In this episode we discuss: When it is the right time to quit. We are joined by Eleena Broadfoot, Advisor and Executive Coach. 

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We chat about the following with Eleena Broadfoot: 

• What are the important factors to consider when deciding to leave a job.
• Adding value to the business and making a meaningful impact should be a priority.
• Leaving a job requires careful planning and consideration of personal and professional factors.
• Why is identity so closely tied to job titles?
• What is a good time to reassess your learning and value-add opportunities in a high-growth company?
• How to leave a positive legacy for the team. 
• Be curious and open to new opportunities, and have conversations with recruiters and friends in different industries to explore potential career paths.

References: 

• linkedin.com/in/eleena-broadfoot

Biography: 

Most recently CFO at Beauty Pie, Eleena has over 20 years’ experience in senior finance roles at Virgin, Trainline & Funding Circle amongst others, working alongside leadership teams of both high-growth startups and global groups. Her experience of working with founders and their teams as a CFO and NED has provided her with some fantastic opportunities to reach beyond the traditional finance remit and enabled her to use her skills and knowledge to create value and deliver strategic insight to help drive growth.

To learn more about Beth and Brandon or to find out about sponsorship opportunities click here. 

Summary:

00:00 Introduction

28:29 Welcoming Alina Broadfoot

29:50 Lessons Learned

32:26 Deciding When to Leave a Job

34:37 The Tipping Point: Leaving Virgin for Train Line

34:59 Navigating Job Titles and Social Expectations

37:33 The Right Time to Leave a VC-Backed Company

41:55 Leaving a Positive Legacy and Smooth Transition

42:47 Embracing Curiosity and Exploring New Opportunities

Unknown Speaker 0:00

Music.

Brandon 0:06

Hello everyone, and welcome to another episode of the operations room, a podcast for coos. I am Brandon mensinger, joined by my lovely co host, Bethany Ayers, how are things going? Bethany, they're

Bethany Ayers 0:15

going better this week than last. I had yet another cold. I'm just so tired of being ill, but otherwise it was fine. I finally have some energy back. So I have some news, as I've shared on the podcast before, I was going for the CEO role, and we didn't know what was going to happen. And then, if I just wasn't going to get the job, I was going to have a gap year,

Brandon 0:38

gap year, yes, just like a 22 year old, exactly.

Bethany Ayers 0:41

And so started being very excited by the role. Then it just kind of dragged on. And then I had my gap year idea, and so then I was a bit more relaxed about it. And last week, found out that I was, I can't remember what the term is not going to proceed with me. And I said, Oh, gonna proceed with the other candidate? No, gonna proceed with the three new ones? No, they are proceeding with nobody.

Speaker 1 1:12

Oh, wow. They've pulled the rug on everyone, everyone.

Bethany Ayers 1:15

Brandon 1:39

on. So let's back up a couple of seconds here. So you told me earlier that this one you were actually interested in, so you're not bothered by the fact that they've pulled the carpet.

Bethany Ayers 1:46

I think part of it was that I've had to have my gap year idea, and another part was when we spoke about this before, I was really missing being consumed by something and caring and thinking. And in the meantime, I've created this course on wow the board and supercharge your career off the back of the free sessions I'm giving, and it's consuming my brain, and I'm interested, and I'm thinking and I'm learning. And so then suddenly the CEO role seemed like a bit of a distraction and a departure from something that's starting to be interesting, that's unfolding.

Brandon 2:20

Okay, that makes sense. So, yeah, it's nice to have a rekindling of interest in something that sounds like you have, which is great, and, I guess, slightly fascinating, slightly disturbed. At the same time, when companies decide to use an executive recruiter, pay a lot of money for that in terms of retainer, put forward a bunch of candidates, waste a bunch of time. In this particular case, did you get any feedback as to what the scenario was? So

Bethany Ayers 2:43

I got very little feedback. And it's not that they have decided to close the role or they're going to postpone recruiting, they're just going back to the drawing board and are taking as long as it takes to find the right candidate. So that is my bigger news, whether or not I'm going to do my gap year. I still, I think I am, because we've had no summer, and the idea of December right now just makes me cry. It's just been so cold and wet and miserable, and I'm just thinking, Oh, December, you add darkness into it. I just don't wanna.

Brandon 3:25

So we have got an amazing topic today, which is how to figure out when it's time to quit. And we have an amazing guest for this, and Alina Broadfoot. She's the Chief Financial Officer for beauty pie and is a Ned as well as an executive coach. So before we get to Elena, I wanted to ask you a couple things Bethany. The first one was Alina had talked about this idea of financial anxiety, and that that's actually driven her quite far in her career, and that she's at a point in her life now where she's no longer driven by that, and she now has some level of optionality and the more flexibility to kind of do what she wants. How do you manage financial anxiety is the question.

