Senior Manager, Sales Planning & Operations

Jobber•Toronto, ON

29d•CA$151,200 - CA$204,500•Onsite

About The Position

Ready to build the planning engine that powers our next stage of growth? Then Jobber might be the place for you! We’re looking for a Senior Manager, Sales Planning & Operations to be part of our Sales 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. Reporting to the Senior Director, Sales Enablement & Operations, the Senior Manager, Sales Planning & Operations will own the end-to-end sales planning function for a scaling B2B SaaS company serving the home services market. This is a builder role with an eye to the numbers, with a growing leadership mandate. You'll partner at the senior levels across Finance/FP&A, Sales Leadership, Strategy & Operations, and Marketing to build the analytical infrastructure that connects strategic direction to field execution. The mandate isn’t just setting the goals though, it’s to make sure the execution is on track and results are shared broadly. This isn't a "run the model someone else built" job. You're building the model, building the team around it, and building the translation layer that turns targets into field-ready plans and field reality back into decisions leadership can act on.

Requirements

Extensive experience in FP&A, revenue operations, or sales operations with direct ownership of quota modelling, capacity planning, or sales planning, ideally with some exposure to managing or mentoring junior talent
Proven ability to build planning models from scratch in a high-growth SaaS environment, not just maintain inherited ones
Strong analytical foundation: fluent in Excel/Google Sheets for modelling; SQL or BI tool exposure (Looker, Tableau, etc.) is a plus
Ability to leverage AI into workflows. Jobber is an AI first organization and this role will need to leverage and include AI to be effective and efficient
Comfort operating in ambiguity. You won't be handed a process; you'll design it
Track record of influencing director+ stakeholders with data, including stakeholders outside your own function, not just producing outputs they ignore
Strong communication skills as a core requirement, not a soft nice-to-have: demonstrated ability to translate rep-level math into exec-level clarity, and to explain how a target set at the top actually plays out on the ground — in both directions

Nice To Haves

Builder mindset — gets more excited by a blank slate than a polished system
High ownership — treats the number like it's their own
Cross-functional instinct — naturally connects Sales, Finance, and Ops rather than staying in a lane
Precision without perfectionism — knows the difference between a model that's good enough to act on and one that needs another week
Clear communicator — can hold their own in a room with directors and VPs who challenge the model's assumptions, not just present to them
People-leader potential — wants to build and grow a team, not just an individual body of work

Responsibilities

Bottom-up sales planning. Rep-level quota models, channel-level capacity plans, and segment-level rollups that stress-test top-down targets from below.
Forecasting infrastructure. Design and run the operating rhythm for how SE&Ops inputs into the forecast: by channel, by initiative, and by segment, including the intersections across them. Outputs include headcount planning and quota setting.
Quota and capacity design. Own the analytical work behind quota-setting and compensation plan design. Work with Finance to validate assumptions from the top; work with Sales leadership to ground-truth the outputs.
Goal-setting translation. Own the two-way translation between company-level targets and field-level goals: how a top-down revenue or growth target decomposes into segment/channel/rep targets, and how performance against those targets rolls back up into a coherent read-out for Sales, Finance, and executive stakeholders. This is a distinct deliverable, and requires being equally fluent in the math and in telling the story to a director or VP who wasn't in the room when the model was built.
Planning cadence. Stand up the Q4 planning process as the first end-to-end cycle. Establish the repeatable model for how SE&Ops anchors into annual and quarterly planning going forward.
Team build. Hire and manage a Planning Analyst within Year 1 as the function's first direct report, with the expectation that this team grows further as scope expands.