Commercial (Mid-Market) Account Executive at Grammarly

About Superhuman Superhuman Mail is now part of Superhuman, the AI productivity platform on a mission to unlock the superhuman potential in everyone. The Superhuman suite of apps and agents brings AI wherever people work, integrating with over 1 million applications and websites. The company’s products include Grammarly’s writing assistance, Coda’s collaborative workspaces, Mail’s inbox management, and Go, the proactive AI assistant that understands context and delivers help automatically. Founded in 2009, Superhuman empowers over 40 million people, 50,000 organizations, and 3,000 educational institutions worldwide to eliminate busywork and focus on what matters. The Opportunity As a Commercial (Mid-Market) Account Executive, you will drive Superhuman Mail's upmarket expansion by executing strategic, value-based selling to Mid-Market organizations while consistently achieving higher average contract values through comprehensive solution selling and multi-threaded relationship building. • Drive Superhuman's upmarket expansion by consistently achieving higher average contract values through strategic deal structuring and comprehensive solution selling. • Navigate complex sales cycles with Mid-Market organizations, managing multiple stakeholders and approval processes. • Execute a value-based selling approach, positioning Superhuman's solutions based on customer impact and ROI. • Build advocates and cultivate multi-threaded relationships at senior levels, including C-Level and VP. • Own pre-sale contract conversations and negotiations. • Experiment with new processes and adapt to changing customer environments. • Collaborate with cross-functional teams (Sales Development, Customer Success, Sales Engineering, Product) to achieve sales outcomes. • Develop strategic account plans to ensure customer success and growth. • Maintain a high level of rigor in pipeline management, forecasting, and account planning. • Develop and execute outbound sales strategies specifically tailored to Mid-Market accounts to identify and engage new prospects. Qualifications • Mid-Market Sales Expertise: 5+ years closing five- and six-figure B2B SaaS deals with mid-market organizations (500–1,500 employees), consistently exceeding quota. Skilled at selling comprehensive solution bundles and navigating complex, multi-threaded sales cycles with C-level and VP stakeholders. • Value-Based Selling & Sales Methodology: Proven success positioning solutions around customer impact and ROI using structured frameworks (e.g., MEDDICC, Challenger Sale) to systematically qualify opportunities and drive predictable outcomes. • Relationship Builder & Executive Presence: Adept at creating advocates within prospect organizations, building consensus across diverse stakeholders, and serving as a trusted advisor to senior leadership. • Operational Rigor: Disciplined in forecasting, pipeline management, and CRM hygiene. Uses data to generate insights and deliver reliable forecasts that leadership can count on. • Excellent Communicator & Cross-Functional Collaborator: Distills complexity into clear messaging across mediums. Partners effectively with Sales Development, Customer Success, Sales Engineering, and Product teams in a remote-first environment. • Bias to Action & Strategic Thinking: Takes prompt, thoughtful action in ambiguity while developing comprehensive account plans and long-term partnership strategies. Self-directed and thrives managing multiple priorities in fast-paced environments. • AI Enthusiast & Bar Raiser: Passionate about leveraging AI to increase productivity and impact. Committed to elevating team standards and helping others grow. Compensation and Benefits Superhuman offers all team members competitive pay along with a benefits package encompassing the following and more: • Excellent health care (including a wide range of medical, dental, vision, mental health, and fertility benefits) • Disability and life insurance options • 401(k) and RRSP matching • Paid parental leave • 20 days of paid time off per year, 12 days of paid holidays per year, two floating holidays per year, and flexible sick time • Generous stipends (including those for caregiving, pet care, wellness, your home office, and more) • Annual professional development budget and opportunities Superhuman takes a market-based approach to compensation, so base pay may vary by location. Our US locations are categorized into two compensation zones based on proximity to our hub locations. Base pay may vary considerably depending on job-related knowledge, skills, and experience. The expected salary ranges for this position are outlined below by compensation zone and may be modified in the future. The expected “On Target Earnings” (OTE) for this role are outlined below and may be modified in the future. United States: Zone 1: $200,000 – $230,000 OTE/year (USD) Zone 2: $190,000 – $220,000 OTE/year (USD) Commissions are 40% of total sales. The market-based compensation differentials will be applied only to base pay for commission-eligible team members. We Encourage You to Apply At Superhuman, we value our differences, and we encourage all to apply—especially those whose identities are traditionally underrepresented in tech organizations. We do not discriminate on the basis of race, religion, color, gender expression or identity, sexual orientation, ancestry, national origin, citizenship, age, marital status, veteran status, disability status, political belief, or any other characteristic protected by law. Superhuman is an equal opportunity employer and a participant in the US federal E-Verify program (US). We also abide by the Employment Equity Act (Canada). #LI-Remote