32. Revolutionizing Recruitment and Unlocking Human Potential
EPISODE 32
Caitlin McGregor’s journey as the founder of Plum transforms the hiring landscape by embracing data to reveal innate talents rather than relying on traditional resumes. The episode explores how technology and behavioural data can help businesses thrive while ensuring that employees are matched with roles that allow them to flourish.
Catch the Conversation
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Caitlin MacGregor, CEO and co-founder of Plum, is passionate about helping people reach their true potential. That’s why, after building two businesses for other people, she founded Plum – to help organizations fully leverage the human potential within their workforces. Plum equips business leaders with the talent data needed to match employees’ talent to roles where they’ll thrive, so that the business can thrive too. She is a regular speaker at global events including CES, Human Resource Executive HR Technology Conference & Exposition, Americas’ SAP Users’ Group (ASUG) Women Connect, HRCI Higher Standards Summit and more. She also is a sought-after guest on podcasts including, Recruiting Daily, The Recruitment Flex Podcast, and 3Sixty Insights. In addition, she has been quoted in the NY Times, Financial Post, The Globe and Mail, The Record, Global News, Human Resource Executive, and Benefits Pro. Caitlin is a gold GLOBEE Women World Awards winner for Achievement in Innovation and was named an Inspiring Leader by InspiringTM Workplaces.
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Julie: 0:04
Welcome to Figure Eight, where we feature inspiring stories of women entrepreneurs who have grown their businesses to seven and eight figures revenue. If you're in the mix of growing a bigger business, these stories are for you. Join us as we explore where the tough spots are, how to overcome them and how to prepare yourself for the next portion of the climb. I'm your host, julie Ellis. I'm an author, entrepreneur and a growth and leadership coach who co-founded, grew and exited an eight-figure business. This led me to exploring why some women achieve great things, and that led to my book Big, gorgeous Goals. Let's explore the systems, processes and people that help us grow our businesses to new heights. If you're interested in growing your business, this podcast will help. Now let's get going. Hello and welcome to this episode of Figure 8.
Julie: 1:06
Today, I am joined by Caitlin MacGregor. Caitlin is the CEO and co-founder of Plum, and she's passionate about helping people reach their full potential. So she built businesses two of them for other people and then she founded Plum, which helps organizations fully leverage the human potential within their workforce. It equips business leaders with the talent data needed to match employees' talent to the roles where they'll thrive, so that businesses can thrive too. And you may have read about Plum. They've been in lots of news media, in the New York Times and the Globe and Mail and global TV all over the place, and I'm so thrilled to have you here today. Welcome, caitlin.
Caitlin: 1:48
Thank you so much for having me. I'm really excited for this conversation.
Julie: 1:51
Yeah, I'm excited too and I love sort of like homegrown story, and female entrepreneurs obviously are my thing and I'm so glad to have you here because I think it's so interesting. You know the technology company that you founded and sort of what your why was. What can you tell me about you know what gave you the inspiration to start Plum?
Caitlin: 2:16
Selfishly. I needed Plum in order to be a successful CEO. First and foremost, it started out of I was my first customer and I saw the value firsthand. And then it's grown over time to now my why is really my kids. And I'll take a step back and kind of explain how we got here. But, yes, at the end of the day, the story still came back to I couldn't do my job unless I had this data.
Caitlin: 2:48
So I had built two businesses for other people before starting Plum and the second business I was hired by a Canadian educational technology company to go down to New Hampshire and start up and run the US branch. And my executive coach at the time said Caitlin, if you screw up that first hire, it'll be a loss of $300,000 on the business. So, not wanting to make that mistake, I ended up using this psychometric assessment, this behavioral. I was able to use this assessment on every single applicant that applied for the job and we had 80 people apply for the job and two candidates stood out for totally different reasons. One was this guy who was perfect on paper. He had a master's in education, five years of relevant work experience. My CEO back in Canada was drooling. This was the golden boy by every measure, but the assessment showed that he had a mediocre work ethic. But he was hired anyway. And then we had this other person and she scored in the top third percentile of the entire workforce for overall productivity, and my executive coach said that statistically she was one in a thousand and I'd be an idiot not to hire her. So I ran an experiment and hired the guy that was perfect on paper and the woman that had the highest assessment scores, and three months later the guy's fancy football team was doing really well, but he was only doing 10% of his work. So he was let go, and the woman was doing not only all of his work and hers, but within a year and a half she had replaced me as acting president while I went on maternity leave. And the punchline is is that she had two art degrees, her only work experience had been seven years of waitressing and she didn't even know how to use Excel. So if I had relied on a resume, there's no way I would have screened her in to interview her, let alone hire her. And so this is how I grew the business over three years I just kept screening in these incredible diamonds in the rough.
