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Confido Q&A: How do you move from a Software Engineer to a Product Leader?




6 minute read

Are you a Software Engineer looking to make your next career move? Are you considering making that leap into a Leadership position? Or, are you already an experienced leader wanting to transition from a Corporate to a Startup, but unsure if it’s right for you??

Who better to ask than someone who has made these exact career moves with great success? 

Well, that’s what we did when we were lucky enough to sit down with James Fairhead, VP of Engineering, at Benefex, a rapidly growing Scaleup in the Employee Experience market.

With over a decade of hands-on experience, prior to his move into leadership, James brings a real-level of empathy to his team, and thought-leadership to Benefex, as he works closely alongside the CTO, Paul Smith, on the three products in development.

We found out exactly what James thinks it takes to be a leader & VP - from the skills, to the mindset - as well as discussing how a change in industry can be a beneficial career move. We also touch on the alternative career paths that engineers can take if they think leadership might not be for them!

Hi James, can we just start with a quick overview of your back story and path to VP of Engineering?

Well, back in 1999, I completed a 4 year degree in Business Information Technology, at Solent Uni, (Southampton institute back then). I chose to do this course, rather than Computer Science, as I was always interested with the business side of things.

So, 2 years out of Uni I moved to a Graduate Software Developer role at an Insurance company, called Transactor Global Solutions at the time. It was a great team, although small at the start - I stayed with that company for a total 13 years, through an acquisition in the last couple of years.

I started out as Grad developer and as the team grew there was a need for an Assistant Dev Manager role, then a Development Manager.

After that, I then went towards more of the operational and delivery side, progressing through to the Software Delivery manager, before moving onto Benefex and my current role as VP.

How did you know it was time to move on?

I think the reason I stayed that long, was the different roles available and the transition of the company. Due to the company’s growth there were always the opportunities, which was a bit of luck, it didn’t feel like 13 years!

The acquisition happened a year and a half before I left, I could see the company inevitably started to change with new owners and a new board. It wasn’t that that I didn’t get on with that, but it was a time of change which seeded the idea that it might be time for a change myself.

I guess the opportunity that came along (Benefex) too. Reading the brief and speaking to you guys, I thought that if I change, this might be a good time. Not that many people stick around for that long in one business in a career, and if I carried on, that might be it and other doors might start to close.

Also, I always knew if I was going to make a drastic change, it would be a different sector.

On paper the change sounds appealing, but how have you found that transition in practice?

It’s been good. One of the advantages I found, is that when you’re in a company for so long, doing different roles, you’re always relied on to do stuff, that might not be in your job remit anymore.

I’d moved to that hands-off role, into a leadership, but sometimes you feel like you’re dragged back in again to help out - even though it’s not your day to day. And you do it, because it’s normally a fire fight or something like that.

But, moving to a different company and not having that history of creating the technology, allows you to focus more on the role you’ve come to do. So I’ve enjoyed that and being able to rely on the engineers, rather than diving in myself and doing extra. That’s been a nice transition. And again, there’s always lots to learn when you make a change, whether it’s with the same company or a different one.

But, I’ve not looked back and it’s a great bunch of people here, so I’m building that again.

What are the biggest learning points, for someone else considering that move?

  • I think the biggest learn, is getting to know your team and people as quickly as possible and not being afraid to asks questions to find out exactly how things work.
  • Just be confident. It’s about building those relationships and overcoming some of those naturals fears that you might have meeting new people and a whole new team. Especially after that many years, you have to jump out of that comfort zone.
  • You go through onboarding phases in all companies. You might get assigned a mentor, so just utilising that, taking notes and trying not to ask the same question more than once and just trying to learn.


“You get quite a reasonable time to get your feet on the ground in most places. It’s not normally on the second day that you’re expected to do something. So, utilise that time as much as possible to learn - naturally, things will start to fall into place. It’ll be daunting to start with, but that’s like anything.”


  • Reach out across departments, as the key thing at any level, but especially as VP, for me is communication. Making sure that you can talk and entertain that conversation with someone, whether its good news or bad news – it’s important to build those bridges across departments.

Is making sure all departments are aligned a focus for you?

I think that there are multiple aspects for a VP, especially where I am, it’s quite a wide remit.

“People management, engineering, execution and delivery, leadership alongside the CTO. It really is splitting that role between yourself and the CTO, especially as the company grows.”

 The CTO can’t do everything, like people management and the Tech roadmap.

It’s also a role where you get the autonomy, to understand where you’re needed.

You don’t have too many strict parameters – you gauge the areas that need your attention. I cover 3 different products that the company is building. I wouldn’t say day to day, week to week, that I have a set time on each.

You’ve got to be a good time manager – knowing you come in the morning to sit down to crack on with planned work, but that something might come up and just manage that.

What are the main differences between management and being hands-on?

You take your average engineer and in an agile world, they’ve got a backlog to work through - they have meetings to plan that workload with sub-tasks. It can be as structured as you want. You can plug in, headphones on and focus on what you’ve got to do, with pretty minimal interruptions.

That’s another key thing about being a VP - allowing your team to do that.

