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Rosie Bailey and how AI-powered Nibble is changing the chat game

DTC Growth Show · 2023-01-10 · 19 min

0:00--:--

Key moments - from our scoring

Substance score

43 / 100

Five dimensions, 20 points each

Insight Density9 / 20
Originality8 / 20
Guest Caliber12 / 20
Specificity & Evidence8 / 20
Conversational Craft6 / 20

Nibble is an AI-driven negotiation chatbot designed to intercept customers at critical abandonment moments - like when browsing a product page or about to leave a cart. Unlike traditional customer service bots, Nibble has a specific, narrow purpose: facilitating one-on-one micro-negotiations to close sales. Built by Rosie Bailey and co-founder Jamie starting in mid-2020, the tool uses advanced natural language understanding to interpret complex customer intents in a single message (e.g., recognizing when a first-time buyer mentions both a price offer and their new-customer status). Rather than forcing brands to script rigid decision trees, Nibble conducts conversations that feel human-like and engaging, with a personality that reinforces brand values - whether premium positioning, fair-trade commitments, or circular economy principles. Brands deploy it via behavioral triggers (time on page, repeat visits) as a pop-up, button, or side panel, keeping it visually distinct from customer service chat. The tool adds negotiated prices directly to the cart and passes checkout to the retailer's own payment flow (Shopify Pay, standard credit card, etc.). Current use cases span clearing slow-moving inventory, raising average order value, and navigating minimum advertised pricing (MAP) constraints. Bailey frames Nibble as a "nibble" - a small incentive that benefits both parties - rather than aggressive haggling, positioning it for Gen Z and younger cohorts who naturally prefer chat and mobile-first experiences.

Key takeaways

  • →Nibble uses AI-powered natural language understanding to interpret multiple customer intents in single messages, eliminating the need for rigid chatbot decision trees and enabling more human-like conversation flow.
  • →The tool is deployed via behavioral triggers (dwell time, repeat page visits) and sits visually separate from customer service chat, making clear it's for deal negotiation, not support.
  • →Nibble works across Shopify, WooCommerce, and Adobe Magento, adding negotiated prices to cart and routing checkout through the brand's own payment system without friction.
  • →About 50% of Nibble conversations reach a deal within one minute, and the tool helps not only recover abandoned baskets but also reinforce brand positioning and improve retention and margin.
  • →Future expansion beyond e-commerce includes circular economy (buyback negotiations for used goods) and potentially SaaS pricing negotiations, though the model remains data-hungry and e-commerce-focused for now.

Guests

Rosie Bailey

Topics in this episode

ShopifyWooCommerceCircular economye-commerce conversionNatural language understandingNibbleAI negotiation chatbotbehavioral triggersAdobe Magentominimum advertised pricing (MAP)

Questions this episode answers

How does Nibble's natural language understanding differ from traditional chatbots?

Nibble can recognize multiple intents in a single sentence - for example, when a customer mentions both a price offer and notes they're a first-time buyer, it understands both signals without requiring pre-scripted decision paths, whereas traditional bots parse each pathway separately.

What triggers Nibble to appear on a product page?

Nibble fires based on behavioral triggers like a customer visiting a product page twice within 10 minutes or dwelling on the page for an extended period, appearing as a pop-up, button, or side panel.

How does checkout work after a customer agrees to a price with Nibble?

After agreeing, the customer clicks 'I agree,' the negotiated price is added to the cart, and they proceed to the brand's normal checkout process with their existing payment methods (Shopify Pay, saved cards, etc.) - Nibble doesn't handle the transaction.

What platforms does Nibble integrate with?

Nibble integrates with Shopify, WooCommerce, and Adobe Magento via plugins and apps.

What are brands currently using Nibble for?

