The Trailblazers Experience Podcast

EP71 Rosie Bailey CEO and Co-Founder of Nibble -The Art of Negotiation Rosie's Transformative Career Path

• Ntola • Season 4 • Episode 71

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How do you transform mathematical prowess into groundbreaking entrepreneurship? Rosie Bailey, the dynamic CEO and co-founder of Nibble, an innovative AI negotiation tool, joins us to share her remarkable journey from the world of mathematics and investment banking to trailblazing in tech. Rosie's story is a testament to the power of seizing opportunities, working with dedication, and strategically utilizing one's strengths to navigate bold career transitions. She opens up about the motivations and challenges that propelled her from a structured banking career to the unpredictable, yet rewarding, world of tech startups.

Chapters
00:00 Introduction to Rosie Bailey and Nibble
01:42 Rosie's Early Career and Education
04:55 Transitioning from Banking to Entrepreneurship
08:35 Pursuing Further Education and Meeting Jamie
11:15 Founding Nibble and Initial Challenges
14:30 Transferable Skills and Leadership
18:41 Negotiation Skills and Their Importance
23:44 Negotiation Tips for Success
31:10 Navigating Gender Dynamics in Negotiation
35:55 The Evolution of AI in Business
43:16 Ethics and Values in AI Development
47:40 Work-Life Balance: Finding Your Non-Negotiables
49:46 The right support system
53:47 Trailblazer Takeaways: Key Insights for Success
54:51 Trailblazer Takeaway Tips
58:21 Outro

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Nibble    Nibble - The world's most experienced AI negotiation platform
Linkedin :   (1) Rosie Bailey | LinkedIn
Linktree   Nibble Technology | Instagram, Facebook, TikTok | Linktree 
Watch Youtube Interview here :https://youtu.be/Zx7z9ESthN4


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The Trailblazers Experience:

Welcome to another episode of the Trailblazers Experience podcast, the podcast where we have candid conversations with women sharing their incredible career journeys. Today, I'm honored to have Rosie Bailey. I describe her as a dynamic CEO, and she is co-founder of Nibble, a revolutionary AI negotiation tool that is, I think, trailblazing in the industry and going to really make some key impacts to businesses. She has had an illustrious career and I look forward to discussing it. You know doing deals and working with companies from Wagamama, unilever, jimmy Choo. We know the shoes, and now she's channeling her expertise in Nibble. So welcome, rosie.

Rosie Bailey :

Thank you very much. It's an absolute honor to be here. Lovely to be invited.

The Trailblazers Experience:

And I was saying before we started the podcast. I think it's so great to have the opportunity just to take a step back and reflect on you, the person, rosie, and your career and everything that you've done. So looking forward to this conversation, thank you, Thank you. I don't know about you, but sometimes when you look at LinkedIn, you look at someone's profile and just say how did they get there? They're so amazing. I don't think I could do that. I don't think I have the skill set, or it's going to take me too long, or I don't have these connections. Before we talk about you actually leaving a successful career to start Nibble, we talk about you actually leaving successful career to start nibble startup talk to me about your background and just sort of where you're from and how that's even come to be, and just sort of your early stage, your early days.

Rosie Bailey :

Also. I mean, I'm a very lucky person, right? I come from a stable family, supportive base, good education, you like. I'm very lucky and I studied maths at university. And at university there were lots of professional services firms that came to your university and said, hey, do you want to join? And so I went along to all of the standard things and applied and got a summer job in banking and ended up in banking.

Rosie Bailey :

I wasn't. I don't think I was desperately strategic. The reason I chose maths at university is it was the subject I was best at at school, which had two advantages. One is it was easier to get into a good university and secondly, once I got there, I could focus as much on making friends and having fun as I could on the course. You know, I don't think I was extreme one way and I wasn't extreme the other way. I'm quite a goody two-shoes. Do you know what I mean?

Rosie Bailey :

And I think when some people look at, when I look at, other people's careers, I think it's easy to assume it was very deliberate and mine was probably very opportunistic, but I would say not flighty. Do you know what I mean? Like as in, you looked at the opportunities that presented themselves to you. You picked the one that you thought was best and then you went for it with all of your guts. Do you see what I mean? So when I went for maths at university, I'd found maths quite straightforward at school. I can tell you I found it really hard at university, but I knuckled down, I tried hard and I got good grade.

Rosie Bailey :

And I think the same goes for investment banking. They do recruit really strong candidates who have great academic backgrounds. However, once you're through the door, by hook or by crook, it is really the people who knuckle down and work hard who make it, and I think that may well be a lesson for life. That may well be something that is true for everybody. If you sit and you look at what are the options laid out before you today, what's your best option that you could do? Pick it up and do it the very, very best. It may not be what you want to do for the long term, but if your boss in today's role says this person's a superstar, I can tell you that will unlock the next thing, whatever it is, whereas if they, if your boss, says, yeah, they seem okay, but they're not that committed to me and they're always looking at past my shoulder to see what the next thing is. You know, they'll feel they won't push you, they won't give you them there's something to be said about the logical approach, isn't it?

The Trailblazers Experience:

you were like, were like well, finish school, I'm really good at maths, let me knuckle down and just do that so that I can have fun at uni. And actually, you know, focus on something that I think I'm relatively good at, and that's even just a lesson for life in general. To your point of just focusing Focusing being, I wouldn't say, strategic, but if you can focus on one thing and do it really well, that usually opens doors to other things as well.

Rosie Bailey :

And accept what you've got. Do you know what I mean? I was lucky, I had skills in maths.

The Trailblazers Experience:

but if I had skills in geography, I tell you that's what I would have been studying, and so you enter into the investment banking world, which is, you know, either working for the big four and you build a career there. What, then, was the turning point for you to say I've had enough of this.

