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Tech and Teams: Caroline Plumb’s Growth Playbook

SheSaas Unplugged · 2025-10-12 · 41 min

0:00--:--

Key moments - from our scoring

Substance score

48 / 100

Five dimensions, 20 points each

Insight Density10 / 20
Originality9 / 20
Guest Caliber13 / 20
Specificity & Evidence9 / 20
Conversational Craft7 / 20

Caroline Plumb, serial founder and former group CEO of private equity-backed Grevita, shares a comprehensive growth playbook built across scaling multiple businesses in the SME and fintech sectors. During her three-year tenure at Grevita, she scaled the accounting services firm from £10m to £60m revenue through six strategic acquisitions paired with aggressive digital transformation - a journey she breaks down into actionable frameworks for post-merger integration, technology adoption in traditional industries, and segmented go-to-market strategies. Her earlier exit of Fluidly, a cash flow forecasting SaaS platform acquired by Oak North Bank, further informs her perspective on founder dynamics during transactions and shareholder alignment. For B2B operators scaling through M&A, leading technical transformation in non-tech-native teams, or targeting the fragmented SME market, Plumb's insights on day-zero integration playbooks, handling diverse buyer personas across prosumer-to-medium segments, and balancing employee retention with strategic objectives offer concrete, battle-tested methodology applicable across regulated and traditional industries.

Key takeaways

  • →Successful M&A integration requires a detailed playbook with hour-by-hour day-one execution plans, phased 0-30-90 day timelines, and coordination across technical, financial, and people-focused workstreams.
  • →Technology adoption in traditional industries like accounting improves when framed as bringing personal technology behaviors into professional settings, with clear communication that not everyone needs to be a first-adopter.
  • →The SME market segments into micro (sole traders), small, medium, and larger subsegments that each require different go-to-market strategies ranging from product-led growth to field sales approaches.
  • →Private equity's 3-6 year hold periods create strategic advantage by allowing sufficient time for meaningful change without encouraging complacency or short-termism.
  • →Founder exits require balancing three distinct roles - employee, shareholder, and director - which often misalign during transactions, requiring intentional stakeholder management.

In this episode

  1. 1Introduction to Caroline Plumb and Her Background
  2. 2Scaling Gravita: Growth Strategy and M&A Playbook
  3. 3Technology Transformation in Traditional Industries
  4. 4Post-Merger Integration: People, Systems and Culture
  5. 5Working with Private Equity vs. Other Ownership Structures
  6. 6Go-to-Market Strategies for SME Customers
  7. 7Founding and Scaling Fluidly: From Idea to Exit

Mentioned

Caroline PlumbGravitaFluidlyOak North BankFresh MindsChristine MaslinSheSaas UnpluggedChatGPTNetflix

Guests

Caroline Plumb

Topics in this episode

Private equityCash Flow ForecastingPost-merger integrationGravitaFluidlyOak North BankM&A integration playbooksSME market segmentationPrivate equity hold periodsFCA regulated fintechCredit control automationTechnology enablement in traditional industriesSME segmentationM&A integration playbookDigital transformation in accountingtechnology adoption in accountingM&A playbooksregulated financial services

Questions this episode answers

How should you structure post-merger integration when acquiring multiple companies in quick succession?

Break integration into three phases: day-zero with hour-by-hour communication cascades; days 0-30 covering technical consolidation, financial controls, and governance; and 30-90 covering broader cultural alignment and brand unification. The bulk of work focuses on people - how teams join, when to rebrand, and ensuring stability (keeping clients and managers unchanged initially) before driving corporate-level change.

What's the best way to drive technology adoption in traditional industries like accounting without overwhelming staff?

Frame technology adoption using employees' existing personal tech habits (mobile phones, ChatGPT, Netflix) - showing the gap between their consumer and professional tech use. Survey where people sit on the adoption curve and allow tiered participation: not everyone must be a first adopter; people can be supporters, cheerleaders, or mentors rather than active users, as long as they're not actively obstructing change.

How should you segment the SME market for different go-to-market approaches?

The SME market isn't monolithic - segment it into prosumer (sole traders, micro-businesses), small SME, medium SME, and larger SME, each requiring different sales motions. Prosumer segments need product-led or marketing-led growth; mid-market segments (£10k+ customer sizes) can support inside or field sales. This nuance matters especially in regulated industries where customer vetting and risk assessment become additional layers.

What are the advantages of a private equity ownership structure compared to VC or listed company ownership?

Private equity's 3-6 year hold period balances strategic thinking with urgency - long enough to drive meaningful change and focus on value creation, but short enough that complacency isn't an option. This contrasts with listed companies' quarter-by-quarter short-termism and founder-owned businesses' lack of external structure.

How do you handle conflicting interests between your roles as founder, shareholder, and director during a business exit?

Recognize that founder exits involve wearing three hats simultaneously - as employee (career), shareholder (returns), and director (duty to stakeholders). These often align during operations but diverge at transaction close. Spend time understanding different constituents' perspectives and work with board leadership to craft outcomes that work across all groups rather than optimizing for one.

