Author: Tracey Ellis, CEO

My son loves Chipotle. Any parent of a teenager knows the struggle—if you could have invested in Chipotle stock back when your kid started eating burritos every other meal, you might be retired by now. They could eat it morning, noon, and night.

When it first came to be the in-store Chipotle meal was like an adventure. You’d watch the fresh ingredients being prepped, pick exactly what you want, and can make last-minute substitutions – you even got to taste an ingredient if you weren’t quite sure. It was all about control—ensuring the perfect balance of rice, beans, and protein. And the dollop of avocado that’s always a larger portion if you just put it right on top. And, if you skip the queso and chips, it’s relatively healthy.

But online ordering? That’s a whole different story.

The Digital Experience Shift: Where Convenience Becomes a Hassle

Consumers today expect seamless, frictionless digital experiences. We live in a world where you can order groceries with one click, track your pizza in real time, and get an immediate refund if your Amazon package doesn’t arrive. With technology at the center of our lives, people expect consistency, responsiveness, and user-friendly digital interactions—especially when they involve food, money, or time.

Ordering online with Chipotle, however, feels like a gamble because the experience is not consistent:

• You don’t know if the ingredients are available at that location.
• You don’t know if they are portioning things properly or skimping on key items.
• You don’t know if someone forgot an ingredient because they weren’t paying attention.
• You don’t even know if your order will end up in the right bag—or worse, in the wrong hands.

At least one in every 10 orders my son places has to be addressed with customer service for one reason or another. That’s not a small issue—that’s a pattern. And our last order was a problem.

Last Friday, he placed an order, got a “Your order has been delivered” notification, and—nothing. No bag at the door he was literally standing at. He called the Dasher (because Chipotle deliveries are handled by DoorDash), but there was a language barrier, and communication was impossible. The Dasher did send a photo of the order—a close-up of a Chipotle bag that provided zero indication of where it was left.

We had no choice but to reorder the same meal and take our only available option for customer support—a chatbot named “Pepper.”

For those who haven’t had the pleasure, Pepper is a classic bad chatbot experience:

1. Multiple form-fill prompts instead of an actual response.
2. Canned, pre-written answers that don’t address the situation.
3. Fake “agents” providing even more canned responses via email.
4. No direct way to reach DoorDash, even though they control the delivery.

Pepper, the Prime Example of a Chatbot Gone Wrong

A brand’s digital presence isn’t just about offering online ordering—it’s about delivering an experience that mirrors or enhances the in-person process. Customers expect seamless interactions, consistency, and reliability. When they choose to order through an app instead of walking into the store, they assume convenience won’t come at the cost of quality or service.

But when things go wrong, the lack of proper digital support becomes glaringly obvious.

Take Chipotle’s Pepper chatbot, for example. Instead of resolving issues quickly, it traps customers in an endless loop of form-fills, pre-written responses, and automated dead-ends. A chatbot should streamline the problem-solving process, not make it harder. But Pepper:

Lacks real-time intelligence – It doesn’t recognize the severity of an issue or prioritize urgent matters. A missing ingredient gets the same response as a completely lost order—no differentiation, no escalation.

Has no contextual awareness – It can’t access order details dynamically, meaning the customer has to input the same information repeatedly instead of getting instant solutions.

Creates more frustration instead of relief – Instead of a quick fix, customers feel ignored, dismissed, and powerless to resolve the situation.

Fails to connect with the delivery service (DoorDash) – There’s no direct communication channel between the customer, Chipotle, and the Dasher—leaving the customer stranded with no immediate way to recover their order.

The gap between customer expectation and actual experience is what drives dissatisfaction. In Chipotle’s case:

Customers expect real-time solutions → But they get a bot that can’t actually solve the problem.

Customers expect accuracy and transparency → But their food arrives missing ingredients or in someone else’s bag.

Customers expect responsiveness → But they get slow, pre-scripted, unhelpful interactions that waste their time.

When digital experiences fail to be consistent, engaging, or helpful, they don’t just inconvenience customers—they actively damage brand trust. Instead of resolving a small mistake, a broken digital experience amplifies frustration, making a fixable issue feel unforgivable. And in today’s digital-first world, frustrated customers don’t just walk away silently—they broadcast their experiences online. With reviews, social media, and word of mouth, a single bad experience can influence hundreds or thousands of potential customers. A frustrated customer is 10x more likely to share their bad experience than a satisfied one. So, when a brand like Chipotle fails to deliver on digital customer service, they aren’t just losing a single sale—they’re risking long-term damage to customer loyalty and brand reputation.

