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May 19, 2025 43 mins

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In this episode of The Tech Trajectory Podcast, host Kavita Kerwar sits down with Karis Dorrigan to explore what leadership looks like when driven by clarity, values, and life’s changing seasons.

From negotiating for flexible work to growing through career transitions and motherhood, Karis shares her journey with candour. She speaks about how to lead with both empathy and commercial focus, why inclusive product teams matter, and the value of redefining success on your own terms.

You’ll hear advice on part-time leadership, the impact of mentorship, and what businesses can do to truly support diverse teams and individuals—not just on paper, but in practice.

1. Flexibility doesn’t mean less ambition

[03:00] Karis discusses working part-time in a senior leadership role—and how she reframed flexibility as a strength, not a sacrifice.

2. Making work work, for people and life

[06:15] Teams thrive when flexible work is seen as a competitive edge. Karis shares practical actions to make part-time and remote employees feel valued.

3. Redefining leadership through motherhood

[09:00] Parenthood shifted Karis’s leadership style, grounding it in empathy, prioritisation, and purpose.

4. Navigating big career transitions

[15:00] Karis reflects on leaving high-profile roles, listening to your instincts, and designing a career that aligns with your values.

5. Leading inclusive product teams

[21:00] Inclusion starts at the strategy stage. Karis shares how she builds empathy into team culture and product decisions.

6. Mentorship and giving back

[24:00] From being mentored to mentoring others, Karis champions honest conversations, advocacy, and opening doors.

7. Advice for future leaders

[27:00] Karis closes with reflections on confidence, clarity, and what she wishes she’d known earlier in her leadership journey.

Where to find Karis Dorrigan

Follow us on Instagram, TikTok and YouTube.

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Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Kavita Kerwar (00:00):
Hello and welcome to the tech trajectory podcast.
I'm your host, Kavita Karvar,and today we're talking about
what leadership can look likewhen it's shaped by clarity, not
compromise. Joining me in thestudio today is Karis Dorrigan,
the Head of Product at Freelywhose career has spanned
Fairfax, Qantas, big red group.
She's built high performingteams across media, travel, tech

(00:22):
and insurance, while challengingthe very traditional playbook on
what leadership should looklike. And of course, we know
Charis through our work atQantas airline and loyalty. So
welcome. Thank you. Very excitedto be here. Oh, we're very happy
to have you. To keep thingsinteresting, we're going to play
a bit of would you ratherworkplace edition. So let's

(00:44):
start off with the firstquestion of, would you rather?
Would you rather have an AIassistant that perfectly manages
your inbox but occasionallysigns off an email with XOXO, or
never receive another emailagain, but then instead have
zoom calls or MS teams callsthat go for 90 minutes.

Karis Dorrigan (01:06):
Look, I am a fairly open person, so I'm going
to go with the XOXO, becausethat would not bother me at all.
Yeah. Is it giving like GossipGirl EXO except product life,
but 90 minute calls, you know,constantly, maybe you get too
much. Yeah? Fair enough,

Kavita Kerwar (01:27):
yeah. And I think we'll get into, we'll get into a
bit of time management, and I'dlove to get your views on this,
because I know that you're in asenior leadership role, and
you're doing it part time likeyou never hear that often. It's
still pretty rare. So how didyou how did this come about, and
what helped you make it work?
Look, I think

Karis Dorrigan (01:49):
when I had my first child, it was just before
COVID, so before I ever wentback to work as a working
parent, the pandemic had hit,and it had just changed the
world, and it was remoteworking. So I think that really
worked in my favor, because mostorganizations at that time are
really open to different workingpatterns. And, you know,
everyone was doing thingsdifferently. And so to be

(02:11):
honest, I didn't really thinkabout it. I just thought, you
know, I want to, I want to bewith my children. I love my
career, and I absolutely think Ican do any role that is
advertised as a full time rolein a four day capacity. And so I
just went for it and had thoseconversations. And if I think
about it at the time, I cancount on one hand the people who

(02:32):
said no to that. And so mostcompanies were so open, I feel
like there's three camps, theones that are really progressive
and it's not even a problem, andjust work that through with you.
There's a handful that are justhard nos,
and there's some that are inbetween, and I feel like that
signal to me is, well, they'reprobably not quite there, and I
don't want to be working in anorganization that maybe says

(02:55):
yes, but then you turn up andeverything's a bit challenging.
So I think you need to reallychoose the companies that go,
you know, hell yes to this. ButI think that does come with
caution, because I do think nowthings are slightly shifting,
and it may may be morechallenging to find those
companies that are reallycomfortable with the four day

(03:15):
work pattern now that we've got,you know, a bit of a push back
into return to the office.
And so I think it's stillpossible, and people should
still absolutely go for it, butI think it's a little bit harder
than it was when I reallystepped into this working model.
Yeah, I think that's a that's agreat point, because you're
right. I think since COVID Now,there's been a there's been a

(03:36):
steer where people kind ofassociate being back at work at
work, of being physicallypresent in the office as being
more productive? Yes. And one ofthe questions I had is we often
hear that asking for flexibilityequals that maybe you're not
ambitious enough. So how do wechallenge that as individuals
and as leaders? Yeah, I thinkit's a really interesting

(03:58):
question. And from a leadershipperspective, I think we just
need to challenge our ownbiases. And so when people ask
for a four day work week, andthe initial response of your
mind might be, I really needthat five day person. There's so
think really challenge. Youknow, if we're out, if we're
much to do. Imoving to an outcome driven
world, we want impact, notoutput. I 100% believe that you

(04:19):
can achieve that with whetherit's a five day work week or a
four day work week.
Totally lost my train.

