Matthew Holman

Subscriptions Leader: Consultant, Newsletter, Podcast | Events | Communities | Commerce Catalyst | Partnerships @QPilot | Formerly Incarcerated

Most people don't see subscriptions the way I do.

For many of the brands I come into contact with, subscriptions are about retention. Figuring out how to keep people longer to drive up lifetime value (LTV).

But subscriptions are much more than LTV and recurring revenue. They are a way to engage with your best customers, provide more value, and capture more value in return. When looked at through an acquisition lens, subscriptions become less about retention and more about customer experience.

That's what we do at Subscription Prescription - craft acquisition and retention experiences to unlock greater profitability and sustainability for your business.

Message me to learn more about how we can improve acquisition of subscribers, retention of subscriber, and the profitability of subscribers with our approach. Unlock new growth for your business with the right prescription for your subscriptions.

Partner, Cofounder

Patterns in the Cloud builds fun software for commerce

Probably our biggest event to this point outside of our conference.

In case you've wondered what we're covering, agenda is live:

We're putting experts on stage, combined with the ability to meet and learn from your peers in the afternoon. This day is PACKED with learning.

9am - 9:30am: Welcome, coffee, breakfast snacks ☕ 

9:30am - 10am: Jon Ricketts, from EKOM AI, on how brands are prepping landing pages for agentic commerce and how to show up correctly in AI search.

10:00am - 10:30am: Nate Larkin, from Gladly, and Nancy Orgill from KÜHL Clothing Company, break down how AI can either win a customer or lose one for you.

10:30am - 11:00am: Van Oakes, from Goat Media, on how he's leveraging AI across the acquisition funnel for brands like Diesel Power Gear, Minky Couture, and Everyday Dose.

11:00am - 11:30am: Matthew Schmitt, from Shoperator, on how AI is creating massive scale for static ad creation.

11:30am - 12pm: Drew Clary, from TIDLOS supplements, shows how his small brand has built its own Enterprise-grade AI solutions (yes, plural) on a shoestring budget.

12:00pm - 12:30pm: Panel discussion with Stephanie Hileman from 1800 Contacts, Steve Clark from Spoonful of Comfort, and Nick Christensen from GIMME Beauty on how brands are evaluating and implementing AI right now in their orgs.

12:30pm - 1:30pm: LUNCH 🥘 

1:30 - 3pm: Networking and chance to speak more with our speakers and sponsors

Happening in Lehi, Utah on January 20th.

If you don't have your ticket left, we are at 80% capacity right now. Grab a ticket now: https://luma.com/jvwnjkbb

D2C Subscription Agency | Weekly Subscription Tips --> Newsletter + Podcast | Commerce Catalyst Community | Partnerships @QPilot

Amazon Ads Tech Evangelist | Amazon Ads | Keynote Speaker |

All opinions are my own.

I'm passionate about one thing: helping brands navigate the transformation of commerce media. As Chief Business Development Officer at Skai, I'm focused on connecting the ecosystem—brands, agencies, retailers, and publishers—around the next era of omnichannel, AI-powered advertising.

What drives me: Commerce media is at a turning point. The last decade built retail media foundations. The next decade will be defined by omnichannel integration, agentic AI transformation, and the emergence of programmatic commerce media. I'm here to help shape that future.

My approach: I believe in the power of community and partnerships. At Amazon Ads, I pioneered partner-first strategies that unlocked hundreds of millions in new advertising investment. I've seen firsthand how translating complex technology into actionable insights creates breakthrough moments for brands and their agency partners.

What I bring: Deep ecosystem relationships built through 60+ global speaking engagements, 600+ industry insights, and direct collaboration with strategic partners worldwide. I understand the challenges enterprise brands face as they navigate omnichannel commerce—from fragmented data to walled gardens to the promise and complexity of AI.

My mission: To accelerate the future of commerce media by fostering the partnerships and innovations that unlock growth for everyone. Whether it's championing new solutions, building communities, or translating emerging trends into practical strategies, I'm committed to helping our industry evolve.

The transformation ahead is massive. The opportunity is even bigger. Let's shape it together.

Specialty Skills: 
Inspirational Leadership, Change Agent, Strategic Thinker, Project Manager; Digital Marketing, E-Commerce Solutions, Advertising, Social Media, SEO/SEM, Online User Experience, Website Design; P&L, Budgeting, Contract Negotiations, Vendor Relationships, Customer Service, Major Account Management, Market Penetration, Start-Up Operations, Mulit-Channel 3rd Party Sales Management

Proficient in Amazon MWS, Agile, Scrum and Jira methodologies, along with Google Docs, Adwords & Analytics, MS Office Suite, MailChimp, ConstantContact, and many related applications on Windows and Macintosh platforms.

Jeffrey Cohen

The Retail Media Reckoning Is Here, And the Performance Gap Is Widening.
Retail media isn't slowing down. But here's what should keep you up at night: the gap between leaders and everyone else is getting wider, not narrower.

Get the full report now:https://okt.to/dmzO58

Skai partnered with Stratably to survey 166 brand and agency marketers and conducting 40+ in-depth interviews with retail media leaders. We found one truth that became crystal clear: retail media has reached an inflection point.

What Separates Winners from the Pack: 7 in 10 brands report meeting or exceeding retail media goals. Sounds promising, right? But dig deeper and you'll find only 15% have strong measurement confidence. The rest are flying blind, pouring budget into a channel they can't fully validate.

