TL;DR:

• Subscribers drive 3x more value than one-time buyers. Subscriptions create ongoing relationships that build loyalty and increase lifetime value.
• Make subscription opt-ins easy and appealing. Use tools like default subscription settings, upsell widgets, and A/B testing to encourage conversions at every step of the journey.
• Retain subscribers by treating key drop-off points as recovery moments. Use win-back campaigns, payment recovery, and personalized support to reduce churn.
• Meet customers where they are with AI-powered tools. Solutions like Gorgias Shopping Assistant and Recharge Concierge SMS provide real-time, contextual support and subscription management.

Vanessa Lopez, VP of Customer Experience at Recharge, recently led a workshop that outlined how brands can transform one-off interactions into rich subscription journeys that increase opt-ins, reduce churn rate, and boost lifetime value (LTV). 

Here’s what we learned.

What are the different subscription types?

There are many different ways that you can offer subscriptions. Here’s a rundown of the most common. 

Subscribe and save

The most common subscription type is “Subscribe and save.” Instead of making a one-time purchase, customers subscribe to a product and receive it on a different cadence, whether that's weekly, bi-weekly, monthly, or quarterly.

For example, Apothékary offers a Subscribe and Save option for its herbal remedies where shoppers get a discounted rate if they subscribe every one, two, or three months. 

Subscription boxes 

Subscription boxes ship to customers monthly. Shoppers subscribe over a course of time, like every quarter, six months, or year. For example, CrunchLabs offers a prepaid Build Box option for kids and adults who want to tinker like engineers. 

Meal kits

Meal kits are weekly food delivery services that either include pre-packaged ingredients to cook a dish or fully cooked dishes.

Surprise and delight

For brands that are selling higher-cost or unique items, subscriptions to purchase the same product over and over might not be the best way to gain subscribers.

The better option is a curated box, also known as a "subscribe and delight" or “mystery” box. It’s a unique way to cater to customers who prefer trying out different products, rather than receiving the same product on a recurring basis.

For example, premium snack box brand Bokksu specializes in shipping Japanese snacks. Rather than packing the same treats each month, the brand curates different items with every package. This creates both excitement and differentiation each time a customer gets a delivery.

How to drive revenue growth with subscriptions

1. Turn interactions into journeys
2. Create multiple touchpoints for conversion
3. Retain subscribers over time
4. Meet customers where they are
5. Approach AI as a solution-driver

Subscriptions are the original relationship between a brand and its customer. In fact, subscribers drive three times more value than the one-time buyer. That's because a one-time purchase is really just that—a moment in time—while subscriptions are a journey.

“When you have a customer and they subscribe, you get to see that moment they fell in love with your brand,” says Vanessa. “You get to see when they have those moments where they made you a part of their routine. Every time they engage with you and purchase something new, you learn their rhythms. You learn their preferences. It's impossible to do that with one-time buyers for the most part.”

Subscribers drive three times more value than the one-time buyer, and that's because a one-time purchase is really just that—a moment in time—while subscriptions are a journey.

1) Turn interactions into journeys 

Subscribers can only drive growth if you can get those customers to subscribe in the first place. This is what Recharge does: it takes customer interactions and turns them into a customer journey, allowing you to act on those signals in a personal way at scale.

It all starts the moment a shopper browses a product. Each touchpoint is an opportunity to turn that shopper into a subscriber—from the product description page to the subscription widget to checkout.

Vanessa’s tip? Make subscriptions the default option on a product description page. When you present customers with the better and more convenient option, and they see this information at the right time, they're more likely to subscribe. 

Put it into practice 💡

Now, it’s time to test. Here's a checklist you can follow to A/B test your subscription journey: 

• Test the small details, like button styles, CTA copy, subscribe and save benefits, and their positions on the page.
• Compare different value propositions and discounts. 
• Analyze the difference in opt-in and subscriber rates and product performance, and keep iterating. 

When customers see the right information at the right time, they're more likely to subscribe. That's because it's the better and the more convenient option.

2) Create multiple touchpoints for conversion

Let's say you have a customer who starts on a product description page. They decide not to subscribe—no worries. You can catch them in the cart. 