Kavita Kerwar (04:32):
That's okay. So I think what I'm hearing you say
is that when you've got moreconstraints and you're focusing
more on the outcomes rather thanthe hours you're putting in on
hitting those outcomes andhitting those milestones. And I
think at the end of the day,that that's what matters to any
business, that's what matters toany team, that they are
supported by a leader who helpsthem deliver on those rather
than the leader that perhaps isthere every second minute and

(04:55):
physically present in theoffice. Yeah. And I think from
an individual perspective, it'sthen, yeah.

Karis Dorrigan (05:00):
So also, really being clear on what the outcomes
and impact everything that youare doing is having, right? So
you know, what are the low valuetasks you can get off your
plate? We have aI now. So youknow, how can they boost your
productivity, to help you spendyour time in the complex human
work? And say, No, you know, Ithink in product and technology,

(05:22):
we should be great atprioritization. So prioritize
your workload is reallyimportant. And I think also I'm
very clear on my boundaries. So,you know, what do I really want
to do, and what actually am Isaying no to? And what are my
boundaries in a workplace when Iam working part time or

(05:43):
different working patterns,because you can often end up
just doing the full time rolebut not getting paid the full
time salary. So I also thinkit's really important to be
really clear on your boundariesand what that'll look like for
you as an individual that wantsthat kind of working rhythm.

Kavita Kerwar (05:59):
Yeah, I really like, I really like those
strategies. I think some ofthese are, like, very easily
actionable, and there's so muchdata now on different kind of
tools to use for prioritization.
And it doesn't even have to besomeone who's working a four day
week. It could be someone who'sjust across different
priorities. How do you thenprioritize your day when you're
juggling multiple priorities,and then using AI to your
advantage, using other tools toyour advantage, to maybe reduce

(06:21):
your workload or focus more onthe tasks that require more of
that creative input from Yes,

Karis Dorrigan (06:28):
absolutely. And I think there's also an element
of role shaping. And you know,I'm lucky that I lead a team.
And you know, if you're buildingthe next generation of leaders,
you need to give themopportunity. So if you are
working in a compressed workweek or a different working
pattern, being reallycomfortable carving out space
and helping your team to lift upas well, because that's going to

(06:50):
help them and help you. And so Ithink that's a really important
thing to think about as well. Ifyou are wanting to step into a
more senior role, getcomfortable with giving some of
the big, meaty leadership tasksto, you know, the next wave of
talent coming up the pipeline?
Oh

Kavita Kerwar (07:05):
yeah, 100% I think one of the things that you
touched on, I'm glad you touchedon leadership, is there's often
people in our teams who areworking part time or who are who
maybe want more flexibility. Sowhat can practical actions can
leaders take, or team memberstake to make remote employees or
people who are working inflexible schedules feel more

(07:25):
included. I

Karis Dorrigan (07:27):
think this is I'm going to be reflecting on a
lot lately, and I think there'ssome really foundational things
that we can do and we often andwe need to take the time to
intentionally think about it.
So, you know, for example, if wethink about a working week and
all of our key meetings. How arewe making sure that meetings are
in core hours, or everyone hasthe chance to show up in person
or hybrid but on the days thatthey're in the office? So I

(07:50):
think we need to be reallyintentional about that. And I
also think we need to make surethat we're not putting that
burden on the, you know, onepart time worker to tell us what
needs to happen, we need toreally think about, well, how
are we designing workplaces asleaders, and how we kind of
making sure that those voicesare heard, versus asking the one
part time worker to participatein the working group around

(08:11):
flexibility as an example. So Ithink that's really critical.

Kavita Kerwar (08:16):
Yeah, I remember when I was working part time,
and this is very early on in mycareer, and we would have, there
was certain days that I was atuni, so I would be, you know,
not at work, and we always hadour critical planning and
prioritization meetings on thatday and the next day, morning,
nine, it was an update on, howdid you go? What was your
feedback? And I was like, Idon't know, what's how you feel?

(08:38):
Really left

Karis Dorrigan (08:38):
out about inclusivity. It is, you know, a
space that makes us feel likewe're not part of the
conversation, and then there'sthat guilt, right for those
people who can't be there. Sothat's why I think it's so
important that leadership stepin and lead through that.
Because probably that person atuni or has just become a mom and
is coming back to the workplacedoesn't have the confidence to

(08:59):
put their hand up, so how do wemake sure that they don't have
to? Yeah,

Kavita Kerwar (09:03):
yeah, absolutely.
So I guess if you flip that abit, then how can businesses
perhaps reframe having aflexible, you know, workforce as
a competitive edge in someinstances, and not just as a
compromise? Because more oftenthan not, you see the rhetoric
even in the media, like goinginto the office, or like the end

(09:23):
of the work from home, or theend of flexible working. So I
guess if there, I wonder ifthere's like a shift here where
we can reframe this as ourbusiness has more of a
competitive edge because of ourflexible workplace.
And I think it