Today’s customers want:
Consistency – A reliable, repeatable experience every time they order.
Responsiveness – Quick, meaningful solutions, not dead-end bots.
Engagement – A two-way interaction where concerns are actually addressed.
Availability – The ability to get real-time help when things go wrong.
User-Friendly Design – Frustration-free, intuitive digital interactions.
…but most importantly, they want to feel valued.

When a digital experience fails, it doesn’t just inconvenience someone—it creates an emotional response. Frustration, anger, disappointment. These emotions drive consumers to:

• Complain publicly on social media.
• Leave negative reviews (Google, Yelp, Reddit, etc.).
• Tell their friends and family about their bad experience.
• Switch brands—because if someone else gets it right, why stay loyal?

9 out of 10 times, customers circle back to digital platforms to share their emotions—whether it’s a bad experience or a great one. Brands that invest in exceptional digital experiences create repeat business, brand loyalty, and positive word-of-mouth marketing.

When a customer walks into a Chipotle store, they have full control over their meal. They see the ingredients, choose exactly what they want, and can adjust portions or swap out items in real time. The experience is interactive, transparent, and predictable.

But when ordering online, that control disappears. Customers have no way of knowing if the ingredients they expect are actually available at that location, if the staff is following portion guidelines or simply rushing to fulfill orders, or if the order is packed correctly or missing key ingredients. The trust factor crumbles when customers repeatedly receive incorrect, incomplete, or poorly assembled meals. And when there’s no way to verify order accuracy before it leaves the store, the problem compounds.

• Implement real-time ingredient tracking so customers know exactly what’s in stock before placing an order.
• Allow customers to confirm their order before it leaves the store—this could be as simple as a photo or digital checklist confirming the order details before sealing the bag.
• Train staff to prioritize online orders with the same level of care as in-store orders, ensuring that digital customers receive the same quality experience.

A flawed partnership model between Chipotle and DoorDash leaves customers stranded when things go wrong. The most common issue? A complete lack of communication between the customer and the Dasher. Examples of this range from a customer getting a notification that their food has been delivered, but the order is nowhere to be found (pick me – pick me); the Dasher sends a photo of the bag, but it’s a useless close-up that provides no context on where it was left; or the customer has no way to directly contact the driver for clarification, leaving them frustrated and hungry.

When delivery is outsourced, customer support cannot stop at “not our problem.” Chipotle is still responsible for the end-to-end experience, even if a third party is handling the drop-off.

• Direct, in-app communication between customers and Dashers should be standard. Customers should be able to ask follow-up questions or request delivery confirmations.
• Photo proof of delivery should include a wider frame showing the location, not just a close-up of the bag.
• Escalation should go to a human, not a bot, when a delivery is lost or misplaced. Chipotle should route missing order complaints directly to DoorDash, rather than forcing customers to deal with an automated system that can’t actually help them.

When something goes wrong, customers expect fast, effective solutions—but Pepper, Chipotle’s chatbot, is designed to deflect, not resolve. Instead of offering real support, it:

• Forces customers through unnecessary form-fills instead of recognizing urgent issues.
• Offers generic, pre-written responses that often don’t match the specific problem.
• Provides no direct access to real-time human support unless the customer fights through multiple frustrating steps.

A chatbot should enhance customer service, not block it. The best AI-driven experiences are assistive, not restrictive—helping resolve issues quickly rather than making customers jump through hoops.

• Upgrade to a Conversational AI agent that can:
  • Pull up real-time order details so customers don’t have to repeatedly enter information.
  • Recognize when an issue requires a live agent and escalate immediately.
  • Process refunds and replacements automatically instead of forcing customers to wait for email follow-ups.

When used correctly, AI can be an asset to customer service. But when it’s implemented poorly, it does more harm than good—driving frustration instead of resolution.

There’s No Excuse – The Data is There

One of the biggest missed opportunities in Chipotle’s digital experience is the lack of proactive problem-solving. Instead of simply reacting to complaints, Chipotle has countless touchpoints throughout the order and delivery process where they could collect data, analyze trends, and make strategic improvements.

From the moment a customer places an order to when it’s delivered, there are multiple engagement points where Chipotle can collect insights and improve: Where the order is sourced from, In-app order details, Delivery process, and Post-purchase feedback.

Each of these engagement points provides valuable insights that could be used to enhance the customer experience, improve order accuracy, and strengthen brand trust. Here’s how:

One of the biggest missed opportunities in Chipotle’s digital experience is the lack of proactive problem-solving. Instead of simply reacting to complaints, Chipotle has countless touchpoints throughout the order and delivery process where they could collect data, analyze trends, and make strategic improvements.

Each of these engagement points provides valuable insights that could be used to enhance the customer experience, improve order accuracy, and strengthen brand trust. Here’s how:

Customers engage with Chipotle across multiple digital entry points, including:

• Website & Mobile App – The primary platforms where users browse menus, place orders, and track deliveries.
• Social Media & Digital Ads – Promotions, special offers, and influencer campaigns often drive people directly to online ordering.

