Today, I’m joined by a co-host: the wonderful Gaby Howard, Head of Growth and Operations at Carted.
Laura Nicol connects with today's co-host: the wonderful Gaby Howard, Head of Growth and Operations at Carted.
Gaby’s no stranger to the podcast—she first appeared on Ep 23. Gaby Howard on Navigating the Shift from Founder to Operator in Tech: Insights from Carted and Flaunter, where the wonderful Paloma interviewed her about her journey from founder to operator. (If you’re here for her backstory, head there first—we’re not retelling it today.)
This episode is something different: a pulse check. A water-cooler moment. The kind of chat Gaby and I usually have off-mic—only this time, we hit record.
If the noise of the internet lately feels like a never-ending hamster wheel, you’re not alone. In this chat, we cover:
Huge thanks to Gaby for jumping into the co-host seat. We hope this chat feels like the water-cooler moment you didn’t know you needed.
Want to connect with Gaby? Find her on LinkedIn.
Connecting with Gaby Howard, Head of Growth and Operations at Carted:
[Note: This transcript is AI-generated via Descript. Please expect typos]
[00:00:00]
Laura: Connecting with Gaby Howard, head of Growth and Operations at
Carted.
today. I am welcoming a co-host to the podcast. Welcome, Gaby. Welcome
Gaby. So, Gaby's been on the podcast before. The wonderful Paloma
interviewed Gaby way back when in episode 23, where Gaby shared her
founder to operator story.
if you're here for the stories, we won't be recovering Gaby's story today. So
head back to that episode, And today we're here for more of a pulse check and a
chat similar to Gaby, and i's private conversations. So expect a water cooler a
moment, a conversation between two operators, almost like a mid-year
temperature check on how we're feeling in our roles and what we're excited
about. You'll hear me being a bossy host, Gaby and I finding our [00:01:00] feet
as co-hosts, and we'll be talking about, am I ahead behind keeping up? These
are feelings that operators are feeling right now.
These are the questions that our listeners are asking, and if you're looking for
answers, same here lately. The internet feels like a hamster wheel of noise, so
Gaby and I jumped on the mic to compare notes.
Huge thanks to Gaby for joining me in the co-host seat and hope you enjoy the
episode.
Gaby Howard, welcome back to Calling Operator for the second time in your
life.
Gaby : Thank you. Thanks for having me. What an honor.
Gaby : and it's a nasally version of us both because we're both coming off the
back of a packet of Strepsils and the flu.Laura: Yeah. this episode was sponsored by Strepsils. Not
Gaby : it is. It is flu season. Mm-hmm.
Laura: season and last episode, I spoke about burnout and going slow to go
fast. So we hope we give you a moment of pause in your day. But [00:02:00] if
you want to hear Gaby's story, Paloma who was our ex host you last year for
episode 23, Gaby Howard on navigating the shift from founder to operator in
Tech So if you wanna check out Gaby's operator story that's where to go. And
today it's just more of a general chitchat.
Gaby : Yep. I like it.
Laura: So if you had to explain who you are in one line though, just to give our
listeners a view of who is Gaby,
Gaby : Ooh.
Laura: you say?
Gaby : Oh, who is Gaby? I can give you my title. I'm head of ops and growth at
Carted. who is Gaby? I'm someone who's very passionate about building,
companies. I love the zero to one space, from nothing to something, that is like
my happy place that I have found through the discomfort of feeling incredibly
uncomfortable in that space.
but I love the challenges. I love solving challenges, for brand new companies.
Gaby : I think that's because. I really love connecting with people and I think
the early stages of [00:03:00] a startup, you are just connecting with people left,
right, and center with your team, customers.
All of those early conversations, really kind of deeply involved in solving a
problem from a people perspective, from a human perspective. So I think that's
probably my passion space.
Laura: It's a unique time of building that you get exposure to so much,
Gaby : Yeah.Laura: the hats, but that means that you get that exposure
Gaby : Yes, exactly. I love wearing all of the hats. I do love being involved in
as many aspects of the company as I possibly can be. that doesn't frighten me. It
really excites me. I think this is the stage of a company where you can have, if
you love that role, you can have the biggest impact because it is about
connecting all of those dots in the early days and just trying to see things that
others might have missed to give yourself a head start to give the company a
head start.
Laura: So you are leading growth and ops For those that dunno, Carted,
[00:04:00] what's the one liner and what stage is Carted
Gaby : I've been at Carted now for three years, around three.
Laura: It
Gaby : we are building, yes, it has been three years. Yes. I suppose, in terms of
financing rounds, we are a seed sage company. we are building out a shopping
graph, We have been working really hard at solving the very big problems in
the shopping space. This is not a one sentence, introduction to carted, so I'm
gonna just roll with this.
so we're solving really big problems in the shopping space, and that is really,
really challenging. But our point of view is that we are doing this very much
from the perspective of the shopper. So a lot of the work that's been done, in the
e-commerce, shopping space has been largely for the benefit of merchants.
and we think there's a really huge opportunity to shift the perspective and to
make everything shopper first. so we're building out a shopping graph and on
top of that shopping graph we have built out the Carted [00:05:00] app, which
some people listening here might be using already or know of.
And that is our consumer facing product that sits on top of our shopping data,
product data, and our shopper insights. and that I would describe as your
ultimate wishlist app. You can save any item from any store, and then we give
you insights on those items. So we give you price drop notifications, we give
you stock notifications.And if you are a shopping lover like I am, this is all music to your ears. because
you can add all of the products that you want from any store and actually just
wait for Carted to serve you all of the valuable information about those products
so you know what to buy and when to buy.
