Switching careers: Why I left Product Management to take up software engineering

What do you do if you hate your job? Maybe you’re getting bored. Maybe you’re burnt out. Maybe you’ve been so successful that you’ve outgrown your current role and are ready to move in a different direction. Whatever your reasoning, if you’re not enjoying your 9 to 5 it’s time to move on.

But when life deals you cards like this, it’s hard not to get overwhelmed. What if the next move isn’t the right choice? God forbid you’re out of the frying pan and into the fire.

We want you to know that changing careers doesn’t have to be stressful! That’s why we’re introducing our new “switching careers” series, in which we interview professionals in the tech world who’ve packed up their belongings in search of a different path.

For the first in our series, we sat down with JenniKate Wallace – a previous senior product manager who took a leap of faith and quit her job to take up her true passion: software engineering.

Jack: So I think the best way to start is an intro on yourself; obviously you started in Product – and if you don’t me saying – a little while ago.

JenniKate: I started doing Product before it was even a Product role and before anyone knew what Product was. I worked for a broadband company in Australia just on the phones – it was sort of like my first ‘proper’ job out of school – and we took payments over the phone every month. It was a massive influx of calls, and it used to annoy the hell out of me! I was complaining about it one day and the MD happened to walk past and he was like ‘well let’s fix that!’. I joined the tech team for a couple of months and we designed an online billing system for them. That kind of started it all, and even then I didn’t realise that’s what Product was. So then, I came over here [the UK] when I was 28 and got a job at Cable & Wireless because, well, I needed a job. That turned into a role where my job was essentially shutting down call-centres…

Jack: They must have loved you!

Jennikate:  Ha! The job itself was understanding their processes and then feeding back how we could automate the stuff. It was a very ‘Product thinking’ role. Then I joined Rated People – it wasn’t one I was particularly looking for, it just happened – and they’re very small, only about 11 people. They hired me as a Customer Experience person to work with the call-centres and again, similar sort of thing; dealing with loads of calls is really expensive. We hired a Product Director and they took me under their wing, and that’s when I had my first real Product Manager role.

Jack: What year was that?

JenniKate: That was about 10 years ago now. I was there for just under 5 years.

Jack: Was Product even a proper thing then?

Bryonny: Product was a thing, but it wasn’t a thing that every company had. I mean, you had like Website Managers and things, but Product only really became massive like 5ish years ago.

JenniKate: I think what happened was we started to have some real Thought Leaders in the field. People like Marty Cagan (HP, Netscape, eBay), who had been doing it his entire career was saying ‘hey, this is a *thing*, we can start putting some structure around this’. People like Teresa Torres (Capital One, Spotify) who’d come from a mixed background and working with engineers and the like were saying ‘hey, Product Managers, you need to get your engineers involved in this, here are some tools and techniques you can use to make this happen’. I think that’s kind of where the change happened to make it a more formalised Product role.

Jack: And then you moved over to Simply Business

JenniKate: It was just over five years ago… and I interviewed there – we had a connection between some people at Simply Business and Rated People. Their Marketing Director and now Product Director worked together in the past, and they got me in there. I actually left Rated People because I planned to move back to Australia, and then life happened! Simply Business got in touch and asked if I wanted to interview, and what I found at the time was that Product was sitting under Tech, and previously had been under Marketing – and they didn’t really know what to do with it. The CTO was very passionate about one of the Product practices, but the company had no idea how to implement it, how to make it work. They were trying to understand the difference between what a User Experience Manager would do, what a UI Designer, versus a Web Designer, versus a Product Manager…

Jack: I think people are still trying to work that out aren’t they?!

JenniKate: Yeah! So, when I joined, there was me and another Product Manager, and a Head of UX joined at the same time – he actually left after one project we did together…

Jack: …what did you do to him?!

JenniKate: Haha! When I joined the company, they talked as if Product was an established ‘thing’, then I discovered that it was actually about the company needing to understand the value of Product.

Jack: How many people were at Simply Business at that time?

JenniKate: Think it was about 60?

Jack: So huge for you?

JenniKate: Huge for me! But not big in the grand scheme of things. It was an interesting challenge to teach a company about Product, get them invested in what works and what doesn’t – and why things are good AND bad; nothing’s ever ‘just good’, but comparing the two. So I sort of look back on my five years and it really was a journey of the company going from no Product to a fully-fledged Product team now.

Jack: How many people were there in Product when you left [Q1 of 2019]?

JenniKate: Errrr, there were 9 or 10 teams already, and they were hiring for more. Product also encompassed the Product and UX Designers, so them as well. So huge in comparison!

