Location: Miami, FL

Department: Customer Success

Employment Type: Full-Time

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.

About Our Customer Success Team

Our Customer Success team owns the entire post-sale relationship. From the moment a Customer signs, we're the ones making sure they see value fast, get unstuck when they hit a wall, and never feel like they're shouting into the void. We build the help content that answers questions before they're asked, and we hold ourselves to real, visible metrics: resolution time, handle time, and Customer happiness, because outcomes are how we know we're doing our job.

What You Will Do

This is a broad, hands-on role covering the full post-sale Customer journey. You'll lead onboarding walkthroughs, triage and resolve support tickets, get ahead of issues before they escalate, and build the Customer-facing help material that scales our support. You'll also own key support metrics including resolution time, handle time, and more, and use them to keep raising the bar. This role leans technical, so you should be comfortable digging into data, working alongside AI tools every day, and understanding how the pieces of our product fit together. Comp includes a quarterly variable component, so strong, consistent performance shows up in your paycheck every quarter, not just once a year.

Key Responsibilities

• Post-Sale Onboarding: Lead onboarding walkthroughs for new Customers, setting them up for a fast, confident start with Gail.
• Ticket Triage & Resolution: Serve as the front line for Customer questions, triaging, troubleshooting, and resolving tickets quickly and clearly.
• Proactive Support: Spot friction before it becomes a ticket. Reach out, flag risk, and get ahead of issues rather than waiting for them to land in your queue.
• Help Content & Documentation: Create and maintain Customer-facing help docs, guides, and knowledge-base articles that let Customers help themselves.
• Metrics Ownership: Own and report on resolution time, handle time, and other support quality metrics, and use them to drive continuous improvement.
• Cross-Functional Collaboration: Partner with sales, product, and engineering to surface Customer feedback and shape what we build next.
• Documentation & Reporting: Keep accurate records of Customer interactions in our CRM (HubSpot) and provide regular updates on account and support health.

What You Will Need

• Experience: 2+ years in Customer success, support, or account management, preferably in B2B SaaS.
• Customer-Centric Mindset: A proven track record of building trust and solving problems for Customers, even under pressure.
• Strong Writer: Comfortable turning complex product knowledge into clear, Customer-facing help docs and guides.
• Analytical Skills: Able to interpret metrics like resolution time and handle time and use them to inform how you work.
• Communication Skills: Excellent verbal and written communication, with a knack for simplifying complex concepts.
• Tech-Savvy: Familiarity with CRM systems (HubSpot) and Customer success platforms.
• SQL: Working knowledge of SQL preferred, so you can pull and interrogate Customer data yourself instead of waiting on someone else.
• AI Fluency: You work with Claude or ChatGPT on a daily basis to automate processes and take the repetitive work off your own plate.
• Software Fundamentals: A solid grasp of software basics, including how APIs work and how systems talk to each other.
• Problem-Solving Skills: Resourceful and proactive. You go find the fix rather than wait for the escalation.
• Team Player: Collaborates well across sales, product, and support in a fast-paced environment.

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.

What We Offer

• Competitive base salary plus quarterly variable and equity compensation to share in our success.
• Unlimited PTO to prioritize work-life balance and recharge.
• Comprehensive health, dental, and vision insurance options.
• Opportunities for professional development and career growth.
• A fast-paced in-person office culture in Miami.