Bethany Ayers 4:02

I mean, I have, I have spent so much time thinking about this and wandering through this in the last almost 18 months, and probably before that, and when I was making the decision to leave peak. Because I think financial anxiety, money means so many things to us. That is not money. Money means security, money means freedom, money means love, money means status. And so part of it is to figure out why money means a lot to you and what is real. And so for me, money means security, money means love in being able to provide for my children. And for a very long time, money didn't mean status for me so much as like winning slash a star, a plus behavior, I am a top performer, and therefore I should earn my potential, and if I don't earn to my. Potential I am wasting. My potential is like a real story going on in my head for quite a long time, and so it's been unpicking all of that and realizing what do I actually need and why and what to prioritize in life. I still go back and forth like I have done things like, look at all of my savings and calculated if I wanted to spend however much a year I want to spend, how many years do I have in savings? And that has helped calm me down somewhat, because I'm looking at reality. And then there was a time where I felt like it was my duty to create generational wealth so that my children could be absolutely fine. It's like, I have the ability of creating generational wealth, and therefore I should. And I actually talked to the kids about it, and it was a few years ago, and my kids just, I mean, partially they don't understand, but partially my son, my at that point, five foot three son was like, Don't worry, I'm going to get drafted into the MBA, and then I'll take care of you. You don't need to look after me. I will look after you. And my other son is like, I'm going to be a YouTuber and I'm going to be very

Brandon 6:14

famous. Instead of being an actor and a musician these days, it's being an influencer slash YouTuber

Bethany Ayers 6:19

100% and basically, I don't need you to look after me. I want to look after you. And it took a while for me to actually hear what they were saying and realize that creating generational wealth, although it sounds amazing, takes a huge amount of agency and purpose away from your children. Some of the most unhappy people I know are people that don't have to work, and never had to work, and they've come from a lot of money, and they don't know how to handle it, and they don't have an identity, and they're trying to be good people, but they don't really understand, and they don't have any purpose. Yeah, they don't get it, and they're kind of like wandering around trying to find purpose, and sometimes people do, but there seems to be, ironically, harder, at least from my experience, of people who come from serious money than people who come from comfortable backgrounds. So I have stopped worrying about how much we're going to leave the children and how to put them into the best position possible, and that's been very freeing. And so I could just look at reality and know that we're going to have enough and we can't take it with us. And then also, one of my children is adamant he's not having any grandchildren, and the other one isn't sure. So like, there could very likely be no need for anything come another generation. And so what? How do you feel? Because you've had to deal with this as well.

Brandon 7:46

I go through phases of feeling really good about things and good about my fortunes, not fortunes in terms of money, but just my fortunes in terms of life and circumstance, you know. And I've been very lucky, I think, to be in a position where I've been able to earn what I've been able to earn. But equally, I've gone through phases of panic as well, where I recognize that sometimes we're overspending. I feel like, in particular, the last year and a half with more of this consulting fractional piece, the anxiety is more ever present, I would say, simply because I think as a male, for better or worse, it's very much ingrained into me, in the sense that I feel like I have to be a provider, like that's one of my roles, and as a provider, if I'm not providing or providing in a substantial way, or that's strong enough, it's very personal, I guess, in terms of affecting me and feeling like I'm not doing what I need to be doing at a very basic level for the family. And I think the other reflection, at least for me personally, is that if I go back into where I came from, I came from not money where we're renting throughout my existence as a young person, living from house to house, sometimes having food, sometimes not. For the most part, we had like electricity, but occasionally was cut for a variety of reasons this type of scenario. So I think when you graduate from high school and you graduate from university with that thing in your mind around finances being very real, and it affecting the family in quite traumatic ways. It drives you, and I think ambition, drive, focus. A lot of it came from my upbringing, but I think my pure ambition and drive has helped me to get to to where I'm at, recognizing that financial security matters, being a provider matters, and it's kind of got me to where I've got to I guess that being said, I also recognize financial anxiety is like not a desirable state to to be in. So to be able to get past it at some point would be a great position to be in. Well, thank

Bethany Ayers 9:33

you for sharing, because I learned more about you now than I think we have in the first 49 episodes. You