What our scoring noted

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

Insight Density

10 / 20

The episode contains a handful of genuinely useful ideas - the M&A integration phasing (day-zero to 30 to 90), the SME segmentation framework, and the misaligned-hats model at exit - but they are spaced out by substantial padding: OBE storytelling, quickfire fluff, and generic motivational commentary. Insight-per-minute ratio is low.

we would think of it in three phases. So there would be a, um, kind of day zero, day one activity. So the first day we would literally have a calendar that went hour by hour
lots of those segments can be loss making as well. So the acquisition cost can be high and the lifetime value can be low. So unless you get it really Right. It's very easy to overspend your CAC

Originality

9 / 20

There are two or three genuinely fresh framings - the 'assassin vs. supporter' technology adoption spectrum and the augmentation-vs-substitution distinction in tech - but the bulk of the content recycles standard founder-to-CEO narrative arcs and leadership platitudes without contrarian or first-principles tension.

What you can't be is negative. You can't be an assassin, you can't actively work against it. But you don't have to be the first adopter
what's really interesting about technology is when you can make a whole new category. So that augmentation use case, what is it that you can now do that you couldn't do before?

Guest Caliber

13 / 20

Caroline Plumb is a legitimate practitioner - she founded and exited a fintech, then ran a PE-backed rollup from £10M to £60M across six acquisitions - which puts her clearly above thought-leader territory; however the transcript doesn't surface the depth of operational detail one would expect from someone at that scale, leaving caliber somewhat underutilised.

took the business from around 10 million pounds in revenue to 60 million pounds in revenue in just about three years
I studied engineering at university and worked as a software engineer um, for GCHQ for a few summers

Specificity & Evidence

9 / 20

A small set of concrete anchors exist - £10M to £60M revenue, six acquisitions, £10K average deal size in upper SME, three integration phases - but there are no named acquisition targets, no ARR or retention figures, no technology stack specifics, and no outcomes data from the integration playbook, leaving most claims at the level of assertion.

led Gravitas 6 transactions over that period
average customer sizes that might be £10,000, might be above that. And therefore you could start to use a more of a inside, uh, sales, perhaps even field sales, sales led approach

Conversational Craft

7 / 20

The host asks mostly open softballs and frequently validates answers with enthusiastic agreement rather than probing; the one genuinely useful follow-up ('why did you decide you didn't want to carry on with the business?') yielded real information, but it is surrounded by unchallenged claims, OBE tourism, and a quickfire round that contributes nothing substantive.

And sounds like you've got Your playbook very well oiled there, you know, down to the hour is really interesting to listen to
And I've never really looked at the SME space like that in terms of. Actually there's lots of different segments within that

Conversation analysis

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

Share of words spoken

  • Caroline Plumguest75%
  • Christine Maslinhost23%
  • Christine Maslinhost2%

Most-used words

technology26businesses21market21different18small17interesting17making13first13running13private12equity11point11piece11female10growth10thank10

Episode notes

How did Caroline Plumb scale Gravita from £10M to £60M in three years? On this episode of SheSass Unplugged, Caroline shares her bold M&A and tech-driven strategies in accounting, reflecting on her path from founding Freshminds to selling Fluidly to OakNorth Bank, fuelled by her SME and tech passion. We dive into seamless integrations, private equity versus VC, and why diverse perspectives drive success. Caroline opens up about her OBE, her Times column drawn from real business struggles, and how motherhood honed her empathy, boosting female partners at Gravita from 10% to 30% without quotas. We also explore fundraising tips for female founders, disrupting traditional industries, and fostering innovative cultures. It’s a candid, inspiring chat about curiosity and connection fuelling progress. SheSass Unplugged is

Full transcript

41 min

Transcribed and scored by The B2B Podcast Index.

Christine Maslin: Welcome to Shesess Unplugged, the podcast where we dive deep into the world of female leadership in the private equity SaaS industry. I'm your host Christine Maslin and I'm on a mission to spotlight the incredible female CEOs who uh, are making waves in our industry. Join us uh, as we embark on a journey to explore the triumphs, challenges and pivotal moments in the careers of 12 extraordinary female leaders. Over the course of 12 episodes, you'll hear firsthand from these trailblazers as they share their insights, experiences and the secrets to their success.

Christine Maslin: Today on she says Unplugged, I'm joined by someone who truly embodies what this series is all about. Visionary leadership, entrepreneurial grit, and a track record of scaling high growth tech enabled businesses with purpose and pace. Caroline Plum, obe is a serial founder and CEO who's led businesses from startup to significant scale. Most recently she was group CEO of private equity backed Grevita, a fast growing technology enabled services firm where she scaled the business sixfold, led multiple acquisitions and drove deep digital transformation. Before that, she founded Fluidly, a fintech startup focused on cash flow forecasting and the office of the cfo, which was later acquired by Oak North Bank. Caroline also serves as a non executive director at a publicly listed business and is an angel investor. In 2016 she was awarded an OBE and is a regular contributor to the Sunday Times where she writes about leadership, growth and entrepreneurship. Good morning Caroline. First of all, a very warm welcome onto she says Unplugged. And thank you so much for agreeing to come on and be our guest on today's episode.

