Head of Business Transformation for Customer Success

POSITION SUMMARY

The Head of Business Transformation for Customer Success will lead Direct Travel's organizational and customer service transformation of Account Management and Implementation functions, translating the strategic Customer Success Transformation Plan into sustained operational reality. This role owns the end-to-end execution of five interconnected transformation pillars: upgrading the customer operating system, implementing AI-human hybrid service delivery, optimizing customer onboarding, unifying global account management teams, and upskilling the team. This role ensures Account Management teams are prepared, engaged, confident, and equipped to adopt new systems, processes, and ways of working—and that transformation investments drive measurable customer outcomes, retention, and growth.

This role serves as the operational and cultural bridge between strategic transformation planning and frontline Account Management execution—ensuring that new technologies, global processes, and organizational structures become embedded capability that sticks.

STRATEGIC MANDATE (Multi-Year Scope)

The leader will own the execution, and sustainability of Direct Travel's Customer Success transformation across five core pillars:

1. Customer Operating System Implementation & Adoption

• Lead the rollout and adoption of Salesforce CRM and customer management systems across all of Account Management and Implementation globally.
• Develop readiness and training strategies so teams confidently adopt new customer tracking, health monitoring, and real-time service request routing workflows.
• Ensure Account Managers transition from tactical execution to advisory roles supported by AI automation and data insights.
• Measure adoption of new systems, process compliance, and customer activity tracking—not just system deployment.
• Drive continuous improvement based on user feedback and adoption metrics.

2. AI-Human Hybrid Delivery Model Adoption

• Own the organizational and behavioral change required for Account Managers to embrace AI as an execution engine for routine tasks, data analysis, and predictive insights.
• Partner with technology teams to translate AI capabilities into practical workflows that elevate Account Manager roles to strategic advisory and executive relationship management.
• Support Account Managers in shifting from task execution to outcome-focused consulting and customer success planning.
• Monitor adoption velocity, user confidence, and business impact via our engagement tools.

3. Global Account Management Unification & Regional Execution

• Lead the change strategy for integrating ATPI and Direct Travel Account Management teams into a unified global operating model.
• Develop and communicate a standardized global customer journey aligned across segments (Global, Enterprise, Mid-Market).
• Build regional and offshore Account Management capacity through team development, training, role clarity, and enablement.
• Facilitate organizational design input sessions and gather frontline feedback on unified operating model rollout.
• Measure adoption of global playbooks, process standardization, and team alignment across regions.

4. Customer Onboarding Optimization & Rapid Activation

• Lead change and adoption strategies for the Customer Onboarding Optimization program (white-glove activation, project accelerators, rapid SMB activation, migration programs, global expansion, and partner channel support).
• Ensure implementation teams and Account Managers understand new onboarding processes and adoption milestones.
• Support capability transfer and knowledge sharing across enterprise, SMB, and migration programs.
• Drive adoption of revenue acceleration tools and customer success methodologies.
• Monitor onboarding adoption, time-to-value, and customer activation rates.

5. Team Upskilling, Capability Development & Organizational Agility

• Lead the People Empowerment and talent transformation initiatives: upskilling the current team on Avenir and modern program optimization, and building repeatable enablement and career paths.
• Develop and scale training programs on Avenir, Strategic Planning, Modern Program Optimization, and Consulting Skills.
• Build a change-ready culture where Account Managers embrace continuous improvement and outcome-based planning.

KEY RESPONSIBILITIES

Transformation Strategy & Planning

• Develop and execute the multi-year Customer Success Transformation roadmap aligned with strategic pillars and business milestones.
• Translate the Account Management Growth Strategy into detailed adoption plans, timelines, and readiness activities.
• Conduct change impact and readiness assessments—identifying which teams, regions, and segments need the most support and what barriers exist to adoption.
• Work closely with the Customer Success PMO, Technology, and Account Management Leadership to align project timelines, dependencies, and adoption readiness.
• Monitor transformation health and adoption progress across all pillars; adjust strategies based on performance data and feedback.
• Build repeatable adoption playbooks and methodologies that scale across geographies and customer segments.

Global Stakeholder Engagement & Communication

• Lead communications and engagement strategies across 100+ Account Managers and multiple geographies.
• Facilitate listening sessions, focus groups, and feedback forums; ensure frontline feedback shapes how new systems, processes, and organizational structures are designed and rolled out.
• Tailor change narratives and adoption strategies to regional and segment needs while maintaining strategic consistency (e.g., Global vs. SMB segments).
• Build trust and psychological safety through transparent, timely communication about what's changing and why.
• Coach and develop Account Management leaders and change champions as transformation advocates in their teams.

Readiness, Training Coordination & Adoption Support

• Partner with Learning & Development and Account Management Leadership to develop role-based learning and readiness activities aligned with transformation milestones.
• Coordinate readiness activities before each major rollout (CRM implementation, offshore expansion, global playbook, Avenir migration, new organizational structure)—ensuring Account Managers have the knowledge, confidence, and resources to adopt new ways of working.
• Design and deliver training on Avenir, Modern Program Optimization, Strategic Planning, and new customer operating system tools.
• Support Account Management leaders with coaching tools, change resources, and adoption frameworks.
• Monitor adoption of new platforms, systems, and processes; gather user feedback and recommend improvements.
• Drive continuous improvement and scaling of best practices across Account Management teams globally.

