Enterprise Account Executive

  • Anywhere

CARET brings the latest in technology and automation to over 10,000 legal and accounting firms, empowering highly skilled professionals to refocus their expertise on what truly matters. CARET harnesses powerful and secure practice management, document automation, and payment processing to take firms, professionals, and their clients further.

Our team-defined values guide how we show up for each other, for our partners, and for our customers:

  • We succeed together
  • We embrace progress
  • We care big
  • We create space

To join our remote-first, engage from anywhere team, visit getcaret.com/careers.


  • Minimum 5+ years of direct new business quota carrying experience selling enterprise software as an Account Executive.  You’ve held a quota of at least $1 million dollars for Net New Business across multiple years in the past.
  • Proven. Backed by a track record of proven success, including selling at the enterprise level, consistent quota achievement and landing new logos.
  • Team Player. No lone wolves, we win and celebrate as a team here at CARET Legal.
  • Self-Motivated & driven. Possess a hungry, high energy, “roll-up-your-sleeves” mentality.
  • Self-Starter.  You know what it takes to develop relationships and find creative ways to break into new accounts/expand at your customers.  
  • Problem Solver. You don’t stop when you encounter a challenge and instead find a way to overcome the obstacle and find success.
  • An Effective Presenter. Experienced delivering in-person presentations to multiple audiences.
  • Tenured. Displays loyalty and perseverance through long, stable job tenure and positive career trajectory.
  • Consultative. A trusted advisor to both customers, colleagues and partners.
  • Grit, Tenacity, and Curiosity


  • Selling to Legalkey accounts operating as a hunter and farmer.
  • Navigating an opportunistic greenfield territory, top of funnel activity & outbound prospecting, while also nurturing accounts through a “land and expand” approach.
  • Experience navigating a complex sales cycle (6-9 months) from start to finish, leveraging internal and external resources across CARET Legal, the customer and partner ecosystems.
  • Comfortable speaking to senior executives (c-suite and business partners) and strong presentation skills for delivering in-person and virtual presentations.
  • Flawless execution when performing discovery, to build out ROI and quantifiable business cases that map challenges and expected value with CARET Legal capabilities.
  • A trusted advisor to both customers and colleagues to leverage multiple stakeholders throughout complex deals.
  • Actively seeking to understand industry trends to help position against competitors.
  • Prior experience selling to Financial Services, Legal and Insurance companies is a plus
  • Experience selling ERP / Backend


  • Flexible PTO
  • Summer Fridays
  • No meeting Fridays
  • Medical, Dental, Paid Sick Days, Vision, and Supplemental Coverage
  • Flexible Spending Account
  • Health Savings Account
  • 401(k) match

Equal Employment Opportunity: CARET is an Equal Opportunity, Affirmative Action Employer.

Actual base pay will depend on varying circumstances, including the position, location, individual qualifications, market finances, and other operations business needs.

Depending on the position, compensation may also include commission, bonuses, etc. Potential for bonuses is based on company performance and potential for merit increases is based on performance.