February 20, 2025 • 42 mins
Julie's Big Gorgeous Goals: Official Workbook is here! Order your copy today.
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.
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.
You can learn more about Plum on their website.
You can also connect with Caitlin on LinkedIn or Instagram.
You can connect with Julie on LinkedIn or Instagram.
Find Julie's writing at her blog or by ordering her book Big Gorgeous Goals and the brand new official companion workbook!
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Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Julie (00:04):
Welcome to Figure Eight, where we feature inspiring
stories of women entrepreneurswho have grown their businesses
to seven and eight figuresrevenue.
If you're in the mix of growinga bigger business, these
stories are for you.
Join us as we explore where thetough spots are, how to
overcome them and how to prepareyourself for the next portion
(00:27):
of the climb.
I'm your host, julie Ellis.
I'm an author, entrepreneur anda growth and leadership coach
who co-founded, grew and exitedan eight-figure business.
This led me to exploring whysome women achieve great things,
and that led to my book Big,gorgeous Goals.
(00:47):
Let's explore the systems,processes and people that help
us grow our businesses to newheights.
If you're interested in growingyour business, this podcast
will help.
Now let's get going.
Hello and welcome to thisepisode of Figure 8.
Today, I am joined by CaitlinMacGregor.
(01:09):
Caitlin is the CEO andco-founder of Plum, and she's
passionate about helping peoplereach their full potential.
So she built businesses two ofthem for other people and then
she founded Plum, which helpsorganizations fully leverage the
human potential within theirworkforce.
It equips business leaders withthe talent data needed to match
(01:31):
employees' talent to the roleswhere they'll thrive, so that
businesses can thrive too.
And you may have read aboutPlum.
They've been in lots of newsmedia, in the New York Times and
the Globe and Mail and globalTV all over the place, and I'm
so thrilled to have you heretoday.
Welcome, caitlin.
Caitlin (01:48):
Thank you so much for having me.
I'm really excited for thisconversation.
Julie (01:51):
Yeah, I'm excited too and I love sort of like homegrown
story, and female entrepreneursobviously are my thing and I'm
so glad to have you here becauseI think it's so interesting.
You know the technology companythat you founded and sort of
what your why was.
What can you tell me about youknow what gave you the
(02:12):
inspiration to start Plum?
Caitlin (02:16):
Selfishly.
I needed Plum in order to be asuccessful CEO.
First and foremost, it startedout of I was my first customer
and I saw the value firsthand.
And then it's grown over timeto now my why is really my kids.
And I'll take a step back andkind of explain how we got here.
(02:38):
But, yes, at the end of the day, the story still came back to I
couldn't do my job unless I hadthis data.
So I had built two businessesfor other people before starting
Plum and the second business Iwas hired by a Canadian
educational technology companyto go down to New Hampshire and
start up and run the US branch.
(02:59):
And my executive coach at thetime said Caitlin, if you screw
up that first hire, it'll be aloss of $300,000 on the business
.
So, not wanting to make thatmistake, I ended up using this
(03:22):
psychometric assessment, thisbehavioral.
I was able to use thisassessment on every single
applicant that applied for thejob and we had 80 people apply
for the job and two candidatesstood out for totally different
reasons.
One was this guy who wasperfect on paper.
He had a master's in education,five years of relevant work
experience.
My CEO back in Canada wasdrooling.
(03:43):
This was the golden boy byevery measure, but the
assessment showed that he had amediocre work ethic.
But he was hired anyway.
And then we had this otherperson and she scored in the top
third percentile of the entireworkforce for overall
productivity, and my executivecoach said that statistically
she was one in a thousand andI'd be an idiot not to hire her.
So I ran an experiment andhired the guy that was perfect
(04:04):
on paper and the woman that hadthe highest assessment scores,
and three months later the guy'sfancy football team was doing
really well, but he was onlydoing 10% of his work.
So he was let go, and the womanwas doing not only all of his
work and hers, but within a yearand a half she had replaced me
as acting president while I wenton maternity leave.
And the punchline is is thatshe had two art degrees, her
(04:25):
only work experience had beenseven years of waitressing and
she didn't even know how to useExcel.
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 thebusiness over three years I just
kept screening in theseincredible diamonds in the rough
.
The next hire was this highschool student that we wanted to
(04:47):
hire 20 hours a week to do oursocial media and our new website
, and he was literallyoutperforming people that were
making over a hundred thousanddollars, and he's since gone on
and founded his own companies.
And the next person had droppedout of college to literally
join the circus.
So we hired an ex-Carney bestcustomer success manager, no
tech experience prior, and wecould just see these incredibly
(05:11):
loyal people that were so drivenwere top performers, and
there's no way, without thisdata, I would have ever selected
them out of piles of resumes.
So I had already built twobusinesses for other people.
I just started my family andreally wanted to come back to
Canada, and as an entrepreneur,you know like I'm just a gap
(05:34):
closer.
I see a problem and I want toclose that gap, and it didn't
matter if I was working forsomebody else or if I was doing
it myself.
I was going to be working thecrazy long hours and solving
problems no matter what, and sothere was an opportunity to say,
hey, if I'm going to put in theblood, sweat and tears.
I might as well this time, doit for myself and my co-founder,
who's my husband.
(05:55):
We had been working together atthe ed tech company.
He was the expert in thesoftware and he's the one that
got me the job.
And so we moved down to NewHampshire and ran that business
for three years together and wealso realized that we worked
better together than not, and,being an entrepreneur, you know
the sacrifices, you know thelong hours, and it's much easier
(06:16):
if somebody has the same kindof understanding of your whole
life and commitment and thetrade-offs.
And so we had loved workingtogether for those three years
and wanted to come back toCanada because we had started a
family, and so we're like weshould do this for ourselves, we
should run our own business.
And he came back from work youknow I was two weeks overdue to
give labor and he's like I'vegot the idea.
(06:38):
Let's take this consultingservice, let's take it out of
the hands of these reallyexpensive consultants and let's
turn it into software as aservice.
Let's democratize access to itso that every single person and
every single role can be matchedbased on this data.
That, based in industrialorganizational psychology, is
(06:58):
four times more accurate than aresume at predicting on the job
success.
And so we started it because Icould never imagine successfully
running our business orsomebody else's business without
this data.
It's like putting a pair ofglasses on.
And so I was like I'm not goingto be successful unless I have
this.
So I might as well go and buildsomething that really, at that
(07:19):
time, didn't exist as a software.
And then now you know, our kidsare 13 and nine and you know I
don't care when they start theircareer if they're doctors,
lawyers, teachers, nurses.
I just want them to be happyand fulfilled.
And when I look at thelandscape for how people get
matched to roles, there isn't asolution out there.
(07:41):
And so we we kept going withPlum because we imagined a world
like LinkedIn.
Instead of it saying whatyou've done historically, it
talks about what you could do ifgiven the opportunity, and can
really reveal to people whatdrives them and gives them a
sense of self-worth and helpsthem match to jobs where they're
going to flourish, because webelieve that when people
(08:02):
flourish, businesses thrive.
Julie (08:04):
So 13 years.
Your oldest is 13.
So you're basically coming upto that 13 year mark now and
obviously building any kind ofsoftware product is a long and
expensive road to go down.
I know you've raised money overtime.
What has that been like for you?
Caitlin (08:24):
Yeah, I've raised 19 million Canadian to date.
It's been a groundbreakingjourney.
There's very few women CEOs inCanada that have raised that
amount of capital.
I remember that when I went toraise I had raised 2 million of
(08:44):
angel capital.
So a lot of $25,000 checks at atime, a few more, a few that
were a bit more, but a lot ofindividual people that were
business owners themselves thatbelieved in what we were doing
and it took two years to raisethat first 2 million.
And I had my second kid in themiddle of that.
I literally fundraised pregnant.
(09:05):
Surprisingly, nobody gave memoney while I was pregnant.
But two months after givingbirth to my second I was on
stage in Buffalo at a pitchcompetition where we won
$250,000 US and then we had awhole 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 2million, but that was all angel
(09:27):
money.
When I went to raise my firstround from Venture Capitalists,
it was a really interestingexperience because I remember at
the time when I started, bdc'sreport 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 inthat 2 million in two years.
(09:49):
So I wanted to be the firstwoman to raise 5 million in one
go.
