Enterprise 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 Role As an Enterprise Account Executive for Superhuman Mail, you will own the full revenue motion for companies with 5,000+ employees — from first meeting to signed contract, and from initial deployment to expanded footprint. You are both a hunter and a farmer: winning new enterprise logos while simultaneously growing the accounts you’ve already landed. Enterprise deals are complex, multi-stakeholder, and high-stakes. You’ll navigate procurement, legal, IT, and the C-suite while keeping momentum and closing with precision. You’ll partner closely with Solutions Engineering, Customer Success, and Implementation to deliver a world-class buying experience that sets the foundation for long-term, compounding growth. What You’ll Do • New Logo Acquisition: Own the full sales cycle for net-new enterprise accounts — from prospecting and pipeline generation through to contract close. Build and execute targeted outbound strategies to penetrate 5,000+ employee organizations, engaging multiple stakeholders across departments and levels. • Account Expansion: Grow revenue within your landed enterprise accounts through strategic upselling and cross-selling. Identify whitespace, build expansion plans in partnership with Customer Success, and drive adoption that converts initial deployments into company-wide rollouts. • Renewal Management: Ensure on-time renewals by consistently demonstrating value and ROI, proactively identifying and mitigating churn risks, and building retention strategies that protect and grow the base. • Executive Relationship Management: Build deep, multi-threaded relationships across your accounts — from end-users and champions to procurement leaders and C-suite executives. You are a trusted advisor at every level, not just a vendor. • Complex Deal Navigation: Manage long, multi-stakeholder sales cycles with confidence. Coordinate internal resources — Solutions Engineering, Legal, Finance, Leadership — to move deals forward and close on time. • Pipeline Generation: Develop and own outbound campaigns that consistently fill your pipeline with qualified enterprise opportunities. You don’t wait for inbound; you create your own momentum. • Cross-Functional Collaboration: Partner closely with Customer Success, Implementation, Marketing, and Product to deliver a seamless experience — and bring the voice of the enterprise customer back into the business to improve our product and go-to-market. What You’ll Bring • 6+ years in a quota-carrying enterprise AE role within a SaaS or B2B technology environment, with a demonstrated track record of closing net-new logos and expanding accounts at the 5,000+ employee level. Consistent attainment at or above quota required. • Deep understanding of enterprise buying cycles, procurement processes, and the dynamics of selling into large, complex organizations. Familiarity with SaaS business models, expansion motions, and multi-year contract structures. • Expert-level proficiency in structured enterprise sales methodologies — MEDDPICC, Challenger, or equivalent. You can map a complex deal, identify risk early, and maintain control of a buying process that spans months and many stakeholders. • Ability to understand, demo, and articulate complex product features in the context of enterprise workflows. Experience selling productivity, collaboration, or communication tools is a strong plus. • AI Fluency: You don’t just use AI tools — you actively seek ways to work with them that others haven’t tried yet. You leverage AI to accelerate research, personalize outreach at scale, synthesize account signals, and sharpen your commercial instincts. • Exceptional negotiation, communication, and executive presence. You can command a room with a VP of Engineering and a CFO in the same meeting. You’re curious, organized, and relentlessly focused on moving deals forward without sacrificing the relationship. How We Measure Success • New Logo ARR: Net-new ARR closed from enterprise accounts • Expansion ARR: ARR growth from upsell and cross-sell within the book • Net Revenue Retention (NRR): Health and growth of the overall enterprise base • Renewal Rate: On-time renewal % across your accounts • Pipeline Coverage: Consistent, qualified enterprise pipeline at the required multiple • Quota Attainment: Overall performance against combined new logo + expansion targets Why This Role, Why Now Enterprise is the next frontier for Superhuman Mail. We’ve built a product that professionals genuinely love — and we’re now taking that into the most complex, highest-value accounts in the world. This role is an opportunity to define how Superhuman shows up in the enterprise, build the playbook from scratch, and close the kinds of deals that transform a company’s trajectory. You’ll do it alongside a team that raises the bar every day, backed by a product and a brand that makes the conversation easier before you even show up. 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 • Twenty days of paid time off per year, eleven days of paid holidays per year, and unlimited sick days • Home office stipends • Caregiver and pet care stipends • Wellness stipends • Admission discounts • Learning and development opportunities Superhuman takes a market-based approach to compensation, which means base pay may vary depending on your location. Our US locations are categorized into two compensation zones based on proximity to our hub locations. United States: takes a market-based approach to compensation, which means base pay may vary depending on your 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 “On Target Earnings” (OTE) for this role are outlined below and may be modified in the future. Zone 1: $230,000 – $300,000 OTE/year (USD) Zone 2: $207,000 – $270,000 OTE/year (USD) Commissions are 50% 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).