Karis Dorrigan (09:39):
absolutely does for many reasons. Well, that's
certainly my perspective, and Ithink a lot of the research, but
I think the real critical pointhere is that flexibility is
something that we all enjoy, andit helps us all thrive through
our lives, and it really has tomove away from the working
parent getting access.
Flexibility because of theircaring status, to something that

(10:01):
everyone can benefit from. I wasat this conversation a couple of
weeks ago where one of the womenwere talking about the fact that
we're now leading fivegenerations of people across all
walks of life. So with that,there's so many different needs.
There's people who might, youknow, have a neurodiversity
challenge and need to work fromhome. There's the elderly who

(10:25):
want to contribute, who maybecan't commute. There's working
parents. There's people who justwant to have fun and see their
family and go to the gym. And soI think flexibility needs to be
something that everyone isafforded, for it to really for
it to really be a benefit forall?

Kavita Kerwar (10:44):
Oh, definitely.
And I think if we just focus onone kind of working is the best
way of working, you'd be at arisk of alienating to your to
your point, like five differentgenerations. So finding
commonality and supportingeveryone so that they feel to
your point earlier, included,and they feel part of the
workplace, and they can feelproductive and empowered to do
their job. I think that's

Karis Dorrigan (11:05):
yeah. And I think the other thing on my mind
is really around mental healthand wellbeing, which is such a
big part of the workplaceconversation, and also such you
know, if we are living healthylives and we're flourishing,
we're going to be more highlyengaged, be more creative, be
more innovative. And soflexibility, to me, is a pillar
of making sure that we arecreating a really mentally

(11:27):
healthy workplace, and that isgoing to tick all of those real
big benefits around how we'reengaging our workforce and
driving innovation andcreativity.

Kavita Kerwar (11:37):
Yep. All right, I wanted to
shift the next question andfocus on a bit that you
mentioned earlier, your journeysince becoming a parent and then
working in the workforce andhaving such a senior role. So
one thing we often hear a lot,but does it get mentioned as
much in the workplace, is thepressure to have it all. You

(11:57):
know, the have it all myth, andthis can weigh quite heavily,
especially on working parents.
How have you redefined as towhat this means for you? Yeah,

Karis Dorrigan (12:07):
I think that's a really great question. And I
think for me, you know, havingit all is it really has a lot of
baggage around having thisperfect life, you know, hitting
the C suite, having a thrivingfamily, you know, going to
Europe, doing all the things.
And, you know, I think that isreally something that we need to

(12:28):
kind of challenge, becausewhilst it might tick all of
those boxes from an externalperspective, actually, is it
going to make you happy? BigQuestion mark. So for me, it's
really about shifting thatnarrative from having it all to
living my values fully. Andthat, you know, has been a
journey for me, but I think hascrystallized through parenthood,

(12:51):
and I've had a lot more clarityin that. And I think when we
think about, well, am I showingup and living my values through
my life? Be that at home with myfamily, with my friends, and
through my career and livingaligned to that. I think for me,
that's what's having it all, andI think we can have that, but it
also means make prioritizing,making the decisions around

(13:14):
what's important in that momentof your life, and it means
saying no to a lot of things.
And so for me, you know, my corevalues at this time in my life
are connection, adventure,integrity, and if I think about
those things, I can absolutelyhave those through every facet

(13:35):
of my life.

Kavita Kerwar (13:36):
Yeah, 100% I really, this really resonates
with me, because I'm SouthAsian, and we have such a strong
social conditioning from, like,a really young age of you need
to have it all, and especiallyif you are female. Then in the
90s, at least, everyone'sparents wanted their children to
eventually be successful and befinancially independent, and

(13:56):
then you have all this pressure.
I mean, financial independenceis a great thing. That's not
what it's like, but you have agreat pressure of trying to be
like a CEO, or aiming to be Csuite, and then being Martha
Stewart at home and having theseamazing children and an amazing
very condo at home. And that'snot what having it all means,
does it? Doesn't mean puttingall that pressure on yourself.
And this really resonates withme, like finding out what you

(14:18):
need and what values of life doyou need to make you happy
totally.

Karis Dorrigan (14:23):
And I mean, I've been there too, right? You know?
Oh yes, the C suite job is goingto make me so happy. But now, to
be honest, if I thought aboutthe C suite job, maybe it's what
I want, but if I think about myvalue of connection and time
with my family, and what thatlooks like now, it will probably
be a no for me at this point inmy life, because I have a great
career. I'm Senior, I'm drivingimpact. I've got amazing

(14:47):
colleagues and an amazing bosswho supports what I need in life
and outside of life. And so ifthat, if that job came to me
now, and it meant saying no tohome life, I would have to. A
quite easily no to the role,

Kavita Kerwar (15:03):
yeah, and that's very powerful. And I guess it's
also because you're so selfaware now of what you need to
thrive and what makes you happy,whether you're in the workplace
or at home. Yes,

Karis Dorrigan (15:15):
totally. And if that job came up and it ticked
all those boxes and it didn'teat into connection as a value,
then that's a very differentconversation to have.