Caitlin: 4:43
The next hire was this high school student that we wanted to hire 20 hours a week to do our social media and our new website, and he was literally outperforming people that were making over a hundred thousand dollars, and he's since gone on and founded his own companies. And the next person had dropped out of college to literally join the circus. So we hired an ex-Carney best customer success manager, no tech experience prior, and we could just see these incredibly loyal people that were so driven were top performers, and there's no way, without this data, I would have ever selected them out of piles of resumes. So I had already built two businesses for other people. I just started my family and really wanted to come back to Canada, and as an entrepreneur, you know like I'm just a gap closer. I see a problem and I want to close that gap, and it didn't matter if I was working for somebody else or if I was doing it myself. I was going to be working the crazy long hours and solving problems no matter what, and so there was an opportunity to say, hey, if I'm going to put in the blood, sweat and tears. I might as well this time, do it for myself and my co-founder, who's my husband.
Caitlin: 5:55
We had been working together at the ed tech company. He was the expert in the software and he's the one that got me the job. And so we moved down to New Hampshire and ran that business for three years together and we also realized that we worked better together than not, and, being an entrepreneur, you know the sacrifices, you know the long hours, and it's much easier if somebody has the same kind of understanding of your whole life and commitment and the trade-offs. And so we had loved working together for those three years and wanted to come back to Canada because we had started a family, and so we're like we should do this for ourselves, we should run our own business. And he came back from work you know I was two weeks overdue to give labor and he's like I've got the idea. Let's take this consulting service, let's take it out of the hands of these really expensive consultants and let's turn it into software as a service. Let's democratize access to it so that every single person and every single role can be matched based on this data. That, based in industrial organizational psychology, is four times more accurate than a resume at predicting on the job success.
Caitlin: 7:01
And so we started it because I could never imagine successfully running our business or somebody else's business without this data. It's like putting a pair of glasses on. And so I was like I'm not going to be successful unless I have this. So I might as well go and build something that really, at that time, didn't exist as a software. And then now you know, our kids are 13 and nine and you know I don't care when they start their career if they're doctors, lawyers, teachers, nurses. I just want them to be happy and fulfilled. And when I look at the landscape for how people get matched to roles, there isn't a solution out there. And so we we kept going with Plum because we imagined a world like LinkedIn. Instead of it saying what you've done historically, it talks about what you could do if given the opportunity, and can really reveal to people what drives them and gives them a sense of self-worth and helps them match to jobs where they're going to flourish, because we believe that when people flourish, businesses thrive.
Julie: 8:04
So 13 years. Your oldest is 13. So you're basically coming up to that 13 year mark now and obviously building any kind of software product is a long and expensive road to go down. I know you've raised money over time. What has that been like for you?
Caitlin: 8:24
Yeah, I've raised 19 million Canadian to date. It's been a groundbreaking journey. There's very few women CEOs in Canada that have raised that amount of capital. I remember that when I went to raise I had raised 2 million of angel capital. So a lot of $25,000 checks at a time, a few more, a few that were a bit more, but a lot of individual people that were business owners themselves that believed in what we were doing and it took two years to raise that first 2 million. And I had my second kid in the middle of that. I literally fundraised pregnant. Surprisingly, nobody gave me money while I was pregnant. But two months after giving birth to my second I was on stage in Buffalo at a pitch competition where we won $250,000 US and then we had a whole bunch of other people come in on that to complete the full $2 million. But that was all angel money. That to complete the full 2 million, but that was all angel money.