How Chipotle Can Use This Data to Improve:

• Analyze how customers engage with their online menu—which items get the most clicks, which customization options are most popular, and which promotions drive the highest conversions.
• Track abandoned carts to identify where customers drop off in the ordering process—are they confused by pricing, unclear about portion sizes, or experiencing app errors?
• Personalize digital offers based on ordering behavior—if a customer regularly orders a burrito bowl but never adds chips, offer them a free add-on to enhance their experience.

By better understanding where and how customers are interacting with their digital platforms, Chipotle can optimize the user journey and remove friction points that lead to frustration and lost orders.

When a customer customizes their order, every tap and selection is a data point. These small actions reveal customer preferences, pain points, and common frustrations.

For example:

• If multiple customers modify the same ingredient (e.g., always requesting extra rice or no sour cream), Chipotle can adjust portion sizes to better reflect customer expectations.
• If a high percentage of customers abandon their cart at checkout, it could signal issues with price perception, hidden fees, or UX friction.
• If customers frequently edit or remove an item from their cart, Chipotle can analyze why—is it because of cost, availability, or lack of clear descriptions?

How Chipotle Can Use This Data to Improve:

• Optimize menu descriptions and pricing transparency to reduce abandoned carts.
• Provide smart suggestions based on past ordering behavior—such as “People who order this also love…”
• Flag high-error items (e.g., if a certain topping is frequently reported as missing) and improve staff training around fulfillment accuracy.

By analyzing customer behavior within the app, Chipotle can proactively enhance the ordering process and make it more intuitive, accurate, and user-friendly.

One of the biggest gaps in Chipotle’s digital experience is what happens after the food leaves the restaurant. Right now, customers are at the mercy of DoorDash—and when things go wrong, there’s no direct way to fix them.

Current issues:

• No real-time tracking for missing orders—Customers receive a vague “Delivered” notification without proof of location.
• Unreliable Dasher accountability—Drivers can drop off an order at the wrong address, take poor-quality proof photos, or fail to notify the customer properly.
• No way for customers to rate their delivery experience directly within the Chipotle app, meaning feedback is lost instead of used to improve quality control.

How Chipotle Can Use This Data to Improve:

• Require drivers to provide clear, location-based proof of delivery (e.g., a wide-frame photo that includes a landmark, not just a close-up of a bag).
• Incorporate a delivery rating system into the Chipotle app, allowing customers to rate their experience and report issues immediately.
• Identify patterns in delivery failures (e.g., if a specific location has a high number of misplaced orders, escalate concerns with DoorDash and implement stricter quality checks).

Chipotle needs to own the entire customer experience—including the delivery process. Waiting until a customer complains is too late. Proactively collecting real-time delivery insights would help ensure fewer mistakes, more accountability, and higher satisfaction.

One of the most valuable engagement points happens after the meal has been delivered. If a customer loved their food, Chipotle has an opportunity to turn that experience into a glowing review or repeat purchase. If a customer had an issue, there’s a chance to fix it before they take their frustration public.

Right now, Chipotle’s post-purchase communication is nearly non-existent. Customers who experience problems are forced to seek out solutions on their own, rather than being given an easy, built-in way to provide feedback.

How Chipotle Can Use This Data to Improve:

• Send a quick post-purchase survey via text, email, or in-app notification asking about the accuracy and quality of their order.
• Provide a frictionless way for customers to report issues—a simple “Something was wrong with my order?” button that instantly escalates the issue to a real support agent.
• Reward repeat customers with personalized offers—If a customer consistently orders from the same location, offer them loyalty perks or exclusive promotions to keep them engaged.

Why This Matters:

• Customers who have a positive experience are more likely to return.
• Customers who have a bad experience but receive quick resolution are more likely to forgive and continue ordering.
• Customers who have a bad experience AND a bad resolution process are the ones who leave negative reviews and never come back.

9 out of 10 times, customers circle back to the digital experience to share how they felt—whether that’s a 5-star review on Google or a rant on Reddit about how their burrito was a disaster. By actively gathering post-purchase insights and responding quickly, Chipotle can turn frustrated customers into loyal ones and strengthen its digital reputation.

From first click to final bite, Chipotle has multiple engagement points where they could improve accuracy, prevent issues, and enhance customer satisfaction.

Ordering Behavior → Improve menu descriptions, pricing transparency, and cart conversion.
Customization Trends → Adjust portioning and fulfillment accuracy.
Delivery Data → Improve driver accountability and quality control.
Post-Purchase Feedback → Address complaints before they become public reputation issues.

