Role Description
As a Staff Product Manager focused on Reclaim.ai within Dropbox , you’ll play a pivotal role in evolving and accelerating the AI-powered scheduling and productivity capabilities of one of Dropbox’s most innovative acquisitions. You will lead product efforts across a wide surface area—from time orchestration, collaboration, and enterprise deployment to exploring adjacent markets that extend Reclaim’s impact. You’ll work directly with Reclaim’s co-founders (now part of Dropbox), while partnering closely with cross-functional leaders in engineering, design, marketing, sales, and support to shape a category-defining product experience.
This is a rare opportunity to operate like a startup PM—owning strategy, execution, and outcomes end-to-end—within the scope, scale, and resources of Dropbox. You’ll get deep exposure to senior leadership, significant latitude to chart your path, and the chance to transform how teams and individuals reclaim their time.
Responsibilities
Own and drive the product strategy and roadmap for Reclaim.ai, balancing long-term vision with short-term execution across key areas like AI scheduling, collaboration workflows, and enterprise features.
Partner with Reclaim’s co-founders and senior Dropbox leadership to align vision, priorities, and go-to-market strategies.
Collaborate deeply with engineering and design to bring features to life—writing specs, defining success metrics, and iterating based on feedback and data.
Work cross-functionally with marketing, sales, and support to ensure successful launches, adoption, and customer success across SMB and enterprise.
Engage directly with customers and users to deeply understand their needs, pain points, and evolving expectations.
Lead and inspire a high-functioning, fast-moving team through ambiguity, change, and rapid growth.
Champion a culture of experimentation, urgency, and customer obsession.
Requirements
12+ years of experience in product management or a closely related role, ideally across both early-stage and scaled product environments.
Proven track record building and scaling team collaboration, productivity, or scheduling products.
Demonstrated ability to work cross-functionally and influence across all levels—especially with senior leadership and executive stakeholders.
Experience in fast-paced, ambiguous environments with high ownership and low structure.
Strong product intuition with excellent written and verbal communication skills.
Comfortable with data—can define metrics, analyze trends, and use insights to inform decisions.
Deep empathy for users, especially those managing complex time and coordination workflows.
Preferred Qualifications
Experience working on AI-powered products or systems that involve smart automation, decision-making, or time optimization.
Familiarity with enterprise deployment models, including top-down SaaS adoption and IT/security needs.
Background working within or adjacent to B2B SaaS startups.
BA/BS degree in a technical or business discipline.
Exposure to design-forward product teams with strong user research practices.
Compensation
Canada Pay Range $191,300—$258,700 CAD
The range listed above is the expected annual salary/OTE for this role, subject to change.
Salary/OTE is just one component of Dropbox’s total rewards package. All regular employees are also eligible for the corporate bonus program or a sales incentive (target included in OTE) as well as stock in the form of Restricted Stock Units (RSUs).
Company Description
Dropbox isn’t just a workplace—it’s a living lab for more enlightened ways of working. We're a global community of bold visionaries and resourceful doers who are shaping the future of Dropbox—and with it the future of work. Our Virtual First model combines the autonomy of a distributed workplace with the power of human connection, making space for both meaningful work and meaningful relationships. With our start-up mindset and enterprise-level opportunities, you can be who you are and grow into who you’re meant to be. Here, you can own your impact to make work more intuitive, joyful, and human—for you as a Dropboxer and for hundreds of millions of people worldwide. If you're ready to push boundaries—and yourself— Dropbox is ready for you.
Team Description
The Dropbox Product Management Team envisions and builds the future of work while growing our business, one product at a time. We're strategic thinkers and advocates for our users, crafting solutions that make work more intuitive and joyful. Using data, research, and strategy—and a healthy dose of empathy—we guide cross-functional teams toward the shared goal of creating transformative products that people love to use. If you're passionate about building solutions that reshape how the world works while delighting users in the process, join our Product Management team.
Areas of work include Product Management, Product Strategy, User Research, Data Analytics, Product Operations, Growth Strategy, and Go-to-Market Planning.
Benefits
Dropbox is committed to investing in the holistic health and wellbeing of all Dropboxers and their families. Our benefits and perks programs include, but are not limited to:
Competitive medical, dental and vision coverage*
Retirement savings through a defined contribution pension or savings plan**
Flexible PTO/Paid Time Off policy in addition to statutory holidays, allowing you time to unplug, unwind, and refresh
Income Protection Plans: Life and disability insurance*
Business Travel Protection: Travel medical and accident insurance*
Perks Allowance to be used on what matters most to you, whether that’s wellness, learning and development, food & groceries, and much more
Parental benefits including: Parental Leave, Fertility Benefits, Adoptions and Surrogacy support, and Lactation support
Mental health and wellness benefits
Additional benefits details are available upon request.
- Where group plans are not available, allowances may be provided
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. A big part of that effort is our support for members and allies of internal groups like Asians at Dropbox, BlackDropboxers, enABLE, TODOS (Latinx), Pridebox (LGBTQ), Vets at Dropbox, and Women at Dropbox.