When they add a product to their cart, you can upsell them with different subscription benefits so they know what they're missing out on. Do it again when they review their cart, and then again when they go to checkout, showing them complementary products that they might be interested in.

And don’t forget to take advantage of that post-purchase "your order is confirmed" high—offer customers cross-sell products, complementary products to their order, or similar items to what they've purchased in the past.

By creating multiple touchpoints for conversion, you’ll increase the possibility that they’ll make a purchase.

Put it into practice 💡

Set up automations in the subscription tool –– like Recharge –– you use. That means adding on upsell and cross-sell tools, and perfecting the times they trigger for customers. Test out different copy and cross-sell/upsell offers to see what resonates the most. 

3) Retain subscribers over time 

Just as important as acquiring customers is keeping them around. 

The Recharge team names three core customer moments that might actually diverge from what brands expect to happen in the customer journey:

1. When a payment fails
2. When a customer cancels their subscription
3. When a customer skips—and keeps on skipping

And while they might seem like hiccups in the process, these moments are actually hero moments. They’re moments that give you the opportunity to actually win those customers back.

Put it into practice 💡

• Prevent cancellations by addressing individual customer concerns at scale with a help desk like Gorgias. 
• Set up win-back campaigns. Recharge found that these types of campaigns can convert up to 35% of subscribers by giving them a compelling personalized offer and a straightforward reactivation.
• Recover failed payments to ensure small issues –– like billing and shipping address inconsistencies –– don’t get in the way of your sales. 
• Connect all of your customer touchpoints with rewards and referral products.

4) Meet customers where they are

For browsing shoppers, educational and informational resources are the best way to meet their needs, hesitations, and objections.

For regular subscribers, it’s providing them with direct control over their subscription, whenever they want.

The goal is to reach customers where they already are and respond instantly to their needs in a personalized way.

Gorgias’s Shopping Assistant does exactly that—meeting customers where they are by answering customer questions and even initiating conversations based on browsing activity. 

This AI sales tool detects a shopper's intent, cart contents, and browsing behavior to initiate conversations, recommend products, and even send discounts as they make a decision.

Modern bidet brand TUSHY saw a 20% increase in chat conversion rate after implementing the tool.

Put it into practice 💡

Decide how you’d like to leverage AI and automation to meet customers where they are. That might be by providing a phone number that customers can interact with via SMS, or implementing a tool like Shopping Assistant to strike up conversational AI chats. Using AI and automation will help you better meet your customers where they are and at scale. 

5) Approach AI as a solution-driver

Rather than using AI to come up with problems your brand can solve, Vanessa recommends looking at the challenges your brand has already seen with subscriptions.

The key is to view AI as a tool that drives three core areas: 

1. Scaling your business without adding headcount
2. Reducing churn
3. Increasing how much customers spend with you over their lifetime

Vanessa says the most effective strategy starts with leveraging AI-powered tools, such as Recharge’s Concierge SMS.

Typically, SMS tools use template auto responses like, "How do you want to manage your subscription? Type one to cancel, type two to skip." But these aren’t compelling enough for customers to respond. What if they want to do something that doesn't fit in those two options?

Concierge SMS enables brands to build stronger relationships with their customers through conversations powered by pre-trained AI. It personalizes SMS support with customers, so relationships can expand into loyalty.

Put it into practice 💡

Implement an AI-driven subscription management tool that allows customers to interact and ask questions via SMS, rather than only being able to confirm or deny upcoming shipments.

Grow your brand sustainably 

Gorgias and Recharge are a powerful combination when it comes to integrating subscription management with top-notch customer support.  

With Recharge, efficiently convert one-time buyers into subscribers, retain subscribers through intelligent interventions, and connect every customer touchpoint into one cohesive journey. 

With Gorgias, sell more and resolve support inquiries with conversational AI. 

Book a demo →

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TL;DR:

• Segment customers for personalized support. Use purchase history and behavior data to tailor every interaction, making conversations more relevant and higher-converting.
• Offer onboarding calls for complex products. TUSHY's "Poo-Rus" turned free install calls into a $15 paid service that dramatically boosts customer LTV and retention.
• Pick up the phone strategically. Use voice calls for abandoned carts, stuck tickets, and VIP follow-up.
• Give agents freedom to make judgment calls. Empower your team to bend policies and offer solutions that prioritize retention over rigid rules—confident agents drive more cross-sells.
• Train for helpful selling, not pushy pitches. Use roleplaying to teach agents how to spot buying signals and offer value naturally.

