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Jess Chan Profile
Jess Chan

@jjesschan

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Diary Of An Entrepreneur | Built @longplaybrands & now @heybackbone. $300M+ generated for DTC. Tweets on building a Retention Ecosystem & the journey to SaaS

Toronto
Joined January 2023
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@jjesschan
Jess Chan
2 years
Been thinking about starting a "Diary of An Entrepreneur" series for a while & figured the best way is to just pull the trigger. In the spirit of Building In Public, I want to start a conversation around the actual day-to-day emotional & psychological journey of being an.
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@jjesschan
Jess Chan
2 days
@Postpilot @Postscript @skio Q4 growth starts with smarter infrastructure in Q3. đŸ“„ Download all 3 playbooks (free) and start building now:
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@jjesschan
Jess Chan
2 days
@Postpilot @Postscript 🔁 Subscription Secrets w/ @skio Before scaling subscribers in Q4, make sure they stay. → Reinforce value in the first 7 days with onboarding flows → Surface and address cancel intent dynamically with save logic → Build a “subscription-first” post-purchase experience.
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@jjesschan
Jess Chan
2 days
@Postpilot đŸ“± SMS: Sales At Scale w/ @postscript SMS isn’t just for promos—it’s your fastest path to purchase. → Set up conversational keyword flows (not just one-way blasts) → Time SMS sends with email campaigns—not after → Use tap-to-buy CTAs to reduce friction and drive mobile.
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@jjesschan
Jess Chan
2 days
📬 Mastering The Mailer w/ @postpilot Optimize the core of your retention engine: email campaigns. → Audit for CTA fatigue—if every button says “Shop Now,” it’s time to rethink → Add logic for non-clickers to re-engage stalled segments → Close the gap between signup and first.
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@jjesschan
Jess Chan
2 days
Most brands wait until Q4 to fix retention. The smart ones start in Q3. List growth, email, SMS, and subscriptions aren’t Q4 problems—they’re Q3 priorities. Here are 3 high-impact tactics from each of our top playbooks to help you prep now (not later): 👇.
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@jjesschan
Jess Chan
6 days
A lot of the traditional DTC marketing tactics are still running a "channel-centric" playbook -- where you're optimizing each channel on its own (TOF vs BOF, ads vs email vs website). It's also how most ecom brands set up their teams/vendors -- an ads team, a CRO team, an email.
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@jjesschan
Jess Chan
10 days
You can't shortcut self-actualization with success. Success falsely promises joy, bliss, peace, contentment, abundance & wealth. But all of those things are found in self-actualization. Yet often, all the rulebooks for success tell us to abandon ourselves in pursuit of.
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@jjesschan
Jess Chan
11 days
Huge kudos to @bandholz for sharing this openly. At @longplaybrands , we're lucky to get to have gotten to see behind-the-scenes of hundreds of businesses over the last 7 years. as a lifecycle marketing firm, advisors & board members. A lot of businesses are struggling or.
@bandholz
Eric Bandholz
12 days
Everyone always shares their wins, but few share their losses. We had losses approaching $1 million over the past two years. (not drop in revenue, but profit losses). It was a financial struggle & I share how we've been able to survive without using outside funding or debt.
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@jjesschan
Jess Chan
13 days
Sustainable subscription growth doesn’t come from a single offer or promotion—it’s built on having the right infrastructure at every stage of the subscriber journey. In our Subscription Secrets playbook, we outline three foundational lifecycle flows that drive long-term.
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@jjesschan
Jess Chan
14 days
Most brands treat pop-ups as a single-purpose tool: collect emails. But that’s a missed opportunity. A high-performing pop-up doesn’t just build your list—it builds intelligence. It tells you why someone converted, what they care about, and how to personalize the experience from.
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@jjesschan
Jess Chan
14 days
Well, it's already Q3! And this is the last 3 months to lay down your lifecycle foundations before Q4 starts:.1. Revamping your email/SMS flows .2. Optimizing your subscription & loyalty programs.3. Testing your positioning, pricing & bundles.4. Gathering customer insights. The.
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@jjesschan
Jess Chan
15 days
NEW PLAYBOOK DROP 📣: MAKING POP-UPS PROFITABLE. Pop-ups aren’t just a UI element—they’re one of the most underutilized growth levers in e-commerce. And chances are, your current pop-up might be costing you more than you think. What if, instead of chasing more traffic, you
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@jjesschan
Jess Chan
16 days
The more time I spend building businesses, the more I realize how easy it is to overlook the quiet systems that hold the business together. Lifecycle marketing is the backbone of all of your marketing strategies. Because it's ultimately about understanding your customer &.
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@jjesschan
Jess Chan
18 days
We’ve audited hundreds of DTC brands—and one of the most common issues we see?. The tools are all there. Email and SMS are live. Campaigns are running. Flows are turned on. There’s a loyalty program, maybe even subscriptions or referrals. But none of it is actually moving the.
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@jjesschan
Jess Chan
19 days
One thing I’ve noticed in my 10 years of e-comm. Lifecycle marketing often doesn't get enough attention or internal investment. Why? Because even when it's done poorly, it SILENTLY drains your company's profit. This is what bad lifecycle marketing is costing you:.‱ Low ROI.
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@jjesschan
Jess Chan
20 days
Most brands still treat lifecycle marketing like they're optimizing a channel: email & SMS. But lifecycle marketing isn’t a channel. It’s the operating system to continually nurture, convert & retain customers -- profitably. It’s how you: . - Turn traffic into customers.-.
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@jjesschan
Jess Chan
20 days
3. Intent-Based Re-Engagement.Rebuild engagement by triggering emails/SMS based on signals like browse behavior, quiz answers, or pop-up responses—not just time lapsed. → Ask: “What are you shopping for today?”.→ Match that intent to product education or offers. Result: Better.
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@jjesschan
Jess Chan
20 days
2. Lifecycle-Based Offer Strategy.Promotions shouldn’t be one-size-fits-all. Use lifecycle segments (first-time buyers, loyalists, lapsed) to shape your offer logic. → First-timers: remove friction.→ Loyalists: reward early.→ Lapsed: incentivize reactivation. Result: Higher.
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@jjesschan
Jess Chan
20 days
1. Welcome Flow > Product Tour.Most welcome flows are a pitch. Instead, think of them as an onboarding experience. → Highlight what makes the product different.→ Address objections up front.→ Guide customers to their first “aha” moment. Result: Higher activation, fewer.
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