UnionSquare Digital

Build, fix, and scale digital businesses.

UnionSquare Digital helps founders, CEOs, investors, and leadership teams sharpen strategy, accelerate growth, improve marketing performance, and turn complex digital businesses into focused, measurable, scalable operations.

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Operating lens

Strategy

Growth

Marketing

Digital products

Subscriptions

Analytics

Led by Rory Cumming, a founder, CEO, advisor, and digital business operator with more than two decades of experience across consumer, subscription, media, technology, and emerging climate and blue-economy ventures.

What we do

Senior strategy and execution support for digital businesses.

UnionSquare Digital works where strategy has to become operating progress: sharper choices, better systems, clearer messaging, stronger marketing, and measurable growth.

Business & Growth Strategy

Clarify the market opportunity, sharpen positioning, define the growth plan, and align the organization around what matters most.

Marketing Strategy & Execution

Build practical, measurable marketing systems across acquisition, retention, analytics, messaging, campaigns, and go-to-market execution.

Digital & Subscription Businesses

Launch, improve, and scale digital products, subscription services, consumer platforms, marketplaces, and direct-to-consumer offerings.

Fractional Leadership & Advisory

Provide senior operating support for founders, CEOs, boards, and investors when a company needs experienced leadership but not a permanent executive hire.

Where we help

For moments when the business needs focus, judgment, and momentum.

A startup has product traction but needs sharper positioning, go-to-market strategy, or investor-ready growth plans.

A consumer or subscription business has stalled growth and needs to diagnose acquisition, retention, pricing, or funnel problems.

A media, publishing, or information business needs help developing new digital revenue streams.

A climate, cleantech, or blue-economy company needs practical business, marketing, and commercialization strategy.

An established company is launching a new digital initiative and needs startup-style focus and execution discipline.

An investor or board needs an experienced operator to assess a business, support a portfolio company, or pressure-test a plan.

How we work

Diagnose. Focus. Execute.

UnionSquare Digital does not deliver abstract strategy decks that sit on a shelf. The work is designed to become decisions, priorities, operating plans, campaigns, dashboards, investor narratives, and organizational momentum.

Diagnose

Understand the business, market, customer, data, economics, team, and constraints.

Focus

Identify the few decisions and actions that will matter most.

Execute

Build the plan, operating cadence, messaging, systems, metrics, and team alignment needed to move.

Sectors

Focused on digital, consumer, media, subscription, and emerging climate markets.

Digital Consumer Businesses Subscription & Membership Models Media, Publishing & Information Products Startups & Growth-Stage Companies Climate Tech, Cleantech & Blue Economy Martech, Analytics & Marketing Operations

About Rory

Operator, advisor, strategist, and builder.

Rory Cumming is the Founder and Principal of UnionSquare Digital. He has spent more than two decades building, leading, advising, and improving digital businesses, with experience spanning business strategy, marketing, P&L leadership, subscription models, analytics, product development, and high-performing teams.

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Need senior help turning complexity into a clear growth plan?

Whether you are launching something new, fixing what is not working, or preparing for the next stage of growth, UnionSquare Digital can help define the path and build the operating plan to get there.

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