Head of Retail Operations (Remote)

Enterprise Operations Manager
RedSail is committed to delivering an exceptional experience for our customers. The Enterprise Operations Manager plays a critical role in fulfilling that commitment by serving as the dedicated operational and technical partner for assigned strategic customer(s). Acting as the customer's trusted operational advisor and primary point of contact for technical and service delivery matters, the Enterprise Operations Manager develops a deep understanding of each customer's business, pharmacy operations, systems, and strategic priorities. The Enterprise Operations Manager owns day-to-day operational success by coordinating resources across RedSail, driving cross-functional execution, and ensuring issues are resolved efficiently and effectively. Through strong partnership, technical expertise, and end-to-end accountability, this role ensures customers experience RedSail as one integrated team committed to their long-term success.

Strategic Account Ownership

Serve as the dedicated operational and technical partner for assigned strategic customer(s), developing trusted relationships through exceptional service and operational excellence.

Develop a comprehensive understanding of each customer's pharmacy operations, business priorities, pharmacy management systems, integrations, claims routing, data exchanges, and unique workflows.

Partner closely with the assigned Business Development Manager to deliver a seamless customer experience, ensuring strong coordination between commercial strategy and operational execution.

Maintain comprehensive customer playbooks, including technical configurations, operational workflows, contact maps, customer preferences, known issues, and account-specific procedures.

Serve as the primary operational owner for customer issues, providing end-to-end ownership from initial engagement through successful resolution.

Resolve technical and operational issues quickly and accurately, minimizing disruption to pharmacy operations and maintaining proactive communication throughout the resolution process.

Troubleshoot issues involving claims processing, transaction routing, connectivity, enrollment, file transfers, integrations, and data discrepancies.

When escalation is required, engage Engineering, Product, Network Operations, or other internal teams with complete technical context while remaining the customer's single point of accountability until resolution is achieved.

Coordinate cross-functional resources to ensure customers experience RedSail as one integrated organization regardless of which teams are involved.

Proactive Customer Partnership

Monitor operational trends, recurring issues, and account health to identify opportunities for improvement before issues impact the customer.

Recommend process improvements and operational best practices that enhance customer efficiency, service quality, and overall experience.

Lead recurring operational reviews focused on service performance, operational metrics, open initiatives, system changes, and continuous improvement opportunities.

Anticipate customer needs by maintaining a deep understanding of upcoming business initiatives, operational priorities, and platform changes.

Translate customer needs into clear technical and operational requirements for internal teams while communicating technical concepts to customers in a clear, business-focused manner.

Act as the internal advocate for assigned customers, ensuring priorities are understood and appropriately represented across Product, Engineering, Operations, Support, and other functional teams.

Partner with Compliance and Privacy teams to ensure customer communications and data handling align with contractual, regulatory, and security requirements.

Provide voice-of-customer insights to Product and Operations leadership, helping influence future enhancements and operational improvements.

Required Work Experience/Skills

5+ years of experience in enterprise account management, technical account management, customer operations, technical support, customer success, or a related customer-facing role supporting complex B2B environments.

Demonstrated ability to diagnose and resolve complex operational and technical issues involving integrations, transaction processing, system connectivity, data exchange, or enterprise software platforms.

Proven ability to build trusted relationships with enterprise customers while delivering exceptional service and operational results.

Strong organizational and project management skills with the ability to coordinate multiple priorities across cross-functional teams.

Excellent written and verbal communication skills, including experience interacting with customer leadership and executive stakeholders.

Preferred Work Experience/Skills

Experience supporting enterprise healthcare technology, pharmacy technology, PBM, claims processing, healthcare data exchange, or SaaS platforms.

Familiarity with NCPDP standards, BIN/PCN, claims adjudication, pharmacy workflows, or healthcare interoperability.

Experience supporting large retail pharmacy chains or other multi-site enterprise healthcare organizations.

Bachelor's degree or equivalent combination of education and experience.

Successful Enterprise Operations Manager:

Become trusted operational advisors to their customers.

Deliver highly personalized service through deep knowledge of each customer's business and environment.

Anticipate customer needs and proactively identify opportunities to improve operational performance.

Coordinate internal teams to deliver a seamless, consistent customer experience.

Champion the voice of the customer while helping RedSail continuously improve its products, services, and operations.

Uses independent judgment and discretion based upon the employee’s experience in the position and knowledge of the products, equipment, and services

Moderate or high levels of stress may be experienced in the performance of the job

Position is performed in a general office environment, home office, or approved remote workspace where physical work includes, but is not limited to, sitting, standing, reaching, kneeling, bending, and lifting to 25 lbs.

Equipment

Daily use of the Microsoft Teams (phone), computer, printer, and other routine office equipment

Job is performed in an office setting where there are no hazardous materials or equipment

Position is performed in an open office environment or approved remote work location

Hybrid at a RedSail Office

This position is also eligible to participate in RedSail's annual incentive bonus program, with a target opportunity of 4% of base salary. Actual bonus payout is based on company performance and is subject to the terms and conditions of the applicable bonus plan. Actual compensation will be determined based on factors including relevant experience, skills, qualifications, internal equity, and geographic location.

medical, dental, and vision insurance; professional development opportunities;