Brandon 9:41

know, one of the thing I would tell young people, as well, and I think I've only recognized that as I've gotten older, is that when you're in your 20s, you graduate, you make very little in terms of your employment and your income. That's just the way it works. In your 30s, you're starting to get to more of a middle management position, but you're still making chump change effect. Actively, and I think it's only once you hit the 40s where properly, you're starting to become an executive in companies, where suddenly your income and your compensation starts to skyrocket. And it happens kind of at the right time, because, you know, you need to get a house, you have a family, this that the other so it comes in handy at that point. But I don't think you realize the magnitude of the difference between your income level when you're 20 and 30 versus 40 and onward, it goes

up dramatically, as do your outgoings. And that's the part that always just kind of confuses me a bit. But going back to what you're saying about as a man, being a provider, I definitely would not be able to be in the position that I'm in now. Were we not a double income family? I really do feel for men who don't have wives who work, because it's a huge amount of pressure to be on one set of shoulders and not on two sets of shoulders, like it's not, oh, having a wife who chooses not to work, and could, like, go and suddenly earn the same income, but you have somebody who just doesn't have that same earning power if the family ends up in a bad situation. And so I do. I'm very grateful for the fact that we are both high earners. It has been incredibly difficult, and we've needed to have nannies, and we've needed to have support to do it all, but it makes it a lot less pressure on either of us. It's

hard for me to imagine growing up now with the circumstances that we have, because it feels like it's almost like a necessity to have two solid incomes in the household, to prosper, to be able to buy a home. So to your point, I think it feels like it's less of a an option these days, as opposed to anything Elena talked about being institutionalized at Virgin having been there for over a decade and really lacking the confidence to see that she could be effective elsewhere. How do you give yourself confidence that you have value, you have skills, they aren't tied to one company, and that there's a whole range of possibilities out there? How do you give somebody confidence where they feel like they can actually take their skill sets, take their value and go elsewhere and not feel like they're somehow tied to the company that they work for.

So I think I have two answers to this, the pre the world ending, financial crash, whatever we're dealing with now, and the post in the new world, in the pre world. I'm giving this advice still, because hopefully at some point we'll get to some sort of we'll get out of the doldrums that we're in now. Is to just leave your job and leave that world that is knocking you down so much. My experience and I've had this in different ways, work and personal is how much we create and give meaning to the world that we're in and how small that world is. And so in the work environment, the people there are very real to you everything that's happened every time that you're knocked down or supported reinforces that this is all of the worlds must be like this one, because this is the one that you're experiencing every day, and yet when you leave it, at least when I've left it within a week, two weeks, those pressures, those stresses, those people, those dynamics, those politics, those criticisms, those praises, are utterly irrelevant. I'll have people get in touch with me and try and share office gossip, and it's wildly interesting, but nothing like it was two weeks before. And so quickly you can rebuild your self into the new world and create new worlds, and find your inner confidence. I wouldn't suggest in the current market to just quit, because, as we discussed before, it's a pretty tough market. But I would take that learning of making your world bigger and having your current job mean less. Do that in other ways. So one just become aware of the fact that you're making your making your job mean so much more, and creating your self esteem and your identity around it. And then secondly, mentoring other people in other companies is one of the best ways of going, Oh, these people know nothing. I know something. And just getting out there and talking to and learning about other companies and other people, doing some volunteering, making your world bigger, you will already find the areas where you have confidence to then face going into a new job or staying in your job, but feeling a lot better about yourself while you're

there. I think having peers around you in some form, around communities of interest to you, to expose you to other possibilities, other work environments, whether it's mentors or networking or communities or what have you. I think just that expansion of your world is so incredibly important to make you realize what you have and what you don't have and what is possible that is out there. For you.

And I think basically you've just teed it up perfectly to support our sponsor and the CLO round table as an opportunity.

Yeah, I guess the other thing that I think about is, I think scale ups, for better or worse, is good for this, because there's a forcing function that happens at scale up so you don't necessarily get in bigger corporate companies where companies where you can work for a version for 1015, years and not even think about it, whereas at a scale up, they're designed to not live that long, or your existence is not designed to last that long. So whether you like it or you don't like it, it kind of doesn't matter. You'll be forced, within some duration period to leave that organization, whether it's by choice or not. Just having that versatility of experiences is huge, although

you can still lose your confidence towards the end of it, yeah, or at least I have. So

the core question here is, what have you learned along the way about when it's time to leave? What are the markers for you in terms of when to leave.

