Inspirational Woman: Jessica Heagren | CEO & Founder, That Works For Me

Jessica HeagrenJessica Heagren is CEO and Founder of flexible working site, That Works For Me.

Like many women, Jessica found that a senior career in a financial services corporate plus a young family just didn’t work and so she created That Works For Me in order to bring together skilled professional people in need of flexible work with businesses in need of skilled professionals on a less than full time basis.

Tell us a bit about yourself, background and your current role?

I’m Jess, I’m in my late 30’s, I’m a Mum of three young children and I’m CEO and cofounder of That Works For Me.

Six years ago, I was working as Strategy & Distribution Director in Direct Line Group having progressed quickly up the ladder from starting there while I was at uni. I had recently launched two new businesses and was responsible for 50% of the division’s income and 80% of the profits. On the Commercial Board, I managed some 600 people all over the UK. I ran talent programmes, I mentored young, upcoming women and latterly set up a group wide Diversity Board to deal with some of the more inherent issues in the industry such as the profile of business leadership not matching its employees. We identified a number of strands – Women, Family, LGBTQ, Race and Age – that needed to be addressed. We ran events, rallies and charity drives. I regularly presented to the Group Board on what needed to change.

I was leading the Women and Family strand when I had my first daughter.

I did a staggered return to work after 5 months on an agreed 4-day week. I was on calls at 7am until 7pm. I was driving at all hours of the day and I didn’t see my baby from Monday to Thursday. My precious Fridays were often spent on calls outside the baby sensory room. Over the next year my husband and my Mum brought my little girl up and when she was with me, she mostly watched Peppa Pig. It still sends her into a trance now.

When I fell pregnant with my second child, I’d had enough. I couldn’t maintain the pace so I left.

It still makes me sad to think about it now. At one point I was headed for the Board but because I couldn’t fit the standard 9 to 5 model I ended up leaving. After licking my wounds, and meeting more and more women like me, I was inspired to start That Works For Me.

A very brave and successful friend of mine called in tears one day on the brink of going bust because her under qualified finance resource has miscalculated her cash flow. I asked why she didn’t have a CFO and she said she was too small and didn’t have enough work for someone that senior.

“Why not recruit a Mum who’s done it before at a really senior level but only wants a few hours work each week?”

It was my lightbulb moment! I joined forces with my best friend and my sister and we built a platform that brings small to medium businesses the skills they need when they need them – on terms that work for both parties. Our thousands of skilled members are all people in need of flexible and remote work that fits around their life but they’re all experienced and all wonderful!

Did you ever sit down and plan your career?

Absolutely not! I ended up in insurance of all places – not many people plan a career in insurance!

I did have some life milestones though. I knew I wanted to achieve certain things by a certain age so I always had those in the back of my mind. I definitely stopped and took stock at certain times. For example, when I was offered a new opportunity in a different part of the company, or I started to feel bored. I was quite good at keeping that ‘what’s next’ conversation very open with my boss which I think is what led to my being promoted quite quickly at a young age.

I also knew that I wanted to run my own business one day. I had always done my Dad’s book keeping and had watched him go from someone who left the navy and taught himself how to fix a sink to building multi-million-pound houses.

Have you faced any challenges along the way?

Confidence has always been my biggest demon. That and what I now know to be imposter syndrome! I have always found that I go through an 18-month cycle when I do anything new. For the first 6 months I don’t enjoy it because I have no idea what I’m doing and feel stupid all the time, the next six months I grapple with the new skills and start to come out of my shell and then finally, for the next 6 months I enjoy it. After that I’m bored and want a new challenge!

Running my own business means I’m permanently in the first six months stage which I find really hard. Trying to get comfortable with not being good at everything and not knowing everything has been my biggest challenge of the last year. I’ve accepted that sometimes you need to call in the experts and that sometimes you’re just going to get things wrong! It’s about being able to take it on the chin, learn from it and move on. With a smile on your face!

