The customers that got your brand to its current size may not be the customers who take it to the next stage of growth.

This week, Jordan is joined by Pilothouse’s Rafael Gi to break down a pattern they’re seeing across brands at very different stages: the customer base, acquisition strategy, and messaging that once worked can eventually become a ceiling.

They walk through three real brand scenarios, including a skincare company where 80% of free-sample buyers never purchased again, a sports brand that had outgrown its parent-focused positioning, and a sunglasses brand seeing its higher-AOV customer segment grow while its traditional core market declined.

Jordan and Raf discuss how to spot these shifts early, what your new-to-repeat customer mix can tell you, why revenue per email sent matters, how acquisition platforms get trained on the customers you attract, and how to realign your ads, website, and retention strategy around the customers with the most future value.

In this episode:

• How to tell when you’re marketing to the wrong customers
• Why growing brands can outgrow their original customer segment
• The danger of training Meta and Google to find discount buyers
• Why 80% of one brand’s free-sample customers never purchased again
• How to analyze new vs. repeat customer cohorts
• Revenue per email sent as an early warning signal
• Matching PDP messaging to the audience landing there
• How to shift toward a more valuable customer segment without losing your existing base

01:22 Why your current customers may be holding back your next stage of growth

03:39 Three brands facing the same customer-segment problem

08:00 How to tell when you’re marketing to the wrong people

09:29 Using Shopify cohorts to diagnose customer quality

10:27 Revenue per email sent as an early warning signal

11:52 When your PDP is speaking to the wrong customer

16:39 How discount acquisition can train Meta and Google on the wrong buyers

20:57 When a higher-value customer segment starts replacing your core market

Work with Pilothouse: ⁠https://www.pilothouse.co/get-in-touch?utm_source=dtc&utm_medium=podcast&utm_content=e&rPodcast⁠

Subscribe on YouTube: ⁠https://www.youtube.com/@DTCPodcast

Subscribe to DTC: ⁠https://www.directtoconsumer.co/⁠

Listen to DTC Podcast: ⁠https://podcasters.spotify.com/pod/show/dtcpodcast

Jordan is in the middle of rewarming an email account that Gmail was sending straight to spam, so this week he’s taking you inside the process.

He breaks down what damaged the account’s sending reputation, the engagement segments he’s using to rebuild it, why static send size matters during a rewarm, and how he’s using Gmail-specific data, GlockApps, and Postmaster Tools to tell when it’s safe to scale back up.

Jordan also explains why your reported email revenue may be inflated by Apple Privacy Opens, why list size is one of the most misleading metrics in email, and what brands should watch before a struggling program gets this far.

In this episode:

• The email trilemma: traffic, inboxing, and list growth
• What 100% Gmail spam actually means
• The segments Jordan uses during a rewarm
• Why engaged senders should ramp volume slowly
• The problem with Apple Privacy Opens and email attribution
• Why prospect-only campaigns can hurt engagement
• How to use Google Postmaster Tools during recovery
• When to start expanding your audience again

If your email performance looks healthy on paper while clicks and inbox placement tell a different story, this episode shows you where to look.

01:24 Why this email account needs a rewarm

02:22 The email trilemma: traffic, inboxing, and list growth

05:13 Inside an account hitting 100% Gmail spam

08:08 How Apple Privacy Opens can inflate email revenue

11:05 The exact segments Jordan uses to rewarm an account

14:02 Why static send size matters during a rewarm

20:54 GlockApps, Gmail segments, and Google Postmaster Tools

24:12 Using high-engagement promos to rebuild sending reputation

Work with Pilothouse: ⁠https://www.pilothouse.co/get-in-touch?utm_source=dtc&utm_medium=podcast&utm_content=e&rPodcast⁠

Subscribe on YouTube: ⁠https://www.youtube.com/@DTCPodcast

Subscribe to DTC: ⁠https://www.directtoconsumer.co/⁠

Listen to DTC Podcast: ⁠https://podcasters.spotify.com/pod/show/dtcpodcast

Jordan has a new favourite email program, and it breaks a lot of the rules marketers usually follow.

In this episode of The World’s Best Email and Retention Podcast, Jordan breaks down Dôen’s email program, from its layered photo grids and behind-the-scenes creative to tiny copy, cursive fonts, and understated CTAs.

The program assumes its audience actually wants to spend time with the brand. That matters when your emails are competing inside a promotions tab packed with dozens of other brands.

Jordan also catches one mistake in Dôen’s otherwise excellent program: two different abandonment emails landing within four minutes of each other. He explains why overlapping cart, checkout, site abandonment, and third-party identification flows can cause this, plus the waterfall exclusions he uses to prevent it.

