Senior Strategy & Operations Program Manager

Role Description

At Dropbox, we believe in simplifying the way people work together. We provide a range of innovative cloud-based solutions to empower individuals and businesses to share, access, and collaborate on their files seamlessly. We’re looking for an experienced Senior Strategy & Operations Program Manager to partner across the organization to develop our strategy and develop the operational mechanisms to ensure we successfully deliver against our goals.

As a Senior Strategy & Operations Program Manager, you will join a small, high-impact team that partners across Product, Engineering, Design, GTM, and Executive leadership to drive end-to-end operational excellence: from shaping long-term strategy and business planning to overseeing execution, removing operational friction, and enabling rapid product development cycles. This is a senior individual-contributor role, and requires the ability to work effectively with executive leaders, EPD teams (engineering, product, design), and across organizational boundaries. The ideal candidate brings deep program management chops, a strategic mindset, and the ability to translate high-level vision into clear, actionable plans and operational cadence.

Responsibilities

• Partner with senior leadership and executives to define the strategic vision and then translate it into prioritized goals and concrete execution roadmaps.

• Define, implement, and manage operating cadences for the division (e.g. goals, QBRs, roadmap reviews, launch planning, regular exec-level briefings) to ensure alignment, accountability, and transparency.

• Build and maintain frameworks for tracking performance metrics, KPIs, business outcomes, and post-mortems — enabling continuous improvement and iterative learning.

• Facilitate cross-functional alignment and communication across Product, Engineering, Design, GTM, and other teams; surface and resolve interdependencies, resource constraints, and blockers.

• Lead cross-functional strategic initiatives from ideation and opportunity sizing, through planning, execution and measurement — blending strategy, program management, and operational execution.

• Produce high-quality executive-level deliverables and presentations (strategic plans, business reviews, board-ready materials) that distill complexity into clarity for leadership.

• Act as an operational “glue”: identify inefficiencies, implement process improvements, and build scalable workflows and systems that support fast-moving, high-growth product development cycles.

Requirements

• 10+ years of experience in program management, business operations, strategy, or related roles at a high-growth tech company (SaaS/product-led)

• Proven track record of successfully leading multi-function, cross-organizational programs from concept through delivery, including leading stakeholder alignment across teams (Product, Engineering, Design, GTM, Finance, etc)

• Demonstrated ability to use data to drive decision making and identify business opportunities, including experience with Excel, Tableau, Amplitude, or other analytics tools

• Experience leading strategic planning cycles, goal setting, business rhythms, and daily operations in a large organization

• Exceptional communication and interpersonal skills; proven experience preparing executive-level presentations, business reviews, and strategic narratives for senior leadership or board audiences

• Ability to switch between high-level strategic thinking and detail-oriented execution

• Strong bias for action, high ownership mindset, and comfort navigating ambiguity and complexity

Preferred Qualifications

• Prior experience in product management or corporate strategy, especially for technology companies

• Prior experience in a product-led SaaS company, ideally with exposure to building or scaling core platform/business-critical systems

• Demonstrated success designing and running SMART goals or similar operating cadence frameworks at scale

• Skilled at stakeholder management: building relationships and consensus across diverse functional teams — Product, Engineering, GTM, Finance, etc

• Prior exposure to building systems, processes, or tooling to support program management, cross-functional execution, or operational scaling

Compensation

Canada Pay Range
$178,500—$241,500 CAD