Douglas Cirillo | Head of Digital Experience and Growth

Douglas Cirillo is a digital experience and product leader whose work spans travel, media, live entertainment, and consumer services. He has led digital product, experience, data, and growth initiatives at Vanguard, Lindblad Expeditions, Sotheby’s, Madison Square Garden, A Place for Mom, and Gangverk.

About

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.

The record

Lindblad ExpeditionsDigital product leader

Bookings up 30 percent and booking funnel completion up 82 percent, pre against post replatform, within eight months. Qualified leads up 40 percent. The rebuilt expeditions.com was named a Webby Honoree. Led a 10-person team and a $5M portfolio across product, analytics, design, and partners. Read the Lindblad case study.
Sotheby’sDigital product and growth stack

Organic traffic up 167 percent, on-site search click-through up 48.7 percent, consignment landing pages that doubled search placement and cut consignment ad spend 50 percent. The customer data and measurement foundations established there continued to support the business after his departure.
Madison Square GardenBuilt and ran digital product

Built the digital product function and ran it for four years, 29+ websites and 4+ native apps, including the MSG GO app, Emmy-nominated. Grew digital ticket sales 400% for the Rockettes and Radio City Music Hall.
Gangverk and A+E NetworksMarketing and product strategy

Replatformed History.com end to end in four months; A+E adopted the architecture as its standard for migrating its web ecosystem. Grew the firm’s active clients from 1 to 60+. Carried revenue targets and hiring authority. Consulting work included a Segment-sponsored engagement with TripAdvisor on customer data platform adoption. Read the A+E case study.
A Place for Mom

Organic share of demand grew from 26 percent to 68 percent; team grew from 3 to more than 20.
VanguardCurrent role

Head of Digital Experience and Growth at Vanguard, leading a function supporting Personal Wealth marketing and the retail business. Building since February 2026.

What I work on

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. What gets built, in what order, and how the organization knows it worked.

Composable martech and customer data

Composable martech is a stack built from best-of-breed tools, connected through a warehouse-first customer data platform, instead of a single vendor suite. Warehouse-first foundations, CDPs, and decisioning built to test against the objective, not the screen.

Experimentation and measurement

Tests aimed at a specific outcome, with definitions a whole company can agree on.

AI readiness and answer discoverability

How brands make their content and data useful to both people and AI agents.

Writing

Observations from the Middle Seat

Essays on building digital functions, data first and AI second, and the human side of leading the work. New essays every two weeks, mirrored in From the Middle Seat on LinkedIn.

Selected writing

Own Your Harness: Why owning your data, runtime, and gates matters more than the model underneath, and the three checks I run before I trust any agent setup.
Data First, AI Second, Now With Agents As The Proof: Agents do not fix messy data, they expose it. Govern the data first, then let AI scale it.
What a Customer Data Platform Actually Is (and Isn’t): A CDP is a product, not a project. What one actually is, and why the definition has to come before the tool.

Read on Substack From the Middle Seat on LinkedIn

Elsewhere

The best way to reach Douglas is through LinkedIn or Substack.