Head of Sales

San Francisco / Los Altos, in-person 5 days a week · Reports to the CEO · $200K to $250K base · $400K to $500K OTE + equity

About Uare.ai

Uare.ai builds AI for businesses where the expertise is the product: coaches, consultants, tutors and educators, and accounting and tax firms. A professional captures how they think, speak, and work, and Uare.ai turns it into their own AI. That AI runs the client work they can't scale on their own: client intake and document collection, courses and tutoring that adapt to each student, answering client questions in the expert's voice, and paid services clients can buy directly.

Customers today include accounting and tax firms, education programs, coaching and advisory practices, and enterprise training teams. Professionals start at $199.99 a month, and organizations get multiple workspaces, pooled Credits, and team roles.

We launched publicly in July 2026. Founder and CEO Rob LoCascio took LivePerson from startup to public company selling to global enterprises. He has built a sales engine before and wants a partner to build this one. Backed by $10.3M from Mayfield and Boldstart Ventures.

About the role

You will turn early demand into a repeatable revenue engine. Today the founders close every deal. You will carry the number first, then hire and run a young team of SDRs that scales it.

What you'll do

• Own new revenue.
• Founder-led service businesses first (coaches, consultants, tutors, accounting and tax practices), then education and enterprise training teams.
• Build the playbook.
• ICP, qualification, pricing, and contracts, from first touch to close.
• Close deals yourself while the team is small.
• Build the team.
• Hire and manage a team of about four SDRs, and own the forecast.
• Close the loop.
• Tell product what buyers want and why we lose.

What we're looking for

• 8+ years in B2B sales, carrying and beating a quota.
• Built a sales team from zero at an early-stage company.
• Sold to SMB and enterprise buyers.
• Comfortable selling a new category, where you teach before you sell.
• Results you can verify.
• Bonus
• Sold to services firms, agencies, schools, or L&D teams.
• AI or vertical SaaS experience.
• How we hire
• We hire for a growth mindset: outcomes over output, experiments by default, and moving the metric that matters.
• Location: in-person, 5 days a week, across our San Francisco and Los Altos offices.
• Uare.ai is an equal opportunity employer. We welcome people of every background and do not discriminate on the basis of race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, veteran status, or any other protected characteristic.
• The expected base compensation for this position is below. Our total compensation package for full-time employees includes equity and a comprehensive benefits package.