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 it with systems of record to save time, money, and opportunities. As the #1 company in e-signature and contract lifecycle management (CLM), Docusign empowers companies to create, commit, and manage agreements innovatively. As an Account Executive, Mid-Market, you are a highly motivated self-starter responsible for developing and closing new business in an assigned geographic territory. Eager to learn our cutting-edge e-signature and CLM solutions, you'll adapt quickly to drive acquisition of new customers and expansion into existing accounts with additional use cases. Accountable for exceeding monthly and quarterly quotas, you'll manage deals proactively, ensure forecast accuracy, and collaborate with internal teams and the Docusign partner ecosystem to boost adoption and usage. This individual contributor role reports to the Regional Vice President, Commercial Sales, in a hybrid designation requiring minimum 2 days per week in-office. What you'll do: Drive company goals by smashing sales quotas, building pipelines through territory prospecting, delivering tailored demos, negotiating enterprise contracts, forecasting precisely in Salesforce, and partnering across Sales Development, Solutions Engineering, Legal, and more. Thrive in our innovation culture where bold ideas simplify global agreements. At Docusign, we build trust, embrace equality, and foster deep pride in transformative work—join us to make the world more agreeable.

Key Responsibilities

• Drive company success by consistently achieving and exceeding individual monthly and quarterly sales quotas
• Build and manage a robust sales pipeline through proactive prospecting in assigned geographic territories or core verticals
• Develop and deliver customized sales presentations and product demonstrations via phone and online platforms
• Create, negotiate, and close enterprise-level proposals and contracts for new and expansion opportunities
• Accurately forecast sales activity and revenue using Salesforce and other sales tools
• Collaborate with cross-functional teams including Sales Development Representatives, Solutions Engineers, Account Managers, Partner Account Managers, Legal, Security, Professional Services, and Customer Support
• Acquire new customers and expand existing accounts by selling additional use cases, products, and services like e-signature and CLM solutions
• Proactively manage deals, ensure forecast accuracy, and drive customer adoption and usage in partnership with the Docusign ecosystem
• Adapt quickly to ambiguity while learning DocuSign's Intelligent Agreement Management platform

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 work in a hybrid environment with minimum 2 days per week in-office

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 selling into mid-market segments with geographic territory management
• Knowledge of intelligent agreement management platforms and contract lifecycle management (CLM)

Required Skills

• Quota attainment and overachievement
• Prospecting and pipeline management
• Complex sales cycle navigation
• Salesforce.com proficiency
• Presentation and demo delivery
• Contract negotiation
• Forecasting accuracy
• Cross-functional collaboration
• Self-starter mindset
• Adaptability to ambiguity
• Eager learning orientation
• Territory management
• SaaS sales expertise
• Customer adoption driving
• Web-based product sales
• Microsoft Office Suite (Word, PowerPoint, Excel)
• Google Workspace familiarity
• Intelligent agreement management knowledge

Benefits

• Competitive base salary plus uncapped commission and performance bonuses
• Comprehensive health, dental, and vision insurance with multiple plan options
• 401(k) retirement savings plan with generous company match
• Flexible time off including unlimited PTO and paid company holidays
• Professional development stipend and access to learning platforms
• Hybrid work model with home office setup allowance
• Stock purchase plan and employee stock purchase program
• Wellness programs including gym memberships and mental health support
• Parental leave and family planning benefits

DocuSign is an Equal Opportunity Employer.