Practice Area
Digital experience strategy
Douglas Cirillo’s strategy work is deciding what a brand’s digital properties should do, building the team and the data to do it, and sequencing the work so it survives contact with the organization. He has done it as the person who built the function at Madison Square Garden, directed the rearchitecture at Sotheby’s, led digital product at Lindblad Expeditions and A Place for Mom, and, from Gangverk, led the History.com replatform whose architecture A+E Networks adopted as its migration standard.
What is digital experience strategy?
Digital experience strategy is the work of deciding what a brand’s website and apps should do, then building the team and the data to do it. The deliverable is not a deck. It is one set of metrics that matter, one shared understanding of the customer, and a sequence the organization can actually execute: what gets built, in what order, and how everyone will know it worked.
Technology decisions are only part of the strategy. The harder work is deciding what matters first, who owns it, what the organization can deliver, and how progress will be measured.
How I do it
Diagnose first. Start with an honest inventory: the platforms, the processes, and the team structure, and where each one is holding the work back. At MSG in 2015, my own written assessment named the problems plainly: disparate and antiquated systems, no unified strategic vision, tactical redundancy between properties, and reporting nobody could run a business on. At A Place for Mom, the visible problem was declining search performance; the actual problem was the platform and its governance. Effort was not the constraint. The foundation was.
Sequence the build. A roadmap balances visible wins that earn belief against the foundation work that makes the wins compound. My sequence is the one I still use: data foundation first, then the experience on top of it. Centralize measurement early, so every property reports the same way and arguments about priorities can be settled with shared numbers.
Start where proof is easiest. You do not align an organization by convincing everyone at once. Start with one team that is ready, ship something visible, show the value, and let other teams ask to join. The same logic applies to properties: at A+E, History.com went first, in four months, and became the reference model for what followed. Good alignment doesn’t start with consensus. It starts with proof.
Protect the roadmap by refusing. If you say yes to everything, the roadmap becomes a wishlist, and strategy turns into hope. A good no is tied to a clear roadmap, an outcome, or a constraint, and it is delivered early enough that everyone stays aligned. Prioritization is a standing practice, not a planning event.
Translate, and build it with them. The same roadmap has to be told four ways: marketing hears campaign conversion, sales hears lead quality, engineering hears fewer moving targets, leadership hears confidence that the work is not chasing the next shiny object. Translation isn’t a soft skill. It’s operational infrastructure. And the plan gets built with the people who will run it, because a strategy the team does not believe in does not ship.
I write about this in Alignment Isn’t a Meeting. It’s a System. and Prioritization Is About Saying No. This page is the record underneath them.
Where I have done it
Madison Square Garden. I built the digital product function and ran it as one operating model across 29+ websites and 4+ native apps. In 2015 I wrote the strategy to consolidate the site portfolio and retire the legacy platforms on a published schedule, and moved analytics into one repository so every property reported the same way. I proposed and led a $4M replatform and managed the operating and capital budgets behind it. Digital ticket sales for the Rockettes and Radio City Music Hall grew 400%. Read the case study.
Sotheby’s. With one direct report, I could not mandate change. I had to earn it. We started with one team, built with them, shipped visible wins, and let other teams ask to join. I ran the function through vendors, not headcount: one direct report, about 20 vendor staff, directing $5 to $6M in spend, and the rearchitecture was rebuilt around the data in about seven months. Organic traffic rose 167%, and the model and the stack still stand and have evolved since I left. Read the case study.
Lindblad Expeditions. I was recruited there by former MSG and Sotheby’s leaders. My team built the digital and data layer around a core systems migration rather than ahead of it, and within about eight months, with a 10-person team and a $5M portfolio, bookings rose 30%, booking funnel completion rose 82%, and qualified leads rose 40%. The rebuilt expeditions.com was named a Webby Honoree. Read the case study.
A Place for Mom. I diagnosed a sharp search decline as a platform and governance problem and led the rebuild of the content platform and its governance. I also had to build the team to run it: from 3 to more than 20 people in a year, internal and external, under one centralized delivery model, running a $6M annual portfolio. SEO market share rose from 26% to 68%, and the model and the stack still stand. Read the case study.
A+E Networks. From Gangverk, I partnered with A+E’s product and marketing leadership on a phased transformation: History.com first, relaunched in four months, then the A&E site. A+E adopted the architecture as its migration standard, which is what a phased strategy is for: the first build becomes the template, not the exception. Read the case study.
At Gangverk, I carried revenue targets and hiring authority and grew the client base from 1 to more than 60 across platform modernization programs. Read the case study.
The point
The functions built this way outlast the person who built them: the Sotheby’s and A Place for Mom models still stand, the A+E architecture became a migration standard, and former leaders have recruited me back three times.