Chris Castle: An extraordinary journey, from Partnerships to Engineering
23m 44s
Chris Castle’s journey from a sales and partnership role in adventure travel to becoming a full-stack software engineer at Get Your Guide reflects a deep passion for using technology to enhance real-world experiences. Initially drawn to the travel industry through roles at Intrepid Travel, he discovered a personal fascination with how technology could solve customer and supplier challenges. After recognizing the growing tech momentum in travel, he embarked on a self-taught transition into engineering, supported by a culture that values learning, trust, and risk-taking. His manager’s early assurance that mistakes are not personal failures, combined with access to mentors and hands-on coding opportunities, helped build his confidence and paved the way for a successful career shift. Today, Chris works in the guided experiences team, focusing on improving customer booking journeys and multi-day tour experiences—projects rooted in both technical innovation and deep industry insight. He also plays a mentorship role, guiding others in transitioning into tech roles by sharing practical advice and soft skills. Beyond work, Chris cherishes travel experiences like gorilla trekking in Uganda, which exemplify the deep connection between human experience and the products he helps build. His journey underscores Get Your Guide’s commitment to empowering employees with autonomy, growth, and meaningful impact across its platforms.
My manager, on my first day basically said,
if as a junior engineer or like someone new to engineering
and new to this whole thing,
if you mess anything up, it's not your fault,
it's our fault for not setting up processes
that kind of catch this and coaching you
or like just simple processes that aren't picking up
that we're about to deploy something that breaks.
So that sort of relief and support was really appreciated
and from day one that kind of eases you a little bit.
- Hi, I'm your host Liam and this is Behind the Journey,
a show where we explore the inner workings
of Get Your Guide by Talking To Our,
incredible leaders about their journeys, ideas and strategies.
For those who don't know,
we're a market leading company on a mission
to connect millions of travelers
with unforgettable experiences all over the world.
So if you're looking to embark on a new career journey
and the thought of revolutionizing
the travel experience,
sector sounds exciting to you,
head over to GetYourGuide.criz.
And today I'm joined by Chris Castle.
He's one of our software engineers
in the guided experiences team.
In addition to his strong technical know-how,
Chris has a truly fascinating career journey
fueled by curiosity and mentorship.
So let's get into it, Chris.
How are you doing?
Welcome to Behind the Journey.
- I'm very well, thank you.
Thanks for having me.
- No, thanks so much for joining.
First of all, I want to kick up with a proper introduction,
but I want to start with some context on how we met.
So I had the pleasure of helping to hire Chris
in his first role here,
which was four years ago.
- Yeah, 21. - I think so,
towards the tail end of the pandemic.
- Yeah, that's right.
So it's been a while that we've known each other.
So thanks for coming.
And for the benefit of our listeners,
maybe just tell us a little bit more about your background.
- Yeah, sure.
- So taking it all the way back to when I was studying,
I started out in finance and accounting.
And after three years of doing that at university in the UK,
I realized I never wanted to do it again.
So did the typical late teenage early 20s thing
of going traveling for a little bit,
working a couple of local jobs in my hometown.
And then after that moved down to London,
and was kind of applying for anything
that I felt I could be passionate about.
So I was looking at industries like films and movies,
sports and travel,
which is ultimately where I ended up,
but was fairly scatter than in my approach.
There wasn't any particular intention with it,
like plotting a career path
or taking on a grad scheme or anything like that.
And just happened to get a job
at a really cool adventure travel company
based out of Brixton in London.
That will be with intrepid travel,
one of our suppliers here at Get Your Guide, actually.
And spent multiple years there in the UK
and in Toronto, in Canada.
So got offered a transfer there
and over this time I was working a bunch of different sales,
marketing, partnership roles.
And it was actually in those roles
that I got to learn about Get Your Guide
when I was based in Toronto.
One of the accounts that I actually managed
for the business was Get Your Guides.
So I got to know a few of the team members
in the New York office and the San Francisco office.
Some people that still here today, actually.
And that was my first introduction
to What Get Your Guide does as a business
and the culture and the values
and how you worked with supplier partners.