Rosie Bailey :

I actually want to do something different. I think, honestly, when you're in there and you're making the decision, it probably feels more like push factors than pull factors, and then when you look back on it, you repaint it as more pull factors. You know, like I'm really really glad I am where I am, but would I have left if I had been enjoying it or reaching my potential? No, of course I wouldn't. I was sitting there getting a little bit more frustrated perhaps. I mean, not everyone in investment banking is charming, or sometimes they're charming on the outside. It's a tough environment and they don't make any bones about that, right, and so it's a top dog environment. And if you feel, feel like you're not being the top dog, then sometimes some of the opportunities that you want slip away from you. But then when you look at it logically, you say it is a very up or out culture, right. And then you start looking at the opportunities which are hard to get and and seem unreachable. But at the same time in your heart you say, even if I could reach this, even if I had the potential to be head of the group, section leader, head of Europe, head of the bank, is that really a job I, I would enjoy. And then you start to be honest with yourself and say, well, kind of, actually I've done really well to get to where I've got to. I'm a managing director, which is sort of partner level. You know, got a team, my team really liked me, but actually I don't really want that next one. It's not available to me anyway. Right, because I'm not, I'm not, I'm not in that right position at the moment. Why don't I look outside and redefine success?

Rosie Bailey :

And I think for people in very competitive environments, leaving, leaving feels like failing, definitely Always feels like failing, and there's usually a lot of push factors, a lot of what I didn't get, that promotion or my bonus wasn't what I wanted it to be, I didn't get allocated the prestigious projects you know, and that feels like failing, especially when you've ticked every box up until that moment. Failing especially when you've ticked every box up until that moment. But then you go out and then you redefine success and you say it was failing. If that was your only definition of success. But actually, how happy am I to be? I'm like sitting here, I'm leading a business in the AI revolution, at the cutting edge of technology. I'm not a natural technologist, but I've found my way here, and would I ever have done that if I hadn't felt a little bit pushed out of a previously successful career? No, no, do you know what I mean? So I think change is very, very hard to embrace. Sometimes change gets pushed upon you.

The Trailblazers Experience:

It's so interesting. I was listening to Trini talking about how she actually started in the investment banking world and how it was. You know, it's ruthless, it's cutthroat, it's really. It is a man's world in a way. But you have so many lessons.

Rosie Bailey :

It's certainly a macho world if I can put it that way it's the traditional traits we associate with macho men, exactly.

The Trailblazers Experience:

Yeah, but there are a lot of transferable skills that she's taken from there to sort of help her with her business as well. They might be one for nipple as well, thinking about that.

Rosie Bailey :

Yeah, yeah, yeah, maybe give her a shout.

The Trailblazers Experience:

But yeah, I digress. But yeah, defining what is failure and change. Change is good. So transitioning to tech, I mean, tell me the story about, obviously, so you left and starting Nibble meeting your business partner, talk to me about that transition. I went back to school.

Rosie Bailey :

What? Crazy, yeah, and funny enough. I was walking down the street in the West End between meetings and I bumped into an ex-colleague of mine who I'd worked with very closely but lost touch with over the last, say, 18 months and I said, hey, what are you doing? And he said, oh, I'm studying at London Business School. And I said, no, you'll never. And he said, well, I've got 20 minutes between meetings. We sat in like a Cafe Nero.

Rosie Bailey :

By the way, there's a cafe near behind Green Park where all the hedge funds sit and I think more deals get done in that coffee shop than anywhere else in the whole city.

Rosie Bailey :

Anyway, we sat there in this coffee shop this like, very like, anyway, normal coffee shop and he told me all about this course at London Business School, which is a sort of MBA course, but for geriatric MBAs, right, so anyone over the age of 36 or something, but for geriatric MBAs, right, so, anyone over the age of 36 or something. And it's all the same sort of fundamental learnings, but it's very much focused on people who are late career. So it's leadership strategy, change, career change much more as a focus, much less hard skills, much more soft skills. And he'd done that for a year and then was using that to transition into a different role in a different place and a different focus, and it just sounded so exciting and I think I was really at the end of my tether and I never normally make these sort of impulsive decisions but I literally looked up the course that night, made an online application, did an interview and within a few weeks I had a place.

The Trailblazers Experience:

That's interesting. Was it one of those? Was it like an executive MBA that you were doing?

Rosie Bailey :

Yes, so it's like an executive MBA I'm not very good at all the terminology, but it's full-time and it's one year. And you arrive and everyone's sort of full of the bluster yes, I was pretty much CEO, you know and then after about a week everyone's like I missed the promotion, that's why I'm here and after about a month they're like I'm a complete failure. And then you spend the next 11 months building back up to I'm not a complete failure, I'm really pretty good, but I really needed a change. And then you have these amazing cohort of new friends who will build you up and open your eyes. You see what they were doing, which is different, and you see what they. They see what you were doing, which is different and gives you more ideas. You might want to change country. You might want to change industry. You probably don't want to change everything all at the same time, because that's really hard it sort of gives you the space just to step outside of yourself, isn't it?

The Trailblazers Experience:

take a step back, learn something new, um, and and and refocus. Okay. So you're doing that for a year, obviously very costly, um, and you're thinking, okay, this is, this is giving me some benefit. What happens at the end?

Rosie Bailey :

so I met jamie we the punchline is, we founded nibble together and he had this mad idea that you could negotiate with computer, which I thought was privately. I thought was pretty crazy, but he needed a bit of help. So I introduced him to a whole bunch of people that I thought could help and, um he we met somebody who said, oh my god, this is the best idea I have ever seen. I'm the ceo of the largest retailer of watches online. If you build it, I'll put it on my website. And we were like oh, that's enough. Needless to say, he never did put it on his website. We're on 200 different websites instead. But that was enough of a push to say well, let's make this real. And meanwhile, at the same time, a headhunter from my old life phoned me up and said there's a job leading a team. At the same time, a headhunter from my old life phoned me up and said there's a job leading a team at the biggest investment bank in the city.

Rosie Bailey :

So an inflection point isn't it, would you like to do it? And I said, oh yes, of course. So I went to Canary Wharf and I took the lift up to the 25th floor and I sat down and I met these very impressive bankers and I took the lift back down and as the lift is floating back down to ground, I say to myself I flunked that interview. I completely, completely flunked the interview. I knew I didn't even need any feedback. Everyone was very polite, oh, nice to meet you.

