Full-Time

Regional Sales Operations Manager

Namer

Posted on 9/8/2026

Dropbox

Dropbox

1,001-5,000 employees

Cloud storage, file sync, collaboration platform

Compensation Overview

CA$130.9k - CA$177.1k/yr

Remote in Canada

Remote

Remote within select locations in Canada.

Bachelor's

Category
Sales & Account Management (1)
Required Skills
Data Visualization
Forecasting
SQL
CRM
Tableau
Salesforce
Data Analysis

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Requirements
  • A bachelor's degree or equivalent practical experience.
  • At least 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.
  • At least 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 artificial intelligence, 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.
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 Go-to-Market 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 customer relationship management quality assurance and hygiene for the supported region, including Salesforce 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, monthly business review and quarterly business review 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, new-hire onboarding, sales performance incentive fund development and administration, and channel deal registration as part of the regional operating model.
Desired Qualifications
  • Experience supporting executive operating cadences, such as Weekly Business Reviews, Forecast Calls, and Quarterly Business Reviews, for senior sales leadership.
  • Experience designing or optimizing territory, account segmentation, or book-of-business models for high-growth software-as-a-service 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, including Direct, Channel, Self-Serve, and Enterprise, across global or multi-region organizations.
  • Strong proficiency with Salesforce, Tableau, SQL, or similar business intelligence and customer relationship management platforms.
  • Experience operating in a high-growth or transformational environment where Sales Operations played a strategic role in scaling the business.

Dropbox provides cloud storage and file synchronization for individuals and organizations, with features for storing, sharing, and collaborating on documents. Users upload files to online storage; the service syncs them across devices and makes them available in shared workspaces, with links, comments, and real-time collaboration. It differentiates itself with a simple interface, strong security, reliable syncing, and a growing ecosystem of integrations and partnerships including DocSend and HelloSign. Its goal is to support remote and distributed teams by offering a straightforward, secure way to access and work on files from anywhere while growing its subscription revenue.

Company Size

1,001-5,000

Company Stage

IPO

Headquarters

San Francisco, California

Founded

2007

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Simplify Jobs

Simplify's Take

What believers are saying

  • August 6, 2026 guidance raised operating margin to 40.0%-40.5% and FCF to $1.07B.
  • Dropbox added 96,000 paying users in Q2 2026, reaching 18.19 million.
  • Dropbox authorized a $1.2 billion buyback after securing a $2 billion credit facility.

What critics are saying

  • Core revenue grew only 0.9% in Q2 2026, exposing a mature business.
  • AI rollout lifted compute costs, cutting non-GAAP gross margin to 81.6% in Q2 2026.
  • Microsoft, Google, and Apple can bundle storage and search, crushing standalone pricing power.

What makes Dropbox unique

  • Dropbox Dash unifies search across files, apps, audio, and video for teams.
  • Ashraf Alkarmi and Drew Houston emphasize virtual-first culture, boosting 2026 hiring pull.
  • DocSend and e-signatures keep Dropbox inside high-trust document workflows, not commodity storage.

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Benefits

Competitive medical, dental & vision coverage

Competitive 401(k) Plan with a generous company match & immediate vesting

Flexible Time Off/Paid Time Off

11 Company-wide PTO days

Volunteer time off and more

Life Insurance, Disability Insurance & Travel benefit plans

Perks Allowance

Parental benefits

Mental Health & Wellness benefits

Free Dropbox space for your friends and family

Growth & Insights and Company News

Headcount

6 month growth

0%

1 year growth

1%

2 year growth

0%
Yahoo Finance
Aug 23rd, 2026
Dropbox CFO sells $25M in shares days after raising guidance

Dropbox CFO Ross Tennenbaum sold 20,326 shares of Class A Common Stock on 17 August, according to an SEC Form 4 filing. The transaction, valued at $25.34 million, was executed for tax purposes and does not reflect a change in the insider's assessment of the company's valuation. Tennenbaum continues to hold 759,000 shares directly, valued at $25.7 million based on the 18 August closing price. He also holds restricted stock units scheduled to vest through 15 November 2029, contingent upon continued service. Dropbox operates a software-as-a-service business model, generating revenue through tiered subscription plans for individual users, teams, and enterprises. The company has a market capitalisation of $8.6 billion and reported $2.5 billion in trailing twelve-month revenue.

Yahoo Finance
Aug 23rd, 2026
Dropbox CTO sells $1M in shares under pre-scheduled trading plan from May 2025

Dropbox CTO Ali Dasdan sold 30,587 Class A shares on 17-18 August, worth approximately $1 million, according to an SEC filing. The transaction included 19,255 shares withheld for taxes and 11,332 shares sold through a pre-scheduled trading plan. The tax withholding was a non-discretionary transaction triggered by vesting equity awards. The share sale was executed under a Rule 10b5-1 plan Dasdan adopted on 12 May 2025, allowing insiders to establish predetermined selling schedules for liquidity or diversification whilst maintaining regulatory compliance. Following the disposition, Dasdan holds 471,052 shares directly, representing a 6% decrease from his previous position of 501,639 shares. His remaining direct equity interest is valued at roughly $15.95 million and represents approximately 0.2% of the company. These holdings include restricted stock units scheduled to vest through 15 November 2030.

Yahoo Finance
Aug 23rd, 2026
Dropbox co-CEO sells $1.6M in shares following restricted stock vesting

Dropbox co-CEO Ashraf Alkarmi disposed of 47,865 shares on 17 August through a non-discretionary transaction, according to an SEC filing. The shares were withheld to cover tax obligations from vesting restricted stock units. The transaction was valued at $1.6 million. Alkarmi retains 1,032,881 shares of Class A common stock, worth $34.48 million as of the transaction date. The disposal was linked to a fixed vesting schedule rather than an open-market trade. As of 17 August, Dropbox shares had generated a one-year total return of 20%. Dropbox provides file management and collaboration solutions through subscription-based services. The company has a market capitalisation of $8.6 billion and reported revenue of $2.5 billion.

Yahoo Finance
Aug 16th, 2026
Two profitable stocks with strong fundamentals and one to avoid

Financial services firm Ares Management and commercial asset marketplace operator RB Global have been highlighted for their strong fundamentals and profitability, whilst cloud storage provider Dropbox faces challenges. Ares Management has demonstrated exceptional revenue growth of 24.3% annually over the past two years, with earnings per share compounding at 19.5% annually over five years. The company maintains an operating margin of 21.8%. RB Global, formerly Ritchie Bros. Auctioneers, has achieved 27.4% annual revenue growth over five years, with EPS growing at 19.3% annually. The company generates a free cash flow margin of 14%. Dropbox, despite a 26.6% operating margin, showed flat billings and faces weak demand outlook. Wall Street expects flat revenue over the next 12 months.

Dropbox, Inc.
Aug 10th, 2026
Introducing Dropbox Dash for Business — AI-powered Universal Search That Finds Anything and Protects Everything at Work | Dropbox

Dash for Business makes it easy for teams to find, organize, share, and secure company information by combining universal search, organization and sharing capabilities, and in-depth content access control for businesses of all sizes SAN FRANCISCO--( BUSINESS WIRE )--Today, Dropbox, Inc.