Laura: Bing, bing, bing.
I love it. I also love that we both come from a fashion background as well. It
just brings me so much joy.
Gaby : Yes, I'm
so happy to be here. I love our product. I know that the line is you don't build
for yourself, but this really feels like, it's not me technically. It's not me,
physically building it. [00:06:00] So it feels like it's being built for me.
I love, love, love the product that we've built, and I'm really passionate about
the space that we're building in. because I do think that there is just a huge, huge
open, massive opportunity to make shopping so much better than it is today.
And I love that we're looking at it from a very different perspective to anybody
else.
Laura: very excited to dive into some of what you've been building later on in
the show, but just to give everyone some context of what we're gonna do today.
we're gonna start off with a bit of a self-reflection. Then we are going to zoom
out slightly and do a bit of a pulse check on what's happening out there for
operators and some of the pain points that we are hearing. we're gonna share our
year so far, a little, mid-year reflection.
We're coming up to the end of June yeah, we just wanna look back, but then
also look ahead in terms of where do we wanna be standing, when our
companies hit their next inflection point.
First question is, are you finding interesting about yourself at the moment?
Gaby : I feel like to come back to the point that you made [00:07:00] earlier, it
feels a little bit like I've come full circle, the past few years, or maybe not, so
much the last 12 months, but before that, the role that I was in was probably
much more the one that I thought that I would be in when I first started at
Carted.it was more operationally heavy and I have found myself in the last 12 months
really leaning into the roles of marketing, sales, partnerships, and out of the
more structural kind of roles, and structural work that I was doing before that,
and I love it. I remember when I first started at Carted, someone said to me, oh,
Gaby, you are going in an ops role.
Are you sure that's where you want to be? And I was like, well, yes, of course.
I've thought deeply about this. This is what I wanna do. This is my next step.
But I think about him and that comment a lot recently because [00:08:00] I do, I
love what I'm doing right now. And it is less, as I said, is less about the the
finance, the legals, you know, all of that kind of work that I was doing.
A little while back. And it really is more about like talking to a customer,
whether that's through marketing, whether that's through sales, whether that's
through partnerships, it's just talking, connecting with people, and building out a
brand, which is what I have really loved to do in the past 12 months.
So yes, I feel like I'm back to my roots, which is in partnerships, pr, sales, and
that is what I love to do. So that has been interesting, an interesting experience,
and it has put me in a very happy place.
Laura: Yay to happy Gaby. Do you reckon that's where you spiked when, when
you were a founder as well?
Gaby : Absolutely. a very organized person. I am very action oriented. I am all
of the things that I guess on paper, make me a good. Head of [00:09:00] ops, but
I think the things that I love to do, my happy place is in the work that I'm
currently doing now, which is actually, funnily enough, slightly less organized,
a little bit more hectic, a little bit more from the heart and the gut.
and I'm happy to be here
Laura: And on a more personal note, what's energizing you outside of work?
Gaby : energizing me outside of work. I think it's back to writing, and I know
we have spoken about this several times. What do I wanna write about? and I
have found the space to write in and I think that is something that is really, is
making me really happy.
there's also a really nice balance a family and work that I seem to have found,
and that just makes everything feel like it makes everything flow so much moreeasily. and I really do. I love my work. I obviously love my family when work
is going well and I feel happy at work, it really does impact the rest of my life.
When I feel a bit frazzled and on edge at work, [00:10:00] again, like I, I think
that flows through. So I think it's just a nice, at the moment, I have just a nice
equilibrium. I know I'm doing the work that I love to do when I'm still thinking
and dreaming about that work
at night and on weekends in a healthy way, caveat in a healthy way.
I just generally, I feel like I'm doing work that feels easy. if that makes sense.
What about you? If I were to flip the question over.
Laura: I think it's obvious from my last episode, I'm in a moment of self
discovery and self-growth. And in a period of my life where there's so much
change, I am just doubling down on really learning lots about myself. I feel like
there's a few things that I'm enjoying. I'm enjoying showing up vulnerably and
with openness as a leader. And kind of bringing the team along on that journey
and leading by example, whether that's everything to do with feedback or
whether that's just communicating trade offs. I'm really enjoying [00:11:00]
with my partner. It's been something that we've been working on for a while
now and it's so amazing what great communication does.
You know, like we do it for work all the time, but my partner and I have set up
these three weekly check-ins, and at the beginning of the conversation We have
to pay each other a compliment, and then it's
Gaby : Yeah.
Laura: what's going on in your world this week or today? And then it's a piece
of feedback.
So if you want to give your partner feedback moment, that's the time, the
designated time to give feedback. So the other one's not caught off guard, et
cetera. And you just have to listen and not respond. And honestly, I'm just like,
these moments in our world are so life changing. I know this is a podcast about
operating, but if anyone needs any couples therapy tips, there you go.
Gaby : That's really funny that you say that because it is also something that we
have been working on too. Oh my gosh. Look, there's too much information
coming from us, but as a [00:12:00] couple, it is also something that we havebeen working on this year, and it is dramatic. We are not perfect at it yet, and
we haven't structured it in the same way that you have in terms of like organized
check-ins.
I've let it be a little bit more chaos on my end, you know, just to see how that
goes first. but yeah, it's incredibly transformative, good communication. I was
listening to a podcast actually about this on one of Lenny's podcasts. oh, I can't
remember the operator's name.
