Director, Software Engineering (AI Workflows & Ecosystem)
$221.8k per yearDevconnectplatform
- Director, Software Engineering (AI Workflows & Ecosystem)Jobber222k–300k CADFull-timeremote· leadCanadallmListed via Jobicy · posted 17 Oct 2026. The application happens there, not on DevConnect.Apply on Jobicy## DescriptionAre 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 OWNJobber 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 nextThe 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 operationsThis role owns that shift. Not a team. Not a feature. The system.THE CUSTOMERYou’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-upsThey’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 OWNEnd-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 meansYou 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 workingThis 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 systemsTeam Structure-~30 engineers across 4–6 teams-4–6 EMs / Sr EMs reporting into you-Close partnership with Product, Design, DataWHAT “GOOD” LOOKS LIKENot “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 respondingTHE 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 AIWe 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. controlYou 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 companyWHAT WE’RE LOOKING FORLeadershipYou’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 spacesProduct + Systems ThinkingYou 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 outputAI 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 safetyExecutionYou can move fast without breaking everything.-You’ve balanced shipping vs infrastructure vs tech debt-You know when to iterate and when to redesignWHY 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 platformWhat 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 applica
- J-18808-Ljbffr
Vacancy posted 3 days ago
Similar jobs that could be interesting for youBased on the Director, Software Engineering (AI Workflows & Ecosystem) in Canada vacancy
$221.8k per year
...strategy together to build impactful software? Jobber exists to help... ...YOU’D OWN Jobber has AI in production, but not yet at... ...are ahead. Others aren’t. Some workflows are intelligent. Others are still... ...have to ask at all. The Director who succeeds here will understand...SuggestedLong term contractInternshipWork at officeLocal areaShift work- ...GitLab to ship better, more secure software faster. The same principles... ...our team works: we embrace AI as a core productivity... ...incorporate AI into their daily workflows to drive efficiency, innovation... ...Role We are looking for a Director of Engineering to lead the teams...SuggestedFull timeInternshipRemote work
Gitlab
Canadamore than 2 months ago - ...Elastic, the Search AI Company, enables everyone to find the answers they need in... ...What is The Role The Security EDR Workflows team is in charge of building core capabilities... ...our security product. As a Senior Software Engineer on the Security EDR Workflows team, you...SuggestedFull time
Elastic Nv
Canadaa month ago - ...About Haven Safety: Haven Safety AI is building the enterprise learning intelligence... ...AI agents examines evidence, controls, engineering factors, procedures, regulations, training... ...that real users depend on. Agentic workflows. Hands-on experience building and debugging...SuggestedFull timeInternship
Ai Fund
Canada21 days ago $95k per year
...cutting-edge cloud platform, coupled with AI-driven analytics tools, unlocks the true... ...a highly skilled and experienced Senior Software Engineer, AI to perform a key role in our digital... ...actions safely within defined business workflows. Calabrio-Verint has embarked journey...SuggestedFull timeFlexible hoursCalabrio, Inc.
Canadaa month ago- ...Flosum , we are building the world's best software for the modern enterprise. Our team is... ...our customers and set a new bar for engineering excellence. We combine deep expertise in... .... About the Role We are hiring a Director of Software Development to lead a team...Full timeWork from home
Flosum
Canadamore than 2 months ago - ...help people make smarter financial decisions. As a Security Software Engineer focused on AI and Automation, you'll help strengthen the security,... ...platforms to embed security guidance into everyday engineering workflows Developing REST APIs and platform services with...Full timeLocal areaRemote workWork from home
NerdWallet
Canadamore than 2 months ago $135k - $150k per year
...scaling our platform and expanding our AI capabilities, we're looking for experienced engineers who thrive in fast-moving environments, embrace AI-first software development, and take ownership... ...AI-powered applications and agentic workflows. This is a senior individual...Full timeFable
Canadamore than 2 months ago$160.32k - $200.4k per year
...work We use Artificial Intelligence (AI) to help make our hiring process efficient... ...Join the team as Twilio’s next Staff Software Engineer. About the job The Compliance Experiences... ...You will embrace AI-driven development workflows, using LLMs and agentic tools to...Remote jobLong term contractFull timeLocal areaWorldwideTwilio
Canada5 days ago$110k - $145k per year
...A little bit about our team Sureel AI is building the standards and infrastructure... ...role We are looking for a senior software engineer with deep experience in backend,... ...operations, integrations, and configurable workflows. Make architecture decisions across databases...Full timeWarner Music Group Corp.
