Founding Account Executive - Remote AI LegalTech SaaS

Trailmate, Inc.; United States; On-site; USD 100,000 - 150,000; Full time

Benefits offered by this job

Competitive base salary

Uncapped commission

Meaningful equity

Job summary

Trailmate, Inc. seeks a Founding Account Executive (AE) to spearhead sales in their innovative AI-native legal tech startup. As the first AE, your contributions will directly shape the company's revenue trajectory while fostering relationships in the legal industry.

This full-time role includes running the entire sales cycle, collaborating closely with the founder, and crafting sales playbooks. Ideal candidates possess 3-6 years of SaaS closing experience and an entrepreneurial mindset.

Qualifications

• 3–6 years of closing experience in SaaS, preferably in startup or legaltech.
• Comfort selling into professional services firms, especially law firms.
• Desire to shape a company from the ground up.

Responsibilities

• Run the full sales cycle: prospecting, demo, pilot, close.
• Refine messaging, pricing, and go-to-market strategy with the founder.
• Partner with customer success to ensure smooth implementations.

Skills

Closing experience in SaaS

Strong track record of hitting/exceeding quotas

Excellent communication skills

Job description

Trailmate, Inc. seeks a Founding Account Executive (AE) to spearhead sales in their innovative AI-native legal tech startup. As the first AE, your contributions will directly shape the company's revenue trajectory while fostering relationships in the legal industry.

This full-time role includes running the entire sales cycle, collaborating closely with the founder, and crafting sales playbooks. Ideal candidates possess 3-6 years of SaaS closing experience and an entrepreneurial mindset.