Director of Operations - HelloSign

DropBoxSan Francisco, CaliforniaFull TimeRemote

Company Description

Dropbox is a leading global collaboration platform that's transforming the way people work together, from the smallest business to the largest enterprise. With more than 500 million registered users across more than 180 countries, our mission is to design a more enlightened way of working. From our headquarters in San Francisco to eight dedicated Studios and a worldwide team of employees who choose where they work best, our Virtual First approach is leading the way into the future of work.

Team Description

Our Business Development team builds and manages a global partner ecosystem including device manufacturers, network providers, developers, and retailers. With a passion for action-oriented analytics, we work together to establish product, commercial, and strategic partnerships that help Dropbox and its partners grow.

Team Description

The HelloSign team is a line of business inside Dropbox, selling a suite of products to support document workflows, electronic signature, and electronic fax. HelloSign is the fastest growing business inside Dropbox, with an aggressive 3-year plan to both grow the existing business and enter adjacent spaces through build, acquisition and partner motions. The team is tight-knit, bullish on our 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 senior business manager will work very closely with the HelloSign leadership team (LT), along with key partners in New Businesses (the products group of which we are a part) and the Global Commercial Operations team. This individual will drive the processes and contributions needed for weekly/monthly/quarterly/annual reporting and planning across all of HelloSign. Ideally, this person is thinking about and monitoring our 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.).


  • HelloSign 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 the monthly strategy reviews
  • Working across data, analytics and finance teams to ensure we have a fully automated dashboard for all of our key metrics
  • Managing the cadence of functional reporting/updates for HelloSign LT meetings
  • Headcount planning/oversight across all HelloSign 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
  • You have experience working in highly complex companies with multiple products and teams
  • You are fluent in financials, 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/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

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, Latinx, Pridebox (LGBTQ), Vets at Dropbox, Women at Dropbox, ATX Diversity (based in Austin, Texas) and the Dropbox Empowerment Network (based in Dublin, Ireland).

Benefits and Perks

  • Generous company paid individual medical, dental, & vision insurance coverage
  • 401k + company match
  • Market competitive total compensation package
  • Free Dropbox space for your friends and family
  • Wellness Reimbursement
  • Generous vacation policy
  • 11 company paid holidays
  • Volunteer time off
  • Company sponsored tech talks (technology and other relevant professional topics)

Legal professional? Thousands of attorneys rely on to find legal work they love. Join today!
Product logo

Xakia is cost-effective and easy-to-implement legal matter management software for in-house legal teams of any size. It centralizes matte...