Enterprise Account Executive: Legal AI, Pilots & Growth

Tavrn; San Francisco (CA); Hybrid; USD 240,000 - 420,000; Full time

Benefits offered by this job

OTE $320K

Uncapped commissions

Medical, dental, and vision benefits

Greenfield enterprise territory

Pilot-first sales motion

Promote-from-within track record

Executive deal support

Job summary

Tavrn is hiring an Enterprise Account Executive to sell into top plaintiff personal injury firms. You will own a named territory, run pilots against firm records, and close multi-year agreements with firm owners and executives. Expect 25-40% travel as you cover enterprise opportunities and expand with customers.

You will manage pilots, structure deals, and coordinate with Customer Success to expand into additional case services, backed by an executive sponsor for strategic deals.

Qualifications

• 5+ years in B2B software sales, including at least 3 in a closing role carrying an enterprise quota.
• Track record closing deals with six-month-plus cycles and multiple stakeholders.
• Expert command of Pipeline Generation (PG) as this is a new logo hunting role.
• Experience running structured pilots or proofs of concept, not only demos.
• Comfortable building a territory from a target list and a hypothesis rather than inheriting one.
• Exceptional discovery skills and the discipline to be measured weekly.

Responsibilities

• Own a named enterprise territory end to end, from first touch through pilot, close, and expansion.
• Run structured pilots against the firm's own records, with success criteria agreed in writing before kickoff.
• Sell case economics to firm owners and COOs: case duration, cash flow timing, and throughput per staff member.
• Structure multi-year agreements with ramped pricing rather than annual seats.
• Maintain accurate pipeline and forecast in HubSpot, and hold your calls in weekly review.
• Represent Tavrn at industry conferences and on-site client meetings (25-40% travel).
• Partner with Customer Success on clean handoff, and expand accounts from record retrieval into case services.

Skills

B2B software sales

Enterprise sales

Pipeline generation

Stakeholder management

Travel readiness

Tools

HubSpot

Job description

About Tavrn: Tavrn is a pioneering legal AI company transforming the plaintiff law sector

through automation of medical chronologies, demand letters, and medical record retrieval. We

are dedicated to becoming the leading AI-driven solution provider for personal injury, medical

malpractice, workers' compensation, SSDI legal practices, and beyond.

Position Overview: We're hiring Enterprise Account Executives to sell into the largest plaintiff

personal injury firms in the country. You will own a named territory, run pilots against the firm's

own records, and close multi-year agreements with firm owners, COOs, and CTOs. Revenue

has grown four consecutive quarters and pilots convert quickly, so this role is about coverage

and execution rather than proving the category exists. Territories here are built, not inherited,

and the enterprise segment is still largely unworked.

Key Responsibilities:

• Own a named enterprise territory end to end, from first touch through pilot, close, and expansion.

• Run structured pilots against the firm's own records, with success criteria agreed in writing before kickoff.

• Sell case economics to firm owners and COOs: case duration, cash flow timing, and throughput per staff member.

• Structure multi-year agreements with ramped pricing rather than annual seats.

• Maintain accurate pipeline and forecast in HubSpot, and hold your calls in weekly review.

• Represent Tavrn at industry conferences and on-site client meetings (25-40% travel).

• Partner with Customer Success on clean handoff, and expand accounts from record retrieval into case services.

Qualifications:

• 5+ years in B2B software sales, including at least 3 in a closing role carrying an enterprise quota.

• Track record closing deals with six-month-plus cycles and multiple stakeholders.

• Expert command of Pipeline Generation (PG) as this is a new logo hunting role.

• Experience running structured pilots or proofs of concept, not only demos.

• Comfortable building a territory from a target list and a hypothesis rather than inheriting one.

• Exceptional discovery skills and the discipline to be measured weekly.

• Experience selling to law firms, healthcare, or insurance is a plus, not a requirement.

• Willingness and ability to travel regularly.

What We Offer:

• Competitive compensation with an OTE of $320K

• Uncapped commission with accelerators above quota

• Comprehensive medical, dental, and vision benefits

• A greenfield enterprise territory in a segment that is still largely unworked.

• A pilot-first sales motion converting quickly, with four consecutive quarters of company revenue growth.

• A documented promote-from-within track record.

• Executive support on strategic deals, including direct CEO sponsorship.

Join Tavrn and help revolutionize the legal industry through AI-driven solutions!