So actually saw it from a different angle
than a lot of people have seen it from.
And then yeah, over the years of just doing sales
and partnerships work in the industry,
I reached a point where I didn't feel like I was learning
too much and at the same time,
the travel tech side of things was exploding
and you see all this exciting innovation
and product work happening.
And I also love the supplier side
and the operating side,
but wanted to, yeah, kind of immersing myself
more in the product and tech world.
And at this point, I had like no technical background
or skills and started to self-teach
just via online courses and YouTube and things like that.
So then just some basic HTML CSS and JavaScript.
And basically got just good enough
to glide an interview with a tech company.
So then after working at Intrepid Travel
for about five years, the pandemic hit.
And after about 18 months of working part-time,
hours because there wasn't really much of a demand
for operating adventure travel trips around the world.
At that time, I started to pursue my next role
and knowing get your guide and knowing the people
that worked here was a really appealing place to work.
So I reached out to a couple of people
that still work here today and flowed with a couple
of roles to them and they actually pointed
me in a different direction into a role
with the connectivity team as a connectivity partner
business manager, which is kind of a count managing
the API integration that we have with supplier partners.
It was a half technical, half commercial role.
So I felt like it was a good way to have one foot
in the world that I knew quite well,
like the sales and commercially side of things
and then also be able to upskill on the technical side.
Yeah, that makes sense.
And that was about the time that we met.
But initially, you didn't apply for a role in Berlin.
I remember you applied for a role in New York
and then ended up in Berlin.
- Yep. - That's right.
- Yeah, at the time I was living on Vancouver Island,
this beautiful island off the west coast of Canada,
but my visa was tied to a Canadian job
and after being there for about four years,
I was open to where I would work next.
I was applying for things in London, in New York,
in San Francisco was kind of open to where
the next move would be.
And the connectivity role that I was just talking about
was based out of the New York office.
So I applied there and two or three interviews in.
My, at that point that would have been my future manager
said, have you ever considered Berlin?
And at that point, I definitely had an idea
if she was referring to Berlin Germany
or like Berlin, Ohio or somewhere.
And my girlfriend was like in my peripheral vision.
And I think she overheard it.
And I'd like wondering why Berlin was coming up in conversation.
So yeah, it was a bit of an unplanned move to Berlin,
but it worked out for the best in the end.
We're very happy here.
And I also had a great interviewing experience
with yourself.
Yeah, I felt very well looked after in a way
that I hadn't had before in any other role or company.
So that kind of really put down a marker for how
you guys like to operate taking care of candidates
right from that first interaction through to onboarding
and then obviously working here.
Nice, great.
Thanks for talking us through that.
So you've had a very interesting career journey
four years at Get Your Guide now from that first role
that you talked about in the partnerships team.
But then moving to the tech team as a full stack developer.
So just maybe tell us a bit about what inspired that move for you.
When I started out in the industry, which is now like eight
or nine years ago, you can feel a distinct difference
to where it's at today.
And I think operators are a lot more tech enabled
and the offerings customers are like so much more complex
and frankly, better.
And you can just feel this like momentum shift
and the excitement of being able to use technology
to create something and put it out into the world.
And that was the kind of thing that appealed to me.
And still does feel to me is that with a few lines of code,
you can push something to production and see it on the site.
And then in our case, like millions and millions of people
see it and like even like your friends are using the product
and family using it.
And she's like, oh, yeah, I did that.
And then you hope it works and still hopefully it does.
Yeah, and that's kind of what attracted me in the first instance.
And when I first joined Get Your Guides,
as I said, my role was hybrid commercial and technical.
So I was having a lot of conversations with internal engineers
and external engineers at other companies
that we integrate with.
And I just became more and more curious
about how the technical side works.
And it felt like with those tools,
you could also have impact if you're
able to create new things that customers can use.
And it also just satisfied.