So this comes back to the conversation around vesting periods versus natural periods to leave, and whether or not you're still providing value and still have that energy. And I suspect that I have stayed too long at businesses being tied into vesting rather than the value I was still adding, good execs, good hires, seemed to add a tremendous amount of value in the first 18 months to two years, lots of energy, lots of clarity. Can see where you need to go. And I guess this is mostly me speaking, rather than looking at peers. The next two years is a bit of like my previous reputation, respect following me, but the energy, the interest, the drive, the clarity of thought, steadily declines. And then also, from that very first, one of the first episodes we had with Kristen Shannon was about when you have to start undoing the processes that you've built, and it's really hard to undo the processes that you've built, and

you're like, I love them. They work so well. They

work so well. And not to take it personally, like, because, you know, I'm a bit of a perfectionist, and making a mistake is a big deal for me, and so I perceive needing to change processes as I did it wrong in the first place. And it takes a while for me to get to the point of, no, I did it right, but we are now twice the size, and therefore we need a different process. And so I start to take everything quite personally, and get stressed and beat myself up about not being capable. And that probably happens two and a half, three years in, and then the last couple years is just me clinging on.

Yeah, yeah. You know, I thought about this more recently, because I always had the impression somehow that longer durations, which I've had in the past four years, five years, six years, have been a really good thing, generally speaking, both for me and for the organization. But I think just reflecting what you said, I think there's a real, realness to it, which is, I think the first two years as an executive, you are there with a passion and a mission to make some stuff happen. And you can feel it within yourself. There's super engagement, and and you're like, I'm going to take this kind of shit show that I'm being handed right now and make and transform this into something spectacular. And once you get to that two year mark, you've done a lot of stuff, and that next two year period, I think you're right. I think your engagement is less because of what you set in motion at that point. We

have interviewed people. We have somebody coming up who lasted a very long period, and I think those are people who are able to continue to find the energy for the new challenge and find the new challenge. It's just not something that I've been able to find after a couple of years. Think

it's almost like being kicked in the ass to realize that you have to find the next challenge. I

think you need to create an environment in which people can work together to see the next challenges, rather than it being all on one person's shoulders. Because after you've come in as an exec for that first couple years, loads of experience, it's really obvious what needs to get done. And you do those things, then it's hard, because, to my earlier point, you've become part of the world that you're in, and now you can't see out of that world the other possibilities. And I think that businesses should think about, maybe the ones that are successful, where people last many years have created the environment where you can come together and all work on seeing the future together and then reinvigorating what needs to get done next, rather than it being you by yourself. And it goes to the Rumsfeld, knowing what you don't know, knowing what you know, knowing you know. So I think there's a lot of the don't know what you don't know, elements that you need to somehow. All in as well, because otherwise you just get a lot of group think,

yeah, about what you've done and the past to some extent. So what is the right way to leave an organization?

Professionally? Don't burn bridges. Be magnanimous. Work on having successors, or if it's somebody who's coming from externally to replace you, protect your people and explain who's good and why, but be balanced about it, proper handovers, and really make it clear that you've not lost faith in the company, that this is a decision for you, for the future, not a reaction to something that's happening in the

company. And why does that matter? What you just said? Because

I'm assuming that people who are listening are C level, the CEO is the main, most important person. But then after that, the COO is next, and people love a bit of gossip. People love drama. No matter how well the company is doing, people will see your departure as something exciting and salacious and dramatic, and the gossip will happen. And so to keep that gossip as minimal as possible, and people focused on the mission, it's important to not feed it, because

at the end of the day, as a CEO of the company, it is extremely important for your career progression to have really strong relationships and referrals that are backing you. Because at the end of the day, whether it's referrals that you're providing for your next employer to your current employer, or whether it's them doing back channels on you, which they end up doing for the most part, you want to make sure that you have really good, strong word of mouth around you and not burn bridges to your point. And irrespective of what's happened in your career to your companies, for good, for bad, for ugly, it doesn't matter to your point. You need to be magnanimous. You need to make sure those relationships are as strong as they possibly can be and to make sure that your word of mouth referral network, both known and unknown, is rock solid, it matters so much, especially as you get more senior, I think if you're more of an individual contributor, you can get away with a bit of burning of bridges to some extent. But once you become a senior executive, any burn bridge will come back to haunt you in some ways. And I know that I've done referrals for others where they have burned bridges, and I have not been shy about expressing that to the person that's having a call with me. So it matters, and having a wonderful relationship matters. And being a part of the company comms to ensure that there is no salacious inferences around why your departing matters as well. I think

if you're an individual contributor, it's never too early to not burn bridges and to learn that skill. And I have had people phone me for back channel references for individual contributors up to 10 years, 15 years since I've worked with them last, and I have been able to say it has been a very long time. I'm sure they've changed a lot in the time, but this was my perception 15 years ago. So just be professional from the start. It's good practice. And you never know when those relationships are going to come back and matter.

Yes, they will come back in weird and wonderful ways. All right, last question, this is my favorite question, which is, is a successful career? Just about being lucky?

