Liana Douillet Guzman of Skillshare: Why You Should Value Journey Over Destination

Value journey over destination. As we’ve seen this year, it can be impossible to predict how one decision will impact the path your life will take. So instead of focusing on the end point, focus on the journey. Always take the job where you’ll learn the most, even if the jump doesn’t make a ton of sense on paper. Most people didn’t understand my move from COO at Blockchain to CMO at Skillshare, but I saw the opportunity as a great learning experience and now I couldn’t be happier with my decision.

As a part of our series about strong women leaders, I had the pleasure of interviewing Liana Douillet Guzman.

Liana Douillet Guzmán is the Chief Marketing Officer at Skillshare. As CMO, Liana helps to set Skillshare’s long-term strategy and drives Skillshare’s growth and retention through brand, acquisition, communications, partnerships and sales.

Prior to Skillshare, Liana spent was COO at Blockchain, where she was responsible for identifying areas of opportunity and differentiation as well as overseeing the Expansion, Partnerships, Operations, Talent, User Success, Research, Marketing, Growth and Communications functions. Before joining Blockchain, Liana led Branding and Communications at Axiom.

As Chief Marketing Officer at Skillshare, Liana Douillet Guzmán helps set the company’s long-term strategy and oversees brand, acquisition, communications, partnerships and enterprise.

Prior to joining Skillshare, Liana was the COO at Blockchain where she helped the company increase revenue, 6x the team to nearly 200 people, expand into new product lines and geographies, and grow its user base 10x to over 40M.

She split her childhood between Puerto Rico and Connecticut and, along with her wife and two kids, calls Brooklyn home today.

Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

I’ve always loved the idea of tapping into the way people apply novel solutions to nuanced problems. As an undergrad, I was convinced the best way to do that was to become a lawyer, so I planned to take a year off after graduation and then head to law school. A few months into a paralegal role, I realized the legal profession was bound in precedence and almost entirely focused on applying existing solutions rather than finding new ones. Right around the time I came to that realization, I was offered a role in marketing. I hate to admit this but, at the time,I thought marketing was what people did when they didn’t want a serious career. Little did I know, the thing I thought I loved about law — thinking outside the box and making complex ideas digestible and identifiable — was actually far more applicable to a career in marketing.

For the last 15 years, I’ve been helping companies do just that. I started by helping to disrupt the legal profession at Axiom, which ushered in a new era for legal services. That experience gave me a great foundation for helping bring blockchain technology to the masses, as’s first marketing executive and eventual COO. Most recently, I returned to my Marketing roots as Skillshare’s CMO.

Can you share the most interesting story that happened to you since you began leading your company?

I’ve worked for 3 very different industries, jumping from law to fintech to creative learning, but all have been with mission-driven organizations that change lives for the better. What I find most interesting is the stories of how those companies do that. At Blockchain, we helped a woman in Afghanistan who was able to use cryptocurrency to hold value independent of her father, husband, or brother for the first time in her life. More recently, there’s the world traveller who broke her hip and turned to Skillshare to learn how to create a travel blog to ease the pain of cancelled trips; the woman who used Skillshare to navigate the death of her father and is now a successful illustrator; and the mom who finds a way to connect with her teen by taking classes together. These are the stories that power my work and passion.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

When I was at Axiom, the first big campaign I worked on was this guerilla marketing campaign where we drove from law firm to law firm handing out flyers. We’d attach these flyers to employees’ cars in the parking lots, and then drive off to the next firm. I was in charge of driving the team around in a minivan, and at our second to last firm of the day, a security guard saw us and started running after us. So, with the back doors of the minivan totally open, I started driving away as my team members sprinted back toward the minivan and hopped in.

It was a comical mess, and we really should’ve been better prepared for that sort of run-in — we were literally pasting flyers to peoples’ cars. But what I learned from that incident is that while you’ll make mistakes, what matters most is the people you have around you. And if you can laugh with those people after a long work day, all the better.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

It takes a village and I am so grateful for mine. I’m grateful for parents who believed in me so much that I had no choice but to believe in myself. I still look to my first real boss, Courtney Bowerman, who has since become a dear friend, for guidance. In a world where we’re taught that leadership is firm and exacting, she leads with empathy and was willing to push me and tell me what I needed to hear, even if I didn’t want to. I have friends from as far back as middle school and college whose careers have mirrored mine and act as a sounding board and support system. And last, but certainly not least, my wife Nicole. It would be impossible to pursue this career (and a lot less fun!) if not for her 50/50 partnership and unending support.

In my work, I often talk about how to release and relieve stress. As a busy leader, what do you do to prepare your mind and body before a stressful or high stakes meeting, talk, or decision? Can you share a story or some examples?

A few years ago, I was about to walk into a high-stakes meeting but was experiencing back pain so I quickly ran through a set of back exercises and that’s been my trick ever since: connecting to my body in that deliberate and measured way, and the required counting and breath work centers and calms me. When I’m preparing for a big speech or presentation, I also practice (aloud) to the point of memorization. That muscle memory is the greatest tool against nerves and unexpected turns.