It's kind of internal curiosity to like know how things work
and working out the logic is like quite personally satisfying.
which is quite opposite to where what I was doing before in terms of
relationship management and a lot of Zoom calls and a lot of soft skill stuff
and yeah I think having that blend and sometimes mixing those skills and
balancing them out is quite appealing I suppose. So obviously it's a big move
right completely different department, different teams, different colleagues so it
just been interesting to hear about what has your experience been with the
Imposter Syndrome like what support systems have helped you build your
confidence moving into a new team as a software engineer? I found myself
enjoying the technical side of my role more than the commercial side in the
relationship management side and after about six months into my career with
Get Your Guide I started to seriously consider doing bootcamp so kind of
learning to be hands-on with code and ultimately with the aim of
becoming a software engineer and that was daunting for a number of
reasons obviously it's a career change which on the face of it is always a big
decision I had only been around for six months with Get Your Guide so it felt
like it would have been too early to say like I want to do something
different now and I guess the thing that sticks out about that time was the
level of support I had internally and making that decision I was quite scared
to voice this because of the reasons I just mentioned but my manager was
super supportive she was like okay how do we make this happen it wasn't even a
question of like what it might be in short term for the team if they have to
find someone new or anything like that it was this is great super ambitious
let's figure out how we can make it happen I learned that there were already a
handful of people internally that had done the same sort of career switches so
was able to speak to those people as well even outside of Get Your Guide like I'd
built up a number of friends acquaintances in the industry and I was able to
call some of those up like some that run tech companies some that are like tech
adjacent and they are all happy to offer their time and advice and pretty much
everyone said yeah just just go for it like what's the worst that could that
could happen and I was even able to start writing very simple bits of codes to
support the team that I was working on which I think goes to show the level of
trust that the business and management place in people with these ambitions
that you're able to try new things and take risks and you'll have the support
to do that and that's even before you know you've been rubber stamped with any
training or you've got a natural role so that opportunity to dabble really
spurred me on and encouraged me to go and do a bootcamp for six months which I
did part-time so it was like Tuesdays Thursdays in the evenings and then
four days on Saturdays it's a quite an intense period when I first moved to
Berlin but I loved it it never really felt like work at the time and it was a
good way to meet new people around Berlin and yeah that led to junior
engineering role great thank you so much and you mentioned obviously as well
that you weren't the first person to make a move like that and get your guide
but I was just interested to hear you know moving into such a different team what
is your experience been with I can post a syndrome like what support systems
have helped you build your confidence as a software engineer yeah it's
something that I don't want to say struggles with because it has like negative
connotations I think it's completely natural to feel uncomfortable in brand new
situations where you haven't got a lot of experience to to fall back on it's
something that I still deal with today but I think a couple of the things that
made me feel really comfortable particularly at the start of my engineering
career were that my manager on my first day basically said if as a junior
engineer like someone new to engineering and new to this whole thing if you
mess anything up it's not your fault it's our fault for not setting up
processes that kind of catch this and coaching you or like just simple
processes that aren't picking up that we're about to deploy something that
breaks yeah so that sort of relief and support was really appreciated from day
one that kind of eases you a little bit in that sense and I have always
believed in having strong mentors so I've always been quite intentional and
kind of selective I guess on who my mentors are so usually lists down a kind of
profile of mentor that I'm looking for so it might be that I want to learn
XYZ or looking for someone that has done this before or has this certain type
of personality or career path and then if I don't know someone like that I'll
just ask around yeah so I'm happy to ask my manager or their manager or
something like that until you kind of get a good recommendation for someone
that is happy to mental you and happy also perhaps with something you can
give in return that's been really beneficial in terms of just having
someone in your corner someone that you can bounce ideas off someone that you
can be completely honest with as well outside of your day to day about different
situations in your team or something with a fresh pair of eyes and can share
all their experience and fill in some gaps that you naturally don't have
until you've been through yeah a bunch of different situations yeah that makes
sense and myself I mean I've been here not quite but almost 10 years so I can
safely say obviously that you know I feel that we're accomplishing the
champions the opportunity to grow your career in many different directions I've