What has been your biggest achievement to date?

Launching a business with three children under five. I don’t know whether the achievement is them or the business – both together has certainly been the biggest thing to navigate!

I’m also deeply proud of the women I mentored in Direct Line Group. Seeing their job updates on LinkedIn gives me a real feel good vibe and definitely puts a smile on my face.

What one thing do you believe has been a major factor in you achieving success?

I have had a couple of people – men – that have really believed in me throughout my career and they have given me chances that I wouldn’t otherwise have had. They saw something in me that even I didn’t at times. I like to think it was my ability to learn quickly and to adapt to my environment. I knew that I would have to fit in – fast – and I would have to figure it out on my own. Working in insurance there were so few female role models.

One of the things I love about the work I do now is how it’s so rich with inspirational women. Kathryn Tyler, Holly Tucker, Emma Jones, Lauren Currie…. for the first time in my life I have people that I can look up to and learn from. It really spurs me on to see women out there doing such amazing things.

How do you feel about mentoring? Have you mentored anyone or are you someone’s mentee?

Mentoring is critical! When you’re in an industry where there aren’t other people like you, as I was for many years, you need people who can give you what’s missing from your immediate environment. I had one or two mentors early on in my career that taught me a lot about how to carry myself in a room full of men 20+ years older than me and how to get people to believe in me quickly.

I like to think that I paid this back when I was more senior – I always had at least 3 or 4 mentees on the go! I’m a firm believer in giving back and would love to do that again now.

Now I have people who support me on an informal basis. Women who I have met since starting this journey – Lauren Currie and Kathryn Tyler are both amazing. I don’t have any formal arrangements in place as I’m only just figuring out what I need! That’s so important when talking about mentoring for it to work for both parties, I believe there needs to be a stated objective. For example, I would love a mentor now who is a female Tech entrepreneur who is a few years ahead of me on their journey. I must set aside the time to find someone!

If you could change one thing to accelerate the pace of change for Gender Equality, what would it be?

The gender pay gap is representative of all of the issues we face as women – lack of flexibility, lack of career progression, confidence – the list goes on. Companies should feel complete shame over inequality and pay gaps at any level of the organisation and it just should not be acceptable! We know what the issues are and how to fix them and yet businesses, often run by senior white men, do not give the necessary time and impetus to fixing them.

I have been astounded by so many male voices wanting to return to the status quo getting people back into the office as the threat of COVID-19 reduces. We know why! It’s because when all things are even, it will become very apparent that lots of women are as capable, if not more, then men and so many more will break through the glass ceiling. It suits them to hold us back and keep things as they are. This situation is an opportunity like no other and we need to grab it with both hands and make these changes permanent.

We can do lots more as women to support each other two. I love the idea that with every rise you put down a ladder to bring your female crew with you. I have found the entrepreneurial world to be so much more supportive of one another. The City has a lot to learn!

If you could give one piece of advice to your younger self what would it be?

Stop beating yourself up – you’re amazing. I still feel strangely uncomfortable saying “you’re amazing” to myself but I look back at the situations I navigated at such a young age and would genuinely like to pull young me to the side and say well done. I have always been so hard on myself and got so worked up for making mistakes or not knowing enough (this still plagues me now!) that I wish I had worked harder to find more people to be on my side. I felt very lonely at times and wish I had sought more people in the same position.

What is your next challenge and what are you hoping to achieve in the future?

My next challenge is making That Works For Me work. Making enough money to cover our costs and for Nic and I to take a salary ourselves is the next major milestone, particularly as Nic is about to have a baby. I love the thought of what we have built together being able to provide for her brand-new baby! I really believe that our business will keep more women in the workplace on their terms and will bring businesses the skills they deserve. We just need the world to know about us!


WeAreTheCity has a back catalogue of thousands of Inspirational Woman interviews, including Cherie Blair, Paula Radcliffe MBE, Caprice Bourret, Anna Williamson and many more. You can read about all our amazing women here

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