SPEAKER_00: 0:01

Hello and welcome again to Your Next Big Thing. My guest today is Sarah Pollan. Sarah, welcome to the program.

SPEAKER_02: 0:08

Thank you so much for having me, Neil. It's an absolute pleasure to be here.

SPEAKER_00: 0:12

Yeah, you know, I was so fascinated after our conversation at the Alphalist CTO event in Hamburg. I asked if you have done podcasting and public speaking before, and I was thrilled to read some of the interviews you've already given about the topic of career change and career reinvention. So I'm going to give a quick introduction. And then I think our listeners who are interested in career reinvention, building a bridge to your next big thing and also becoming more senior and being really intentional about seniorizing yourself in the industry are really going to benefit from this episode. So thanks for being here.

SPEAKER_02: 0:51

No, thank you. That's what it's all about.

SPEAKER_00: 0:54

So Sarah Poland successfully retired from a career in opera and she leveraged a coding boot camp to land in information technology and IT security. And now several years later, she built a career path to the field CTO role at HashiCorp, a global provider of infrastructure as code and other solutions that is very well known in my industry. And I became fascinated to know how she successfully reinvented herself from opera to IT security, and then truly to leadership because the business competencies, people leadership, organizational leadership that she is now so effective at. are a really interesting story that I think we can all learn from. So on the personal side, Sarah, like me, is originally from the US. She's hailing from Western Colorado, and she spent five years in Paris before now being based in the Netherlands, near Amsterdam, if I'm right. And she works with global teams, including in Ireland. So Sarah, welcome again to the program.

SPEAKER_02: 2:00

No, thanks for having me.

SPEAKER_00: 2:02

We talked not only about professional topics, but also about pet ownership and pet sitting in careers in pet sitting, so that will have to be in the extra episode that we do afterwards. I wanted to put Sarah on the spot, first of all, for something that is both a highlight and a lowlight in anyone's career, and that is, you know, you took the decision to retire from opera after five years in the industry, extensive studies. What was that like for you? Was it a roller coaster? Take us back to that decision.

SPEAKER_02: 2:34

I think anytime you do a major career pivot, and especially opera, it's your identity. You eat it, you breathe it, you sleep it, and it's a passion on top of being a career. to make a decision to walk away or to change your life so drastically. I think there's a certain amount of grieving that happens, a certain amount of understanding that you do have to let it go, but it's not an easy thing to do. So it had been, particularly the lifestyle was really challenging. I had two really small kids at the time. And being able to manage that and the kind of chaotic schedule with the kids and the uncertain income, it just was no longer viable. And so I remember walking in for an audition, doing the audition. I think I missed one note in the song, and I watched the director just cringe. And at that point, I was like, you know what? And this is just, it's not what I want to do. And if this is the reaction for something like that, when the rest of life is happening and they're bigger things, then I don't think I want to be a part of this anymore. And so at that point, that's very much when I just said, okay. It's time for me to walk away. It's time for me to start kind of figuring out what else I want to do. But it was, what, probably about a three-year gap where it took me to, yeah, it took me about three years to really understand where I wanted to go from there and how my skills that I had accumulated over time could really be used and what could I leverage to have a successful career.

SPEAKER_00: 4:07

My last career reinvention took about 18 months and I had some setbacks, some moments of questioning and reorienting And so, yeah, I wonder what was it that helped you overcome and get to the other side in that three-year transition that you talked about? What was maybe a breakthrough that you had?

SPEAKER_02: 4:27

I've always loved to solve problems. And whether they're like business problems or just... you know, kind of life problems. I love taking it and looking at it from a different perspective. How can we do things differently to make sure that we end up at an end point that we really think is valuable or bring something to the table or solves, you know, the problem at hand. And so I had taken just a job working in H.R. because they needed the language skills. So I said, okay, yeah, let's go ahead and do this. And I sat down and was literally filling in contracts by hand, you know, address, number of hours. I was like, there has to be a better way to do this. This is like...

