Principal Revenue Operations Manager

Octopusapp Inc.; Canada; Hybrid; CAD 210,000 - 284,000; Full time

Benefits offered by this job

Equity rewards

Health benefits

Retirement matching

Stock options

Job summary

Jobber seeks a Principal Revenue Operations Manager to lead GTM strategy, tooling, and experimentation. You will drive top-of-funnel initiatives, AI-driven optimization, and scale RevOps across Marketing, Sales, and Customer Success.

You will collaborate with executive leadership to align data, processes, and technology with growth objectives and customer journeys.

Qualifications

• Expert in Revenue Operations or GTM craft operations across Sales, Marketing, and RevOps.

Responsibilities

• Lead strategic GTM initiatives, pipeline planning, and organizational scaling.

Skills

Revenue Operations

Lead generation

B2B SaaS GTM

Salesforce

HubSpot

APIs & webhooks

AI tools in GTM

Tableau

SQL

Communication & collaboration

Experimentation & analytics

Quota ownership

Clay

n8n

REGAL/Retell/CrewAI/Vapi

Tools

Clay

n8n

Job description

Do you want to impact the hardest working people in the world?

Then Jobber might be the place for you! We’re looking for a Principal Revenue Operations Manager to be part of our Marketing 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:

Revenue Operations unifies people, processes, technology, and data into a high-performance GTM engine. We’re strategists, operators, and technologists who turn insights into action. Our mission is to create a buyer-centric revenue journey through scalable systems, innovative experimentation, and end-to-end operational excellence.

The role:

Jobber is looking for a Principal Revenue Operations Manager— a rare blend of strategist, builder, and innovator to join our team. This role is ideal for someone who thrives at the intersection of go-to-market (GTM) strategy, advanced tooling, and experimental growth engineering. You’ll lead critical initiatives that drive revenue growth, scale our GTM systems, and deploy bleeding-edge AI and automation tactics across our pipeline.

You’ll work closely with leaders across Marketing, Sales, and Customer Success, influencing how Jobber attracts, engages, and converts prospects—while building replicable systems that future‑proof our growth. This role specifically will start focused on our top‑of‑funnel and AI portfolios.

As the Principal Revenue Operations Manager you’ll do :

Strategic Leadership

Lead mission-critical initiatives that shape GTM structure, sales execution, segmentation, and organizational scaling.

Identify large impact initiatives that would materially impact our top of funnel, manage a pilot to prove out the impact, and work with partnering teams to scale

Partner with GTM leadership on strategic planning for pipeline coverage, channel strategy, capacity, and forecasting.

Act as a senior mentor within RevOps, guiding junior team members while championing innovation and experimentation.

Serve as a primary liaison between go-to-market teams and technical stakeholders to align priorities and execute roadmaps.

Own relationships with data vendors and data strategy

Architect, test, and scale top‑of‑funnel and outbound lead generation experiments using modern AI/automation tools (e.g., ChatGPT, Clay, Supabase, and n8n).

Embed experimentation in the sales development lifecycle—running A/B tests, refining ICP outreach, and establishing scalable demand capture tactics.

Regularly engage directly with customers or prospects to validate hypotheses, improve conversion systems, and optimize customer journey handoffs.

Technical Systems & Enablement

Own components of our GTM systems strategy: marketing automation, outbound enablement, enrichment, reporting, etc.

Lead the technical transformation of our revenue tech stack, including API integration, low-code automation (e.g., n8n), and AI augmentation.

Translate evolving GTM needs into system changes—from solution design through implementation and enablement.

Own, operate, and iterate on production outbound and lifecycle automation — including monitoring, debugging, and improving live n8n workflows and scoring pipelines.

To be successful, you should have:

• Expert-level knowledge in Revenue Operations or GTM craft operations (Sales Ops, Marketing Ops, or GTM Engineering).
• Strong background in lead generation or a customer-facing sales role (e.g., SDR, AE, Growth Hacker).
• Deep understanding of B2B SaaS GTM strategy across sales, marketing, and customer lifecycle.
• Practical experience in tools like Clay & n8n
• Awareness of cold campaign compliance and technical limitations, including scaling campaigns and regulatory compliance
• Expert in Salesforce and HubSpot; strong proficiency in webhooks, APIs, and automation frameworks.
• Experience using or deploying AI tools across GTM workflows (e.g., for content generation, outreach, or decision‑making).
• Skilled in data visualization tools like Tableau.
• Excellent communicator with a bias toward action, systems thinking, and rapid iteration.
• Strong knowledge of SQL database language.

Bonus Experience

• Direct experience using tools like REGAL, Retell, CrewAI, Vapi.
• Prior ownership of experimental initiatives with defined metrics and agile delivery cycles.
• Experience carrying a lead or revenue quota.

What You Can Expect

• A high-impact, high‑autonomy role with visibility across the executive team.
• A front‑row seat to shaping how AI and automation redefines RevOps and GTM strategy.
• A strong, supportive culture rooted in humility, impact, and giving a sh*t.

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!

Location:

We believe great collaboration is intentional, and sometimes that means coming together in person to build, brainstorm, and connect. To support this, the role is open to candidates based in one of our hub cities: Edmonton, Toronto, Vancouver, or Kitchener‑Waterloo.

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!