Case Study: Stack Exchange achieves automated stock option grants and reduced admin overhead with Dropbox Sign

Stack Exchange Uses HelloSign’s API to Automate Stock Option Grants

Stack Exchange, a Q&A network with over 200 employees, faced a recurring paperwork bottleneck: four times a year they sent personalized stock option grant packets, each batch requiring 40–100 documents to be completed. CFO Jack Sinclair managed creation by mail merge but struggled with tracking, follow-ups, errors and lost employee time, prompting the team to seek a technical solution.

Engineer Yaakov Ellis integrated the HelloSign eSignature API, using a HelloSign template and a spreadsheet-driven workflow to automate sending and embedded signing. The integration and testing took about a week (planning under a week), eliminated much of Jack’s admin burden, saved hours of work, and improved accuracy and completeness; the tool was quickly extended to distribute two more documents to 100+ U.S. employees in less than a day.

Stack Exchange

Jack Sinclair

CFO