SPEAKER_00: 5:13

Good old data entry, yeah.

SPEAKER_02: 5:15

So I started thinking about, okay, how would I do this? How would I go about this? And so I started looking at... just VBA initially, because that was the only knowledge I had back in school. You know, it was like Excel links into VBA. So let's see, like, what are my options?

SPEAKER_00: 5:29

I speed this up. It's a macros going. Yeah. Yeah,

SPEAKER_02: 5:32

exactly. That was, I feel like I don't want to sit here and just type like four hours every day and a bunch of names. And, um, then I started looking at, okay, well, there seemed to be also better ways to do this. So like take a look at Python, for example, or, um, and then I just, opened that rabbit hole and went down that rabbit hole and started thinking, well, okay, if you can do all these things to solve a document issue, what can we do to solve some other problems and some other business problems? And so I was like, okay, well, coding seems interesting. And then as fate would have it, got put on this big IT project for HR. And I was like, oh, this is fun. I think this might be something that would resonate over time. And then had a director who also said, you know, yeah, actually, we know a lot of musicians who actually do really, really well in IT and with coding and things like that because they're kind of pre-programmed to do that. So I said, okay, well, this seems interesting. And so that's when I decided, okay, you know what? You're either in or you're out, so... let's go and just dove right into the coding.

SPEAKER_00: 6:45

Can you expand on that, the connection between music and programming or computer languages because it's fascinating.

SPEAKER_02: 6:52

So I think if you look at Music, and classical music in particular, which is what I've been trained in over the years, it's really just bits of code. So you have specific patterns that you follow, and based off of those patterns, you can, in music, evoke different feelings or different sentiments, or communicate things a little bit differently. Then moving that into actual coding and computer code, it's very much the same mental process. It's just what you're outputting, what sorry, what your output becomes is then just a little bit different. So I'm spitting out data now or rendering things to the page as opposed to trying to evoke feelings or any kind of sequence or tell a story.

SPEAKER_00: 7:37

And in classical music composition, there are some rules. There is sometimes some math involved as well, right? That helps us understand how the composer built something. the songs, right? So there's very

SPEAKER_02: 7:51

strict rules. Yeah, exactly. Very strict rules. And as you get further into or closer, like more modern music, it is actually based off of pure mathematics sometimes.

SPEAKER_00: 8:01

Yeah. Okay. So you had this project opportunity at work, which in my coaching practice, I call a novel project. So a novel project helps you use new skills in your nine to five job to deliver something of real business value. So that's the difference. A passion project that I do outside of work it's helping my skills development but a novel project that's well aligned at work sounds like a really great and exciting way to accelerate the bridge to your next big thing and it's one of the five pillars that I used so did you leverage any mentors or how did you approach this this project which would be fun and interesting but also a bit of a stretch

SPEAKER_02: 8:42

The project in and of itself was just a little bit of a taster initially. So it really helped me expand and understand how you would use IT within a business context, or in this case, within an HR context, and what went in and what were the elements behind that to make that work. And I think that really made me hungry to learn more. In terms of mentors, I think that really came later. And very much so as I was pivoting into the leadership realm, because that became so critical to have the sponsorship, but also have people who had been there before. Because coming out of the artistic world, to be really honest, I didn't know a whole lot about the business world. I didn't know what needed to happen, what you needed to avoid, what were some of the constraints. And so being able to have those people to guide me a little bit and continue to guide me, to be honest, and I think sort of the further and more mature you become in your career, the more critical these people become. I would say it's important to have more than one mentor. You don't want too many, but I have different mentors that I will go to for different things. So if I need something technical, I have a technical mentor. If I need somebody who's a little bit more people-oriented organizationally... I have my people mentor and then I have just a general business mentor who helps me understand kind of what the dials of the business might be.

SPEAKER_00: 10:13

Absolutely.

SPEAKER_02: 10:14

They're critical.

SPEAKER_00: 10:14

Yeah. And that, of course, takes years to build. So when you were coming out of this project, what reflections did you have after you delivered the project?