By the time I did, I thinkthere were about three other
women that had done it by thatpoint, so it wasn't the first,
which was, you know, the morethe merrier more of us need
capital, but it was, and Ididn't have the Rolodex.
(10:10):
I'm in Waterloo, ontario,really amazing tech ecosystem,
but a lot of bootstrappedcompanies, not a huge investor
community.
There's a good angel community,but we don't have a lot of
venture capitals, or at leasteight years ago we didn't have a
lot of those venturecapitalists here.
(10:31):
And so what I found is that mynetwork I wasn't one degree away
from the check writers, and soit took me about two years to
just build up my Rolodex, sothat I eventually went through a
hundred no's before I got totwo yeses.
(10:52):
And then, as I was down to twoterm sheets, one out of New York
City and then one out ofToronto, slash Montreal it
really came down to do I have aninvestor that I really can see
being a partner with?
Do I really believe that theyhave my back and that we are
(11:12):
aligned, because if we're notaligned, eventually things are
going to get tough and they'renot going to be there.
And I was really, really luckythat Real Ventures, which is
based out of Montreal but hasoffice in Toronto they were on
their own transformation andtheir own journey, where they
were really believing ininvesting in the potential of
(11:36):
businesses that were trying tohave the impact on that had
purpose basically companies thatwere trying to do more than
just make money, that theywanted to have a positive impact
on the world.
And you know, this was reallyabout how do we give everybody
the opportunity, regardless oftheir background, regardless of
(11:56):
their experience, to really bein a career that allows them to
be happy, fulfilled and thrive?
So they really believed in thevision and at the time, janet
Bannister came in as my leadinvestor and it was amazing to
have a woman VC on my board andto nurture that relationship.
(12:16):
And what?
Years later, I can look backand say every time that it was
one of those forks in the roadwhere we had lots of potential
but not necessarily enough prooffor everybody to jump on board
and say, okay, I'm going to fundthe next round.
Real Ventures and Janet werealways there for us, just always
there, and if there ever wasmisalignment, there was the work
(12:39):
that was needed to find thealignment and it ended up being
a really positive experience.
But when you start on thehamster wheel of relying on
outside capital in order to runyour business and I just said I
spent two years raising 2million I spent two years, you
know, building my Rolodex I, youknow, got a hundred no's.
(13:01):
Well, in the process of raising, you know, 19 million, I've
probably had 400 no's, maybe 500no's at this point.
So there's kind of two thingsthat I've learned from this.
Besides the positive parts oflike it's really important to
find an amazing investor thatreally believes in you, is
aligned and I'm very, very, verylucky on so many levels the
(13:24):
things that I've realized is thenumber of hours that I put into
developing that muscle ofbecoming good and successful at
fundraising.
I really wish in hindsight I hadput those hours into learning
how to be the best sales CEOever.
I'm a really strong operationalCEO.
I've obviously had successfundraising in the grand scheme
(13:46):
of line me up against otherCanadians, but I wish that I had
developed instead of learninghow to pitch decks instead of
learning how to do a pitchcompetition instead of talking
to VCs.
I wish all those hours ofgetting good at that I had spent
learning how to be the bestsales leader, and that's been a
(14:07):
journey that I've really had theprivilege to be able to do,
thanks to partnering with mychief revenue officer, who had
that skill set and really wasable to mentor me and coach me
and do that peer learning whereI'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, whatwould that have been like if I'd
(14:28):
been doing it for the last 13years?
So I feel like celebrating thesuccess of the investing is
sometimes setting the wrongmessage to what does success
actually mean as being anentrepreneur?
And I think the amount of moneythat you've raised can be a
misleading indicator.
(14:49):
And the other part is that Itruly believe and there's lots
of research to support this Ithink the whole funding um
market has changed in the lasttwo years.
The idea that Reid Hoffman putout the book blitz scaling was
that an investor would put in $1and they get $2 return.
That was because valuations,you know, to $5 million in
(15:14):
revenue, you could maybe exitfor $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 wasgrowing my business, when they
got to $7 million Canadian, theyhad exits that were $100,000,
$120,000, $150,000.
That's amazing In this day andage.
Those companies now would begetting three or four, maybe
(15:38):
five X of valuation.
The math is totally different.
So they're maybe getting $35million today versus when they
did this $100 million that theygot five years ago.
Exactly so the rule book, theplaybook that I grew up on, the
playbook for really the firstdecade of running this business.
That playbook now is in thegarbage and has been lit on fire
(16:00):
and I don't think it's evercoming back.
So it's really, really, reallyimportant for people that are
starting their entrepreneurialjourney to go.
Wait a second is that actuallythe right playbook?
Is that the right risk reward?
Is that the right way ofrunning a business?
And so it is.
(16:21):
With technology at the time,developers are really expensive,
Infrastructure is reallyexpensive.
I knew I could not build thisbusiness unless it had outside
capital, and that was the goalfrom I'd already started
businesses that werebootstrapped from other people.
I wanted this to be VC backed,but now, with generative AI, I
mean it is amazing how companiesdon't need to just keep adding
(16:44):
bodies in order to grow.
There's other ways to grow andscale, and I mentor through Real
Ventures.
They have a really amazingmentorship program and I have
the ability to mentor two peoplethat are early, and each of
these teams are two people, fourpeople, and my advice is don't
spend a lot of time fundraising.
(17:05):
If they're throwing money atyou and one of them was it's
like OK, that's great, but makesure you have alignment.
But if they're coming to you,that's a different thing.
But don't waste your time goingout.
And then the other thing is isdon't just take that money and
automatically start hiring abunch of people Like what are
the roles and responsibilitiesthat aren't getting taken care
of?
Is that more important?
(17:26):
What's the order of operations?
Is that going to drive morerevenue and is that just more
generative AI, or is that anoutsourced virtual assistant?
There are more ways of solvingit that are less expensive than
how I was running the businessin the first decade, and so
there's an opportunity, I think,to do things differently than
(17:51):
the playbook that I use to buildthis company.
Julie (17:53):
I think it's one of the really interesting things I'm
seeing with entrepreneurs rightnow is sort of smaller core
teams.
Lots of things are sort ofoutsourced or third party or
automated, where you know, wewere 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 inCOVID and when it doesn't work,
it's because not enoughresources have been put into how
to make that environmentsuccessful.
And when you're low onresources and cash, it's one of
(18:29):
the first things that getssacrificed.
So it's not easy, but I thinkthere are so many benefits, um,
from being fully remote.
I benefited from the fact thatI had a core team that had years
of working together in person.
So, as the nature of our youknow, team shifts and we get
more and more of just remotepeople, you know I'm I'm
(18:50):
reevaluating all the pros andcons, but it can be a really big
unlock to to stay remote, causeyou, you have a lots of
possibilities.
And then the other thing we'vedone is take advantage of
fractional services.
So we moved up market toenterprise four years ago and so
we needed a chief security andcompliance officer.
I can't.
I can't afford that personfull-time and I don't have
(19:13):
enough enterprise customers tokeep that person busy full,
full-time.
We drink our own champagne.
So, even though we can have afull-time HR person, you really
want somebody who's at theforefront of strategy and
thinking about thingsdifferently and really
rethinking about work on aregular cadence.
Who also is seeing how otherbusinesses are changing?
(19:36):
So we have a fractional chiefpeople officer.
My CFO is on mat leave, so wehave a fractional CFO while our
manager of finance can run theday-to-day.
So we've really benefited fromthat fractional, really senior
expertise so that we can kind ofpunch above our weight.
(19:56):
And we haven't done a lot ofthe outsourcing kind of overseas
.
We tried a little bit of thatearly on.
That hasn't been the success ofour experience, but a lot of
taking advantage of peopleemployees across Canada and the
US and that fractional supportand taking advantage of the
(20:17):
benefits that, especially nowit's a real differentiator to
stay dedicated to being remote.
So many companies that havehybrid environments they see the
clock ticking that one day aweek in the office, now two days
in the week in the office, nowthree days in the office and you
know they don't trust that ahybrid environment is going to
(20:37):
actually stay hybrid, whereaswe'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 advantagesto staying remote are that your
talent pool is geographically,you know, infinite in theory.
Yeah, because that always plumaside.
It's always the hardest thingright of finding the right
people is, you know, the rightperson, the right price and all
(21:06):
of the things.