Caroline Plum: Not at all. It's wonderful to be here. Thank you for having me.

Christine Maslin: Very welcome. So to kick things off, could you give us a brief introduction, uh, share a bit about your background and tell us what you're focused on today.

Caroline Plum: Yes. So my name's Caroline Plum. Um, I have quite an unusual background I suppose. I started life out as an entrepreneur and later in life have been running other people's businesses for them. Uh, so I always had that same sense of wanting to build something, interest in exploring new ideas and I really love the intersection of people and technology.

Christine Maslin: Wonderful. There's so much there that um, I'm really interested to explore during this episode and so perhaps Gravita is uh, a good place to start. You know you talked about starting out life as an entrepreneur and then now you're kind of running other people's businesses for them. Gravita, um, is a private equity owned business and you've, you know, You've really scaled that organization from joining as the group CEO in 2022 to departing relatively recently June 20. You took the business from around 10 million pounds in revenue to 60 million pounds in revenue in just about three years. Can you tell us a bit about that growth journey and what some of the key decisions were that helped to unlock that kind of growth?

Caroline Plum: Yes, well, Gravita, um, is in the accounting space. So a business that delivers audit tax bookkeeping to particularly small and medium sized businesses. And the business was built through a combination of organic growth but also a lot of M and A. So in particular led Gravitas 6 transactions over that period and across. You know, we built the business through a combination of wonderful people acquiring wonderful people, wonderful clients as well as delivering more and more to that base. So lots of key decisions I suppose were to do M and A in the first place. That was always really set. The accounting market today is undergoing huge consolidation. There is a number of private equity firms operating in that market and in particular because accounting services are, you know, very stable, very close relationship between accountants and their clients and you know, a real growth opportunity. Plus it's a market that's really changing today with the impact of technology and the impact of um, private capital coming into the market. So it's a real transition point for the market. It's a really exciting time to be in it.

Christine Maslin: Yeah, no, absolutely. And you touched on that kind of tech piece because I guess they're, you know, you describe them as an accounting firm but they're kind of very technology enabled accounting firm and they went through quite, quite a technology, you know, a technical transformation if you like, during your, your tenure as CEO, uh, how do you take people on that journey, especially like a firm of accountants. Right, and get them excited about it rather than just, you know, really overwhelmed about that transition.

Caroline Plum: I think today technology isn't everything and actually people use technology an awful lot in their, in their private lives and their personal lives. Actually. It's in some ways it's people's professional lives where technology can lag at times. I think in accounting services and accounting software. A lot of that software historically has been quite outdated or at least long standing. So what you have seen is like a new wave of vendors, uh, who have started to digitize services into accounting firms and digitize the offer in the first place. So there is new now technology to adopt. It doesn't always have to be on premise older technology, but as a modern wave of cloud technology coming to deliver into that market. And then I think when it comes to people, I think so many people. And uh, I would say this to the team, they might have latest mobile phones, some of the partners had electric vehicles. People would think nothing of, uh, using ChatGPT to book a holiday or using the recommendations engine on Netflix. So actually there's a huge technology adoption in people's lives already. And actually one of the things I think that people are most irritated about, you know, if you imagine if you're in a going down an underground and someone in front of you is, you're putting in a ticket or you're at a supermarket, someone's typing in, you're so frustrated as a consumer, just, you know, you just want to kind of make it seamless and make it frictionless. So I think actually people, you know, everyone's an individual. Many people are actually interested in technology, but there is a curve. And I think to make people not overwhelmed, I think it's like, how do you translate what's going on in your personal life to what's going on in your professional life and get comfortable. But also I would say that technology adoption is very different throughout the organization. Maybe the different people's levels of confidence, maybe people's level experience with it. And so we did some work around surveying people in terms of where do they sit, you know, where do they feel themselves as adopters. And also, you know, I would say to people, you don't have to be on the pitch playing. I don't know why I do football analogies because I don't even like football. But some people can be supporters and cheerleaders, you know, fans. What you can't be is negative. You can't be an assassin, you can't actively work against it. But you don't have to be the first adopter, uh, you don't have to be the first person that's going to lean into that technology. It's perfectly wonderful to be someone that says, I encourage encouraging others or just show an interest or just mentoring and providing support to other people that are adopting. But I think over time you can change the technology enablement and technology adoption and culture of an organization by building in lots and lots of small layers that, uh, over time change the stance and change the attitude around it.

Christine Maslin: Uh, yeah, really interesting insight which kind of leads on to the next point I was going to make or the next question I was going to ask around those six acquisitions. You know, that's quite a different way to grow from, you know, from organic growth. And I suppose I'm interested in that post merger integration piece, and, you know, how you integrate the people and the systems and, you know, how does that actually work? Can you tell us a bit about your experience with that, uh, on those six acquisitions at Gravita?