Jack: Quite a crazy transition! So, I suppose, now you’ve made a different transition to engineering. When was the first time you tried coding?

JenniKate: Back when I was young, roughly 17 or 18, I had my old Apple computer writing some Visual Basic bits and pieces. There was this game – I can’t remember what it was called, but you could go through levels and solve problems, and then I found out you could build your own levels, and you had to code some HTML. It’s always been there in the background. I tend to get a little bit obsessed with ideas sometimes: watching the cricket in Australia I was getting a bit obsessed and wanted to prove the guy I liked was the best, so learnt how to use a spreadsheet to do statistics and stuff. Spreadsheets are actually great to lead into Programming because you learn a lot of the If/Then thinking. I failed maths at High School, so I couldn’t do Computer Science at university; at the time you had to have Maths, and to be a developer at the time you had to have Comp Sci. I didn’t really have any goals from a career perspective, and that’s how everything dribbled into place with Product, but I’d always dabbled with bits and pieces on the side. My Product portfolio used to be one that I’d built myself with CSS, HTML and JavaScript. It just wasn’t good enough to step out and do it for a job. There was a point in the early days of Simply Business where I did think I could career change into development; we had people coming in from Makers Academy…

Jack:  Oh because it’s a Ruby shop

JenniKate: Yeah exactly; but I’d always ask ‘can I do this’ and then just ‘nah, I’m too old’. So five years ago I was saying ‘I can’t career change now, I’m too old!’. At Rated People I was doing a bit of coding, and over time that became less and less – and at Simply Business I started to spend less and less time with the engineers and one day I thought ‘I’m not doing what I love anymore’. I always told myself that what I loved was Product, but what I actually loved was teaching people why it was important and helping people solve problems. It wasn’t the Powerpoint presentations and the communication, that’s just what I had to do to get to the other side.

Bryonny: And that’s why you took the step down from Head of to Senior, right? So you were more in the doing and closer to the devs, and the building cool stuff.

JenniKate: Back to building, yeah. I didn’t consciously realise this at the time, but I think what triggered it, was this woman from Simply Business when I joined, who was a Head of QA and Project Manager. Not deep into coding but always on the edge of it. She rejoined Simply Business as a Junior Ruby Engineer. I think in the back of my mind that was a trigger to go ‘you’re not too old!’. From there it was just a case of finding the best way for me to learn. I need clear challenges to go after, people to ask questions when I’m stuck, and so Bootcamp was a pretty obvious one. In recent years I’ve been really interested in React as well – so the General Assembly became an obvious choice.

Jack: How did you hear about the General Assembly?

JenniKate: So my partner did the GA nearly two years ago now. He’d come over from Estonia to do an internship in Product with us at Simply Business, and getting into junior Product is ridiculously hard. So he went to GA, came out, got a job, and is really happy. Well, I can trust the course, someone I know has done it.

Jack: Absolutely. Sorry for the pun here – but what gave you the coding bug? I know you were always interested in it, but what made you go ‘I want to do this more than I was doing at say, Rated People?’ What made you want to do just engineering as a career?

JenniKate: You get all the fun stuff, and the problem-solving side, and you get to build it. You can look at it afterwards and go ‘I made that’. I love making things efficient. Everyone at GA will tell you I was always adamant that if the code was too long we’d have to go back and refactor it and make it beautiful code. Obviously you can’t always do that… but it’s the thing about ‘I wrote those words on a screen and *this happened*’. It’s satisfying to know I did it, rather than talk about how it could be done. In Product it was always ‘we’ because I didn’t code anything or build anything, I just pushed people in various directions and made some decisions when people got stuck. Now I can look at some stuff and go ‘I did that’.

Jack: So how was the GA, overall?

JenniKate: It was amazing. A very intense course, which they prep you for at the beginning of the class. But you learn so much, so fast. I remember we were in our sixth week and we were starting back-end, and the class behind us started JavaScript at the end of their first week. And we thought ‘we didn’t get to JavaScript in a week did we?’. You look back and realise you learnt so much, and the way they’ve structured it is to teach you the really simple stuff first, and then start teaching you the JavaScript, and then how to think like a programmer, how to structure things. It doesn’t matter what language you’re writing in, there are still thinking patterns, elements you have to consider, the flows and the way data moves around. It was teaching us all of that while we learnt JavaScript and you just learn the other languages on top of that. For me, having these small challenges every day, where you could build what you were told to build, but you could go and do extra on top. Look at it and go ‘I could add this, and add that’, and Nick our instructor was always saying if we could do more, then he would hint at the sort of things we could add. It made it really easy to explore in our own time.

