When Jessica Pillow launched her firm, Pillow May, back in 2011, her goal wasn’t just to build a successful practice. She wanted to prove that it was possible to run a great business and have a life – especially as a working mum.

Fast forward to today, and Pillow May has grown into a thriving firm of 10 people with over £400k in turnover. It’s built on strong systems, a close-knit team, and a work-life balanced culture that puts people first.

In her growth story, you’ll learn how Jessica:

• Balanced starting a business with two maternity leaves (and later, cancer treatment)

• The practical steps she took to grow Pillow May in a sustainable way

• Why she’s always prioritised flexible working – without compromising on service or quality

• The role her team, her systems, and her mindset played in building a business that works

If you’d like to listen to or watch the conversation, click below for the YouTube video of Jessica’s chat with Heather. 

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About Jessica

Jessica set up Pillow May in 2011 after returning from maternity leave and being told she wasn’t doing enough at work. This was despite balancing the demands of being a new mum and giving her all, so it was a clear wake-up call. She knew she couldn’t give more (especially in a partnership where work-life balance was already impossible!) and realised she didn’t want to be part of a culture that asked her to.

So, she left. And she started her own practice.

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Starting the business

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The decision to launch Pillow May wasn’t just about setting up another accountancy practice; Jessica wanted to prove that a flexible working environment, especially for mums, was achievable in the industry. Why? Because she wanted to build a business that supported the lifestyle that she wanted. One that would allow her to be present for her children, support other working parents, and deliver high-quality service on her own terms.

She started small, with just five or six clients – mostly people she’d worked with before – and she built the rest from scratch. However, one thing was clear from day one: this firm was going to grow, and it was going to grow in a way that worked for her and her family.

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Overcoming early obstacles

The early years of Pillow May were carefully paced as, like many new businesses, a balancing act was necessary. Jessica welcomed her second child not long after launching the business, and she consciously decided to keep growth manageable while preparing for maternity leave.

It wasn’t until after her son was born and she knew maternity leave was behind her that she really began to push forward. By then, she had more clarity, more capacity – and the drive to take things up a gear.

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Committing to growth (without burning out)

Jessica knew that if Pillow May was going to grow, it had to be sustainable. That meant putting the right foundations in place. As a member of the Accountants´Growth Club, Jessica worked with her Growth Specialist, Heather Townsend, and focused on the following key areas:

1. Getting the systems in place

With growth in mind, Jessica knew early on that robust systems were essential, so she worked closely with her business coach to systemise as much of the practice as possible. Every process was mapped out so the business could run smoothly – even when she wasn’t around – and this was crucial not just for growth and maintaining high service standards but for peace of mind.

2. Raising her prices

In 2016, Jessica increased her fees by 30%. It was a bold move, but a necessary one. The higher fees meant she could hire more support, build a stronger team, and continue growing without overstretching herself or the business. This was particularly vital in later years when she had to take time off for her cancer treatment.

3. Hiring the right people

Jessica knew she couldn’t (and didn’t want to) do it all alone, so another focus was to build a team that shared her values and cared about clients as much as she did. Early on, she knew the success of Pillow May would rely on more than just her, so she invested in hiring the right people and developing a collaborative culture (one that has actually been key to the business’s success).

4. Managing growth (without sacrificing team-wellbeing)

Rather than saying yes to every potential client, Jessica focused on bringing in the right ones. Why? Because she wanted their growth to be steady and intentional, and never at the expense of her team’s wellbeing. For her, overvoiding overwhelm was important as her main goal was to build a sustainable business that provided a positive and flexible work-life balance for everyone.

5. Using personality profiling to build a stronger team

As the team grew, Jessica introduced personality profiling to help her understand how people worked best and what their strengths were. This tool not only improved communication and collaboration within the team, but it also meant fewer hiring mismatches in the future.

A recent training day where everyone shared their profiles and learnt about the different working styles has really brought the team closer together and strengthened their dynamics – and this approach has become key to Pillow May’s ongoing supportive culture.

6. Maintaining flexibility and control

Flexibility has always been a core value at Pillow May, particularly as Jessica is a working mother, but it’s backed by clear boundaries. For example, Jessica’s team works within defined hours, so there’s structure and consistency, both for the team and for clients. This allows the business to continue delivering a high quality of service while still maintaining a healthy work-life balance.

7. Always thinking ahead

Even in the thick of it, Jessica always had one eye on the future. Therefore, every decision has been made with long-term growth in mind. Whether it was refining systems, developing her team, or planning for an upcoming acquisition, she’s always been focused on building a business that lasts.

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Getting through the toughest year

Every business owner faces challenges, but for Jessica, 2016 brought personal and professional trials like no other. Diagnosed with breast cancer, she suddenly found herself balancing treatment, surgeries, and a long recovery with the need to keep Pillow May running. So how did she do it?

While it was a daunting period, thanks to the systems she’d put in place and her resilience and forward planning, the firm didn’t just survive – it kept growing.

Systemising the business for survival

The processes Jessica had worked hard to put in place meant the business could run smoothly without her daily involvement. This proved invaluable when she had to step back for treatment and recovery. 

Delegating and stepping back

Jessica’s ability to delegate and trust her team became the bedrock of Pillow May’s success during this challenging period. Not only that, but she also hired a PA to take on day-to-day tasks and keep things moving. From managing her diary to chasing up clients, her PA helped take the pressure off so Jessica could focus on her health and still keep an eye on the bigger picture.

The team pulled together

It wasn’t just the systems that kept the business going; it was her team.  Jessica had always believed in building a supportive and collaborative culture at Pillow May, and this period was when that ethos really proved its worth. Her team rallied around her, stepped up to take on more responsibilities and handled more than ever before and the result? They kept the business running smoothly.

Planning paid off

Through chemotherapy, surgeries, and the ups and downs of recovery, Jessica found strength in her team and the systems she had created. After all, the systems, the team, and the mindset she’d built all came together when she needed them most. It wasn’t easy, but Jessica came through that period with a business that was not just intact but stronger.

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The future: lessons learned and what’s next

Looking back, Jessica reflects on the importance of both her team and the systems she’s put in place to sustain Pillow May’s success. Her close-knit team’s support kept the business running smoothly during her illness, and they didn’t just keep it afloat; they continued to drive growth. This experience has only reinforced her belief in the power of structured processes and effective delegation.

As she looks to the future, Jessica has big plans for Pillow May. With an acquisition on the horizon, she’s preparing to double the size of the business, aiming to push turnover towards the million-pound mark. However, despite these ambitious goals, her focus remains on:

• Maintaining the high standards and flexibility that have become the hallmarks of the firm.
• Continuing to evolve her systems, ensuring the business is equipped to handle its growing client base.
• Staying true to the core values that have guided it from the start.

When reflecting on her journey, Jessica is clear: while systems and processes are essential, it’s the people who are the heart of the business. Her experience has taught her that growth doesn’t always mean pushing forward at full speed. Sometimes, it’s about taking a step back, pausing to ensure that everything is running smoothly before making the next big move.

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** Pillow May is a thriving, values-led accountancy firm that champions flexible working and sustainable growth. Want to learn more about Jessica’s story or connect with her directly? You can get in touch here.