Jimmy Kim

eCom Email Marketer

Newsletter: Your dose of retention strategy, actionable insights, & exclusive industry news with Chase Dimond.

We help b2b saas technology companies leverage the community playbook to create the word of mouth to drive leads and awareness through social media, podcasts, newsletters, and events.

CEO & Co-Founder

MediaSpace 🔊

Fueling B2B Growth Through Alternative Media for eCommerce SaaS and Agency. A specialized marketplace connecting eCommerce SaaS companies with high-impact creators, newsletters, podcasts, and industry events

CEO & Partner

Commerce Roundtable

Started as an internal event at Sendlane, built for the community. I acquired the event in Oct 2024.

Our vision is to become the foremost event for eCommerce and digital marketing professionals by delivering valuable insights, actionable strategies, and building long-term relationships among participants while delivering the best customer experience.

A community-focused event - with the community, for the community.

CEO & Founder

eCom Email Certified

A community and certification program for retention marketers (email & sms marketing) for eCommerce.

Join 325+ Retention Marketers at https://www.ecomemailcertified.com/join-community

Community Co-Founder & Certification Instructor

Send It! Podcast

The SendIt Podcast, hosted by email marketing experts and veterans Jimmy Kim and Chase Dimond, is your go-to for leveling up your retention game. Jimmy, Founder and mastermind behind Sendlane, brings over 15 years of hands-on experience in building successful SaaS companies, along with valuable experience growing a DTC brand. Chase, Partner at Structured, has driven over $200 million in email-attributable revenue and is named the #1 influencer to follow in eCommerce.

Together, this power duo breaks down the art and science of retention marketing into bite-sized, actionable tactics that you can put to work immediately. Whether you’re trying to drive customer loyalty, fine-tune your email and SMS campaigns, or master customer segmentation, the SendIt Podcast is your reliable resource for all things retention. 

Each episode is packed with the latest tools, strategies, and real-world insights to help you crush your marketing goals, increase lifetime value, and grow your brand sustainably. In today’s competitive landscape, this is the cheat code you’ve been waiting for!

Co Host

ASOM

ASOM Pod is the only video first e-commerce podcast that offers four different unique perspectives: A(gency) S(aaS) O(perator) M(arketer). Our goal is to provide a holistic view of the e-commerce industry by sharing four perspectives. 

Find us on YouTube or your favorite streaming service, just search "ASOM"

A Commerce Roundtable Production.

Co Host & Moderator

MentorPass

Mentorships on Startup, Email Marketing, Retention marketing, Growth, Business, Life...

Mentor

Sendlane

Chief Innovation Officer

Started as an internal tool in 2013…became a business in Aug 2017. Unified email, sms, and  Reviews for eCommerce. Series A, B, B1, C & C1

Founder & CEO

Vonage

Americas Customer Advisory Board

Knyew

Men's Streetwear Brand. Investor turned Managing Partner. Sold & Exited Partnership in Aug 2017.

COO & Partner

Founder @ Sendlane, Co-Host of ASOM Pod

Do shit you love.

Email Marketer, Content Creator, Retention lover, Builder of startups, business and events. 

I also do podcasts and newsletters.

Fueling B2B eCom SaaS growth with alternative media

Started as an internal tool in 2013…became a business in Aug 2017.

Unified email & sms (soon Reviews!) for eCommerce

Remote Company. Backed by Five Elms Capital (Series A & B) and Zing Capital (seed) 

Feel relatable?

Gonna be a lot of balding guys in San Diego Sept 22-23...

We're just a week away from the best DTC/eCommerce Event you'll attend. 

Commerce Roundtable - A room full of smart people who are ready to get one final hoorah in before they put their heads down for this upcoming holiday season. 

Use code: LASTCHANCE for 50 off

Loaded with $120,000 in giveaways..

We promise: 
Amazing experience (an event unlike any other) 
Amazing views (on the water)  
Amazing content 
Amazing food (best in class, hands down) 
Amazing people! (the community!)  

1 Week away!

I hope you have an ASOM weekend ✌️

Marketer of 17+ Years, 4x Founder. Former DTC/Retailer & SaaS Founder. Newsletter. Host of ASOM & Send it! Podcast. Event Host.