Caitlin: 9:27
When I went to raise my first round from Venture Capitalists, it was a really interesting experience because I remember at the time when I started, bdc's report had said that there was no single woman that had raised $5 million in one chunk. Lots of women that had raised $5 million, but in pieces, piecemeal, like I already had in that 2 million in two years. So I wanted to be the first woman to raise 5 million in one go. By the time I did, I think there were about three other women that had done it by that point, so it wasn't the first, which was, you know, the more the merrier more of us need capital, but it was, and I didn't have the Rolodex. I'm in Waterloo, ontario, really amazing tech ecosystem, but a lot of bootstrapped companies, not a huge investor community. There's a good angel community, but we don't have a lot of venture capitals, or at least eight years ago we didn't have a lot of those venture capitalists here. And so what I found is that my network I wasn't one degree away from the check writers, and so it took me about two years to just build up my Rolodex, so that I eventually went through a hundred no's before I got to two yeses.
Caitlin: 10:52
And then, as I was down to two term sheets, one out of New York City and then one out of Toronto, slash Montreal it really came down to do I have an investor that I really can see being a partner with? Do I really believe that they have my back and that we are aligned, because if we're not aligned, eventually things are going to get tough and they're not going to be there. And I was really, really lucky that Real Ventures, which is based out of Montreal but has office in Toronto they were on their own transformation and their own journey, where they were really believing in investing in the potential of businesses that were trying to have the impact on that had purpose basically companies that were trying to do more than just make money, that they wanted to have a positive impact on the world. And you know, this was really about how do we give everybody the opportunity, regardless of their background, regardless of their experience, to really be in a career that allows them to be happy, fulfilled and thrive? So they really believed in the vision and at the time, janet Bannister came in as my lead investor and it was amazing to have a woman VC on my board and to nurture that relationship. And what? Years later, I can look back and say every time that it was one of those forks in the road where we had lots of potential but not necessarily enough proof for everybody to jump on board and say, okay, I'm going to fund the next round. Real Ventures and Janet were always there for us, just always there, and if there ever was misalignment, there was the work that was needed to find the alignment and it ended up being a really positive experience.
Caitlin: 12:45
But when you start on the hamster wheel of relying on outside capital in order to run your business and I just said I spent two years raising 2 million I spent two years, you know, building my Rolodex I, you know, got a hundred no's. Well, in the process of raising, you know, 19 million, I've probably had 400 no's, maybe 500 no's at this point. So there's kind of two things that I've learned from this. Besides the positive parts of like it's really important to find an amazing investor that really believes in you, is aligned and I'm very, very, very lucky on so many levels the things that I've realized is the number of hours that I put into developing that muscle of becoming good and successful at fundraising.
Caitlin: 13:33
I really wish in hindsight I had put those hours into learning how to be the best sales CEO ever. I'm a really strong operational CEO. I've obviously had success fundraising in the grand scheme of line me up against other Canadians, but I wish that I had developed instead of learning how to pitch decks instead of learning how to do a pitch competition instead of talking to VCs. I wish all those hours of getting good at that I had spent learning how to be the best sales leader, and that's been a journey that I've really had the privilege to be able to do, thanks to partnering with my chief revenue officer, who had that skill set and really was able to mentor me and coach me and do that peer learning where I've been able to develop that muscle. But I just go, oh my goodness, if I've only been doing that for the last three years, what would that have been like if I'd been doing it for the last 13 years?
Caitlin: 14:30
So I feel like celebrating the success of the investing is sometimes setting the wrong message to what does success actually mean as being an entrepreneur? And I think the amount of money that you've raised can be a misleading indicator. And the other part is that I truly believe and there's lots of research to support this I think the whole funding um market has changed in the last two years. The idea that Reid Hoffman put out the book blitz scaling was that an investor would put in $1 and they get $2 return. That was because valuations, you know, to $5 million in revenue, you could maybe exit for $70 million. Or if you get to $7 million, you may be able to exit for $100 million. So I have friends that as I was growing my business, when they got to $7 million Canadian, they had exits that were $100,000, $120,000, $150,000. That's amazing In this day and age. Those companies now would be getting three or four, maybe five X of valuation. The math is totally different.