seen happen with so many people I did it myself I was a joined originally in
care I was a lead for a year and then moved into another role as workforce
manager and it was only after two years in that role that I well been thinking
about it for a long time I think like you had as well but with a little bit
nervous of making the step but then moved from caring into business recruitment
and I've been this team now for like just over six and a half years and you
recently starred in a video about your journey which is great by the way
thank you and listeners you can find it on LinkedIn and on the get your guide
you to page so do you feel like you now mentor employees you help them with
their career shifts into tech and you just tell us a little bit about how you
help your mentees forge their own path yeah and linking back to what we were
talking about before around imposter syndrome it still feels quite uncomfortable
for me when someone comes to me and says hey can you help me with this all
like I saw you saw you did this and I'd like to learn how you how you do that
because yeah it still feels quite strange that people are coming to me for
advice and I don't feel like qualified at all to be in that position but
over time you realize when you're talking to different people that everyone has
different skillsets different experiences and naturally with my background in
sales and marketing and partnerships I have a lot of soft skills and project
management skills and things like that that I can share with people that haven't
had that sort of experience and coming to yeah realize that everyone has
something different to offer had been really helpful in that as an example I
recently had a candidate actually I don't think you were his interviewer but he
reached out to me from after applying to a job in Zurich as an associate he
reached out to me over LinkedIn and just asked like a few questions said he'd
actually read one of the blogs that I did a couple of years back for the
employer brand team and yeah that was kind of nice that someone had read it
and decided to apply and was able to share a few tips about the interview
process isn't it and he actually starts on Friday all right great so like and
that was a result as well as seeing the video but you are you ready maybe but
that was like a super fun thing to do as well like I'd never done any acting
before and it was definitely different to what I my usual day today but a lot of
fun and yeah super well organized and good to share my story and my mum was
also happy with it oh my last she still has no idea what I do when people ask
is she says he works with computers which I think he's close to that you
clearly do yeah yeah it's a bit more near to it yeah she does like the friends
of family discount too so she understands that part of so does mine yeah that's
amazing thanks so much and just be great to hear like you've been in obviously
you've transitioned a while on into the new team so how things are going right
now any projects that you're working on that you're particularly excited about
that you could share with them yeah so a few months ago now we launched a series
of new teams within get your guides around growing specific verticals
So my team is responsible for guided experiences.
So pretty much anything where as a part of the experience you have a guide.
So it might be a walking tour around the city, food tours, day trips, that sort of stuff.
I'm really honing in on the problems customers face when trying to book one of these tours.
You know, what do they want to know about the guide before they book?
What do they, how can we make the transportation aspect smoother?
Yeah. Things like that. So we're only a few months in.
We're still staffing up.
So we should have another couple of eyes joining us in a few days.
But it's all things considered. It's going great.
We are also doing this as I said across four different teams.
So there's like four teams staffing up at the minute and all trying to get up to speed on different projects.
We have actually a cross team boat party on Thursday.
So we've got four teams heading out on the water and hoping for some good weather just as a way to try and bring everyone together,
build some culture within our in our group.
And yeah, start delivering on some cool projects.
I think the one that I'm quite proud of recently is the work we did around multi day tours,
which is a type of tour that's close to my heart because I worked on it for multiple years at previous roles
and with different suppliers around the world running three day trips, four day trips up to two weeks or even beyond that.
So we're able to reshape the experience that customer seeing on the front end and the same for what our suppliers are using to supply the content on the supply side as well.
So really proud of our work that we're doing that.
Yeah, I can imagine it's great.
And I think it's also great as well when you listen to someone from your team, to yourself in this instance, talking about the focus is always around improving customer experience,
or whether it's the customer taking the tour or if it's a supply partner involved in it.
So thanks for talking us through.
Lastly, we always like to finish up with our shared passion, favorite subject, which is travel.
So interested to hear what was your most unforgettable travel experience?
I guess the first day I landed in Berlin, I did bump into Euliam at the big garden near the office.
Yeah, so that one remember that.
Yeah, that was a good way to land in Berlin, but outside of that, I think my favorite travel experience ever.
I was lucky enough to do some gorilla trekking in Uganda a few years ago.
