Senior Group Product Manager, Dropbox Sign

Job description

Accountabilities: 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. How Jobgether works: We use an AI-powered matching process to ensure your application is reviewed quickly, objectively, and fairly against the role's core requirements. Our system identifies the top-fitting candidates, and this shortlist is then shared directly with the hiring company. The final decision and next steps (interviews, assessments) are managed by their internal team. We appreciate your interest and wish you the best! Why Apply Through Jobgether? Data Privacy Notice: By submitting your application, you acknowledge that Jobgether will process your personal data to evaluate your candidacy and share relevant information with the hiring employer. This processing is based on legitimate interest and pre-contractual measures under applicable data protection laws (including GDPR). You may exercise your rights (access, rectification, erasure, objection) at any time. #LI-CL1 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.