Caitlin: 15:40
So they're maybe getting $35 million today versus when they did this $100 million that they got five years ago.
Caitlin: 15:47
Exactly so the rule book, the playbook that I grew up on, the playbook for really the first decade of running this business.
Caitlin: 15:57
That playbook now is in the garbage and has been lit on fire and I don't think it's ever coming back. So it's really, really, really important for people that are starting their entrepreneurial journey to go. Wait a second is that actually the right playbook? Is that the right risk reward? Is that the right way of running a business? And so it is. With technology at the time, developers are really expensive, Infrastructure is really expensive.
Caitlin: 16:27
I knew I could not build this business unless it had outside capital, and that was the goal from I'd already started businesses that were bootstrapped from other people. I wanted this to be VC backed, but now, with generative AI, I mean it is amazing how companies don't need to just keep adding bodies in order to grow. There's other ways to grow and scale, and I mentor through Real Ventures. They have a really amazing mentorship program and I have the ability to mentor two people that are early, and each of these teams are two people, four people, and my advice is don't spend a lot of time fundraising. If they're throwing money at you and one of them was it's like OK, that's great, but make sure you have alignment.
Caitlin: 17:11
But if they're coming to you, that's a different thing. But don't waste your time going out. And then the other thing is is don't just take that money and automatically start hiring a bunch of people Like what are the roles and responsibilities that aren't getting taken care of? Is that more important? What's the order of operations? Is that going to drive more revenue and is that just more generative AI, or is that an outsourced virtual assistant? There are more ways of solving it that are less expensive than how I was running the business in the first decade, and so there's an opportunity, I think, to do things differently than the playbook that I use to build this company.
Julie: 17:53
I think it's one of the really interesting things I'm seeing with entrepreneurs right now is sort of smaller core teams. Lots of things are sort of outsourced or third party or automated, where you know, we were hiring people for that not that long ago.
Caitlin: 18:09
Yeah, I mean we've definitely benefited from some of the newer trends. One is we went fully remote in COVID and when it doesn't work, it's because not enough resources have been put into how to make that environment successful. And when you're low on resources and cash, it's one of the first things that gets sacrificed. So it's not easy, but I think there are so many benefits, um, from being fully remote. I benefited from the fact that I had a core team that had years of working together in person. So, as the nature of our you know, team shifts and we get more and more of just remote people, you know I'm I'm reevaluating all the pros and cons, but it can be a really big unlock to to stay remote, cause you, you have a lots of possibilities. And then the other thing we've done is take advantage of fractional services.
Caitlin: 19:02
So we moved up market to enterprise four years ago and so we needed a chief security and compliance officer. I can't. I can't afford that person full-time and I don't have enough enterprise customers to keep that person busy full, full-time. We drink our own champagne. So, even though we can have a full-time HR person, you really want somebody who's at the forefront of strategy and thinking about things differently and really rethinking about work on a regular cadence.
Caitlin: 19:33
Who also is seeing how other businesses are changing? So we have a fractional chief people officer. My CFO is on mat leave, so we have a fractional CFO while our manager of finance can run the day-to-day. So we've really benefited from that fractional, really senior expertise so that we can kind of punch above our weight. And we haven't done a lot of the outsourcing kind of overseas. We tried a little bit of that early on. That hasn't been the success of our experience, but a lot of taking advantage of people employees across Canada and the US and that fractional support and taking advantage of the benefits that, especially now it's a real differentiator to stay dedicated to being remote. So many companies that have hybrid environments they see the clock ticking that one day a week in the office, now two days in the week in the office, now three days in the office and you know they don't trust that a hybrid environment is going to actually stay hybrid, whereas we're like, no, we're committed 100% to staying remote.