SPEAKER_02: 10:29

I think that's the biggest catalyst I had for signing up for the boot camp. Okay. At that point, the organization didn't want or didn't need somebody who had the coding skills. So they were like, yeah, it's not really for us to put you through this boot camp. It's not really mutually beneficial.

UNKNOWN: 10:51

Okay.

SPEAKER_02: 10:51

So I said, okay, well, in that case, I'll see you. Catch you on the other side. So I did leave that job pretty shortly thereafter, but immense gratitude for what it taught me and intrinsically also what it taught me about myself and what I like to do and really helped shape my future and continues to.

UNKNOWN: 11:16

Yeah.

SPEAKER_00: 11:16

where did you land in like a full-time role where that was more technical like was that after the coding boot camp and what were some of the pros and cons of the boot camp approach in in your view

SPEAKER_02: 11:28

i honestly didn't have much of an issue finding a job after the boot camp it was pretty quick three four weeks maybe started work as a specialist integrator helping a FinTech and then the external vendors integrate the product into their own systems. Benefits of a bootcamp is that you're just thrown into it and you sink or swim and you understand pretty quickly if it's something that you can keep up with or if it's something that maybe you need to move on. If you want to stay in the tech industry, there's still tons of different opportunities. So you don't have to be uber techie coder to be in the tech industry. It definitely taught me where I needed to stand with grit. Looking at personal reflection really made me dump the imposter syndrome to a certain extent because there was no time. You don't have time to sit and be like, oh, I don't know if I can do this. I think this guy's better than me. It's just like you have 24 hours to spit out that assignment and it has to get done or you're not going to pass on to the next level.

SPEAKER_00: 12:34

Yeah, that reminds me of an intensive language program I did for Chinese language where it was really the same because the pace of the weekly assignments, it doesn't matter what marks you got on today's daily assignment or whatever, because there's already going to be more tomorrow. So you really set the ego aside and you're with really talented people, of course, and some with more natural strength than others at that moment. So you just got to go for it, right? A

SPEAKER_02: 13:02

hundred percent. A hundred percent. It set me up very well also then for that leadership transition a little bit later. It's not a huge surprise to me to watch other colleagues from my cohort move into the leadership space as well.

SPEAKER_00: 13:16

Yeah. So let's talk about that. What motivated you once you were in to go beyond writing code and individual contributor roles? Because I've seen you speak on stage and the way that you speak about organizational leadership, organizational design, taxonomy, culture, it shows me that you've spent a lot of time not just learning about it, but also reflecting on it. Take us back to when you started to get motivated to do more than just what was on your personal IC plate.

SPEAKER_02: 13:48

I was working for a security department for a large bank. And as many IT organizations and security organizations tend to do, you have your engineers and your engineers speak one language and then you have your business and your business speaks a completely different language and never the two shall meet.

SPEAKER_01: 14:07

Oh man, guys, come on, please.

SPEAKER_02: 14:09

I need some help here. So I was sitting on the engineering side and they're saying one thing, but having worked on the business side and the business saying something else, I was like, no, that's not what they're saying. You have to, got to come to the middle a little bit. Yeah. So it, Where I started to transition towards leadership was very much as what I like to call a translator and being a translator between the tech and the business so that everybody could understand what was going on and being able to put that into play. And then that sort of naturally evolved to, okay, what people do I need specifically on my engineering team to deliver on what the business needs and to make sure that the business has you know, the speed and costing under control and especially if you're working in security, risk becomes a really big focal point. So all of these things come together and it all of a sudden becomes like this giant Rubik's cube that you have to get everything to align so that you can, you know, achieve your goals and achieve what you want to do and solve the problem in a way That is very holistic and really serves the purpose that it's meant for.

SPEAKER_00: 15:27

What you've done is you've built a bridge now into the CTO role. And you were most recently a field CTO at HashiCorp. What surprised you? And also, what did you find most satisfying?

