Senior Director of Customer Experience, Benepass
$180-210k
Plus equity
Benefits administration platform
Be an early applicant
Benefits administration platform
21-100 employees
Be an early applicant
$180-210k
Plus equity
21-100 employees
Company mission
To help companies distribute meaningful benefits that support the personal and professional well-being of their team.
Role
Who you are
- 10+ years of experience in Customer Experience, Support, or Operations leadership, with demonstrated success scaling multi-channel support organizations in high-growth environments
- Experience leading managers, support operations functions, with a track record of developing high-performing, metrics-driven CX teams
- Proven ability to design and implement scalable operating models, including capacity planning, volume forecasting, and workforce management across multiple support channels
- Experience building and maturing support operations infrastructure, including knowledge management, QA programs, training and enablement, reporting, and tooling ecosystems
- Demonstrated success scaling a process-driven or compliance-sensitive function (e.g., claims adjudication, financial operations, benefits administration, or similar) while maintaining high quality and SLA adherence
- Strong command of CX performance metrics (CSAT, NPS, FCR, AHT, SLA attainment, productivity, quality, accuracy) and experience translating operational data into executive-level insights and action plan
- Experience implementing and leveraging AI-enabled support technologies (e.g., chatbots, agent assist, automation, intelligent routing, workflow optimization) to drive efficiency and enhance customer outcomes
- Track record of introducing operational rigor, establishing clear productivity and quality standards, and driving measurable performance improvement
- Experience managing and optimizing relationships with external vendor partners or BPOs
- Strong cross-functional leadership skills, with the ability to influence Product, Engineering, Operations, and Revenue teams to address systemic drivers of customer friction
- Excellent executive communication skills, with comfort presenting operational performance, risks, and strategic plans to senior leadership
- A systems thinker who balances customer empathy with operational discipline and scalable process design
What the job involves
- We are seeking a strategic and operationally strong Senior Director of Customer Experience to lead and scale Benepass’s Customer Experience organization
- This leader will oversee two core functions: (1) our Customer Support team serving both enterprise administrators and end users on the Benepass platform, and (2) our Claims Operations team responsible for claims adjudication and processing
- This role will define and execute the vision and operating model for Customer Experience, ensuring we consistently deliver timely, accurate, and empathetic support across every customer interaction
- The Senior Director will be accountable for end-to-end service performance, including customer satisfaction, quality, responsiveness, and operational efficiency
- They will establish clear service standards and KPIs, implement scalable processes and tooling, and build the infrastructure - people, systems, workflows, and reporting - required to support a growing customer base
- This leader will drive continuous improvement across support and claims operations, identifying opportunities to streamline workflows, reduce friction, improve first-contact resolution, and elevate the overall customer journey
- Beyond day-to-day operations, this leader will also translate customer insights and operational data into clear product, process, and tooling improvements, partnering cross-functionally to resolve root causes, enhance the customer experience, and inform roadmap decisions
- The ideal candidate brings deep experience scaling multi-channel support organizations in high-growth environments and has built and optimized core support operations capabilities, including training, quality assurance, knowledge management, workforce management, and capacity planning
- They are fluent in AI-powered support delivery and have successfully implemented AI solutions that improve speed, accuracy, and customer satisfaction while driving operational leverage
- This leader has experience managing managers and developing layered teams, setting clear performance and quality standards, and fostering a culture of accountability and continuous improvement
- They are highly metrics-oriented, with strong command of CX performance indicators (e.g. , CSAT, NPS, SLA adherence, FCR, AHT, quality, productivity, accuracy), and are comfortable building executive-level reporting that translates operational data into clear business insights and recommendations
- Experience launching new channels of support and managing and optimizing relationships with external vendor partners (BPOs) is strongly preferred
- Set the Vision & Operating Model for Customer Experience
- Define and execute the long-term vision and service model for Customer Experience, aligning support and claims operations to company growth objectives
- Own the annual planning process for CX, identifying strategic priorities, major initiatives, service model evolutions, and investment needs
- Establish the operating framework, governance, and performance standards required to scale a high-quality, multi-channel support organization
- Design and implement AI-powered support delivery mechanisms to improve efficiency and service quality
- Lead & Scale a High-Performing Organization
- Lead, develop, and scale the Customer Experience and Claims org, managing managers, FTEs, vendors, and contractors, and building a strong leadership bench within the team
- Design and implement clear career pathways and succession plans to support long-term organizational health
- Foster a high-performance, accountability-driven culture grounded in service excellence, operational discipline, and continuous improvement
- Build Scalable Infrastructure & Support Operations
- Stand up and mature critical support operations capabilities - including knowledge management, workforce management, training and enablement, quality assurance, tooling, and reporting infrastructure - to enable efficient, high-quality scale
- Develop robust capacity and volume forecasting models across a multi-channel environment to inform hiring plans, budget decisions, and service targets; evaluate and implement workforce planning technology as complexity grows
- Introduce operational rigor by defining productivity standards, quality benchmarks, and performance management systems that ensure consistency and accountability
Our take
The US labor market is creating higher demand for top tier talent, and many companies are looking to improve their benefits as a way of staying competitive. Strong health insurance and holiday policies, however, no longer cut it. Benepass is a benefits administration company looking to help companies stay ahead in this new landscape.
The basic Benepass premise is that pre- and post- tax benefits should be flexible and accessible for employees. As things stand, tax-advantage benefits are hugely under-leveraged by employees, because they are hard to use or unsuitable for individuals. Benepass’ app centralises and simplifies the process, allowing employees to explore, track, and exercise benefits from a single platform and VISA card.
Many platforms directed towards simplifying employee benefits don’t yet offer the same tangible features, and also don't focus on the more complex area of tax-advantage benefits. Therefore, Benepass’ solution is an easy win/win, which is why it has gained strong funding and attention. The latest influx fuels the expansion of its offerings, for example to support more specialized and cost-sensitive employer programs.
Freddie
Company Specialist at Welcome to the Jungle
Insights
8% employee growth in 12 months
Company
Funding (last 2 of 5 rounds)
Jan 2026
$40m
SERIES B
Jan 2024
$20m
EARLY VC
Total funding: $74.4m
Company benefits
- Healthcare: We pay $430 per month toward your health insurance and fully cover dental and vision. You also get membership to OneMedical, Teladoc and Talkspace
- Flexible, autonomous work: We’re remote first so live where you’re most happy. We come together in-person as a team 3-4 times per year
- Benepass perks: $500 to set up your home office, $100 per month for wellness, however you define it, $150 per month for home internet and cell phone, $150 per month for co-working
Company HQ
Greenwich Village, New York, NY
Leadership
Jaclyn Chen
(CEO & Co-founder)Previously an Associate at Goldman Sachs, then TPG Capital, before moving on to work in Business Development at Teampay.
Mark Fischer
(Product & Co-founder)An ex-Google Mechanical Engineer, who went on to hold a Senior Robotics Engineering role at X: The Moonshot Factory.
Kabir Soorya
(CTO & Co-founder)An In-Q-Tel technologist who then worked on the Senior Technical Staff at Sidewalk Labs.
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