Yeah, yeah absolutely yeah.
And so why?
Why do people like?
I mean, we talked about how theflooding that's happening when
companies are posting jobs nowand you know they're getting
thousands of applicants, and sohow the assessment tool can
really help them both to narrowthe field, hire the right people
(21:30):
, but also with that retentionpiece.
Caitlin (21:33):
Yeah.
So what's really interestingand most of us, as business
owners, we're never taught this,like you would think that this
would be common knowledge, butsomehow it's a hidden secret
there's real science behindperformance and retention, and
the science is crystal clear.
And there's an entire domain ofscience called industrial
(21:54):
organizational psychology.
People go to university, theyget PhDs in it.
It's a category that's beendefined as a science.
So these are these experts thatreally, in the last 30 years,
have honed the craft, andthere's a set of best practices
and a set of conclusions thatare really undisputable at this
point.
And it's that when you line upa hundred people and that are
(22:18):
all doing the same job and youlook at what makes a top
performer different than anaverage and below average
performer, it's never where didthey go to school, it's never
what past experience they have.
Those things are helpful toknow.
If they can do the job, like ifyou hired them today, can they
tomorrow go ahead and punch thatwidget, you know, um.
(22:41):
But if you look at a hundredpeople similar background,
similar experience and you wantto understand what's going to
make somebody outperform theirpeers and what's going to make
somebody stay in their joblonger, it is behavior.
It is those innate talents wecall them durable skills.
They're going to endure andstay durable throughout their
(23:04):
entire career, no matter howtheir job descriptions change.
It is the thing that makespeople jump out of the bed in
the morning, loving the job thatthey do, high-fiving their
family, at the end of the day,saying I had the best day.
It is the thing that allows usto, you know, win the race in
our lane over our peers, becauseit comes naturally, it's easy
(23:25):
and we enjoy it.
And, on the flip side, we allhave things that drain us, and
if we're in roles that areconstantly asking us to do the
things that take me three timeslonger to do than you, then I'm
going to not perform as best andI'm going to feel drained and
burnt out and I'm going to leavethat job.
So it's it's the behavioralalignment between what are my
natural behaviors and what arethe behaviors that my job
(23:46):
requires, and if they're aligned, then I'm going to outperform
my peers and I'm going to lovemy job and I'm going to stay
longer.
And so that that thosemeasuring of durable skills for
the person in the role andmatching them together, that is
four times more accurate than aresume, that past experience in
education at predicting on thejob success and performance.
The issue is is that 20 yearsago, 10 years ago, to access
(24:12):
that kind of data on anindividual sucked?
It was really expensive on theemployer.
It was a horrible experience onthe employee or the candidate
Like it.
It just, yes, that was bestpractices, but it wasn't
something that we could accesswithout hiring a professional
and then coming in with theirdecoder ring and interpreting
all the results.
So that's why we started Plumto say, hey, what about if we
(24:35):
took this best in class sciencebut then flipped it on its head
so that the individual, the jobseeker, the employee, would love
going through a 20, 25 minuteassessment and getting their own
profile, their own report whenthey're done and developing that
self-awareness on what makesthem exceptional.
(24:55):
And then they're simply sharingthat data with an employer.
And then the employer has theability to say this is great,
but like, what's job relevant,what matters to me, and match
that to the behaviors thatpredict success in their unique
job.
And so the idea was this is adata problem and in an ideal
world you want as many peoplebecause it's statistics.
(25:16):
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'vegot 20 to choose from, but of
the 20, how many can hit theground running or meet your
salary requirements or meetwhatever other information you
have?
So if you have thousands ofapplicants, the chances of you
(25:36):
screening in those diamonds inthe rough that also have the
other things you need is amazing.
And so, all of a sudden, theproblem that everyone's facing
where they're getting spammedwith people is actually now a
benefit, because we have thislayer of data that you use right
at the beginning to simply say,statistically, who's most
likely long-term to be the bestinvestment.
(25:58):
And I'm going to start at thetop and work my way down.
Look at the other informationand now, before the interview,
before I get kind of conned inthe most assertive interviewers
with the most outgoing that tendto perform better in the
interview but not necessarily onthe job, I now have this
unbiased data that allows me tosee if they're a good fit, so
(26:19):
that I'm only interviewing thepeople that, statistically, are
likely to work out.
And this is more important thanever because Gen AI is allowing
every job seeker to sign up fora service like Lazy Apply and a
candidate can apply to 5,000jobs in their sleep and so you
get.
You know keyword stuffing intheir resume and you know ATSs
(26:40):
applicant tracking systems thatare keyword scraping and
eliminating people and you havethis race to the bottom where
it's bot against bot, keywordsagainst keywords, and
everybody's just overwhelmed andthe system's practically
bankrupt.
So Plum can come in and be thatfilter based on what really
matters, which is do you need aninnovative person for your job
(27:02):
that's good at working on teamsand getting the job done and
completing tasks?
Great?
Here's your 98 match that, nomatter what they've done in
their career, that's what getsthem out of bed in the morning.
That was me.
That's what makes themexceptional.
And, by the way, you, as a jobseeker and employee, you may not
have realized that you were sogood at conflict resolution
because it comes so naturally toyou.
(27:22):
You didn't.
You forgot to even mention that.
That was a superpower.
It's really exceptional.
You should talk about that andlook for jobs that need that.
Julie (27:31):
Well, and it's so interesting that at this point
in the timeline, that thechanges in the technology
environment, with generative AIand all of the things that are
happening, have made you morerelevant than ever.
Caitlin (27:44):
It has been really amazing.
The interesting thing that'shappening in the market is that
people are moving into this eraof skills-based hiring and
skills-based employeedevelopment, but they still
think that skills means do theyknow Excel?
Do they know you know Python,do they like?
(28:05):
It's still just coming back tothose keywords, and so there's
still a huge job to educate themarket that you know those type
of skills like Excel and Python.
You know those skills reallyare.
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 becomingperishable skills.
The hard skills we've alltalked about really should be
rebranded to perishable skillsbecause their relevance is
really diminishing.
But the durable skills, likesomebody's ability to innovate,
communicate really should berebranded to perishable skills
because their relevance isreally diminishing.
But the durable skills likesomebody's ability to innovate,
communicate, execute thosedurable skills are what predicts
performance.
It's what's necessary, butpeople just don't know that they
(28:49):
can measure those and that theycan use that as their very
first filter top of the funnelto shortlist who they should
then take their human time to gothrough and evaluate and
consider.
And when you change the processto looking at potential first,
what happens is you end upscreening in people that don't
have as high of salaryexpectations because they
(29:10):
haven't been doing it for 20years.
You have people that are goingto learn quickly on the job and
value the fact that you took achance on them, and that means
that you're also getting a bitof a discount and this increased
loyalty.
So there's huge opportunitiesto go after diamonds in the
rough that no one else islooking at and you're going to
(29:31):
get a top performer, probably atless cost, and they're going to
stay and be loyal and trulyenjoy their job, like it's
really a win win for all partiesand it's just a matter of
educating people that there is adifferent way to do things and
it's it's hard to change thestatus 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 manycountries did you say you're in,
a lot?
Caitlin (29:59):
147.
Yeah, yeah it, uh, it has.
It's been amazing.
We have about 50,000 people amonth that complete their plum
profile.
It's completely free forindividuals so they can go right
off to plumio and completetheir own plum profile and share
it on LinkedIn.
We have people by the minutesaying you know, these are my
(30:20):
top talents.
Thank you for the opportunityto be seen not just based on
what I've done historically, butbased on what I could do if
given the opportunity.
So it is pretty powerful andamazing.
And we, you know we work withreally big global enterprise
companies like Whirlpool andCitibank and Scotiabank, but we
also still work with SMBs andmid-market.
(30:42):
That you know.
You know that that criticalhire is going to be what makes
or breaks them.
Or they're just now thinkingabout internal mobility or
succession planning and bygetting it right, they're not
going to, you know, accidentallyhire their best sales rep to be
their sales leader and then allof a sudden lose a great quota
carrying person because theyweren't a great people leader.
(31:04):
Like being able to provide that.
De-risking the statistics ofthe 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 breakmoves, but it's been very
rewarding to move into theseglobal recognized enterprise
companies and truly help themwith the scale that we uniquely
(31:25):
can do.