At Gorgias Connect LA 2025, CX leaders from Tommy John, TUSHY, Triple Whale, and Talent Pop shared how support teams solve problems and drive revenue.

This shift, known as the support sales flywheel, doesn’t involve massive overhauls or shiny new tools. Instead, it means doing the small things exceptionally well, like picking up the phone, empowering agents to make judgment calls, and adding a personal touch where others automate.

These brands have shown that when support teams focus on consistency, connection, and conversion, the results compound. Every thoughtful interaction spins the flywheel faster, boosting loyalty, LTV, and revenue.

Ahead, we’re breaking down the most actionable takeaways so your team can start building its own support-led growth engine.

Watch the full panel here:

5 tactics that power the support sales flywheel

From scrappy install calls to AI-powered training, these CX leaders aren’t only talking about driving revenue, they’re doing it. Here’s how they’re turning support into a sales flywheel, and the tactics your team can start testing today.

1. Personalization at scale starts with smart data

“Customer service done right is actually a great source of revenue.” That’s how Tamanna Bawa, Tech Partner Manager at Triple Whale, kicked off the conversation on how data can transform CX from reactive to revenue-driving.

She advises segmenting customers based on purchase history and behavior to deliver more personalized, higher-converting interactions. 

In a market where margins are razor-thin and ad costs are high, Tamanna emphasized that “incremental gains from personalization are the difference between companies that are thriving and the ones that are just surviving.”

Steal this strategy 

• Segment customers based on behavior and purchase history using your helpdesk, CRM, or analytics tool.
• Give agents access to this data so they can personalize every interaction.
• Use macros that adapt based on customer segments, like VIP status, product interest, or past issues.
• Focus on relevance over volume: one well-timed, tailored message converts better than a generic one.

2. The power of onboarding calls

What do you do when your hero product needs a cultural shift as much as it needs installation instructions? If you’re TUSHY, you send in your “Poop Gurus.”

Ren Fuller-Wasserman, Senior Director of CX at TUSHY, shared how her team launched a scrappy, free CX-led service that has now become a legendary video install program to help customers set up their bidets.

The real value wasn’t just tech support. As Ren put it, “It wasn’t about the actual install process, it was the encouragement they needed to change culture.” These calls sparked deeply personal moments (yes, even with cats and toddlers wandering in) and created the kind of emotional connection customers never forget.

Today, that service has evolved into a $15 paid add-on at checkout, and the customers who use it have significantly boost LTV and retention. It’s a masterclass in turning support moments into revenue through genuine human connection.

Steal this strategy

• Identify a product or feature your customers often hesitate to use, install, or fully understand.
• Offer free, low-lift onboarding calls via Zoom or Google Meet to guide them through setup or usage.
• Track LTV, CSAT, or repeat purchase rates for those who opt in.
• If it drives results, package it as a paid add-on at checkout or use it to surprise and delight key segments.
• Use simple tools like Calendly and Typeform to automate scheduling and reduce lift on your team.

3. When in doubt, pick up the phone

Phone support is back, and it’s becoming one of the most effective ways to turn conversations into conversions.

Ren from TUSHY swears by it. Her team uses customer phone numbers from abandoned carts to reach out directly. “You can send a hundred emails,” she said, “but a voicemail from a real person cuts through the noise.” Even if customers don’t answer, the fact that a brand called is memorable, and often enough to drive them back to checkout.

Max Wallace, the Director of CX Tommy John echoed the value of voice. His team recently implemented Gorgias Voice, using it to track conversion rates by agent. That visibility helps them identify what top performers are doing differently and replicate it across the team. “By the end of a tough call, customers often apologize for how they started. You can’t get that kind of de-escalation over email.”

In a world where inboxes are crowded and chat fatigue is real, a real voice builds real trust and real revenue.