SPEAKER_02: 15:42

So what did I find most satisfying? I love the advisory part of it. I love... Going in, sitting with other CTOs and acting sort of as a fractional CTO or I like to call it a shadow CTO. So sitting behind them to help guide them, ask the right questions about how do they want to pick apart their organization to make sure that they're achieving on what they need to deliver and really making that change and that incremental change that they need to achieve. What I found really surprising about field CTO in particular is depending on the organization, field CTO will either sit in or sit under the actual CTO. Sometimes it sits in sales. So the field CTO role I had sat in sales and that was a completely different world to me. I had... Absolutely no idea about how a sales organization was run or what went into it or what people were measured on or how they were measured. So all of that opened up this huge learning experience and huge learning world for me, which has really put a new perspective on things for me. So it's really informed me in terms of one more dial of the business that needs to be much clearer, but also, yeah, what is the greater scale of it?

SPEAKER_00: 17:15

I'm happy to hear that, Sarah, because obviously I'm a bit of a homer because I'm a sales professional myself. But more importantly, from what I read and understand, In order for CTOs to be highly effective and aligned with their CEO and CFO, having a read and understanding on the sales of the business can be crucial for that CTO to really own their space and be that real part of that leadership team. I've unfortunately seen company photos of C-level leadership teams and You can just see in the body language, it's the CEO, maybe the CFO over here. And then the CTO is almost at arm's length in the team photo. I'm like, goodness gracious. Like the message is ringing loud and clear. What is it that you find that you enjoy that you find satisfying about these kind of people topics? Why is that motivated you to continue?

SPEAKER_02: 18:12

You're going to have to be a little careful here because I can go down the rabbit hole really fast. What I love is that, and I think you see the the first inflection of this with Conway and Conway's law, who says that the lines of your business and how that's divided up and the complexity of that communication directly impacts how complex your technical systems are. Now, if you zoom out, what, 50, 60 years now, things have become infinitely more complex and they don't operate necessarily in that same kind of siloed manner where you would just, you know, kick the ball from Yeah. One to the other.

SPEAKER_00: 18:53

Right. Throw it over the fence. Say, this is your problem. You can't do it

SPEAKER_02: 19:09

anymore. What is the technical breakdown and what can I tweak and which dials can I move to have an impact on my top line or to have an impact on my bottom line? So I think the real job of a CTO is to understand, well, again, be a little bit of that translator between the technical and the business, but on a larger scale and on that more kind of macro scale. Part of that is also engineering the people, because I think we've seen over and over again, you know, Matthew Skelton was at that same conference where we Right, yeah. your team's gonna break down. So if I need a really highly trusted team because I need a lot of agility, I need to move really fast, I don't want more than seven or eight people in a team. Now, if I need a little bit more flexibility, I'm a little concerned about attrition, but I'm not quite as concerned about how quickly I get to market, 12 is okay. But anything outside of 12, you really start having a breakdown in communication and trust and you start seeing dividing factions. So all of these things, the neuroscience, the psychology, that really starts playing into how agile are your teams, how effective are your teams. that's gonna help you build more robust systems. So for example, if I'm hiring into a team, so I have somebody who's an Azure expert, and if I pull from my hashy days, somebody who's a Vault expert, what I'm going to do is try to avoid hiring anybody who's one of those two experts. Because naturally, if I do, build a high performing team and I do build a high trust team,

SPEAKER_01: 21:21

that's

SPEAKER_02: 21:23

naturally gonna spill over to the others. So what I wanna look to do is fill in the gaps about what do I need? What am I missing? Do I need somebody who's a little bit more business focused, who understands like the problem solving? Do I need a specific tool set? Do I need just a generalist? All these things then infer how I build my team and what the organizational structure then becomes and how it evolves over time. And I think we're moving into an era that's much more about socio-technical engineering than it is just pure technical engineering.

