Financial Services AI for Earth and Beyond

Gail offers a suite of AI tools built specifically for financial services. Our AI agents and GPTs support hundreds of banks, lenders, insurers, and BPOs across the USA and nearly a dozen other countries. Gail does this by automating workflows, providing insights, and managing conversations of all kinds via voice, sms, webchat, and whatsapp. We’re building the operating system that will one day power financial services across earth, and eventually the galaxy.

Gail is HQ’d in Miami, and is backed by Founders Fund, Khosla Ventures, and many of the best technology investors in the world. We’re seeking obsessives looking to practice their privilege to be ambitious.

The Role

Gail offers the most advanced conversational AI agents, GPTs, workflows, and analytics tools for the financial services industry—serving banks, insurers, and many of the world's largest businesses. Account Executives will own the full sales cycle for the Gail suite—from first outreach to closed-won—running your own book, managing inbound, generating pipeline, delivering demos, and moving fast to turn prospects into Customers. This is a high-velocity sales role supporting our small to mid size businesses

The role comes with tremendous autonomy, a fast pace in person office culture (in Miami), and top decile compensation—which includes uncapped commission, bonus, benefits, and equity.

What You Will Do

• Own the full sales cycle for our Gail agent products, catering to small-to-mid size businesses
• Manage inbound leads, while also generating your own pipeline through outbound outreach, and referrals
• Run sharp, tailored demos of Gail for insurance agencies, lenders, banks, and fintechs, translating their pain points into clear value
• Move deals quickly through the funnel with disciplined follow-up and a bias toward speed
• Consistently hit and exceed monthly and quarterly revenue targets
• Qualify prospects rigorously and prioritize the accounts most likely to close and succeed on Gail
• Partner with the Account Management team for a smooth handoff at close, setting new Customers up for long-term success
• Maintain accurate records of all deal activity and pipeline in HubSpot, ensuring full visibility across teams
• Bring market and prospect feedback back to Product and Marketing to sharpen our messaging and roadmap

What You Will Need

• 2-4 years of experience in a closing sales role (AE, inside sales, or similar) at a SaaS or technology company
• A proven track record of hitting and exceeding quota in a high-velocity, transactional sales environment
• Strong communication and relationship-building skills; you can translate technical concepts into clear, compelling value
• A fast-moving, self-starter mindset; you generate your own pipeline and don't wait for leads to find you
• Hands-on experience with HubSpot or a similar CRM
• Comfort selling into SMB accounts with short sales cycles and high deal volume

Bonus points for:

• Experience selling into or working within financial services (banking, insurance, lending), insurtech, or fintech
• Familiarity with AI-powered products or voice technology
• Experience closing high volume inbound and fast paced sales

Technologies You'll Use

• CRM & Sales Tools: HubSpot, Google Workspace
• Communication: Apollo, Slack, Email
• Reporting: Google Sheets, internal dashboards, pipeline & sales reporting tools

Benefits

• Comprehensive health, dental, and vision coverage
• Flexible PTO policy
• Professional development stipend
• Team events and a high-energy, collaborative office culture
• A front-row seat to reshaping how an entire industry operates

In-Office Policy

We believe the best ideas happen when great people are in the same room. Our Miami office is where culture is built, collaboration thrives, and the energy that makes Gail special comes to life. Team members in the Miami area will be expected to be in office five days a week.

Equal Opportunity Employer

Gail is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, veteran status, or any other characteristic protected by applicable law.