Steal this strategy

• Start small: offer limited phone hours once your chat and email support are dialed in.
• Use phone strategically—for abandoned cart outreach, stuck tickets, or VIP follow-ups.
• Track call outcomes with tools like Gorgias Voice to see which agents are converting.
• Train agents to de-escalate and personalize through roleplaying or AI-based call simulations. 

Pro Tip: Don’t rush into phone if your other channels aren’t dialed in. “Master email and chat first. Then, start with limited phone hours. Taste it before scaling it,” said Armani Taheri, the co-founder of TalentPop. 

4. Trust your team to use their judgment

For Max at Tommy John, revenue-driving support starts with two things: deep product knowledge and the freedom to bend the rules.

“We have five different fabrics for men’s underwear alone,” Max shared. To help customers choose the right one, agents need firsthand experience. That’s why Tommy John sends new products directly to the support team, so they can offer real, personalized recommendations like “Try Second Skin instead of Cool Cotton.”

But product knowledge is only half the equation. The other half is empowering agents to make judgment calls. Tommy John’s “Best Pair Guarantee” allows customers to try a product and get a refund or replacement if it’s not the right fit. 

Agents are trained to prioritize retention, offering replacements instead of refunds, recommending better-suited products, and using their own discretion to keep customers happy.

As Max put it, “We don’t have really strict policies… we want them to use their best judgment.” That confidence translates into smoother resolutions, more cross-sells, and customers who stick around.

Steal this strategy

• Send new or popular products to your CX team so they can speak from firsthand experience.
• Build simple product cheat sheets or comparison guides to help agents make tailored recommendations.
• Give agents clear guidelines—but also the freedom to make judgment calls when it comes to refunds, replacements, or policy exceptions.
• Let your team know it’s okay to “bend the rules” if it means keeping a customer happy.
• Track outcomes like retention and CSAT to show how empowered agents directly impact loyalty and LTV.

5. Training teams to sell without the push

How do you train outsourced agents to drive revenue, without sounding like a sales team? According to Armani Taheri of TalentPop, it starts with confidence and context.

“You have to tailor-fit the training approach to each brand,” he explained. That means grounding agents in product knowledge, tone of voice, and customer journey before they ever interact with a shopper.

One of the most effective tactics is roleplaying. Armani’s team uses both live roleplays and AI-powered chat simulations to prepare agents for real conversations, pre-sales, post-sales, and everything in between. Tools like Replit and Lovable help create lightweight, brand-specific training environments agents can practice in at their own pace.

The goal isn’t to turn CX reps into hard sellers. It’s to give them the confidence and consistency to recognize revenue opportunities, and act on them in a natural, helpful way.

Steal this strategy

• Start with the basics: make sure agents understand your product, tone of voice, and customer journey.
• Roleplay low-pressure scenarios, then layer in more complex ones.
• Try AI-powered training tools like Replit or Lovable to create brand-specific simulations agents can practice anytime.
• Emphasize helpfulness over selling: coach agents to spot buying signals and offer value, not push products.
• Review transcripts together to highlight great conversations and show how small shifts lead to better outcomes.

Tools to power your flywheel

Ready to turn your CX team into a revenue engine? Here are some of the tools mentioned by the panelists that help make it happen:

• Gorgias Voice: Track revenue by agent, spot top performers, and improve conversion rates across the team.
• Flip CX: Automate common phone interactions with AI-powered voice support.
• Kixie: Drop voicemails, integrate with Klaviyo and Shopify, and build smart call queues for abandoned cart outreach.
• Calendly + Typeform: Scrappy, low-lift tools for scheduling paid or free support calls that drive LTV.

Whether you're scaling phone support or experimenting with post-purchase outreach, the right tools make the flywheel spin faster.

Your CX team might be your best-kept sales secret

They’re on the front lines with your most engaged customers, answering questions, easing doubts, and uncovering what really drives purchases. With the right tools and training, they resolve tickets and help close the sale.

With tools like Gorgias Voice, it’s easier than ever to connect the dots between conversations and conversions.

Want to see how your CX team can help drive growth?

Book a demo to see how Gorgias Voice powers sales through support.

