Enterprise Account Executive, Grammarly
$207-300k
OTE
Salary varies depending on location. Commissions are 40% of total sales. The market-based compensation differentials will be applied only to base pay for commission-eligible team members
AI-powered writing assistant
Be an early applicant
AI-powered writing assistant
1001+ employees
Be an early applicant
$207-300k
OTE
Salary varies depending on location. Commissions are 40% of total sales. The market-based compensation differentials will be applied only to base pay for commission-eligible team members
1001+ employees
Company mission
Grammarly's mission is to improve lives by improving communication.
Role
Who you are
- 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
What the job involves
- 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
- 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
- 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
- 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
Our take
From professional writing to everyday correspondence, effective communication is critical. Grammarly is an AI-powered writing assistant that helps people write clearly and without mistakes, checking spelling, grammar, and other potential pitfalls.
Grammarly was originally launched as a subscription service for students, although the platform has moved into the mainstream in the last decade. It went freemium in 2015 and now works across more than 500,000 applications and websites, including email clients, enterprise software, and word processors. Paid tiers give users more tools beyond grammar and spelling checks, including things like word choice, sentence rewrites, tone adjustments, fluency, and formality level.
The company has been profitable since the beginning and now has a valuation of more than $13 billion, placing it among the 10 most valuable startups in the US. The AI writing assistant space is heating up, and Grammarly is hoping to defend its position against offerings including Scalenut, Ginger and Microsoft's Editor by the release of its SDK, making it far easier to integrate Grammarly into other applications. So far, this has been used in over 4,000 products and earned excellent ratings and increased user numbers of Grammarly's service.
Steph
Company Specialist at Welcome to the Jungle
Insights
44% employee growth in 12 months
Company
Funding (last 2 of 3 rounds)
Nov 2021
$200m
LATE VC
Oct 2019
$90m
LATE VC
Total funding: $400m
Company benefits
- Support for professional development with training, coaching, and regular feedback
- Global, local, and team-specific events and programs
- Catered lunches
- Gym and recreation stipends
- Admission discounts
- Work from home opportunities
- Medical, dental, vision, financial, and other benefits, as well as equity
- Support to set up a home office
- Ample and defined time off
- 401(k) matching
Company HQ
Financial District, San Francisco, CA
Leadership
Alex Shevchenko
(Co-Founder & Board Member)Studied at Vienna's International University before receiving an MBA from the University of Toronto. Co-founded MyDropBox.com in 2006. The company was bought by Blackboard Inc. three years later. Co-founded Grammarly in 2009.
Max Lytvyn
(Co-Founder & Board Member)Studied for an MBA at Vanderbilt University before joining Blacboard Inc. as Director of Product Strategy in 2007. Was General Manager and then Partner at Sciworth Labs from 2004 to 2013. Was a Board Member at Uniweb and invested in farmland investment platform FarmTogether.
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