Yes, it was, we. And I was listening to it and I was like, yes, this is, all of this is
applicable at work, but also at home. so I'm very happy for you.
Laura: Yeah. it's so good. And then the last piece, I guess on that thread of
learning more about myself, I am part of a community called the Glue Club in
the States. I feel like I mentioned them in
Gaby : Mm-hmm.
Laura: but it's a community of operators. So obviously that lights me up. And
we've been doing this assessment called Sparketypes. So I know there's lots of
like personality tests out there. [00:13:00] But this one's been great to almost
understand the impulse behind what you do. so essentially you do the test and
you come out of a primary sparketype a shadow sparketype, and then an antis
sparketype. And essentially what that means is your primary like how you show
up in the world. So mine's the maker It's all about creativity, innovation and
bringing ideas to life, which like you were saying at the beginning of the
episode, I feel like I'm love building in that zero to one and it's helped me
understand that I can almost like apply that anywhere.
It doesn't have to be early stage zero to one. It actually could be any part of a
big project, et cetera. the shadow sparker type is living to learn and I am just a
learning machine and I love getting handed a task like we were saying earlier,
go and fix this function because it's not operating well.
It's not working, the cogs are not turning. there's an antis, sparker type that is the
performer and that's just something I'm not very
Gaby : Oh,
Laura: at, which is so interesting. 'cause [00:14:00] one of the many reasons
why I host the podcast is 'cause I'm shit scared of public speaking.So very interesting that I do not come to life when I am building experiences, et
cetera. So yeah, I just think it's so interesting to learn deeply about yourself.
Gaby : I like that shadow. That's nice.
And so are you better at public speaking now for having done the podcast? are
you more confident?
Laura: definitely.
I think about how I communicate more. I think about the message that I'm
trying to deliver more. I'm conscious of filler words even though I do still say
them. put me up on a stage at Toastmasters though, and I'm shit scared again. So
I need to get out my protective phone booth.
Gaby : You do. It's very gray in there, Laura. It's very gray.
Laura: It's, so
Gaby : Okay, so then I think this is something that we touched on before, but
I'm not sure if you answered the question. What do you [00:15:00] define an
operator to be? I mean, we throw the word around a lot. What is your
definition?
Laura: my definition is essentially a company builder, you are like the
operational engine behind a founder's vision. IE you are this vision and finding
ways to bring this. vision into a strategy and then rallying a whole organization
behind it. I do actually believe that operators come in all shapes and sizes and
different functions. so I don't necessarily feel like they need p and l
responsibility, but
I guess, especially as the chief of staff, like working closely with an executive
and helping bring this vision to life. But I love the analogy of you're the cogs in
the machine and the cogs in the engine. Turning thing because I think when I
have Maxine Minter, my boss, who I always mention on the podcast, she said
that you are essentially like building a [00:16:00] system. And that system is run
by people and you're building the system in which the people can operate. And I
feel like that's very much like if you take the COGS analogy, you're building
this engine and everything needs to be operating succinctly for this to be a good
company.
Gaby : I like the cogs too.technically everyone's an operator, right? do you agree with the statement?
Everyone is an operator in a company?
Laura: I think they can be 'cause you are contributing to an outcome I guess
where the different size and a definition for the sake of this podcast is that
there's a lot of content out there to help founders and there's a lot of content out
there to help investors. However, there's not
Gaby : Okay.
Laura: really focused on that operator level. And I feel like we as operators
hold a lot of context and wear a lot of the shit essentially, we also are the people
that have to [00:17:00] have a brave face and show up each day. We can be
vulnerable, but we have to show up and steer the ship. So I do think there's a
certain level where you just show up as an IC and you just get the work done.
I'm interested to see where the ecosystem takes this in terms of a proper
definition.
What are your
Gaby : But the, yeah, I think it depends on the stage of the company.
I think I would probably argue that the smaller the company, the earlier the
stage, the more you need. Yes, there are moments where everyone is just an
individual contributor, everyone's an ic 'cause you're just turning, you need to
turn through some work.
but I think companies that have all of the team with an operator mindset at that
stage of a company, in such a better position, it's such a stronger position.
Ultimately, you are a team of problem solvers and you all understand the
machine. You all understand the cogs and how they turn, how they should
[00:18:00] turn, where they're not turning.
How you might resolve a problem in engineering if you don't work in
engineering because you understand ultimately, the kind of basic arithmetics of
the company. And oftentimes there are complications that come in every shape
and form, but there is a very basic arithmetics
And if you understand that, then you are better prepared to leverageLaura: it's almost like you are a systems builder and this may be very British of
me, but I know that you have IKEA in Australia as well. We don't yet in New
Zealand, how do we not have
Gaby : You don't?
Laura: No.
Gaby : Oh, wow.
Laura: but I just almost see it as like picking up an instruction manual and
building a piece of flat pack furniture
you know, like anyone can follow that regardless of the level and the outcome is
to have a lovely home.
Gaby : What a nice outcome. It's so simple when you put it that way. Laura,
what are we even doing here?
