Founding Account Executive

About Keep Company

Keep Company is on a mission to make human connection an intentional, scalable asset in every workplace. As a venture-backed SaaS platform recognized by Techstars, Forbes, and SHRM, our patented talent platform delivers transformative relationship-based development experiences at leading professional services organizations.

With our platform, talent leaders can launch, scale and measure innovative programs, including mentoring, coaching and ERGs, with little admin burden and maximum impact. We’re proud to support 20+ clients in professional services - with zero churn and multiple six-figure contracts. At a time when artificial intelligence is rapidly reshaping how we work, Keep Company is rebuilding the human layer of work, because we believe people are the most important asset that organizations can invest in to strengthen culture, retention, and performance in the moments that matter most.
 

The Role

As a Keep Company Founding Account Executive (we're hiring two at once), you will drive new business in the mid-market segment through prospecting, deal and pipeline management, and closing. You will be part of an elite, professional, and rapidly growing team that succeeds through collaboration, tenacity, and constant improvement.

This is Keep Company's first sales hire, which means you're not just filling a role- you're building the foundation. You'll work directly with the CEO to turn early traction into repeatable revenue and establish the sales motion that future hires will learn from. This isn't for someone who needs structure handed to them. It's for someone who thrives creating it.

Compensation

On target earnings of $225K+ uncapped annually (60% base, 40% variable) plus equity.

Benefits

Our culture is fueled by ambitious people dedicated to our mission. We have thoughtfully structured our PTO policy to account for the needs of our team to take care of themselves and their families while also taking care of business. Operating in alignment with our values, including Keep Your Commitments and Keep Yourself, allows us to provide the team flexibility when necessary and also encourages real breaks for restoration when needed.

Vacation: 10 Days
Personal Days: 5 Days
Care Leave: 5 Days
Sick Days: 5 Days
Federal Holidays: 10 Days
End of Year Shutdown: December 21, 2026  - Jan 1, 2027 (Exact dates adjusted each year)

We offer a 401(k) plan with a maximum annual employee contribution of $6,000.  We also pay 100% of the premium for one of our medical plans (and also offer dental and vision).

Location

In person three days a week (Monday, Tuesday, and Thursday) in our downtown Bethesda, MD office.  Work remotely on Wednesday and Friday.  This is how you'll be able to shadow the CEO (your future manager) and learn how she has been selling up until this point.

Responsibilities

• Engage prospects at a senior executive level (Chief Human Resource Officers, Chief Talent Officers, and Directors of Professional Development) to pursue and close new customers in the legal and professional services sectors
• Conduct outbound prospecting to fill your pipeline with qualified sales opportunities as well as handling inbound opportunities
• Tightly manage all prospects through the sales funnel in Hubspot
• Consistently achieve revenue targets by applying modern sales techniques and processes to efficiently manage sales opportunities through your funnel to a successful close
• Partner directly with the CEO to build and refine the sales motion, including processes, language, and playbooks
• Use your creativity and tenacity to develop and improve how we target and penetrate new market segments

What You Bring

Skills & Attributes

• You're a hunter: Net new logos are your scorecard and you build the pipeline yourself
   
• You're gritty: You know what it means to grind through a long, complex cycle with a skeptical buyer and come out the other side with a signed contract
   
• You're sharp and curious: You grasp complex concepts quickly, ask better questions than anyone in the room, and genuinely want to understand why - why the prospect is in pain, why a deal stalled, why something worked
   
• You own your outcomes: Good quarter or bad, you know exactly what happened and why. You don't make excuses. You make adjustments
   
• You're coachable: You take feedback well - not because you're passive, but because you're wired for constant improvement. 
• You read the room: You're self-aware, politically sharp, and keenly attuned to how you're being perceived. You know when to push, when to pause, and when to bring in a champion

Required Experience 

• 5+ years of B2B sales experience in a hunting role focused on net new business
• 2+ years of experience selling complex software solutions with multi-month sales cycles
• Demonstrable track record of above-target performance, especially in a startup or early-stage environment
• Experience earning access to and influencing senior executive buyers

Nice to Have

• Some traditional sales training (you know what good process looks like) with real startup DNA (you know how to move without a playbook)
• 4-year degree from a credible institution with strong performance, or equivalent real-world experience
• Solid extracurricular track record in sports, leadership, performance, i.e., something that shows you know how to compete

Why Keep Company

• Earn uncapped commission as you sell a new and disruptive technology into a huge market.  Competitive compensation and an opportunity for advancement - a true meritocracy where performance is recognized and rewarded.
• A direct line to the Founder + CEO and real influence over how this company goes to market
• A fast-paced and collaborative environment where we leverage the latest technology and keep getting better
• An opportunity as an early team member to help shape the direction and culture of the company
• Comprehensive benefits: Health (medical, dental & vision) and 401(k) with a maximum employee contribution of $6K.

How to Apply 

Some candidates may see the list above and feel discouraged because they don't match all the items. The data says this is especially true of traditionally underrepresented communities. Please apply anyway: there's a good chance you have valuable skills. We are committed to building an equitable environment, and we're taking steps to meet that commitment. 

If you're excited about making a tangible impact in a mission-driven organization and across the working world, we'd love to hear from you.

Apply here by sending your resume and a cover letter sharing what excites you about building at the intersection of tech and human connection.