Account Executive, Small to Medium Business

Docusign • Chicago, IL

1d • Hybrid

About The Position

As an SMB Account Executive at Docusign, you will drive revenue growth and market expansion across small and medium-sized businesses. This role requires a dynamic, adaptable sales professional who can seamlessly balance high-velocity transactional sales with strategic, multi-threaded platform deals. As Docusign expands into Intelligent Agreement Management (IAM) and AI-driven agreement solutions, you will translate complex capabilities into measurable business value for C-suite buyers.

Requirements

• 1+ years in a full-cycle, quota-carrying sales role within SaaS or technology
• Demonstrated history of consistent quota achievement (100%+ attainment)
• Proficiency with Salesforce (or HubSpot) and prospecting tools (e.g., Sales Navigator, Outreach)

Nice To Haves

• Experience balancing high-velocity transactional selling with broader platform deals
• Formal training in recognized sales methodologies (e.g., MEDDPICC, SPIN Selling)
• Exceptional communication skills with the ability to quickly establish trust with business leaders
• Adaptable, resilient, and eager to leverage new AI and agreement management tools
• Knowledge of legal and regulatory frameworks surrounding digital agreements
• Bachelor’s degree in a relevant field or equivalent practical experience

Responsibilities

• Exceed quarterly quotas and target continuous double-digit growth through new customer acquisition and account expansion
• Build a healthy pipeline proactively using outbound prospecting strategies, modern sales tools, and multi-channel outreach (phone, email, LinkedIn, WhatsApp)
• Conduct deep discovery to understand customer pain points across HR, Legal Procurement, and Operations
• Simplify complex IAM and AI features into clear ROI and business outcomes
• Use structured sales methodologies (e.g., MEDDPICC) to manage deal velocity, navigate longer sales cycles, and maintain accurate forecasting
• Maintain real-time CRM integrity in Salesforce, manage daily workflow efficiency, and keep high deal volumes moving predictably
• Collaborate with Solutions Engineers, Customer Success, and Legal to ensure seamless deal execution and customer onboarding

Benefits

• Bonus: Sales personnel are eligible for variable incentive pay dependent on their achievement of pre-established sales goals. Non-Sales roles are eligible for a company bonus plan, which is calculated as a percentage of eligible wages and dependent on company performance.
• Paid Time Off: earned time off, as well as paid company holidays based on region
• Paid Parental Leave: take up to six months off with your child after birth, adoption or foster care placement
• Full Health Benefits Plans: options for 100% employer paid and minimum employee contribution health plans from day one of employment
• Retirement Plans: select retirement and pension programs with potential for employer contributions
• Learning and Development: options for coaching, online courses and education reimbursements
• Compassionate Care Leave: paid time off following the loss of a loved one and other life-changing events

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: Associate degree