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TL;DR:

• Start with your CX team—they know what customers are asking. Their insights reveal what’s confusing, what’s converting, and what’s causing returns before marketing ever gets involved.
• Turn pre-sale questions into better messaging. Use common support queries to improve landing pages, product descriptions, and emails so customers feel confident enough to convert.
• Your best-performing products aren’t always the most hyped. Let real customer comments guide your messaging by identifying what people rave about in chats and reviews.
• Customer confusion and returns usually stem from messaging gaps. Fix product pages, policies, and descriptions to better reflect what people need to know upfront.

Your CX team talks to customers every day. They know what’s confusing, driving purchases, and causing returns, because they hear it firsthand.

But all too often, those insights stay siloed in support tickets and live chat transcripts instead of informing the campaigns that shape the customer journey.

This post is here to change that. We’re breaking down the most valuable questions marketing teams should be asking their CX counterparts. When marketing and CX work together, you get more relevant messaging, smarter product positioning, and campaigns that convert.

Whether you’re planning a big seasonal push or just want to improve product education, this is where to start.

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1. What do customers ask about before buying?

Your CX team knows what makes shoppers hesitate. They’re the ones fielding questions like: Does this come in a larger size? Is it final sale? Will it arrive in time?

Beyond being pre-sale inquiries, they’re signals. They reveal what your customers care about most, and where your messaging may be falling short. When marketing teams tune into this, they can proactively address objections in landing pages, product detail pages (PDPs), emails, and top-of-funnel content.

At luxury jewelry store Jaxxon, Director of Customer Experience Caela Castillo saw firsthand how important it is to address these questions early. 

“Chat used to be a support tool for repetitive questions and problem-solving, but now AI Agent takes care of that for us,” she said. Once those friction points were handled upfront, the CX team could focus on more meaningful conversations, and conversions improved.

And when AI recommended the wrong products? Conversions dropped. It was a clear signal that relevance matters, especially before the sale.

Ask your CX team:

“What do customers most often need to know before they buy, and how can we answer that earlier in the journey?”

2. What product do customers rave about—and why?

Your best-selling product isn’t always your hero product. Sometimes, it’s that under-the-radar item that customers can’t stop talking about. The one that shows up again and again in reviews, chats, and post-purchase surveys.

The insight is gold for marketers. The key is to find out why people love it. Is it the fit? The feel? The results?

At online fashion brand, Princess Polly, Alexandria shared that her team expected Gen Z shoppers to lean on AI for recs, but what really influenced them was customer feedback. Reviews, not bots, built trust. That’s why campaigns built around real customer language and experiences often outperform the most polished product copy.

Shopping Assistant can turn those rave reviews into real-time action. It highlights top products using your Shopify product catalog to make personalized recommendations, proactively assists shoppers by using behavior signals, and even offers tailored discounts when they’re ready to convert. That means less guesswork, greater relevance, and an easier path to purchase.

Ask your CX team:

“Which product do customers rave about most, and what exactly are they saying?”

3. What product causes the most complaints?

When customers are frustrated, it’s easy to blame the product. But in many cases, the issue isn’t quality, it’s communication.

At Shinesty, a men’s underwear brand, Molly Kerrigan, Senior Director of Retention, observed that high return rates often stemmed from unmet customer expectations. 

She noted the importance of maintaining clear and consistent communication as the company grows, “We get a lot of praise from our customers, and they talk highly of our CX team after 1:1 interactions. We can’t lose that as we scale.” 

Molly notes that using Gorgias AI Agent enables Shinesty’s customers to receive quick answers, freeing her team's time for more complex or sensitive issues.  

Similarly, Princess Polly saw that delivering a standout customer experience meant being fast, consistent, and helpful at every stage. After switching to Gorgias, their support performance improved dramatically:

• 80% decrease in resolution time
• 95% decrease in first response time
• 40% increase in efficiency

Before changing the product, try updating the messaging. Use insights from CX to rewrite descriptions, add size guides, include user-generated content, or even build a quick-fit quiz. Small tweaks help set clearer expectations and reduce unnecessary returns.

Ask your CX team:

“Which products are driving the most complaints, and what do customers wish they knew before buying?”