The Trailblazers Experience:

You know, like no in hindsight, did you think you flunked it?

Rosie Bailey :

because really you, it wasn really what you wanted to do and I walked out and the sun was shining in Canary Wharf and I waved at my ex-colleagues in the next door building and I thought that's the end of that then and I was super happy and it was fine.

The Trailblazers Experience:

That's so interesting, isn't it? So you build this career in this sector, doing really well, having some milestones, and you know know, take an executive MBA, meet some interesting people who have a different way of thinking and thinking about technologies that didn't even exist. If someone told you about AI 20 years ago, you'd be like what artificial?

Rosie Bailey :

what. And if somebody had said, do you want to do this career? I'd say, look, it sounds interesting, but it's not for me. What qualifications do I have? And because I met jamie and I helped him and he said let's do this together. And I said, well, I'm sure I can help and and you just build into it. And then, before you know it, there you are, and then chat, gpt arrives, and then you're suddenly at the cutting edge. And but it wasn't. I didn't know it was going to work out that way. I just knew I liked jamie and I thought it was worth trying to help because he probably had quite an interesting idea and, although I could be very cynical about it, maybe, just maybe, this is going to be huge, you know.

The Trailblazers Experience:

That's a lot of it. Isn't it About finding your business partner or starting a team or your next role? A lot of it is. Yes, of course, there are some skills that you need to bring there that help, but it's about the relationships, isn't it? Can I actually work with this person? Can I envision building a company together with this person? Can I envision doing some deals or just going through the highs and lows, transitioning from finance to tech? You could say there are some transferable skills, but did you face any initial challenges?

Rosie Bailey :

Because there are always challenges at the beginning, I think the really important thing, and I think that you have the opportunity as you get later in your career, to be more specific in your skills, to sort of meet early in your career. It's very good to try and learn everything and you may go into something saying right. You may go into finance saying I only got maths GCSE, I'm not sure if this is going to work. Well, you can do a finance career with maths GCSE because it's all accounting and accounting is adding up right and sometimes subtracting and very rarely multiplication, and you know so you can do that. And so at the beginning of your career you say I need to learn, I need to skill up, I need to, but as your career grows, it progresses to. I need to understand what I'm really good at and I need to be very cognizant of what I'm not good at. I need to not be embarrassed about that. I need to go and find ways of making sure I'm in a team environment or I'm working with people or I'm in a role where those those skills I don't have are compensated for. And that's where, if you work in a partnership, as Jamie and I do, the magic comes is when you're good at different things. Right, and I think it's the joy of being slightly later in your career that you can say well, actually I'm never going to be a superstar at that. I'm going to go and work in an environment where I don't need to be but where I need to bring people in to be a superstar.

Rosie Bailey :

And just while I was a banker, I joined the board of a STEM education charity and I did it mostly for my own personal development, I'll be honest, you know. But then I grew into being hugely passionate about the cause, which is really exciting. But one of the things I had to do was I had to chair the audit committee because they needed somebody to chair the audit committee. Now, normally, as a non-executive director, you're not allowed to do that unless you're a qualified accountant, and I'm not a qualified accountant. I know a lot about accounts and finance because of what I've done, but I don't have the piece of paper or the qualifications, so I'm not as deeply expert.

Rosie Bailey :

And I sat on this audit committee and for the first three meetings I read all the papers and and I was woefully like under confident because I knew that I was the only person in the room without that qualification, who wasn't an accountant and I didn't have the depth of knowledge that everyone else did. But then, after a couple of meetings, I realized well, they all know that too. Do you know what I mean? And I am not here because I'm more expert. For the first time in my career, I am here to bring the expertise to the table, and my only job is to make sure the right questions are asked and answered.

The Trailblazers Experience:

That is such a good thing that you've actually talked about.

Rosie Bailey :

So sometimes you know the question, but sometimes you don't even know the question, right? Yes, your only job is to try and draw the question out from somebody who might know it and draw the answer from the other person, and and, and not let things get swept under the table. And that was my first role, where it was dead obvious to me and to everyone that I couldn't be an expert anymore.

The Trailblazers Experience:

That's the penny drop kind of moment, isn't it? I think, when we, or when I speak to young people coming up in their careers and so on. You mentioned something really interesting before about you know, depending on the stage of where you are in your career, you need to have different focuses, you know, and if it's honing that skill set for the job that you're doing and then as you rise and get into leadership, management board roles, etc. It is more about what you've just said is asking the right questions and then so that you can make the right decisions, and having the right people around the table. That is what drives successful businesses, because they're able to solve the problem at hand and cut the BS, really, and get to the nitty gritty, and that's a skill set in itself.

The Trailblazers Experience:

Good leaders that you see, whether they're CEOs or chairman or C-suite it's a skill to actually listening to the noise in the room, asking the right questions to get the result that you need. And I suppose when you're running a startup so you've got obviously you've started Nibble you know that you have to pitch and speak to lots of businesses. You're having to understand their problem, but also the problem that you're trying to solve with your and convince them that Nibble is the tool that they need, isn't it as well?

Rosie Bailey :

Yeah, I mean that's sales, and and if there's one thing, I've got three little girls now and you do wonder what careers your kids are gonna do, don't you? And? And you do look at all the things you've done well and the things you've not done well, and you probably overemphasize all the things you've not done well.

Rosie Bailey :

I'm not gonna let them do that and if there's my one is they're gonna do I'm going to make them apprentice to an estate agent or something like that. I'm going to make them go and do Saturday jobs for the local estate agent because you've got to be able to sell yourself pitch. It's even called an elevator pitch because I think it has come from america. But the idea I was once in the american bank I worked for and I was mid, mid level, you know, and I got into the lift with this super senior guy who I think had been briefed that I'd done something good and and he, in the spirit of trying to be helpful, goes hey, that's Rosie, isn't it? I'm like, yes, gives me this massive high five, touch me. And then he's like so what are you working?

Rosie Bailey :

on at the moment and I was like, oh, some projects. And then the elevator doors and he walks out and I'm like, hmm, that was an opportunity, exactly.

