Account Executive, Mid Market

Location: Toronto, Canada

Department: Sales & Partnerships

Work Mode: Hybrid

About the Role

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 business processes and simplify lives. With our Intelligent Agreement Management platform, we unleash business-critical data trapped in documents, integrating e-signature and contract lifecycle management (CLM) to connect agreements with systems of record—saving time, money, and opportunities. As the #1 company in e-signature and CLM, Docusign fosters an innovation culture where bold ideas thrive, and we're seeking a driven Account Executive, Mid Market to expand our impact. As an Account Executive (AE), Mid Market, you are a highly motivated self-starter responsible for expanding our footprint within current customers in an assigned geographic territory. Eager to learn and adapt quickly, you'll thrive in ambiguity while focusing on selling additional use cases, products, and services into existing accounts. Accountable for quarterly quotas, proactive deal management, forecast accuracy, and driving adoption of our e-signature and CLM solutions, you'll collaborate with internal teams and the DocuSign partner ecosystem. This individual contributor role reports to the Regional Vice President, Commercial Sales, in our dynamic Sales & Partnerships team. You'll drive success by building pipelines through prospecting, delivering tailored demos, negotiating enterprise proposals, and forecasting with precision using Salesforce. Leverage resources like Solutions Engineers and Partner Account Managers to close complex deals and boost usage of our Intelligent Agreement Management platform. This hybrid role requires a minimum of 2 days per week in-office, blending collaboration with flexibility. Join DocuSign's inclusive culture committed to trust, equality, and making the world more agreeable—where your contributions fuel innovation and customer success.

Key Responsibilities

• Drive company success by achieving and exceeding individual quarterly sales quotas in assigned geographic territory or core verticals
• Expand DocuSign's footprint in current customers by selling additional use cases, products, and services like e-signature and CLM solutions
• Build and manage a robust sales pipeline through proactive prospecting efforts into existing accounts
• Develop and deliver customized sales presentations and product demonstrations via phone and online demos
• Negotiate and close enterprise-level proposals and contracts
• Forecast sales activity and revenue accurately using Salesforce and other sales tools
• Collaborate with internal teams including Sales Development Representatives, Solutions Engineers, Account Managers, Partner Account Managers, Legal, Security, Professional Services, and Customer Support
• Drive customer adoption and usage of DocuSign's Intelligent Agreement Management platform
• Proactively manage deals to ensure forecast accuracy and quarterly goals
• Engage with the broader DocuSign partner ecosystem to accelerate sales opportunities

Required Qualifications

• BS/BA degree or equivalent relevant experience
• 2+ years of experience in an Account Executive role or equivalent quota-carrying sales position
• Experience selling web-based products or services
• Proven experience managing and closing complex sales cycles
• Proficiency in computer applications including Salesforce.com, Microsoft Word, PowerPoint, and Excel
• Familiarity with Google Workspace
• Ability to thrive in a fast-paced environment with ambiguity

Preferred Qualifications

• 3+ years of SaaS sales experience, ideally in e-signature or agreement management solutions
• Demonstrated history of over-achieving quotas (top 10-20% of company) in previous roles
• Experience expanding footprint within existing customer accounts
• Knowledge of intelligent agreement management platforms or CLM tools
• Success in selling into mid-market segments

Required Skills

• Quota attainment and overachievement
• SaaS sales expertise
• Pipeline building and management
• Complex sales cycle navigation
• Salesforce.com proficiency
• Presentation and demo delivery
• Negotiation and contract management
• Forecasting accuracy
• Cross-functional collaboration
• Customer adoption driving
• Prospecting and territory management
• E-signature and CLM product knowledge
• Adaptability in ambiguous environments
• Self-motivation and proactive mindset
• Web-based product sales experience
• Microsoft Office Suite (Word, PowerPoint, Excel)
• Google Workspace familiarity

Benefits

• Competitive base salary plus uncapped commission and performance bonuses
• Comprehensive health, dental, and vision insurance coverage
• 401(k) retirement savings plan with company match
• Flexible time off policy including unlimited PTO
• Professional development stipend and learning opportunities
• Hybrid work model with collaborative in-office experiences
• Stock purchase plan and employee stock purchase program
• Wellness programs, mental health support, and fitness reimbursements
• Parental leave and family-friendly benefits

DocuSign is an Equal Opportunity Employer.