Julie: 20:44
Well, and I would think that, at the size of company that you're at, the advantages to staying remote are that your talent pool is geographically, you know, infinite in theory. Yeah, because that always plum aside. It's always the hardest thing right of finding the right people is, you know, the right person, the right price and all of the things. Yeah, yeah absolutely yeah.
Julie: 21:10
And so why? Why do people like? I mean, we talked about how the flooding that's happening when companies are posting jobs now and you know they're getting thousands of applicants, and so how the assessment tool can really help them both to narrow the field, hire the right people, but also with that retention piece.
Caitlin: 21:33
Yeah. So what's really interesting and most of us, as business owners, we're never taught this, like you would think that this would be common knowledge, but somehow it's a hidden secret there's real science behind performance and retention, and the science is crystal clear. And there's an entire domain of science called industrial organizational psychology. People go to university, they get PhDs in it. It's a category that's been defined as a science. So these are these experts that really, in the last 30 years, have honed the craft, and there's a set of best practices and a set of conclusions that are really undisputable at this point. And it's that when you line up a hundred people and that are all doing the same job and you look at what makes a top performer different than an average and below average performer, it's never where did they go to school, it's never what past experience they have. Those things are helpful to know. If they can do the job, like if you hired them today, can they tomorrow go ahead and punch that widget, you know, um.
Caitlin: 22:41
But if you look at a hundred people similar background, similar experience and you want to understand what's going to make somebody outperform their peers and what's going to make somebody stay in their job longer, it is behavior. It is those innate talents we call them durable skills. They're going to endure and stay durable throughout their entire career, no matter how their job descriptions change. It is the thing that makes people jump out of the bed in the morning, loving the job that they do, high-fiving their family, at the end of the day, saying I had the best day. It is the thing that allows us to, you know, win the race in our lane over our peers, because it comes naturally, it's easy and we enjoy it. And, on the flip side, we all have things that drain us, and if we're in roles that are constantly asking us to do the things that take me three times longer to do than you, then I'm going to not perform as best and I'm going to feel drained and burnt out and I'm going to leave that job. So it's it's the behavioral alignment between what are my natural behaviors and what are the behaviors that my job requires, and if they're aligned, then I'm going to outperform my peers and I'm going to love my job and I'm going to stay longer. And so that that those measuring of durable skills for the person in the role and matching them together, that is four times more accurate than a resume, that past experience in education at predicting on the job success and performance.
Caitlin: 24:06
The issue is is that 20 years ago, 10 years ago, to access that kind of data on an individual sucked? It was really expensive on the employer. It was a horrible experience on the employee or the candidate Like it. It just, yes, that was best practices, but it wasn't something that we could access without hiring a professional and then coming in with their decoder ring and interpreting all the results. So that's why we started Plum to say, hey, what about if we took this best in class science but then flipped it on its head so that the individual, the job seeker, the employee, would love going through a 20, 25 minute assessment and getting their own profile, their own report when they're done and developing that self-awareness on what makes them exceptional. And then they're simply sharing that data with an employer. And then the employer has the ability to say this is great, but like, what's job relevant, what matters to me, and match that to the behaviors that predict success in their unique job.
Caitlin: 25:08
And so the idea was this is a data problem and in an ideal world you want as many people because it's statistics. If you have a hundred people, then the chances of you having people that are above an 80% match. Maybe out of a hundred you've got 20 to choose from, but of the 20, how many can hit the ground running or meet your salary requirements or meet whatever other information you have? So if you have thousands of applicants, the chances of you screening in those diamonds in the rough that also have the other things you need is amazing. And so, all of a sudden, the problem that everyone's facing where they're getting spammed with people is actually now a benefit, because we have this layer of data that you use right at the beginning to simply say, statistically, who's most likely long-term to be the best investment.
