Name: Sara Stephens

Current position: CTO and Founder at Rest Less

Bio: I have a 14-year history in technology and recently co-founded Rest Less, a start-up whose mission is to help over-50s and inspire them to get more out of life.

I met Stuart, my co-founder, in June 2018 and was immediately inspired and connected to the Rest Less mission. Within two months, I’d left my role at an investment bank and joined Stuart as co-founder and CTO.

Prior to Rest Less, I worked in New York and London as an internal system product owner for Credit Suisse, where I built and led technical teams, and managed product delivery in the regulatory risk space. Alongside my career in technology, I am also an entrepreneur, having founded Southampton’s, Winchester’s and Manchester’s number one nightlife attraction on TripAdvisor, before exiting the business in 2019.

In my spare time, I to support women in technology and business through official and unofficial mentoring programs, making cocktails, and spending time with my rescue dogs, Laphroaig and Hibiki!

Hi Sara, thanks for chatting with CTO Craft today. Tell me about your life before leadership – what kind of roles and projects did you work on?

Before taking on leadership responsibilities, I worked as a junior web developer for B2C companies, where I was a member of teams that built, developed, and maintained web applications. I wanted to gain experience working in globally recognised financial institutions and so I joined a software consultancy that focused in this area.

During my time there, I worked on various projects in the financial sector, particularly in regulatory risk. I gained a lot of experience working in large international, cross-functional teams, building complex internal systems. Almost two-and-a-half years later, I took a leap and handed in my notice to travel the world for six months before starting my first leadership role at Credit Suisse!

How did your first leadership position come about, and was it intentional on your part?

I’ve always been someone who likes to take the lead and moving into those roles has definitely been intentional. When I’ve felt my leadership skills have needed developing, I have taken measured moves to do so. 

My first ‘real’ leadership role was when I took on the role of Team Lead of a development team at a client I had been working with. I’d been seconded as a consultant engineer within an IT department where I was known as an ‘agent for change’ and pushed for delivery, continual improvement, collaboration, and transparency between teams. This drive and attitude was recognised by the client and before leaving to travel, they offered me a permanent leadership role for when I returned.

How did you manage the transition? What came easily / what was difficult?

Looking back, I found the transition tough, although I’m not sure how much I realised it at the time. I had been out of the workplace for six months while travelling and was then immediately thrown into building a tech team of ten engineers for a year-long project.

I learned so many things in that role; when I first started answering this question I had a list as long as my arm, so I’ll try to condense it a little!

Things I found difficult:

  • Building a team of ten overnight is HARD, I made some great hires and some questionable ones;
  • Being the youngest in the team and an inexperienced women leader in a predominantly male industry is tough. There are many perceptions you have to overcome in order to be heard. Being a team leader by title means nothing if your team doesn’t buy into you; and
  • I had insufficient support from my manager. You wholeheartedly need this as a new leader and it is something that I am extremely conscious of providing to the leaders in my team.

Things that I found easier:

  • Having previously worked in the department in my consultancy role, I didn’t have the overhead of having to build new relationships and onboarding, which meant I was able to get up-to-speed very quickly; and
  • Managing relationships with external stakeholders. I enjoy building and maintaining relationships and this something that comes fairly naturally to me.

What was your biggest failure in that first leadership role?

I know we are supposed to embrace failure, but I’m not a huge fan of the word. I prefer ‘growth experience’ rather than defining something as a lack of success. In this role, there were two main growth areas. One was recognising when I wasn’t getting the support I needed, escalating it early and ASKING FOR HELP. I have reflected on this over the years and there are many intertwined themes. Being a young woman who was inexperienced in a leadership role, I felt like I needed to prove that I could step into this position all by myself. This resulted in me not asking for help. That mindset set me back, I should have accepted that asking for help is a way to grow and develop, especially since this was my first leadership role!

The second was managing expectations around roles and responsibilities. If you and your manager are not on the same page about this, it can lead to confusion on both sides.

What made you keep doing it?

I had and still do, have a strong support network around me. My various mentors and professional network continually gave me the confidence I needed to keep learning and developing.