Chipotle already has the tools and data to fix these pain points. The question is: Will they use them? By better understanding where and how customers are interacting with their digital platforms, Chipotle can optimize the user journey and remove friction points that lead to frustration and lost orders. Chipotle is too big to be letting basic operational failures get in the way of its customer experience. If Chick-fil-A has gotten our order right every time, why can’t Chipotle?

Right now, Chipotle is coasting on the momentum of its brand—a name synonymous with fresh ingredients, customization, and fast-casual convenience. But success breeds complacency, and companies that don’t evolve with customer expectations quickly find themselves replaced by those that do. And Chipotle isn’t alone in this.

Chipotle became a household name because it offered something different—high-quality fast food, transparency in preparation, and a seamless experience. But today, they’ve outsourced key parts of that experience—delivery, customer service, and issue resolution—to systems and third parties that don’t uphold the same quality standards.

And they’re not the only ones. We’ve seen countless brands that once built their reputation on customer satisfaction slowly erode that trust by prioritizing cost-cutting, automation, and scale over experience:

• Starbucks revolutionized mobile ordering, but as they prioritized speed over personalization, customers started complaining about inconsistent drink quality and missing modifications—losing the handcrafted touch that made them famous.
• McDonald’s once dominated the fast-food space with its reliability and efficiency, but now, with self-order kiosks, mobile ordering, and understaffed locations, customers often find themselves waiting longer for orders that aren’t even correct.
• Amazon became the go-to for convenience and fast shipping, but in the push for automation, customers now battle inaccessible human support, unreliable third-party sellers, and inaccurate product listings that undermine trust.

Each of these companies became a leader by offering something better, but then slowly chipped away at the very experience that made them successful. And the result? Customers leave. Because when a brand stops valuing the customer experience, customers find alternatives—and loyalty dies.

To avoid falling into this trap, companies need to reinvest in the experience that made them great. That means:

Technology – Smarter AI, Not Just More Bots

Upgrade Pepper from a dead-end chatbot to a real Conversational AI agent that can:

• Pull real-time order details so customers don’t have to input information repeatedly.
• Escalate issues to live agents when needed, ensuring frustrated customers aren’t stuck in an automated loop.
• Automate refunds and replacements instantly, instead of forcing customers to wait for follow-up emails.

Service – Stronger Partnerships & Accountability

Define stronger SLAs with DoorDash that:

• Prioritize real-time issue resolution—if an order is missing or incorrect, a driver should be reachable, not a chatbot.
• Require clearer delivery photo proof, showing exactly where the order was placed rather than a vague image of a bag.
• Implement quality ratings for Dashers within the Chipotle app, giving customers a direct way to report and improve delivery reliability.

Process – Fix the Root Issues, Not Just the Symptoms

Improve order accuracy with AI-powered checks that:

• Flag frequent ingredient omissions and identify which locations need additional training.
• Verify orders against customer selections before they leave the store—a simple digital checklist or order confirmation screen could prevent hundreds of errors.
• Track and analyze which items are frequently reported as missing or incorrect and adjust staff training accordingly.

Speed alone isn’t enough anymore. Customers want: a seamless process from order placement to delivery, a digital experience that is as reliable as an in-person visit, a responsiveness when things go wrong, and the feeling that their business is valued. When brands treat customers like an afterthought, customers don’t just leave quietly—they broadcast their frustration, leaving negative reviews, posting on social media, and influencing others to follow.

This is the reality of the digital age—your reputation is built or broken in real time.

At its core, digital marketing isn’t just about driving awareness—it’s about driving experiences. Every click, order, and interaction is an opportunity to shape how customers feel about a brand. In a world where convenience and personalization are the expectation, the way brands deliver on their promises digitally determines whether they win loyalty or lose customers forever.

Marketers are uniquely positioned to bridge the gap between customer expectations and business execution. They have access to the data, the insights, and the customer sentiment that reveal exactly where things go wrong—and more importantly, how to fix them. But their influence can’t stop at just attracting customers. The most successful marketers ensure that what’s being promised is what’s being delivered. This means marketing has the power—and the responsibility—to push for change across the entire organization. Digital teams can inform product development, customer service improvements, and operational adjustments that make a lasting impact on the brand experience. When marketing advocates for the customer, the entire business benefits.

But if the customer experience is ignored? If companies prioritize scale over satisfaction, automation over authenticity, and cost-cutting over quality—then no amount of marketing can save them. Because today, brands that fail to put the customer first don’t just fall behind—they fall off completely. And when that happens, nobody wins.

So hey Chipotle if you need some help with your digital experience this should help. Enjoy the free consulting, I don’t charge extra for my guac! And for my son, he’ll be back at the store or he won’t be getting Chipotle.