Senior Group Product Manager, Dropbox Sign

This position is posted by Jobgether on behalf of a partner company. We are currently looking for a Senior Group Product Manager, Dropbox Sign in Canada.

This is a senior product leadership role responsible for shaping the strategy, execution, and evolution of a leading digital agreement and eSignature platform used by individuals and businesses worldwide. You will lead a team of Product Managers while driving cross-functional alignment across Engineering, Design, Data, Marketing, Sales, Legal, and Customer Experience. The role blends strategic vision with hands-on execution, requiring you to define product direction, prioritize high-impact initiatives, and ensure delivery of seamless, secure, and scalable document workflow experiences. You will play a critical role in expanding core capabilities, improving customer journeys, and identifying new growth opportunities across adjacent workflow areas. This is a highly influential position where you will help shape the future of digital agreements while building and mentoring a high-performing product organization in a fast-paced, data-driven environment.

• Lead, coach, and develop a team of Product Managers, supporting their growth in product craft, strategic thinking, execution, and cross-functional leadership.
• Define and drive the long-term product vision, strategy, and roadmap for a digital signature and workflow platform, balancing platform scalability, customer experience, and growth initiatives.
• Build and reinforce a strong product culture rooted in customer empathy, data-driven decision-making, accountability, and cross-functional collaboration.
• Partner closely with Engineering, Design, Legal, Security, and other stakeholders to align priorities and ensure high-quality execution across multiple product streams.
• Own and drive multi-quarter strategic initiatives from discovery through execution, launch, and iteration, ensuring measurable business impact.
• Leverage customer insights, analytics, and market research to deeply understand user needs and translate them into product opportunities.
• Establish strong operational rigor across product planning, prioritization frameworks, roadmap management, and stakeholder communication.
• Define success metrics, evaluate trade-offs, and ensure alignment between product execution and broader business objectives.
• Communicate product strategy, progress, and risks clearly to executive stakeholders and cross-functional leadership teams.
• Identify new growth opportunities across adjacent workflows and expand product capabilities to support long-term scalability and adoption.

Requirements:

• 10+ years of Product Management experience, including at least 4+ years in a people management role leading Product Managers.
• Proven experience building, scaling, and mentoring high-performing product teams in fast-paced SaaS or technology environments.
• Strong ability to translate complex workflows into simple, intuitive, and user-friendly product experiences.
• Experience defining and executing multi-quarter product strategies that drive measurable business outcomes.
• Excellent analytical and problem-solving skills, with the ability to connect product decisions to business performance.
• Strong communication, storytelling, and stakeholder management skills, with the ability to influence executive leadership and cross-functional teams.
• Ability to operate effectively in ambiguous environments while balancing strategic thinking with operational execution.
• Experience in B2B SaaS, workflow automation, eSignature, or enterprise productivity products is highly valued.
• Strong coaching and leadership skills with a passion for developing talent and building inclusive, high-performing teams.
• Data fluency with the ability to analyze metrics and generate actionable insights to guide product direction.

Benefits:

• Competitive compensation ranging from 196,300 to 265,500 CAD depending on experience and location.
• Remote-friendly work environment with flexibility across eligible regions in Canada and the United States.
• Opportunity to lead and shape a high-impact product used globally for secure digital agreements and workflows.
• Strong focus on professional growth, leadership development, and career advancement in product management.
• Collaborative, cross-functional culture working alongside world-class engineering, design, and business teams.
• Exposure to strategic decision-making at the highest levels of product and business leadership.
• Inclusive workplace culture that values diversity, equity, and innovation.