Regional Vice President, to Medium Business
Toronto, Ontario, C6A, Canada
Listed on 2026-03-10
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Management
Business Management -
Business
Business Management
Company Overview
Docusign brings agreements to life. Over 1.5 million customers and more than a billion people in over 180 countries use Docusign solutions to accelerate the process of doing business and simplify people’s lives. With intelligent agreement management, Docusign unleashes business‑critical data that is trapped inside of documents. Until now, these were disconnected from business systems of record, costing businesses time, money, and opportunity.
Using Docusign’s Intelligent Agreement Management platform, companies can create, commit, and manage agreements with solutions created by the #1 company in e‑signature and contract lifecycle management (CLM).
The Regional Vice President, Small to Medium Business will lead a team of Account Executives. This sales leader will enable, coach, and lead the team to achieve key performance metrics. This strategic leader will lead a team to successfully achieve and exceed monthly and quarterly revenue quotas through proven leadership, strong business acumen, problem‑solving and consultative selling skills.
This strategic leader collaborates with the AEs on generating pipelines, running strong sales cycles, and closing new business. 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, Commercial Sales.
Responsibility
- Manage an SMB sales team daily to grow overall revenue of the Docusign Intelligence Agreement Management offering through attainment of monthly quotas
- Assess sales pipeline, activity and forecasts to determine sales progress and areas for refinement and improvement
- Coach AEs through the development of key SMB level sales skills, including vertical market management, MEDDPICC deal qualification methodology, forecasting and sales planning, prospecting/pipelining within account base, complex deal negotiations, cross‑functional support both internally and externally, as well as CRM/reporting accuracy, including performance management, creating a bench of qualified talent, and growing the team headcount as needed
- Develop proven and new strategies with AEs to further grow and expand SMB accounts and reinforce process and steps designed to deliver value at enterprise scale to Docusign customers
- Maintain positive and proactive lines of communication between different business partners as well as senior leadership, including 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 without requiring significant supervision
- Think creatively and independently to resolve conflict and solve problems
Hybrid: Employee divides their time between in‑office and remote work. Access to an office location is required. (Frequency: Minimum 2 days per week; may vary by team but will be weekly in‑office expectation)
Positions at Docusign are assigned a job designation of either In Office, Hybrid or Remote and are specific to the role/job. Preferred job designations are not guaranteed when changing positions within Docusign. Docusign reserves the right to change a position’s job designation depending on business needs and as permitted by local law.
What you bringBasic
- 2+ years of sales team management experience within software sales
- 5+ years of experience selling software in a quota‑carrying role
- BA/BS from an accredited college or university
Preferred
- 3+ years of prior leadership experience managing sales teams within software, ideally SaaS‑based offerings, both on‑premise and Cloud
- Quota‑attainment record of meeting and/or exceeding targets by managing process for identifying, qualifying, & closing new business as well as not limited to growing an existing install base
- Experience developing and maintaining business, sales, and market plans as well as negotiating and closing complex deal
- Track record of building, coaching and enabling a rapidly growing team
- Experience selling an eSignature or Agreement or Document…
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