What you’ll learn:

• Why Dôen has become Jordan’s new favourite email program
• How behind-the-scenes content helps pull customers deeper into a brand’s world
• Why intentional creative can make subscribers actively look for your emails
• How to use photo grids, GIFs, location shoots, and community content
• The abandonment-flow mistake Jordan found in his own inbox
• How to structure exclusions across checkout, cart, site abandonment, and third-party triggers
• Why winning an individual CRO test can still degrade the overall brand experience
• How email design, copy, CTAs, and creative work together as one system

00:00 – Why email + CRO are the fastest path to more ecommerce revenue

01:25 – Jordan’s new favourite email program: Dôen

04:15 – Why Dôen designs for an intentional reader

08:01 – The behind-the-scenes email that immediately got Jordan to open

09:00 – How to stand out in a completely stuffed Promotions tab

12:52 – Jordan finds a mistake

15:49 – The abandonment flow waterfall that prevents duplicate emails

17:17 – Why a “winning” CRO test can slowly degrade your brand

Work with Pilothouse: ⁠https://www.pilothouse.co/get-in-touch?utm_source=dtc&utm_medium=podcast&utm_content=e&rPodcast⁠

Subscribe on YouTube: ⁠https://www.youtube.com/@DTCPodcast

Subscribe to DTC: ⁠https://www.directtoconsumer.co/⁠

Listen to DTC Podcast: ⁠https://podcasters.spotify.com/pod/show/dtcpodcast

After auditing hundreds of email programs, Jordan Gordon has seen the same mistakes show up again and again.

In this episode of The World’s Best Email & Retention Podcast, Jordan runs through 11 common problems that make retention programs harder to manage and less effective, from creating endless Klaviyo segments and bloated flows to mixing too many goals into one post-purchase journey.

He also gets into why non-opener resends can hurt your sending reputation, where your best offer should appear in an email, what brands miss when testing dark mode, and why producing more campaigns can leave you with thinner creative.

Then he moves beyond the inbox with two CRO mistakes he sees constantly: underdeveloped top product pages and homepages that have accumulated too many competing ideas.

What you’ll learn:

• Why you probably have too many Klaviyo segments
• How bloated flows create dead weight in your retention program
• Why each automation should have one clear conversion goal
• Who you should ask for reviews and UGC
• Why non-opener double taps can hurt deliverability
• Where your strongest offer should appear
• Why every brand should be checking emails in dark mode
• How too much campaign volume can weaken your creative
• What your highest-traffic PDP needs above the fold
• How to clean up an overloaded homepage

00:00 – How Email + CRO Drive More Revenue

01:22 – The Email Mistakes Jordan Sees Every Day

03:19 – Why Too Many Flows Become Dead Weight

06:16 – UGC, Reviews & Post-Purchase Mistakes

10:07 – Give Every Automation One Clear Goal

13:29 – Offers, Non-Opener Resends & Dark Mode

16:22 – When Too Much Email Content Hurts Performance

22:13 – PDP & Homepage CRO Mistakes

Work with Pilothouse: ⁠https://www.pilothouse.co/get-in-touch?utm_source=dtc&utm_medium=podcast&utm_content=e&rPodcast⁠

Subscribe on YouTube: ⁠https://www.youtube.com/@DTCPodcast

Subscribe to DTC: ⁠https://www.directtoconsumer.co/⁠

Listen to DTC Podcast: ⁠https://podcasters.spotify.com/pod/show/dtcpodcast

In this episode of The World’s Best Email and Retention Podcast, Jordan Gordon sits down with Alia founder Shaan Arora to break down what makes a high-converting pop-up work.

Shaan shares how Alia grew from a college project to $8 million in revenue before being acquired by Dotdigital for $60 million. He also explains how the company uses behavioral data to personalize pop-ups based on the shopper, timing, creative, and offer.

They get into the role of data as a competitive advantage, how AI is changing software development, and why strong e-commerce brands continue testing even after they find a winning variation.

What you’ll learn:

• How Alia grew from two early customers to a $60 million acquisition
• The four elements behind a “perfect pop-up”
• How timing, traffic source, and customer history affect conversion
• Why blanket discounts can quietly reduce margin
• How customer data creates an advantage that competitors cannot quickly copy
• Why Alia continues focusing on pop-ups as a core product
• How continuous A/B testing compounds conversion gains
• Why flexible software contracts can make experimentation easier

00:41 What makes a “perfect pop-up”

01:48 Alia’s $60 million acquisition

03:13 From college project to $8 million in revenue

08:54 AI, software development, and defensible SaaS moats

12:38 Personalizing the customer, timing, creative, and offer

18:48 Why strong brands never stop testing

Work with Pilothouse: ⁠https://www.pilothouse.co/get-in-touch?utm_source=dtc&utm_medium=podcast&utm_content=e&rPodcast⁠

Subscribe on YouTube: ⁠https://www.youtube.com/@DTCPodcast

Subscribe to DTC: ⁠https://www.directtoconsumer.co/⁠

Listen to DTC Podcast: ⁠https://podcasters.spotify.com/pod/show/dtcpodcast

In this episode of The World’s Best Email and Retention Podcast, Jordan Gordon sits down with Black Crow co-founder Shazad Khan to explore how AI could reshape the ecommerce website.