Primary use cases include clearing slow-moving inventory and outlet stock, raising average order value through upsell negotiations, and working around minimum advertised pricing (MAP) regulations.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

9 / 20

There are a handful of genuinely useful operational details - behavioral triggers, multi-intent NLP, MAP regulations as a use case - but the episode is dominated by product demo narration, light banter, and origin storytelling rather than dense, transferable insight for a B2B operator.

somebody's come to that product page twice in the last 10 minutes or they've dwelt on the page for a longer period of time. So then the chatbot fires up
about half the conversations reach a deal within about a minute

Originality

8 / 20

The outlet-section framing - using negotiation to clear inventory without signalling a fire sale - is a genuinely non-obvious use case, but most of the conversation rehashes standard chatbot engagement arguments and there is no contrarian or first-principles challenge to existing e-commerce wisdom.

using Nibble on the outlet section of your website for example just to reinforce the brand values, because often something's in outlet, not because it's damaged or really old, but because there's not the full range of sizes
we're looking hard at the circular economy, whether we can close the loop, whether we can do the buyback for you as well as the sale

Guest Caliber

12 / 20

Rosie Bailey is a credible practitioner - genuine founder with an investment banking background in large-deal negotiation who has built and shipped a real product - but she is early-stage and the conversation never surfaces operating data or lessons from scale that would elevate the score further.

I was an investment banker for my sins, but negotiating deals, big deals for international companies like Unilever or Tesco
we're working with the London Business School professor of negotiation, who incidentally has a fantastic TED talk with a million views

Specificity & Evidence

8 / 20

A few concrete data points appear (deal rate, time-to-deal, named platform integrations) but the episode is almost entirely free of customer names, conversion-lift percentages, revenue figures, or A/B test results that would let a listener benchmark the tool's real impact.

about half the conversations reach a deal within about a minute
We have Adobe Magento plugin and a WooCommerce plugin and a Shopify app

Conversational Craft

6 / 20

The host consistently leads the witness, answers his own questions, and shares personal anecdotes rather than probing the guest; there is zero pushback on claims, no request for hard evidence, and the questions are visibly rambling and unfocused throughout.

So talk about, I mean, it's an interesting season to be in e-commerce when I, and when I say season, I mean like this 18 months. Um, so talk about like, as you're going to, to brands, like what's their reception? Is this something, um, that they're saying, yes, this makes sense because it's a little overhead. Like I don't have to staff it per se. Is this a hard sell and easy sell?
Is there a concern there that, you know, there's, you know, there's the whole payment paralysis idea and now there's almost pop-up paralysis.

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Most-used words

nibble40deal24chat21customer18interesting12chatbot10brand10sure7negotiation6commerce6important6brands6first6different6point5engagement5

Episode notes

It's not uncommon to find chat on an eCommerce website. And it's not uncommon to find a bot-powered chat on an eCommerce website. But it is uncommon to find an AI-powered chat experience that is willing to negotiate with customers, and do so with ... well ... some personality. That's exactly what Nibble provides. Rosier Bailey, Nibble's president and CEO, chatted with the DTC Growth Show about Nibble and its potential uses across eCommerce. Read more

Full transcript

19 min

Transcribed and scored by The B2B Podcast Index.

The D2C Growth Show. Nibble has personality. Hey, Rosie, thanks for joining us. Thank you very much.

Pleasure to be here. Awesome. Well, tell us a little about yourself and about Nibble. Yeah, sure.

So I founded Nibble with a friend two years ago. Prior to that, I was an investment banker for my sins, but negotiating deals, big deals for international companies like Unilever or Tesco. and then I went to business school very late in life it was a bit of a midlife crisis I think and uh and met Jamie and Jamie had this brilliant idea for this negotiation chatbot and we talked and I introduced him to some people started helping him and then we decided given there was a pandemic and there wasn't much else to do and we were stuck at home we would build it so so from mid 2020 onwards we were building it so that's me In terms of Nibble, Nibble is an artificial intelligence chatbot, an automated chatbot, and it lets a brand negotiate one-to-one with customers to find what we call a win-win deal.

But sometimes that sounds a little bit like sales speak. So if you think about an e-commerce company catching a customer just before they abandon the basket, that's what our chatbot does. and has a little chat with them and says, hey, I can see you're interested in this item. Is there a price that works for you?

And the interviewing conversation should reach a deal. So, yes, that's super amazing. Coming from the, I came from the higher ed side and saw just how important chat was in terms of lift and converting prospective high school students who wanted to go to university and see the importance of chat. And the e-commerce side, when I was an operator CMO there.