Rosie Bailey :

Yeah, you need to have that pitch all the time and and and I do think I do think it's probably not culturally quite so relevant you know english but I do think having that pitch ready all the time and being able to answer it in an optimistic and a proud moment, it was quite interesting. One of the One of the lessons I did at London Business School was, you know, like they did some for career, you know, interview prep, that sort of thing. And one of the things they said is like why don't we do an elevator pitch? And everybody groaned because they thought it was naff and we're all in our forties. Do you know what I mean? It was like what and I know you've just gone through a career change so you'll recognize this but you have to get quick. You have to get quick at saying well, who are you? And it's a party or a social event.

Rosie Bailey :

And for me, because I had a bit of baggage from banking, there were some things that made me sad about banking. There were some things that I felt I'd missed opportunities or I hadn't done the best I possibly could. They were like so so what was good about banking? And because it was a fresh memory, it was kind of. And then then you suddenly think of bad things jumped your mind. They're like what was good?

Rosie Bailey :

And I said well, the other day, actually, I phoned up somebody who used to be a client and said could we have coffee because I need some advice? And he said, what about tomorrow at 10? And he's normally takes six months to get in his diary. And they're like so do you think you built some good relationships? And I'm like, well, yeah, I think I have, because he's like CEO of a foot company. And they're like you have yeah. And they're like, oh, that's a really good thing that you know and you have to then. So I then developed this whole pitch about how banking had given me not just finance skills but relationships for life, and those relationships were building my network, which was allowing me to go and deliver value as a non-exec to other places. And it was just, yeah, the elevator pitch, I think, is so important I've now completely lost my train of thought. I've gone off on a tangent about elevator pitches. No, no.

The Trailblazers Experience:

I mean certainly back. I mean the elevator pitch is so important and you're right, it is an Americanism, if it's worth calling that. Because in high school, so when I was growing up, I went to international school which sort of was adopting the American way of teaching, and they used to have show and tell. So you do these projects, you know, create a volcano project, et cetera, in primary school, and it was show and tell. Their thing was your parents help you with it or you do it yourself, and then you need to present it in five minutes in front of the whole class. And that, culturally, yeah, that is why americans are very good of being on their feet presenting. They're learning it at a very early age, where it's sort of in the uk school system or european, it's sort of in the UK school system or European. It's probably when you get to that specialist level that they now start saying now present. And at that point it should be a muscle that you're flexing and honing early on.

The Trailblazers Experience:

You can improve or not, but it doesn't matter yeah yeah, and it's key what you said about know you have built that career and, yes, you should leverage those contacts. You should. You understand how the investment world works. You probably understand what a VC is looking for, or private equity. So it's actually a gold mine for any startup to have someone who has that background as well and understand how to talk the talk. But I suppose sometimes you need that change in career to actually realise, actually, this is the toolkit that I have, that I've brought with me, and what's transferable and why, exactly, exactly. So Nibble's been going on for a few years, obviously, and do you think you've had to now adopt the negotiation mindset, just overall?

Rosie Bailey :

Oh, my God, Completely Like I. Probably, if you'd asked me five years ago, I would have said I hate negotiating, right, I hate it. Of course, I love it now Totally, totally Cool with it. But also we negotiate everything Like if any of our suppliers have listened to this podcast, they'll know that we negotiate everything because it's our brand, right, you know like it's our brand.

Rosie Bailey :

And actually what we're learning and what I am learning is I don't just talk the talk now it does improve your relationship situation where a client said I can't pay you the full fees and actually they were in the middle east and so I think it was culturally quite to be expected and it was really early days, and I I went back to jamie and I said this client, they, they want a discount. I just looked up their volumes, right, and we've had volume based pricing at the time and they're paying like two dollars a month for something. I was like it was like I theoretically I could give them a hundred percent discount and it would make no difference to us, but really, why is he asking for a discount on $2? Anyway, so I sort of went back and we kind of rehearsed it and went back and we said um, we're delighted to offer discounts to our high volume clients. And um, you've said that you're a growth player, so so, so when your volumes reach x, we'd be delighted to talk about an. X was like in the tens of thousands of dollars, not two.

Rosie Bailey :

And of course, he looked at his numbers and he said, yes, we're a very ambitious company. That's really fantastic, and we'll call you back when we get to that level and actually a level set. Do you know what I mean? Because he told me a bit about their growth ambitions and he explained that we were only being used on a very small subset of the possibilities in his organization and I learned all about his business that way.

Rosie Bailey :

And he learned that we had the ambition to serve enterprise clients, you know, and that this was just a sort of get to know you, relationship building. And actually, if I'd just gone either no by email or yes by email, who cares, don't bother paying us for the next six months because I was staring down the ballot barrel of a 12 dollar loss, you know, um, I wouldn't have learned any of those things. And and so it is really, really important to have a conversation, it is really important to learn where each other is coming from and it can be done in a really friendly way. It doesn't have to be like an FBI hostage negotiator naming no names, but it doesn't have to be.

The Trailblazers Experience:

Yeah, and it's an important skill set that I think especially women should learn, and that was also one of the things that I wanted to ask you in particular as to as we look to empower women. We've got International Women's Day coming up in a few months and we want to make sure that as many women have a seat at the table as possible. And I was listening to Emma Greed, who is co-founder of Skims, good American, etc. And she talked about how, when men network and get together, it's to get shit done. So literally they want to connect each other with as many people as possible problem solve, get stuff done.

The Trailblazers Experience:

When we women network, we want to build community. You know, we want to have a chat, we want someone who empathizes with what we're going through, but we also need to adopt that mentality of, yeah, we're coming together to do all of that, but we also need, in negotiating for your career whether it's for a pay rise or career jump or, if you are a business owner, knowing when to ask for more. What are some of the negotiation tips that you can share? A from your career that you've spanned, you know, in banking, but also now as a CEO and a founder of a startup where you've understood what it means to have so many pitches as possible and now getting into all these retailers. I mean, your business is building traction. We're going to talk about that in a minute, but what are some of the tips you were to share? Top negotiation tips for people to take into 2025? What would they be, especially women?