Canada11 days ago$327.6k per year
...building the tools that define how software gets built and delivered. As AI agents redefine software development... ...that make autonomous workflows trustworthy by default. ___________... ...seeking an inspiring and experienced Director of Partner Solution Engineering to...Remote jobLong term contractFull timeWork from homeHome officeShift workDocker
Canada6 days ago- ...Fellow is the AI meeting assistant that helps teams turn conversations into decisions... ...mind. We are looking for a full-stack Software Engineer to join our Engineering team and help... ...should be excited to push beyond default workflows, experiment with new ways of building software...Remote jobFull timeWork at office
Fellow Insights Inc
Canada4 days ago - ...warehousing, observability, and AI workloads. The company’s... ...About the team The AI/ML Engineering team builds and operates ClickHouse... ...skilled and experienced software engineers to join us, who will... ...external/internal AI services. Ecosystem Integrations: Implement and...Full timeLocal areaRemote workHome officeFlexible hours
Clickhouse
Canadamore than 2 months ago - ...hiring a Senior Partner Marketing Manager, AI & ISV Ecosystem to help define how Dropbox shows up in... .... AI is already embedded in this workflow. You will use approved AI tools to accelerate... .... Create an evergreen co-marketing engine: Build repeatable programs that extend...Full time
Dropbox
Canadaa month ago - ...platform combines the best of AI and human intelligence to help... ...time actions within the CCaaS ecosystem Seamlessly hand off conversations... ...losing context, history, or workflow state Support human agents... ...looking for strong backend engineers who want to work at the intersection...Full timeWork at officeLocal areaRemote workWork from homeHome office
Cresta
Canadamore than 2 months ago - ...Job description Director of AI Content Systems, Marketing Remote (United States or Canada... ...the AI-powered system (think content engineering) that turns product, customer, and expert... ...organic pipeline. You're not a software engineer, but you think like one. You're...Remote jobFull timeFor contractorsFreelanceWorldwideFlexible hours
Time Doctor
Canada4 days ago - ..., grow a world-class platform engineering team in Vancouver, and directly... ..., opinionated use of LLMs and AI-assisted development tools... ...tools into daily engineering workflows (design exploration, implementation... ...Need to Have ~12+ years of software engineering experience, including...Full timeWork at officeLocal areaWorldwide
Redis
Canadaa month ago - ...across the entire public safety ecosystem — dispatch, law enforcement,... ...evidence, there's a good chance our software is working behind the scenes.... ...for over four decades. AI is central to where we're... ...intelligence directly into the workflows our customers rely on every day...Full timeInternshipRemote workWork from home
Versaterm
Canada24 days ago $90 - $98 per hour
...visionary and hands-on Technical Director to join our Cloud & DevOps... ...modernize their platforms, accelerate software delivery, and unlock value... ...cloud-native technologies and AI-powered solutions. The... ...shape technical strategy, mentor engineering teams, and partner with...Hourly payFull timeTemporary workValtech Se
Canada13 days ago- ...re part of the Valsoft Edelweiss Software Group — a large-scale portfolio... ...We're looking for true builders: engineers who orchestrate systems, ship production-grade AI, and modernize massive legacy... ...Develop autonomous multi-agent workflows using parallel orchestration tools...Full timeInternshipShift work
Valsoft
Canadaa month ago - ...platform combines the best of AI and human intelligence to help... ...execution frameworks that let engineers iterate quickly and ship with... ...looking for ~5+ years of software engineering experience, with meaningful... ...ownership. ~ AI-native workflow — you actively use LLMs and...Full timeWork at officeLocal areaRemote workWork from homeHome office
Cresta
Canadamore than 2 months ago $171.5k - $201k per year
...specified location above. We are AI Native We are building an... ...a product-minded, AI-Native engineering team. That means AI isn’t just... .... We’ve redesigned our team workflows around AI, treating it as a... ...hiring a backend AI-Native Senior Software Engineer II — a senior...Full timeSummer workInternshipRemote workFlexible hoursLife360
Canadamore than 2 months ago$196k - $207k per year
...together. We’re looking for an Engineering Manager to lead our Catalog... ...team. This team builds the AI-native platform and pipelines... ...models, classical inference, workflow orchestration, and human review... ...measurable impact across Instacart’s ecosystem. About the Job This is...Permanent employmentFull timeWork at officeRemote workWork from homeFlexible hoursInstacart
Canadamore than 2 months ago- ...YOUR ROLE & MISSION As a Senior Software Engineer, you will be a critical part of our growing... ...the infrastructure that powers Apollo’s AI-driven internal products. On the data side... ...Apollo reliably linked to the broader ecosystem at high throughput. You enjoy working...Full timeWorldwide
Apollo.Io
Canadamore than 2 months ago $132k - $181.7k per year
...intelligence and search built on proven AI, AlphaSense delivers insights... ...is seeking an exceptional engineer to own our Excel plugin... ...intelligence directly into the workflow of financial professionals worldwide... ...~5+ years building production software, with significant experience...InternshipWork at officeLocal areaWorldwideAlphasense
Canada18 days ago- ...we are. About the role As our Engineering Director for Core Experience , you’ll lead the... ...while giving internal teams the tools and workflows needed to support the member experience... ...com is actively evolving how we build software as AI becomes a core part of the...Long term contractFull timeRemote workFlexible hours
Supercom
Canadamore than 2 months ago - ...experimentation, and emerging AI capabilities that make collaboration... ...re a cross-functional team of engineers, product managers, designers,... ...YOUR MISSION As a Senior Software Engineer on the Growth &... ...MCP) and the broader AI tooling ecosystem and the ability to quickly learn...Long term contractFull time
Mural
Canada24 days ago - ...About CircleCI Engineering CI/CD has been solved. Now it's being reinvented. AI agents don't just run pipelines. They write... ...biggest advantages in an agentic software delivery lifecycle. Flaky test... ...from event streams and durable workflows built on Temporal. Data should...Full timeImmediate start
Circleci
Canada3 days ago - ...Spellbook is the most comprehensive AI copilot for transactional... ...Spellbook to simplify their workflows and eliminate the drudgery of... ...have 5+ years of experience in Software Development. You have exceptional... ...development and computer engineering. You have the ability to break...Full timeContract workFlexible hours
Spellbook
Canadamore than 2 months ago - ...Safe Software is looking for an experienced developer to join our Cloud... ...technical role in our FME AI Service, AI Assist Plugin, and... ...hybrid role. We need the software engineering depth to build and operate... ...Design and build modular agentic workflows to augment the FME platform...Full timeSeasonal workImmediate startRemote workFlexible hours
Safe Software
Canada20 days ago
Do you want to receive more vacancies?
Subscribe and receive similar vacancies to Director, Software Engineering (AI Workflows & Ecosystem). Be the first to apply!
Related searches