So it's been very rewarding.
Julie (31:28):
And so what's next?
What's next on your path toworld domination?
Caitlin (31:32):
Partnerships has been kind of the next chapter, which
is, I feel like, again, a wholenew muscle, a whole new playbook
kind of the next chapter whichis, I feel like, again a whole
new muscle, a whole new playbook, whole new opportunity to grow.
Um, we've been really, reallylucky to integrate with um with
the systems of record that othercompanies use, so SAP, success
(31:53):
factors or workday or ISIMs orPaylocityity is a new one that
we have a full integration with,and what's great with that is
that you can go to markettogether.
You can go to their customerbase.
You can talk about the one plusone equals three.
You can do joint eventstogether and so, instead of
paying a certain amount ofmarketing dollars to go to an
(32:14):
event, you can pay a lot lessand go to a partnership event
and talk to their customers anddo joint things together and so
getting to the place where youknow, when you're not known,
those big guys won't reallyengage and they have so many
partners they won't prioritizeyou.
But we've been really good atgrowing our brand and showing
(32:35):
that we're different and we'redifferentiated and we have
marketing that really stands out, that now they want to partner
with us because they want to bepart of collaborating with our
really innovative marketing andso it's been the right time over
the last year and a half toreally kind of do partnerships.
We tried doing it before COVID,like the year before COVID, and
(32:56):
it was too early.
So much of this is it has to bestage appropriate, so you get
this really good advice.
So I can be like partnershipsare so great, but if you do them
too early you don't have thenecessary means to make them
successful.
So half of the battle of beinga CEO is like this is all really
great advice, but how do youget the right order of
(33:17):
operations, the right timing?
And I think we finally nailedthe right timing on partnerships
and I'm excited to see thatcontinue to blossom.
And there's some really reallyexciting ones that we're right
on the cusp with and othersreally great success stories of
customers we've gone togetherwith which are really cool, and
(33:37):
there's a range.
There's technology partners,but there's also consulting
services that are really takingcare of the change management.
But that's just kind of gettingin front of existing partners.
Customers is really the thingwe'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 enteringthe partnership pool.
You're not new.
You're not a new player, you'rejust 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 swallowedup by their largest customers.
We can be like, no, we canhandle those.
And it's interesting Like mostcompanies wait until they've
kind of dominated and have themajority of their revenue coming
from SMBs or mid-market beforegoing to enterprise.
(34:24):
But we kind of accidentallystarted getting some enterprise
customers and being able to beatout our competition, some
legacy providers and they cameback to us and said you know,
caitlin, that's great that youcan help us with hiring, but
what about our existingemployees?
Can you help us?
We have a reorg or we have asuccession planning or we have
an upskilling initiative thatwe're doing.
And in 2018, we had threeenterprise companies all at the
(34:47):
same time say can we shoehornyour 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 theyall came back and said I never
would have promoted these people, I never would have identified
them, like we were screening inthe diamonds in the rough inside
our own company, and thisdelivered results we never could
(35:07):
have done without Plum.
So that's what actually led usto in 2019, raising the $5
million from Real Ventures, ledby Real Ventures, and that's
what made us go out and buildour product for enterprise and
the full lifecycle talentacquisition and talent
management and launched that inearly 2021.
So once we were in enterprise,we're like we have to focus all
(35:30):
our effort, all of our productdevelopment.
Integrations matter in adifferent way when you're at
that size.
So it just really pulled thefocus.
Um, even though we serve thesmaller customers, it it really
narrowed our focus in terms ofhow to make decisions and who
are we building for and who arewe targeting.
But it's been a journey ofwhale hunting when you are, when
(35:52):
it feels like you're in a canoeand you're whale hunting and
it's amazing when um like that,we can do it.
But that has been an entire kindof learning curve in itself is
it's you have to be very, very,very brave and and it requires
again, like VC money we weraised uh, 8 million Canadian
(36:15):
was the last round we did.
There's a little bit in betweenled by Pearson Ventures, the
textbook publishing company.
They have a big future of workmandate and they really saw this
kind of human first vision ofthe future and individuals
having control of their data andreally guiding their own
careers, and so they led ourlast round and it's amazing to
(36:39):
kind of be on this journey, butto go after the go-to-market
strategy for enterprise is somuch more costly and is is a big
lift.
And so you know, we're gratefulthat we had the VC money in
order to do it, but itdefinitely feels that we've
taken some of the paths lessless normally gone.
Normally, enterprise comes muchlater.
So you have this base to kindof weather the storm.
(37:00):
But we were like all in onenterprise 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 amable to be.
I don't need to be in everymeeting by any means, but I find
that if I step back too muchbecause what's interesting is in
2022, I would say we had thisunbelievable product market fit.
It felt like magic.
(37:33):
People in the startup worldtalk about product market fit
all the time, and the way I'vekind of defined it is that if
you talk to 10 customers, youknow how many of them instantly
go.
You're solving my problem.
Nobody else is like I neededthis yesterday.
Yes, yes, yes, and I remember,you know, for a long time,
because people don't know thatthis exists.
(37:55):
It felt like if we talked to 10people, four would be
interested and maybe two wouldbuy, and so it just felt like
you're constantly pushing aboulder uphill.
And in 2022, everything justfinally clicked All the changes
bringing in a chief revenueofficer that brought in a bunch
of changes.
Everything just started toclick and if we talked to 10
(38:15):
people, it's like eight, youknow, eight to nine would say
yes and seven to eight would goforward and pay, and it just was
like this incredible thing.
But most enterprise companiesat least, and I think a lot of
the industry stopped hiring lastyear in 2024.
So overnight our product didn'tchange.
(38:35):
The product part of ProductMarket Fit didn't change.
The product part of productmarket fit didn't change, the
market changed.
And so to be involved in salesand 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'shappening.
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 productand the market, as it needs to
iterate and change.
And that is the advantage ofbeing the CEO is you can.
I always want to be alignedwith my executive team, but
there is an ability to go.
Oh, my goodness, okay,everybody turn right because,
(39:18):
like we're not getting anythingfrom left right now, we need to
go hard right because the markethas changed.
So last year it was a reallyhard adjustment.
Okay, talent management we needto be all in on talent
management.
Well, now, in 2025, people arehiring again.
We have customers.
I just saw on our Slack channeltoday this customer that loved
us that stopped theirsubscription last year because
they were not hiring.
(39:38):
They're back, they want toreactivate their account and
it's like, oh right, that'swhat's happened, that we saw
that in COVID people stoppedtheir subscriptions and then
they came back because they werehiring again.
We need to go back to our pastcustomers and run and run a
campaign because they'll careabout us again.
They didn't care, they hadcrises of their own, layoffs of
(39:59):
their own last year, but they'regoing to care again and just
being close to it and findingthese ways of reengaging.
I love that part of my job.
I was going through old Zoomrecordings of meetings from back
in 2021, and I noticed that themeetings I got brought into
there were chief people officerson the other end.
Well, those chief peopleofficers, if I look at LinkedIn,
(40:21):
have moved two times since, andso I'm like, okay, let's divide
up these old people that are innew companies that we know in
2025 are now growing.
Let's do some account-basedmarketing out to these key
stakeholders that already saw ademo of us in 2022 or 2021, you
know when things were goingreally well and let's re-engage
(40:41):
them as a as a human now at anew company.
And so I I like solving problems, but if I'm too far away from
the customer that I'm, I don'tget to solve the customer
problems.
I work on the operationalproblems and that's where I'm
always going to feel safe.
That's always where I'm goingto default to.
So, by by being with thecustomers, it constantly allows
(41:02):
that to stay top of mind andfind new ways to grow and um, so
, yeah, I, I'm, I'm, I'm findingnew 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 asyou grow the business on to the
next level and sign up moreenterprise clients and keep
growing Plum.
Yeah, Thank you so much forjoining 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.
I hope you enjoyed today'sepisode.
Please remember to hitsubscribe on your favorite
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Figure Eight isn't just apodcast.
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entrepreneurs coming to life.
If you're interested inlearning more, you can find my
(41:57):
book Big Gorgeous Goals onAmazon, anywhere you might live,
For more about my growth andleadership training programs.
Visit www.
julieellis.
ca to see how we might worktogether.
Read my blog or sign up to getyour free diagnostic.
