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LeWinter Advisory
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IT & Business Transformation Advisory

Assessment and advisory that sets direction for major technology programs. IT assessments, software evaluation and selection, operating model uplift.

The worst transformations I’ve seen were the ones that skipped the honest assessment and went straight to vendor selection.

When I come in. Before the RFP goes out, or after a stalled program has lost the room. We look at the business outcomes you’re after, the capability gaps that actually block them, and the shortest path between the two. Deliverables are opinionated. If the right answer is to buy, I say buy. If it’s to build, I say build. If it’s to stop and fix operations first, I say so and explain why.

What you get.

  • IT assessment across business transformation, security and compliance, or infrastructure
  • Enterprise software evaluation: requirements, shortlist, scored vendor comparison, negotiation support
  • Operating model recommendations with a capability uplift plan
  • Executive-level written positions you can hand to the board

Who this is for. CEOs, CFOs, and CIOs at mid-market firms deciding between major platforms, restructuring IT operating models, or trying to unstick a transformation that has lost momentum.