25 Years
Inside.
Now For
You.

For 25 years, Kevin Cartwright built a career inside the managed services industry — not on the periphery, but at the commercial centre of how large managed services engagements are won, structured, and priced.

That career spanned every major category of managed services: infrastructure and cloud, cybersecurity and managed security, network and connectivity, help desk and end-user support, CCaaS and customer experience, business process outsourcing, and the emerging category of managed AI services. It included engagements at every scale, from mid-market organisations running their first outsourcing process to enterprise organisations managing multi-tower, multi-geography managed services portfolios worth hundreds of millions of dollars.

The work was commercial at its core. Building pursuit strategies. Designing commercial models. Structuring ARC/RRC frameworks and deadband positions. Negotiating BAU/project boundaries. Designing SLA frameworks that protected vendor margin while appearing to protect buyer interests. After more than 1,000 RFP responses across that career, Kevin understood the managed services commercial landscape from the inside — including the parts that vendors are careful not to explain to buyers.

The decision to move from vendor side to buyer side wasn't a sudden one. It came from years of watching organisations navigate managed services procurements with a fraction of the commercial knowledge that their vendor counterparts brought to the table.

Buyers entering a managed services negotiation are typically running their first or second outsourcing engagement. The vendor across the table has run hundreds. That asymmetry produces predictable outcomes: commercially disadvantageous contracts, poorly designed SLAs, undefined BAU/project boundaries that generate years of disputes, and transition plans that set up failure before the ink is dry.

The knowledge required to change those outcomes exists — it just sits on the wrong side of the table. Moving to the buyer side meant taking that knowledge and putting it where it could actually protect the people who needed it most.

The Managed Services Buyer's Playbook emerged from a simple observation: the commercial knowledge that vendors accumulate over thousands of engagements has never been written down for buyers. The books that exist on managed services procurement focus on process — how to run an RFP, how to evaluate vendors, how to structure a governance model. None of them explain how vendor commercial models actually work, where the margin recovery happens, or what the contractual traps look like from the inside.

The guide covers all seven major managed services categories across 18 chapters and includes a 16-file working toolkit — checklists, calculators, frameworks, and templates that buyers can use directly in live procurement engagements. It is the guide that changes the information balance.