SPEAKER_00: 21:58

Yeah, I love this topic and we should definitely give folks a chance to hear more from you on this. I think that especially with AI changing the future of work, I know a lot of folks in our audience are interested in how organizations might look as machines are changing. increasingly involved or involved in different ways in decision loops, in relationships. And the point that you made about trust, I think, is worth emphasizing. So yeah, Gianni Giacomelli at the MIT Supermind group, he spoke about how trust is at an all-time low in general, in workplaces as well as elsewhere. So trust is at such a premium. So it seems more important than ever for leaders to design an architect with trust in mind how you described.

SPEAKER_02: 22:52

100%.

SPEAKER_00: 22:54

Yeah. So I'm going to take that as a brilliant segue to ask you, what has your career in tech, Sarah, given you in terms of your life design that matters to you? Because a lot of us who've reinvented our careers into tech, we made sacrifices to make it work, but we did it for reasons. And I'm curious what you've learned about yourself now that you have built a career in tech about your values, what it's enabled you to do, Tell me more about looking back.

SPEAKER_02: 23:29

This is a hefty question. I think one of the checkbox sort of exercises that I went through when I was pivoting careers was, would this make me... financially independent in my life and what it gave me the opportunity to kind of pass that on to my kids at any given point in time. Because it's really not something you have within the music world, the opera world at least. So that was a huge deciding factor for me to pivot. In terms of the growth and the continued growth, that becomes really... about my girls um because you know i have certain values that are really intrinsic to me um integrity massive on integrity trust is a huge part of my leadership style it's bilateral and then kindness and i think kindness becomes very conflated sometimes with being nice and they're fundamentally just not the same thing. You can be a very kind person, and if you have to deliver something, some really difficult news to somebody, for example, if I take one from my own career, letting somebody go, I hate doing that. It feels terrible, but it's not kind to keep somebody in a role or a place where they just can't succeed. It's better to say, hey, look, Let's figure out a way to get you into a place or company or something where you can succeed because it's just not happening. And it's,

SPEAKER_01: 25:07

you

SPEAKER_02: 25:07

know, it is the kindest thing to do, but it is very, very far from nice. Conversely, if I'm going to be nice to you, I could say, yeah, okay, keep doing what you're doing. It's awesome. And if that's not the truth, it's unbelievably unkind because So, you know, I do try to move very much towards that kindness. And it means uncomfortable conversation sometimes. But I truly believe that if I can't hold myself to those standards, I can't expect my girls to follow in my shoes. So what I do and how I approach leadership is very much the same way as how I would approach the rest of my life. And... be a role model, hopefully, for them as they grow.

SPEAKER_00: 25:59

How old are your girls now?

SPEAKER_02: 26:01

Oh, my girls now are 13 and almost 12. Oh,

SPEAKER_00: 26:06

brilliant. We're headed into the

SPEAKER_02: 26:07

challenging years. They're great fun,

SPEAKER_00: 26:12

though. Do they? Because I remember watching things that my mom or dad were highly proficient in when I grew up. And some of them made me scared, like playing the piano. My dad's a wonderful piano player and I never studied the piano. I played guitar and drums instead because I didn't want to mess with like, that's dad's like area of excellence, you know? So I'm curious with your girls, what type of hobbies are they getting into? And of course, 12, 13, then it starts to be like extracurriculars and stuff, of course. Are they playing at all with like robotics robotics, programming, or?

SPEAKER_02: 26:54

They don't know what I do.

SPEAKER_00: 26:56

Video game

SPEAKER_02: 26:58

making? Oh, okay. My eldest sat me down the other day. She's like, Mom, what do you do? I'm like, don't worry about it. It's fine.

SPEAKER_00: 27:07

She's like, I know you do something in tech. I'm

SPEAKER_02: 27:09

like, do you like going on holidays sometimes?

UNKNOWN: 27:12

No.