Caroline Plum: Yes, I think. I think we learned a lot over time as we developed the playbook and developed what works and what didn't work. And we would take each of those learnings into the next transaction. I think the first piece to start was always getting it thought about deeply before the transaction. So, you know, part of the deal, really making sure we're aligned on culture, first of all, and making sure that that's going to be a fit, you know, before. And then lining up, um, people's key roles, key areas that they're going to be most involved in. And then when it came to the actual transaction itself and the purse merger piece, we would think of it in three phases. So there would be a, um, kind of day zero, day one activity. So the first day we would literally have a calendar that went hour by hour. So a full running order of communications, checklists, whether that was to people, to clients, to suppliers, uh, which order we were going to do the communication in, who was going to do it, how that worked, down to the hour, down to the minute, in places, kind of full cascade. Then we'd have a plan that was sort of days 0 through 30, and then 30 through 90, and then after that, more of a BAU. And the integration plan would cover many, many strands from technical areas in terms of how we're going to bring together the ways of working to financial matters, how are we going to consolidate accounts, finances, into our group accounts on day one or by the end of month one? What controls and governance do we need to have? Um, on day one? What can wait till later? But most of it, I would say, was all around people. So how do we bring teams together? At what point? How do we make people feel part of a single brand? Uh, at Gravita, the strategy was very much to be a tight integration and to change the name of all the firms that we brought into the business to be one firm. That's not the same strategy lots of others take. Many people keep their own brands over time. Many people transition over a longer period. You know, we tended to believe we were very focused on one team and one agenda. So for us, a tight integration was important, and that meant a lot of coordination across multiple strands. And ultimately, how do you bring together a set of culture, set of values and people into one vision?

Christine Maslin: Yeah, really interesting. And sounds like you've got Your playbook very well oiled there, you know, down to the hour is really interesting to listen to. And you know, going back to your point about what you can't be is a toxic person who's, you know, being very negative. Um, and I suppose that can happen in integration scenarios more than anything because people start to feel left behind or not part of the new journey. So that, that strategy around communications and keeping people at the center of everything that you're doing sounds like that's paid off very well for Gravitar as a business.

Caroline Plum: I think so. I think it's always difficult because the times of change and people don't always want change and often it can be a surprise as well for people coming into a transaction. Obviously for confidentiality purposes. Not everybody is aware of a deal before it happens. And so lots of people in very different parts of that change curve and awareness and often we would focus very much on, I mean the first rule of anything is don't break anything. So in transition. So the first piece is very much making sure that we're being reassuring that you know, your, your, your client isn't changing, your manager, manager is not changing. If you've got training, go ahead. If you own that, if you've got holiday books, go take it. So things that create stability for people as individuals and then you can start to think about the corporate after. But getting both those pieces right I think was really important.

Christine Maslin: Great. Yeah, thanks for sharing that. And um, what, you know, I guess you worked with VCs at fluidly when you founded your own business and will, we'll go on to talk about that, you know, a little bit later but at Gravita you, you started to work under private equity ownership which is very different. Can you tell us a little bit about what you, you know, what you learned about working under private equity?

Caroline Plum: It's actually really interesting because the question is how much does a shareholder affect the business and what is the interaction? And as you say, I've had the opportunity to work under uh, my own business fully. So um, with small angel investors but, but also on a sustainable basis without much external investors under a VC environment. Under private equity environment I've been a board member of a listed business and we used to buy partnerships. So I've seen pretty much every different type of equity structure or shareholder structure that there is operating in the UK market. And I would say that one of the big pluses for private equity is the time frame. So I think lots of businesses can be quite short termist, notoriously retail businesses that are listed on markets. Because retail investors can be quite short termist. The criticism often of listed businesses is a short termist quarter by quarter nature, uh, of the business. Whereas I think one of the big benefits of private equity is that uh, because most of the investment is taking place over a period of four to five years, three to six years depending on the fund, it's enough time to think strategically about the business in terms of how do you drive value, you, where do you focus. Enough time to make change a window short enough that you can really focus on making that change in a certain time frame, but not so long that anyone can be slow or lackadaisical about it. So I think one of the, for me one of the big benefits of private equity comes to the structure of the, and the timing of uh, their hold period and the focus that that brings.

Christine Maslin: Yeah, really interesting. Thank you for sharing that. So talking about Playbooks and we talked about, you know, you've got a very well oiled machine on the M and A side of things. Can you tell us a bit about um, your playbook for building go to market strategies for SME customers, especially those in regulated or traditional industries?

