Enterprise Account Executive, Mail

This is a fully remote position, open to applicants in United States.

📋 Description

• New Logo Acquisition: Take ownership of the complete sales cycle for new enterprise accounts, from prospecting and pipeline creation to closing contracts. Develop and implement targeted outbound strategies to penetrate organizations with over 5,000 employees, engaging multiple stakeholders across various departments and levels.

• Account Expansion: Increase revenue within existing enterprise accounts by strategically upselling and cross-selling. Identify opportunities for expansion, collaborate with Customer Success to create growth plans, and drive adoption that transforms initial deployments into company-wide implementations.

• Renewal Management: Ensure timely renewals by consistently illustrating value and return on investment (ROI), proactively identifying and addressing churn risks, and developing retention strategies that safeguard and enhance the customer base.

• Executive Relationship Management: Establish strong, multi-faceted relationships within your accounts, engaging everyone from end-users and champions to procurement leaders and C-suite executives. Position yourself as a trusted advisor at every level, rather than just a vendor.

• Complex Deal Navigation: Confidently manage lengthy, multi-stakeholder sales cycles. Coordinate internal resources — including Solutions Engineering, Legal, Finance, and Leadership — to advance deals and close them on schedule.

• Pipeline Generation: Create and manage outbound campaigns that consistently populate your pipeline with qualified enterprise opportunities. Don’t wait for inbound leads; generate your own momentum.

• Cross-Functional Collaboration: Work closely with Customer Success, Implementation, Marketing, and Product teams to provide a seamless experience, while also integrating the voice of the enterprise customer back into the business to enhance our product and go-to-market strategies.

⛳️ Requirements

• 6+ years of experience in a quota-carrying enterprise Account Executive role within a SaaS or B2B technology setting, with a proven track record of securing new logos and expanding accounts at the 5,000+ employee level. Consistent achievement at or above quota is essential.

• In-depth understanding of enterprise purchasing cycles, procurement procedures, and the complexities of selling to large organizations. Familiarity with SaaS business models, expansion strategies, and multi-year contract frameworks is crucial.

• Expert-level command of structured enterprise sales methodologies — such as MEDDPICC, Challenger, or similar. You can navigate complex deals, identify risks early, and maintain control over a protracted buying process involving multiple stakeholders.

• Ability to comprehend, demonstrate, and articulate intricate product features within the context of enterprise workflows. Experience in selling productivity, collaboration, or communication tools is a significant advantage.

• AI Fluency: You don’t just utilize AI tools — you proactively explore innovative ways to leverage them. You harness AI to expedite research, personalize outreach on a large scale, synthesize account insights, and refine your commercial acumen.

• Outstanding negotiation, communication, and executive presence. You can command attention in a room with both a VP of Engineering and a CFO present. You exhibit curiosity, organization, and an unwavering focus on advancing deals while preserving relationships.

🏝️ Benefits

• Excellent health care options (including a comprehensive range of medical, dental, vision, mental health, and fertility benefits)

• Disability and life insurance options

• 401(k) and RRSP matching

• Paid parental leave

• Twenty days of paid time off annually, eleven paid holidays per year, and unlimited sick days

• Home office stipends

• Caregiver and pet care stipends

• Wellness stipends

• Admission discounts

• Opportunities for learning and development