Digital Success Executive Team Leader

Job Introduction

Background:

Agilio Software Group is a leading UK healthcare operations software provider, delivering integrated, mission-critical solutions that support primary care, dental, pharmacy, hospital, and veterinary organisations. With ambitious growth plans underway, we are looking for talented individuals to join us on this exciting journey.

Role Summary

The Digital Success Executive Team Leader operates within a pooled delivery model, providing advanced digital success interventions, handling escalations, and supporting the effectiveness and consistency of the DSE team. The role combines hands on delivery with managing a small team: coaching, quality oversight, and cross functional coordination to ensure a scalable, high quality customer experience.

Key Responsibilities

• Customer Management & Engagement
• Deliver onboarding, adoption, and risk management interventions to SMB customers from the shared DSE pool, based on priority and escalation.
• Oversee, review, and report on the digital customer journey, ensuring key milestones are met.
• Monitor customer health indicators and identify additional indicators.
• Manage interventions for usage drops, missed milestones, or risk signals.
• Contribute to overall GRR and retention outcomes through effective handling of escalations, complex cases, and renewal related interventions.
• Own the resolution of escalated customer complaints, ensuring appropriate prioritisation, cross functional coordination, and clear communication until resolution.
• Undertake any other reasonable duties as required by the Head of Customer Success to support the effective management and delivery of customer success services.
• Ensure clear documentation and structured handovers so escalated or complex cases can move smoothly between team members without loss of context.

Operational & Support Responsibilities

• Manage team of three Digital Success Executives including 121s and annual reviews
• Act as the escalation point for customer complaints and complex issues from the DSE team, ensuring timely resolution and adherence to agreed standards.
• Provide guidance on prioritisation, approach, and escalation paths for complex customer scenarios within agreed authority levels.
• Handle complex or escalated renewal queries, operating within defined negotiation and escalation frameworks.
• Carry out data analysis and ad hoc Planhat work, including workflow, milestone and playbook reviews/updates, and segmentation cleanups.
• Maintain accurate CRM notes and customer documentation.
• Reply to inbound queries appropriately.
• Support team with client conversations and aligning internal stakeholders

Cross Functional Collaboration

• Coordinate with Support, Product, and other internal teams on escalated or systemic issues, ensuring ownership is clear and outcomes are driven to resolution.
• Identify recurring themes, risks, or inefficiencies arising from pooled delivery and proactively surface structured insights to the Head of Customer Success.
• Act as a role model and coach for DSEs, reinforcing best practice, quality standards, and consistent execution across the pooled team.
• Share insights and trends with the wider Customer Success team to improve processes at scale.
• Align team activity to business direction and agreed priorities.
• Provides context and clarity on organisational decisions impacting the team.
• Actively seek out opportunities for process improvement and innovation to enhance overall CS performance.
• Collate DSE feedback to share with Head of Customer Success
• Support Head of Customer Success with reporting or other ad hoc duties.

Skills & Experience

• 2+ years' experience in a Team Leader role, or significant experience as a Senior-level professional within Customer Support, Customer Success, Account Management, Onboarding, or a related customer-facing function.
• Comfortable operating in a pooled or shared ownership delivery model, managing work dynamically based on priority rather than named customer ownership.
• Strong judgement and decision making skills when handling escalations, ambiguity, and competing priorities.
• Ability to balance hands on delivery with coaching, quality oversight, and operational improvement.
• Strong organisational skills, data analytics, and ability to handle large volumes of customers, tasks, and admin with accuracy and consistency.
• Confident support and being primary representative for team.
• Comfortable working at pace in a dynamic and reactive environment.
• Excellent communication and problem-solving skills.
• Confident engaging senior stakeholders on behalf of the team.
• Comfortable delivering both 1:1 and group customer interactions.
• Empathetic, patient, and committed to delivering an exceptional customer experience.
• Strong written and verbal negotiation skills.•    Confident using CRM systems, Planhat or similar digital tools, and basic reporting dashboards.•    Naturally curious, always seeking to understand customer behaviour, problems, and opportunities.

Additional Information

• Job Type: Remote, full time permanent position.
• Salary: £33,000-£35,000 per annum, dependent on skills and experience.

Benefits include:

• Income Protection
• Life Assurance
• Enhanced pension
• Health Cash Plan
• 28 days annual leave + bank holidays (pro rata for part-time employees)
• Sick pay scheme
• A range of flexible benefits via our Agilio Flex portal

If you feel you have what it takes to join our team, we look forward to receiving your application!

Please note: Due to the volume of applications received, we may not be able to contact every applicant individually. We appreciate your interest in Agilio Software Group and thank you for taking the time to apply.