Founding Account Executive

Keep Company•Bethesda, MD

41d•Hybrid

About The Position

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.

Requirements

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
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

Nice To Haves

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

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

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).
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.