So just talk about how you've seen just how important Nibble is and how it's learning. And frankly, it's like you said, it's the AI power. It's cheeky. I've used it, and it's interesting how it actually engages with the customer and isn't just simply another chat bot.

I think chat's so important. And if you think about the Gen Z and the younger customer cohorts, for them, it's totally natural to do everything either on a typed chat or on a voice chat. Even if I think about myself, I dictate text messages now, and I don't think I did that 18 months ago, because you're so used to achieving things on the go. And you might sit at your laptop and try and browse for something, but then you want to get it done, and you do it on the go.

And I think it's so important to have chat and make it feel like a WhatsApp experience, if that makes sense. So from that point of view, we see a huge amount of engagement, and we see a huge amount of honesty in the chat. and that's what's so exciting is people really engage with Nibble because we've given it quite an emotive personality and as a result it can reinforce brand values it can talk about the importance of being a premium brand or a fair trade coffee or a circular economy marketplace and if you start there you get a ton of engagement and so not only do you agree a deal but you might be able to walk the customer up or get them to come back a second time or improve retention as well as improving conversion and usually margin as well.

Yeah. I thought that was super interesting. And when I tested it with the coffee brand or, um, as you, you gave the coffee brand as an example, it was nibble was reinforcing the brand statement and reinforcing why this was somewhere you wanted to shop and somehow why the product was differentiated. How are, um, how are brands you're working with using this?

Is it to clear inventory? Is it for sales? Is it for to move low, you know, to slow moving stock? How are they using it?

We're seeing quite a lot of inquiries now about slow moving stock and clearing inventory. It does seem to be something people are concerned about around about now and going into early 2023. And when you've got too much inventory, the last thing you want is the consumer to think that it a fire sale or that you distressed And so actually using Nibble on the outlet section of your website for example just to reinforce the brand values, because often something's in outlet, not because it's damaged or really old, but because there's not the full range of sizes.

So you can't put it on your formal part of your site or something like that. So you can reinforce it. You say, look, you're very lucky to get this. It's such a great deal.

and have a little negotiation on it, or it's fairly unique, or it's just come back from the showroom, or it's a quick delivery item. How much do you want to pay? And you just reiterate your engagement on that item without necessarily looking like you've got a ton to clear. And then assuming everyone hasn't interacted with Nibble yet, walk us through.

So again, as I tested it, when you say, when you agree with the bot on a price, it actually then sends you straight to the cart. It provides you a link with a custom code and sends you straight on. So, I mean, it's obviously working to help conversion rates there as well. Yeah, so the way it works is usually many of our customers use it, what we would say, on a behavioral trigger.

So somebody's come to that product page twice in the last 10 minutes or they've dwelt on the page for a longer period of time. So then the chatbot fires up and it can come in as a pop-up or it can just appear as a button. and at that point somebody clicks the button and it opens a chat window looks a little bit like whatsapp and you have that natural language chat to try and get to a deal about half the conversations reach a deal within about a minute and then at the end of the deal you click i agree and it adds to the card the new price and then you can go straight to the checkout and check out and what we thought was really important is that checkout process is with the brand it's with the retailer and it's completely unchanged.

So if it's a regular customer who's got their credit details in, in, um, already installed with you, or it's a trust item at that point. And I don't think they want to necessarily deal with the chat bot at that stage. They want to deal directly with you. So that process is completely unchanged, but it's seamless.

So connect straight with your, I know you're integrated with Shopify. So if they choose ShopPay, there's that if, you know, and you're also in, I say Magento, but you're, you have Adobe plugin, correct? Yeah. We have Adobe Magento plugin and a WooCommerce plugin and a Shopify app.

Yeah. Awesome. So talk about, I mean, it's an interesting season to be in e-commerce when I, and when I say season, I mean like this 18 months. Um, so talk about like, as you're going to, to brands, like what's their reception?

Is this something, um, that they're saying, yes, this makes sense because it's a little overhead. Like I don't have to staff it per se. Is this a hard sell and easy sell? What do you, you know, and there's just so many SaaS options out there.

