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Women-led Remote Startups: A (Naturally) Virtual Roundtable, Part Two


Let’s check back in with the startup CEOs we interviewed who are leading the charge in women-led remote companies from three continents.

In Part One, we covered their startup stories ”and chronicled what they believe are the biggest advantages and challenges of managing remote organizations. Here, they offered some insights regarding their own personal leadership journeys, along with advice for those who are eager to begin their own.

Mentors, whether virtual or face-to-face, played an important role in these entrepreneurs’ lives and growth.

Kate Kendall, Founder & CEO, CloudPeeps: “I created an advisory board early on in my journey at CloudPeeps. One of the advisors is Joel Gascoigne, the cofounder and CEO of Buffer. He’s also a friend and someone I deeply respect, which is important in an advisor relationship. It’s been amazing to see him build out Buffer while maintaining a strong set of values, and transparently sharing the learnings. Joel offers a new perspective on organizational structure, and also on how to lead as a CEO (especially an introverted one). We’re fortunate to have him as a small investor in the company as well.”

Hila Dahan, Co-Founder, 33 Sticks: “One of my mentors early on was my boss (the COO) at CreditReport.com. I was there when we were still hustling in startup mode, before the acquisition by Experian. He gave me a chance to navigate the digital analytics space. I learned from him how to see a business opportunity, dissect it into manageable components, and go after creative solutions. This opportunity to learn the analytics space has exposed me to tactics that I now use every day as I run the operations of 33 Sticks.

Another mentor that I have always looked up to is my mom. She’s an amazing artist, and I learned from her to approach everything with passion and care for other people. Her art embodies concepts of love, peace, and humanity, and I have never seen her compromise her message that everything you do in life should be done with the purpose of being kind to one another. Every morning when I start my work day, I think: ‘What can I do today to help the individuals I work with (my clients) shine at their job?  How can I help my employees have a wonderful experience? How can I make others happy at their job?’ Producing meaningful experiences and delivering value to others has become one of our core strategies at 33 Sticks.

Finally, I would say that the one mentor who has had a transformative effect on my career and growth as a business owner and as a person is my co-founder and best friend, Jason. It’s really tough to take that leap and start a business, and it’s even harder to get through the challenges that come along the way (challenges you didn’t even realize existed). I consider myself extremely fortunate that I get to work every day with a co-founder who mentors me to get better at what I do, pushes me to work harder, and inspires me to refine my strengths and be more strategic with my decisions.”

Ingrid Ødegaard, Co-Founder & CEO, appear.in: “I’ve been lucky to have many leaders who have been great role models in different areas. I learned a lot about how to build an engineering culture that attracts the best developers, and how to manage an engineering and product team. I’ve always had to learn on the job, which makes it important to have a manager who gives you the freedom to try things and fail a couple of times. Recently, I’ve had sort of a mentoring relationship with a user of our product, who also happen to be an expert in SaaS growth marketing. For me, it’s been important to exclusively listen to people who see the vision for the product and what we’re trying to do; if a mentor doesn’t have competence in your area/industry and doesn’t understand what you’re trying to do, I don’t see how it can add a lot of value.”

What about aspiring entrepreneurs who are just kicking off their remote projects—or procrastinating about doing so? Here, our leaders’ advice is equal parts motivational and cautionary. (You may want to take some notes on this next section.)

Kendall: “My biggest advice would be to just start! Don’t wait for anyone else’s permission. I’ve been a startup CEO for over five years, and entered the ecosystem as an outsider. There are so many great accelerators, coworking spaces, networks and resources now – Techstars even just launched a remote accelerator. It’s become a lot easier and more accessible. The other thing is to be vocal and share your experiences while building a remote startup. Laura Roeder of Meet Edgar does a great job of this. I’d love to see more female CEOs championing remote. For me, remote work, could be the biggest driver of equality in the workplace we’ve seen yet.”

Dahan: “If you have an idea for a company you’d like to start, if you have something that you are deeply passionate about, then go ahead and get started. It might sound cliché to say “Just do it… risk it all if you have to”, but it is actually true that getting started is the most difficult part. Not to say that there aren’t a lot of challenges along the way—there are—but getting over that initial fear is really the hardest part. Once you get started, you’ll quickly find people who will step up to support you in your journey. I have been amazed at how many people truly want to see me succeed, who have offered advice, helped me work through difficult decisions, or were just around to give me a much-needed pep talk when I felt like maybe I had taken on more than I could handle.”

Ødegaard:Only hire A-players. If you don’t have competence in an area to know what an A-player (e.g. in marketing or engineering) looks like, try to find someone who does, and ask them to help you with interviewing. Hire people who are smarter than you, even if it makes you feel stupid at times.

Focus on solving real customer problems. Start out with really understanding who your customer is, and what problem you are solving. Invest in continuous user research and dialogue, even if you as the CEO have to answer customer emails (I did for a long time, and still do from time to time). I now try to personally talk to a couple of users every month, as it keeps me in touch with what happens in the market.

Invest in analytics. When you get enough user volume, invest in a good analytics platform that can help you work scientifically and identify problems in the product. Build a process of validating what you change in the product; assumptions are the mother of all f*ckups.

Determine your key metrics. Spend time in the beginning understanding what your key metrics should be, and how they drive your business model. Then focus on executing on them, and measure progress regularly. If you are able to tell a story from your metrics, it’ll be a lot easier to convince investors.

Visualize work that happens, including tasks and priorities. Especially in remote teams, it’s hard for people to keep track of everything that’s going on, so if you don’t invest in internal communication, it’s easy for people to feel disconnected. Visualizing work that happens when people are remote builds trust among members of the team. Find a set of tools that people actually like and use them every day.

Personalize culture and processes. Figure out what kind of culture and process work for you and the people on your team. Each team has a unique set of personalities, and there is no way of doing things that will fit everybody.

Don’t underestimate the danger of burnout. This is under-communicated, but it happens a lot in the startup world. Set limits for how much people should work, and make sure they take time off/vacation. People who are well-rested and happy are much more productive in the hours they work, and can stay in the race longer!”

There you have it: don’t wait for an invitation, don’t ask for permission, and heed this strategic advice as you strike out on your own. You’ll be joining a community of supportive entrepreneurs of all genders who seek a startup world that reflects our own reality.


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