Are you ready for growth?
(42:18):
Once again, that's www.
julieellis.
ca.
When we work together, we allwin.
See you again soon for anotherepisode of Figure 8.
Welcome to Figure Eight, where we feature inspiring
stories of women entrepreneurswho have grown their businesses
to seven and eight figuresrevenue.
If you're in the mix of growinga bigger business, these
stories are for you.
Join us as we explore where thetough spots are, how to
overcome them and how to prepareyourself for the next portion
(00:27):
of the climb.
I'm your host, julie Ellis.
I'm an author, entrepreneur anda growth and leadership coach
who co-founded, grew and exitedan eight-figure business.
This led me to exploring whysome women achieve great things,
and that led to my book Big,gorgeous Goals.
(00:47):
Let's explore the systems,processes and people that help
us grow our businesses to newheights.
If you're interested in growingyour business, this podcast
will help.
Now let's get going.
Hello and welcome to thisepisode of Figure 8.
Today, I am joined by CaitlinMacGregor.
(01:09):
Caitlin is the CEO andco-founder of Plum, and she's
passionate about helping peoplereach their full potential.
So she built businesses two ofthem for other people and then
she founded Plum, which helpsorganizations fully leverage the
human potential within theirworkforce.
It equips business leaders withthe talent data needed to match
(01:31):
employees' talent to the roleswhere they'll thrive, so that
businesses can thrive too.
And you may have read aboutPlum.
They've been in lots of newsmedia, in the New York Times and
the Globe and Mail and globalTV all over the place, and I'm
so thrilled to have you heretoday.
Welcome, caitlin.
Caitlin (01:48):
Thank you so much for having me.
I'm really excited for thisconversation.
Julie (01:51):
Yeah, I'm excited too and I love sort of like homegrown
story, and female entrepreneursobviously are my thing and I'm
so glad to have you here becauseI think it's so interesting.
You know the technology companythat you founded and sort of
what your why was.
What can you tell me about youknow what gave you the
(02:12):
inspiration to start Plum?
Caitlin (02:16):
Selfishly.
I needed Plum in order to be asuccessful CEO.
First and foremost, it startedout of I was my first customer
and I saw the value firsthand.
And then it's grown over timeto now my why is really my kids.
And I'll take a step back andkind of explain how we got here.
(02:38):
But, yes, at the end of the day, the story still came back to I
couldn't do my job unless I hadthis data.
So I had built two businessesfor other people before starting
Plum and the second business Iwas hired by a Canadian
educational technology companyto go down to New Hampshire and
start up and run the US branch.
(02:59):
And my executive coach at thetime said Caitlin, if you screw
up that first hire, it'll be aloss of $300,000 on the business
.
So, not wanting to make thatmistake, I ended up using this
(03:22):
psychometric assessment, thisbehavioral.
I was able to use thisassessment on every single
applicant that applied for thejob and we had 80 people apply
for the job and two candidatesstood out for totally different
reasons.
One was this guy who wasperfect on paper.
He had a master's in education,five years of relevant work
experience.
My CEO back in Canada wasdrooling.
(03:43):
This was the golden boy byevery measure, but the
assessment showed that he had amediocre work ethic.
But he was hired anyway.
And then we had this otherperson and she scored in the top
third percentile of the entireworkforce for overall
productivity, and my executivecoach said that statistically
she was one in a thousand andI'd be an idiot not to hire her.
So I ran an experiment andhired the guy that was perfect
(04:04):
on paper and the woman that hadthe highest assessment scores,
and three months later the guy'sfancy football team was doing
really well, but he was onlydoing 10% of his work.
So he was let go, and the womanwas doing not only all of his
work and hers, but within a yearand a half she had replaced me
as acting president while I wenton maternity leave.
And the punchline is is thatshe had two art degrees, her
(04:25):
only work experience had beenseven years of waitressing and
she didn't even know how to useExcel.
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 thebusiness over three years I just
kept screening in theseincredible diamonds in the rough
.
The next hire was this highschool student that we wanted to
(04:47):
hire 20 hours a week to do oursocial media and our new website
, and he was literallyoutperforming people that were
making over a hundred thousanddollars, and he's since gone on
and founded his own companies.
And the next person had droppedout of college to literally
join the circus.
So we hired an ex-Carney bestcustomer success manager, no
tech experience prior, and wecould just see these incredibly
(05:11):
loyal people that were so drivenwere top performers, and
there's no way, without thisdata, I would have ever selected
them out of piles of resumes.
So I had already built twobusinesses for other people.
I just started my family andreally wanted to come back to
Canada, and as an entrepreneur,you know like I'm just a gap
(05:34):
closer.
I see a problem and I want toclose that gap, and it didn't
matter if I was working forsomebody else or if I was doing
it myself.
I was going to be working thecrazy long hours and solving
problems no matter what, and sothere was an opportunity to say,
hey, if I'm going to put in theblood, sweat and tears.
I might as well this time, doit for myself and my co-founder,
who's my husband.
(05:55):
We had been working together atthe ed tech company.
He was the expert in thesoftware and he's the one that
got me the job.
And so we moved down to NewHampshire and ran that business
for three years together and wealso realized that we worked
better together than not, and,being an entrepreneur, you know
the sacrifices, you know thelong hours, and it's much easier
(06:16):
if somebody has the same kindof understanding of your whole
life and commitment and thetrade-offs.
And so we had loved workingtogether for those three years
and wanted to come back toCanada because we had started a
family, and so we're like weshould do this for ourselves, we
should run our own business.
And he came back from work youknow I was two weeks overdue to
give labor and he's like I'vegot the idea.
(06:38):
Let's take this consultingservice, let's take it out of
the hands of these reallyexpensive consultants and let's
turn it into software as aservice.
Let's democratize access to itso that every single person and
every single role can be matchedbased on this data.
That, based in industrialorganizational psychology, is
(06:58):
four times more accurate than aresume at predicting on the job
success.
And so we started it because Icould never imagine successfully
running our business orsomebody else's business without
this data.
It's like putting a pair ofglasses on.
And so I was like I'm not goingto be successful unless I have
this.
So I might as well go and buildsomething that really, at that
(07:19):
time, didn't exist as a software.
And then now you know, our kidsare 13 and nine and you know I
don't care when they start theircareer if they're doctors,
lawyers, teachers, nurses.
I just want them to be happyand fulfilled.
And when I look at thelandscape for how people get
matched to roles, there isn't asolution out there.
(07:41):
And so we we kept going withPlum because we imagined a world
like LinkedIn.
Instead of it saying whatyou've done historically, it
talks about what you could do ifgiven the opportunity, and can
really reveal to people whatdrives them and gives them a
sense of self-worth and helpsthem match to jobs where they're
going to flourish, because webelieve that when people
(08:02):
flourish, businesses thrive.
Julie (08:04):
So 13 years.
Your oldest is 13.
So you're basically coming upto that 13 year mark now and
obviously building any kind ofsoftware product is a long and
expensive road to go down.
I know you've raised money overtime.
What has that been like for you?
Caitlin (08:24):
Yeah, I've raised 19 million Canadian to date.
It's been a groundbreakingjourney.
There's very few women CEOs inCanada that have raised that
amount of capital.
I remember that when I went toraise I had raised 2 million of
(08:44):
angel capital.
So a lot of $25,000 checks at atime, a few more, a few that
were a bit more, but a lot ofindividual people that were
business owners themselves thatbelieved in what we were doing
and it took two years to raisethat first 2 million.
And I had my second kid in themiddle of that.
I literally fundraised pregnant.
(09:05):
Surprisingly, nobody gave memoney while I was pregnant.
But two months after givingbirth to my second I was on
stage in Buffalo at a pitchcompetition where we won
$250,000 US and then we had awhole 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 2million, but that was all angel
(09:27):
money.
When I went to raise my firstround from Venture Capitalists,
it was a really interestingexperience because I remember at
the time when I started, bdc'sreport 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 inthat 2 million in two years.
(09:49):
So I wanted to be the firstwoman to raise 5 million in one
go.
By the time I did, I thinkthere were about three other
women that had done it by thatpoint, so it wasn't the first,
which was, you know, the morethe merrier more of us need
capital, but it was, and Ididn't have the Rolodex.
