Senior Group Product Manager, Dropbox Sign

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