Oliver Giles
I’m an Australian-American Technical Program Management and PMO leader with 20+ years of experience building governance and delivery frameworks for high-growth SaaS/PaaS companies and complex government environments.
About
I’m an Australian-American Technical Program Management and PMO leader with 20+ years of experience building governance and delivery frameworks for high-growth SaaS/PaaS companies and complex government environments. I’ve stood up PMOs from scratch, put rigorous portfolio planning and risk/issue dependency management in place, and coached cross-functional teams (often across Agile and Waterfall ways of working) to deliver against demanding roadmaps and executive commitments.
I’m especially proud of delivering enterprise-scale programs—coordinating up to 36 Scrum teams across $140M+ portfolios—while also leading M&A due diligence and post-acquisition integrations that align technical roadmaps, teams, and governance. I bring a balance of hands-on program leadership (including executive/board reporting) and practical delivery execution, with deep experience across technology, healthcare, energy, insurance, defence, and government stakeholders.
- 27 years' experience
- Joined December 2025
Industry experience
- Government
- Professional Services
- Software & Internet
- Healthcare
- Energy & Utilities
- Transportation & Logistics
- Financial Services
- Non-Profit Organization
- Other
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Work experience· 18 roles
• Completed a 6-month contract leading the merger of two start-ups and an AI, CRM and online marketing solutions delivery team through planning, development, testing, deployment and support phases for small to medium-size businesses across Australia and New Zealand, spanning numerous industry niches. • Recruited, managed and coached an engineering and business operations team of 15 staff, and governed execution and continuous improvement of a structured training and coaching program for Aussie entrepreneurs learning to set up and run their own AI Agencies. • Managed projects and all client interactions thru an end to end to build, integration and deployment of AI bots and tailored CRM solutions with Twilio numbers into existing tech stacks for over 20 customers. • Reported to two young founders, providing executive coaching, surfacing risks/issues/trade-offs, and making operational delivery and business process improvement decisions across the company.
Led a 6-month merger of two start-ups and an AI/CRM/online marketing delivery team. Recruited and coached an engineering and business operations team of 15, governed a structured training/coaching program for Australian entrepreneurs, and managed end-to-end delivery for AI bots and tailored CRM solutions (including Twilio-number integration) across 20+ customers. Provided executive coaching to founders, surfaced risks/issues/trade-offs, and made operational delivery and process improvement decisions.
Sold home, moved family of five from California to New South Wales, purchased new home, and then looked for new employment
Education
Certifications and awards· 8
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