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As the Head of Sales Compensation and Planning, you will lead the strategy for sales compensation and quotas at Dropbox, ensuring alignment with business objectives. Responsibilities include managing compensation plans, handling payout calculations, collaborating with Finance, and optimizing sales performance.
Role Description
As the Senior Manager of Sales Compensation and Planning in the Customer Strategy & Operations (CSO) organization, you will play a critical role leading our sales compensation & quota strategy at Dropbox. This role will be responsible for designing and managing effective compensation plans, ensuring accurate and timely payout calculations, setting and managing sales quotas, and collaborating closely with Finance and Sales Leadership to align compensation with annual planning and business objectives.
The ideal candidate will bring a strategic mindset, strong analytical skills, and a proven ability to drive results in a multi-product growth environment. This position offers the opportunity to make a significant impact on the performance and motivation of our sales team while ensuring alignment with company goals. This role will be reporting into the Head of Customer Strategy & Operations and will have significant visibility across senior GTM leadership.
Responsibilities
- Develop and manage competitive, scalable, and motivating sales compensation plans that align with company objectives and market trends.
- Partner with Finance and Sales Leadership to continuously evaluate and enhance compensation programs to be compliant, equitable, and support financial targets.
- Own the end-to-end process sales compensation payouts including forecasting costs, calculating and processing with accuracy, handling escalations and inquiries, and ensuring clear communication.
- Leverage historical performance data and market trends to build “Books of Business” that ensure quotas by Direct and Channel role types drive optimal productivity to support business goals.
- Lead annual planning cycles translating business objectives into sales and retention quota goals, including quarterly assessments to iterate plans based on performance and feedback loops
- Build and maintain quotas by role, managing annual and quarterly plans, adapting based on change in strategy and offerings.
- Ensure global sub-regions and routes to market goals are balanced and adapted based on coverage models and productivity metrics
- Optimize sales performance tracking and own reporting requirements within incentive management tools and adapt to new offerings and sales motions.
Requirements
- 10+ years of experience in 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, and financial planning.
- Strong analytical skills with expertise in Excel and financial modeling
- Experience with sales operations functions within CRM (SalesForce) and Incentive Management tools (Forma)
- Strong verbal and written communication skills
- Interpersonal skills with a proven ability to engage at all sales role levels; from rep to executives
- Ability to adapt and scale work within high-demand periods across financial year
- Strong problem-solving skills and a proactive approach to driving improvements.
Preferred Qualifications
- Familiarity with P&L management and financial planning.
- Understands benchmarking around role productivity
- Proficiency with reporting tools like Tableau and other data visualization platforms.
Compensation
US Zone 1
This role is not available in Zone 1
US Zone 2
$185,100—$250,500 USD
US Zone 3
$164,600—$222,600 USD
Top Skills
Excel
Salesforce
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