As you know, the United States is currently facing a very important self-reckoning about race, diversity, equality and inclusion. This may be obvious to you, but it will be helpful to spell this out. Can you articulate to our readers a few reasons why it is so important for a business or organization to have a diverse executive team?

The reasons are endless. As a lesbian Latina, I can tell you firsthand how difficult it can be to navigate a corporate world in which you don’t see people who look like you at the top. We owe it to the talented millions who don’t see themselves in today’s largely white executive teams to build a different vision. Similarly, as an executive, I know that my perspective within the gay and latin communities adds a richness to our conversations that would be otherwise lacking. And every person at the table who can bring an underrepresented view adds another layer of richness. Beyond that, companies that can connect with their audiences authentically build stronger brands and more sustainable businesses. That connection is impossible to make if your team isn’t a microcosm of the world you’re serving.

You don’t have to take my word for it. Research has shown there is a statistically significant relationship between a diverse leadership team and better financial performance.

As a business leader, can you please share a few steps we must take to truly create an inclusive, representative, and equitable society? Kindly share a story or example for each.

As business leaders, we have a responsibility to use our positions of privilege and power to create an equitable, representative, and just workplace. Doing so requires purposeful hiring practices and supporting diverse hires once they’re on the team. At Skillshare, we have made a commitment to ensure that 50% of our team is from an underrepresented group. Setting a quantifiable goal like that ensures that we’re focused on impact rather than merely intent. In order to get there, we have a dedicated two-week period during which we only source candidates from underrepresented groups by proactively reaching out to diverse candidates via Linkedin, posting job descriptions on POC-specific job boards, and having our affinity groups amplify the opening to their networks. We also have a recruiter focused on building more diverse pipelines for each role. Within the interview process itself, we’ve been mindful to create scripted interviews, conduct interview training, and craft interview kits for every role to help us make objective decisions and avoid unconscious bias. Even with these efforts, we know we have to continually evaluate our progress and revisit our long-term strategy to really move the needle. We recently partnered with Paradigm to ensure we have the most inclusive process possible and to identify any bias. Once onboard, we need to ensure employees feel safe and supported, by continually reviewing our processes, creating and funding multiple safe spaces for all employees to share their perspectives and experiences, ongoing manager training on building inclusive teams and workspaces, or a trusted people operations team. Of course, these are just a few of the things we’re doing today but I believe all should be standard practice.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. Most of our readers — in fact, most people — think they have a pretty good idea of what a CEO or executive does. But in just a few words can you explain what an executive does that is different from the responsibilities of the other leaders?

The real job of an executive is not to have the right answers but to hire people who do, ask them the right questions, and give them the autonomy to get their job done.

What are the “myths” that you would like to dispel about being a CEO or executive. Can you explain what you mean?

When I was younger, I believed that senior executives were their own bosses. While it’s true that there’s a certain level of autonomy that comes with seniority, being a successful executive is all about being part of a team. Even if they may have the final say in many decisions, leaders still have to be flexible and attentive to other people’s voices.

I also used to believe the CEO/executive track was just a straight shot to the top. I quickly learned that everybody has a unique story, an interesting path to where they end up in their careers. Sometimes it’s two steps forward, one step sideways; sometimes it takes a few steps backwards before going forward.

In your opinion, what are the biggest challenges faced by women executives that aren’t typically faced by their male counterparts?

It’s been 8 years since Anne Marie Slaughter’s assertion that women can’t have it all and — as COVID has laid bare — not much has changed. Women continue to be disproportionately responsible for domestic tasks and childrearing. And while I think it’s imperative that couples better share domestic responsibilities, I want to be clear that I don’t want to be married to someone who will handle everything at home so I can focus exclusively on my career, as so many men have done for generations.

I want the corporate world to shift so that I can do both well. This change needs to come from both work and home cultures. Companies should talk to their employees and figure out a work-life balance that fits them best, and I’d like to think that couples are having these same important conversations with each other.

What is the most striking difference between your actual job and how you thought the job would be?

I believe that it’s really important to visualize where you’re going, but not how you’ll get there. Having a clear vision for your end goal provides a north star and a clear framework from which to make decisions, but keeping an open mind about how you’ll get there allows you to think outside the box and see opportunity in even the most unexpected corners. With that in mind, I joined Skillshare because I believe that we can create a globally-recognized brand that changes millions of lives for the better. And I’m proud to say that the reality is keeping up with the vision. That said, I didn’t have any expectations for how we would get there; I knew I needed to meet and build the team before shaping that vision, but I can say that I have found a lot of satisfaction in the unexpected.

Certainly, not everyone is cut out to be an executive. In your opinion, which specific traits increase the likelihood that a person will be a successful executive and what type of person should avoid aspiring to be an executive? Can you explain what you mean?