I think there's a lot of that I love that you've asked this well. I mean, if you take it really far back that we were lucky to be born where we were, we are lucky to be born white. We're lucky to have been educated, you know, all of these things. Yes, there's a huge amount of luck, even just in how we were born. I mean, the fact that you're born able bodied white man, and you did share your story of not growing up with loads of money, but you still grew up in Canada, where you had access to a great education, regardless. So on that really like macro level, luck plays a huge amount. And then I used to feel like luck was a massive part of my career, all of it, and I didn't take a lot of responsibility. And I always hate the question that I get of, how did you get to where you are? Or, how can I make my career like your career? And I hate the question, because I don't have an answer, because I don't know. But I've been working on this course that I mentioned around how to present well to the board, and I was speaking to somebody about it, and they said, Well, do you just have a really high bar. This sounds a bit crazy, like the level of competency you're expecting, and slickness and professionalism. And I, of course, being the self critic that I am, was like, Oh, I do have a high bar. Oh, no, I'm being unreasonable. I'm required. I'm thinking that people should do more than they can do. Other people aren't all a star. Are massively insecure people like me. You know, the 100% right? I am asking too much in this course is not appropriate, and then in the shower, because all my thinking happens in the shower, I thought, no, fuck it. If people want to know how I've gotten to where I am in my career, there's a combination of luck, but really hard work and being at the highest bar and not accepting mediocrity and noticing when there's a full stop or not a full stop on every bullet, and prepping and working and rehearsing. And if you want to get ahead, it's both. It's not just luck alone. You do have things that you can control, and you have to work hard at it in boring, tedious ways if you want to get to the top. So anyhow, I have a high bar, and it's an acceptably high bar.

I like that, so I think you hit the nail net here, which is, it's not a question of luck, it's question of what is in your control, what is out of your control, and what is in your control is your skills, your competencies, your work ethic, all of that matters, and being primed up and ready to do the next thing. So if you're whatever your job is, you want to be awesome at that job, and you want to be in the best possible position to take that next job, because you're awesome at your current job. And that is what's in your control. What is out of your control is company circumstances, the market circumstances, people around you, et cetera, et cetera. And really what you're hoping for at the end of it is a combustion, a combustion of being at the right place at the right time, with the right skill set, which is you and bringing that to the table. And when that happens, magic happens.

I'm gonna add one point to it, which ties into the conversation with Alina and to your previous question of knowing when to go, is you make luck that way? It's an art rather than a science, of is this company not going to go anywhere or not go anywhere enough, or is there a better opportunity? And so actually not staying the four years to be fully vested is the Wiser thing to do, because there's a better opportunity out there. I find that the people in San Francisco or Silicon Valley are very good at this, but almost annoyingly So, if you look on their CVs, it's like, every 18 months to two years, they're switched out and out and out and out, because they're all they don't want to be millionaires. They want to be billionaires. And you have to, like, find the right luck, and they might be doing it a little too much, but it's definitely a way of manufacturing luck versus sticking with it and hope, rather than reality, that this one's going to deliver it for you.

I don't know who told me this, but somebody was saying to me that in Silicon Valley on the West Coast, you have a lot of people that focus on specific ranges. I'm series A to Series C, and that is what I do. And I do that over and over again, whereas in the UK, this is my understanding from this recruitment fellow that I spoke to, he said it's the exact opposite. Nobody wants to be pigeonholed into a band. They want to be the person I can go all the way. And that we haven't learned our lessons here in Europe, which is, if you want to manufacture your luck, as you just talked about, hit your sweet spot, hit your range, and get up to bat again and again every two years with that specific series A to Series C Company to get one to land. Yeah,

do that instead of two companies in 10 years. That is some

good, solid advice. So with that, why don't we go on a quick break, and when we come back, we will have our conversation with Alina broad.

I think for the first time in my career, I am very lucky to not be financially anxious about what that next move is. When I look back at all the times that I've changed roles in the past, I've had quite a lot of financial anxiety, actually, and so always that sort of like, what is coming next, which, you know, in one way, has kind of fueled ambition and wanting to kind of like, you know, have as many conversations as possible. But actually, I think it didn't allow as much as time and space to see what other things might come up. I

really found your insights around moving businesses and also time interesting because you've worked predominantly with slightly bigger businesses than I have. But as listeners will know, one of the things I'm always struggling with is, Do I like businesses until they get to about 300 400 people, and then dislike it because they're too big? Or is it because I've been at a company for four or five years and I just don't like being at a company there anymore? Why do I have an urge, and therefore other people as well, to leave companies after 345, years. And why do you have an urge to leave companies after that time