You spent $45 on ads to acquire Sally. 
She finally buys. 
You pack her order. 

What do you put in the box?
A. Just the product she paid for.
B. The product, plus a 10% off coupon for her NEXT order.
C. The product, plus a single serve sample of your BEST SELLING product.

If you picked B, you're following the standard playbook. And it's leaking money.

The coupon tells her, "Wait to buy again until it's on sale". You're training her to be discount-dependent.

The sample of your best seller? That's a different game. It's a free gift with a hidden mission: to introduce her to the product she's most likely to fall in love with and buy full price.

The "Second Box" is where eCom brands lose 80% of their potential profit.

Here’s the actionable part: Your post purchase pack should be a cross sell vehicle.

- Sample of Product A with purchase of Product B.
- A single serve snack with a purchase of a subscription box.
- A scent strip of your new perfume with a purchase of the lotion.

You've already paid the customer acquisition cost and the shipping. The marginal cost of adding a sample is tiny. But the potential LTV increase is massive.

You're not just delivering an order. You're conducting the first onboarding session for her next one.

Email Marketer of 17+ Years, 4x Founder. Former DTC/Retailer & SaaS Founder. Newsletter. Host of ASOM & Send it! Podcast. Event Host.

What an incredible 2 days 🙏

Thank you to everyone from the bottom of my heart for the love and the support from the community to helping deliver another successful Commerce Roundtable San Diego! 

Big big shoutout and thank you to...

Nick Shackelford for being the best MC and partner 
Madison Marsh our event director who crushed every detail of the show.
Greg Wilson the design GOAT for every pixel perfect design and video.
To Caitlin Hutchinson and Cherie Ueno for the helping hand in delivering the event. 
To EightOne events, Miami Video Productions, and RHODES Audiovisual.
To all the speakers.
To all the amazing sponsors.
To the partners. 
To the attendees. 
To the community.
To the San Diego weather.

Thank you. Thank you. Thank you.

2026 we're running it back. 

Austin, April 23-24, 2026. 
San Diego, Sept 14-15, 2026. 

Hope to see you there ✌️

And we’re off to San Diego ✈️

Months and months of planning and the big day is finally here!

Almost 600 people are traveling from all over the world to join us for 2 action packed days for Commerce Roundtable.

And I couldn’t feel more grateful 🙏

A big shout out to all the speakers, the sponsors, and attendees for allowing me to build the community event of the year. 

And a very extra special thank you to the hard planning and designing by our internal team: Madison, Greg, Caitlin, Cherie, and Nick Shackelford. 

Loaded with $220,000 in giveaways..

We promise: 
Amazing experience (an event unlike any other) Amazing views (on the water)  
Amazing content 
Amazing food (best in class, hands down) 
Amazing people! (the community!)  

We're just 2 short days away from showtime.  

And we're down to our final tickets!

Use promo code: FINALCHANCE for 50 off a ticket today. 

I hope you have an ASOM weekend ✌️

No alternative text description for this image

Your website is a front door. 

It's formal and expects a purpose.

But community is built on the welcome mat: the space just outside where people linger.

The comments section on your Twitter post is your welcome mat.

The replies to your email newsletter are your welcome mat.

The "questions and answers" section on your product page is your welcome mat.

Most brands ignore these spaces. They're missing the whole party.

How to tend to your welcome mat:

- End your emails with a genuine question: Not "Buy now," but "What's the one kitchen gadget you can't live without? Hit reply and let me know." Then, reply to every single response personally.

- Feature the best comments: Every week, screenshot the best comment or reply you got and feature it in your stories or next email. "This made our week. Thanks, @username!"

- Let customers answer each other: If someone asks a question on your product page, don't just answer it yourself. Email a past customer and ask if they'd like to share their experience.

A front door is transactional. 

A welcome mat is relational.

Build the mat, and they'll walk through the door on their own.

Day 2 of Commerce Roundtable starts now!

We gave away a trip for 2.. to Hawaii

Most brands are terrified of negative feedback. 

One mattress company turned it into their only marketing strategy.