Can I disagree with the premise? I think it’s true that not everyone is cut out to be an executive, ONLY if we continue to expect executives to look like they have for the last 40 (or 400!) years. But I would argue that we need to expand our vision of leadership and give everyone who wants to become an executive access to the mentorship and opportunity that for too long have been reserved for too few. For instance, since my first child was born 5 years ago, I’ve been among the first to leave the office so I can spend quality time with my family. A decade ago (and even today in less supportive environments), setting those boundaries would have limited my ability to assume executive roles, but I’ve been fortunate enough to work for CEOs who have expanded their vision of what a leader looks like and who value my output more than my facetime. That said, I think it’s important to recognize and respect that not everyone wants to be an executive. Personally, my career is a source of fulfilment, but for others, a job is simply a means to an end. It’s important to recognize that the contributions of individual contributors who have no desire to rise the ranks are equally important.

What advice would you give to other women leaders to help their team to thrive?

I vividly remember being on a call with three senior women and the company’s (male) President. All of the women on the call were hiding in a closet or a corner of their apartment, ensuring that their kids would not appear in the background. The President of the company, on the other hand, interrupted himself twice to answer questions being asked by his kids. I realized in that moment that there is an immense personal cost to trying to separate our personal lives from our professional ones — and that men aren’t paying the price. In doing so, we have less to offer our teams and, worse yet, we further the narrative that women can’t be successful at work while also prioritizing their home lives. That simple shift in thinking has helped me become more present and available to my team and has shown them via action, rather than word, that they can bring their full selves to work.

How have you used your success to make the world a better place?

As I mentioned earlier, I’ve built my success working exclusively for companies that are designed to make the world a better place. Beyond that, I make sure to mentor women in my field.

I had the great fortune to co-found The Pink Agenda when I was 23. I wanted to make a difference, but found there weren’t many organizations focused on young professionals. We set out to change that, proving that fun and philanthropy aren’t mutually exclusive, and raising millions for breast cancer research and awareness along the way. These days, I’m also really focused on and financially committing to organizations focused on racial justice, climate change, and women’s and LGBTQ+ rights.

What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

  1. Expect — and pursue — the unexpected. I graduated college certain that I would go to law school and had a pretty negative view of what it meant to work in Marketing. But within 18 months of graduating, I was disabused of both notions. Ten years later, I got a call from a recruiter asking if I would be interested in a role at a cryptocurrency company. I responded that I thought of crypto as unicorn monopoly money and politely declined. Luckily for me, she convinced me to take a coffee with the company’s CEO and four years later I was operating as his number two, helping to usher in a period of unprecedented growth. And then I woke up one day and realized that Marketing and Communications were the most fulfilling parts of my job as COO, so despite the advice of many advisors, I made the jump to a CMO role at Skillshare. Needless to say, my path has not been a straight one and the opportunities I’ve found most challenging and satisfying were also the least expected.
  2. Value journey over destination. As we’ve seen this year, it can be impossible to predict how one decision will impact the path your life will take. So instead of focusing on the end point, focus on the journey. Always take the job where you’ll learn the most, even if the jump doesn’t make a ton of sense on paper. Most people didn’t understand my move from COO at Blockchain to CMO at Skillshare, but I saw the opportunity as a great learning experience and now I couldn’t be happier with my decision.
  3. Who you work with matters more than what you’re working on. Skillshare is the first company I’ve worked for whose product I actually used before joining the team. Legal services and cryptocurrency, on the other hand, were not passions of mine before joining the ranks at Axiom and Blockchain. That said, I knew that the teams at each would inspire and challenge me. I learned from them in ways I couldn’t have predicted and credit much of my success to those experiences.
  4. The smartest people in the room are the ones asking the questions. It takes confidence to ask questions, but the ones who speak up and do so are reaping the benefits. I was nervous to raise my hand at the start of my career, but I’ve found that asking thoughtful questions keeps me engaged and helps me to better understand my industry.
  5. Hire the right people and trust them to do their jobs well. In the startup space, lean teams are a badge of honor and it’s not uncommon for employees to touch many areas of the business. At Skillshare, our founder Michael Karnjanaprakorn even had a hand in our original logo design. It’s important, however, to eventually call in the experts necessary to help the company level up and be thoughtful and intentional about adding new team members.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.

I’d love to see us invest in universal childcare and high-quality early education. Their ripple effects have the ability to close opportunity gaps, not only in the early years of a child’s life but for years to come, which in turn can create more opportunities throughout adulthood.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

David Allen said, “You can do anything but you can’t do everything.” Once you realize you can’t do it all, you’re forced to focus on the things that will have the greatest impact on the world and will bring you the most joy and fulfillment. As a senior executive, this mindset has helped me get comfortable with the idea that I couldn’t do it all and needed to hire a team I could trust. Personally, it has helped me manage the balance between my personal and professional lives.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them

I know this isn’t an original answer but, without a doubt, Oprah. My parents divorced when I was 11 and, for the first time, my mom had to work after I got out of school. So, I spent my afternoons with Oprah — she has shaped so much of who I am. Her book club built a reading habit that is still a part of my life today, and I learned everything from makeup application to the importance of meditation from her show.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

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