Jack: What advice would you give to anyone who was starting the GA tomorrow?

JenniKate: So if you’re starting tomorrow, plan your sleep time. It sounds crazy, and I thought it was crazy when I was told at the start – but it’s so easy to get caught up in the coding and the working and all of a sudden it’s 4 am. You can’t function without sleep! You need to be able to take in the information as it comes. Be very focused on taking a break, having some sleep, so you can learn everything the next day.

Jack: So – if it wasn’t programming or coding in particular, but felt stagnated in Product, what advice would you give them?

JenniKate: I think the main advice is to look at what elements of Product really still make you happy. It’s such a broad role and depending on the company you’re at, you may be doing all of it, you may be doing parts of it – just work out which parts make you really happy. If you really like setting up Agile teams, Product coaching is desperately needed out there. Obviously engineering is a fairly obvious one for a PM into the coding side of things. I know Product Managers that have left to be Marketing, or SEO, or Project Managers or completely different fields. There was one that moved into an Import/Export Buyer type role. She said it was something completely different, but because Product grounds you in communication, collaborative skills and what-not, she walked into that job and just had to learn the technical stuff. How do you interact with people, how do you get people to come on board and stuff?

Jack: Which is the hard part right?

JenniKate: I think that’s the strength that Product Managers have, which I assume comes naturally to them but I know it’s just years of experience of doing it. It does make you employable in almost any field.

Jack: Is there anything you regret – about going to the GA, moving away from Product…?

JenniKate: Not yet! I think if I’m honest with myself, I was ready to leave Product a couple of years ago, I just hadn’t figured out quite why I wasn’t as energised and loving every day as I used to. There may come things over time, but right now it’s been a good move for me.

Jack: It’s tough to make the jump right? I’d say it’s a courageous thing to do. When you think about the money as well.

Bryonny: I was going to ask about that. In terms of shifting careers, you’re used to being established in a particular industry. Years of experience, a really good salary that you’ve earnt. Obviously you’ll have to take a pay-cut. How did you manage that side of things?

JenniKate: Yeah it was having the savings, and living with someone that’s sharing the rent. I couldn’t have done it otherwise. I’d have had to do it part-time, still working, or something different than coding where I didn’t start all over ago. You know, I’m 42, that point in a lot of people’s careers where they start making the big money. I’ve been talking with Product people over the last 6 months and they’re like ‘hey, we’re looking for £100,000+’ and part of me goes ‘ah take the money Jen!’, but I know myself. If I’m not enjoying myself, and I won’t be motivated, I won’t do a good job – and that brings me down; I like to do a good job, I like to perform at a level that I set to myself. So, it was a bit of ‘okay, put the money aside’, it’ll be a significant pay-drop. Once I realised I could afford it, it became an easy choice.

Bryonny: What advice would you give someone who is a bit older? Not 21 and done a six months and said ‘that’s not my bag’, what advice, if anything, could you give someone to give them the confidence to make that jump?

JenniKate: I think the big thing is to work past the idea that you’re too old and people won’t take you seriously, and people will only want the up-and-coming. When I first started at the GA I was really conscious of the age of everybody – the average age is probably between 22 to 28. I think our class was half-and-half between career changers and people just starting out. I think you don’t compare yourself to them, because you bring a wealth of experience to the people that they don’t have yet. The youngsters coming out of university haven’t had to work a 9-to-5, deal with interpersonal relationships, work in teams – that sort of thing. The experience you can bring other than just coding skills are what can make you a good candidate really.

Jack: What’s the best advice you’ve been given overall – not just about the GA (or sleep)?

JenniKate: To make sure I bring out from my past all the experience that could be relatable.

Jack: Was that me that said that?!

JenniKate: It was you that said that! I’m a little bit lucky going from Product to Engineering that I have worked in the environment, so I can talk about Agile practices, I can talk about Sprints, deadlines, various technologies. Just because I’ve been exposed to them for so many years. Even if you don’t have that – look back at what does exist in your background that’s relevant to the path you want to take. There were ex-recruiters, ex-finance person. They were like ‘how does my background works’. We sat down for an afternoon and talked about it to figure it all out.

Bryonny: In terms of the tech side of things Jen, obviously the GA gave you good foundations, but were there particular elements of the course you loved? What you’d want to use on a day-to-day on a new role.?

JenniKate: I loved React. When we first started React from ES6, I thought ‘this is crazy, this is so much harder!’ but two days in I was like ‘oh React is awesome, everyone should use React!’.

Bryonny: What do you love about it?