Casper’s early genius wasn’t the mattress. It was a customer service policy so counter intuitive it became a viral engine.

Their “100 Night Risk Free Trial” had a secret clause: if you returned the mattress, they didn’t want it back. They’d refund you and tell you to donate it to charity.

This felt insane. Why throw away a perfectly good mattress?

The math was brilliant:

- The cost of processing a return (shipping, cleaning, restocking) was huge.
- The cost of a donated mattress was just the COGS.
- But the marketing value of that donation was priceless.

A customer, feeling guilty about the “waste”, would often post online: “Casper told me to donate this $1,000 mattress to goodwill. What an amazing company!”

That single act generated more trusted, authentic word of mouth than any ad ever could.

Audit your return policy. Is it designed to save you pennies on logistics, or to generate dollars in trust?

The most expensive return you can process is the one that silently kills future referrals.

Thank you to the community for your amazing love and support.

Commerce Roundtable 2025 San Diego  

See you in Austin. April 23-24 2026 🤠

The classic marketing funnel is a lie.

Customers don't go from "Awareness" to "Loyalty" in a straight line.

They take a messy, spiral path. 

Here's how to build for that.

Think of your customer's journey not as a funnel, but as a spiral staircase.

They might discover you through an ad (awareness), follow you on Instagram (engagement), then leave.

Months later, a friend mentions you (word of mouth), they see a review (consideration), and finally buy.

The touchpoints are scattered and non linear.

Your job is to make every single touchpoint valuable, even if it doesn't lead directly to a sale.

- Is your Instagram just product shots? Or is it genuinely entertaining/educational? (Nina Julian at Oma's Pride does a great job here) 
- Does your customer service just solve problems? Or does it surprise and delight, creating stories people tell their friends?
- Is your packaging just a box? Or is unboxing it a mini experience worth sharing?

Audit every single point where a human interacts with your brand, from a TikTok comment to the post purchase email.

"If this is the only interaction someone has with us for 6 months, does it leave them better off?"

Email Marketer of 17+ Years, 4x Founder. Former DTC/Retailer & SaaS Founder. Newsletter. Host of ASOM & Send it! Podcast. DTC Event: Commerce Roundtable

Your email preference center is probably a list of checkboxes for email frequency.

It should feel more like a personality quiz.

Nobody wakes up wanting to "manage their subscription preferences".

But they might want to tell you what they're interested in.

Rename the link in your footer from "Email Preferences" to "Get Better Emails" or "Tell Us What You Like".

When they click, don't just ask how many emails they want. Ask what kind of content they want.

-  "I want deals and discounts only"
- "I want new product launches"
- "I want educational content (how-tos, tips)"
- "I want behind the scenes stories"

Then, tag them accordingly inside your ESP. 

This lets you send a "deals" segment a sale email without annoying the "educational content" segment.

Your unsubscribe rate will drop because you're giving people what they actually asked for

You map your own customer journey. 

But have you mapped the moment your competitor's customer becomes disappointed?

That moment is your greatest acquisition opportunity.

A project management software company did this.

They identified the top three competitors. Their team signed up for free trials and used the products extensively.

But they weren't testing features. They were logging the exact moment a new user would likely feel frustration, confusion, or limitation.

They found a common point: on day 3, users of Competitor X hit a confusing paywall for a basic feature.

They then targeted ads to users who had just signed up for Competitor X, with copy that said:

"Tired of features being locked behind confusing paywalls? [Feature Name] is always free on our platform. Try it without the gatekeeping."

They spoke directly to a live, simmering frustration.

Actionable take: Have your team become customers of your top 3 competitors.

Don't just look at their features. Create a "Friction Log" of every confusing, disappointing, or limiting moment.

Then, build your acquisition messaging around solving those very specific pains.

The real reason you shouldn't end your prices in .99 has nothing to do with psychology and everything to do with word of mouth.

We all know the old trick: $99.99 feels cheaper than $100. But that's a superficial game.

There's a deeper, more powerful reason to use round numbers: they are easier to remember and repeat.

Think about a famous brand like Allbirds. Their shoes cost $115. Not $114.99. One hundred fifteen dollars.

That's a "whisper number", a price that's clean and easy to say when recommending to a friend.