Laura: Exactly.[00:19:00]
So next we wanted to. focus on a bit of a pulse check of the ecosystem and what
are some of the pain points that we're hearing out there in the market. I was very
fortunate enough when I was in Sydney to host a Calling Operator and Notion
coffee get together. We had no agenda. It was just a shared guest list. Show up
as yourself and meet somebody in the room that's either solving the same
challenge as you, or that you just haven't had a face-to-face connection with. I
think the Australian ecosystem and New Zealand is very, very small, but we
don't get those curated operator moments. I think what was really interesting is
firstly, everyone was just so pumped to go to an event that didn't have an
[00:20:00] agenda and just connect, which I. It's crazy, isn't it? That you're like,
What we're seeing is operators are trying to become these organizational
inventors, creating new ways to scale, delegating work, executing because the
existing playbooks don't really match current reality. this is spanning everything
from. Direct oversight and managing people, learning to delegate to systems
and experts that you can't really control. IE you've bought on someone
fractional or you've bought on a contractor because you don't have that
headcount. Or you're trying to learn a new AI system and see how you can
reduce operational efficiency by 50% if you're me. job descriptions becoming
more meaningless. we as operators are being fluid adaptive to just expand into
roles the business actually needs, which is so exciting, but it's causing thisidentity crisis of who are we, what are we doing? Yes, I find [00:21:00] joy in
this work, but am I an operator?
Am I a marketer? Like who am I?
Then there's this big shift of can't scale by just hiring more people. we're really
betting everything on leverage through systems. And I think the last one was
around relationships becoming a core infrastructure for us to be good at our job.
So what does
Yeah,
from you from a list of problems that operators are currently facing in the ANZ
market?
Gaby : I really do think that these are the same problems that we have always
faced. the existential crisis I. Maybe feels more acute, I'm not sure, but maybe
it's because we're talking about it more. Maybe it's just externalized. Before it
was more internalized. Personally, I've always thought about these things a lot.
I've always had these stresses in terms of what to do and deliver. I think I've just
never talked about it so much. I've never talked in such detail about am I a
[00:22:00] generalist or not? where am I spiking? who am I in the context of
work outside of, I'm someone who enjoys solving problems.
Here is a suite of problems for me to solve. There will always be problems to
solve, and how do you just lean into that and enjoy being a person who can
thrive in that kind of environment? this environment is not changing anytime
soon. So it's kind of like a lot of founders talk about when they first start a
company, it's like, oh my God, it's everything and all at once.
And I have no idea, but all the ideas, I have a 20 year long vision. I can see a
future, but I have no fucking idea where to start. All of those things exist and
they have always existed. And I think potentially what you're describing is
operators just getting closer and closer to the core problems, and the core
responsibilities of how to [00:23:00] make a company a product, a success.
these are always the problems. They're always the challenges. People, whether
your people are powered by systems or not, you know, like how you get the
most out of somebody is always going to be a challenge, a really exciting one
now because you have different tools at your disposal.but I still think we look at all of the same challenges that we have from 5, 10, 20
years ago. They just feel amplified and there is a lot of noise out there. And oh
my god, I have been on LinkedIn a lot at the moment. For various reasons. And
there is a lot of noise in these platforms about so-called experts or you know,
big ideas.
And every release from every product under the sun is game changing and
everyone prepare themselves, you know, like it's do or die. And I think if you
just kind of start to cut out that noise, focus on what you're doing in your
company, focus on the outcome they're [00:24:00] actually trying to achieve,
the flow will come.
if you just give the problem, the energy that it deserves, we are as operators, I
guess the best position to be able to try and approach those challenges and solve
the problems.
Laura: And maybe it's like the maturity of the ANZ startup ecosystem as well,
that. We just haven't really been speaking about this at the operator level, and
it's just happening inside companies.
Gaby : There's also a very big culture of everyone trying to optimize and
operationalize themselves. I think yes, that's great, but I think there's also value
in, calming the firm a little bit on that. I, I mean, yeah, don't stress, if you are
not the perfect operator or if your system isn't perfect or if you don't have a
system.
the challenge is actually enjoy solving the problem. Get stuck in the problem.
Laura: [00:25:00] I think there's a real fear around playbooks that we've maybe
been following until now are becoming more
Gaby : Yeah.
Laura: to follow. So
Gaby : Yes.
Laura: then you look to the big wide world of how are other people solving it?
And that's why you pick up so much noise as opposed to going into like a cross-
functional experiment mode of the business rhythm and how are we keeping the
business moving andGaby : Yes.
Laura: to be running internally, how does that feed into our strategy?
How does that feed into our culture? And I think
more and more exposure across an organization, like every function I'm seeing
now for larger companies Like they've almost got an ops person for each
function. 'cause we're having to
Gaby : Yeah.
Laura: our workflows and embedding them of tooling, et cetera. Which again,
isn't new, but the emphasis on that is new. And I think the more and more
exposure we're getting. The more we're like, ah, like I'm really interested in the
people space at the moment. I'm like, I find it
[00:26:00] fascinating,
Gaby : Yeah.
Laura: but how can
Gaby : Mm-hmm.
Laura: work the best place to be in the world? And I know this is
Gaby : Mm-hmm.
Laura: There's so many companies out there that say, work's not work, blah,
blah, blah. But I really do think there's an opportunity there to bring human to
work first, then have this amazing environment that people can just flourish. I'm
like human first.
Gaby : First, you're like, this is your big reaction to the machines.
Laura: Yeah.
Gaby : breaking out of the cog system.Laura: Yeah. But then I think the machines need to be there so then we can be
focusing on the highest leverage work. But I think it's just taking it back to
basics. And at the end of the day, to make a machine work for you or to make
any human work for you, you need a process 1 0
Gaby : Mm-hmm. Mm-hmm.
Laura: just taking the fear-mongering out of that.
as I'm experimenting with AI agents right now, I keep getting scared and I'm
like, why am I scared? I am to solve a problem with a new tool [00:27:00] and
therefore I'm gonna run
Gaby : Yep.
