Flex is a growth-stage, NYC headquartered FinTech company that is creating the best rent payment experience. It’s hard to believe that it’s 2026 and paying rent on time is expensive, inflexible, and difficult. We’re here to change that! Flex enables our users to pay rent throughout the month on a schedule that better fits their finances and budget. Our mission is to empower as many renters as possible with flexibility over their most significant recurring expense. After deliberately keeping a stealth profile as we built up unprecedented investor support and an enthusiastic user base, we are looking for motivated individuals to help us keep our mission growing. Will you be a part of the team?
About the role
We're hiring a Lead, CS AI Content to own the content layer that powers Flex's AI-driven customer support tools.
This role sits at the intersection of content, conversational AI, and support operations. You'll build and maintain structured, machine-readable content that enables AI systems to respond accurately, take action through APIs, and safely support customers across channels.
You'll play a key role in conversational AI by authoring dialogue flows, maintaining decision trees, and ensuring safe, accurate customer experiences. The content you produce directly impacts containment, CSAT, and risk prevention.
What you’ll do
- Write and maintain AI-native content across chatbot, voicebot, and agent assist tools, including structured responses, decision trees, and escalation logic.
- Author conversational AI dialogue flows, including multi-turn interactions, clarifying questions, and safe handoffs to human support.
- Improve AI workflows by working with API-connected tools, helping ensure AI can retrieve data, trigger actions, or route conversations appropriately.
- Keep content and configurations current across all AI tools — ensuring chatbot, voicebot, and agent assist are consistently optimized and aligned as products, policies, and workflows evolve.
- Identify gaps in SOPs and support documentation that limit AI accuracy and flag them for resolution.
- Update SOPs and internal documentation to reflect product changes, policy updates, and evolving AI workflows — keeping content accurate and agent-ready.
- Disambiguate overlapping or ambiguous concepts to improve AI reasoning and response quality.
- Drive content for cross-functional launches as new AI tools or capabilities roll out.
- Maintain version-controlled AI training content that is audit-ready and aligned with policy and regulatory requirements.
- Monitor chatbot and voicebot analytics to identify underperforming flows, containment gaps, and content issues — and surface or address them based on priority.
Key qualifications
- Experience in Customer Success or Support, Content Operations, Trust & Safety, QA, or similar fields.
- Hands-on experience with conversational AI or AI-powered support tools.
- Experience working with systems and workflows that interface with automation or AI tools.
- Strong attention to detail and ability to execute with structure in ambiguous environments.
- Ability to collaborate effectively with cross-functional partners including Product, Engineering, and Ops.
- Experience in high-growth startups, fintech, payments, or customer support operations preferred.
- Bonus: experience with chatbot authoring, AI evaluation, or support QA.
Life at Flex
We understand that it takes a diverse team of highly intelligent, curious, determined, empathetic, and self aware people to grow a successful company. Our HQ is located in New York City, but we have employees located throughout the US, Australia, Canada and South America. We are growing quickly, but deliberately, with a focus on building an inclusive culture. Our dynamic team has incredible perspectives to share, just as we know you do, and we take great pride in being an equal opportunity workplace.
Offices
Roles posted in New York, San Francisco, and Salt Lake City are hybrid positions with on-site expectations of 2-3 days per week in our local offices. For candidates outside of these areas, you may be eligible for our relocation assistance program.
Benefits
For full-time U.S. employees we offer:
- Competitive medical, dental, and vision
- Company equity
- 401(k) plan with company match
- Unlimited paid time off + 13 company paid holidays
- Parental leave
- Free Flex subscription
For full-time non-U.S. employees, we offer:
- Competitive compensation + company equity
- Unlimited PTO