Kavita Kerwar (15:23):
Yeah, that's That's great. My next question
was going to be, How has being aparent shifted your approach to
leadership or decision making?
But I think you've alreadyanswered,

Karis Dorrigan (15:32):
yeah, I know. So I think it's just made
everything more crystal clear,yeah,

Kavita Kerwar (15:38):
did parenthood kind of help you shift or
gravitate towards certain kindof roles or certain companies.
Do you think?

Karis Dorrigan (15:47):
Look, I think it to my earlier points, has made
me much more intentional aboutthe companies that I've worked
for. It's made me think aboutmuch making sure that the
companies are aligned to myvalues and my needs as a person,
not just as a worker. So 100%yes, it has, and it's all around

(16:11):
values alignment. You know, Ican have time at work and with
my family and thoseorganizations really do believe
in the progressive views of waysof working in the future of
work, yeah.

Kavita Kerwar (16:23):
And I guess for our listeners, it doesn't even
have to be parenthood,necessarily. It might just be
you're at the point in time inyour life where you're looking
back and you're reflecting onyour conditioning and being
like, am I running towards ajob, and is this actually giving
me happiness, or do I need tolook at what value is bringing
to my life, and how do I makesure that I'm happy and thriving

(16:44):
in

Karis Dorrigan (16:45):
the world? Yeah.
I mean, wouldn't it be great ifI figured these things out 30
years ago? So yes, I think it'sso important every aspect of
your life. Yeah,

Kavita Kerwar (16:55):
you spoken about, you know, your life and your
home life and work life, whatsupport systems at home or at
work have made the biggestdifference in helping you lead?

Karis Dorrigan (17:07):
Well, look, I think honestly, on this
question, to answer thisquestion, I don't think there
have been any big, amazingsupport systems that have made
it work, which I think isdisappointing, and I think is
why I'm so passionate abouthaving these conversations
around what that does look like.
So we can provide a supportiveworking environment for parents
and solo parents in particular,but everyone ultimately wins, I

(17:29):
think, through that. So, youknow, that's the, I guess, truth
of the matter, but in terms of,then support systems more
generally, I think for me, it'shasn't been the big, burly one
thing. It's been all of thesmall things that we put in
place to help us. And so, youknow, reflecting on this, I
think one is just myself beingclear on those values, those

(17:51):
boundaries, and really beingtrue to that. My second is my
mother, who looks after my kidson a Thursday, which is my
working in the office, one of mywork in the office days, and so
that takes a lot of stress outof things, and they get time
with her,and then it's all the small
things. So I had a bit of ameltdown at work about a month
ago, and my boss is like,charis, you need to outsource
more, get a cleaner. And I didgame changer. So, you know,

(18:16):
these like, what is humans andwomen. Can we outsource? Yep,
you know, I have a robo mower.
Game Changer. The mindset oflowering my lawn, mowing my lawn
gone. Yes, all those littlethings that add up. And then I
think finally, in terms of thisisn't really a support system,
but it's just we, well, I, youknow, everyone, but particularly

(18:39):
working moms and parents, Ithink, have a lot of guilt, so
it's just like, just lose that.

Kavita Kerwar (18:45):
Wow. Yeah, I think that makes, that makes a
lot of sense. Like, I remember afew years back, I was looking
back at a weekend and thinking,Where did all my time go? And I
noted down all my tasks, and Iwas like, wow, I've spent a lot
of time weeding this lawn anddoing the lawn mowing. And I'm
not very, you know, hands on.
I'm not very hands and I waslike, oh, I need to, yeah,

(19:05):
outsource where possible, andwork smarter or not. Yes, yeah,
do the things you love and, youknow, automate the things that
you don't love. Yes, I love thatyou're right. It's time to play
another Would You Rather? Wouldyou rather negotiate with a
toddler mid tantrum and talkinglike big tantrum here, or a
stakeholder mid scope group. Sothis is an easy one for me,

(19:29):
stakeholder mid scope. Oh,

Karis Dorrigan (19:34):
by far, okay. I think Parenthood has made my
working life much easier becauseit's like, Oh, that wasn't so
challenging as I once thought itwas, yeah,

Unknown (19:42):
a bit more predictable.
The workplace is a bit morepredictable. Yeah, I can self
regulate. Oh, emotionalmeltdowns, yeah,

Karis Dorrigan (19:50):
most of the time.

Kavita Kerwar (19:52):
Oh, I love all right. Okay, let's talk a bit
about your career design.
And growth as a leader, because,looking back even at your
introduction, you've workedacross some several very
recognizable Australian brands.
What's guided you through thesetransitions? Look, you know, I'd
have to say, earlier in mycareer, not a lot guided me. I

(20:16):
really did just roll with what Idid. Well, just naturally, very
bold, yeah. And I just kind of,I did fall into product
management, you know, Idefinitely had a strength in
that area, and some advice totry my hat at product
management, which was sageadvice at the time, because I
had no idea what it even was

Karis Dorrigan (20:37):
quite a while ago now, yeah. And so early on,
it was follows, following wheremy strengths were. Then I was
really thinking about what I mypurpose and what I loved, and
that was probably not as nuancedas now. I love travel. So
working, you know, getting therole at Qantas was a huge career
milestone for me to really workon a company that was very

(21:00):
aligned to what I love and how Ican support people, enjoy travel
and enjoy life. And then, youknow, definitely has, I've been
much clearer on that now. And Ithink a big transition for me
was leaving Qantas, and I didreflect on what I really enjoyed
through in product managementand in the tech space, and when

(21:21):
I looked back on my time, thereit was post COVID. So, you know,
everyone was stood down, andthere was time to think. And so
I had really gone intoorganizations for a long time,
probably 10 plus years, comingin and driving change
transformation and movingorganizations from very output
to outcome, businesses frombeing project to customer focus.