Caroline Plum: Yes, I am a huge fan of the SME market. It's really the area that I spent the last decade or so and we'll always continue to focus on. I'm really passionate about SMEs and I think it's because so much of the UK economy of all economies are affected by the impact of small and medium sized businesses. And it's not obviously large enterprises get all the headlines, they're the ones in the press all the time. But actually so many people's lives and communities are affected by the impact of small businesses. I think what people get wrong about the SME market is they tend to think of it as a block. So people think are you either working for consumers or for enterprises. But what is most interesting about the SME market is it's so different in the different segments. So at one end you have what I would call prosumer. So this is really a kind of sole trader, very small business. Perhaps a sole director, sole trader may or may not have an employee, you know, really tiny micro business, almost like a consumer but, but more sophisticated in their buying habits. So prosumer, then you'd have the S of SME, the M of SME and then kind of like the more larger section. So I kind of think of it as sort of mini, micro, micro mini medium max in the SME segment. And, and what makes therefore the go to market really interesting is that because the revenues tend to be much smaller clearly in the prosumer segment. So you're looking there at product led growth, marketing led growth, whereas in the larger part of the segment you're getting into average customer sizes that might be £10,000, might be above that. And therefore you could start to use a more of a inside, uh, sales, perhaps even field sales, sales led approach. So within this one market segment, as people see it, SME, you've actually got the full range of kind of go to market there and lots of different sales motions, lots of different marketing motions. And that just makes it for me the most fascinating part of the market to be in. I really like it. And of course that's thinking still at the firm level, within a firm, um, you tend to have different buyers and it's very different whether you're spending your own money, my money or my business's money, mentally where people have their spend frame. So for me it makes a proposition really interesting. It makes the go to market really interesting. And I think that's the case where it's regulated or traditional. The challenge, additional layers with regulated industries is that you have to be quite careful in terms of your proposition statements that you're making the products that you're selling. And particularly if it was a market like um, regulated financial services where there's credit involved, obviously giving, sending, lending is one thing, but getting it back is another. So quite often just because you want to provide a service or product doesn't mean that you should. And so the regulated part of the industry again for me makes an extra layer because just because someone wants to buy that doesn't mean you should provide it or at that price point, or that price point needs to take into account trust, needs to take into account risk. You need to do a lot more work around the customer as well before you do it. So that's why I love it so much. It's the kind of complexity and the differences in the segments that are there.

Christine Maslin: Yeah, I mean your passion around that. The space is really clear and um, great to hear from an expert. And I've never really looked at the SME space like that in terms of. Actually there's lots of different segments within that, you know that piece that everybody just brands SME as a block like you say. So. No, really, really. Um, good to hear from you on that.

Caroline Plum: And lots of those segments can be loss making as well. So the acquisition cost can be high and the lifetime value can be low. So unless you get it really Right. It's very easy to overspend your CAC in certain uh, or get your channels wrong in such a way that you're never really making profitable customers. So then that requires real reinvention and real thinking about the go to market or a real shift in pricing and proposition or segments. So that's why I think it's so interesting that area.

Christine Maslin: Yeah, sounds like you could definitely help a lot of SMEs as an advisor in that capacity.

Caroline Plum: I would have thought nerd on about it far too long.

Christine Maslin: So let's go back to your experience as a founder. Really interesting journey at uh, Fluidly for just over five years. You started the business, you built the business, you scaled the business and then you sold it to Oak north bank in, in 2021. Tell us a bit about that journey and you know, starting with what inspired the idea.

Caroline Plum: So Fluidly was actually the second business that I founded because the first one I started when I was 21, um, a business called Fresh Minds and that was in the consulting and recruiting space. And having grown that business, either you, well you're running your own business. That's why, probably why I was passionate about small business because there's so much going on. And um, I often think running a business is like juggling lots of balls in the air. You've got so many, you've got people, you've got finances, you've got sales, you've got marketing technology. You've got to keep a whole load of plates spinning, balls moving. It's not straightforward. The one thing that I think you can never afford to take your eye off is the finances. So for they're all balls but one of them is really a nice. And I think that kind of the thing that I think that keep people running business. I don't know whether you relate or not, but keep people up at night is the finances. And so what brought on Fluidly was the fact that I'd had that pain, that kind of, that uh, sense of I'm worried, I'm staying up at night, I'm worrying about money, I'm worrying about cash flow in particular. And so Fluidly was really built around that at uh, pain points and particularly what they call accounts receivables. So debtors and um, credit control and collection because I think that's a bit like laundry. If you don't do it every week, it just mounts up. So you just have to be constantly on your customers to pay you money. And obviously lots of industries don't have that characteristic, but lots of B.2B industries really do. And so fluidly was built around helping businesses sleep better at night by managing the cash flow. And in particular it did cash flow automation. So credit control automation, debt collection automation and payments automated cash flow forecasting based to give a full automated forward projection of finances and then identified businesses that might need additional financing and provide lending solutions to that pain point. Um, so we had a broking license, uh, it's a regulated business under the FCA. So I built the business, um, a software business, SaaS business, um, that was sold to the accounting channel to accountants and for use for their clients and ultimately also to um, some banks so they could provide services to their clients as well.

Christine Maslin: Really interesting journey. Thank you for sharing that and you know, really great to hear the inspiration for it as well. It's so, so personal, you know, it's experience that you've been through. Great idea and then clearly very well executed by you as well and culminating in a successful exit. How was that for you? Um, when you sold it to um, Oak north bank and then you had to walk away essentially you left, you know, you left the business to, to do something else.