You want to be able to take that pressure on yourself so that doesn’t filter down. You shouldn’t have people asking them specific questions, you’ve got to be their shield. You might expect more senior Engineers to be involved in meetings, outside of the immediate workload, but certainly not a junior to mid engineer.

It’s also about learning that transition, as a junior or mid, you’re going to have to want to be involved in that if you move up to senior.

Some people love the engineering and being a developer and being hands on.

Sometimes companies like to push people, especially when they’ve been there sometime or they’re well thought of by the management team - which is great - but they may not be that “people person”, and you almost see them fail at the role, which isn’t fair on them.

What would you advise someone that does enjoy being that hands on, or that might not be interested in management?

Well, I’d say, not to move into that sort management of role. There is a good career path in most companies to go through that full engineering route.

We talk about a T shape in a career path. The top of the T is the breadth - loads of different technologies you could learn. 

You could be really confident with the vertical line of the T - you could know everything about Java, but you could then look to expand the breadth of your skillset and learn Python etc.”

Also, with so many changing technologies, there’s lots to learn. 

There’s lots of contracting opportunities, you can earn good money as an excellent engineer. You don’t have to progress to a VP or CTO.

But for me, especially, I was happy to leave the hands on and move onto the management, while still having the understanding and passion for the tech, but not having to do it day to day.

Is there a key piece of advice for someone looking to make that step up to team / product leadership?

I think first of all, don’t try to impress. Just stick to the basics you know - most of the time you would have come across something similar. Especially if you’ve gone through some management training, led a team or led a scrum, you will have encountered it.

 “It’s not rocket science and most of it’s about doing the basics well. Know what your basics are, and don’t be afraid of asking questions.”

And importantly, self-learn. Tech moves so fast, and you might be going to a company with a tech stack that you’re not used to, so you’ve got to try and keep up-to-date as best you can, to work closely with the team.

Sometimes you have to beg for forgiveness if you make the wrong decision, sometimes you get it right. It’s just all about learning.

Apart from communication, people and management skills, are there any others?

I think from the people side, you’ve got to be good at setting OKRs and be quite articulate with that. You’ve got to get good and making sure people are ok and making sure they have everything they need and that they’re on track in their own career paths, and they feel like they can talk to you about any issues they may have.

To build on what I said earlier, it’s about adding that layer of protection for the team and being that face. I class it as being more of a coach than a leader.

And, it’s not about knowing everything. So people come to me, I might have to go away and find the answers, but it’s important to be that contact point. Again, it’s communication, for a lot of roles, not just for VPs. It’s about being there, being that face and knowing people so hopefully they can come to you for anything they need.

What are your day-to-day challenges?

Challenges and blockers will always happen, it’s software. Day to day you might walk in and something’s happened. But it’s how you walk in and handle that.

Not to repeat myself, but communication is a challenge across any company. There can be the view that engineering is over there and you might not always get those feedback loops.

 "It’s about educating departments, come and talk to us. It could be a five-minute fix for one of our engineers, and it could save you hours in the day. It’s overcoming that, which is quite a big challenge in a lot of places.”

 At Benefex specifically, right now it’s about improving our agile principles and getting consistent sprint quality and delivery on the products. On paper it looks quite simple - we’re sprinting and delivering every 2 weeks, but actually making that work can be quite a challenge.

What changes have you had to make moving to a scale-up?

It’s a lot of new processes and especially different department processes.

After 13 years in one business, you get to know how departments run, and when you change you have to learn that all again. You have to work out how the departments all work together and where engineering fits in and how that could be improved.

Defect management, for example, is a different process in most companies. Again, relatively simple, but how defects are triaged and fed to the engineering team to resolve involves a lot of processes between teams and it’s working out how to optimise that.

Also, getting to understand the team, how they tick, how they work, what their motivations are to work hard and get the job done. There’s social aspects of that too - there’s a change with who’ve you’ve gone out with on a Friday night!

What’s the main way that you learn and keep up-to-date?

Blog posts really. There’s lots of online material out there, you don’t need paid subscriptions. I just trying to keep up on stories on the tech news.

LinkedIn obviously is another good thing - keeping that community alive.

Medium, for me for technical posts – we’ve started one here, for the engineers to show what they’re working on. They’ll write some tech blogs which are quite interesting – you don’t need to know the ins and outs, but it’s about keeping in touch.

There are some good books out there too, especially for management. There’s the book, ‘Seat at the Table’ by Mark Schwartz, about how company’s have transformed to that product company for CIOs and CTOs.

What’s next for you?

I can’t believe it’s been 9 months already. I’m happy building this role out further. They’re continuing to grow and there’s a lot of scope working closely with the CTO and CEO. They’re vision of where they want to take the company is really good and everyone wants to get to there. So it’s just about learning within the position that I am, I haven’t thought about that, there’s scope to grow here.

We hope you’ve found the insights from James helpful if you’re considering a similar move!

If you’d like to know more about what it takes to be a VP of Engineering, or are just generally looking to make your next move in Tech, we’re here to help coach you and accelerate your journey to your next role.

Get in touch at contact@confidotalent.com to schedule a confidential chat with one of the team today, we’d love to hear from you.

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