(21:43):
So really, you know, as we allknow, bringing that product and
customer centric model intobusinesses, which is so
rewarding, but you know, to behonest, became really draining,
and the hard work, and it's allabout constantly changing hearts
and minds. And so I reallywanted to step out of that into
working for organizations thatabsolutely understand and

(22:04):
support and create cultures thatproduct can really thrive. So
you're spending more time doinggreat work, driving innovation,
building great teams, thandriving change. And so that's
where I am. Now. It's aboutthat's what I love. Maybe one
day I'll step back into thattransformation space. But it's
about working for companies andin product, we can drive

(22:25):
innovation and do great workthrough best practice, in terms
of that, you know, way ofworking that we all love. Yeah,
I think that's,

Kavita Kerwar (22:34):
that's a great response, because it sounds like
it's a very natural it was avery natural fit for your
personality, and you were verycomfortable taking those risks
and also moving through boldlyin your career. For those who
are perhaps a bit more unsure ofwhat's next, like like you
touched on reflecting back atyour time like post Qantas, What
signs do you think it's worthlistening to for someone who's

(22:57):
unsure of charting their career?

Karis Dorrigan (22:59):
Look, I think it's really important to take
the time to think about, youknow, what energizes you and
what in your role are youloving? And are you really, you
know, in flow and really excitedabout what are you really not
loving, and what's draining youand kind of sucking your energy.
And I think starting tounderstand your values if you

(23:20):
don't, and that can be really,you know, some people, yes, I
know my values. Of course,they're just, you know, of
course, I understand that. Andsome like, oh, I don't know
where to start. Like, what arevalues? And so I think spending
some time understanding that.
And you can do some reallyinteresting, you know, you can
go into the via characterstrengths, which is a free
online survey tool, which isvery well regarded, and kind of
understand your characterstrengths. Character Strengths.

(23:42):
Gallup does a great strengthserver which is more corporate
related, but it's, you know,backed by quite a bit of
evidence that can, I think it'slike $25 you can learn a bit
about your working style. And souse all of these data points to
start to think about, What do Ilove, what am I good at? You
know, what are my values? Andthen how can I align that to my
career would be, I think, a goodstarting point. I think

(24:02):
important technology also to mypoint earlier about my career
around transformation and thenmore product innovation. You
know, product and tech is sodifferent in Australia and so
different by organization, whichis why I think some people,
particularly probably early ormid career, like struggle a bit,
but kind of knowing if you are adelivery orientated product

(24:23):
leader, if you are love customerand you love innovation, or you
love translation and change,thinking about those buckets
will help you understand whatcompanies to work for, because
product and tech comes in somany different shapes and sizes
in Australia, and you reallyneed To find that fit, I think,
to kind of really enjoy yourcareer.

Kavita Kerwar (24:44):
Yep, I think that's great response. That's
something that I've reflected ona lot as well. Like, what I like
to do is I do like a bit ofresearch, because it's so easy
to get caught on in what haveyou done in the past that you
were good at and until you sitand unpack? Did you actually
enjoy it? Were you. You thrivingin it, or were you just running
on adrenaline because there wasa change milestone, and you were

(25:04):
just revving to hit thatmilestone. But understanding
your values and understandingwhat helps you thrive will then
help you make career choice thatalign

Karis Dorrigan (25:13):
strengths are so interesting, right? Because we
look at our strengths, but ifyou think about what a strength
actually is, it's something thatyou're good at, but something
that energizes you. So you mightbe good a lot of things, but
they actually are not a strengthbecause you don't enjoy them. So
I think that's a real Gotcha.
Yeah. I also find

Kavita Kerwar (25:29):
it interesting that at the start, you mentioned
you just fell into productmanagement, which often seems to
be the case, and you had perhapsa mentor the start of your of
your career journey. So how, Iguess my question is, has
mentorship played a broader rolein your journey, and how do you
mentor and advocate for others?
Now, you

Karis Dorrigan (25:50):
know, I think women probably have, well, maybe
it's a generalization, but Icertainly haven't had too many
mentors and sponsors through mylife. Probably I should have tip
to my listeners to kind of seekthose out. I actually have an
amazing mentor now, and I thinkwhat sets her apart she's not in

(26:10):
the business. She's an externalmentor. She's a great sounding
board, but she also helps mejust build self confidence in my
path. But, you know, I thinkwhat sets away at part great
mentors issues also in my cornerand takes action on my behalf,
right? So she might be opening adoor, getting me access to a
conference, and just doing morethan being a passive sideline

(26:35):
coach or advisor and actuallystepping and helping someone
lift their career, I think, iswhat really makes for a great
mentor. And if I reflect on mycareer, when I was managing
really large teams, it wasreally interesting, because a
lot of the entry level male teammembers would reach out for me

(26:59):
for a coffee, which isfantastic, you know, high
talent, great people. Lovesupporting people, but then the
most senior women would feellike they're wasting my time.
And so I think as women, we needto, when we think about our
career, not just do the greatwork. You know, work hard and

(27:19):
get the promotion. Work hard anddo all of that, but also invest
time in building relationshipsand finding your mentors and
believing that you are worthy oftheir time.