when I was leaving virgin and absolutely no regrets for staying at Virgin for as long as I did, but it did mean that. Because I was so institutionalized, it was very difficult for me to kind of move and kind of contemplate what else might be out there, almost like lack of confidence. Really, there's a bunch of different tools. But also, like, you know, I wanted to take a bit of time out do some personal development, but also I made a quite a strong commitment that's kind of stayed with me throughout the last 10 plus years, since moving and I think I just witnessed the younger generation kind of chop and change careers and jobs a lot more easily than I kind of felt like I was so committed, so invested, you know, felt like the place is not going to cope if I leave all of that kind of stuff. And actually, I saw these other people kind of leaving effortlessly, seemingly, and some great opportunities out there. And so I said the things that I really wanted to focus on was like, am I learning? So growth became a really big, important focus. It always had been, but just actively kind of tuning into that and saying in this new role is, am I going to learn something new? What am I going to learn from this kind of process? What's in it for me, but also from a company perspective and a business perspective, you know, what value like? Am I going to be adding value to the business as well? So it's all very well to be going and to be learning something new and exciting. But actually, is it useful you want to make sure that you want to be able to kind of, like add value and buy value, like the valuation of the company, like really, kind of making sure that you're working on things that is important, not just from my perspective, something that is not really going to swing the dial just for me. I think so. Seeking things out that kind of pushed my limits as well, like stuff that I'd never done before. I think actually, when I got called about the train line IPO to kind of help project manage that process, I remember literally saying, sounds like fun. How hard can it be?

I'm getting very hard

and therein. For the next six months, I was working seven days a week around the clock, so, you know, but I loved it. I was total deal junkie. So great experience. So

what I'm curious about is, when you go back to those virgin days you've been there for such a long time period, what was the criteria or set of thoughts that were flowing through your mind that tipped you over to say, look, the fact of the matter is, I've been at Virgin for 12 years, and I have to leave.

I would say it was a 18 month kind of process, actually, from when I decided and was kind of looking around the rest of the group and thinking, do I want to stay here for the next 10 years? Because there are a lot of people who live and stay with the group for a long period of time, and I felt like the opportunity for me to kind of continue to grow at the pace that I had done was not as exciting, and just the reality was the group was not adding new companies, all of that sort of stuff, new opportunities, as I had done in the early 2000s When I joined. So I think it was a combination of sitting there thinking, what is coming next? Could I stay here for the next 10 plus years again, and thinking, actually, no, that's not what I'm after. Like, I think had kind of exhausted the opportunities there for me, and I could have stayed absolutely and some people make that choice as well, to kind of take an easier path as well. I think I could have just accepted this is where it was going. And the group virgin women tradition was adding a property once every couple of years or so. So there was also another catalyst, which was a very strong one that also, I'd say probably was the one that kind of tipped me as well as my kids were young at that stage. We were in primary school, and my eldest daughter was just about to kind of transition into high school, and I'd been traveling quite a lot with Virgin and magician. We had properties all around the world, and that kind of space, I really had felt like I wasn't as connected and wasn't as around as I needed to be, particularly for my eldest daughter. So there was a bit about like, this has got to change. From my perspective, we're having a discussion about, when do you call it, when's the time to leave? But also what's really important to me is like, how you leave the job as well, and how you transition out is incredibly important, because the legacy that you leave is, I think, just as important as all the work you know that you've done to date. Once I left, I deliberately wanted to kind of have some space where I did a bit of contracting, mainly just picking up some work through friends and through the network.

And then you end up at train line, which is the exact opposite of that. And then

I end up at train line, and went completely in. But by that stage, I was ready for it. I'd sort of played with this, like, should I go fractional? I'm dipping in and out of a couple of companies. I helped some friends with a hotel development in Italy, and I was there in Italy when I got the call about train line, and I remember going, Oh, that sounds so much fun. So.

Let's talk about identity, because this is one of those things that, as I have left companies. I didn't do it on purpose, but I realized over time, my identity has become less and less tied with the companies that I'm with. And I can imagine after 12 years, somebody cut you in half, you would be what virgin red. I mean, you'd also be bloody, but, you know, appropriate virgin color