Rosie Bailey :

There's only two. There's only two, there's only two, and if you've nailed these two then you can go to second base, right, but most people don't nail the first two to their own satisfaction. So the two are be prepared and which is a bit like your elevator pitch, and then the second is go first. So there's only two, and if you do those two then mostly you'll be fine and there's more stuff you can do. But really honestly, it's all in there.

Rosie Bailey :

So in the be prepared it's let's say it's a salary negotiation. It's actually saying well, what do I like, want, need? So I would like a salary of 80,000 minimum. My stretch target is 90. But he's actually telling yourself that and it's probably writing it down. And then it's saying I would like I don't know hybrid working three days a week. Fine, write it down. If you had to swap hybrid working for some salary, how much salary would you swap for it? Because otherwise you can get bamboozled because somebody could say oh, you want hybrid working three days? Well, we're willing to offer it for five days, but only 70,000 on pay.

The Trailblazers Experience:

So it's not playing out the negotiation in your head saying, actually I've asked for this, but what if they say this? What's my response?

Rosie Bailey :

So you just put a value by everything, so that you can't be bamboozled, so that if somebody gives you a counter offer you can actually literally almost like maths, you know write it down and just say, okay, well, she, she's given me this, so I guess that's 10 more here and five more here, but six less there. Just so don't mean so that you don't end up agreeing something and then you get back and in the cold light of day you add it all up and you realize that you've given ground that you didn't realize. Why go first, and always go first? Because then the conversation, the next step in the conversation, is about dragging you towards they want to agree, not you dragging them towards where you want to agree. So so you will always be in a more powerful position. The way to think about this.

Rosie Bailey :

I'll be honest, this was an exercise at London Business School, right, and it was a very simple negotiation where, let's say, the price needed to be between 70 and 100. And we were both given a scenario whereby that was going to be agreed, and I looked at the information I had been given and we were given parity of information, and so I sort of thought through what they would think, and I thought gosh, they'll basically say a fair price is somewhere between 80 and 85. So I guess I'll ask for 87. It was in my head.

Rosie Bailey :

So then the whole conversation now is between 70 and 87 and all they're going to do is argue extremely hard somewhere in that range and it means I have automatically excluded any possibility of getting between 87 and 100 wiped that out completely and all I'm doing now is fighting to try and get somewhere between what I thought was 80 and 85, but they're still playing in the whole of the 70 to 80 range.

The Trailblazers Experience:

Do you think, rosie, it's a thing that women do a lot? Because when I speak to guys, they automatically would have just singing. From my lived experience of men who are doing really well and are just go-getters and have achieved so much They'll be like oh yeah, for that role I went in, or that position, or that contract, I went in at this top number and then we came back to this, whereas a lot of women who I've spoken to would have actually started at that lower end. Do you think there's a lot of that in there?

Rosie Bailey :

It's completely related to your conflict aversion and you can get a personality test on this and I actually was personality profiled and highly, highly conflict averse I'm. I'm an extremely classic british cultural person and the way a culture, a conflict averse person will operate, especially a confident, ambitious, conflict averse person in a leadership role is they in their head and I can see myself doing this all the time will be thinking, well, that's not the best way of doing it, or it's gonna take you longer or it's gonna be a bit more expensive. But because it's gonna be conflict to try and persuade you to do it a different way and because you'll get to the right answer in the end, I go okay. But one time you suggest something which I'm sure is going to fail, so I go no, we're not doing that. That's so interesting. So I avoid the conflict, avoid the conflict, avoid the conflict. And then suddenly you reach my red line with no warning at all and I go, no, we have to do it a different way.

Rosie Bailey :

And those are the people that really struggle because they go into the negotiation going I don't want to fight, I just want the right answer. The right answer is somewhere between 82 and 85. So if I go in at 87, I give to 85 and we'll all be done. Just get it out the way. Just let's get it out the way.

Rosie Bailey :

Let's not fight too long blah, blah, blah. And the trouble is is, if you reach somebody who doesn't care right and conflict doesn't have to be hatred, do you know what I mean but they don't mind about getting your back up, upsetting you, making you feel bad, making you feel uncomfortable, making you sit there and sweat for two days, all of these things that you are terrified of doing. So they go. Well, I'll come back to you. Or 70? No, well, it's 70.

Rosie Bailey :

You're clearly because of blah, blah, blah, blah, lots of reasons. And you're like no, it's not, it's. I said it was 87, I'm still. You've run out of road, haven't you? Because you haven't embraced that back and forth.

Rosie Bailey :

And so I think and this I hate talking about men and women, because people are different, but traits we associate with lots of women is to do with building consensus. It's not true for all women, but it is often true. And so if you know that you love building consensus, you hate conflict, you hate the back and forth. You're the person who needs to persuade yourself to to go in more aggressive than you thought you were going to be. If you think you're the person who really embraces the conflict, you know the right answer. You're going to be arguing 100, whatever. You've got to bear in mind that you might break the whole conversation. Do you sort of mean, like by standing there at 100 thinking they're going to come to 72, I'm going to go to 95, they're going to come to this and they, they just walk. That's your risk if you're that person. So you know you've got to match.

The Trailblazers Experience:

Yeah, and I think the reason why I bring the differences look, men and women are different, but they're also the fact that we can learn so much from the other gender. They can also learn so much from us. But anything that can help us get ahead, I mean, why not take those things? So I love the fact that you've said it's two things. So be prepared, do your research, play it out, you know, role play beforehand, anticipate exactly, and then the going first is a really good one, because you are sort of in the lead, and then it's them counteracting everything that is going on you own the conversation then.

The Trailblazers Experience:

Yeah, for sure, for sure. And that's in anything, especially if you're building a business and you're having to go in and ask for investment or get people to start using your product, your tool. It's a skill that you will carry for life. So I might do that personality test actually to see.

Rosie Bailey :

Yeah, I, can't remember what it was. I had one for work, but you know they're established like Myers-Briggs. Yeah.