As ad creative, search queries, and retention messages become more personalized, most shoppers still land on the same static product or collection page. Black Crow Storefronts is built to carry the context of each ad through the full post-click experience, creating tailored landing pages, product flows, carts, and upsells for each audience and campaign.

Jordan and Shazad break down how AI storefronts work, where they fit into a brand’s marketing stack, and how creative teams, media buyers, and agencies may use them to improve conversion after the click.

What you’ll learn:

• How AI is changing the role of the ecommerce website
• Why every ad could eventually lead to a unique storefront
• How Black Crow builds dynamic experiences from landing page to checkout
• Why post-click relevance can improve conversion and ROAS
• Which brands are ready to use AI storefronts
• How Black Crow supports email list growth and abandonment recovery
• How AI could change the responsibilities of media buyers and creative teams

00:00 How to drive more revenue without increasing ad spend

02:50 What will an ecommerce website look like in 10 years?

04:47 The personalization gap after someone clicks an ad

10:06 Inside Black Crow Storefronts

12:30 How AI builds a unique storefront for every ad

17:48 Controlling which products and audiences AI prioritizes

23:08 How AI changes creative and media buying roles

30:24 Black Crow’s AI tools for email and retention

Work with Pilothouse: ⁠https://www.pilothouse.co/get-in-touch?utm_source=dtc&utm_medium=podcast&utm_content=e&rPodcast⁠

Subscribe on YouTube: ⁠https://www.youtube.com/@DTCPodcast

Subscribe to DTC: ⁠https://www.directtoconsumer.co/⁠

Listen to DTC Podcast: ⁠https://podcasters.spotify.com/pod/show/dtcpodcast

This week, we're revisiting a listener favourite from early in the TWBERP catalog. If you haven't been around since the beginning, we can assure you this is a good one. On with the show!

In this episode, we dive into the art of creating email experiences that both sell and inspire.

Join host Jordan Gordon as he explores how heritage brand Filson turns each email into a visual journey, using lifestyle photography, strategic design, and storytelling to craft an aspirational experience for their subscribers.

We cover how Filson strikes the perfect balance between content-driven and conversion-focused emails, how they maximize engagement through VIP sign-ups and theme features, and why their approach to seasonal drops keeps customers coming back.

Whether you’re an email marketer, brand owner, or design enthusiast, discover actionable tips to elevate your email strategy and create a more loyal audience.

00:00 — Intro

01:00 — The Role of Non-Conversion Emails

02:30 — Filson as a Case Study: Building a Visual Experience

05:00 — Making the Most of Your Best Shots

08:00 — Crafting Seasonal Drops

10:30 — Lifestyle vs. Product Focus: Striking a Balance

13:00 — VIP Sign-Ups: Building Long-Term Engagement

15:30 — Design Choices That Work Across Devices

18:00 — The Power of Theme Features

21:00 — Filson’s Take on Journal-Style Emails

24:00 — Closing Thoughts

Work with Pilothouse: ⁠https://www.pilothouse.co/get-in-touch?utm_source=dtc&utm_medium=podcast&utm_content=e&rPodcast⁠

Subscribe on YouTube: ⁠https://www.youtube.com/@DTCPodcast

Subscribe to DTC: ⁠https://www.directtoconsumer.co/⁠

Listen to DTC Podcast: ⁠https://podcasters.spotify.com/pod/show/dtcpodcast

Before anyone talks about LTV, retention curves, or lifecycle marketing, there's one window that matters most: the first 30 days.

Thomas Lalas, founder of Art of Ecomm and author of Retention Economics, joins Jordan Gordon to break down why the first month after a customer's purchase has an outsized impact on lifetime value, profitability, and long-term growth.

They cover why retention is much bigger than email, how top subscription brands reduce early churn, and the systems they use to turn first-time buyers into loyal customers.

