Context
The client was an OSHC provider that had grown from a fast, entrepreneurial startup into the state’s largest provider of outside school hours care other than the State Government. Growth had created scale, visibility and opportunity, but the business systems, technology foundations, management practices and people capability had not matured at the same pace.
The engagement became a business and systems transformation across leadership, HR, operations, finance, technology, reporting, compliance, stakeholder management and executive decision support.
Problem
The organisation had outgrown the informal operating model that had helped it move quickly as a startup. Systems and people were under strain. Knowledge was spread across individuals, spreadsheets, manual routines, cloud tools, inconsistent practices and vendor-dependent support models.
Technology foundations were also not fit for the scale of the organisation. Some services were operating from basic Chromebooks and mobile-phone tethering rather than enterprise-grade networks, identity controls, managed devices and stable site connectivity. That limited reliability, supportability, reporting and confidence across multi-site operations.
The people challenge was just as important as the systems challenge. The business needed capability uplift, role clarity and leadership maturity. Some people could be retrained into the next stage of the organisation; other roles and structures needed to change. HR management, restructuring, workforce decisions and leadership support became central to the transformation.
Benjamin’s Role
Benjamin served as the organisation’s fractional CIO from 2018 through to 2025. During that period he provided technology leadership, systems strategy, Microsoft 365 implementation, vendor guidance, account governance, reporting direction and practical executive support as the organisation grew.
From 2022 to 2025, the engagement became much heavier. Benjamin took on additional responsibility across business transformation, operating-model reform, HR management, reporting, vendor remediation, compliance support, executive decision-making and strategic planning.
For approximately 18 months, Benjamin also acted as interim CEO. That period required practical leadership across people, systems, operations, finance, stakeholder relationships, compliance pressures and business continuity while transformation work continued.
The role was hands-on executive leadership. Benjamin designed systems, managed people issues, reshaped operating practices, implemented technology, worked with stakeholders and built the capability needed for the organisation to keep operating without permanent consultant dependency.
What Benjamin Built Or Changed
- Implemented Microsoft 365 from the beginning as the organisation’s enterprise productivity, identity, collaboration and governance foundation.
- Built SharePoint, Teams and Microsoft 365 operating practices to support document control, communication, account lifecycle management and business process maturity.
- Transformed the technology environment from basic Chromebook and iPhone-tethered arrangements into a more enterprise-grade operating environment.
- Introduced site-to-site WAN/VPN thinking and stronger network foundations for multi-site operations.
- Improved device, account, access, backup, cybersecurity, vendor and business-continuity practices.
- Supported Power BI reporting, report specification work, data warehouse planning and structured management visibility.
- Reduced reliance on uncontrolled spreadsheets by moving recurring information needs toward governed datasets and repeatable reporting.
- Supported utilisation, compliance, vacation-care, operational and management reporting patterns.
- Led HR-heavy transformation activity including role clarity, retraining, restructuring, workforce management and leadership support.
- Developed five-year forward strategic plans and began implementing them with the people who would remain in the roles to execute the vision.
- Supported organisational reform and operating-model maturity so the five-year plans were connected to practical systems, people and governance changes.
- Reworked vendor accountability and service ownership without turning the public case study into a vendor dispute record.
Stakeholders
Board and executive stakeholders, SA Government stakeholders, the Education Standards Board, school leadership, school governing councils, operations leaders, finance, HR, compliance, educators, site teams, families, contractors, ICT providers, reporting users and external service providers.
Delivery Approach
The approach combined executive leadership with practical systems delivery. Benjamin connected business questions to people, systems, datasets, workflows and governance controls, then used those controls to make recurring management decisions easier to support.
The technology work was deliberately tied to operating maturity. Microsoft 365, SharePoint, Teams, Power BI, data warehouse planning, account lifecycle controls, network uplift, vendor management and reporting were framed as parts of the same transformation problem: who owns the work, who can see the truth, who can act on it, and how the organisation keeps performing as it grows.
The people work was equally direct. The business needed a workforce and leadership structure that matched its size and regulatory obligations. The transformation therefore required retraining where possible, restructuring where necessary, and clear management of roles, performance, accountability and communication.
Outcomes
The engagement improved executive visibility, reporting maturity, account governance, vendor accountability, technology reliability and decision support. It created clearer practices for managing information, reporting, access, operational risk, business continuity and multi-site technology foundations.
The work shifted the organisation from startup-style dependency on informal knowledge toward a mature operating model. Systems became more supportable, reporting became more structured, Microsoft 365 became a foundation for collaboration and control, and network and device arrangements moved toward enterprise expectations.
The HR and leadership work aligned people capability with the organisation’s scale. Staff and leaders were developed where capability uplift was viable, and structural changes were made where roles or behaviours no longer matched the business the organisation had become.
Benjamin stepped away once the five-year forward strategic plans had been developed and implementation had begun with the people who would remain in place to execute the vision. By that point, the organisation had a stronger operating base and a clearer path for ongoing execution.
What It Demonstrates
Fractional executive leadership, interim CEO capability, HR-heavy transformation, enterprise systems uplift, Microsoft 365 implementation, multi-site network maturity, reporting governance and the ability to transform both business systems and people capability in a regulated operating environment.