Executive Advisor : Technology Transformation
About Highland
For 19 years, Highland has been a trusted and leading real estate agency across the Sutherland Shire, Eastern Suburbs, Inner West, and beyond.
With more than 200 team members across NSW and QLD, we operate across Residential Sales, Leasing, Property Management, Commercial, Project Marketing and Corporate Services.
As part of our continued growth, we are investing in a significant technology and business transformation agenda designed to improve scalability, productivity, customer experience and long-term enterprise value.
The Opportunity
Highland is seeking an experienced Executive Advisor: Technology Transformation & Portfolio Delivery to guide and report to the Executive Leadership Team in shaping and driving our transformation agenda.
This is a part time executive role expected to require two (2) days per weekwith flexibility to adjust based on requirements, workflow and results, suited to a seasoned transformation leader who has successfully delivered complex enterprise, operational or technology transformations and is looking for a high-impact, flexible engagement.
The role provides single-point accountability for transformation prioritisation, governance, investment oversight and execution, ensuring initiatives deliver measurable business outcomes rather than simply technology implementations.
Key Responsibilities
Enterprise Transformation Leadership
Develop and maintain a single enterprise transformation roadmap aligned to strategic priorities




Prioritise initiatives to maximise business value and eliminate duplication and low-value activities
Translate strategy into actionable plans with clear milestones and outcomes
Portfolio Governance & Investment Management
Establish governance frameworks, reporting and executive decision-making forums
Drive accountability for delivery, risks, dependencies and outcomes
Implement disciplined investment and prioritisation processes that align funding with business value
Delivery & Value Realisation
Lead and oversee execution of the transformation portfolio
Ensure initiatives achieve intended business outcomes across productivity, efficiency, customer experience and profitability
Monitor portfolio performance and proactively manage risks and roadblocksExecutive Advisory & Change Leadership
Serve as a trusted advisor to the CEO and Executive Team
Build alignment across business, technology, finance and operations
Drive a culture of accountability, execution excellence and continuous improvement
Ideal Candidate
You are a highly credible executive who combines strategic thinking with operational discipline and has a proven track record of leading large-scale transformation programs.
This role may suit a former:




Transformation Executive level
Portfolio Leader or Operating Partner
Senior Consulting Partner seeking a more operator-focused role
Transformation leader looking for a flexible, high-impact engagement
Experience Required
15+ years' experience leading technology, operational or enterprise transformation
Proven success delivering complex, multi-year transformation programs
Strong experience in portfolio governance, investment management and strategic prioritisation
Ability to influence and challenge CEOs, CFOs, Boards and senior stakeholders
Robust commercial, financial and value-realisation expertise
Exceptional leadership, communication and decision-making skills
Candidate Profile
A business leader first and a technology leader second
Strategic, pragmatic and outcome-focused
Comfortable making difficult prioritisation decisions
Highly credible with executive stakeholders
Accountable, influential and execution-oriented
Success Measures
Within ***** months, success will be demonstrated through:
A transparent and actively governed enterprise transformation roadmap
Improved prioritisation and alignment of technology investments
Effective governance and executive decision-making processes
Reduction in low-value or duplicative initiatives
Improved delivery predictability across major programs
Measurable business value realised from transformation investments
Strong executive confidence in the organisation's transformation execution capability
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📌 Executive Advisor: Technology Transformation (New South Wales)
🏢 HIGHLAND PROPERTY
📍 New South Wales