Caitlin: 25:58
And I'm going to start at the top and work my way down. Look at the other information and now, before the interview, before I get kind of conned in the most assertive interviewers with the most outgoing that tend to perform better in the interview but not necessarily on the job, I now have this unbiased data that allows me to see if they're a good fit, so that I'm only interviewing the people that, statistically, are likely to work out. And this is more important than ever because Gen AI is allowing every job seeker to sign up for a service like Lazy Apply and a candidate can apply to 5,000 jobs in their sleep and so you get. You know keyword stuffing in their resume and you know ATSs applicant tracking systems that are keyword scraping and eliminating people and you have this race to the bottom where it's bot against bot, keywords against keywords, and everybody's just overwhelmed and the system's practically bankrupt.
Caitlin: 26:53
So Plum can come in and be that filter based on what really matters, which is do you need an innovative person for your job that's good at working on teams and getting the job done and completing tasks? Great? Here's your 98 match that, no matter what they've done in their career, that's what gets them out of bed in the morning. That was me. That's what makes them exceptional. And, by the way, you, as a job seeker and employee, you may not have realized that you were so good at conflict resolution because it comes so naturally to you. You didn't. You forgot to even mention that. That was a superpower. It's really exceptional. You should talk about that and look for jobs that need that.
Julie: 27:31
Well, and it's so interesting that at this point in the timeline, that the changes in the technology environment, with generative AI and all of the things that are happening, have made you more relevant than ever.
Caitlin: 27:44
It has been really amazing. The interesting thing that's happening in the market is that people are moving into this era of skills-based hiring and skills-based employee development, but they still think that skills means do they know Excel? Do they know you know Python, do they like? It's still just coming back to those keywords, and so there's still a huge job to educate the market that you know those type of skills like Excel and Python. You know those skills really are. You know the shelf life of them, the relevance of them is shrinking so quickly because-.
Julie: 28:26
They're becoming commoditized.
Caitlin: 28:28
Exactly so. They're really becoming perishable skills. The hard skills we've all talked about really should be rebranded to perishable skills because their relevance is really diminishing. But the durable skills, like somebody's ability to innovate, communicate really should be rebranded to perishable skills because their relevance is really diminishing. But the durable skills like somebody's ability to innovate, communicate, execute those durable skills are what predicts performance. It's what's necessary, but people just don't know that they can measure those and that they can use that as their very first filter top of the funnel to shortlist who they should then take their human time to go through and evaluate and consider.
Caitlin: 28:59
And when you change the process to looking at potential first, what happens is you end up screening in people that don't have as high of salary expectations because they haven't been doing it for 20 years. You have people that are going to learn quickly on the job and value the fact that you took a chance on them, and that means that you're also getting a bit of a discount and this increased loyalty. So there's huge opportunities to go after diamonds in the rough that no one else is looking at and you're going to get a top performer, probably at less cost, and they're going to stay and be loyal and truly enjoy their job, like it's really a win win for all parties and it's just a matter of educating people that there is a different way to do things and it's it's hard to change the status quo.
Julie: 29:50
Yes, and so that's been really the uphill climb for you in getting people to adopt. But with that said, how many countries did you say you're in, a lot?
Caitlin: 29:59
147.
Caitlin: 30:01
Yeah, yeah it, uh, it has. It's been amazing. We have about 50,000 people a month that complete their plum profile. It's completely free for individuals so they can go right off to plumio and complete their own plum profile and share it on LinkedIn. We have people by the minute saying you know, these are my top talents. Thank you for the opportunity to be seen not just based on what I've done historically, but based on what I could do if given the opportunity. So it is pretty powerful and amazing.
Caitlin: 30:32
And we, you know we work with really big global enterprise companies like Whirlpool and Citibank and Scotiabank, but we also still work with SMBs and mid-market. That you know. You know that that critical hire is going to be what makes or breaks them. Or they're just now thinking about internal mobility or succession planning and by getting it right, they're not going to, you know, accidentally hire their best sales rep to be their sales leader and then all of a sudden lose a great quota carrying person because they weren't a great people leader. Like being able to provide that. De-risking the statistics of the success of what they're going to do next is so critical. We started with small, medium-sized businesses because those are the make or break moves, but it's been very rewarding to move into these global recognized enterprise companies and truly help them with the scale that we uniquely can do. So it's been very rewarding.
