Career Q&A with Heather Hatlo Porter, Chief Communications Officer at Chegg (#13)

The next Career Q&A is with Heather Hatlo Porter. Heather offers exceptional advice on how mentors can help us get unstuck, how failure can be a career accelerator, and how to find the courage to seize opportunities that may initially intimidate us.

Heather is Chegg’s Chief Communications Officer, leading all internal and external communications efforts for the company. Previously, as VP of Marketing, she was responsible for building Chegg’s brand narrative, creating innovative campaigns with major influencers, and spearheading cause-marketing efforts. Her passion for the mission inspired her to help launch the Chegg Foundation in 2013, later transitioning it in 2019 to Chegg.org, the new social impact, grant-giving and advocacy arm of the company that elevates the student voice through policy efforts such as the “Unlocking The American Dream” student debt policy report.

When she is not focused on putting students first at Chegg, Heather is focused on her own students, her two sons, and can be found cheering at the ice rink for her kids as a devoted hockey mom or volunteering with local organizations as a passionate community member.

Was there an experience you had before age 21 that shaped who you are? What was it?

My very first job, in high school, was a courtesy clerk for Nob Hill Foods. And, it wasn’t so much the work or the role that had a profound impact on me, but it was the lessons I learned from the leadership team there.

Back then, I was going through some challenging times in my personal life, and I will never forget how caring and supportive the management team was. On the days when I couldn’t make it to work, because of one reason or another, or on the days I showed up late, they met me with such compassion and understanding.

When so many employers would have seen a flighty 17-year-old girl who wasn’t fulfilling her obligations to the job – which certainly should have led to getting fired – they took the time to ask what was going on and inquire as to why my schedule seemed so unpredictable. They got to know me and, through that, were able to show a level of compassion I never expected from “the big bosses”. In fact, during a particularly rough spot in my life, one of them even offered to let me stay with their family temporarily. Thankfully, that wasn’t necessary but just the thought that someone who I worked for would do that for me had a deep impact on how I think about my own employees today.

I have learned to really prioritize getting to know what is going on in people’s lives outside of the four (virtual) walls at Chegg. By understanding where they are coming from, what they are experiencing, what challenges they might be facing, I can do a better job of supporting them in their work. Quite frankly, I treat them like they are family because I think that’s the best way to bring out the best in people. I always start team meetings by asking how they and their families are doing so I know how to support them in any way they may need.

Giving your employees grace, encouragement, and understanding creates a culture where they know they can trust you to lead them to grow and succeed. When a person feels cared for and supported, they are much more likely to be fully invested in their work and deliver superior work at that.

How has a failure, or apparent failure, set you up for later success? Do you have a “favorite failure” of yours?

I have failed many times; I am not sure where to start! Some of the marketing campaigns that I thought would be phenomenal over the years ended up falling flat. I learned afterwards that these campaigns failed not because the idea and execution were lacking, but because the audience’s appetite for it simply wasn’t there. The biggest takeaway from all these failed campaigns is to always research before executing an idea and to find out what the audience actually wants. Assumptions are great, but data is better.

At Chegg, we have an entire research team dedicated to surveying students’ needs and wants, and we deep dive into the survey results to create products and services that benefit them the most. Along those same lines, I really value our interns’ feedback every summer because they are much closer to our target demographic than I am, and some of my ideas have been shot down by them for being irrelevant or outdated (and let me tell you, sometimes that makes me feel so old!). What this has really ingrained in me as I have progressed throughout my career is to do my homework, identify what it is I am trying to accomplish, understand if it is big enough to matter, and then make sure I know how we would define success for whatever it is we are working on.

What advice would you give to a smart, driven college student about to enter the “real world”? What advice should they ignore?

My advice for students is to go easy on yourself. Like most other college students, I used to experience a lot of self-doubt and anxiety about my future. I felt rushed to land the perfect job and enter a relationship, putting way too much pressure on myself about every decision I made in my early twenties.

Looking back now, I realize that my career path looked nothing like I expected but, each step along the way, I learned invaluable lessons and I honestly wouldn’t change a thing. I know many young people, especially at this time, are feeling very uncertain about their future amid a global pandemic and economic uncertainty. I think now, more than ever, it is particularly important to take time to invest in your mental health and well-being and give yourself permission to not have all the answers, to not know what comes next, and to be okay with that.

So, I guess on that note, the advice I would say to ignore is the old mantra of “fake it till you make it.” Don’t fake anything. Be authentically you, don’t stress too much about the future, and know that life is a journey and some of my best moments came out of the times where I had no idea what was going to happen next. 

What’s something unexpected that has happened in your career, and how have you responded?