(10:10):
I'm in Waterloo, ontario,really amazing tech ecosystem,
but a lot of bootstrappedcompanies, not a huge investor
community.
There's a good angel community,but we don't have a lot of
venture capitals, or at leasteight years ago we didn't have a
lot of those venturecapitalists here.
(10:31):
And so what I found is that mynetwork I wasn't one degree away
from the check writers, and soit took me about two years to
just build up my Rolodex, sothat I eventually went through a
hundred no's before I got totwo yeses.
(10:52):
And then, as I was down to twoterm sheets, one out of New York
City and then one out ofToronto, slash Montreal it
really came down to do I have aninvestor that I really can see
being a partner with?
Do I really believe that theyhave my back and that we are
(11:12):
aligned, because if we're notaligned, eventually things are
going to get tough and they'renot going to be there.
And I was really, really luckythat Real Ventures, which is
based out of Montreal but hasoffice in Toronto they were on
their own transformation andtheir own journey, where they
were really believing ininvesting in the potential of
(11:36):
businesses that were trying tohave the impact on that had
purpose basically companies thatwere trying to do more than
just make money, that theywanted to have a positive impact
on the world.
And you know, this was reallyabout how do we give everybody
the opportunity, regardless oftheir background, regardless of
(11:56):
their experience, to really bein a career that allows them to
be happy, fulfilled and thrive?
So they really believed in thevision and at the time, janet
Bannister came in as my leadinvestor and it was amazing to
have a woman VC on my board andto nurture that relationship.
(12:16):
And what?
Years later, I can look backand say every time that it was
one of those forks in the roadwhere we had lots of potential
but not necessarily enough prooffor everybody to jump on board
and say, okay, I'm going to fundthe next round.
Real Ventures and Janet werealways there for us, just always
there, and if there ever wasmisalignment, there was the work
(12:39):
that was needed to find thealignment and it ended up being
a really positive experience.
But when you start on thehamster wheel of relying on
outside capital in order to runyour business and I just said I
spent two years raising 2million I spent two years, you
know, building my Rolodex I, youknow, got a hundred no's.
(13:01):
Well, in the process of raising, you know, 19 million, I've
probably had 400 no's, maybe 500no's at this point.
So there's kind of two thingsthat I've learned from this.
Besides the positive parts oflike it's really important to
find an amazing investor thatreally believes in you, is
aligned and I'm very, very, verylucky on so many levels the
(13:24):
things that I've realized is thenumber of hours that I put into
developing that muscle ofbecoming good and successful at
fundraising.
I really wish in hindsight I hadput those hours into learning
how to be the best sales CEOever.
I'm a really strong operationalCEO.
I've obviously had successfundraising in the grand scheme
(13:46):
of line me up against otherCanadians, but I wish that I had
developed instead of learninghow to pitch decks instead of
learning how to do a pitchcompetition instead of talking
to VCs.
I wish all those hours ofgetting good at that I had spent
learning how to be the bestsales leader, and that's been a
(14:07):
journey that I've really had theprivilege to be able to do,
thanks to partnering with mychief revenue officer, who had
that skill set and really wasable to mentor me and coach me
and do that peer learning whereI'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, whatwould that have been like if I'd
(14:28):
been doing it for the last 13years?
So I feel like celebrating thesuccess of the investing is
sometimes setting the wrongmessage to what does success
actually mean as being anentrepreneur?
And I think the amount of moneythat you've raised can be a
misleading indicator.
(14:49):
And the other part is that Itruly believe and there's lots
of research to support this Ithink the whole funding um
market has changed in the lasttwo years.
The idea that Reid Hoffman putout the book blitz scaling was
that an investor would put in $1and they get $2 return.
That was because valuations,you know, to $5 million in
(15:14):
revenue, you could maybe exitfor $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 wasgrowing my business, when they
got to $7 million Canadian, theyhad exits that were $100,000,
$120,000, $150,000.
That's amazing In this day andage.
Those companies now would begetting three or four, maybe
(15:38):
five X of valuation.
The math is totally different.
So they're maybe getting $35million today versus when they
did this $100 million that theygot five years ago.
Exactly so the rule book, theplaybook that I grew up on, the
playbook for really the firstdecade of running this business.
That playbook now is in thegarbage and has been lit on fire
(16:00):
and I don't think it's evercoming back.
So it's really, really, reallyimportant for people that are
starting their entrepreneurialjourney to go.
Wait a second is that actuallythe right playbook?
Is that the right risk reward?
Is that the right way ofrunning a business?
And so it is.
(16:21):
With technology at the time,developers are really expensive,
Infrastructure is reallyexpensive.
I knew I could not build thisbusiness unless it had outside
capital, and that was the goalfrom I'd already started
businesses that werebootstrapped from other people.
I wanted this to be VC backed,but now, with generative AI, I
mean it is amazing how companiesdon't need to just keep adding
(16:44):
bodies in order to grow.
There's other ways to grow andscale, and I mentor through Real
Ventures.
They have a really amazingmentorship program and I have
the ability to mentor two peoplethat are early, and each of
these teams are two people, fourpeople, and my advice is don't
spend a lot of time fundraising.
(17:05):
If they're throwing money atyou and one of them was it's
like OK, that's great, but makesure you have alignment.
But if they're coming to you,that's a different thing.
But don't waste your time goingout.
And then the other thing is isdon't just take that money and
automatically start hiring abunch of people Like what are
the roles and responsibilitiesthat aren't getting taken care
of?
Is that more important?
(17:26):
What's the order of operations?
Is that going to drive morerevenue and is that just more
generative AI, or is that anoutsourced virtual assistant?
There are more ways of solvingit that are less expensive than
how I was running the businessin the first decade, and so
there's an opportunity, I think,to do things differently than
(17:51):
the playbook that I use to buildthis company.
Julie (17:53):
I think it's one of the really interesting things I'm
seeing with entrepreneurs rightnow is sort of smaller core
teams.
Lots of things are sort ofoutsourced or third party or
automated, where you know, wewere 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 inCOVID and when it doesn't work,
it's because not enoughresources have been put into how
to make that environmentsuccessful.
And when you're low onresources and cash, it's one of
(18:29):
the first things that getssacrificed.
So it's not easy, but I thinkthere are so many benefits, um,
from being fully remote.
I benefited from the fact thatI had a core team that had years
of working together in person.
So, as the nature of our youknow, team shifts and we get
more and more of just remotepeople, you know I'm I'm
(18:50):
reevaluating all the pros andcons, but it can be a really big
unlock to to stay remote, causeyou, you have a lots of
possibilities.
And then the other thing we'vedone is take advantage of
fractional services.
So we moved up market toenterprise four years ago and so
we needed a chief security andcompliance officer.
I can't.
I can't afford that personfull-time and I don't have
(19:13):
enough enterprise customers tokeep that person busy full,
full-time.
We drink our own champagne.
So, even though we can have afull-time HR person, you really
want somebody who's at theforefront of strategy and
thinking about thingsdifferently and really
rethinking about work on aregular cadence.
Who also is seeing how otherbusinesses are changing?
(19:36):
So we have a fractional chiefpeople officer.
My CFO is on mat leave, so wehave a fractional CFO while our
manager of finance can run theday-to-day.
So we've really benefited fromthat fractional, really senior
expertise so that we can kind ofpunch above our weight.
(19:56):
And we haven't done a lot ofthe outsourcing kind of overseas
.
We tried a little bit of thatearly on.
That hasn't been the success ofour experience, but a lot of
taking advantage of peopleemployees across Canada and the
US and that fractional supportand taking advantage of the
(20:17):
benefits that, especially nowit's a real differentiator to
stay dedicated to being remote.
So many companies that havehybrid environments they see the
clock ticking that one day aweek in the office, now two days
in the week in the office, nowthree days in the office and you
know they don't trust that ahybrid environment is going to
(20:37):
actually stay hybrid, whereaswe'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 advantagesto staying remote are that your
talent pool is geographically,you know, infinite in theory.
Yeah, because that always plumaside.
It's always the hardest thingright of finding the right
people is, you know, the rightperson, the right price and all
(21:06):
of the things.
Yeah, yeah absolutely yeah.
And so why?
Why do people like?
I mean, we talked about how theflooding that's happening when
companies are posting jobs nowand you know they're getting
thousands of applicants, and sohow the assessment tool can
really help them both to narrowthe field, hire the right people
(21:30):
, but also with that retentionpiece.