Laura: whole load of issues because I can't code, but there's AI to teach me
how to code. Like how amazing is that?
Gaby : Yeah, it is amazing. I think also the fundamental part there is, is this a
system that I need to build? Is this still serving my company? you talked about
playbooks kind of feeling like they're disappearing. and I agree. And so back to
the creative thinking back to, okay, what are the fundamentals?
what am I trying to achieve? The world has changed or is changing, am I still
building these systems or do I need to build completely new systems? Like am I
don't need to just replicate what I've been doing for the past couple of years. it's
actually starting from scratch. And I think that's really exciting.
That feels really liberating to be like, okay, let me re-look at this function. Let
me re-look at this job. Let me re-look at this, KPI that I might have, what is it?
what really is [00:28:00] going on under the hood, and how do I change what
I'm building?
Laura: It's almost like we just need to put on a different tint of glasses and just
Gaby : Yeah.
Laura: things on its head.
Gaby : Honestly,we can all feel great about the fact that, we're all in the same boat.
Laura: Yeah.
Gaby : is in the same boat. Everyone is feeling this, and we're all starting again.
Laura: we are. which then brings us all back to the network as an operating
system piece I think this is why we're really leaning into network because We're
craving people that are going through, like people that are in the mud, trying to
solve it You know, how are you solving it?
Gaby : and the people has always been there, like the human connection. I think
for a long time, maybe we just didn't invest in it
much. Personally, my human connections have always driven me further than
any kind of systems and processes. I think it's always been my people
connections that I have leaned [00:29:00] on.
To help guide me. and I feel really comfortable there and I think we should feel
really comfortable there and we should create that network effect, and lean into
that.
Laura: And I think working in a small company, like I've had to do that to have
a team, right?
I say had to build a peer network, but I am remote in New Zealand. If I didn't
build my own peer network, I would actually still be quite lonely in my role
when this
Gaby : Yeah.
Laura: and platform has given me an opportunity to meet people like me, you
know, I really feel like they're the everyday operators just figuring shit out.
Gaby : And then you do it together. Obviously
Laura: Exactly.
Gaby : everything feels much more comfortable when you know that other
people are going through the same struggles.Laura: I guess that's a bit of a pulse check on what's happening out there. I
think a key takeaway is this whole, Am I ahead? Am I behind or am I missing
something? I think
even as a statement to like really journal or try and work out what that looks like
for you would be really helpful [00:30:00] because I think we are getting
distracted by the noise. And we just need to get our heads
Gaby : Yeah. I 1000% agree with that. There is so much noise and there are so
many people out there thinking or positing that they've got the answers or
they've found the solutions, and it's really easy to fall into the trap of feeling
behind, oh my God, all of these people talking about all this stuff that they
know and they've tried and they're doing, and.
That's just not true. It's just not true. Like everyone is in the same boat.
Everyone is still learning. And I think it just goes back to be a problem solver
and lean into the thing that you do well and lean into your ability to kind of
think creatively around a bigger structure. To be able to find, those small tweaks
that can actually make a big impact and one step at a time.
And fundamentally, what is the problem that you're trying to solve what is the
desired outcome? we're not just going to go and create some new [00:31:00]
systems you know, to replace old systems because the whole structure has
changed.
Laura: And also Leverage this as a moment in time where you are actually
gonna get more support than ever to do your job, regardless of if that's human or
machine. And it's just breaking that down as to like actually, what are the needs
of the business and what does this workflow look like and where do customers
need a human service and where do they not.
Gaby : And How much time will I invest in building out a new system?
knowing that I don't know how to do that yet.
Laura: and
what's really gonna move the needle for the business this quarter?
Gaby : I still think that there's a really interesting conversation around how do
you build the team that's gonna drive these changes, I think, and then you know,
fractional, offshore, where your team is. one of the learnings from Carted hasbeen a tight, smaller team can accomplish [00:32:00] more when you are all
kind of ready to be on the same page when you're all on the same page.
And having all of that context internal at the company, versus external or
fractional like it's really hard to get someone who is not 1000% in the company
to be an equal partner in building.
I just think that has been my experience this year. whether, fractional
employees, whether outsourced, whether, agency, the challenges feel really,
really big. And so the closer that you are to all of the context of the company,
the easier it is to meet the challenges I suppose.
Laura: Yeah,
Gaby : I don't know.
Laura: there's actually a lot of fractional folks that listen to the podcast and
one, of them described it at the event as I'm the bandaid that can help you get
from
Gaby : Hmm.
Laura: And then once you feel
Gaby : Yeah.
Laura: that, like without the risk of a [00:33:00] full-time employee headcount,
once you feel like you've got that, that's my job done. I think we're in an
exciting time where we can really design teams around a problem and a scope
of work quite creatively wherein before we've been, I guess, limited to the
headcount that we've got on the team, the skillset that we've got on the team,
where're in, we can really like co-design some creative outcomes.
Gaby : I just think it is so important to invest the time upfront for context
building.
and I think a lot of people miss that part. the person that you bring into your
company for a short period of time or to do one specific role, you have to get
them up to speed as quickly as possible for them to be able to kind of work their
magic.They bring some skills, but you have all of the context and I really don't think
that people spend nearly enough time, downloading that context to. [00:34:00]
Fractional or part-time team members, they don't spend nearly as much time as
they should.
