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 week with 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, adaptable 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 roadblocks

Executive 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
- Strong 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 12-18 months, success will be demonstrated through:

- A clear 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