The Trailblazers Experience:

Yeah, that's really interesting. So what is your vision for Nibble? Where do you see it evolving? We obviously know that AI is a very big part of what businesses are looking to adopt. There was an MIT research that did some insights. I think they surveyed around 600 CIOs, so chief information officers, chief technology officers and they were talking about how data analytics and AI infrastructure what they're looking for. A lot of people is about what's scalable, what can be governed, what is future-proof, and then there are things about talking about what's open source, what's you know it's auditable, I think, as well.

The Trailblazers Experience:

Exactly. That's a really big thing. But also what will add value to the business. Where you know before, when you had a business and you're growing it and people would say, well, what's the value of the business? They look at your profitability and they say, well, 5x it or 10x it. Now it's what technology is there that is proprietary that we can actually use? That's actually what will add more value. So where do you see Nibble going from, where you started, what the original idea was, and it might still be the same, but that's the direction you're going as to where you think it's going to evolve in the next few years.

Rosie Bailey :

So I think I think what chat GPT has done for us is made everyone realize that you can use AI technology in many, many different ways that you didn't realize that you could before, and sometimes it causes you to go back to artificial intelligence technology that's been around for 15 years. But I think it's made everybody think how do I do this, how do I use this, how do I keep my business going forward, which I think is really important how do I keep my business going forward, which I think is really important. So then you say where did I automate something or digitize something? But stop because the technology couldn't do it.

Rosie Bailey :

And so, before we digitize things that were very certain processes, think of anything that could be created in an old fashioned flow diagram. Do you remember where the box is the action and the triangle is the decision? And the box is the action and the triangle is the decision? Right, and I think that can be done, like that can be digitized. But now those decision points, those triangle boxes, can take much more complex decisions.

Rosie Bailey :

So previously you had to arrange all the data really carefully for people to say, and they would just say is this customer bigger than 500 people or not?

Rosie Bailey :

Yes, go to the sales team, no, ask them to use the self-serve portal, something like that. But now actually we can do much more detailed and thoughtful exchanges, because there's just a greater level of, if you like, understanding, thoughtful exchanges, because there's just a greater level of, if you like, understanding an llm piece of technology can understand with greater, um, uh, greater, more unstructured information. Do you sort of mean you don't have to put everything into a database? Now it could read what the customer's email said and said I believe this email is looking for a return or looking for an alternative product recommendation or looking for and actually you can read that sort of unstructured data in a way you would normally have had to have a human in the loop to say this email needs to go to this department, this email needs to go to this department. So you're already seeing this in sort of that sort of use case is the LLM is sitting at the inbox and without anybody reading that inbox is then directing it to the right next inbox.

The Trailblazers Experience:

It's amazing and for those who don't know what an LLM is, it's a learning language model. Basically that sits behind all the AI technology. I mean, it's just it's taking away the, like you said. Cutting to the chase is sort of the terminology that I use to help the decision making.

Rosie Bailey :

And so when you think about the amount of money people large enterprises spend on people and the amount of money large enterprises spend on software, it's still 90-10, 90% people, 10% software, whereas actually you're getting to the stage now when some of those people, I'm afraid I do strongly believe will be replaced by computer programs. Now I suspect what it'll be is, for each individual it'll be 50% of their job, so they'll get re-skilled to something else. So I'm not trying to predict Armageddon It'll happen more slowly and more normally than that but the parts of their job that were repetitive, or checking things, that will be given to an agent. And so what we're seeing is, let's say, you're in a B2B sales process and you have a team of salespeople. What we're seeing now is them saying oh well, for these smaller clients, I would like to use something like Nibble to negotiate a price for the smaller clients because, as long as it's in this range, it's more cost effective for me to negotiate via nibble than it is for me to put a salesperson on it when I want the salesperson to be chasing this massive account or this new account or, frankly, taking someone out on the golf course, which nibble can't do and I don't believe there's an ai agent that could do that yet, because there are things that that that salesperson is really good at and only human can do, and actually there's things they can't. And we've all thought about putting your expenses in or booking your travel, but now you can think about negotiating a price or negotiating a basic contract.

Rosie Bailey :

I was talking to one person in procurement and they said that their business needed to procure agricultural products that have a traded price, because if the harvest is bad, the price goes up, and if the harvest is good, the price goes up, and if the harvest is good, the price goes down. And so it was the job of senior management to make sure that they always had a steady supply. For a risk management perspective, this is a strategic imperative that they're always able to get milk. But there's also a risk of financial cost as well, because if you always just buy the same amount of milk every quarter, then you risk going with the flow. So if you see the price drop, there is a scenario whereby you go to your existing supplier on existing terms and just look to upsize your order by 20%. But you don't want to upsize your order by 20% and just take the market price, because you may as well just keep your normal ordering pattern.

Rosie Bailey :

But, if you could upsize your order and get a small discount, why not? And so she was saying that why wouldn't you use Nibble for that kind of thing, where you send somebody an email and say, I've noticed the market price is good? If we can agree something in the next couple of hours, I can probably upsize my order, and if we can't, don't worry, we'll keep to the same pattern as we always do. Because she said that's the kind of thing that she didn't have a big enough team to ask someone to go and do that for two hours, and so she didn't have the resources to do it. So it was like always a pipe dream, a nice idea, but not something that happened.

The Trailblazers Experience:

Yeah, it's thinking about the problems that you can solve now and that's a really good example that you've just given about what's actually happening that impacts the teams and what would take extra resource to actually do these negotiations. And if you have a tool I mean to be fair, I'd rather receive an email that's helping me negotiate something and I can have that back and forth right there and then and come to a conclusion and happy days versus a phone call, a meeting. Oh, let's get together, let's speak to just.

Rosie Bailey :

you know, it just makes it so much easier yes, and then the more complicated things, or the new customer who doesn't know you, or the, the um, the, the insurance contract on your headquarter building that's 25 stories high.

The Trailblazers Experience:

You know like there are some things that it makes sense to to be in every detail yeah, how does um so your core values and ethics come into the ethical considerations when developing ai technologies for negotiations, especially with your business? What are the, the key things that are really important for you as as a founder, as a ceo, with with your business?

