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. Company Description Dropbox is a special place where we are all seeking to fulfill our mission to design a more enlightened way of working. We’re looking for innovative talent to join us on our journey. The words shared by our founders at the start of Dropbox still ring true today. Wouldn’t it be great if our working environment—and the tools we use—were designed with people’s actual needs in mind? Imagine if every minute at work were well spent—if we could focus and spend our time on the things that matter. This is possible, and Dropbox is connecting the dots. The nearly 3,000 Dropboxers around the world have helped make Dropbox a living workspace - the place where people come together and their ideas come to life. Our 700+ million global users have been some of our best salespeople, and they have helped us acquire customers with incredible efficiency. As a result, we reached a billion dollar revenue run rate faster than any software-as-a-service company in history. Dropbox is making the dream of a fulfilling and seamless work life a reality. We hope you’ll join us on the journey. Team Description Our Business Strategy & Operations team sets and drives key business initiatives across the company. We complement and support product, engineering, sales, and marketing teams across three critical areas: corporate and business unit strategy, business planning and sales operations, and business systems and tools development. Role Description As the Head 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. Translate business objectives into sales and retention goals that scale down to global sub-regions and route to marketOptimize sales performance tracking and 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 modelingExperience with sales operations functions within CRM (SalesForce) and Incentive Management tools (Forma) Strong verbal and written communication skillsInterpersonal skills with a proven ability to engage at all sales role levels; from rep to executivesAbility to adapt and scale work within high-demand periods across financial yearStrong 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. CompensationCanada Pay Range$161,800—$218,800 CAD The range listed above is the expected annual salary/OTE 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). Benefits Dropbox is committed to investing in the holistic health and wellbeing of all Dropboxers and their families. Our benefits and perks programs include, but are not limited to: Competitive medical, dental and vision coverage* Retirement savings through a defined contribution pension or savings plan** Flexible PTO/Paid Time Off policy in addition to statutory holidays, allowing you time to unplug, unwind, and refresh Income Protection Plans: Life and disability insurance* Business Travel Protection: Travel medical and accident insurance* Perks Allowance to be used on what matters most to you, whether that’s wellness, learning and development, food & groceries, and much more Parental benefits including: Parental Leave, Fertility Benefits, Adoptions and Surrogacy support, and Lactation support Mental health and wellness benefits Additional benefits details are available upon request. *Where group plans are not available, allowances may be provided **Benefit, amount, and type are dependent on geographical location, based upon applicable law or company policy   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. A big part of that effort is our support for members and allies of internal groups like Asians at Dropbox, BlackDropboxers, enABLE, TODOS (Latinx), Pridebox (LGBTQ), Vets at Dropbox, and Women at Dropbox.