Caitlin (21:33):
Yeah.
So what's really interestingand most of us, as business
owners, we're never taught this,like you would think that this
would be common knowledge, butsomehow it's a hidden secret
there's real science behindperformance and retention, and
the science is crystal clear.
And there's an entire domain ofscience called industrial
(21:54):
organizational psychology.
People go to university, theyget PhDs in it.
It's a category that's beendefined as a science.
So these are these experts thatreally, in the last 30 years,
have honed the craft, andthere's a set of best practices
and a set of conclusions thatare really undisputable at this
point.
And it's that when you line upa hundred people and that are
(22:18):
all doing the same job and youlook at what makes a top
performer different than anaverage and below average
performer, it's never where didthey go to school, it's never
what past experience they have.
Those things are helpful toknow.
If they can do the job, like ifyou hired them today, can they
tomorrow go ahead and punch thatwidget, you know, um.
(22:41):
But if you look at a hundredpeople similar background,
similar experience and you wantto understand what's going to
make somebody outperform theirpeers and what's going to make
somebody stay in their joblonger, it is behavior.
It is those innate talents wecall them durable skills.
They're going to endure andstay durable throughout their
(23:04):
entire career, no matter howtheir job descriptions change.
It is the thing that makespeople jump out of the bed in
the morning, loving the job thatthey do, high-fiving their
family, at the end of the day,saying I had the best day.
It is the thing that allows usto, you know, win the race in
our lane over our peers, becauseit comes naturally, it's easy
(23:25):
and we enjoy it.
And, on the flip side, we allhave things that drain us, and
if we're in roles that areconstantly asking us to do the
things that take me three timeslonger to do than you, then I'm
going to not perform as best andI'm going to feel drained and
burnt out and I'm going to leavethat job.
So it's it's the behavioralalignment between what are my
natural behaviors and what arethe behaviors that my job
(23:46):
requires, and if they're aligned, then I'm going to outperform
my peers and I'm going to lovemy job and I'm going to stay
longer.
And so that that thosemeasuring of durable skills for
the person in the role andmatching them together, that is
four times more accurate than aresume, that past experience in
education at predicting on thejob success and performance.
The issue is is that 20 yearsago, 10 years ago, to access
(24:12):
that kind of data on anindividual sucked?
It was really expensive on theemployer.
It was a horrible experience onthe employee or the candidate
Like it.
It just, yes, that was bestpractices, but it wasn't
something that we could accesswithout hiring a professional
and then coming in with theirdecoder ring and interpreting
all the results.
So that's why we started Plumto say, hey, what about if we
(24:35):
took this best in class sciencebut then flipped it on its head
so that the individual, the jobseeker, the employee, would love
going through a 20, 25 minuteassessment and getting their own
profile, their own report whenthey're done and developing that
self-awareness on what makesthem exceptional.
(24:55):
And then they're simply sharingthat data with an employer.
And then the employer has theability to say this is great,
but like, what's job relevant,what matters to me, and match
that to the behaviors thatpredict success in their unique
job.
And so the idea was this is adata problem and in an ideal
world you want as many peoplebecause it's statistics.
(25:16):
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'vegot 20 to choose from, but of
the 20, how many can hit theground running or meet your
salary requirements or meetwhatever other information you
have?
So if you have thousands ofapplicants, the chances of you
(25:36):
screening in those diamonds inthe rough that also have the
other things you need is amazing.
And so, all of a sudden, theproblem that everyone's facing
where they're getting spammedwith people is actually now a
benefit, because we have thislayer of data that you use right
at the beginning to simply say,statistically, who's most
likely long-term to be the bestinvestment.
(25:58):
And I'm going to start at thetop and work my way down.
Look at the other informationand now, before the interview,
before I get kind of conned inthe most assertive interviewers
with the most outgoing that tendto perform better in the
interview but not necessarily onthe job, I now have this
unbiased data that allows me tosee if they're a good fit, so
(26:19):
that I'm only interviewing thepeople that, statistically, are
likely to work out.
And this is more important thanever because Gen AI is allowing
every job seeker to sign up fora service like Lazy Apply and a
candidate can apply to 5,000jobs in their sleep and so you
get.
You know keyword stuffing intheir resume and you know ATSs
(26:40):
applicant tracking systems thatare keyword scraping and
eliminating people and you havethis race to the bottom where
it's bot against bot, keywordsagainst keywords, and
everybody's just overwhelmed andthe system's practically
bankrupt.
So Plum can come in and be thatfilter based on what really
matters, which is do you need aninnovative person for your job
(27:02):
that's good at working on teamsand getting the job done and
completing tasks?
Great?
Here's your 98 match that, nomatter what they've done in
their career, that's what getsthem out of bed in the morning.
That was me.
That's what makes themexceptional.
And, by the way, you, as a jobseeker and employee, you may not
have realized that you were sogood at conflict resolution
because it comes so naturally toyou.
(27:22):
You didn't.
You forgot to even mention that.
That was a superpower.
It's really exceptional.
You should talk about that andlook for jobs that need that.
Julie (27:31):
Well, and it's so interesting that at this point
in the timeline, that thechanges in the technology
environment, with generative AIand all of the things that are
happening, have made you morerelevant than ever.
Caitlin (27:44):
It has been really amazing.
The interesting thing that'shappening in the market is that
people are moving into this eraof skills-based hiring and
skills-based employeedevelopment, but they still
think that skills means do theyknow Excel?
Do they know you know Python,do they like?
(28:05):
It's still just coming back tothose keywords, and so there's
still a huge job to educate themarket that you know those type
of skills like Excel and Python.
You know those skills reallyare.
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 becomingperishable skills.
The hard skills we've alltalked about really should be
rebranded to perishable skillsbecause their relevance is
really diminishing.
But the durable skills, likesomebody's ability to innovate,
communicate really should berebranded to perishable skills
because their relevance isreally diminishing.
But the durable skills likesomebody's ability to innovate,
communicate, execute thosedurable skills are what predicts
performance.
It's what's necessary, butpeople just don't know that they
(28:49):
can measure those and that theycan use that as their very
first filter top of the funnelto shortlist who they should
then take their human time to gothrough and evaluate and
consider.
And when you change the processto looking at potential first,
what happens is you end upscreening in people that don't
have as high of salaryexpectations because they
(29:10):
haven't been doing it for 20years.
You have people that are goingto learn quickly on the job and
value the fact that you took achance on them, and that means
that you're also getting a bitof a discount and this increased
loyalty.
So there's huge opportunitiesto go after diamonds in the
rough that no one else islooking at and you're going to
(29:31):
get a top performer, probably atless cost, and they're going to
stay and be loyal and trulyenjoy their job, like it's
really a win win for all partiesand it's just a matter of
educating people that there is adifferent way to do things and
it's it's hard to change thestatus 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 manycountries did you say you're in,
a lot?
Caitlin (29:59):
147.
Yeah, yeah it, uh, it has.
It's been amazing.
We have about 50,000 people amonth that complete their plum
profile.
It's completely free forindividuals so they can go right
off to plumio and completetheir own plum profile and share
it on LinkedIn.
We have people by the minutesaying you know, these are my
(30:20):
top talents.
Thank you for the opportunityto be seen not just based on
what I've done historically, butbased on what I could do if
given the opportunity.
So it is pretty powerful andamazing.
And we, you know we work withreally big global enterprise
companies like Whirlpool andCitibank and Scotiabank, but we
also still work with SMBs andmid-market.
(30:42):
That you know.
You know that that criticalhire is going to be what makes
or breaks them.
Or they're just now thinkingabout internal mobility or
succession planning and bygetting it right, they're not
going to, you know, accidentallyhire their best sales rep to be
their sales leader and then allof a sudden lose a great quota
carrying person because theyweren't a great people leader.
(31:04):
Like being able to provide that.
De-risking the statistics ofthe 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 breakmoves, but it's been very
rewarding to move into theseglobal recognized enterprise
companies and truly help themwith the scale that we uniquely
(31:25):
can do.
So it's been very rewarding.
Julie (31:28):
And so what's next?
What's next on your path toworld domination?
Caitlin (31:32):
Partnerships has been kind of the next chapter, which
is, I feel like, again, a wholenew muscle, a whole new playbook
kind of the next chapter whichis, I feel like, again a whole
new muscle, a whole new playbook, whole new opportunity to grow.
