Sr. Director of Customer Experience and Sales Operations

Keystone Advisors Overview

At Keystone Advisors we partner with top insurers to help clients find essential health coverage in 49 states. We provide individuals, families, and businesses with health, dental, vision options, as well as Medicare options including Medicare Advantage, Medicare Supplement Insurance, and Prescription Drug Part D plans.

We are experts in the health insurance market and define our outstanding performance. Our team gives their best to match our clients’ needs. We are proud of helping thousands of Americans to find peace of mind and economic stability. Even though many things have changed throughout the decades, one thing remains the same: We are the key to finding the right health plan for you.

Job Purpose

We are seeking a strategic and operationally minded Sr. Director of Customer Experience and Sales Operations to lead the evolution of service delivery and operational readiness across all lines of business. This senior leader will champion customer satisfaction, execute strategic initiatives, and ensure service alignment for new ventures launched by our Sales, Tech, and Broker Development teams. With a strong focus on innovation, scalability, and performance, this role is instrumental in improving retention and building customer trust across the organization.

Duties and Responsibilities

Ownership of New Service Business Models Lead the development, innovation, and execution of new service lines—including third-party call center

contracts, public program support, and white-labeled services. Ensure alignment with organizational goals and scalability for future growth.

• Execution of Strategic Initiatives & RFPs Manage the customer service components of high-priority strategic initiatives and RFPs. Coordinate cross-functional teams to deliver results on time and within scope, ensuring service excellence is a key differentiator.

• Service Readiness for New Business Lines Partner with Sales, Tech, and Broker Development teams to ensure service functions are fully prepared to support new product launches or partnerships. Anticipate operational needs and build service frameworks that are scalable, efficient, and aligned with customer expectations.

• Customer Experience Leadership Act as the internal champion for customer experience across the organization. Work closely with cross-functional teams to embed service excellence into every stage of the customer journey.

• Team Leadership & Experience Metrics Lead and develop customer-facing teams to consistently deliver exceptional service. Implement systems to collect, analyze, and act on customer feedback and experience metrics. Use insights to drive continuous improvement and decision-making.

Qualifications

Required Qualifications · Bachelor’s degree in Business, Operations, Customer Experience, or related field · 8+ years of progressive experience in customer service leadership, operations, or service delivery · Proven ability to design and scale service models across multiple business lines · Strong understanding of CRM systems, customer feedback tools, and service metrics · Track record of leading cross-functional teams through complex initiatives and partnerships · Excellent communication, strategic planning, and problem-solving skills · Experience managing or contributing to RFP processes and external contracts

Preferred Qualifications · Experience in healthcare, insurance, or government program support · MBA or advanced degree in a relevant field · Familiarity with Salesforce, HubSpot, Zendesk, or similar platforms · Experience with service design, lean operations, and customer journey mapping

Working Conditions

• Business office environment

• Flexibility for remote or hybrid work as needed

• May require extended hours during high-impact project phases or seasonal periods