Kavita Kerwar (27:33):
Yeah, that's very powerful. And I remember hearing
a quote that someone said, Isyour advocate or mentor? Is
someone who speaks your name orspeaks of your achievements
highly in rooms that you don'thave access and it sounds like
you've, you've had someone who'sbeen able to do that for you.
Yeah,

Karis Dorrigan (27:49):
yeah, totally.
And then if I think aboutmyself, for me now, it's really
around and to that conversationaround, you know, the people
that are contacting you to haveconversations, I intentionally
will now reach out to people.
I'll say yes to some or all ofthose people that want to chat
to me, but I'll make sure I'mintentionally carving out time

(28:13):
for other people that probablydon't have the confidence to
reach out to me and help themthrough their career and see how
I can support them.

Kavita Kerwar (28:22):
Yeah, that's a great that's a great point. I've
had the same observations aswell, where I've had, like,
grads and like technical grads,where they had men who'd reach
out, like, quicker for eitherunderstanding if there was a new
opening in the team tounderstand, like, Okay, what
skill sets do you need? And thenyou'd have women who would be
very hesitant, and I hate that.
This is a generalization, butI've also seen it happen in the

(28:44):
workplace so often then I'mlike, this is a stereotype that
that's there, yeah,

Karis Dorrigan (28:50):
and I think, you know, if we we want to champion
the men and like, that'sawesome. I wish I had that, you
know, in a in a belief when Iwas younger in my career. So for
me, it's about supporting that,but then lifting the women up
and making sure that,particularly being a leader and
having the privilege to be in aposition to support people and

(29:13):
women and solo parents. As mykind of personal mission is to
say yes to the helping, youknow, the men moving up in their
career, but also bringing in thewomen to that conversation so we
can get that equity, thatdiversity, that balance of
supporting different people inthe workplace. Yeah,

Kavita Kerwar (29:27):
that's fantastic.
Should we play another Would YouRather? Oh, okay, yeah, okay,
okay. Would you ratherredo your entire LinkedIn
profile from scratch or give usa price keynote in five minutes,
but no slides allowed.

Karis Dorrigan (29:43):
Oh, 100% I would be doing my LinkedIn profile
1000 times over chat. GPT, me,I'm a planner, I'm a thinker,
I'm an introvert. So that is myworst nightmare, giving us a
speech, no slides in fiveminutes to. Prepare? Yeah,

Kavita Kerwar (30:00):
that's what I do as well. I'm like LinkedIn next,
I'll

Karis Dorrigan (30:04):
do it for like month, and I would extrovert. I

Kavita Kerwar (30:06):
don't think introvert. It has anything
to do with it. Like doing akeynote that's probably recorded
and streamed and you're notprepared. That's like the worst
nightmare. So

Karis Dorrigan (30:15):
you do that thing of nightmares for me, for
sure. So

Kavita Kerwar (30:19):
talking about your leadership,
my next question is about yourrole as head of product. So how
do you lead with both empathyand an eye on commercial focus?
Yeah,

Karis Dorrigan (30:29):
it's a great question, and I think something
that has certainly evolved as Ihave grown in my career, and it
can be really challenging,right? Let's be honest, I think
it's a really challenging thingthat we all face. From my
perspective, however, you know,we always start with a customer.
And so it's a really having agreat understanding of our

(30:52):
customer problems, ouropportunities and what is
happening in the landscape. Andso from my perspective,
everything starts in customer,from strategy through to feature
initiative, you know, anyoptimizations, but always,
that's the steel thread througheverything that we do. And then
with that, we layer oncommercial as well. So, you
know, commercial is also alwayscritical, and is really the

(31:15):
driving force behind what weneed to do. So at freely, we're
driving growth. And also, youknow, our goal this year is to
become a profitable business andbusiness. So we really need to
be very clear on what metricswe're moving and what are the
important metrics for us toreally change the game on. And
so I always look at both, but Ireally think about starting with

(31:37):
a customer and then makingdecisions based on the
commercial impact of what we dowould be would be, I guess part
one. I think the second thing isreally where you are in your
growth journey and how you'reperforming from a scorecard
perspective. And so if yourscorecard is all in the red and
the PnL is looking very sad,then you're going to be in

(32:00):
tactical mode to really driveall the commercial levers. And
you might feel, as a productperson, that your customer is a
bit lost. I always tell my teamis not lost, because everything
we're doing is through thecustomer. But we're probably
more in day to day mode than thebig vision. And then when we're
looking at our scorecard, andeverything's going really well,
we've got a lot of greens, youknow, we can make bolder,

(32:22):
riskier plays around drivingbigger customer ambitions that
we may not be as confident on.
From a commercial perspective,we think there's something in
it, but, you know, we we havekind of low to medium confidence
of our commercial outcomes, andthat's probably where we
certainly in freely will startto really push things. So we
have to have both of those viewsto make the right decision. From

(32:45):
a product perspective,

Kavita Kerwar (32:47):
how do you when you when you're driving your
product strategy, and I'massuming that this is not when
you're in technical mode andwhen your PNL is very sad and
unhappy, but when it's but whenit's a strategic vision. How do
you ensure that inclusion isembedded into your product
strategy from the beginning?

