Benefits Analyst

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 isn’t just a workplace—it’s a living lab for more enlightened ways of working. We're a global community of bold visionaries and resourceful doers who are shaping the future of Dropbox—and with it the future of work. Our Virtual First model combines the autonomy of a distributed workplace with the power of human connection, making space for both meaningful work and meaningful relationships. With our start-up mindset and enterprise-level opportunities, you can be who you are and grow into who you’re meant to be. Here, you can own your impact to make work more intuitive, joyful, and human—for you as a Dropboxer and for hundreds of millions of people worldwide. If you're ready to push boundaries—and yourself— Dropbox is ready for you.

Team Description

The Dropbox People Team designs experiences that empower Dropboxers to do their best work. As culture ambassadors, we craft an enlightened employee experience that infuses Virtual First with meaningful human connection. Our team continuously innovates to attract, develop, and retain world-class talent while building a culture of experimentation, craft, and community. From leadership programs, to talent acquisition, to employee engagement, we're creating a workplace where every Dropboxer can be who they are and grow into who they’re meant to be. If you're excited about designing more enlightened ways of working from the inside out, join our People team.

Areas of work include Talent Acquisition, Human Resources Business Partnership, Learning & Development, Recruitment, Total Rewards, and People Operations.

Role Description

We’re looking for a Benefits Analyst to join our Global Benefits team! The Benefits Analyst will work as part of a small but mighty team to ensure Dropbox offers competitive benefits to Dropboxers, which are optimized for Dropbox’s business goals, values and culture. If you’re passionate about benefits, self-motivated teammate with a curious nature, who loves partnering with colleagues to create delightful programs for employees, then this is the role for you!

Responsibilities

Responsibility for the ongoing management of benefit plans across the US and Canada including (but not limited to) leave of absence administration, disability plans, life insurance/risk insurance, medical, dental and vision insurance, COBRA, compliance etc.

Opportunity to support Int’l benefits

Manage/partner (with) our network of brokers and providers to ensure plans operate smoothly, project manage renewals and facilitate statutory or company driven updates/changes

Effectively manage cross functional partnerships with payroll, HRITS, human resources etc.

Focus on employee experience to ensure benefits and leaves are easily understood and accessible

Evolve existing processes and build operational excellence for benefit admin

Develop collaborative relationships with key partners across the organization to understand their objectives and how the Benefits team can support these goals

Requirements

Proven creativity and resourcefulness in solving problems

You thrive and prioritize in a constantly changing environment

You have superb communication skills, including experience effectively communicating with people at all levels of an organization

Analytical and structured thinking, working intelligently to understand the task at hand and relevant context in order to synthesize the main considerations and create astute proposals

Exceptional teamwork and multi-tasking skills

Understanding of compliance requirements and best practice

Minimum of 5+ years of benefits analyst experience with tech/sass company

Demonstrated ability to conceptualize employee experience as a product, with proven success applying product management principles (roadmapping, user journeys, feature prioritization) to HR initiatives

Proficiency in leveraging design thinking methodologies to deeply understand employee needs, rapidly prototype experience solutions, and implement data-driven iteration cycles that measurably enhance engagement and retention

Demonstrated experience leveraging AI tools in the flow of work. Candidates with a pre-existing comfort level and familiarity using AI to enhance productivity are strongly preferred.

Preferred Qualifications

Experience with tools such as Excel, Workday, ChatGPT

Experience working with a fast-paced Global Team

Compensation Canada Pay Range $+5,600—$12+,400 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.

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