Director, Sales Compensation

Namely; Saskatchewan; Remote; CAD 180,000 - 280,000; Full time

Job summary

Dropbox is seeking a Head of Sales Compensation & Planning to lead global compensation, quota strategy, and incentive planning within the CSO organization. This leader will partner with executive leadership across Finance, HR, Strategy, and Sales Operations to translate objectives into scalable programs that drive revenue, profitability, and seller productivity across routes to market.

The role requires deep expertise in compensation design, governance, and executive-level communication, with a

Qualifications

• Design and govern global sales compensation programs.
• Lead quota methodologies and incentive planning.
• Partner with sales leadership, finance, HR, and strategy.
• Drive data-driven recommendations to improve performance.

Responsibilities

• Define long-term compensation philosophy and governance.
• Advise executive leadership on compensation strategy and planning decisions.
• Balance revenue growth with profitability while ensuring governance.
• Evolve incentive models to support transformation and scalability.

Skills

Sales compensation design

Quota methodologies

Financial modeling

Executive stakeholder management

Data-driven decision making

Cross-functional leadership

Education

Bachelor’s degree in business/finance

Tools

Salesforce

Forma

Tableau

Job description

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

As the Head of Sales Compensation & Planning within the Customer Strategy & Operations (CSO) organization, you will define and lead Dropbox's global sales compensation, quota strategy, and incentive planning framework. You will be responsible for shaping the philosophy, governance, and execution of compensation programs that drive revenue growth, profitability, and seller productivity across multiple routes to market.

This leader will partner closely with Executive Sales Leadership, Finance, Accounting, HR, and Strategy to translate business objectives into scalable incentive programs, quota methodologies, and sales planning decisionsthat accelerate performance while ensuring financial discipline. Beyond leading one of Dropbox's most business-critical operational functions, this role will influence how Dropbox motivates its global sales organization, aligns incentives to business strategy, and evolves our go-to-market model over time.

The ideal candidate combines deep expertise in sales compensation and planning with strong commercial acumen, executive presence, and the ability to influence senior stakeholders through data-driven recommendations. Reporting to the Head of Revenue Operations, this role will have significant visibility across Dropbox's executive leadership team and serve as a trusted advisor on sales performance, incentive strategy, and organizational planning.

Responsibilities

• Define Dropbox's long-term sales compensation philosophy, quota methodology, and incentive governance aligned to evolving business strategy.
• Serve as the primary advisor to Executive Sales Leadership, Finance, and CSO leadership on compensation strategy, seller productivity, and annual planning decisions.
• Influence executive decision-making through data-driven recommendations balancing revenue growth, profitability, customer outcomes, and employee motivation.
• Evaluate market trends and emerging GTM models to continuously evolve Dropbox's compensation and planning strategies.
• Partner with the Sales Operations organization to ensure compensation strategy, quota methodology, and planning decisions remain aligned with Dropbox's commercial strategy.
• Own the global design, governance, and evolution of scalable sales compensation programs across multiple products, customer segments, and routes to market.
• Partner cross-functionally to ensure compensation programs drive strategic priorities while remaining financially sustainable, equitable, and compliant.
• Establish governance processes for plan changes, new product launches, acquisitions, and evolving sales motions.
• Serve as the business owner for the incentive compensation platform (Forma), partnering with Systems to prioritize enhancements, maintain governance, and ensure the platform effectively supports compensation operations.
• Define compensation philosophies, principles, and governance for new sales roles, emerging routes to market, and evolving go-to-market motions, ensuring consistent and scalable incentive design.
• Establish frameworks for evaluating, piloting, and scaling new incentive models that support business transformation while maintaining governance, financial discipline, and seller trust.
• Lead the quota planning workstream within the annual sales planning process, partnering closely with Sales Operations, Finance, and Sales Leadership to ensure quota methodologies support business objectives, seller productivity, and compensation strategy.
• Develop and maintain quota methodologies, governance, and planning frameworks, while evolving ownership and operating models in partnership with Sales Operations as the organization scales.
• Partner on annual sales planning decisions, translating commercial priorities into scalable quota and incentive recommendations that support evolving go-to-market strategies.
• Evaluate seller productivity, quota attainment, and commercial performance to recommend planning and compensation adjustments that improve business outcomes.
• Provide strategic thought leadership on commercial planning, ensuring compensation, quotas, and incentives remain aligned as Dropbox's operating model continues to evolve.
• Own the end-to-end incentive compensation operations, including quarter-end and year-end compensation processes, payout calculations, governance, executive reporting, and payroll readiness.
• Lead quarter-end and fiscal year-end compensation execution, ensuring accurate and timely seller payouts while partnering closely with Payroll, Finance, HR, and Sales Operations to resolve exceptions and maintain operational excellence.
• Drive continuous improvement through automation, scalable systems, and simplified operational processes.
• Partner with Systems and Operations teams to enhance Salesforce, Forma, and reporting capabilities supporting incentive management.
• Build, mentor, and develop a high-performing compensation and planning function capable of supporting Dropbox's future growth.
• Foster strong cross-functional partnerships across Finance, Sales, HR, Revenue Operations, and Executive Leadership.
• Build a strong operating partnership with the Sales Operations organization to ensure alignment across planning, coverage, quotas, and compensation.
• Lead through influence across global stakeholders while driving alignment during annual planning and business transformation initiatives.

