Sr. Director of Customer Experience

Swooped is a Talent Platform (not a staffing agency). We are not the employer for this role and do not make hiring decisions. Clicking "Apply" takes you to Swooped to review the role and hiring company details.

About the Opportunity

The company is making benefits easy. It believes people are the most important asset to any organization. Traditional one-size-fits-all benefits packages no longer cut it in today's hybrid and remote-first environment. With the company's platform, organizations can tailor their benefits to the unique needs of their workforce.

Through an easy-to-use and highly customizable fintech platform, People teams can implement, administer, and track the benefits that meet employees where they are. Employers design their benefits and perks plan by setting a contribution amount and eligible spend categories. Every employee has their own individual definition of wellness and needs different things to help them be their most productive, fulfilled self.

Our Mission

Helping companies reimagine how they take care of their people.

Our Investors

The organization is backed by leading investors. To date, the company has raised $35 million of equity capital.

The Role

The company is seeking a strategic and operationally strong Senior Director of Customer Experience to lead and scale its Customer Experience organization. This leader will oversee two core functions: (1) the Customer Support team serving both enterprise administrators and end users on the platform, and (2) the Claims Operations team responsible for claims adjudication and processing.

This role will define and execute the vision and operating model for Customer Experience, ensuring 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 is strongly preferred.

What You’ll Do

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.

What You Bring

• 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 plans.
• 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.
• 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.

Compensation

• Base salary of $180,000 to $210,000 + equity.

The range is subject to change. The company takes a number of factors into account when determining individual starting pay, including market comparables, interview performance, peer compensation, and years of experience.

What We Offer

• 95% coverage of medical, dental, and vision
• Fantastic benefits, including:
• Several team onsites a year
• Flexible PTO

The organization is working towards reimaging how companies take care of their people. It is committed to creating an inclusive environment for all employees and is seeking to build a team that reflects the diversity of the people it hopes to serve with its revolutionary products. The company is proud to be an equal-opportunity employer.