Caroline Plum: Yeah, it was sort of um, I hadn't intended to leave the business at that point actually. So we agreed that I was going to stay and it was only later during the transaction that actually I had to say look, actually I actually would like to go. And um, so that was actually a real awkward point in the transaction. I was slightly worried it wouldn't go through after that. But we managed to, to do it I think, I think actually what's interesting is that at ah, the point of an exit as a founder you have multiple hats and you're wearing the hat of an employee in your career. What do you want for you? You're wearing the hat of a shareholder, uh, what's right for the shareholder, how do you deliver returns to them? And you're wearing the hat as a director, uh, and a duty to do the right by you know, all constituents in the business, most notably team. And so most of the time when you're running a business you're in full alignment with all those, you know, with all those constituents. But actually it's really easy to become misaligned with one of those groups at the point of a transaction. And so one of the key things I think was to try to think about, think of things from different perspectives and try to understand different people's perspectives, um, and views and how do you craft something that's going to work to those different teams and actually I think it was something that I spent a lot of time working on with my chair and I think we landed the business in a really good place in that regard, you know, for all the different people involved. Yeah.

Christine Maslin: And why did you decide, can I ask, that you didn't want to carry on with the business?

Caroline Plum: Actually because the direction was, um, heading away from SMEs. So we became clear that actually the best channel was our technology, best sold for banks. So we had as well as accounting clients, we also had a number of clients in the banking space. And it was clear that actually that was the better, uh, enterprise sales to banks was the better route for the business overall. That wasn't the area that I was most passionate about. I really do like the small and medium sized business market and so that was a factor in it. And plus I'd been approached about another alternative and the stars aligned to make that work.

Christine Maslin: No, it's a really good, valid reason and um, you know, I guess it just reinforces that. Do what you love, do what you're passionate about and then you can, you know, you can do the best job.

Caroline Plum: Right.

Christine Maslin: You raised funding from Octopus Anthemis, among others. What advice would you give to female founders looking to raise capital?

Caroline Plum: I think there's always a lot of press and negative press around female cat founders raising capital and how difficult it is. I can only say that wasn't my experience. And so I would say keep the faith, focus on your idea, focus on the business, focus on communicating why it's going to be a great market and why it's going to be a great business and try not to hold any worries, too many worries about that in your mind as you're pitching. I actually found that although often I was pitching to men to raise money, that it was, I didn't perceive any disadvantage, I have to say. And I, uh, think I was mindful about how I communicated business and myself and motivations for doing it. I think I spent time thinking about. I think whenever you're making a presentation, most people are going to forget everything afterwards. And so at, uh, best people are going to remember three things. And so I think if you think I can only remember three things about this person or about this business, what do you want them to be? And so distillation of your message into a few points and then focusing in on those points I think was really important. And so I would focus very much on getting clarity in my own mind. What are the key things I want to land and then making sure I did. And then my second thought would be that the, the meeting isn't over until you are out of the building and completely down the road with nobody else. So the number of times that I got a final question on fundraising between leaving the meeting we've had the lift, um, or the casual extra question at the end, the little extra, um, where people gave information that was quite common. And so I would say just be, be on it until, until you can actually take a breath.

Christine Maslin: Until you're out.

Caroline Plum: Until you're out.

Christine Maslin: It's really practical advice, um, and helpful I think for many of uh, our female members of Shesas and listeners. So thank you for sharing that. So we've talked about your experience as a founder, uh, your experience as a scale up CEO. When you think about your career journey from founding to scaling to investing because you've got a small portfolio of your own investments too, what's the thread that connects it all together for you?

Caroline Plum: Gosh, that is a really hard question. It probably is small businesses actually. So that is probably where my passion has been and whether that's running that, running them myself, selling to them, growing them, growing, you know, growing businesses that serve those markets and are focused on delivering to those markets or now investing in you know, what starts off as small business but hopefully be large scale businesses one day. I uh, think that probably is a core thread. I think the other piece was technology. So I started life, you know, even as a child I loved taking things apart. I was always fascinated by how things worked. I studied engineering at university and worked as a software engineer um, for GCHQ for a few summers. And now I even, I've obviously lost my original ability to code. But now it's all vibe coding and you can get involved in lovable and you know, why wouldn't you have a little tinker around the edges? So I think that passion for technology, understanding how technology can be applied to make people's lives easier. And I think when it comes to technology people and actually consumers, we're really good at seeing substitution use cases. So we tend to innovate only in increments. We're good at making Diet Coke, Cherry Coke, or we're good at uh, making things slightly faster, slightly better. But actually I think what's really interesting about technology is when you can make a whole new category. So that augmentation use case, what is it that you can now do that you couldn't do before? And how do you think of artificial intelligence more as augmented intelligence? How do you use something to provide superpowers to go further in your life? Rather than just make something a little bit cheaper or a little bit quicker. Now, I'm not saying there's anything wrong with cheaper and quicker. Of course not. But that's not where the excitement is for me when it comes to technology. So the threads I think are, uh, yes, definitely small businesses and SME markets, but then technology, its adoption, the way it changes the world and the way it makes, like, new things happen.

Christine Maslin: So let's talk about, um, one of your standout honors. In 2016, you were awarded an OBE under Queen Elizabeth II. Incredible. Can you tell us a little bit about that experience? And I'm interested in, you know, what was it like? Did you meet Queen Elizabeth ii? Did you go to the palace? What was it for? We want to know everything.

