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Manager, CS AI Content

San Francisco, California, United States

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 Manager, 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 systems design. You’ll translate customer support knowledge, SOPs, and workflows into structured, machine-readable content that enables AI systems to respond accurately, take action through APIs, and safely support customers across channels.

You’ll design content for conversational AI, including multi-turn dialogue flows, clarification strategies, and safe recovery paths. The content you create directly impacts containment, CSAT, and risk prevention, making this a high-impact, cross-functional role.

What you’ll do

  • Write and maintain AI-native content that powers chatbot and agent assist behavior, including structured responses, decision trees, and escalation logic.
  • Design conversational AI dialogue flows, including multi-turn interactions, clarifying questions, and safe handoffs to human support.
  • Strengthen AI workflows by leveraging API calls, enabling AI tools to retrieve data, trigger actions, or route conversations appropriately.
  • Identify and close gaps in SOPs and support documentation that limit AI understanding or accuracy.
  • Disambiguate overlapping or ambiguous concepts to improve AI reasoning and response quality.
  • Partner with Product and Engineering to launch new AI tools or expand AI capabilities across other channels.
  • Maintain version-controlled AI training content that is audit-ready and aligned with policy and regulatory requirements.
  • Measure and improve AI performance using containment, CSAT, escalation trends, and P0 signals.

Key qualifications

  • Experience in Customer Success, Content Operations, Trust & Safety, QA, or similar fields.
  • Hands-on experience with conversational AI or AI-powered support tools.
  • Comfort designing content or workflows that interface with systems (APIs, automation, AI tools).
  • Strong problem-solving skills and ability to bring structure to ambiguous problems.
  • Ability to collaborate effectively with Product, Engineering, Data Science, QA, and Ops partners.
  • Experience in high-growth startups, fintech, payments, or customer support operations preferred.

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 markets (San Francisco, CA), the base salary pay range for this role is $122,000—$135,000 USD.

For all other U.S. locations, Flex utilizes a geographic pay differential based on a cost of labor index. If you are located outside of the Tier 1 states listed above, 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

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.

We offer many employee benefits & perks. For full-time U.S based positions we offer:

  • Competitive medical, dental, and vision available from Day 1
  • Company equity
  • 401(k) plan with company match (our company match kicks off at the beginning of 2026)
  • Unlimited paid time off + 13 company paid holidays
  • Parental leave 
  • Flex Cares Program
  • Free Flex subscription

 For full time non-US employees, we offer

  • Competitive compensation + company equity
  • Unlimited PTO

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