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Director of Operations-HelloSign +DocSend - Location Flexible at Dropbox (Remote)

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Team Description
The HelloSign and DocSend teams (both brought into Dropbox by acquisition) are lines of business inside Dropbox, selling a suite of products to support document workflows, electronic signature, and electronic fax. Together, these businesses comprise a focus on document workflow and automation, with an aggressive 3-year plan to both grow the existing business and enter adjacent spaces through build, acquisition and partner motions. The team bullish on the growth opportunities, and we’re looking for the right business partner to help make sure we are on top of all our key metrics, reporting and planning.
Role Description
The head of operations will work very closely with the leadership team (LT) for both groups, along with the head of the document workflow organization and key business partners across Dropbox (both in Engineering/Product/Design and Global Commercial Operations). This individual will drive the processes and contributions needed for weekly/monthly/quarterly/annual reporting and planning across all of HelloSign and DocSend. Ideally, this person is thinking about and monitoring the key metrics day in and day out, ensuring we know how we’re performing and identifying areas for faster growth (including spend, headcount, prioritization, etc.) and/or risk mitigation.
  • HelloSign and DocSend OKR (Objectives and Key Results) planning/tracking/management
  • Ensuring the right data, key insights and initiatives are pulled together in the right cadence for business reviews (which happen weekly, monthly and quarterly)
  • Developing the content and commentary for monthly strategy reviews
  • Working across data, analytics and finance teams to ensure we have fully automated dashboards for all of our key metrics
  • Managing the cadence of functional reporting/updates for HelloSign and DocSend LT meetings
  • Headcount planning/oversight across all functions (and coordination with leaders of those teams and recruiting as needed)
  • Leading the process when there are investment opportunities/asks to submit to Dropbox leadership/finance
  • Running point on annual planning
  • You have at least 10 years of relevant experience in operations, strategy and planning, at least half of in a SaaS business
  • You have experience working in highly complex companies with multiple products and teams
  • You are fluent in financials and key SaaS metrics, and can interpret data easily
  • You have experience working with large data sets, and are able to slice, dice and present critical finds based on your analysis
  • You can communicate insights and recommendations to senior stakeholders through executive-level storytelling
  • You can manage multiple, complex and ambiguous projects by designing and implementing best-in-class business and operational practices
  • You are a team-player first and foremost, and believe great things come from collaboration
  • You’re always thinking about how you can adjust processes to make the team more effective 
  • Excellent written and verbal communication skills
  • BA/BS degree, MBA preferred
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Where we are

*Dropbox Studios are collaborative spaces designed for teamwork and community-building. Employees will not be able to use them for solo work.

Technology we use

  • Engineering
    • GolangLanguages
    • JavaLanguages
    • KotlinLanguages
    • FluxLibraries
    • jQueryLibraries
    • ReactLibraries
    • HadoopFrameworks
    • SparkFrameworks
    • TensorFlowFrameworks

What are Dropbox Perks + Benefits

Dropbox Benefits Overview

We’re proud to offer benefits that help all Dropboxers take care of their holistic selves, so they can keep flowing at work.

Volunteer in local community
Partners with Nonprofits
Friends outside of work
Eat lunch together
Intracompany committees
Open door policy
Team owned deliverables
Team based strategic planning
Group brainstorming sessions
Pair programming
Open office floor plan
Documented equal pay policy
Dedicated Diversity/Inclusion Staff
Unconscious bias training
Diversity manifesto
Diversity Employee Resource Groups
Hiring Practices that Promote Diversity
Health Insurance & Wellness Benefits
Flexible Spending Account (FSA)
Disability Insurance
Dental Benefits
Vision Benefits
Health Insurance Benefits
Life Insurance
Wellness Programs
Team workouts
Mental Health Benefits
Retirement & Stock Options Benefits
401(K) Matching
Company Equity
Performance Bonus
Match charitable contributions
Child Care & Parental Leave Benefits
Child Care Benefits
Generous Parental Leave
Flexible Work Schedule
Remote Work Program
Family Medical Leave
Adoption Assistance
Restricted work hours
Return-to-work program post parental leave
Vacation & Time Off Benefits
Unlimited Vacation Policy
Generous PTO
In addition to our Unlimited Vacation Policy, Dropbox also has one companywide PTO day a month
Paid Volunteer Time
At Dropbox, this is called 'Recharge'
Paid Holidays
Perks & Discounts
Beer on Tap
Casual Dress
Company Outings
Stocked Kitchen
Some Meals Provided
Happy Hours
Recreational Clubs
Relocation Assistance
Fitness Subsidies
Home Office Stipend for Remote Employees
Professional Development Benefits
Job Training & Conferences
Tuition Reimbursement
Diversity Program
Lunch and learns
Cross functional training encouraged
Promote from within
Mentorship program
Continuing Education stipend
Time allotted for learning
Online course subscriptions available
Customized development tracks

Additional Perks + Benefits

We began a new 'Perks Allowance' in 2021 when we went Virtual First. Dropboxers are provided a generous individual allowance to spend on what perks really matter to them while at home- whether that's wellness, caregiver support, productivity, ergonomics, learning, food services, afterschool programs for kids, or something else! Read more here: https://bit.ly/3uM0gG3

An Insider's view of Dropbox

How would you describe the company’s work-life balance?

In the first time in over a decade, I’ve been able to actually have work life balance and to develop healthy habits because of Virtual First. My commute time is now filled with a morning workout and the end of my day now looks like being able to cook for myself. I also was able to move closer to family, which means the world to me.


Diversity Program Manager

What's the biggest problem your team is solving?

In a world that’s radically shifting virtual, it’s exciting to be at a company aiming to solve a lot of the problems at the crux of the transition. I’ve been working on projects that help small businesses using Dropbox collaborate and improve their overall user experience.


Software Engineer

How does the company support your career growth?

Dropbox has provided me a great opportunity to work with some of the top talent in the industry. The amount of creativity and innovation I have been apart of has been amazing. Whether you’re an individual contributor or a VP, Dropbox provides amazing opportunity, training, and support for your career.


Head of Physical Infrastructure

What is your vision for the company?

I see the 40-hour office workweek becoming a thing of the past. Employees will escape grueling commutes and gain more control over their day. The workplace will now be wherever work happens, and the workweek will be whenever work happens best for each person. We'll grow stronger as we integrate dispersed talent with diverse perspectives.


Co-founder and CEO

How does the company support your career growth?

There’s always an opportunity to pivot and learn new skills or internally transfer to a team that’s outside your normal scope of work. The humility and empathy that Dropboxers have is unlike anywhere else I’ve worked. There’s always going to be someone on the other side willing to bring you in on a project or mentor you.


Content Marketing Operations

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