Caroline Plum: I have to say, it was completely taken aback, utterly humbled, very grateful. Had no idea how it came around. I was doing quite a lot of work at a time and still do around female founders, um, women in business and actually broader entrepreneurship. So younger people starting businesses. I did a lot of work with, um, the government on kind of starting businesses, advising around Small Business Council, national center for Graduate Entrepreneurship. Really passionate about people starting businesses, particularly younger people and women. And the. I think the honour was in reflection of some of those pieces. The actual day was wonderful. I got to take my daughter as well as my wider family. We went to the palace. It was then Prince Charles, obviously, now the King, uh, who awarded the honor. And it was just a brilliant day out and I have to say, just an experience like no other. And my daughter, who was 6 or 7 at the time, was absolutely fascinated by the Yeoman Guards who stood so still in their amazing outfits that she wasn't sure whether they were real or models.

Christine Maslin: They're quite incredible, aren't they? The way they stand there so still.

Caroline Plum: Unbelievable.

Christine Maslin: Oh, what an honour.

Caroline Plum: Uh, it was fantastic. Yeah, it was really lovely.

Christine Maslin: Thank you for sharing that experience. Yeah, I can imagine.

Caroline Plum: Uh, it was a great day.

Christine Maslin: I've read some of your, um, recent articles in the Times. Um, you write as a regular columnist, uh, for the Times and as, uh, a business owner. I found them really helpful. Um, I really like your writing style. Um, it's clear, it's relevant, um, and it's full of practical insights. How did that opportunity come up to write for the Times?

Caroline Plum: I was actually approached by them, um, who said, and they said that probably because I have had a very unusual career in both on the founder side and then more scale up, CEO side, that they felt that that would be interesting. And as you Say, I tried to make the column practical because I think you don't always get a lot of insight into how people think about running a business. And so much of running a business, especially when you run your own business and especially for a much trial and error, you know, you often doing things for the first time and so try to address topics that, you know, perhaps like hiring or performance management, people culture or go to market, what to do on just a really bad day. You know, when you hear everything just has gone wrong, you think, how do you keep up your motivation and your passion when you just hit with challenge after challenge? So it's quite an eclectic mix, um, in terms of things I write about in the column. And it came about.

Christine Maslin: Yes.

Caroline Plum: Um, I was approached by them and it's been really. It's been really fun to do.

Christine Maslin: Great. How long have you been doing it for?

Caroline Plum: Three years or so? Yeah, three and a half years.

Christine Maslin: And do you still enjoy it? Is it a chore sometimes? Or you, you know, you're excited to write the next piece?

Caroline Plum: Yeah, no, I really enjoy it. I keep a little list on my phone of ideas and, um, whenever things crop up in the week or the month, I think, oh, that's interesting. I make a little note on my phone and, um, then when it comes to writing the column, I go through all my notes and I think about, oh, this will be an interesting angle. So quite often it's reflecting something that I've grappled with over the last month or two, or something that I've thought about or seen or read and thought, gosh, perhaps there's a different perspective on that, or what is the impact of that. And quite often big shifts that, uh, get covered by newspapers are economic policy or, you know, political events or broader kind of world affairs. And that's dealt with through one lens. But actually, all these things impact SMEs. You know, if you're employing people, you have to care about what's going on in employment law. You have to care about, um, the cost of the cost of living and how that affects individuals and their lives and what people need. Which therefore means you have to think about, well, how do I make more money to, you know, to pay for these, or how do I get more customers? But that's also really hard if you're, Particularly if you're a retailer in this environment, particularly if you're facing lots of tax rises. So lots of. It's not easy at all running a small business or running a business, and yet it is the only source of wealth Creation for an industry. So we need businesses to grow, we need them to be productive and we need them to tax them to pay for everything else and our services that we love. So they're such an important part of the economy. Uh, and I really like writing a book.

Christine Maslin: You're a mum of three. How has being a parent influenced how you uh, lead and the choices that you've made in your career?

Caroline Plum: I um, say I've got three children who are currently 15, 13 and 10. I think whole, the usual pieces, I mean it really teaches you multitasking doesn't it, and perspective to juggle both of those things. I actually think toddlers are such fantastic negotiators, um, when they're small because they just say exactly how they feel and they would not take no finance. And I think sometimes that's so applicable to business. If you could just actually be a bit more candid about how they felt about things and really what they wanted, then people could be clearer about trying to find solutions. So I think there's lots you can learn and if you can negotiate with small children, I think you can negotiate with most people. So I think that's definitely an influence. I think from a choices perspective I probably have had a more of a UK based career until now and for me um, probably I'm looking at roles that um, have a slightly more um, international element and flavour. Um, so that's an area that I think I'm very interested in going forward. And I think the other piece from a practical perspective, I think when you, when you've been out of the workplace on maternity leave or parental leave and you come back, I think someone told me once that keeping a pilot light under your career was really one of the most important things like a gas burner, uh, if you let it go out completely, it's really hard to restart. But as long as you've got a little pilot light, no matter how small the flame, you can dial it back up again whenever you want. And so for me, keeping networks alive over the period I took leave, keeping myself engaged and interested and curious was really important. It's advice I always give to women who are um, taking some time out for maternity or other reasons and then on return, I think it's made me a more empathetic employer because I'm very focused on people's return to the workplace and things like flexible working policies, hybrid working policies. How do you. It, uh, was some of the first policies I changed at Gravita actually were with those policies which were not very generous at the time and you know, could always be improved, I'm sure. But, uh, it was actually the signaling of those areas, making sure workplaces are inclusive and diverse and recognize that people are, ah, you know, they come to you for work for eight hours a day. That's not the whole life. And so it has to be something that builds around that. And so probably being a mum has influenced the businesses that I've led and certainly influenced some of my choices. Yeah, yeah, excellent.