Karis Dorrigan (33:03):
Yeah, I think this is a great question, and
something, you know, I'm notsure if we do super well at the
moment and are reallyintentional about it, though,
you know, I think in consciouswe absolutely were, we were so
at freely. I think it's allaround, you know, who's at the
table, making sure that we havea diverse workforce, making sure

(33:25):
that our team represent and ourpeople sort of represent our
customers in many ways. And wehave, you know, diversity of
thought and innovation on ourproduct team would be kind of
part of what we're doing. Andthen when we think about
customer it's also about makingsure that we are we have a cross
section that includes and has aslice of diversity. So we're

(33:48):
thinking about the differentdemographics. We're making sure
we have people who might havemedical conditions that we need
to support. You know, we'remaking sure that we're selecting
our audience, that we're talkingto that represent those
different groups and can feedinto how we're building our
product. Yeah,

Kavita Kerwar (34:07):
absolutely. Is there a product decision that
you're proud of, something thatmaybe challenged the assumptions
or sparked a change or a shift?

Karis Dorrigan (34:16):
So at the moment, you know, I'm really
proud about something that'scoming, and so I can't share
everything about it, but it'sreally around, I don't think
it's about like I'm, you know,it's really around how we're
reshaping the industry and howwe're thinking about travel
insurance. One of our bigambitions is to move travel

(34:39):
insurance away from being aholiday tax that has no value to
a really meaningful product thathelps our customers, and we add
service and value for them andso, and if you look at the
travel insurance market, it'svery generic, it's very
commoditized. It's very muchabout the transaction. And then,
you know, hopefully they don'tclaim. And, yeah. Yeah, we're

(35:00):
all happy for a businessperspective, but we really want
to flip that and think about,well, how are we providing real
value to our customers, and whatdoes value mean to them? So
coming soon, we'll be thinkingabout, what does that look like
for us, and how do we start toadd value to our long term loyal
customers, which is going to bequite unique, I think, in the

(35:20):
travel insurance space, yeah, sokeep an eye out for free. Oh,

Kavita Kerwar (35:26):
very excited, yeah, thanks. Thank you for
sharing that. Yeah. I'm veryexcited to see what you do here,
because I recently traveledoverseas, and I had to, and I
was doing like, canine ring orsomething, so I had to, like, go
and get more cover, rather thanthe regular cover that I had.
And then you you notice, like,the different stages of cover
you can get based on theactivity you intend to do when

(35:46):
you're traveling. And I waslike, it's very transactional.
This, yes, duration of yourtravel, this is how much you
pay, and this is the activitiesit'll be interesting to

Karis Dorrigan (35:54):
see. Yes, I'm really excited about that,
about, you know, it's gonna bethe first wave of how we're
giving customers more value. Butthat's absolutely our ambition,
to continue to create more valueand more service offerings that
can can give customers what theyneed beyond just if something
goes wrong.

Kavita Kerwar (36:12):
Very exciting.
All right, let's let's sayanother Would You Rather? Okay,
would you rather manage yourteam? And I know we've spoken
about this before. Where aboutautomation, where every tool and
every process is AI augmented,or stick with something purely
human centered workflow, noautomation. I think I know what

Karis Dorrigan (36:31):
I'm totally doing, AI augmentation. Because
why do I do low value tasks?

Kavita Kerwar (36:37):
But you do know like, there's the risk of
hallucinations, like, Yeah, butthat's augmentation.

Karis Dorrigan (36:42):
So the humans are still there to do the
rational, to do the bigthinking, make the judgment
calls, but we're losing all ofthat low value work and using
our, you know, creativity andour minds for the impactful the
high outcome work, which I thinkis really important. Fantastic.

Kavita Kerwar (36:58):
Thank you. I think I knew very much. I would
have been very shocked if youwere like no humans will do
everything, please. Now, allright, we've touched on this in
some of the themes we'veexplored in the podcast around
the next generation of leaders.
What's something you know nowthat you maybe wished you had
known early on in your careerjourney.

Karis Dorrigan (37:22):
I think for this one, it's my leadership style is
my strength. Oh, you know,because I'm not naturally
someone with a lot of selfbelief. I've built that over
time. And if I reflect on mycareer, I've had moments I've
been told I'm a passive leader.
Moments I've been told I'm anaggressive leader, which is
interesting, but all throughthat, I think I was the same

(37:45):
leader, and that is absolutelyone of my strengths. You know
how I lead and build greatteams? So I wish that I knew and
believed myself earlier on in myleadership journey. What

Kavita Kerwar (37:57):
helped you build this belief? I'm just so
curious.

Karis Dorrigan (38:02):
I you know, there's not one thing, right?
It's age.

Kavita Kerwar (38:07):
You also do a lot of reflection, responses,

Karis Dorrigan (38:12):
yeah, reflecting. And, you know, self
growth. I do a lot of meditationto get that monkey mind out of,
out of my brain. I do a lot ofgratitude practices. So it's all
those little habits, right?
You're also

Kavita Kerwar (38:27):
very you come across as very data driven, like
the way you you've charted yourvalues and the way you've given
examples to our listeners, eventhe tools you also are very data
driven. I thank you. That's whatI you know, take I haven't had
those feedback. Appreciate it.
Yeah, it's very like, I love it,though, because you're
meditative, you're reflective,and you're very data origin so

(38:49):
you know exactly, and you'revery grounded. That's what I
see. That makes lovely.

