Commercial Account Executive, Superhuman Mail — Grammarly

Superhuman offers a dynamic hybrid model, and candidates in this role can be based remotely. You may be expected to travel to meet in person during your team’s scheduled collaboration weeks. Managers will determine in-person time according to business needs. This hybrid approach helps foster trust, innovation, and a strong team culture, with the flexibility of working from home, whenever you need focus time. About Superhuman Grammarly 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, Superhuman Docs'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. Learn more at superhuman.com and about our values here. 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: 3+ years closing five- and six-figure B2B SaaS deals with mid-market organizations (250 - 4,999 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. - 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: $178 - $264k 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).

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...

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