Leadership, Influence & Capability Development

• Serve as a trusted strategic advisor to the EVP of Customer Success on transformation readiness, adoption progress, and organizational capability.
• Build and maintain strong relationships across Account Management, Implementation, Technology, HR, Training, PMO, and executive leadership.
• Develop and mentor Account Management leaders, change champions, and frontline leaders to build internal transformation capability.
• Model change leadership behaviors and foster a culture of continuous improvement and innovation.
• Represent Customer Success Transformation on executive steering committees and governance bodies.

SUCCESS MEASURES

Quarterly/Annual Metrics

• Account Manager readiness and confidence scores before major rollouts (CRM, organizational restructure, Avenir migration)
• Adoption rates and time-to-adoption for new systems, processes, and tools
• CRM utilization rates and customer health tracking compliance
• Account Manager engagement and sentiment scores
• Change champion network participation and feedback themes
• Training completion and effectiveness scores

Annual/Multi-Year Metrics

• Organizational change maturity progression (2026 baseline → 2028 advanced)
• Global Account Management unification success (measured by process adoption, role clarity, and team alignment—not just project completion)
• Customer migration velocity and adoption rates (Avenir, Core system migrations)
• Customer onboarding time-to-value and activation rates
• Account Manager engagement post-major transformations
• Adoption of segment-aligned operating model and offshore leverage

Strategic

• Direct Travel Account Management becomes known for rapid customer activation, high adoption, and proactive customer success outcomes
• Revenue and margin realization from customer migrations, onboarding optimization, and customer health improvements (adoption-dependent outcomes)
• Ability to scale Account Management into new geographies and customer segments with minimal disruption
• Account Manager capability uplift: shift from tactical account coverage to strategic outcome ownership
• Internal Account Management leadership pipeline maturity
• Business benefits realized from all transformation pillars tied to adoption success

REQUIRED EXPERIENCE

• 7+ years of experience in Change Management, Organizational Development, Training, or Account Management/Customer Success focused on the people and process side of transformation
• Demonstrated success leading change and adoption across multiple geographies and organizational contexts
• Proven experience with large-scale organizational transitions, system implementations, or restructuring including adoption and capability building
• Strong communication, facilitation, and relationship-building skills across leadership and frontline teams
• Ability to influence without direct authority across matrix teams and geographies
• Strategic thinking about how organizational readiness and adoption enable business outcomes

PREFERRED EXPERIENCE

• Background in Customer Success, Account Management, or Sales Operations transformation
• Experience with large-scale enterprise system implementations (CRM, customer management platforms)
• Exposure to global operating model unification or regional expansion programs
• Familiarity with change management frameworks (ADKAR, Kotter, McKinsey)
• Experience with AI adoption, digital transformation, or emerging technology change management
• Background scaling offshore or shared service models globally

CORE COMPETENCIES

• Strategic Change Leadership — Ability to think multi-year and build sustainable adoption capability across Account Management
• Communication & Engagement — Skilled at crafting and delivering messages across Account Managers, regions, and leadership levels
• Stakeholder Management — Building and maintaining relationships across Account Management, Implementation, Technology, and executive leadership
• Program & Portfolio Coordination — Managing multiple transformation workstreams simultaneously with dependencies
• Change Readiness & Assessment — Identifying adoption barriers and tailoring support strategies by region and segment
• Data & Performance Reporting — Using adoption metrics to drive decisions and demonstrate transformation impact
• Cultural Intelligence — Navigating and adapting to different regions and organizational cultures
• Continuous Improvement & Learning — Translating insights into organizational learning and scaled practices
• Coaching & Influencing — Developing Account Management leaders and change champions

REPORTING RELATIONSHIP

• Reports to: EVP of Customer Success
• Governance: Sits on (or advises) Customer Success Transformation Steering Committee
• Key Cross-Functional Partners: Account Management Leadership, Implementation Leadership, Customer Success PMO, Technology/IT, HR/Talent Management, Learning & Development, Finance

WHY THIS ROLE MATTERS

The success of Direct Travel's Customer Success transformation depends on far more than deploying new technology, migrating customers, or expanding geographies—it depends on building an Account Management organization where teams understand, embrace, and sustain those changes.

As Direct Travel executes the Account Management Growth Strategy (CRM implementation, global unification, AI-hybrid service delivery, team upskilling, and customer onboarding optimization), the PMO will deliver projects on time. But unless Account Managers are prepared, engaged, and confident in adopting new systems, processes, and ways of working, those projects will not drive customer adoption, revenue growth, or lasting business value.

This role ensures Customer Success has a dedicated strategic leader focused on the human and organizational side of transformation—engaging Account Managers, gathering frontline insights, building adoption capability, and driving sustained change so that every transformation initiative becomes operational reality and Direct Travel emerges as a customer-success-driven, transformation-ready organization.