Laura: closing the fractional piece, it'll be interesting to see how that plays out
because I don't think either of us have the answers to that yet, a lot of people
that we're speaking to don't necessarily have the answers to that yet.
Gaby : Yeah, absolutely. And I think to your point, it is the opportunity to build
a company in the exact way that you want. The design of the company is so
flexible, and I think it's also a great way to bring people in who you may then
want to work. They may be your full-time team member soon enough, or not.
But I think being able to be flexible and fluid with everything at the moment is
just the optimum position to be in.
Laura: And I think we'll see it happening with AI more and more that like
people will bring in like a fractional CMO who's ran X projects in AI to then
come in, do a audit of the function and help the team set a new [00:35:00]
strategy
move on to the next company. I think there's lots of opportunity there
functionally, which is actually really exciting.
Gaby : Yep. Yep.
Laura: So that's I guess, a bit of a sense check of what's happening in the
ecosystem right now with our listeners, specifically, we know that there's gonna
be more problems but just from that Notion meetup, there are some insights.
let's reflect on our own years. I'd love to know Gaby, given that we're in June,
we've had a whole half, I dunno how we're at this moment. what has your year
looked like so far and what's worked, what didn't? Where did you grow?
Gaby : Oh my goodness. I also can't believe that we're in June. I feel like I say
this every year. It just flies by and then I'm like, oh my God. what did I do? and
it's very hard to go back and unpack all of the micro wins and the macro.
personally, I love that I have found a space that I feel really excited and
energized by in the business.
how amazing to have [00:36:00] the opportunity to create that space for myself,is something that I think about a lot. To be able to design my role and also to be
able to, see and acknowledge when my role needs to change shape, and actually
action be the,
Laura: a question on that?
Gaby : yeah,
Laura: what indicators have you spotted to recognize that your role needs to
change its shape?
Gaby : that's a good question. I think it's just the needs of knowing the
company inside and out, and knowing where we need to be. one of the things
I'm good at is like seeing how what we do in the next short term impacts that
longer term vision.
and I do have. I am very action oriented.
I don't wait around for a long time to think about what the next move should be.
I trust, I do trust my gut a lot. I don't know how to wrap that up in a bow and
hand that off to somebody else. [00:37:00] but I think it's just seeing what's
happening with the business because you just know the business. You just know
the business so well.
Um, you know your team members so well, you know where other people can
lift and where you can kind of hand over. and I know what I bring to the team
that is different from all of the other team members. And when I can recognize
that's something that I need to like double down on, then I give myself the
permission to do that.
it's just the freedom and the trust with working in a high performing team like
this to just say, Hey everybody, I can see this. Opportunity here, or I can see a
hole that needs filling and this is something that is my, like sweet spot, so I'm
gonna go and do that. I guess there will always be competing priorities and it's
being good at, just triaging those and thinking, okay, I will have the biggest
impact over here in this place.
At the moment, the challenge for me is the impact It can feel longer term. it can
feel like a longer term investment. the work [00:38:00] that I'm, some of the
work that I'm doing, it feels a less, less immediate.it's then having, the team that's kind of like, yeah, we're gonna stick by that
decision and we are going to invest there.
It's an investment. Just going with that until you feel signals that it is always,
isn't working.
Laura: if you had to be specific, what's working Well?
Gaby : I really think our investment in our brand, our community, our
connection with our customers is working really well. And I think that is
something that is hard to build very clean systems and processes around. A lot
of that is still in this kind of early growth phase. A lot of that still feels very like
human.
It's human centered. but I love that. So I feel, happy with that. the things that I
am working on and learning to do better are building more performance based
systems around the things around growth, around trying to build in, I guess
[00:39:00] scalability into what is typically feels kind of hard to scale.
so that is something that I'm focusing more on and I'm enjoying doing. But I
think that only comes with doing the very like one-to-one work.
Laura: for clarity, that's for performance, people systems.
Gaby : that's for customer systems actually. And that is a place that I have
really loved leaning into. it's for our users.
Laura: Nice. Nice.
Gaby : Yeah. How about you? Just gimme a second. Oh my goodness. Running
a tight ship. Everybody. Laura is running a tight ship fast enough with the
question asking.
Laura: So good,
Gaby : She is the boss of this podcast, so I, I'm trying to do my best. I'm
learning.
Laura: so good. I'm definitely cutting that bit out.Gaby : Really? Are you? Which one will you say? So ask me the question,
Gaby, now please.[00:40:00]
Laura: Please ask me the question, Gaby.
Gaby : Okay. Tell me about yourself, Laura.
It's like we're dating. Okay. No.
Laura: for context for our listeners. Gaby paused and I was just like, ask me.
So I'm getting very excited about
Gaby : Yeah. Yeah. So are you, has it been fun? Has it felt different?
Laura: it's kind of crazy because usually I'm learning about somebody's story, I
know you so well, but just trying to make sure that that comes through to the
listeners so that they know you well, but knowing that that resource already
exists. yeah,
Gaby : Yeah. Yeah.
Laura: you for being here.
I'm really loving it as an
Gaby : I hope this experiment isn't a flop. I hope it's a great success, but if it is,
we can always iterate. I mean, it's only step one.
Laura: Exactly. Listeners, let us know what you think.
Gaby : but I did say that we needed to do this because you have so [00:41:00]
much intel. You have spoken to so many people now. It's time that someone
asked you the questions because it just feels like you are very smart at this and
you have a lot to say, but you often don't have as much space to kind of say it.
Laura: I quite like it that way.