or pink as well, having most recently been at beauty pie. So I would say right now I am still using if I go to talks all of that kind of stuff, if people ask for your job title, and the company, I'm still using CFO at beauty pie as my title, I can kind of do that because we didn't recruit another CFO at beauty pie when I left, it allowed my finance director to step into the VP finance. So it was also opportunity for career progression and succession for him. So that kind of left a little bit of a space that I agreed with the team. And so I use that from an identity kind of point of view, which is makes it easier for me from an external point of view. But I think for me personally, I'm not attached to this that, you know, that title, I think. But it's probably taken me a few roles to get to that point, because people externally, there are banking relationships, all sorts of stuff that kind of happen when you're in certain C suite, roles in VC backed high growth companies that are entertaining you and spending lots of time talking to you, all of that kind of good stuff. And once you're no longer in that position, quite rightly, like you don't, they don't need to be spending as much time with you unless, of course, you'll kind of move on to the next, you know, new and exciting opportunity, and then they want to kind of talk to you again. So I think it's about just disassociating that personal ego side of things, like, This is who I am, and this is my role, and I'm, you know, important, it's like, actually, this is the role I'm playing right now. And depending on, you know, the role or the title, you have to kind of take on different personas, and also the state of the business as well. Some businesses that I've worked with as a CFO, I've had to be, you know, real tight ass, basically, and really, like, all over everything, and then other businesses have been like growth champion, and, you know, really cheerleading and kind of allowing mistakes to be made and things to be explored, because we're in that kind of high paced kind of growth.

So tell me this then, for the listeners out there, what should I think about, just in terms of, Is now the right time to leave or not. So they're getting to that point where they're starting to think about the possibility of it, what's what's the advice for that person,

particularly with the companies that we've chosen to kind of work with, and I'm talking about pretty high growth companies, often when we start the roles the companies in a certain state, and there's a certain amount of cleanup, hiring the right team, getting the processes in place, getting the growth plan in place, setting that plan, making some big changes. As soon as you kind of can, you kind of really hit the ground running, and you run like crazy for a good 612, plus 18 months, and you start to kind of reap the benefits of that. And I think as each organization that I've joined, I get faster and more efficient at doing some of that kind of stuff and bringing the people along with me. And so you go through an incredible pace of change over a relatively short space of time. That I think I used to say, is that funding circle, the two years that I spent some funding circle was like five to 10 years at one of the larger organizations that I'd worked at before, like just the pace of change, and when we, you know, very agile with what we did. So I think you kind of naturally get to a point where you've kind of cleaned up some of some of the mess, you've plugged all the holes. I think you kind of hit that point where you almost can take a bit of a breather and go what's coming next. And often there's a big plans in the pipeline, and you can sink your teeth into that over the next kind of period of time. But I think, like for me, naturally, I've kind of it's that two to three year mark because where I personally kind of find that sweet spot where it's got a starts to kind of rub between, okay, in terms of that philosophy of, Am I still learning? Yes, I'm still learning, but am I learning at the same pace as I did when I first came in? No, because I've kind of got under the skin of the business. And am I adding value? And I think sometimes too on the value side, there's absolutely a huge amount that you can kind of continue to produce, but I think that curve starts to kind of drop a little bit, and that, for me, is my indication where I'm like, Okay, we're on a path. Is there anything else that I can kind of do that can kind of swing that that's going to really sustain it, or is it on a it's on the path now that kind of had the vision for you. You know, 18 or so months ago, I'd probably say it's probably sooner for most people, for a very practical reason as well. Most vesting, you know, of options and all that kind of stuff, are generally straight over a four year kind of period. So there is stuff where you kind of leaving things on the table, or you're

lasting the four years, but not enjoying the second half nearly as much as the first half,

entirely. And or and I like to think too about with the businesses. And I say this to a lot of people who have worked with me too, like the businesses are moving at such a pace and such a rapid change that there are certain points in time, where you're right for the business, and where you kind of take it to a certain point, and then there becomes a point where you need to kind of let it go and let the next person to kind of come on and take it on in order to kind of take it forward. And I like to think that that's also, you know, something like you need to kind of work on being able to kind of release the work that you've done, leave your legacy, but allow somebody else to kind of come and change and continue to evolve it as the business takes the next step forward. And for me at beautify, I could have easily stayed for the four years. We had lots of lots of growth ahead. However, we we brought on board a CEO just over a year ago now, fantastic guy evolving the business and seeing where that was going to go. He was, he's obvious on his, you know, four to five year kind of trajectory. And I guess my time period sort of dis, like, disconnected a little bit from that point of view. Because I think if I'd stayed for another year, I think I'd be in this kind of zone of just like this change. There's things that he wants to kind of do which we kind of try. You

become the person who's like, we've already tried it before, and it doesn't work, even though, when you come in, you're like, why don't we try it? And let's see if it works this time. And suddenly you're that other person,

exactly. And I don't want to be that other person, I literally want to be, which I am now is the cheerleader coming in and on the side going, That sounds amazing. So I guess another signal could be also like change of that sort of, either founder, investor level, CEO, whatever you know, that kind of dynamic that could be a bit of a trigger for you to start thinking about, maybe now is the right time. I think you either have to decide, I am here to support this new person coming on board for the next for their journey, and I'm going to partner with them and do that, you know, that kind of process with them, or actually what they need is somebody that they recruit and hire and bring on board so they've got their core team that they can kind of do the best that they can kind of do over the next period. And from my perspective, my options should be good, right? Like