Christine Maslin: I mean, some of that advice is, uh, yeah, is wonderful and will be really useful for, you know, for our members and for our listeners. And just. You were touching on diversity there as well. And um, it just reminded me as I was kind of preparing for this interview, I saw a stat that you kind of, you'd increased diversity at uh, Gravitar from something like 10 to 30%, I think during those, that kind of growth period of 10 to 30 million. And I think it was the female partners. Was that an intentional move? And if so, how did you do?

Caroline Plum: Wasn't really intentional in the sense I never had a target and there was never a sense that I must find or promote women particularly. So it wasn't sort of a, I'm

Christine Maslin: going to do this, I'm going to focus on women specifically. Yeah, yeah, yeah, yeah.

Caroline Plum: It wasn't an active, um, piece. It was more the natural, I think, outcome of building a culture where certain things were acceptable, certain things were not acceptable. Creating a culture of more flexibility as well. I say we partners were seen as individuals that could only ever, uh, be full time. And actually we sort of challenged that and said, well, why couldn't you be a partner three days a week or four days a week? What would that look like? So sometimes change the role premise. And actually that actually wasn't the case with actually in the female partner group. It was probably, I would say I had more male partners. The fact it became a conversation that could be had and built a broader, um, workplace culture, I think went to that part. I think once you have, um, more female leaders in senior roles, actually others do gravitate. So we did see a higher uptick in applications when we made lateral hires. We saw more applications from women probably as a result, and certainly through the promotion ranks. And I think probably that the culture over time built. But it was never an intentional stated objective. And I would say it wasn't the only metric that we had diversity on as well. We were very diverse in other ways in terms of age, um, race, ethnicity and gender. I think it just. But I think it's a question of how do you set. Set the tone overall?

Christine Maslin: Yeah, very good. Um, okay, so I think that that pretty much brings us to the end of our, um, of this episode. Um, apart from just one quick fire round, if you're ready for that.

Caroline Plum: Of course. Yeah.

Christine Maslin: What's a book or podcast that's inspired your thinking?

Caroline Plum: A book is you Talking to Me by Sam Leith. It's a really good book on structuring presentations and, um, rhetoric, actually, and the art of rhetoric.

Christine Maslin: I am writing that one down. That sounds good. Always like to take these recommendations. What's your go to way to reset after a tough day.

Caroline Plum: Probably outside in nature. So I live near some woods and so for me, um, trees, greenery. Being outside is I find really calming and grounding and so probably that's a reset.

Christine Maslin: Lovely. One thing people would be surprised to learn about you.

Caroline Plum: So I m. My middle name's Lucky.

Christine Maslin: Love it.

Caroline Plum: Um, it's actually Mongolian. Well, it's Mongolian. It's a Mongolian name called Bayan Te, which in, um, which bayan means luck and te is with. So, yeah, it's.

Christine Maslin: I'm half Mongolian.

Caroline Plum: Oh, amazing.

Christine Maslin: What a great middle name.

Caroline Plum: Love it. It's like Felicity in English.

Christine Maslin: Yeah. Are you a night person or a day person?

Caroline Plum: Day. Yeah. I'm actually kind of one of those annoying morning people that like to get up and do things, but by 10 o' clock at night, I'm ready for bed.

Christine Maslin: Me exactly the same.

Caroline Plum: Yeah.

Christine Maslin: My. My husband is not a morning person, but I am. Tea or coffee?

Caroline Plum: Tea.

Christine Maslin: Me too. Jasmine green tea, to be precise. Ah. Uh, what do you have an English breakfast or.

Caroline Plum: Yeah, it is an English breakfast. It's that morning piece, isn't it? Um, I just really like it.

Christine Maslin: Well, look, it's been really. It's been a real privilege to, um, to interview you on today's episode. Caroline, thank you so much for your time. And, uh, yeah, I shall be. I shall be keeping an eye on the. On the times and your articles coming out and also, you know, wishing you all the best for, for the next chapter, uh, in your career.

Caroline Plum: Thank you so much. Been pleasure. Thank you for having me.

Christine Maslin: Thank you for listening to this episode of Shesass Unplugged. I hope it inspired you in your personal journey. If you enjoyed listening, please subscribe and share this episode with others. You can find out more about Shesas at, uh, our website, shesas.org you can also find us on LinkedIn.

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