Gaby : if you're going to get up on Toast Masters, may be this, back and forth is
a very important part of that
Laura: I know, IGaby : practice.
Laura: I've actually put Toastmasters on pause 'cause I think I've got enough on
at the moment. it was one of the decisions I made just in case I needed to be
accountable. to answer your question, so I've been at co Ventures for two and a
bit years now. And it's all about building fund one. And I feel like we're in a
really exciting moment that we found product market fit. And any operator
listening to this that's found product market fit, it's like, yay. But then it's like,
okay, let's scale this beast. So we're in a moment in time where I just feel like
my areas of responsibility are so wide, [00:42:00] but I have to go so deep in
each of them.
Like as an example, partnership and co-pilot to Maxine. I'm leading product, I'm
leading our brand and comms, I am leading our platform and portfolio support.
So obviously Maxine is our wonderful investor on the team. but just like in
terms of how we're operationalizing the portfolio support, and we've now got 26
companies that we've invested in out of fund one. So how do we keep making
sure that they're getting the support that they need and we host thought
partnership calls, which they absolutely love. so founders can choose. The
cadence in which they meet us. And we use that call to unpack one of their
biggest problems or opportunities and just serve as thought partners for them.
And it really, it makes me feel so close to the customer because at the end of the
day, our customer the founders that we work for. And I've just really loved that
experience. And in half two, I've got a big project coming up to build our
platform that will almost like scale some of that [00:43:00] support around the
founders. So it is been like a really interesting moment in time of sitting in, in
those calls, helping problem solve and also just getting that fly in the wall
exposure and experience to building companies. So I've really, really loved that.
leading our special projects. Sometimes that fits into these buckets. Sometimes
they don't. we are gearing up for a fundraise for Co Ventures for Fund 2, which,
which is probably, not a public facing thing to say, but we are doing it and it's
exciting and building the infrastructure to set Maxine up for success for that
fundraise as well. But then having such wonderful and positive feedback on
Fund 1 from our investors and the venture partners that help us support the
companies and the founders that we support. It's just been an amazing journey.
So I feel like what worked is almost like I. to this point and getting to this
moment in time where we've got pull from the market. I would say, in terms of
what hasn't worked so well has just been a learning journey for me.
I think in terms [00:44:00] of when you've got such a wide scope as an operator
and really you were to split down my role, I'm holding functions together andthen having to, execute in such a deep level for those, it's just been such a
journey to understand how to manage.
Gaby : How do you, what is your day to day or week to week?
Laura: Yeah,
Gaby : how do you manage it?
Laura: it's been a constant iteration on a calendar skeleton in terms of like how
I plan my week and the iterations have all come from failures. Of dropping a
ball, you know, something that's just like, oh, this isn't working, or this isn't
landing well with the team. But I think right now I've just got blocked deep
work time. I'm fortunate enough that I don't too many meetings. I probably have
half a day to a full day per week of meetings, and not always on the same day,
but that gives me time for a lot of deep work. And I just have to be [00:45:00]
ruthlessly diligent on what I prioritize. I spoke about this in the last podcast, but
we use a tool called Sunsama, so report on what I work on each day. So every
time I plan my week for the next week, I have that system of record of what I
planned for the previous week. And if it's not done, I am just learning more and
more to like raise like, Hey, this is moving from my agenda each week. Does it
need to be escalated? Do I need to work in collaboration with Maxine on what
we actually put down in order to stand that up? And then you have your things
like portfolio support. You can't plan that. So it's like customer support. You
can't plan that. You just have to jump in. And I think one of the products that
I've built that. We will be hiring for a role for that shortly, which is amazing, is
for our syndicates. We run a sidecar, so a different investment vehicle for
people to co-invest into the companies that we work for, alongside the fund.
And that's been a product [00:46:00] that has been building out this angel
community angel investors, and giving them exposure to pre-seed deals. it's
really been taking me back to my marketing comms PR roots of we've gotta get
a decent CRM infrastructure and you know, all those pains that you're like, how
am I solving this in 2025?
Gaby : Oh, the old CRM, it's an ever present issue.
Laura: if
Gaby : Yeah.Laura: a favorite CRM, I'm still trying to solve this issue, so please give me
your CRM suggestions. And like, I think learning what tools to build from
scratch and what to just buy off the shelf has
Gaby : Yeah,
Laura: a big one this year. And in terms of where I've grown, I think my self-
awareness and, really seeing every iteration as an opportunity to learn and love
learning and it's just really, I guess analyzing where I'm finding joy in my work
and where I'm losing energy.
and like I've said it a couple of times again, so I'm sorry that I'm being a broken
record here, but I am really learning that. [00:47:00] Being a great operator
comes with all this self work and I feel like I'm in a real deep moment of work
almost like I'm just setting my foundation, to ultimately be a world class chief
of staff.
Gaby : Fabulous. If you had a bigger team,
where would you position yourself and what would you be doing more of?
Laura: If I had a bigger team, I would probably be across the same scope but
not as deep in.
Gaby : Yeah.
Laura: Execution. Like I always want to be executing, but I'd probably be
doing a lot more making and like leaning
Gaby : Yes.
Laura: maker superpower of mine. whether that's like prototyping a new
product that we can, roll out to our portfolio companies.
I feel like I'll have a lot more time for strategic projects that have a real
Gaby : Hmm.
Laura: so I think I would still be across the same scope. I just wouldn't be as
deep in the delivery. WhatGaby : Yes. I think I would say the exact same thing. back to your point, I feel
like I could be on customer discovery calls all day, [00:48:00] every day
forever. that is such a happy place. I love it. but yes, less deep in the execution.
still absolutely across all of the functions that I currently am and across as much
of the work as I am.