I have been given several unexpected opportunities throughout my career, opportunities that I did not have the skill set nor the experience for at the time. But I had the courage to seize those opportunities, and ultimately, I used these experiences to build up my confidence.

I knew I was great at being an executive assistant, so I was hesitant at first when the opportunity to join the marketing department came up. I knew I wanted a change, but I didn’t know if I would be successful at it. So much so that I told my boss at the time, “let’s just try this for six months” fully expecting her to fire me at the end of that test. 7 years later, under her mentorship, I was the VP of Marketing. I could never have predicted that but because I took a chance on something that scared me, it opened even more doors which, eventually, put me on the path to becoming Chegg’s first CCO.

I think being able to articulate what it is I want to do and, equally as important, knowing what I don’t want to do, being willing to take risks, and embracing failure has really helped me excel through my very non-traditional career path.

Since entering the workforce, how have you changed or transformed?

Well, I started working full-time at 18 so I have grown tremendously over the course of my career in so many ways. I think one of the more obvious places of growth is that I had to learn how to accept not being good at things, at failing, and being transparent about that. Early on in my career, I thought that failure was not an option and that it would be catastrophic for me professionally. Now, my attitude towards failing is the exact opposite. I learned that failure can be a career accelerator because of the learning opportunities you get every time something doesn’t work.

In fact, Esther Lem, Chegg’s CMO and one of my mentors, really modeled that for me by celebrating failure every month in our marketing team meetings. She gave failure a central point in our team meetings, allowing people the opportunity to talk about the lessons they learned and so that others could see the failures across the team. These meetings taught us to take ownership of our failures and to be empowered, rather than hindered, by them. 

When have you felt stuck in your career? How did you break out of it or push forward?

I was an executive assistant for ten years. By the age of 30, I had reached the top of the career ladder for that role, having already worked for the CEO and Chairman of the company. I didn’t know what I wanted to do next and felt stuck in terms of professional growth. I actually tried to resign from Chegg because I thought there was nothing more for me.

Fortunately, another one of my amazing mentors, Dan Rosensweig, encouraged me to explore my other interests, such as philanthropy and creative storytelling, and recommended I give marketing a shot because it seemed like a fitting pivot in my career. It was like a lightbulb went off because I had never connected my degree, which was focused much more on creative storytelling for film or theater, to brand storytelling. He was able to offer me a perspective I wouldn’t have even considered on my own.

So, when you feel fatigued or lost or just that you have reached a plateau in your career, I think the first step is just being self-aware. I knew when I was at the end of one path. I just needed some guidance about finding my next one.

And, on that note, I think surrounding yourself with great mentors is really important because they can challenge you in ways that might surprise you. And then, when the opportunity to make a change presents itself, you have to be bold enough to take the risk at trying something new. When that door opens, ignore that self-doubt and just go for it.

Who is one person, dead or alive, who you admire? Why do you admire them? 

I feel like, on any given week, I would have a different answer to this question because I admire so many people for so many different reasons. I look up to the many amazing female mentors I have in my life, like Esther Lem, Lee Woodruff, Desiree Gruber, and Melanie Whelan. Right now, I am really in awe of Arlan Hamilton, because she is transforming the venture capital world.

I started my professional career in the corporate legal environment and then moved into private equity. But, unlike my peers at the time, I did not have a master’s degree from an Ivy League school. In fact, I attended community college, transferred to a local state school, and did not pursue a higher degree afterwards and, because of that, for a long time I felt like I was always underestimated. It weighed on me a lot but also made me work much harder than everyone else around me. I always felt I had to hustle to prove my worth.

Arlan seems to have a similar mentality. She experienced so many setbacks but has still shown the world that it doesn’t matter where you came from or what your background is. What matters is where you are going and your ambition to get there. I admire how she hasn’t let anything hinder her success and how she stays focused doing what she is passionate about and having such a positive impact on the people and communities around her. She’s a rock star.  

What habit or practice helps you manage stress?

I find I have to invest in both my physical health and my mental health to really find balance in my life – especially these days. I make it a priority to find time to work out, even if that just means a walk with my kids or the dog, or a quick HIIT workout if I am short on time. It’s really evident, to everyone around me, when I don’t have any exercise in a given week. Let’s just say, I don’t even like being around myself then.

I also find connecting with my family and friends to be a great stress-reliever. That’s been particularly challenging during the COVID-19 pandemic, but I have been finding creative ways to spend time with people, such as hosting Sunday family suppers over Zoom and playing online games or doing virtual wine tastings with friends. It is important for me to feel connected with my friends and family, and I’m so grateful for the technology that enables us to do so.

For more Career Q&As, click here, or you can check out my monthly newsletter and podcast.

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