Speaking and Media
Speaking and media
Douglas Cirillo is Head of Digital Experience and Growth at Vanguard and a digital product leader whose work spans travel, media, live entertainment, and consumer services. His work focuses on building digital and data functions, establishing customer data foundations, and connecting experience decisions to measurable outcomes. He writes Observations from the Middle Seat and is available for selected speaking and media engagements. He is based in West Chester, Pennsylvania, outside Philadelphia.
The talk
In September 2019, Douglas Cirillo and Richard McGovern presented “How Sotheby’s Transformed a 275-Year Old Company into a Data Innovator” at Synapse, Segment’s conference. The session was also presented at Gartner.
Session abstract (2019): “Learn how Sotheby’s, the global leader in art and luxury commerce, replaced a legacy data ecosystem with one that supports data-driven decision making and scalability. In this session, Douglas Cirillo and Richard McGovern will discuss how the 275-year-old auction house approached digital transformation and established a unified data infrastructure that provides greater integration between platforms and systems, more actionable insights, and deeper consumer personalization.”
Watch the recording on YouTube (26 minutes).
Topics
Each topic is one he has already written about in public; the links are the receipts.
Data first, AI second. Why AI programs fail on weak data foundations, and what to build first. Read the essay.
Own your harness. Governing AI agents and the parts of the stack you actually control, instead of renting your whole operation from vendors. Read the essay.
Composable martech and customer data platforms. Packaged CDP versus warehouse-native, how to choose, and what it takes to run one. Read the practice page.
Outcome-based testing. Tests aimed at a specific outcome, with definitions a whole company can agree on, and decisioning built to test against the objective, not the screen. Read the practice page.
Building a digital function that outlasts you. Build with the people who will run it, and let durability be the test. Read the essay.
Search is experience. Organic search, generative answers, and how brands get found when the customer’s agent comes asking. Read the essay.
Strategy and letting go. Deciding what not to build, disagreeing and committing, and leading the people side of a platform change. Read the essay.
Available for selected conference sessions, panels, podcast conversations, guest lectures, and editorial contributions.
The record behind the topics
Lindblad Expeditions: bookings up 30%, booking funnel completion up 82%, qualified leads up 40% within about eight months; the rebuilt expeditions.com was named a Webby Honoree. Sotheby’s: organic traffic up 167%, search click-through up 48.7%. A Place for Mom: SEO market share from 26% to 68%. Madison Square Garden: one operating model across 29+ websites and 4+ native apps over four years; MSG GO was a New York Emmy nominee for Technical Achievement; digital ticket sales for the Rockettes and Radio City Music Hall grew 400%. A+E Networks: History.com replatformed in four months, and A+E Networks adopted the architecture as its migration standard. Gangverk: client brands from 1 to 60+.
Bio
Short bio. Douglas Cirillo is Head of Digital Experience and Growth at Vanguard. He has built and run digital and data functions at Madison Square Garden, Sotheby’s, Lindblad Expeditions, and A Place for Mom, and led marketing and product strategy at Gangverk. He writes Observations from the Middle Seat on Substack.
Full bio. I build digital and data functions at audience brands, then run them. I am Head of Digital Experience and Growth at Vanguard, where I lead a function supporting Personal Wealth marketing and the retail business. Before Vanguard, I led marketing and product strategy at Gangverk, was Vice President of Digital Product Management at A Place for Mom, directed digital product at Lindblad Expeditions, ran digital product and the growth stack at Sotheby’s, and built and ran digital product at Madison Square Garden. The pattern across those seats is consistent: build with the people who will run it, put the data foundation first, measure against outcomes, and leave something that still stands after you leave the room. Former leaders have recruited me back three times. I write Observations from the Middle Seat. My degree is a BA in Journalism from Susquehanna University, with an MBA from Seton Hall. I started college on a computer science track and switched when the dot-com bubble burst, which explains a career spent half in the build and half in the story.
Headshot and contact
Download the full-resolution headshot.
For speaking, podcast, and media requests: douglas.cirillo@gmail.com. He is also on LinkedIn and writes Observations from the Middle Seat.