Rosie Bailey :

So actually, funnily enough, this is a really proud moment because we started using OpenAI's API a little while ago and my CTO said to me. He said we need a sort of global prompt for the OpenAI that says in all of the answers you provide to us, please make sure. And we sat down as a team we're a small team all around the table and we whiteboarded it out in about 20 minutes. And so it starts with never be racist, for example, sort of core values, that. And actually you don't need those ones because mostly the API has those ones, because for most people there's there's laws actually associated with that.

Rosie Bailey :

But but then it gets down to always be friendly, always be concise, always be. And you start writing, if you like, your cultural values down in a way that you almost like, like this chat gpt is going to be a part of your team now. So you need to brief chat gpt on how to, how to speak, do you know to me? And always be concise. And then somebody not me said because I've been saying it for a long time never be gendered, because I have a personal soapbox that a lot of ai assistants are female and subservient and I get.

The Trailblazers Experience:

There's a lot of unconscious bias, isn't it?

Rosie Bailey :

I get, I get very cross about this one.

The Trailblazers Experience:

Yeah, no.

Rosie Bailey :

So I've always been very clear that nibble is it, and not even they. To be perfectly honest, it's a machine.

Rosie Bailey :

Yeah, don't give it more credit than it, then naturally it's due. Yeah, but then, interestingly enough, then the corollary of that is nibble will not gender you if it can avoid it or unless invited. So it's a nibble will sort of default today if it needs to find a pronoun and it's not completely clear that you want a particular pronoun. Do you see what I mean? And this is I have some personal background that I've learned about this from a family scenario and I'm embracing it. I'm, I don't, I'm not perfect, you know what I mean, but but I'm like oh, okay, all right, like we should do this, this is easy win right to make people feel comfortable.

The Trailblazers Experience:

You don't also want when, when someone's using the, the negotiation tool for the negotiation, to fall down on these basics, isn't it say what exactly? Well?

Rosie Bailey :

how? Why did you make an assumption? We don't ask for your name. Some people give their name, but but many people, most people, don't. We don't want your name because we don't want to accidentally give the AI information that may cause it to make decisions that we don't want it to make. So we don't give the AI any information about you on purpose because we don't want it to use that information, and so we do our very best to avoid giving. There are some things about the way you write that kind of thing that inevitably go in, so then you have to manage that other ways by being specific about the responses that come back out. But on the whole, we give the LLM as little personal data as we can get away with. Certainly not your name, certainly not anything demographic information or anything obvious, right?

The Trailblazers Experience:

Your racial background or your age. That exercise really helped pull together the businesses.

Rosie Bailey :

Yeah, you know, but it was so quick as well, values, yeah, and it was so quick and it was so like well, we always do this, but now we need to write it down and I thought that was rather wonderful. So I think it's a really good exercise. And if anyone listening has a team and is wondering how to write down their AI ethics policy, sometimes that kind of gets a bit long winded and impractical. People now use chat gpt, and I'm familiar with that. If you were to prompt chat gpt, what would you always need the prompts to do, regardless of the use case or regardless of the person using it, or you know, and and that I found a much easier way to picture what the rules are. The other one, which is going to come into law in europe is uh, never pretend to be a human.

The Trailblazers Experience:

I think that's a good one as well.

Rosie Bailey :

And seek to clarify that you are not human if there seems to be a misunderstanding.

The Trailblazers Experience:

Yeah, there are lots of. Even when you're creating podcasts, now there is a tick box to say can you validate or confirm that no AI was in terms of impersonating a human, et cetera, etc. That it was literally you and I the ones having this conversation, so people can understand. And you just think, oh my God, there's going to be more and more tick boxes before you can actually post a podcast.

The Trailblazers Experience:

Because there is the danger that it is AI generated and it's just spewing all kinds of nonsense onto the internet as well. So it's exciting. It's an exciting space, I believe. One question which I always ask my guests is and I'm actually thinking differently about it I used to ask you know, how do you? What does work-life balance mean to you? Is there even such a thing as balance? What does work-life balance mean to you? Is there even such a thing as balance?

The Trailblazers Experience:

And asking that question was really selfish because when I was building my career, I also had two children. So I spent a lot of money on childcare, au pairs, nannies, all of it because I knew it was a means to an end, but also it was. There were also decisions I had to make that I knew I was giving up not being able to go to every play because I was on a plane, negotiating, launching with some new marketplace or opening stores, and I came to terms with that myself because it just meant I was not beating myself up. But also I know I will probably miss one meeting or one conference because I've decided I want to go to the play that my kid actually has a role in. But it was the non-negotiables for me that I made and also I made sure that no one could put me down at the school gate because I just arrived on a flight from a business deal that I did.

The Trailblazers Experience:

That question came about why I'm asking all the women about work-life balances. Does balance even exist? And I'm coming to think, rosie, actually balance is what you make it to be that works for you in your life. Have you found that now, as a CEO of a startup, which means it's all hands on deck you have a small team, but it's still all hands on deck lots of traveling have you come up with your non-negotiables as well for yourself?

Rosie Bailey :

It's in your choice of life partner? Probably yes that does help and with that goes, if you like a team, you know who's your team, who's your personal team, and I think this is the most important thing and the people I know, the friends I have who complain that they haven't hit it right, they haven't built the right team.

Rosie Bailey :

And it often starts with your life partner, and I know not everybody is in a two parent relationship or a 2.4 children, so it's not true for everybody. But you need a support team and you need to know exactly who they are, and you need to not be always picking up the pieces that you don't want to pick up, for If you hate doing the cleaning, you need to worry of not doing the cleaning, and you either need to find the budget for a cleaner or you need to tell the other people that you live with in your house that chores are allocated as follows.

Rosie Bailey :

You know, and that's the thing that I slightly get frustrated, because I do see a lot of women taking a huge mental load and not seeking resolution for these really silly basic problems you should be worrying about do I care about the school play or not? And I think my decisions probably echo yours a little bit. I go to some, I don't go to all, and I'm happy with that and I'm fine with that. And those are the really important things that you need to work out for yourself. But the unimportant things as you did the dishes and takes the bins out, it's really not important. It has to get done in mundane, yeah, but it's so mundane.