Julie: 31:28
And so what's next? What's next on your path to world domination?
Caitlin: 31:32
Partnerships has been kind of the next chapter, which is, I feel like, again, a whole new muscle, a whole new playbook kind of the next chapter which is, I feel like, again a whole new muscle, a whole new playbook, whole new opportunity to grow. Um, we've been really, really lucky to integrate with um with the systems of record that other companies use, so SAP, success factors or workday or ISIMs or Paylocityity is a new one that we have a full integration with, and what's great with that is that you can go to market together. You can go to their customer base. You can talk about the one plus one equals three. You can do joint events together and so, instead of paying a certain amount of marketing dollars to go to an event, you can pay a lot less and go to a partnership event and talk to their customers and do joint things together and so getting to the place where you know, when you're not known, those big guys won't really engage and they have so many partners they won't prioritize you. But we've been really good at growing our brand and showing that we're different and we're differentiated and we have marketing that really stands out, that now they want to partner with us because they want to be part of collaborating with our really innovative marketing and so it's been the right time over the last year and a half to really kind of do partnerships.
Caitlin: 32:53
We tried doing it before COVID, like the year before COVID, and it was too early. So much of this is it has to be stage appropriate, so you get this really good advice. So I can be like partnerships are so great, but if you do them too early you don't have the necessary means to make them successful. So half of the battle of being a CEO is like this is all really great advice, but how do you get the right order of operations, the right timing? And I think we finally nailed the right timing on partnerships and I'm excited to see that continue to blossom. And there's some really really exciting ones that we're right on the cusp with and others really great success stories of customers we've gone together with which are really cool, and there's a range. There's technology partners, but there's also consulting services that are really taking care of the change management. But that's just kind of getting in front of existing partners. Customers is really the thing we're focused on at the moment.
Julie: 33:52
Yeah, and you've cut your own teeth on some of the big global companies, so entering the partnership pool. You're not new. You're not a new player, you're just coming in a new way. Yes, exactly.
Caitlin: 34:03
Yeah, and they don't have to worry that we're all of a sudden going to be swallowed up by their largest customers. We can be like, no, we can handle those. And it's interesting Like most companies wait until they've kind of dominated and have the majority of their revenue coming from SMBs or mid-market before going to enterprise. But we kind of accidentally started getting some enterprise customers and being able to beat out our competition, some legacy providers and they came back to us and said you know, caitlin, that's great that you can help us with hiring, but what about our existing employees? Can you help us? We have a reorg or we have a succession planning or we have an upskilling initiative that we're doing. And in 2018, we had three enterprise companies all at the same time say can we shoehorn your product for talent management? And like any good entrepreneur, I was like, yes, of course we can do that. And so we ran three pilots, each talent management, different use cases, and they all came back and said I never would have promoted these people, I never would have identified them, like we were screening in the diamonds in the rough inside our own company, and this delivered results we never could have done without Plum. So that's what actually led us to in 2019, raising the $5 million from Real Ventures, led by Real Ventures, and that's what made us go out and build our product for enterprise and the full lifecycle talent acquisition and talent management and launched that in early 2021.
Caitlin: 35:25
So once we were in enterprise, we're like we have to focus all our effort, all of our product development. Integrations matter in a different way when you're at that size. So it just really pulled the focus. Um, even though we serve the smaller customers, it it really narrowed our focus in terms of how to make decisions and who are we building for and who are we targeting. But it's been a journey of whale hunting when you are, when it feels like you're in a canoe and you're whale hunting and it's amazing when um like that, we can do it.
