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Senior Director, Product Management

Job in California, St. Mary's County, Maryland, 20619, USA
Listing for: Octopusapp Inc.
Full Time position
Listed on 2026-01-12
Job specializations:
  • Business
  • IT/Tech
Salary/Wage Range or Industry Benchmark: 150000 - 200000 USD Yearly USD 150000.00 200000.00 YEAR
Job Description & How to Apply Below

Are you ready to shape the future of how home service businesses get discovered, build their reputation, and win more work? Jobber is looking for a Director of Product, Win Work to lead our marketing and sales tools portfolio and drive meaningful commercial impact for small businesses.

About Jobber

Jobber is the leading platform for home services, helping businesses that keep our homes and communities running. We work with home service providers — from landscapers and cleaners to contractors and specialty trades — to transform the way work is delivered through technology. With Jobber, they can quote, schedule, invoice, communicate with customers, and get paid, all while offering a smooth, professional experience.

Running a small business today is complex. Customer expectations are rising, technology is evolving rapidly, and owners need tools that work the way they do. That’s why we give them the power and flexibility to run their business 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, Deloitte’s Technology Fast 50™, and more. With over a decade of building for home service businesses, we’ve come a long way — but we’re just getting started.

This is a remote-first role open to candidates in Canada or the the following United States:
California, Colorado, Georgia, Maryland, Massachusetts, Minnesota, New Jersey, New York, Texas, Utah

The Team

The Win Work group builds the tools that help small businesses attract, engage, and convert customers — from online presence and reputation to marketing campaigns and lead management. These products represent a fast-growing and increasingly strategic part of Jobber’s business, combining mature offerings with emerging AI-driven opportunities.

The Role

Reporting to the SVP of Product, you will define and execute the vision for Jobber’s Marketing and Sales product portfolio. You’ll lead a team of Product Managers responsible for a multi-product portfolio with significant revenue, retention, and monetization impact.

You’ll bring commercial rigor, strong product intuition, and deep customer empathy — and you’ll work across Jobber to ensure our products deliver measurable value for service providers and meaningful growth for Jobber.

Key Responsibilities

Strategic Leadership

Develop and execute a bold, multi-year strategy for Jobber’s marketing and sales tools portfolio.

Balance investment across improvements to mature products, expansion into new segments, and major 0→1 opportunities.

Conduct broad and deep customer discovery to understand how service providers attract and win jobs, and convert that insight into strategy and product direction.

Collaboration & Cross-Functional Leadership

Partner closely with Engineering, Design, Analytics, Marketing, Sales, and Customer Success to identify gaps, shape product capabilities, and bring offerings to market.

Work with product marketing and GTM partners to drive adoption, attach, and overall commercial performance.

Communicate product vision, decisions, and results clearly to leadership and cross-functional stakeholders.

Champion the voice of the customer and define workflows that help service providers get noticed online, earn trust, and convert leads more effectively.

Establish strong feedback loops to iterate quickly and deliver high-quality, intuitive product experiences.

Integrate AI meaningfully into customer-facing experiences, helping service providers market and sell with greater efficiency and consistency.

Commercial Impact

Deliver measurable business impact by scaling adoption, engagement, and retention across the portfolio.

Influence pricing, packaging, and value communication to ensure clear ROI for customers and revenue growth for Jobber.

Maintain a balanced portfolio that supports short-term goals while building long-term foundations.

Performance & Measurement

Define KPIs for the Win Work portfolio and hold teams accountable to outcomes.

Use data and qualitative insight to evaluate product health, make tradeoffs, and prioritize improvements.

Continually refine functionality based on…

Position Requirements
10+ Years work experience
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