Rosie Bailey :

And actually, to be fair, coming from a very non-conflict person, I'm not in, a, fact I'm. I don't talk very much, I'm not a let's talk this through but I can tell you those are the only things we've talked about in our family, you know, like those are the only things that I've actually really bothered to kind of go. I don't like the way that, just because I work from home, you come home and I've made dinner and then he goes. I don't expect you to make dinner and I'm like good point, so why don't you just not make dinner? And when I get home late, we'll work it out. We'll either make dinner or get takeaway.

The Trailblazers Experience:

I think that's it, isn't it.

Rosie Bailey :

And he's like I do not expect you to be wifey at home just because you're working from home. I'm like, good point, I'm not Like the next three days there's no dinner. And then you open the fridge and it's empty and I'm like, yeah, I'm living the dream, and then we sort it out.

The Trailblazers Experience:

Do you know what I mean? It's being unapologetic about the choices that you're making and the life that you want to live, letting go of the choices that you're making and the life that you want to live letting go of the things that don't matter and just making it work. So it's that support system, whether it's in your home, if you have that, or external factors, or if you have to pay to have some sort of support system and also that team.

Rosie Bailey :

And the other thing I would say is this often hits when you have a family. It's not the only scenario.

Rosie Bailey :

Sometimes you have caring responsibilities of other different, and the other thing to bear in mind is your career will outlive whatever responsibilities it's causing the crunch, be it primary school age kids or elderly parents or whatever it happens to be, or health issue or whatever. You need to get through that period, which may be for many people like my guess is about 10 years, so it's not short, but your career will outlive it, and so what you don't want to do is kiss goodbye to all of the things that you love about being yourself, whether it's exercise or having a great job, or you've got to somehow cling on to enough of it that you can expand at the other end. Yeah, and for many people, they say oh well, I'm giving up my job because if I get child care, it it doesn't balance out. Do you know what I mean? Like my child care costs are the same as my income and you're like yes, but it keeps you current and it keeps you in the work keeps you in the loop.

Rosie Bailey :

Yeah, so don't look at it as a yeah you feel really weird to frankly not take home any net pay for that period, but actually it keeps your head in the game.

The Trailblazers Experience:

It keeps you in the game. It keeps you growing.

Rosie Bailey :

You've got to take a longer term view on some of these things, which is hard. When it's 10 years, it's really hard and I think that's it.

The Trailblazers Experience:

The problem is now we live in a culture where, whether it's whatever social media platform, we are being shown all the successes, but what we're not being shown is actually the sacrifices, how long it took, what led to that stage, and you would hope that's what actually people should gravitate towards, which is why I love this podcast, because people just tell it like it is. You can listen to it and take a few tips and say, okay, I'm in this stage of my life, this is what I'm going to implement. Or actually, this doesn't relate to me. I'll fast forward to the CEO leadership stuff. Or actually, I'm in my 20s and I just need to enjoy focusing on one thing. So that's the great, great stuff about it.

The Trailblazers Experience:

Yeah, yeah. Last but not least, I always ask our podcast guest to leave three trailblazer takeaway tips, and it's things you wish you could have told your younger self, things that you've learned over the years. Just to give a bit of a guide to someone who's maybe fast forwarded to the end of the podcast and said I just want to know the top tips. What would they be, rosie?

Rosie Bailey :

Okay, top tips. I think I've already said, but I'm going to make it my top tip learn your elevator pitch and do not be shy about it and always have it ready, whatever it is, and make it optimistic. Um so, elevator pitch, top tip number one, and alongside that is like don't be afraid to do sales. Don't be afraid to do sales, sales, sales for yourself, sales for your business, sales for your ambitions. Top tip number two is negotiate, and don't be afraid to negotiate. Don't be afraid to embrace negotiation and if it takes reading a few boring articles on the internet, there's a lot of academic research in negotiation. But don't be afraid to negotiate because it's cool, it builds relationships and you don't need to. You can do it and be yourself. So my second top tip is negotiate. My third top tip is AI.

Rosie Bailey :

The world is moving very, very quickly and I remember when ChatGPT came out. My parents are both ex-engineers, they're both smart people. I went home and they're in their eighties and said oh, have you heard of chat GPT? And they both said to me I've read a headline about it. But, darling, you know, it's not for us and we don't need to stay current at our age. And I said actually on this one. It's quite a big step change in things. I think it's quite interesting. I think it's worth you reading a few headlines. And I went home two weeks later and my father's like oh, I've read this and I've done this, and I've done this, and and and I.

Rosie Bailey :

I do think if you're sitting there reading all these things and saying what is chat, gpt, what are llms? You know what is image? Generation is mid journey a thing? They're all very accessible. Most of them have free plans, and I think there is no way of learning about what's happening in the world except by experimenting for your own, and thinking is stupid if that's what you want to do. Do you know what I mean? Like I started by using it for certain things and thought well, I'm better at it than this, than the machine, which is quite gratifying, to be honest. But I think experiment and don't be afraid to play around with it or ask other people what they're doing with it and make up your own mind. It's much more accessible than any wave of technology that's come since web pages became a thing in my life, josie thank you so much for sharing your incredible journey and invaluable insights with us.

The Trailblazers Experience:

Your story is inspiring because I do know a lot of young people who are always interested in finance, banking, etc. But the fact that you've done that and then now you've moved on, transitioning to technology, it just shows that you can never stop learning and your career is a journey, isn't it? There will be lots of highs, lows, transitions, inflection points, and it's just about embracing that, so your story has been really inspiring. I'm sure our listeners have gained a lot from the conversation.

Rosie Bailey :

Thank you so much, but who's going to interview you for your inspiring story?

The Trailblazers Experience:

Do you know? That is really interesting. I need to actually have that. You need to do that, yeah, and I think about what, what, which story will I tell? I feel like Exactly.

Rosie Bailey :

Exactly, and thank you so much. It's been such an honor.

The Trailblazers Experience:

Awesome Right For our audience. This has been the Trailblazers Experience Podcast and until next time, see you soon. Remember to follow, like, subscribe, share and tell another woman about the podcast.