Inspirational Woman: Jen Taylor | Chief Product Officer, Cloudflare

Meet Jen Taylor, Chief Product Officer at Cloudflare

Jen Taylor is Cloudflare’s SVP, Chief Product Officer. She leads the delivery of world-class cloud-based security, performance, and reliability solutions for companies of all sizes.

Prior to Cloudflare, Jen was senior vice president of product management for Search at Salesforce and held other leading roles within the company. She’s also held

She holds a BA in Public Policy from Brown University and an MBA from Harvard Business School.

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

I’m Jen Taylor, Chief Production Officer (CPO) at Cloudflare. Fundamentally, Cloudflare makes things that are connected to the internet faster, more available, more secure, and more private. Our network spans more than 270 cities and operates within 50 milliseconds of 95% of the Internet-connected population globally.

As CPO, I lead the delivery of cloud-based solutions for organisations of all sizes, from non-profits to approximately 19 percent of the Fortune 100 using at least one Cloudflare product. I also work to prioritise inclusion and allyship within the entire company, and am the founding Executive Sponsor of Proudflare, Cloudflare’s LGBTQIA+ Employee Resource Group (ERG) that supports the LGBTQIA+ community within and outside of Cloudflare.

This time of the year is one close to my heart as a lesbian woman, with Pride in June and Cloudflare recently celebrating the 8th year anniversary for Cloudflare’s Project Galileo, which helps at-risk public interest groups stay online by providing free, robust security. The Internet is a powerful tool for spreading and expanding ideas. When journalists, social activists, and minority groups are flooded with malicious traffic in an attempt to knock them offline, the Internet stops fulfilling its promise.

Project Galileo supports numerous brands, including organisations that support the LGBTQIA+ community in the UK. By protecting them from cyberattacks and keeping their websites and helplines online, we help them to continue their essential work. One such company that is protected by this project is Switchboard, which is one of the UK’s oldest LGBTQ+ helplines – the company provides a judgement-free space for people who need support.

Did you ever sit down and plan your career? 

My career was not planned. I did an environmental policy undergraduate degree and thought I would go to law school, but thankfully, some of my friends went first and told me that it was dull (no offence to any lawyers out there!).

Instead, I went into IT consultancy because I love tech and love solving problems. I’m the kind of person that plugs in a piece of hardware like a set-top box and just goes for it – I don’t look at the manual to understand how things work, I just go.

After that, I ended up in investment banking and while I loved the strategy side, it made me realise that I wanted to be in the delivery side again and I missed the execution part of my previous job. At this point, I went to business school to catch my breath and realised product management would be a good fit for the things I enjoy doing.

Making career decisions is hard and can be confusing and disorientating at times. What I’ve realised is that your career journey is often created from learning from mistakes. I’ve learnt that the hardest thing for me was to listen to myself, find what really makes me happy and what it was I was running from. You need to look for the signals of running from something and reflect, because these things will follow you if you ignore them.

Have you faced any career challenges along the way and how did you overcome these?

A big career challenge for me for me was being a lesbian. I am fortunate to have built myself a career over the past 25 years, but feeling I could truly be myself at work was a challenge. Learning to accept myself for who I am and helping to celebrate diversity in the workplace has encouraged me to be myself. It brings me joy that there is a shift, and the new generation of workers don’t have to go through the same thing I did, as society is becoming more accepting and increasingly celebrates individuality.

What has been your biggest career achievement to date?

I’d say my biggest achievement to date has to be working with my current team. I’m so honoured to work with the people on my team – they are smart, curious, and diverse individuals that I’m continually learning from.

With the growth of the team comes personal growth for me as a leader. I’m very proud of how both my team and I have progressed and where we are today. By helping to push each other and facing new challenges together, we unlock new opportunities.

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

For me, mentorship has been hugely beneficial. Having people take an interest in me and my ambitions and providing me with feedback is incredibly valuable – even when it’s an opinion that I didn’t want but needed to hear!