- "Yeah, these amazing shoes were about a hundred bucks"
- vs. "They were, uh, ninety nine ninety nine, I think?"

The .99 price tag signals discount brand. The round number signals value brand.

It says we're confident in what our product is worth. It simplifies the mental math for customers and makes verbal referrals effortless.

If your brand is built on quality, craftsmanship, and value (not just being the cheapest), test round number pricing.

$50. $200. $35.

See if it changes the perception of your product and makes it easier for your customers to become your salespeople.

Pretty soon, your brand won't be defined by your logo or your color scheme.

It will be defined by the personality of a chatbot. 

And most brands are completely unprepared.

Right now, you have a brand voice guide.

It probably has words like "authoritative but friendly", "helpful but not salesy", "professional but approachable".

This is about to get real.

When a customer interacts with an AI selling your products, that AI's personality is your brand. Is it a witty, sarcastic friend? A knowledgeable, patient teacher? A brisk, no nonsense expert?

If you don't decide, the AI's default tone will decide for you. And "default" is the fastest way to be forgettable.

Look at the early internet. 

The first websites all looked the same (grey background, blue links). 

Then brands realized design was a competitive advantage.

We're at the same point with AI personality.

Create your "character Bible".

Define your brand character.

Gather your team and answer these questions as if you were casting an actor to play your brand in a movie:

1. What's their backstory? (e.g., "They used to be a frustrated customer themselves, so they get it.")
2. What's their sense of humor like? (Dry? Goofy? Nonexistent?)
3. What's their pet peeve? (e.g., "Wasting the customer's time with fluff.")
4. How do they deliver bad news? (e.g., "Directly, with a sincere apology and an immediate solution.")
5. What three words would a customer use to describe them after a 2-minute chat?

Once you have this, the technical part is easy. This "character bible" becomes the prompt engineering guide for any AI integration.

The brands that win the next decade won't just have the best products. They'll have the most trusted, relatable, and helpful conversational personas.

The storefront is becoming a relationship.

You're segmenting your list by what people DID. 

But you should also segment by what they FELT.

Let me explain 

Someone who bought a "solution to a painful problem" is a different customer than someone who bought a "fun luxury treat".

Actionable Fix: Tag customers based on the category of their first purchase.

The "Solution" Buyer: (e.g., acne cream, organizing bins) - Tag: "Problem Solver"

The "Aspirational" Buyer: (e.g., luxury candle, fancy workout set) - Tag: "Lifestyle"

Then, craft your future messaging to match that emotional intent.

1. To the "Problem Solver": Lead with efficacy. "Tired of the clutter coming back?" "Struggling with flare ups again?"

2. To the "Lifestyle" Buyer: Lead with aesthetic and feeling. "Elevate your morning routine." "Create a cozy corner."

You sold them a feeling. 

Now keep selling that same feeling.

And if you're wondering.. "how do you tag?" 

Check out Omnisend's behavior tagging feature for an easy way to identify behavior in real time. I've enjoyed their platform as a user and a partner.

A great way to understand your true brand value is look at your product's second hand market.

The resale price is basically the market’s pure, uncensored referendum on your brand's perceived value.

Rolex watches and Yeti coolers often sell for near retail price on eBay and Facebook Marketplace.

This isn't an accident. It's the result of relentless brand building, perceived quality, and controlled supply.

It tells a new customer: "This product holds its value. It's a safe bet"

Conversely, if your product is listed for 80% off its original price the week after it's bought, it screams disposable value.

Your goal shouldn't just be to create demand for a new product, but to create a product that holds, or increases its value on the secondary market. This is the ultimate trust signal.

Search for your product on second hand sites. What’s the average resale price as a percentage of the original?

If it's low, your focus shouldn't be on more marketing, but on building a product and brand so desired that people believe it's worth holding onto.

Every founder I know says the same thing:

“We’ll fix our backend after the next milestone.”

After the launch.
After Q4.
After the raise.

But here’s what that delay actually costs:

- A burned-out ops lead who spends their Sundays reconciling tax data
- Thousands in penalties from states you didn’t realize you owed
- A finance team stuck doing busywork instead of helping drive growth

This isn’t about falling behind - it’s about setting the ceiling for how far you can go.

