Dropbox is a Virtual First company. For this role, we are currently only authorized to hire candidates from the following provinces: Alberta, British Columbia, Ontario, and Saskatchewan.

Role Description

Dropbox Sign is a core part of Dropbox’s suite of workflow and collaboration products, helping individuals and businesses securely prepare, send, sign, and manage agreements from anywhere. Dropbox Sign simplifies critical document workflows by enabling fast, legally binding eSignature experiences that integrate seamlessly into the tools customers already use. From sales contracts and onboarding paperwork to operational approvals and compliance workflows, Dropbox Sign helps customers move business forward with speed, security, and confidence.

As a Group Product Manager, you’ll lead and develop a team of Product Managers while driving product strategy and execution across the Dropbox Sign business. You’ll partner closely with Engineering, Design, Data Science, Marketing, Sales, Legal, and Customer Experience leaders to identify growth opportunities, improve core workflows, and deliver seamless signing and document automation experiences for customers around the world.

This role requires a strong combination of product leadership, people management, strategic thinking, and operational excellence. You’ll be responsible for growing and mentoring a high-performing PM team, establishing strong product development practices, and driving alignment across multiple cross-functional initiatives. You’ll also have the opportunity to shape the future of digital agreements by identifying new customer needs, expanding into adjacent workflows, and scaling both the product and go-to-market capabilities needed to support long-term growth.

Responsibilities

• Lead, mentor, and develop a team of Product Managers, helping them grow in product craft, strategic thinking, execution, and cross-functional leadership.

• Define and evangelize the long-term product vision, strategy, and roadmap for Dropbox Sign. Balance investments across platform scalability, workflow automation, customer experience improvements, and new growth opportunities.

• Build a strong product culture grounded in customer empathy, data-informed decision making, accountability, and collaboration.

• Partner closely with Engineering, Design, Legal, Security, and cross-functional leaders to drive alignment, prioritize investments, and ensure high-quality execution across multiple product initiatives.

• Become an expert in our customers by leveraging research, analytics, market insights, and direct feedback to deeply understand the needs of businesses and individuals managing critical agreement workflows.

• Drive complex, multi-quarter initiatives across teams and functions, from strategy and planning through execution, launch, and iteration.

• Drive business impact by identifying key opportunities, defining success metrics, evaluating tradeoffs, and ensuring teams deliver measurable outcomes aligned to company goals.

• Establish operational rigor across the product organization, including roadmap planning, stakeholder communication, prioritization frameworks, and team processes.

• Communicate clearly and effectively with executives and cross-functional stakeholders, articulating strategy, tradeoffs, risks, and business impact.

Requirements

• 10+ years of Product Management experience, including 4+ years of people management experience leading and developing Product Managers.

• Proven track record of building and scaling high-performing PM teams in fast-paced, highly collaborative environments.

• BS/MS in Computer Science, Engineering, Business, Information Systems, Applied Math or Statistics, or relevant experience.

• Demonstrated ability to translate complex workflows into simple, intuitive, and delightful user experiences.

• Experience defining and driving multi-quarter product strategies and roadmaps that deliver meaningful business results.

• Strong analytical and problem-solving skills with the ability to connect product decisions to business outcomes.

• Excellent communication, storytelling, and stakeholder management skills; able to influence and align executives, peers, and teams across the organization.

• Proven ability to operate effectively in ambiguous environments while balancing strategic leadership with operational execution.

Preferred Qualifications

• Experience leading Product Management teams for B2B SaaS or workflow automation products.
• Experience owning and scaling eSignature, document workflow, compliance, or enterprise productivity products end-to-end.
• Strong coaching and mentoring capabilities, with a passion for developing talent and building inclusive, high-performing teams.
• Experience influencing organizational strategy and driving alignment across senior leadership.
• Strong data analytics skills, including the ability to independently analyze data and generate actionable insights to inform product direction

Compensation

Canada Pay Range

$196,300—$265,500 CAD

Company Description

Dropbox isn’t just a workplace—it’s a living lab for designing a more enlightened way of working. We’re a global community of bold visionaries and resourceful doers shaping the future of Dropbox and, in turn, the future of work. Our Virtual First model combines the autonomy of a distributed workplace with the power of human connection, creating space for meaningful work and lasting relationships. With a startup mindset and enterprise-level opportunities, we expect Dropbox employees to think critically, stay curious, and use modern tools, including AI, to improve how work gets done. Here, you can be who you are and grow into who you’re meant to be. You own your impact, helping make work more intuitive, joyful, and human for yourself and hundreds of millions of people worldwide. If you’re ready to push boundaries and challenge yourself, Dropbox is ready for you.

Team Description

Dropbox Product Managers are systems thinkers, problem solvers, and communicators who translate complex workplace challenges into intuitive, scalable solutions. Our PMs lead with insight and empathy, shaping the future of work through tools that help individuals and teams within businesses stay organized, collaborate seamlessly, and tap into the power of AI. We work across the full product lifecycle, from 0→1 vision setting to iterative evolution, partnering closely with design, engineering, research, and go-to-market teams to deliver products that millions of people trust. As part of our PM team, you’ll help shape ambitious bets that are redefining how teams work, like Dropbox Dash, a new AI-powered way to find and organize knowledge, or evolve the core Dropbox experience used by millions of users to adapt to how work gets done in the future. If you're excited by the challenge of reimagining how the world works from first principles and scaling delightful, high-impact products, we’d love to meet you.

Virtual First

Dropbox’s Virtual First way of working is designed to help people do their best work with flexibility, autonomy, and connection. Day to day, teams work remotely with nonlinear schedules and core collaboration hours that support deep focus and individual working styles. We prioritize asynchronous communication to improve clarity, respect deep work time, and reduce unnecessary meetings. While remote work is the primary experience for our employees, we also prioritize intentional, in-person connection. We bring teams together through regular team gatherings, on-demand workspaces, and Dropbox Neighborhood events in order to strengthen team cohesion, foster creativity, and enhance momentum. Virtual First is built to provide the same access to opportunity, growth, and impact for everyone, regardless of location.

This role requires travel to offsites and various other team gatherings (approximately 5-10% of the year or 2-3 days per quarter). We provide advance notice when possible and encourage candidates to discuss any accommodation needs during the interview process.

Dropbox supports responsible use of AI for preparation, but misrepresentation of skills or experience is not permitted. See our AI Principles.

Dropbox is an equal opportunity employer. We are a welcoming place for everyone, and we do our best to make sure all people feel supported and connected at work.