Requirements

• 12+ years of experience in sales compensation, sales operations, finance, or a related field with at least 5 years in a leadership role managing sales compensation and planning.
• Deep knowledge of sales compensation design, quota-setting best practices, incentive operations, and quarter-end compensation execution.
• Demonstrated experience designing executive-level compensation strategies supporting complex, multi-product SaaS organizations.
• Deep expertise in sales compensation design, quota methodologies, and financial modeling, with experience partnering on territory planning and sales planning processes.
• Proven ability to influence executive leadership and drive strategic decisions through analytical insights.
• Strong commercial acumen with the ability to balance revenue growth, seller behavior, customer outcomes, and financial performance.
• Experience leading large cross-functional planning initiatives involving Finance, Sales Leadership, HR, and Operations.
• Advanced analytical capabilities including Excel, financial modeling, scenario planning, and executive business reviews.
• Experience with Salesforce, incentive compensation platforms (Forma preferred), and reporting tools such as Tableau.
• Demonstrated ability to automate and simplify day-to-day compensation operations, reducing administrative effort and allowing the team to focus on higher-value activities such as compensation strategy, planning, and business partnership.
• Excellent executive communication, presentation, and stakeholder management skills.
• Demonstrated ability to build scalable processes and lead organizational change in fast-paced, high-growth environments.

Preferred Qualifications

• Experience leading global sales planning and incentive strategy for enterprise SaaS organizations.
• Strong understanding of P&L management, annual operating planning, and revenue forecasting.
• Experience supporting multiple sales motions including Direct, Channel, Enterprise, and Self-Serve.
• Familiarity with AI-driven sales planning, predictive productivity modeling, or next-generation incentive optimization tools.

Durable 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

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).

Read more about our benefits here.

Company Description

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 Dropbox Business Strategy & Operations team unlocks the company’s full potential by driving strategic initiatives and promoting operational excellence. We combine analytical rigor with creative problem-solving to tackle Dropbox’s biggest opportunities and challenges across all business functions. Partnering closely with Product, Engineering, Sales, Marketing, and Finance, we translate our strategic vision into actionable plans that foster growth, optimize performance, and facilitate informed decision-making. Our work shapes the future of Dropbox by leading cross-functional business planning, developing insights that guide corporate and business unit strategies, creating systems and processes that power scalable success. If you're passionate about strategic thinking, solving complex problems, and making an impact through collaboration, join our Business Strategy & Operations team.

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.

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