Kintsugi solves that ceiling problem.

✅ Real-time nexus tracking
✅ Fully automated filings across all 50 states
✅ Integrates with Shopify, Stripe, NetSuite, and more
✅ No contracts, no rip-and-replace migration headaches

You don’t scale chaos. You clean it up first - so scale actually works.

If you’ve been punting tax cleanup to “later,” this is your sign to handle it now.

Save time, save money, and focus your time on making more money instead of wasting your time with tedious tax filings today

Get a free nexus compliance check and 3 months free when you mention this post. (No contracts required): https://lnkd.in/ex3gssCb 

As a proud partner of Kintsugi and Pujun Bhatnagar- I'm excited to partner with them to leverage AI with something so "boring" to easy.

Innovation doesn't mean inventing something new. It means introducing magic to something familiar.

The first iPhone wasn't a completely new concept. It was a phone + an iPod + internet.

Familiar things, made magical by a touch interface. The magic was in the how, not the what.

Look at Ooni pizza ovens. People knew pizza ovens. Ooni made them portable, hyper fast, and fueled by pellets.

They took a familiar backyard activity and made it feel like a magic trick. "You can make restaurant-quality pizza in 60 seconds." The magic is the speed and the spectacle.

Your product is probably familiar. A bag is a bag. A lamp is a lamp.

Where is the magic? Is it in the material? The transformation? The unexpected speed or result? Don't market the specs of the oven. Market the 60 second magic trick.

List your product's category. Now, what is the one "magical" thing it does that others in the category don't?

(e.g., "It folds flat in 2 seconds," "It changes color with your mood," "It arrives fully grown").

Lead with that magic.

Amazon's "Frequently Bought Together" generated $35 billion last year. 

But the algorithm isn't what you think.

Everyone assumes it shows what other people bought.

Wrong.

It shows what will make the current cart profitable.

Here's how it actually works:

Step 1: Calculate margin on current item
Step 2: Find items that increase total basket margin
Step 3: Filter for return rate impact
Step 4: Show combination most likely to never come back

Example: You're buying a $30 phone case (40% margin).

It COULD show:   Screen protector ($8, lots of people buy it)

It ACTUALLY shows: Wireless charger ($45, high margin, never returned)

The really dirty secret?

They'll sometimes show combinations they know work poorly together. Why? Because when you buy incompatible items, you keep both and buy a third item to fix it.

Customer buys laptop + wrong charger = Customer keeps both, buys right charger = 3 sales instead of 2.

But here's the masterclass part:

They track "bundle regret rate" - how often people return one item from a bundle.

If you return just the add-on, they still won. They got the original sale plus free data about what doesn't work.

So what's the lesson? 

For your store:

- Stop showing "works well with". Start showing "solves the next problem".
- Track bundle return patterns. What gets kept vs. returned?
- Price bundles so returning one item feels like losing value
- Create intentional friction: "These items were selected together for a reason"

The best upsell is what makes returning your product feel incomplete.

The heaviest cost in your store is the cognitive tax you charge for every decision.

Let me explain 👇

A study on jam stands is famous: 24 flavors got more traffic, but the 6 flavor stand sold 10x more. 

Choice paralysis is real. But it's deeper than that.

The cognitive tax is the mental energy a customer spends figuring out if your product is right for them. Most sites make the customer pay this tax alone.

I studied a DTC shoe brand that had a 4% conversion rate on a popular boot. They made one change: they replaced the "Add to Cart" button with two buttons side by side.

Button A: "I need everyday comfort for walking"
Button B: "I need durable support for long work shifts"

Clicking either added the boot to the cart. But it triggered a different post purchase email flow about how to care for the boot based on that use.

Conversion jumped to 6.5%. Why? They acted as a guide. They paid the cognitive tax for the customer by making the choice for them.

On your key product page, identify the two primary use cases. Can you replace a single generic CTA with two specific, self identifying ones?

You're not complicating the choice. 

You're simplifying the customer's self diagnosis.

Welcome to Commerce Roundtable San Diego 

Nick Shackelford

Taplio

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