What are you, what are you finding as you talk to brands about nibble? Well, the first thing is, is we don't think there's anything like it. So there's no chat based make an offer solution. And so as a result, it's a little bit new and a little bit different.

So the first thing brands go say, why do I need that? And I've never seen something like that before. Then they play it and they realize it's got this very positive, very engaging, very fun character. And it's very, it's slightly gamified.

And so it's very engaging. And so then we normally see that brands who love that engagement, they love that fun. They're the ones who are the quickest to onboard. And then the people who want to solve a specific problem.

So they've got too much stock or low conversion rates, low average order values, because we can do boosting for average order values, or things like they're restricted by minimum advertised pricing regulations like MAP regulations. regulations. So it tends to be for a company that has a discretionary purchase where the customer might pause and have a quick think and look for a voucher code before they click buy. Interesting.

And I know, again, I just keep going to that it seems as brands are needing to cut back. But using chat in the past, I know I enjoyed using it as an operator when it was just me talking to the customer, but when it came to spinning up playbooks and spinning up nurture campaigns through a chat it was incredibly difficult and I just didn want to take the time to do it This is somewhere also where Nibble kind of takes away that need correct I think to be fair I think the technology has moved on a ton in the last three four five years And so the idea that the natural language understanding, so our chatbot can understand multiple intents in the same sentence.

So I'm a new customer. I hope I get a special deal. Hey, Nibble, what about 80 pounds? that that person has made an offer of 18 pounds or dollars but they've also given you a reason why you might want to treat them differently they're a first-time customer and they probably read on your into your website that you offer 10 off for new customers or something like that and so the natural language understanding you can get in these chatbots if you use an ai solution is so much more advanced so you don't now have to pick apart every pathway the customer might pass through the chat like a flow diagram.

If they say this, then take them here. If they say that, take them there. You can actually conduct it in a much more human-like way, which is a huge opportunity for engagement. Yeah.

And when we post this to the article in Bank Notes, if Rosie allows, she has a really interesting slide that breaks down a sentence and how the average chat bot we'll unpack a sentence first, how Nibble will kind of break it down into sections, which is really interesting. And if she allows us, we'll post that slide in this article as well with the podcast. But talk about what have you seen over the time you've been doing this in terms of consumer willingness to deal with not just chat, but to deal with a bot?

I think here in the States, it's still people are a little bit on the fence, like they want to talk to a real person. But I think to your point, Nibble almost takes them over that hump because it's personable. Yes. And I think a lot of times people don't realize Nibble isn't a person, which is funny, really, because we put a little blue face on it.

And we're not trying to dupe you. Do you know what I mean? We want you to know it's a chatbot. We don't want you to feel cheated or that you don't understand.

But a lot of times we get people going, I didn't realize this wasn't a human. It was so slick. and I think that's the thing that's got chatbots a bad name is they've launched in a very beta form and lots of people find it very hard to use I think that's the first problem the second problem is I think a lot of early use cases of chatbots were too broad and so they were hoping a chatbot would be able to answer anything and they went very ambitious and so as a result they didn't understand everything whereas actually nibbles trying to do something very very simple it's just trying to take your customer from browsing through to get a deal and buy and and it's a very and and we're very clear at the outset of the conversation this is nibble i'm here to help you get a great deal today not and and people don't mistake it for a customer service chatbot sure sure um which is important because we want you to go to customer service for customer service you'll get terrible customer service from nibble and yeah which is yeah that's interesting and one thing i forgot to mention is um it also you could the consumer not the consumer the the brand has the ability to to present nibble as like a typical chat icon or actually on the pdp level i like underneath like a cart button sort of option can you talk about that and and what you're seeing in terms of different conversion there so we can trigger nibble as a button underneath the add cart button that looks like a different option.

And what we find is some people ignore that and then just pay full price. So for the brand, it's not a problem. And then other times we can launch it from a pop-up or a pop-in from the side, but always slightly differently placed than your chat icon for your customer services. Because the vast majority of our clients have a customer service chat capability, often going through to a human.