a lot of work that Maddie cross has done on the research that the best performing companies switch out their execs approximately every two years versus the ones that hold on to their execs. And so basically, it's great to become a specialist in a stage. My question is for myself, is, am I accidentally a specialist in a stage that may or may not suit me, just because it's the stage I've always done and I've never really had the patience to carry on to the next stage, and like, had I had my big career break at post Series C versus post Series A? Would I have a completely different stage that I'm specializing in? I don't know, but this is my stage now, so I think your experience very much ties in, and I love that of like, after 18 months, two years, you've done the change, and now it's time to let somebody else join who's excited about that next stage, and be able to go and do what you want next, which you see way more often than the people who start at three and go to 3000 and you see them. But I guess it must be like a tremendous amount of learning throughout, because I agree about needing to learn the other element that we haven't talked about, but is what has put you in a position where you don't need to rush to your next job, and I have that position as well, but mine was lucky and accidental, because it was the first stage of my career, and people in the valley are so good at this. Is it luck, or is it that you're kissing enough frogs that you get the frog that turns into the prince, because you're spending two years vesting well and moving on.

There's an element of I've collected. There's a bunch of ones which I'm waiting for some to like, come to fruition. So it is a bit about placing bets. And I think that is in that kind of choice, when you decide to take on a role, you know, there's no role that is perfect. I love the question that recruiters always ask, what would be your perfect role, right? I mean, it's a good question to try and answer, but I think at different points in time, you'll be wanting different things. But I think if there are certain things that it ticks the box that you. Agree are aligned with the brand's kind of vision and purpose. You're going to learn something new. You know that you can kind of add value to the company all of that kind of good stuff, but part of that also financially, you need to understand, you know what your base package is, and you know your options, and what potentially could that be worth. And I think that's where that value bit really comes in. Like, am I going to be able to and we're all in C suite roles, am I really going to be able to influence, can I work with this team? Like, that's where the magic in the exec team is really important, in that communication and having a kind of high trust collaborative environment is critical. But also with the founders and that board dynamic, all of that sort of stuff, all kind of comes together to, you know, are we all working together to be able to kind of grow the value of the company? And at some point in time, I don't have to be there for that transaction and get that kind of pay and then kind of leave. I'm quite happy with some of the businesses that I've gone on that actually preserving what I've earned and being able to kind of, in some cases, negotiate an acceleration of vesting because of the way I've transitioned out. There's also an option as well, but also they're sitting there as potential bonuses to come down the pipe, which is why I think it's so important for you to kind of transition. Well,

let's talk about that actually, of like, what are the hints, not necessarily, how to transition well, but what should you be negotiating? What are the things that you've seen, either you've done or others have done, to put yourself in the best position if you are leaving two years out of your four year vesting? So

in all cases, from my perspective, I think it's been open, very open conversations with my CEO and or founder at the time. I think there was only one situation where, actually it was when I was leaving to go to beauty pie. It was a really tight mid deal with a private equity company, and I needed to give notice. So handling that, I think the founder didn't talk to me for a good week or so, so that was a bit tough. But my promise to him and to the investors coming on board, actually was, I'm here to see the deal through, and I've negotiated with beauty pie to kind of make sure that they would wait, you know, for me to kind of do what I needed to do with RFI. I hired my replacement, made sure that there was a proper transition, and have been, you know, available for the company as well. Post that that, I think, reassuring them that there is a way forward as well, whether that be through succession planning, bringing people up through the business and or remaining involved in the business post, leaving

before we go. If our listeners can only remember one thing from our conversation today, or can only take one thing away, what would it be something

that I haven't mentioned, but I think it be curious. So always be curious about what your day has got ahead of you and what the next period of time has got ahead of you. And always asking yourself, what is it that I'm learning? And again, that whole thing about, you know, am I adding value here? And when you start to kind of have that little flicker of, maybe there's might be something else, start having conversations with people. Take those conversations from recruiters or talk to friends who are in working in different businesses. Doesn't matter if you turn things down whatever, but just it gives you those sparks of ideas of some of the things that might kind of be out there. And sometimes the universe works and brings you to new opportunities that you never thought you know you would do. I think that curiosity kind of mindset just allows you to, if you have your head down too much, going, No, this is all I'm doing for the next five years. Then you're not going to see those opportunities or get that niggly feeling in your stomach.

So I am getting a wriggly feeling in my stomach, which is that it is time to wrap this episode of the operations room. Thank you for joining us. Elena Broadfoot, and if you like what you hear, please leave us a comment or subscribe, and we will see you next week.