Staff Product Manager, AI Evaluations

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 is seeking a Staff Product Manager to lead AI Evaluations (Evals) — the systems, metrics, and processes that measure the quality and reliability of AI-powered features across Dropbox. In this role, you’ll define how we evaluate model performance, accuracy, and user satisfaction across diverse AI surfaces like Dash, search, summarization, and intelligent organization.

You’ll collaborate closely with Applied AI, Data Science, and Research to design frameworks that ensure our AI features are helpful, safe, and high-quality. This includes everything from defining success metrics for model improvements, to building scalable pipelines that assess qualitative and quantitative signals at scale.

This role sits at the intersection of AI systems, data rigor, and product judgment — ideal for a PM who loves turning ambiguity into measurable progress and ensuring that every AI interaction meets a bar of excellence.

Responsibilities Define and drive the roadmap for Dropbox’s AI Evaluation Framework, covering both quantitative metrics and human-in-the-loop systems.

Partner with ML, data, and research teams to build evaluation pipelines that measure model accuracy, helpfulness, bias, latency, and hallucination rates.

Translate business and product goals into measurable AI performance objectives.

Develop taxonomies and methodologies for evaluating large language model (LLM) behaviors in production.

Work closely with PMs across Dash to integrate eval signals into product development loops.

Partner with infra and AI platform teams to operationalize eval tooling and dashboards.

Ensure evaluations are ethical, transparent, and aligned with Dropbox’s privacy and trust standards.

Communicate findings and drive accountability across teams for improving AI quality.

Requirements 10+ years of product management experience, ideally in AI/ML systems, data platforms, or experimentation.

Proven experience defining and shipping metrics-driven AI products or frameworks.

Strong understanding of model evaluation concepts such as precision/recall, win-rate testing, and user feedback loops.

Excellent analytical, problem-solving, and communication skills.

Strong cross-functional collaboration across ML, data, design, and research teams.

Comfort balancing experimentation speed with rigor and reproducibility.

Preferred Qualifications Background in AI systems, API design, or developer platforms.

Experience working on extensibility or plugin ecosystems.

Understanding of AI evaluation and safety frameworks.

Ability to influence across multiple product teams and technical domains.

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:

Flexible PTO/Paid Time Off, paid holidays, Volunteer Time Off, and more, allowing you time to unplug, unwind, and refresh

Perks Allowance to be used on what matters most to you, whether that’s wellness, learning and development, food and groceries, and much more

Mental health and wellness benefits

Monthly Internet Allowance

Intern Social Stipend

Annual Emerging Talent Summit, travel and hotel accommodations provided

Additional benefits details are available upon request.

Where group plans are not available, allowances may be provided

**Benefit, amount, and type are dependent on geographical location, based upon applicable law or company policy

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

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.