So that's where you spend a day with the local rangers hiking through the forests of Uganda looking for families of gorillas.
And you get up super close, so four or five meters away.
And it feels very primal to be that close to something as.
Yeah, amazing as a family of gorillas.
And you see the silverback being his chest and giving out a roar and it kind of makes it his tingle.
That can imagine.
Yeah, exactly so that one is hard to beat.
Sounds amazing.
Books with Get Your Guide, I assume.
Yeah, of course, of course.
Great.
Chris, thanks so much for taking the time to chat with me today.
Really, really appreciate it.
No, thanks for having me. It was a lot of fun.
Good to hear. And if you want to learn more, you can check out behind the journey on all major streaming platforms for more episodes and insights into how we're working to revolutionize the travel experience industry.
Podcast Summary
Key Points:
Chris Castle transitioned from a sales and partnership role in the travel industry to a full-stack software engineer, driven by curiosity and the desire to create tangible tech-driven experiences.
His early career at Intrepid Travel and exposure to Get Your Guide through partnership work provided foundational industry knowledge and introduced him to the company’s values and operations.
He pursued a career shift into engineering despite lacking technical background, supported by his manager's trust and a culture that prioritizes learning, risk-taking, and early-stage experimentation.
A key factor in his confidence was the company’s supportive environment, including the explicit reassurance that mistakes are not personal failures but systemic gaps that the organization will address.
Chris emphasized the importance of mentorship, intentionally seeking mentors who could provide diverse skill sets and perspectives, especially in navigating imposter syndrome.
He now mentors others in transitioning to tech, sharing both technical and soft skills, and helping new hires navigate career shifts with confidence.
His current focus is on improving the guided experiences product, particularly in customer booking flows and multi-day tour experiences, which align with his prior industry experience.
He highlights the team-building efforts, such as cross-team boat trips and new verticals, as critical to fostering culture and collaboration in the growing guided experiences team.
Summary:
Chris Castle’s journey from a sales and partnership role in adventure travel to becoming a full-stack software engineer at Get Your Guide reflects a deep passion for using technology to enhance real-world experiences. Initially drawn to the travel industry through roles at Intrepid Travel, he discovered a personal fascination with how technology could solve customer and supplier challenges. After recognizing the growing tech momentum in travel, he embarked on a self-taught transition into engineering, supported by a culture that values learning, trust, and risk-taking.
His manager’s early assurance that mistakes are not personal failures, combined with access to mentors and hands-on coding opportunities, helped build his confidence and paved the way for a successful career shift. Today, Chris works in the guided experiences team, focusing on improving customer booking journeys and multi-day tour experiences—projects rooted in both technical innovation and deep industry insight. He also plays a mentorship role, guiding others in transitioning into tech roles by sharing practical advice and soft skills.
Beyond work, Chris cherishes travel experiences like gorilla trekking in Uganda, which exemplify the deep connection between human experience and the products he helps build. His journey underscores Get Your Guide’s commitment to empowering employees with autonomy, growth, and meaningful impact across its platforms.
FAQs
Chris was supported by his manager who emphasized that mistakes were not his fault, and that the company was responsible for setting up proper processes and coaching. This created a safe environment to learn and grow.
He found comfort in knowing his manager would support him, and he actively sought mentors with relevant experience. Over time, he realized that everyone has unique strengths and that his background in sales and partnerships offered valuable soft skills to share.
He was drawn to the excitement of creating products with code, seeing real-world impact—like millions of users benefiting from new features—and the personal satisfaction of solving technical problems.
Chris deliberately sought mentors with specific expertise and experiences, and he found that talking to both internal colleagues and industry professionals helped build confidence and provided practical guidance.
He is focused on improving the customer booking experience for guided tours, such as helping users learn about guides and streamlining transportation. He is also proud of work on multi-day tours that enhanced the experience for both customers and suppliers.
He initially applied for a role in New York, but during interviews, he was suggested to consider Berlin. The move was unplanned but ultimately beneficial, as he and his partner now live and work happily in Berlin.
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