JenniKate: It takes away a lot of the repetitive long code you have to write in JavaScript, you can just get stuff done. There’s a lot of condensing things, and it brings the front-end together with it. Not having to write a whole bunch of JavaScript, then a whole bunch of HTML – it links the two things together and they’re much more naturally connected. Which is awesome. Loads of people build libraries and plug-ins, so you don’t have to build the boring stuff over and over. If you need to do a log-in page which has been done hundreds of times, you can just get like, Material UI, plug it in, bang and it’s done. Then, the one I was surprised to really enjoy was the back-end side. I went into the course thinking I’d be a front-end developer and I love the front-end side, but when we started working on RESTful APIs, and I thought ‘this is cool’, then we did some Node, then Django and Python. I love it. It’s so structured and organised – and once you know the different places you need to put things when creating something, it’s so neat.

Jack: You should’ve been a designer!

JenniKate: I can’t design – I can draw blocks on a page but that’s as good as it gets. I think with the back-end for me, it’s really interesting – we only really scratch the surface at the GA, we do API creation, but we don’t really do get into the depths of back-end, but it’s just fascinating for me the way you store data and move things around. Then you get put a front-end on it without the heavy lifting on the front-end side. I find that really interesting.

Bryonny: In terms of what you’re looking for next. What type of companies, what skill-sets, what size of organisations. Give us some ideas of what would really interest you.

JenniKate: So I think my sort of dream set-up is a small company, start-up-ish, that is doing something for social good. I’m at that point in my career where it isn’t about the money, it’s about doing something I can feel really passionate about, so I can go home at the end of the day and feel like I’m really making a difference. The ideal would be a company that’s working to do that. I’m not industry precious, because there’s so many things out there that I don’t know about yet, but my personal passions are around health-care. I’ve had health problems in the past and seeing what the doctors, the receptionists, the nurses have to go through in terms of paperwork and organisation and then remembering everything, and then having to get in touch with people. It feels like that’s an area that could really use some help.

Jack: Is there any companies out there that we can shout-out on your behalf?

JenniKate: MyGP I’m really interested in. I saw there sign in Hammersmith and thought ‘ooh what’s that?’; I’m actually going to ask for the code so I can sign up because they connect through your practice. Trying to take away the pain of organising appointments.

Jack: Oh they’re like the messaging system for patients and doctors.

Bryonny: Yeah my GP use them too, they’re really great.

JenniKate: It was quite funny, I’d come across them after starting our final project which was a medicine reminder app. The other area I’m looking at a lot lately is Edu-tech. My mum was a teacher so I always grew up with books and games that were slightly educational focused. I know there’s a lot of companies out there that are starting to take the gaming aspect out there, so kids that are on a phone all day, are going to stimulate them. I think it’s Kahoot! that I saw at a design exhibition a while ago, and I was really fascinated by what they were doing. Although they were designed for children in mind, I was sitting in a room with adults playing their games and thinking ‘wow, I’ve actually learnt something today… and it was fun!’ – and I would totally have an app like that on my phone for the commute. There’s definitely stuff there that can help, not just kids, but for older people that do want to keep learning.

Bryonny: Stimulate your brain.

JenniKate: Yeah exactly! Not have to go out to school, because not everyone has time. Something you could do when you have spare time.

Jack: Have you found applying for roles since you left the GA?

JenniKate: The GA has set us up so well to do it. Astrid and Casey [Outcomes Team at the General Assembly] just haven’t nagged us to ‘fill out this thing, fill out that thing’ and ‘oh look you’ve got a CV’ and ‘oh your LinkedIn’s ready’, they’ve helped in how to structure the information and what to put in various places – and that’s been invaluable. I’ve not actually had to go out to anybody to apply yet – I’ve had some interviews already, and that’s just from having my details on a couple of platforms and sorting out my LinkedIn.

Bryonny: Are you doing any personal projects in your free time to differentiate yourself?

JenniKate: Like everybody, I’ve got my portfolio done, and added a few CSS bits – something I quite like doing. I’m working on a couple of things – once’s super early stage, not even coding stage yet. A friend is starting up a company to do with bees and helping people sell the honey. We’re in mapping out stage, processes, features, how to build them. I’m also working on Dungeons and Dragons site. It started off as just a calculator to look at random encounters, rather than going through pages and pages of books, it would get it all done for you. It sort of expanded out now, as a group I play in have built a new world to play in. We started building maps, new things about different cultures. The site has now morphed into somewhere we can store the information. Today I’m going to start building the models.

Jack: I think that’s everything we wanted to run through there. Thanks so much for your time Jen!

JenniKate: You’re more than welcome – good to see you both again!