So we tend to make sure that they look separate. Yeah. Is there a concern there that, you know, there's, you know, there's the whole payment paralysis idea and now there's almost pop-up paralysis. Is there, is there a concern there that I guess to your point, you're just making sure it's differentiated and it's showing like, I know, I think on sites it says like get a deal or ask for a deal or something like that.

So definitely kind of differentiating there. You can use different copy. We don't mind what copy you use. Some people say negotiate, some people say barter, some people say make an offer.

Funnily enough we were worried it would get confused but because it only triggers in certain circumstances because it very clear what it there for you be surprised how little that happens and if you say hey nibble can i speak to a human nibble can pass you over so okay so what's well i guess why nibble why the name nibble um do you know i think it was a thesaurus and the word haggle and and i don't know if it's true true in American culture, but haggle in an English culture has a slightly negative connotation.

Sure. You sort of feel like you have to, frankly, fight to get a good deal. That's sort of the connotation. And we wanted to be much more about a small incentive to get the deal done and much less about deep discounts or fighting to get the best deal.

A nibble is supposed to be a win-win outcome. The retailer gets a sale right now at a small discount. The customer gets a personalized deal exactly when they want it on what they want. And they don't have to fight for that voucher code, spend 10 minutes browsing the internet for a better deal.

It's supposed to be a nibble, a small thing that brings everyone together. That's interesting. That's cool. So what's next for nibble?

Are there other potential use cases in the future, like across different, you know, maybe government verticals or healthcare or something different where people are trying to get information or is this strictly going to be an e-commerce platform? Somebody asked me yesterday whether it would get involved in marriage counseling. Oh my word. But I don't think so.

Nibble would just find an appropriate middle ground for everybody. What's the win-win outcome here? We're building an e-com because it's an AI tool, it's data hungry. And e-commerce is a great place for us to build the database to make the dot smarter.

Every time the bot negotiates, it gets better at it. And we're working with the London Business School professor of negotiation, who incidentally has a fantastic TED talk with a million views to improve that negotiation skills. So we'll definitely start in e-commerce. We're looking hard at the circular economy, whether we can close the loop, whether we can do the buyback for you as well as the sale, right?

So you've got your old mobile phone and you want to sell it onto, to get a new mobile phone, right? And you put all the details in and it says, oh yeah, your mobile phone's worth $40. And you go, well, I thought it was worth at least a hundred, you know? And then you open another tab and look on eBay or whatever.

And it's exactly the same process. So maybe we can negotiate a deal for you on your old mobile phone where there's an incentive to buy a new one. Maybe you don't get the extra money in cash. You get it in credits against a new phone, that sort of thing.

So there's a circular economy play that we're very seriously exploring. And then I wonder if it'd be nibble for SaaS next, but anywhere that needs a negotiation. We're very interested in that micro bit of the negotiation. We're very happy if you want to put it somewhere else.

That's interesting. Yeah. Nibble for SaaS is super interesting. You can see nibble for SaaS would be, do you want to pay monthly or annually and I can do you a better deal annually?

Or do you want to get the enterprise package, not the professional package, and I could do you a deal? And it's not beyond the wit of man to put that into a chatbot. No, certainly not. I think about the marriage counseling bit.

I think less marriage counseling and more posts and who's getting the house and who's getting the kids on what weekends and coming to an agreement on Nibble on that. I think Nibble's very nice. Nibble would just be, no, your bum doesn't look big in that. Yes, I think it's fantastic.

Oh, my word. Well, this is so interesting. I know when I first heard about Nibble through a mutual connection, I was just super interested and hopped right on to check it out. And it's just as interesting as it sounded.

So good luck to you and good luck to Nibble and the team. Tell us where to find you. I know you're more LinkedIn than Twitter. So tell us where to find you and where to find Nibble.

So our website is nibble.shop. So you can find us at nibble.shop.

And I'm Rosie Bailey. And I'm on LinkedIn. And I'm nascent on Twitter as The Hon Rosie. But you can find me both places.

Awesome. Awesome. And I'm sure we'll be seeing Nibble in more places. Looking forward to it.

Thanks so much for chatting with us. Thank you so much, Ian. It's been a pleasure.

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