Here's what leaders do differently:
→ They've moved beyond Amazon-first strategies to true omnichannel orchestration
 → They treat retail media as infrastructure requiring systematic discipline, not just another tactic
 → They're shifting GenAI investment away from creative toward campaign management and analytics
 → They've built measurement frameworks that steer real-time decisions, not just post-campaign reports

The Uncomfortable Truths
52% of advertisers are reallocating display budgets to retail media DSPs, the biggest shift in programmatic since its inception. Why? Closed-loop attribution that open web simply can't match.

Brands plan to manage 8+ retail media networks by end of 2026, yet only 12% have integrated media and commerce operations. That's not scale, that's a coordination crisis waiting to happen.

75% cite incrementality as their biggest measurement challenge, but only 20% can actually act on those insights. The infrastructure isn't keeping pace with the ambition.

The winners in 2026 won't be those with the biggest budgets. They'll be the ones who've built the operational foundations to execute at the speed retail media demands. 

That means:
⚫ Unified platforms that normalize performance data across fragmented networks
⚫ Systematic incrementality measurement that moves from dashboard to decision engine
⚫ Strategic AI deployment focused on performance optimization, not just efficiency gains
⚫ Cross-functional alignment between media, commerce, and sales teams

The retail media opportunity is massive. But without the right infrastructure, that opportunity becomes a liability, more networks, more budget, more complexity, but no clearer path to sustainable growth.

Get the full report now:https://okt.to/dmzO58

A sincere thank you to the incredible speakers who joined me for the launch event and shared their insights: Russ Dieringer (Stratably), Jenna Levin (Colgate-Palmolive), Lauren L. Lavin (WPP Media), Sonya Hober (Walmart Connect) Nich Weinheimer and Yoav Izhar-Prato. Your perspectives made this research come alive in ways data alone never could.

Chief Business Development Officer at Skai | Ex-Amazon Ads Tech Evangelist | Commerce Media Thought Leader

The Most Honest Thing I Heard at CES: “We think we know what's next, but we really have no clue”

CES 2026 felt different than any show I’ve attended. Not different in the “ooh, shiny new tech” way. Different in a way that made me uncomfortable.

When I think about 2026, I think about the year of uncertainty.

The Uncomfortable Truth

I had dozens of conversations with brands about AI shopping. About Rufus adoption increasing. About Google’s AI shopping engine and ChatGPT’s commerce capabilities. Everyone agreed usage is growing.

But when I asked for the data that proves it? They point to general states or something that “they” said, but nobody knows who “they” are! 

That repeated across conversation after conversation, telling you everything about where we are right now.

Fear Isn’t Weakness. It’s Wisdom.

This uncertainty is creating real fear and doubt:

- Fear you’ll invest in the wrong AI
- Doubt you’re spending energy in the right places
- Fear you’ll miss the boat when the industry shifts

Let me be clear: If you’re NOT uncertain right now, you’re not paying attention.

How Do You Prepare for the Unknown?

My recommendation: Stick with the tried and true while being nimble and looking around corners.

Foundation (70-80%): Don’t abandon what’s working. Core retail media delivering proven ROAS. Established measurement. Product content fundamentals.

Future (20-30%): Allocate budget to experimentation. Build measurement frameworks when platforms can’t provide data yet. Partner with technology providers who have cross-client visibility.

The irony? Uncertainty requires MORE strategic planning, not less.

You Need Tools AND Strategy

Brands need AI. No question. We’re seeing it internally at Skai, massive productivity gains in development, increased Celeste adoption driving budget efficiencies.

The tools work.

But here’s what everyone’s missing: Tools without strategy is just expensive chaos.

You need BOTH:

- Tools for an AI world: Automation, optimization, speed
- Strategy for your brand in an AI world: Where to play, how to measure, when to act

One without the other? You’re either moving fast in the wrong direction or thinking strategically but unable to execute.

The Real Lesson

CES used to be about certainty. CES 2026 was about acknowledging we’re in transition.

The brands that will win aren’t the ones who figured it all out first. They’re the ones building adaptable systems, not rigid plans. The ones who can act despite uncertainty, not paralyzed by it.

Because here’s the truth: This uncertainty isn’t going away in Q2. Or Q3. Or probably even 2027.

We’re in a multi-year transformation of how commerce happens. AI isn’t a feature release,it’s a fundamental rewiring of how consumers discover, evaluate, and purchase products.

The question isn’t “when will we have certainty again?”

The question is “how do we build businesses that thrive in uncertainty?”

That’s the real theme of CES 2026.

Last chance, only one week out, and I'm looking forward to this conversation.

Next Tuesday (Jan 13) in NYC, we're unveiling Skai's State of Retail Media report with some folks who are deep in the trenches of this space every day.
What makes this different? We're not just sharing data, we're breaking down what it actually means for your 2026 planning.

Russ Dieringer and I will walk through the biggest shifts we saw in 2025. Then Jenna Levin (Colgate-Palmolive) and Lauren L. Lavin(WPP Media) join us to discuss how brand and agency perspectives are evolving in response to these changes.

The retail media landscape is more fragmented than ever. Budgets are under scrutiny. Attribution is messy. This is the kind of conversation where the real insights happen after someone says "here's what we're actually seeing..."

If you're in NYC and want to be part of it, there are still a few spots available. Sign up now: https://lnkd.in/gTWGC43q 

See you next week.

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Matthew Holman

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The Battle

Matthew Holman

Jeffrey Cohen

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Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Matthew Holman's LinkedIn Performance

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