But yes, less deep in execution so that there's more space to think. maybe
special projects is a good way
Laura: Yeah,
Gaby : describing it.
Laura: So say 12 months time when carted hits its next inflection point,
Gaby : Hmm.
Laura: do you almost wanna be standing within that company at that point in
your ideal world?
Gaby : In my ideal world, well, in my ideal world, we'll have built team, bigger
team and we'll have made excellent hiring choices along the way, and we'll have
brought in. Brilliant collaborators. I think the direction for me is more around
this idea of having the bandwidth to do these, uh, more creative thinking, the
bandwidth for more special projects to have in place the people who can
[00:49:00] execute, on the vision from the perspective, not necessarily just the
company vision, but from the perspective of the marketing comms customer.
we have an incredible head of product at the moment, but building an amazing
product side by side with an amazing story around that product and just having
that team to execute and the flexibility and the bandwidth to be special projects.
I'd still like to stay really close.
To the customer, to the shopper. I still like to stay really close to the storytelling
and crafting the brand. I think that is a moat for companies these days. it always
has been. I think, maybe more people will agree now than in the past. and I
really, really look forward to the challenge of creating the best brand ever at
Carted.We have users already, you know, who love us, love the product, and you can
tell [00:50:00] they have an emotional attachment to Carted. And I think, that's
the nirvana. So to show up for them and to continue showing up for them in a
way that resonates, will be really, really satisfying for me.
Laura: Yeah, that's awesome. Yay.
I think for me it will be that we've successfully raised a fund two. And so then
we're supporting that next cohort of companies that are coming into the fold and
I guess successfully from a, like how we've executed, how we've built trust in
the market, you know, all of the brand creds that come with that. but then
like setting Maxine up for success for like a really great, enjoyable fundraise.
they're hard, they take you off the business, right? with that, I think comes
almost like a result of my work. like a scaled platform in which we then support
33 from fund one plus fund
Gaby : Mm-hmm.
Laura: companies.
And how we tackle that next challenge of being [00:51:00] their most helpful
VC and giving them the most relevant resources from pre-seed to seed and like
really helping see what impact we have. Like we're only starting to see our first
few companies now raise their US seed, so we're still so early we only invest it
pre-seed. So just even seeing that cohort of companies like coming through is so
exciting. I guess like where I wanna be standing is like right there with the
founders that we support. And as part of Fund one. We gifted 5%, carry to the
founders that we work for. So I'm excited to see what Fund two will start
enabling us to do in terms of impact for the industry and the folks that are really
doing the building day to day.
So I think just lots of vibes.
Gaby : As a founder who's been at that stage, I remember so vividly, I mean it
was when I was so new to everything, the introductions that were made and just
how impactful having other founders and operators [00:52:00] in the same stage
of life as me, as in company life, not necessarily personal life, but company life
that was and still is.That's what we are talking, we're talking about here now with operators is the
superpower. it's the glue that kind of keeps you sane and together and you kind
of grow as a cohort.
Laura: Yeah.
Gaby : I found that really, you know, impactful and that's what you are doing.
Laura: Yeah.
Gaby : I love it.
Laura: can that
yeah, I'm just excited to be part of the growth of the A NZ ecosystem and I
guess learn, by doing really, and growing alongside great people and this
community.
Gaby : An amazing community that you and Paloma have built.
Laura: I know. Thank you. Paloma. Oh, one thing I didn't mention was like
almost becoming like say in a year's time, Leo, when I interviewed her for this
podcast, she said the role of the AI workforce manager would come up. And I
would love to almost see that playing out in my role a little bit that I [00:53:00]
I don't directly manage people in my role currently, but then imagine if I had
this workforce of AI agents helping us operate.
And I see that as a really exciting to give our team scale. So shall we finish up,
Gaby : we shall, let's finish up
Laura: your, what's your final note?
Gaby : my final note. we went into this conversation looking at you know, all
of the challenges that everyone is facing. I'm actually really excited. I've never
felt so. Invigorated by my work. That's such a terrible word. What is it better
than invigorate? I don't know. I actually just feel really excited about the stage
that we're in.
I feel really excited personally because I think these are challenges that I really
enjoy. I love being inside the challenge. and I think this is the time for growth.and I'm really excited for that growth. I'm really excited for the next 12 months
because with the growth of the company, I can [00:54:00] see how I can
continue to grow.
and into that kind of moving from that, zero to one to that next phase of a
company and seeing what all of those challenges, what that experience brings.
So, yeah, this is a really exciting time for me. I'm not so scared about the
outside world, because it is as it always has been, it just feels maybe more acute
because we are tuning in to maybe the wrong things or too much.
so just taking a step back from that, tuning in and just focusing on first
principles.
Laura: I
think for me, I would plus one that a scale journey. two, continuing my quest to
be human first and my favorite phrase, and yeah, just really enjoy the ride with
the right boundaries in place to help me sustain this pace
Gaby : Mm.
That's a really good call out. I think getting better at those boundaries.
Laura: Yeah, definitely not recording a podcast when we're both sick.
Gaby : Who said that? I'm always this [00:55:00] husky.
Laura: Okay. Well thank you so much for tuning in. You can find Gaby
Howard on LinkedIn. Please connect with her and myself, Laura Nicol on
LinkedIn too. Thanks, Gaby.
Gaby : Thank you.