Pros
I work in the Sales Operations group in Seattle, WA and have experienced the growth from less than 100 employees to where we are now. The company has stayed true to its roots and core values. As an employee, there are always new challenges and opportunities to grow, work on new projects, meet new people, etc.
I've been in the software/technology industry for 30+ years, and DocuSign is my favorite company to be a part of and experience.
Kontras
As we have grown, processes and resources have not always kept up. The challenge as an employee is to help identify those needs and offer solutions. A side affect can be work and life getting out of balance.