Flex
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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 (NYC), the base salary pay range for this role is $108,000—$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.
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
- Flex Cares Program: Non-profit company match + pet adoption coverage
- Free Flex subscription
For full-time non-U.S. employees, we offer:
- Competitive compensation + company equity
- Unlimited PTO
Ready to apply?
Apply to Flex
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 $108,000—$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.
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
- Flex Cares Program: Non-profit company match + pet adoption coverage
- Free Flex subscription
For full-time non-U.S. employees, we offer:
- Competitive compensation + company equity
- Unlimited PTO
Ready to apply?
Apply to Flex
Program Manager, CS Tools & Technology
Share this job
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
Flex is rewriting the rules of rent payment, and our CS Tools & Technology team is at the center of making that experience seamless for every renter we serve. As a Technical Program Manager on the CS Tools & Technology team, you'll report directly to the Director of CS Tools & Technology and own the systems, programs, and integrations that power Flex's customer support operations — from Zendesk and automation pipelines to custom-built internal tools and cross-functional integrations.
This is not a traditional TPM role. While you'll own program delivery, backlog prioritization, and roadmap execution, this role requires deep, hands-on involvement in designing, building, and operating solutions across our CS Tools & Technology stack. You'll operate as a builder-operator: someone equally comfortable presenting a strategic roadmap to senior leadership and then personally diving into Zendesk workflows, APIs, or automation logic to bring that roadmap to life. The ability to move fluidly between strategy, technical execution, and operational detail — without losing momentum in any layer — is what sets this role apart.
Success here means you're the connective tissue between CS, Product, Engineering, Finance, and BPO partners — translating operational pain points into scalable technical solutions, keeping complex workstreams moving, and ensuring our CS Tools & Technology stack grows with the business. If you thrive at the intersection of strategy, execution, and technical craft, this role was built for you.
What You'll Do
- Own and manage the team's backlog, sprint planning, and prioritization across all active workstreams, driving end-to-end delivery of large-scale initiatives such as tool migrations, live chat, telephony, and internal tooling
- Translate business needs and operational pain points into clear functional specifications, user stories, and acceptance criteria — then personally configure, integrate, or guide development of those solutions hands-on
- Lead UAT planning to ensure solutions meet real-world operational needs before launch, and document systems, workflows, and integrations to support long-term scalability and knowledge transfer
- Configure and administer CS platforms — primarily Zendesk — including triggers, automations, routing logic, SLA management, and agent workspace design
- Design and implement integrations using APIs, webhooks, and automation tools such as Zapier, scoping technical feasibility and maintaining scalable pipelines
- Own CS operational dashboards and reporting, partnering with CS leadership to define KPIs, surface insights, and drive data-informed decisions
- Leverage AI-assisted development tools (e.g., Claude, GitHub Copilot) to build or guide custom solutions, and champion AI-enabled workflows across the team
- Produce executive-ready outputs — roadmaps, status updates, project briefs, and post-implementation reviews — while identifying risks and unblocking dependencies across cross-functional teams
What You'll Bring
- 4–7 years of experience in technical program management, business systems, or support technology with a track record of increasing ownership and end-to-end delivery
- Proven builder-operator mindset: the ability to own program delivery while also executing hands-on within systems, integrations, and automation logic
- Deep hands-on experience with Zendesk administration, including workflow design, routing logic, SLA management, and troubleshooting
- Practical experience with APIs, webhooks, and automation tools (Zapier or equivalent) for system integration and workflow automation
- Demonstrated use of AI-assisted development tools to build or guide custom solutions — this is an expectation of the role, not a nice-to-have
- Strong written and verbal communication skills, including experience producing executive-facing materials such as roadmaps, status updates, and project briefs
- Ability to operate independently across multiple concurrent workstreams in a fast-moving, high-growth environment
- Experience collaborating cross-functionally with teams such as Product, Engineering, Finance, and external BPO partners
Nice to Have
- Experience in FinTech or high-growth consumer tech environments
- Familiarity with BPO operations and multi-partner support models
- Exposure to WFM tools (e.g., Tymeshift, Assembled), Salesforce, or similar platforms
- SQL or data querying experience
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 (NYC/SF), the base salary pay range for this role is $108,000—$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.
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
- Flex Cares Program: Non-profit company match + pet adoption coverage
- Free Flex subscription
For full-time non-U.S. employees, we offer:
- Competitive compensation + company equity
- Unlimited PTO
Ready to apply?
Apply to Flex