4. What confuses customers the most?

Confusion is a conversion killer. If a customer isn’t sure about how something works, what’s included, or whether it’s right for them, they’re more likely to bounce.

That’s why it pays to ask your CX team where customers get stuck. Is it a product feature that needs more context? A vague store policy? A missing detail on a bundle?

The good news is that most confusion is fixable. Start with the following steps: 

• Simplify your product pages
• Add quick-hit FAQs to your emails
• Use plain language and real examples

If you’re using Shopping Assistant, you can go even further. It can detect when shoppers are hesitant and provides real-time nudges. Like an assistant who knows all your needs, Shopping Assistant automatically surfaces the questions customers are likely to ask when evaluating a product, so they’re equipped with the clarity they need to proceed to checkout.

TUSHY, a modern bidet brand, faced similar challenges. As bidets aren't mainstream in North America, shoppers often had concerns about product compatibility and installation. They’d ask questions like:

• Will a bidet fit my toilet?
• Is installation complicated?
• Which bidet is right for me?

Without immediate answers, many potential buyers would abandon their purchase. To address this, TUSHY implemented Shopping Assistant, providing instant support. Taking this approach resulted in an 81% higher chat conversion rate compared to human agents and a 13x return on investment.

“The Shopping Assistant has been a game-changer for our team, especially with the launch of our latest bidet models. Expanding our product catalog has given customers more choices than ever, which can overwhelm first-time buyers. Now, they’re increasingly looking to us for guidance on finding the right fit for their home and personal hygiene needs,” said Ren Fuller-Wasserman, Sr. Director of Customer Experience at TUSHY.  

Ask your CX team:

“Where do customers get confused most often—and how can we clear that up sooner?”

5. Which products are frequently bought together?

Your CX team picks up on patterns that analytics sometimes miss. They hear which items customers ask about in the same chat, which products get added to carts together, and which pairings people reorder time and time again.

That intel is a goldmine for bundling and upselling. It helps you build smarter campaigns that feel relevant and drive real value.

Zoe Kahn, owner of Inevitable Agency and former VP of Retention and CX at Audien Hearing, emphasizes the importance of using AI to enhance customer interactions.

“A lot of that revenue was potentially missed revenue because these were customers sitting on the site, asking questions about the products, and wanting an answer now so they could purchase…Now, AI can answer those questions immediately and convert those customers.”

With Shopping Assistant, you can act on these insights in real time. It will surface personalized product pairings, bundle suggestions, or accessories based on customer behavior. All before they hit the checkout page.

6. Which products lead to the most returns, and why?

Returns cut into your margins and chip away at trust. Most of the time, they’re not caused by poor-quality products. They happen because expectations weren’t met.

Your CX team already knows which items come back the most and why. Maybe the color doesn’t match the photos. Perhaps the fit runs small, or the product description left out a crucial detail. 

Instead of pushing the product harder, reframe how you present it. Add real customer photos. Include fit notes or a sizing chart. Call out anything that might surprise the customer post-purchase. A little clarity upfront goes a long way in reducing returns and boosting retention.

At Pepper, an intimates brand specializing in bras for small-chested bodies, they recognized the importance of pre-sale education. When customers have sizing questions, their AI Agent, Penelope, can provide immediate assistance.

“Penelope takes the information we give her and responds better than a Macro. She tailors it so that it sounds like a natural conversation between two people,” said Gabrielle McWhirter, CX Operations Lead at Pepper.

By proactively providing instant support, Pepper improved customer satisfaction and saw an 18% uplift in average order value.

Ask your CX team:

“Which products get returned the most—and what could we do upfront to change that?”

CX + marketing = smarter campaigns, better results

Before you launch your next campaign, start with a quick sync with your CX lead. They already know what your customers need to hear. You just have to ask.

From fixing messaging gaps to surfacing the right products at the right time, these insights help you connect with customers in personal, timely, and relevant ways.

Tools like Shopping Assistant make it easier than ever to act on this data in real time. You can turn CX knowledge into dynamic recommendations, personalized nudges, and smarter discounts.

Ready to see how you can improve your online shopping experience? Book a demo to see how Gorgias Shopping Assistant engages customers in real-time.