Um, we've been really, reallylucky to integrate with um with
the systems of record that othercompanies use, so SAP, success
(31:53):
factors or workday or ISIMs orPaylocityity is a new one that
we have a full integration with,and what's great with that is
that you can go to markettogether.
You can go to their customerbase.
You can talk about the one plusone equals three.
You can do joint eventstogether and so, instead of
paying a certain amount ofmarketing dollars to go to an
(32:14):
event, you can pay a lot lessand go to a partnership event
and talk to their customers anddo joint things together and so
getting to the place where youknow, when you're not known,
those big guys won't reallyengage and they have so many
partners they won't prioritizeyou.
But we've been really good atgrowing our brand and showing
(32:35):
that we're different and we'redifferentiated and we have
marketing that really stands out, that now they want to partner
with us because they want to bepart of collaborating with our
really innovative marketing andso it's been the right time over
the last year and a half toreally kind of do partnerships.
We tried doing it before COVID,like the year before COVID, and
(32:56):
it was too early.
So much of this is it has to bestage appropriate, so you get
this really good advice.
So I can be like partnershipsare so great, but if you do them
too early you don't have thenecessary means to make them
successful.
So half of the battle of beinga CEO is like this is all really
great advice, but how do youget the right order of
(33:17):
operations, the right timing?
And I think we finally nailedthe right timing on partnerships
and I'm excited to see thatcontinue to blossom.
And there's some really reallyexciting ones that we're right
on the cusp with and othersreally great success stories of
customers we've gone togetherwith which are really cool, and
(33:37):
there's a range.
There's technology partners,but there's also consulting
services that are really takingcare of the change management.
But that's just kind of gettingin front of existing partners.
Customers is really the thingwe'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 enteringthe partnership pool.
You're not new.
You're not a new player, you'rejust 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 swallowedup by their largest customers.
We can be like, no, we canhandle those.
And it's interesting Like mostcompanies wait until they've
kind of dominated and have themajority of their revenue coming
from SMBs or mid-market beforegoing to enterprise.
(34:24):
But we kind of accidentallystarted getting some enterprise
customers and being able to beatout our competition, some
legacy providers and they cameback to us and said you know,
caitlin, that's great that youcan help us with hiring, but
what about our existingemployees?
Can you help us?
We have a reorg or we have asuccession planning or we have
an upskilling initiative thatwe're doing.
And in 2018, we had threeenterprise companies all at the
(34:47):
same time say can we shoehornyour 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 theyall came back and said I never
would have promoted these people, I never would have identified
them, like we were screening inthe diamonds in the rough inside
our own company, and thisdelivered results we never could
(35:07):
have done without Plum.
So that's what actually led usto in 2019, raising the $5
million from Real Ventures, ledby Real Ventures, and that's
what made us go out and buildour product for enterprise and
the full lifecycle talentacquisition and talent
management and launched that inearly 2021.
So once we were in enterprise,we're like we have to focus all
(35:30):
our effort, all of our productdevelopment.
Integrations matter in adifferent way when you're at
that size.
So it just really pulled thefocus.
Um, even though we serve thesmaller customers, it it really
narrowed our focus in terms ofhow to make decisions and who
are we building for and who arewe targeting.
But it's been a journey ofwhale hunting when you are, when
(35:52):
it feels like you're in a canoeand you're whale hunting and
it's amazing when um like that,we can do it.
But that has been an entire kindof learning curve in itself is
it's you have to be very, very,very brave and and it requires
again, like VC money we weraised uh, 8 million Canadian
(36:15):
was the last round we did.
There's a little bit in betweenled by Pearson Ventures, the
textbook publishing company.
They have a big future of workmandate and they really saw this
kind of human first vision ofthe future and individuals
having control of their data andreally guiding their own
careers, and so they led ourlast round and it's amazing to
(36:39):
kind of be on this journey, butto go after the go-to-market
strategy for enterprise is somuch more costly and is is a big
lift.
And so you know, we're gratefulthat we had the VC money in
order to do it, but itdefinitely feels that we've
taken some of the paths lessless normally gone.
Normally, enterprise comes muchlater.
So you have this base to kindof weather the storm.
(37:00):
But we were like all in onenterprise 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 amable to be.
I don't need to be in everymeeting by any means, but I find
that if I step back too muchbecause what's interesting is in
2022, I would say we had thisunbelievable product market fit.
It felt like magic.
(37:33):
People in the startup worldtalk about product market fit
all the time, and the way I'vekind of defined it is that if
you talk to 10 customers, youknow how many of them instantly
go.
You're solving my problem.
Nobody else is like I neededthis yesterday.
Yes, yes, yes, and I remember,you know, for a long time,
because people don't know thatthis exists.
(37:55):
It felt like if we talked to 10people, four would be
interested and maybe two wouldbuy, and so it just felt like
you're constantly pushing aboulder uphill.
And in 2022, everything justfinally clicked All the changes
bringing in a chief revenueofficer that brought in a bunch
of changes.
Everything just started toclick and if we talked to 10
(38:15):
people, it's like eight, youknow, eight to nine would say
yes and seven to eight would goforward and pay, and it just was
like this incredible thing.
But most enterprise companiesat least, and I think a lot of
the industry stopped hiring lastyear in 2024.
So overnight our product didn'tchange.
(38:35):
The product part of ProductMarket Fit didn't change.
The product part of productmarket fit didn't change, the
market changed.
And so to be involved in salesand 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'shappening.
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 productand the market, as it needs to
iterate and change.
And that is the advantage ofbeing the CEO is you can.
I always want to be alignedwith my executive team, but
there is an ability to go.
Oh, my goodness, okay,everybody turn right because,
(39:18):
like we're not getting anythingfrom left right now, we need to
go hard right because the markethas changed.
So last year it was a reallyhard adjustment.
Okay, talent management we needto be all in on talent
management.
Well, now, in 2025, people arehiring again.
We have customers.
I just saw on our Slack channeltoday this customer that loved
us that stopped theirsubscription last year because
they were not hiring.
(39:38):
They're back, they want toreactivate their account and
it's like, oh right, that'swhat's happened, that we saw
that in COVID people stoppedtheir subscriptions and then
they came back because they werehiring again.
We need to go back to our pastcustomers and run and run a
campaign because they'll careabout us again.
They didn't care, they hadcrises of their own, layoffs of
(39:59):
their own last year, but they'regoing to care again and just
being close to it and findingthese ways of reengaging.
I love that part of my job.
I was going through old Zoomrecordings of meetings from back
in 2021, and I noticed that themeetings I got brought into
there were chief people officerson the other end.
Well, those chief peopleofficers, if I look at LinkedIn,
(40:21):
have moved two times since, andso I'm like, okay, let's divide
up these old people that are innew companies that we know in
2025 are now growing.
Let's do some account-basedmarketing out to these key
stakeholders that already saw ademo of us in 2022 or 2021, you
know when things were goingreally well and let's re-engage
(40:41):
them as a as a human now at anew company.
And so I I like solving problems, but if I'm too far away from
the customer that I'm, I don'tget to solve the customer
problems.
I work on the operationalproblems and that's where I'm
always going to feel safe.
That's always where I'm goingto default to.
So, by by being with thecustomers, it constantly allows
(41:02):
that to stay top of mind andfind new ways to grow and um, so
, yeah, I, I'm, I'm, I'm findingnew 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 asyou grow the business on to the
next level and sign up moreenterprise clients and keep
growing Plum.
Yeah, Thank you so much forjoining 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.
I hope you enjoyed today'sepisode.
Please remember to hitsubscribe on your favorite
podcast platform so you won'tmiss any episodes.
Figure Eight isn't just apodcast.
It's a way of seeing the big,gorgeous goals of women
entrepreneurs coming to life.
If you're interested inlearning more, you can find my
(41:57):
book Big Gorgeous Goals onAmazon, anywhere you might live,
For more about my growth andleadership training programs.
Visit www.
julieellis.
ca to see how we might worktogether.
Read my blog or sign up to getyour free diagnostic.
Are you ready for growth?
(42:18):
Once again, that's www.
julieellis.
ca.
When we work together, we allwin.
See you again soon for anotherepisode of Figure 8.
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