What I’d say to me back then – that dream job won’t fall in your lap, so speak up, says Workday’s Emma Chalwin

Madeline Bennett Profile picture for user Madeline Bennett March 15, 2024
The Workday CMO took a risk on relocating from the UK to the US, aided by her husband switching to stay-at-home dad

Emma Chalwin

While Emma Chalwin joined the tech sector by accident, marketing was always her first choice career. After studying European business studies with marketing - the first person in her family to go to university – Chalwin found work as a freelance stylist for a fashion magazine in London. 

Although she enjoyed the role, a friend working in tech sales suggested Chalwin have a chat about joining the firm, and she decided to go for it. That conversation 28 years ago led to a role as Marketing Manager at reseller Softcat, the first of many marketing positions at tech companies Chalwin has since held. She says:

I knew I wanted to be in marketing from the moment I was born. I was much more into the arts than science, I've always had a creative flare. I wanted to get messages to people, to engage with people. I'm a fanatic about brands, so it was a natural progression that I would end up in marketing.

Her five years in the reseller market gave Chalwin the opportunity to build good relationships with tech vendors across the UK and their marketing organizations.

Through those relationships, Chalwin has taken up many different marketing roles, including at McAfee, Macrovision, Adobe, and most recently Salesforce. Initially based out of London, in 2017, she got the opportunity to relocate to San Francisco with her husband, two kids and dog to head up Salesforce America's marketing team. Her role eventually broadened out to have a global remit, and last year she joined Workday as CMO. 


Over the years, Chalwin has learned to lean into her curiosity, and get much more comfortable with being uncomfortable, which opened up a lot of her leadership opportunities. She adds:

I also realized the importance of building a strong personal brand and that staying true to my core values and the things that really are important to me, were the foundations to build my success.

I remember my mom telling me at a very early age to treat people as I wish to be treated, and that's really served me well.

Another mantra that has stuck with her is from poet Maya Angelou. Chalwin explains:

The way you make people feel rather than the words that you say is really important. Your actions matching your words is a critical part of creating fellowship and being an effective leader. I've led with authenticity my entire life, and I'm a firm believer in vulnerability as a gift and a strength, not a weakness.

Chalwin also attributes her career progress to mapping out her soul work and superpowers, and building up a destination she wanted to get to. However, this wasn’t always easy in the reseller market:

It was definitely a boys’ club back in the day. When I say I mapped it out, it was more in the latter years of my career. If you had told me I was going to be a C-Suite executive when I was age 10, I would've fallen off my chair, especially leading a company like Workday. When I started out, there were no female role models that I could see that I wanted to be. I was very often the only woman at the table.

Chalwin found it tough at times to make her voice heard, especially as she wasn't a particularly gregarious personality:

I’m fairly introverted. It was hard, especially in my early twenties, to be taken seriously or felt like I was being taken seriously.

She recalls one particular incident very early on in her career at a distribution and reseller-sponsored conference on a cruise ship:

It was cocktail attire and I remember looking around and all I could see was dinner jackets and bow ties. It probably was one of the most vulnerable moments of my life where I felt really out of place. It was not fun. I was toying between, do I have to behave in a different way or can I be my authentic self? I'm proud of myself for sticking to being my authentic self.

Another memory that sticks in her mind is in a boardroom many years ago, when she was somewhat animated about showing her excitement about a certain program or getting her point of view across. 

I was told, 'Emma was pretty aggressive in that meeting'. Aggressive isn't a word that I don't think has ever been used to describe me. I thought, 'That's the most passionate I've been in a positive way about anything'. If a man had behaved in that way, they would've said, attaboy, he really cares about this. There's this nervousness of how we are perceived.


Based on these challenging experiences from her early days, Chalwin works hard to help empower the next generation of female leaders. People also need to see a reflection of themselves in the role that they want. She’s an advocate of women supporting women by showcasing vulnerability, that not everything needs to be perfect all the time:

A lot of the women I mentor feel they have to be the best wife, the best mom, the best sister, the best aunt, the best friend, the best leader, the best manager, the best colleague. You don't have to tick all the boxes.

Other than being a CMO, Chalwin’s most important role is being a mom to her two teenage boys. She views showing that you can still flourish in a career, while taking maternity leave and putting family first, as an important element of her role:

If I can share some of my experiences of when things went well, when things were tough, the good, bad, and the ugly, my hope is that more women can be inspired and see even a little something they can see in me that they one day want to be, that's really what motivates me.

When the family relocated to the US in 2017, it was Chalwin’s career that prompted the move. 

That was exhilarating and mildly petrifying all in one go. I had the first conversation and within eight weeks we were signed and found a place to rent. It happened pretty fast. The hardest thing was that I felt responsible for this working out.

It all turned out swimmingly - her children are thriving, thanks in part to the sacrifice her husband made not only to move, but to sell his business and stay home with the boys:

It's worked out amazingly well, but it certainly took its toll on me and my husband emotionally, because it was a risk. It was a tough decision, but it's one I don't regret for a second.

It was a tougher adjustment for him. The first question you’re asked is, 'What does your husband do?' I've never shied away from saying, 'He's helping raise our children'. Without his dedication to me and the kids, I wouldn't have flourished in my career here. It's not the traditional family situation, but it's the situation that's really been perfect for us as a family.

Plus, the stay-at-home dad is way more common in the Bay area than in the UK, Chalwin says. As they're taking on C-Suite positions, many more women there are realizing it makes sense, especially with a very young family, for one of you to be home. 


So what would 2024 Emma tell her younger self coming into the tech sector? 

The first thing would be buckle up, because change is the only constant, she argues:

If you can't move with the priorities of the business, then it's going to be tough for you. One of the best pieces of advice I was ever given was get comfortable with being uncomfortable.

Next, advocate for yourself and take control of your own career journey:

There are so many people that I speak to and mentor that are waiting for the right thing to just fall on their lap and someone to knock on their door and say, Hey, we are going to give you a pay rise and make you a people manager and move you here. 

I'm not sure I would've been asked to do that Americas job had I not been very vocal that at some point as a family we'd be open to taking on an international role or relocation. I was open, and back in the day, I wouldn't have had the confidence to even think about doing that. If we can encourage people to talk about what's their dream job, what are their aspirations. If you don't speak up, it's hard for people to read your mind.

Chalwin says it's reassuring to see the younger generation she mentors are starting to make huge amounts of headway in asking for pay rises and promotions, and their confidence is far greater than it was in her generation. 

Her third piece of advice would be, focus on work that fuels your soul, because you'll be far more productive and add way more value:

Develop a personal board of directors or trusted truth tellers that can help guide you. No matter what level you are, we all need mentors, sponsors, role models and advisors in our lives to keep us on track and be the truth tellers.

Lastly, she’d remind herself to understand the core values that are important to you and stay true to them as you navigate your career:

Find a company and a team that share these values, that's really when the magic starts to happen.

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