Regional Vice President, Enterprise Sales


Regional Vice President, Enterprise Sales
Sales & Business Development | Toronto, Canada

Our agreement with employees
DocuSign is committed to building trust and making the world more agree-able for our employees, customers and the communities in which we live and work. You can count on us to listen, be honest, and try our best to do what’s right, every day. At DocuSign, everything is equal. We each have a responsibility to ensure every team member has an equal opportunity to succeed, to be heard, to exchange ideas openly, to build lasting relationships, and to do the work of their life. Best of all, you will be able to feel deep pride in the work you do, because your contribution helps us make the world better. And for that, you’ll be loved by us, our customers, and the world in which we live.

The team
Our Sales & Business Development teams collaborate with customers and partners across the globe to help them leverage the DocuSign Agreement Cloud to transform the entire system of agreement process—from preparing to signing, acting on, and managing contracts and other types of agreements. Our team’s partner with some of the largest most innovative companies in the world in dozens of industries to bring the power of DocuSign to more customers. Whether you are selling to a small business or a large enterprise, you will apply your extensive knowledge of our solutions, and leverage our strategic partnerships to help our customers grow their top and bottom line.

This position
The Regional Vice President of Enterprise Sales will lead a team of strategic, Enterprise sales professionals to drive new business opportunities within and growth of our entire solution suite. This sales leader must be able to empower, measure and motivate effectively, leading by example. They will need to be hands-on, assisting in opening doors, partnering on account calls, account health monitoring, and effectively maintaining strong account relationships. This leader is a mentor as well as a coach; and, is a true evangelist for the needs of the business.

This position is a people manager role reporting to the Area Vice President, Sales – Canada and is designated Remote.


  • Manage an Enterprise level field sales team daily – goal is to grow overall revenue of the DocuSign’s product suite across Canada
  • Assess sales pipeline, activity & forecasts to determine sales progress & areas for refinement/improvement
  • Coach AE’s through the development of key Enterprise level sales skills, including market management, forecasting & sales planning, prospecting/pipelining within account base, complex deal negotiations, cross-functional support both internally and externally, as well as CRM/reporting accuracy
  • Develop strong partnership with Talent Acquisition and Human Resources; helping to create and maintain a bench of qualified talent, and growing the team headcount as needed
  • Maintain positive and proactive line of communication between the lines of business as well as senior leadership; includes developing and delivering accurate forecast and attainment details during weekly and quarterly business reviews
  • Identify and support opportunities for training as well as career diversification and growth across the team
  • Operate well in a fast-paced, dynamic environment. Can think creatively and independently

Basic qualifications

  • 8+ years of sales team management experience, specifically within software sales
  • 12+ years prior experience selling software in a quota-carrying role
  • 5+ years experience with Digital Transformational software solutions, in either a leadership, direct sales, presales or customer success capacity

Preferred qualifications

  • 10+ years of prior leadership experience managing Enterprise, complex software selling Sales teams
  • 15+ years experience selling software in a quota-carrying role
  • Quota-attainment record of meeting and/or exceeding targets by managing process for identifying, qualifying, and closing new business as well as and not limited to growing an existing install base
  • Track record of building, coaching and enabling a rapidly growing team
  • Experience selling into a variety of industries and territories as well as experience cultivating larger, strategic relationships key
  • Capacity to work on cross-functional projects and teams as needed as well as leverage internal resources to problem-solve
  • Strong verbal and written communication skills – includes excellent reporting and forecasting skills. Attention to detail is critical
  • Willingness to travel 25% or more as needed

About us
DocuSign helps organizations connect and automate how they prepare, sign, act on, and manage agreements. As part of the DocuSign Agreement Cloud, DocuSign offers eSignature: the world's #1 way to sign electronically on practically any device, from almost anywhere, at any time. Today, over a million customers and hundreds of millions of users in over 180 countries use DocuSign to accelerate the process of doing business and simplify people's lives. And we help save the world’s forests and embrace environmental sustainability.

It’s important to us that we build a talented team that is as diverse as our customers and where all employees feel a deep sense of belonging and thrive. We encourage great talent who bring a range of perspectives to apply for our open positions. DocuSign makes hiring decisions based on experience, skill, aptitude and a can-do approach. We will not discriminate with regards to any legally protected characteristics.

DocuSign provides reasonable accommodations for qualified individuals with disabilities in job application procedures, including if you have any difficulty using our online system. If you need such an accommodation, you may contact us at

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