Caitlin: 36:00
But that has been an entire kind of learning curve in itself is it's you have to be very, very, very brave and and it requires again, like VC money we we raised uh, 8 million Canadian was the last round we did. There's a little bit in between led by Pearson Ventures, the textbook publishing company. They have a big future of work mandate and they really saw this kind of human first vision of the future and individuals having control of their data and really guiding their own careers, and so they led our last round and it's amazing to kind of be on this journey, but to go after the go-to-market strategy for enterprise is so much more costly and is is a big lift. And so you know, we're grateful that we had the VC money in order to do it, but it definitely feels that we've taken some of the paths less less normally gone. Normally, enterprise comes much later. So you have this base to kind of weather the storm. But we were like all in on enterprise and whale hunting and it's not for the faint of heart.
Julie: 37:07
No, and how is Caitlin, the sales CEO, these days still selling?
Caitlin: 37:13
Still selling. I feel at my best when I am able to be. I don't need to be in every meeting by any means, but I find that if I step back too much because what's interesting is in 2022, I would say we had this unbelievable product market fit. It felt like magic. People in the startup world talk about product market fit all the time, and the way I've kind of defined it is that if you talk to 10 customers, you know how many of them instantly go. You're solving my problem. Nobody else is like I needed this yesterday.
Caitlin: 37:49
Yes, yes, yes, and I remember, you know, for a long time, because people don't know that this exists. It felt like if we talked to 10 people, four would be interested and maybe two would buy, and so it just felt like you're constantly pushing a boulder uphill. And in 2022, everything just finally clicked All the changes bringing in a chief revenue officer that brought in a bunch of changes. Everything just started to click and if we talked to 10 people, it's like eight, you know, eight to nine would say yes and seven to eight would go forward and pay, and it just was like this incredible thing. But most enterprise companies at least, and I think a lot of the industry stopped hiring last year in 2024. So overnight our product didn't change. The product part of Product Market Fit didn't change. The product part of product market fit didn't change, the market changed. And so to be involved in sales and to constantly be involved, it allows me.
Julie: 38:47
You're sliding back and forth between the product and the sales cycle and what's happening.
Caitlin: 38:53
And it allows to just keep that product market fit that gap as the market changes, to reduce as quickly as possible that gap between the product and the market, as it needs to iterate and change. And that is the advantage of being the CEO is you can. I always want to be aligned with my executive team, but there is an ability to go. Oh, my goodness, okay, everybody turn right because, like we're not getting anything from left right now, we need to go hard right because the market has changed. So last year it was a really hard adjustment. Okay, talent management we need to be all in on talent management. Well, now, in 2025, people are hiring again. We have customers.
Caitlin: 39:32
I just saw on our Slack channel today this customer that loved us that stopped their subscription last year because they were not hiring. They're back, they want to reactivate their account and it's like, oh right, that's what's happened, that we saw that in COVID people stopped their subscriptions and then they came back because they were hiring again. We need to go back to our past customers and run and run a campaign because they'll care about us again. They didn't care, they had crises of their own, layoffs of their own last year, but they're going to care again and just being close to it and finding these ways of reengaging.
Caitlin: 40:07
I love that part of my job. I was going through old Zoom recordings of meetings from back in 2021, and I noticed that the meetings I got brought into there were chief people officers on the other end. Well, those chief people officers, if I look at LinkedIn, have moved two times since, and so I'm like, okay, let's divide up these old people that are in new companies that we know in 2025 are now growing. Let's do some account-based marketing out to these key stakeholders that already saw a demo of us in 2022 or 2021, you know when things were going really well and let's re-engage them as a as a human now at a new company.
Caitlin: 40:44
And so I I like solving problems, but if I'm too far away from the customer that I'm, I don't get to solve the customer problems. I work on the operational problems and that's where I'm always going to feel safe. That's always where I'm going to default to. So, by by being with the customers, it constantly allows that to stay top of mind and find new ways to grow and um, so, yeah, I, I'm, I'm, I'm finding new opportunities because the market's changed again.
Julie: 41:15
Yep Well, and it sounds like it's going to be an exciting time ahead for you as you grow the business on to the next level and sign up more enterprise clients and keep growing Plum. Yeah, Thank you so much for joining me. I really appreciate it. It was great talking with you.
Caitlin: 41:33
Thank you for having me.
Julie: 41:34
You're welcome. Take care.
Julie: 41:36
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