Karis Dorrigan (38:54):
Thank you. Oh, my pleasure.

Kavita Kerwar (38:58):
Oh, because I guess one of my next
question was going to be veryearly on, early on in people's
journeys. It's quite daunting toswitch. Like, in your case, from
like, want us to say insuranceis quite, quite different
switch. So how do you buildconfidence for someone who isn't
familiar with moving into newroles? More often than not,
women in particular, seem tohave a lot of imposter syndrome

(39:20):
then leaps in. Do you have anytips for our listeners as to
what look

Karis Dorrigan (39:27):
I think there's one type like I have had a lot
of minor imposter syndrome andself doubt, but there's been one
standout moment that I had a lotof imposter syndrome. And if I
reflect on that moment in mycareer, you know, I was running
two I was doing two jobs at thesame time because it was a
higher phrase. I couldn'tbackfill a role there were. The
leadership structure was reallyunclear. So I was managing a

(39:50):
matrix team with four sponsors.
You know, I was really but.
Burnt out.

Kavita Kerwar (40:02):
That's a lot of expectation, yeah, and I

Karis Dorrigan (40:04):
was just pushing through, right? If I do this,
you know, it'd be great for mycareer, the business needed. And
I was just pushing, pushing,pushing, and I'd lost sense of
all my boundaries. Actually,that was a moment that I've
became much more clear and myboundaries because I won't ever
let that happen again. So if Ithink about that, and I think
about imposter syndrome, it'sit's going to be larger and more

(40:25):
pronounced when you're not yourbest self, or when you're burnt
out, or you haven't taken thattime to reflect, or you're not
doing the things that you love,you've stopped going to the gym,
you've stopped doing yourmeditation, whatever it is that
you do. So I think my advice, ifyou're really feeling an
imposter syndrome is to justtake a bit of a check, like, are

(40:46):
you okay? Do you need to doanything to get your foundation
set? Whatever that looks likefor you. So me, it would be, you
know, meditation, going to thegym, you know, maybe just taking
a mental health day from work,resetting right, whatever that,
and that's gonna look differentfor every single person. And
then I think you can be muchmore objective with with that,

(41:08):
and you've just got to challengeyourself, because imposter
syndrome is just telling youryou not to do something that's
might be a bit scary, or you'redoing it for the first time. So
it's a natural response. I thinkyou've got to challenge your own
internal dialog, which sounds soeasy, but it's not right. Yeah,
one,

Kavita Kerwar (41:27):
one piece of advice I heard from someone
recently. It's exactly this.
It's like, get off the hamsterwheel and reflect. But also,
when you're reflecting, don'tbeat yourself up because, yeah,
don't be critical. And if youare receiving, if you're in an
organization that sends lots ofemails, and you have any emails
that say, Praise your work orlove your work, save those.
Yeah, I love it because, becausethen you go back and go to your

(41:49):
kudos folder, I am not, you knowwhat I think I am. Look at all
this data. Look at what peopleare actually saying I'm doing,
and the value that I'm adding,and that helps. So you can look
at data and be like, No, I amYes,

Karis Dorrigan (42:05):
I am fine. And have your support people, I
guess, to extend on that in amore you've got your data, then
chat to people that you trustand get their feedback, or just
get your girlfriends to lift youup. Yeah, and I do, I also do
love a bit of self compassion.
So it's like, well, I alwaystell myself I'm a great mom. I'm
doing a great job. I have agreat home, you know, you got to
tell yourself these things,yeah.

Kavita Kerwar (42:29):
And to your, you know, your description of the
scenario, it sounded like fourdifferent sponsors. It would be
stressful for anyone. So, yeah,just Oh, totally. It's the
environment as Yes. So it isgetting off the hamster wheel
might help you get it from adifferent line. And

Karis Dorrigan (42:42):
often I would say imposter syndrome is
probably more about theenvironment than you. Oh, right.
Because if you're in asupportive environment with the
right people, with a greatleader supporting you in that
step, you're probably not goingto have imposter syndrome or to
be much, you know, won't beloud, yeah,

Kavita Kerwar (42:59):
yeah. Thank you.
I think that was veryinsightful. Should we do our
last Would You Rather Okay?
Would you rather be known as avisionary leader who pushes
boundaries, or a steady leaderwho builds rock solid teams?

Karis Dorrigan (43:15):
I would rather be known as a visionary leader.
Oh,

Kavita Kerwar (43:19):
okay, because we think about

Karis Dorrigan (43:21):
my values are an adventure. Yeah, I love
innovation. I want to changethings. That's why I love
freely. You know, I want tochange travel insurance for the
better. So, yeah, you know, Iwant to, I want to contribute to
a better world and create greatexperiences for customers.

Kavita Kerwar (43:35):
Oh, fantastic, yeah. Thank you. Thank you very
much for your time. So welcome.
Thank you. This was great. Thankyou very much. Lovely to chat.
Yeah.
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