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Director CS Tools & Technology

New York, New York, 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 2025 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 are seeking a Director, Customer Service (CS) Tools & Technology to lead and scale our customer support technology ecosystem. This role will oversee the administration and evolution of all CS-related tools, ensuring our customer service teams and BPO partners have the right technology, processes, and data to deliver best-in-class support.

As a people leader, this individual will drive system enhancements, tool implementations, and operational efficiencies while collaborating closely with Product, Engineering, and other key stakeholders to align technology solutions with business needs.

This is a high-impact role for someone with deep CRM expertise (Zendesk, Salesforce, or other enterprise CRM systems) and experience optimizing and implementing customer support technology at scale.

This is a hybrid position with on-site expectations of 3 days per week in our New York Headquarters. For candidates outside of the NY/NJ area, you may be eligible for our relocation assistance program.

What you’ll do

  • Lead and manage the CS Tools & Technology team, overseeing the administration and optimization of all customer service-related platforms (Zendesk, Salesforce, or other enterprise CRM applications).
  • Develop and execute a strategic roadmap for evolving our support tools, automation, and AI-driven solutions to improve efficiency, scalability, and customer experience.
  • Drive the evaluation and implementation of new technologies, ensuring seamless integration with existing systems and alignment with broader company objectives.
  • Partner cross-functionally with Product, Engineering, Finance, and BPO operations to ensure technology solutions support evolving business needs.
  • Establish and optimize reporting frameworks for operational metrics, data analytics, and performance insights, providing real-time visibility into support trends, costs, and service scalability.
  • Ensure readiness for new product and service launches, proactively aligning tools and systems to support growth and maintain operational stability.
  • Monitor system uptime, reliability, and performance, driving continuous improvements and minimizing disruptions.
  • Optimize vendor relationships, ensuring that service level agreements (SLAs), costs, and capabilities align with business goals.
  • Support and enhance BPO operations by equipping external partners with the right tools, integrations, and access to effectively manage customer interactions.
  • Stay ahead of industry trends and innovations, keeping the CS technology stack competitive and future-proof.

Key qualifications

  • 8+ years of experience in customer service technology, CRM administration, or support operations, preferably with at least 4+ years in a leadership role.
  • Deep expertise in Zendesk, Salesforce, or other enterprise CRM applications, with experience in optimizing existing systems and/or leading full-scale implementations.
  • Strong cross-functional leadership skills with a proven ability to align technology initiatives across Product, Engineering, and Operations.
  • Experience managing data and analytics reporting frameworks for customer service operations, including operational reporting, scalability metrics, and service cost analysis.
  • Demonstrated success in improving CS technology solutions for BPO operations and scaling support tools in high-growth environments.
  • Understanding of automation, AI-powered support solutions, and chatbot integrations is a plus.
  • Ability to navigate complex support ecosystems, balancing innovation with operational efficiency.
  • A proactive, problem-solving mindset with the ability to drive change and execute strategic initiatives at scale.

 

The compensation range for this role will be commensurate with the candidate's experience and Flex's internal leveling guidelines and benchmarks.

For working locations in NY/NJ/CA, the base salary pay range will be $169,000 - $183,000

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. For full time, U.S. based employees we offer:

  • Competitive pay
  • 100% company-paid medical, dental, and vision
  • 401(k) + company equity
  • Unlimited paid time off with a PTO minimum + 13 company paid holidays
  • Parental leave 
  • Flex Cares Program: Non-profit company match + pet adoption coverage
  • Free Flex subscription

 For full time non-US employees, we offer

  • Competitive Pay
  • Company Equity
  • Unlimited PTO

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