Portfolio Technology Advisory
Ongoing technology advisory across the portfolio. Regular operating reviews, board-level risk reporting, and pattern recognition across holdings.
What You Get
- Monthly portfolio technology operating reviews
- Board-ready technology risk and progress reporting
- Cross-portfolio pattern recognition and best practice transfer
- Vendor negotiation support and leverage
- Technology leadership coaching and succession planning
How It Works
Portfolio advisory is built on pattern recognition. Jon's experience across dozens of organizations makes recurring failure modes visible before they become expensive. Regular operating reviews surface problems while they are still manageable.
Board-level reporting translates technology progress into investment language. Not uptime percentages and deployment counts, but EBITDA impact and risk reduction.
Engagement Models
Four structures, each matched to a different stage of the investment lifecycle. The model adapts to what you need.
Diligence
Fixed-feePre-close technical assessment scoped to the deal timeline. Deliverable is an independent technology risk and opportunity report.
Typical: 2-4 weeksValue Creation Sprint
30-100 day engagementPost-close execution sprint converting diligence findings into measurable progress. Quick wins in 30 days, structural changes by day 100.
Typical: 30-100 daysPortfolio Advisor
Monthly retainerOngoing technology advisory with regular operating reviews, board-level reporting, and cross-portfolio pattern recognition.
Typical: 6-12 month commitmentOperating Mandate
Interim or embeddedFull CTO or VP Engineering authority with operational accountability. Jon sets strategy, shapes architecture, makes decisions, drives execution, and remains accountable for the consequences.
Typical: 3-12 monthsStrengthen Portfolio Technology Oversight
Ongoing operating reviews, board-level risk reporting, and cross-portfolio pattern recognition from someone who has operated the systems, not just evaluated them.
Discuss Portfolio Advisory