommends and takes actions
Teams build on shared AI primitives, not reinventing them
AI output is reliable, measurable, and improving over time
Engineers trust the system, and move faster because of it
-
Customers feel like the product is working for them, not just responding
THE AI BAR (THIS ROLE IS DIFFERENT)
We are not looking for:
Someone who rolled out Copilot internally
Someone who used LLM APIs for features
Someone adjacent to AI
We are looking for someone who has:
Built real systems where AI makes decisions and takes actions in production.
That means experience with:
Agent orchestration (not just prompts)
Tool use and workflow execution
Evaluation (offline + online)
Observability and failure handling
Guardrails and safety in real systems
Tradeoffs between autonomy vs. control
You don’t need to code daily, but you must be able to reason at the system level.
WHAT YOU’LL ACTUALLY DO
Define how AI should work across Jobber, not just within a team
Build and evolve a multi-team org to execute on that vision
Make tradeoffs between speed, quality, and safety
Push teams beyond feature thinking into system thinking
Challenge assumptions, including leadership’s
Drive adoption across engineering, product, and the company
WHAT WE’RE LOOKING FOR
Leadership
You’ve led orgs through complexity, not just growth.
Managed managers across multiple teams
Built organizations that scale (not just teams that ship)
Driven cross-org alignment in ambiguous spaces
Product + Systems Thinking
You think in systems, not features.
You understand how user workflows connect end-to-end
You’ve partnered deeply with Product and Design
You care about customer outcomes, not just technical output
AI Depth (non-negotiable)
You’ve built or led production LLM/agentic systems.
You understand what actually works (and what doesn’t)
You’ve seen systems fail and improved them
You have opinions about evaluation, reliability, and safety
Execution
You can move fast without breaking everything.
You’ve balanced shipping vs infrastructure vs tech debt
You know when to iterate and when to redesign
WHY JOBBER · WHY NOW?
This is not “AI theatre.”
We already have:
AI Receptionist (live, handling real customer calls)
AI features embedded across the product
250,000+ businesses using the platform
What we don’t have yet is: A unified, intelligent system across the product.
That’s what this role builds.
TLDR:
Most Director roles optimize delivery. This one defines: How an entire product becomes intelligent.
Compensation:
At Jobber, we also believe that compensation should be transparent, fair, and supportive of your experience and growth. This role has a minimum annual salary of $221,800 CAD, a midpoint of $261,000 CAD, and a maximum salary of $300,100 CAD, designed to reflect the progression from learning the ropes to truly excelling.
We design our compensation to reflect each new hire’s skills, experience, and 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.
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!
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, matching in RRSP, TFSA or FHSA, 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.
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!
The full posting opens here — pay, setting and the full description, without leaving the list.