After taking on more projects, the issues I had previously faced became less frequent. I also invested my personal time into building my leadership skills with my side-business, Bring & Mix. When it first became a success, it gave me more proof points that the leadership skills I was applying were effective and I should continue to develop them further.

Tell us a fun fact that nobody knows about you

I am a very open person, but I don’t think many people know that even though I don’t like heights, I bungee jumped twice from two different locations in New Zealand in the same day! The first was a 134m bungee suspended between two mountains, and the second was a backwards jump from 43m off a bridge into a river!

What are the three key skills you think every lead needs?Oh, this one’s a toughie, hard to reduce it down to three!

  • Listening – Not just hearing but *really* listening. Being an active listener is incredibly important;
  • Empathy – Particularly important during these trying times; and
  • Confidence – If you’re not confident in yourself or your decisions then you cannot expect your team to be.

What have you learned about acquiring and retaining talent?

I’ve learned a lot in this area over the past seven years and another question that could come with a whole host of points! Here are just some of the top points that I stand by, and I’m sure I’ll add even more to this over time.

On hiring:

  • Interview effectively – particularly for permanent hires. Make sure the candidate gets to talk with various different people in your team and that you define a solid process for testing the skills they’ll need for the job; and
  • Candidates should have a positive experience of your company from their first interaction. Manage their expectations, be clear about the process and provide feedback. 

On retention:

  • 1-2-1 meetings are paramount. Having regular check-ins gives you an opportunity to address any potential issues as soon as they arise; 
  • People’s motivations change over time and one size doesn’t fit all. Keep in-tune with your team members’ needs and adjust as much as possible to support them;
  • Always be open to the challenge of answering the ‘why’ question, and encourage people to challenge ideas and decisions;
  • Don’t push someone into a role they don’t really want. Play to their strengths;
  • Always be open and honest – teams are built on trust; and
  • Develop your people! If you have people who want to develop their skills, support them as much as you can. It’s an advantage to both of you.

How do you motivate your team and manage their stress levels?

This has been crucial during these current times. People have had a tendency to work longer hours because they are working remotely and stepping away from the laptop seems harder than ever. I encourage my team to take calls and meetings whilst walking so that they are stepping away and getting some fresh air. There’s also a budget provided to the team so they can purchase equipment that makes their workstations more comfortable. We have daily team coffee meetings that I don’t attend so that the team doesn’t feel like they need to talk about work! Across the company we encourage positive mental health practices and operate an open door policy – this is incredibly important to us.

How do you manage your own stress levels and productivity?

As the question suggests, these two are intertwined. Lowering my stress levels and increasing my energy definitely increases and maintains my productivity.

Since March, I have been getting back into running after a year of injury and it has been incredibly helpful in getting me to step away from my desk! I am also an advocate for therapy and coaching. I believe it is important to keep a healthy mind as well as a healthy body. Therapy and coaching is like going to the gym for the mind, it is preventative as well as curative.

My dogs are also a great way for me to unwind, whether it’s taking them out for a walk or having a quick play or cuddle, they are always successful in lowering stress levels – although constantly bringing a ball over to throw does take a slight hit on productivity!

How do you stay in sync with other parts of the business?

At 14 people, we aren’t a huge business (yet!), so it is fairly easy to stay in sync, although being completely remote can make it more difficult until you have the right processes in place.

We keep in sync through a series of daily huddles, formal and informal catch-ups, weekly ‘all-hands’ team meetings, and monthly town halls to review company progress. We also use Slack and have a whole host of channels that anyone can join to dip in and out of; it’s a fantastic way to keep up-to-date with the day to day goings-on. We’re a pretty collaborative bunch 🙂

Right now we are also looking at introducing ‘doughnut time’, where every week, two team members are randomly paired to have a 20-minute catch up on anything they like. I’ll let you know how it goes!

 Where do you see yourself in five years’ time?

I don’t tend to make specific plans that far out as too much changes! That said, my Big Hairy Audacious Goal is to continue to grow Rest Less into the number one digital space for the over 50s, globally.

And finally, which product do you wish you’d invented?

This is so clichéd but I’m going to say it anyway – a time machine! There are so many incredible advancements, inventions and connections that are to come, and I’m kind of sad that I’m going to miss out on a load of them!

Thank you so much, Sara!


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