More specifically, having people act as an advocate for me when I move roles and organisations has really supported my development. When it comes to your career, there is no guidebook or set of rules, so mentors can add crucial wisdom for your career journey.

What top tips would you give to an individual who is trying to excel in their career in technology? 

I would give them the advice that I wish I’d had at the beginning of my career, which is to be yourself. It’s exhausting spending time hiding yourself and separating who you are as a person from your professional identity. I think for me, this impacted my ability to be in the flow of the conversation and openly collaborate with other people.

The advice I got from one of my mentors was to be completely yourself, to bring your whole self to your work and to your organisation. Being yourself is enough – and it’s powerful. If an organisation doesn’t want to accept and celebrate who you are as an individual, it’s not an organisation that wants or deserves you to be part of it.

Do you believe there are still barriers for success for women working in tech, if so, how can these barriers be overcome?

I see three main barriers that women in tech face and need to overcome in order to succeed. The first barrier is one that is created for us when we are young – the narratives we hear in our youth and internalise about the expectations of us as women.

The second is our assumptions of leadership. We need to change the way we presume what makes a leader. Just as many women deserve the freedom of choice in our careers (for example, the choice to be mothers as well as business leaders), we need to support a culture where it’s fine for men to have the same flexibility for their choices, for example to be a stay-at-home father.

By breaking down these expectations, we can help overcome barriers for stereotypical working roles and enable everyone freedom of choice and career growth, alongside personal life experiences.

A final barrier that’s linked to my previous point is being closed off to looking at less traditional career paths as a route into leadership. This is true for both men and women.

To break free from this, it’s vital to understand how we create paths that are open to workers coming back and picking up where they left off.

What exactly is the best way to overcome these barriers?

When it comes to overcoming these barriers. It’s vital to continue to have conversations about them and bring them to the surface. My advice would be to build workplace communities that are inclusive, accepting and continue to challenge societal norms.

What do you think companies can do to support to progress the careers of women working in technology?

Professional development is so important, as is having people providing honest feedback and championing your success. I’m a big believer in having strong advocates and a diverse range of mentors to support your career. While this is something that the individual can set in motion themselves, it’s equally important that companies instigate, encourage and support this approach.

In terms of top tips for finding a mentor, when selecting a person for this role, try to find somebody who’s a little outside of your comfort zone. I have personally found that what I often need from mentorship is to get out of my own way and have somebody bring a different perspective to how I’m thinking about and approaching things.

Another piece of advice is that when you ask for a mentor and eventually meet with them, be sure to bring the agenda – as the mentee, you are taking time from this person, so help them to help you.

As well as supporting mentorship in the workplace to help female employees develop, employers need to step up and implement policies to tackle inequality – we still need to overcome traditional social and cultural norms that require women to take a primary responsibility at home.

While compromise is an unavoidable part of life, both in our personal and professional endeavours, I believe that success is about choice. We all need to allow ourselves the freedom to set a goal and have a dream.

There are currently only 21 per cent of women working in tech, if you could wave a magic wand, what is the one thing you would do to accelerate the pace of change for women in the industry?

Continuing to push the boundaries of how roles and leadership are thought about is key to accelerating positive change within the tech sector. As an industry, tech is constantly pushing boundaries – whether it’s better processors, more efficient ways of keeping hackers out or beating the speed of light.

We therefore can – and should – be just as relentless when it comes to pushing boundaries around the role of women in tech, whether that’s allowing more space at the table or demanding and appreciating more diversity and inclusion within those teams.

What resources do you recommend for women working in tech?

I believe two of the greatest resources for women working in tech are learning from mentors and networking within your community. As previously mentioned, mentorship really helped me in my career journey, and getting to know your peers from across the same sector can help give you strength and empowerment.

The culture within tech communities really does have different norms. You’d be surprised how getting to know your community can help support you – not just in your career but also in your personal life.