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.
Flex takes a market-based approach to pay, ensuring compensation is commensurate with a candidate's experience and our internal leveling guidelines. For candidates located in our Tier 1 (NYC/Bay Area) and Tier 3 (Salt Lake City) markets, the base salary pay range for this role is below. Flex utilizes a geographic pay differential based on a cost of labor index. If you are located outside of the cities listed below, your starting pay will be adjusted to align with the market conditions of your specific geographic zone. Please speak with your recruiter for additional information regarding the specific range for your location.
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
Skills Required
- 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
- Experience with chatbot authoring, AI evaluation, or support QA
Flex Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Flex and has not been reviewed or approved by Flex.
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Healthcare Strength — Day-1 medical, dental, and vision coverage is explicitly offered and framed as “best-in-class coverage and options,” suggesting strong baseline health benefits. Additional listings also describe broad health-support elements such as IVF/adoption and gender transition benefits, reinforcing depth in healthcare-related coverage.
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Retirement Support — A 401(k) is available, with a stated company match starting in early 2026, indicating improving retirement support. This rollout appears to address earlier gaps where matching was not consistently present.
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Leave & Time Off Breadth — Unlimited PTO plus company holidays (and, in some descriptions, shutdown days) indicates a wide time-off policy on paper. Hybrid work flexibility and office-day meal credits can add to the overall rewards value for NYC-based employees.
Flex Insights
What We Do
Flex, an NYC-headquartered FinTech company, has created a trusted rent payment experience. It’s hard to believe that it’s 2024 and paying rent on time is expensive, inflexible, and difficult; we’re here to change that! We enable our users to pay rent throughout the month on a schedule that better fits their finances and budget, while also helping them build credit. Our mission is to empower as many renters as possible with flexibility over their most significant recurring expense.
Why Work With Us
We believe it takes a diverse team of curious, determined, empathetic, and self aware people to grow a successful company. We value the unique and dynamic perspectives our team brings to solve critical problems that impact the lives of our users and the financial decisions they make.
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