Enterprise Operations Director

The Enterprise Operations Director provides strategic leadership for RedSail’s technical account management function and is accountable for the operational health, technical success, and long-term value delivered to assigned strategic and enterprise customers. This leader defines the strategy, service model, standards, and performance expectations for Enterprise Operations Managers while building a high-performing team that serves as a trusted operational and technical advisor to customers. The Director develops strong executive relationships, provides oversight for complex escalations and customer-impacting incidents, and ensures the organization proactively manages account risk, service performance, and continuous improvement. The Director establishes scalable processes, governance, metrics, and capacity plans that improve customer outcomes and operational efficiency. Through strategic leadership, technical credibility, and enterprise-wide influence, this role ensures customers experience RedSail as one integrated organization committed to their long-term success.

Key Duties

Strategic Account Ownership

• Define and execute the vision, operating model, service standards, and annual priorities for the Enterprise Operations Management function in alignment with RedSail’s customer experience and growth objectives.
• Develop executive-level relationships with strategic customers and serve as the senior operational and technical sponsor for account health, risk mitigation, and value realization.
• Establish portfolio segmentation, engagement models, coverage requirements, and account planning standards that provide consistent, scalable support for strategic customers.
• Partner with Sales, Customer Success, and Business Development leadership to align commercial strategy, customer commitments, and operational execution.

• Establish and monitor KPIs, SLAs, account-health indicators, escalation thresholds, and reporting mechanisms that measure service quality, responsiveness, operational risk, and customer outcomes.
• Provide executive oversight for complex customer escalations and critical incidents, ensuring clear ownership, timely communication, disciplined root-cause analysis, and durable corrective actions.
• Drive consistency in technical account plans, customer playbooks, operational reviews, risk registers, and escalation practices across the team.
• Use data and customer insights to identify systemic issues, prioritize investments, and improve the reliability, scalability, and supportability of RedSail solutions.
• Lead capacity planning, resource allocation, and operating rhythms to support changing customer demand and business priorities.

• Lead, coach, and develop a high-performing team of Enterprise Operations Managers, setting clear expectations and fostering accountability, collaboration, customer focus, and continuous learning.
• Own workforce planning, organizational design, recruiting, onboarding, performance management, talent development, and succession planning for the function.
• Build team capabilities in executive communication, technical problem-solving, incident leadership, strategic account planning, and business acumen.
• Create a culture that balances high-touch customer partnership with repeatable, scalable, and measurable operating practices.

• Influence Product, Engineering, Operations, Support, and Compliance priorities by translating customer needs and recurring operational challenges into clear business and technical requirements.
• Represent the voice of the customer in leadership forums and provide actionable insights that inform roadmaps, service improvements, and investment decisions.
• Establish governance for customer-impacting changes, operational readiness, incident communications, and follow-through on corrective actions.
• Lead cross-functional initiatives that improve customer experience, reduce recurring issues, increase team productivity, and strengthen operational performance.
• Present account-health trends, risks, performance results, and recommendations to senior and executive leadership.

• 10+ years of progressive experience in enterprise operations management, customer operations, enterprise support, customer success, professional services, solution architecture, or a related customer-facing technology function.
• 5+ years of leadership experience, including responsibility for hiring, coaching, performance management, organizational design, and talent development.
• Demonstrated success leading enterprise-facing technical teams and managing complex, integration-heavy customer environments.
• Proven ability to establish scalable operating models, service standards, KPIs, SLAs, account-health frameworks, and escalation governance.
• Strong executive presence with experience building trusted relationships, leading business reviews, and communicating risk, performance, and strategy to senior stakeholders.
• Demonstrated technical and business judgment in resolving complex issues involving integrations, transaction processing, system connectivity, data exchange, or enterprise software platforms.
• Strong analytical, financial, organizational, and change-management skills with the ability to translate data into priorities and measurable business outcomes.
• Excellent written, verbal, presentation, and influence skills across technical and non-technical audiences.

• Experience leading enterprise account management, enterprise customer success, or professional services teams in healthcare technology, pharmacy technology, PBM, claims processing, healthcare data exchange, or SaaS environments.
• Knowledge of NCPDP standards, BIN/PCN, claims adjudication, pharmacy workflows, healthcare interoperability, or other regulated transaction environments.
• Experience supporting large retail pharmacy chains or other multi-site enterprise healthcare organizations.
• Experience operating in HIPAA-regulated environments and partnering with Privacy, Security, or Compliance teams.
• Bachelor’s degree in business, technology, healthcare administration, or a related field; master’s degree preferred. An equivalent combination of education and relevant experience may be considered.

Success In This Role Is Demonstrated By

• Improved customer retention, confidence, satisfaction, and value realization across strategic accounts.
• Consistent achievement of service, response, resolution, account-health, and operational performance targets.
• Reduced frequency, duration, and recurrence of customer-impacting incidents and escalations.
• A scalable, disciplined Enterprise Operations Management operating model with clear standards, governance, documentation, and reporting.
• A highly engaged, capable, and accountable team with strong development and succession pipelines.
• Effective cross-functional alignment that converts customer insights into measurable product, service, and operational improvements.

• Exercises broad independent judgment in setting functional priorities, allocating resources, addressing customer and operational risk, and making decisions with material impact on strategic accounts and business performance.
• Makes timely decisions in ambiguous, high-impact situations while balancing customer commitments, technical constraints, regulatory requirements, and organizational priorities.
• Uses sound judgment, maintains confidentiality, and demonstrates ethical leadership.

• 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.

• Daily use of the Microsoft Teams (phone), computer, printer, and other routine office equipment
• Must have internet access

• Little responsibility for safety of others. 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
• Spartanburg, SC
• Irving, TX
• Shreveport, LA
• Oak Brook, IL
• Cranberry Township, PA
• Long Island, NY
  

The anticipated base salary range for this position is $135,000–$145,000 annually. This position is also eligible to participate in RedSail's annual incentive bonus program, with a target opportunity of 7.5% 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.

RedSail offers a comprehensive benefits package, including paid time off; medical, dental, and vision insurance; a 401(k) plan with a company match; professional development opportunities; and programs that support employee health and well-being. Benefit offerings are subject to the terms and conditions of the applicable plans and may be modified from time to time.