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

We are looking for a data-driven, systems-thinking Sales Operations Manager to own the operating infrastructure that powers our go-to-market engine. In this highly visible Individual Contributor role, you will serve as the backbone of a regional Sales organization and translate go-to-market strategy into an executable operating model.

You will act as the primary regional business partner for sales executives, supporting all routes to market within the region. You will own or coordinate supporting sales planning, territory and quota execution, forecast interpretation, operational improvements, and translation of strategic priorities into clear execution plans.

You’ll drive process clarity, pipeline health, forecasting hygiene, and cross-functional governance, using AI and automation-enabled workflows to reduce manual reporting effort while maintaining strong human judgment over business recommendations.

Your top priority each day will be to ensure excellence in execution and reporting on our regional goals.

Responsibilities

- Own the operating cadence, including territory management, account segmentation, forecasting governance, pipeline inspection, business reviews, and performance visibility, delivering executive-ready insights that drive forecast accuracy, balanced sales coverage, and operational excellence.Partner with regional Sales leaders across all routes to market to improve forecast accuracy, pipeline health, sales coverage, deal quality, and operational execution.
- Work in close partnership with the Chief Business Officer’s organization and the GTM Strategy & Programs team to connect regional Sales Operations to company-wide priorities, provide timely inputs for executive reporting, and ensure consistency across regional and corporate operating cadences.
- Lead end-to-end coverage design, including segmentation, book cutting, territory planning, account assignment, capacity planning, and quota allocation in partnership with Sales Leadership, Compensation, Finance, Systems, and Analytics.
- Own CRM QA and hygiene for the supported region, including SFDC hierarchy management, pipeline quality, process compliance, forecast integrity, deal quality investigations, and exception resolution.
- Partner with leadership on pipeline inspection, forecasting, and opportunity assessment, and build executive-ready reporting, dashboards, MBR/QBR readouts, and business insights that help leaders identify risks and make better decisions.
- Partner with Sales Strategy, Systems, Analytics, Compensation, Finance, and Enablement to automate recurring workflows and continuously improve how the team operates.
- Support organization design, interim coverage plans, role changes, recent-hire onboarding, SPIF development and administration, and Channel deal registration as part of the regional operating model.

Requirements

- Bachelor's degree or equivalent practical experience.
- 8+ years of experience in sales operations, business strategy, investment banking, venture capital, private equity, or corporate advisory, or 6 years of experience with an advanced degree.
- 4+ years of experience working with executive stakeholders.
- Experience leading territory planning,



account segmentation, forecasting, pipeline inspection, and annual sales planning processes.
- Deep understanding of quota planning, sales capacity modeling, and quota governance, with the ability to align quotas to business strategy and commercial objectives.
- Experience using AI, automation, and analytics tools to improve forecasting, pipeline inspection, reporting, and workflow efficiency, with the ability to validate outputs and apply sound business judgment before making recommendations.

Preferred Qualifications

- Experience supporting executive operating cadences (e.g., Weekly Business Reviews, Forecast Calls, Quarterly Business Reviews) for senior sales leadership.
- Experience designing or optimizing territory, account segmentation, or book-of-business models for high-growth SaaS organizations.
- Experience developing quota methodologies, allocating quotas, and partnering with Sales Leadership and Finance to align quotas with territory design, capacity planning, and business objectives.
- Experience supporting multiple sales motions (Direct, Channel, Self-Serve, Enterprise) across global or multi-region organizations.
- Strong proficiency with Salesforce, Tableau, SQL, or similar business intelligence and CRM platforms.
- Experience operating in a high-growth or transformational environment where Sales Operations played a strategic role in scaling the business.

Durable Skills Skills AI fluency means using these tools to amplify human judgment, not replace it. We believe people with these skills will thrive as work and technology continue to evolve:

- Awareness: Understand yourself and others.
- Judgment: Evaluate information and make decisions in complex situations.
- Adaptability: Learn, adjust, and stay effective through change.
- Connection: Communicate, collaborate, and build trust.

To learn more about why these skills matter and what the data shows about thriving through change, read this blog post from our Chief People Officer, Melanie Rosenwasser.

Compensation Canada Pay Range

$130,900—$177,100 CAD The range listed above is the expected annual salary/OTE (On-Target Earnings) 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 Read more about our benefits here.

Dropbox isn’t just a workplace—it’s a living lab for designing a more enlightened way of working. We’re a global community of bold visionaries and resourceful doers shaping the future of Dropbox and, in turn, the future of work.

Our Virtual

First model combines the autonomy of a distributed workplace with the power of human connection, creating space for meaningful work and lasting relationships. With a startup mindset and enterprise-level opportunities, we expect Dropbox employees to think critically,



stay curious, and use modern tools, including AI, to improve how work gets done. Here, you can be who you are and grow into who you’re meant to be. You own your impact, helping make work more intuitive, joyful, and human for yourself and hundreds of millions of people worldwide. If you’re ready to push boundaries and challenge yourself, Dropbox is ready for you.

Team Description The Company Strategy & Operations team (CS&O;) is part of the Office of the CEO (OCEO). We partner with Dropbox’s most senior leaders to drive the CEO’s vision forward by bringing focus and structure to the company’s most important work.

Our team combines strategic thinking with strong operations — we ask the right questions, navigate ambiguity, and partner with teams to help maintain alignment. Whether we’re shaping strategy, managing operating rhythms, or driving cross-functional collaboration, we do it with clarity, humility, and impact. If you thrive in complexity and enjoy building alongside others — you’ll find your people here.

Virtual First Dropbox’s Virtual First way of working is designed to help people do their best work with flexibility, autonomy, and connection. Day to day, teams work remotely with nonlinear schedules and core collaboration hours that support deep focus and individual working styles.

We prioritize asynchronous communication to improve clarity, respect deep work time, and reduce unnecessary meetings. While remote work is the primary experience for our employees, we also prioritize intentional, in-person connection. We bring teams together through regular team gatherings, on-demand workspaces, and Dropbox Neighborhood events in order to strengthen team cohesion, foster creativity, and enhance momentum.

Virtual

First is built to provide the same access to opportunity, growth, and impact for everyone, regardless of location.

This role requires travel to offsites and various other team gatherings (approximately 5-10% of the year or 2-3 days per quarter). We provide advance notice when possible and encourage candidates to discuss any accommodation needs during the interview process.

AI Fluency AI fluency is a core part of how we work and grow. It’s not about being an expert—it’s about using these tools thoughtfully and effectively to improve your work and support others.

We Look For Four Key Behaviors In Candidates

- Ownership: You use AI responsibly by protecting data, applying sound judgment, and taking accountability for the quality and accuracy of your work.
- Experimentation: You explore new AI capabilities and apply them to improve workflows within approved tools and practices.
- Leverage: You use AI to enhance thinking, improve efficiency, and increase your impact and your team’s.
- Learning: You stay current on emerging AI tools and trends, continuously build your skills, and share what you learn with others.

Together, these behaviors help build a workforce where technology amplifies human judgment, creativity, and impact. Dropbox supports responsible use of AI for preparation, but misrepresentation of skills or experience is not permitted. To learn more, see our approach to AI in hiring.

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.

📌 Regional Sales Operations Manager - NAMER (Remote) (Canada)
🏢 Dropbox
📍 Canada