Pioneer Profile: Meet Jennifer Dawson

21st Feb 2024

It’s time that we recognise the people behind the evolving world of work. Our working lives have shifted to being more inclusive, more people-centric, more flexible, and just plain better for both employees and companies. 

These changes didn’t just happen: they were put into place and upheld by individuals and teams working to create a better working future for everyone. 

So we’re finally putting the spotlight on the people who make great companies great: the people-people.  

People-people are crucial to the success of every company. They find you the talent that drives you forwards, and they’ve taken on an increasingly strategic role in the past few years – often taking on responsibility for mental health, diversity and inclusion, culture, EVPs, Employer Branding and team happiness. 

Read more about the Pioneers List and go behind the scenes to understand how and why we’ve selected our Pioneers.

We’re delighted to introduce you to Jennifer Dawson, Chief People Officer at StartOut, and one of our 2024 Pioneers. Read on to hear all about her career, her experiences with flexible working and building great company cultures, and her hopes for the future of work.

Tell us a little bit about your career history, and how you got to where you are now. What were the key milestones?

I spent the first few years of my career bouncing between operations, events (I used to work and live on a tour bus!) and hospitality. In 2009, I got my first job in HR at a small construction company and spent my first five years in generalist roles. I then joined an HR consulting firm and had the opportunity to work within companies of various industries, sizes, and stages. 

I then joined CAASE, a growing non-profit, as their first HR hire and built the people and culture function from scratch. After four years at CAASE, I decided to step back into consulting, this time on my own. I served as a fractional Head of People for a few startups and nonprofits and focused the rest of my time on strategic projects, developing expertise in equitable people operations. 

In 2023 I was presented with the opportunity to join StartOut as their first Chief People Officer and have spent the last year building up the people function and leading through organisational change. I also recently founded Equitable HR Guild, a collective working to share educational resources with HR professionals focused on equitable people operations.

When did you become interested in flexible working, EVPs, Employer Brand, and the future of work?

The traditional 9-5 has never been for me. I remember being 15 at my first job in a bagel shop and I asked if I could break up my hour lunch break into four 15 minute breaks because it worked better for my energy levels. I’ve also always been someone who questions norms and the status quo, and so I naturally have been curious about alternative approaches to work. Throughout my career, my commitment to flexible working and the future of work has grown stronger as I've come to realise how limited the traditional model is in accommodating the diverse needs of individuals. The old approach isn’t working and it’s time to build something better.

What is the most impactful change that you’ve implemented?

One of the most impactful initiatives I've led was a revision of benefits for a startup client that had recently completed a funding round and wanted to invest in a more inclusive and flexible work environment. We expanded their existing health benefits to better provide for families, LGBTQ+ individuals, and those with significant medical requirements. We revamped parental leave, transitioning from conventional maternity and paternity leave to a comprehensive parental leave policy that extends equal leave to all parents and includes support for adoption, surrogacy, and fostering. Additionally, we introduced new perks including a wellness program, professional development stipend, and a flex fund that could be used for expenses like student loans, fertility treatments, and gender transition costs. The existing employee satisfaction skyrocketed and they were able to increase the diversity of their team as they grew.

What’s the biggest impact flexible working has had on your own life?

I have always valued flexible work as a neurodivergent person with chronic illnesses. In 2023, when I encountered significant health setbacks related to my conditions, I needed time off to prioritise my well-being. I was able to transition to part-time hours at StartOut to concentrate on my health. Once things became manageable again, I transitioned back to full-time, but was able to maintain flexibility to accommodate doctor appointments and navigate through rough health days without undue stress. Flexible work was my lifeline as it not only supported my recovery journey but also allowed me to sustain my work which I love so much.

What’s the biggest challenge of being in your role/industry right now?

There has been an increase in recognition of the value that people and culture leaders bring to an organisation. While the newfound appreciation is great, it comes with additional expectations, dependence, and responsibilities. People leaders need to be extra strategic in how they prioritise and manage their expanding portfolios.

What do you think the next big trend is in working culture?

I’m not sure if this will be the next big trend, but one thing I would love to see is a more flexible definition of full-time and part-time roles. As the workforce is increasingly interested in fractional and independent work, I would love to see companies embrace that and offer options for their employees to dial down their hours to part-time to accommodate a side hustle or enabling individuals to adjust their hours week to week according to their availability. I would even love to see employers allow full-time employees to apply for additional projects or responsibilities and receive additional compensation, almost like picking up an extra shift or consulting on the side to bring in more income.

Take a look at the other Pioneers who made the list, and subscribe to our newsletter to get updates on new Pioneers, guides to help you navigate your strategic role, and exclusive invites to webinars and events