In this episode:

00:00 Why email and CRO are the fastest path to profitable growth

01:21 Meet Thomas Lalas and the idea behind Retention Economics

04:40 Why retention is bigger than email marketing

07:00 The first 30 days that determine customer lifetime value

11:44 The three stages of a high-performing retention system

12:14 Pre-delivery: reducing anxiety and increasing perceived value

28:32 Post-delivery: building habits and educating customers

44:13 Rebilling: reducing churn before the next charge

49:27 Why engagement compounds over time

50:26 Agency vs. consultancy: two approaches to retention

51:24 Where to find Thomas and his book

Work with Pilothouse: ⁠https://www.pilothouse.co/get-in-touch?utm_source=dtc&utm_medium=podcast&utm_content=e&rPodcast⁠

Subscribe on YouTube: ⁠https://www.youtube.com/@DTCPodcast

Subscribe to DTC: ⁠https://www.directtoconsumer.co/⁠

Listen to DTC Podcast: ⁠https://podcasters.spotify.com/pod/show/dtcpodcast

All the conversion action on your Shopify store happens in a narrow window. Jordan builds out the diagnostic framework to find it, measure it, and fix it.

What's covered:

• Why sessions, scroll depth, and page depth are all brutally short, and why that concentrates the opportunity
• The 10 power pages to audit: homepage, top 3 category pages by conversions, top 3 PDPs by conversions, top 3 content pages by sessions
• The four metrics to track per page: sessions, add to cart rate, conversion rate, conversions
• Entry vs. internal referrer as two distinct analytical lenses
• Channel segmentation: paid, organic, Klaviyo, direct/other, and why mixing them hides the real signal
• What healthy funnel shape looks like: PDP add to cart rate higher than category, higher than home
• Klaviyo benchmarks: 10% of total revenue attributed, 2-3x conversion rate on email entries
• Sitewide benchmarks: 7.5% add to cart, 2% conversion rate
• Post-click activities to deploy against specific gaps: pre-sell pages, quizzes, site funnels, category flows, bundle builders, recommendations, subscribe and save

Referenced episodes: 69, 70, 73 (retention and email metrics), low-60s series (120-second session framework), recent recommendations flow and essentials flow episodes.

Timestamps

00:00 – Why all the action is in the first 2 minutes, 2 folds, 2 pages

03:17 – How to diagnose a Shopify revenue problem

07:37 – The four metrics that matter: sessions, add to cart, conversion rate, conversions

08:34 – Entry vs. internal referrer explained

10:02 – Channel segmentation: paid, organic, Klaviyo, direct

12:28 – The 10 power pages framework

17:22 – What it means when homepage outperforms your top PDP

21:53 – Post-click activities to deploy against site gaps

26:16 – Klaviyo entry benchmarks and what to expect

31:06 – How to link your CRO ideas to needle-moving pages

Work with Pilothouse: ⁠https://www.pilothouse.co/get-in-touch?utm_source=dtc&utm_medium=podcast&utm_content=e&rPodcast⁠

Subscribe on YouTube: ⁠https://www.youtube.com/@DTCPodcast

Subscribe to DTC: ⁠https://www.directtoconsumer.co/⁠

Listen to DTC Podcast: ⁠https://podcasters.spotify.com/pod/show/dtcpodcast

Email segmentation is getting tighter. Here's what our 2025 research found and what we changed going into H2 2026.

We cover implied consent windows, why we pulled back from 150-day open segments to 120, the real revenue math on long buyer lookbacks, and how to structure a mailable segment that sits inside every other segment you send to.

Key topics:

• Implied consent: 95-day default vs. the legal maximums
• Why 150-day open windows caused inboxing problems on some brands
• Long buyer lookbacks: the $400 on $14,000 reality check
• Engaged vs. unengaged within mailability
• First-time vs. repeat buyer segmentation and why it matters for sustainable revenue
• How to add implied consent directly into existing segments
• This is the internal lifecycle update Pilothouse publishes before every H2. The direction for 2026: tighter than 2025, across the board.

0:00 - What's required to inbox

2:51 - 2025 segmentation research overview

3:50 - Implied consent windows explained

5:16 - Open window: why we stayed at 120 days

7:15 - Where 85% of campaign revenue comes from

9:15 - Long buyer lookbacks: what the data showed

13:49 - How to establish mailability as your foundation

16:45 - First-time vs repeat buyer segmentation

20:27 - Using segmentation to learn about your business

Work with Pilothouse: ⁠https://www.pilothouse.co/get-in-touch?utm_source=dtc&utm_medium=podcast&utm_content=e&rPodcast⁠

Subscribe on YouTube: ⁠https://www.youtube.com/@DTCPodcast

Subscribe to DTC: ⁠https://www.directtoconsumer.co/⁠

Listen to DTC Podcast: ⁠https://podcasters.spotify.com/pod/show/dtcpodcast