SPEAKER_02: 27:14

But funnily enough, you see them absorb certain things. So the oldest is very much... I would say my clone in terms of personality. And that is an interesting thing to watch unfold. Because you see all of the things and the traits that you were like, oh, I wish I had done this differently when I was 13. And then they do it. And you're like, oh, okay. I'm going to keep my mouth shut. It's your life. I know how this ends, but I'm going to keep my mouth shut. But no, so the... They're both quite musical. The oldest plays piano, youngest plays cello, and then big into sports. But one of their favorite pastimes is kind of to sit in a room and try to figure out how to hack everybody in

SPEAKER_00: 28:04

the room. Oh, yeah.

SPEAKER_02: 28:05

Oh, yeah. No, they love it. They're like, I would get into this system by doing this, this, this, and this. So it's things they've absorbed over time.

SPEAKER_00: 28:13

so they're getting the music side the music talent and the and a little bit of that uh engineering mindset too or exploring and playing stuff messing with systems like seeing what happens yeah experimentation yeah

SPEAKER_02: 28:28

then figuring out you know how does the system work where where's the weakness in the system what are the what can you like tweak to kind of figure out how that works um which i i love i think it's amazing yeah um But I think also at this point in time and the younger generation has it pretty hard because if I ask them, which I actually try to avoid asking them, what do you want to be when you grow up? Because I think we don't know what the future is going to look like. And I think especially, you know, like you were talking about in terms of AI, it's going to fundamentally change things. So what I hope to do with them and what I'm trying to do with them is instill that these are different skills that I need to have over time. But also very much the soft skills. How do I talk to people? Manners.

SPEAKER_00: 29:25

We use the term human skills, by the way, on the program. Perfect. I like that so much better. I have a veto on soft skills, by the way. Please. Thank

SPEAKER_02: 29:33

you. Human skills. Thank you for correcting me. So the human skills. And I think those are going to be much more important, especially moving forward, than any of the techie skills or the coding skills.

SPEAKER_00: 29:47

Yeah. Yeah, we're all just navigating right now. So thanks for sharing that. This brings me to the nonprofit that you mentioned. So New Tech Kids. Tell me about New Tech Kids and what their programming, what their mission means to you.

SPEAKER_02: 30:06

So Deborah Carter, who started New Tech Kids, is just, in my mind, an amazing human being. She... Yeah, I will let you do a little digging. There's a podcast I did with her, if you're interested in listening to her, which is on the HashiCast Women in Tech. I would highly recommend picking that up if you're interested in learning more about Debra. But she started this thing called New Tech Kids, and New Tech Kids goes into the schools. Initially, it was just for primary kids, and also initially just taught The coding side of things, but in a fun way where it was something that also, you know, the girls would be interested in and working with some of the more what we Americans would deem the inner city schools to make sure that that exposure was there as well. But what I love about what Deborah does is it's not just about the tech. It's about getting the kids to think about what are the implications moving forward of this tech. So, you know, I saw her post a couple weeks ago or a few months ago about AI and AI privacy. And so trying to get the kids at a really young age, probably about 10... 10 or so, to really understand what those implications are when it comes to AI privacy and what happens when you put your data into some of these systems and how does it, you know... impact the world and the greater world and so now she's moving that up into the higher schools so up into high school obviously that gets a little bit more complex so I just I love her cause I love her as a person so I'm super happy to give her a shout whenever I can

SPEAKER_00: 31:56

So we'll include a link to New Tech Kids. You can find them at newtechkids.com. And to hear and learn more about that, check out Sarah's podcast with Debra. We'll include some links here in the show notes. I think my takeaway from speaking with you, Sarah, is things can change, but developing and tapping into a sense of like, what's satisfying for me? What am I most curious about would lead me in a direction where I can work hard and build my next steps forward? Well, Sarah, thanks so much for what you shared about your journey, about breaking in and really developing your career in tech now to senior leadership and CTO positions. I think it's really inspiring because it took me time to make a new industry feel like home, even if it felt like a great fit, really getting established, building relationships and network. So thank you so much for being here. No, thank you. It's

SPEAKER_02: 32:51

been an absolute pleasure.