As a part of our interview series called “Women Of The C-Suite,” we had the pleasure of interviewing Alice Default.
Alice Default is CEO & Co-Founder of Double, the flexible assistant service for busy executives. Prior to co-founding Double in 2018, Default spent more than six years building productivity tools at Microsoft, Sunrise Calendar, and Front, where she learned technology platforms could provide only limited productivity improvements for overwhelmed company leadership. Today, she enables executives to improve their efficiency by providing experienced, professional assistants along with the tools and coaching necessary to become a better leader.
Thank you so much for joining us in this interview series! 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 became passionate about productivity during my time at Sunrise Calendar, which was an app with a cult following that was ultimately acquired by Microsoft. That experience taught me that the way people spend their time is ultimately how they spend their lives. Being productive isn’t just about increasing your output at all costs; it’s about living a better life where you get to focus on what matters most to you.
That promise of a more focused, more balanced life is what drives me. After Sunrise and Microsoft, I realized that even though productivity apps could boost your output, technology still falls short compared to the skill and precision of a human. Double fills this gap between tech automation and human excellence for modern executives, as well as executive assistants.
For executives, Double provides a hugely valuable resource that was previously available only to businesses who could afford to bring on a full-time executive assistant. Double customers reap the benefits of executive support without the burden or expense of hiring an employee. Moreover, the Double platform enables effective delegation between execs and Double assistants with tools that make onboarding, communication, and task management seamless. The platform has also recently expanded to support effective delegation for entire executive teams.
For executive assistants, Double offers flexible, remote jobs that are still in the corporate sphere. Most Double assistants identify as female, and with women disproportionately impacted by job loss over the last year, Double has witnessed an influx of demand for its remote EA positions. We receive more than 3,000 applicants for our assistant positions each month. Given the shift in priorities in the last year, many people are seeking remote roles that allow them the flexibility to work from home while also managing caretaking responsibilities or other professional endeavors. Double gives these highly qualified individuals that opportunity.
Can you share the most interesting story that happened to you since you began leading your company?
Since getting started, I have loved getting to know our growing community of Double assistants. As a remote company, I don’t always get to meet these assistants in-person so I try to make that happen whenever possible, and it has quickly become one of my favorite parts of the job. I am amazed every day by the power of this community and the relationships it has created.
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?
While fundraising our pre-seed round, I needed to fly to Paris to pitch investors on a Monday following a full weekend with friends. Trying not to miss out on any of the fun over the weekend, I decided to take a red-eye on Sunday evening and go directly to the pitch after I landed.
It was one of my worst pitch performances I’ve ever given. The important lesson I learned was to plan ahead and reschedule if necessary. Back then, it seemed impossible to request to reschedule but now that I am more experienced, I know that the people in the room would likely not have cared.
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?
I have a great deal of gratitude for my former boss at Sunrise who believed in me even more than I believed in myself. All entrepreneurs experience imposter syndrome, especially at the very beginning when you are forced to ask yourself if you are capable of success. This question is especially difficult to face for women, who often have the added challenge of pursuing goals that have never been achieved by a woman before. Add that the technology is an industry dominated mostly by white males on top of that, and the view of a path to success nearly disappears.
My former supervisor taught me the importance of being able to see yourself from someone else’s perspective. I was only ready to leave my previous job and forge my path to entrepreneurship when I accepted his support and began to see what he saw in me, in myself. Now, if I ever doubt myself, I try to see myself from someone else’s eyes and it helps me to realize how capable I really am.
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?
Like most others, the last year has truly tested my work/life balance. As a business leader, especially in technology, there is a lot of pressure to always be “on,” and this idea that I’m available all the time has led me to burnout in the past. I have learned that my personal and professional success rely on alleviating stress not just ahead of a high stakes meeting or decision, but as a part of my everyday lifestyle.
I set hard boundaries for working hours and use my free time to replenish my mind and body, but I also have moments of weakness when I am tempted to continue working beyond my scheduled time. That’s why I made it my New Year’s resolution in 2021 to schedule my free time with more manual activities, like weaving, yoga, and cooking. I also have a rule for myself that I do not answer emails outside of work hours and have not done so in more than two years.
When I use my time outside of work doing something I love, it prepares me to return to work the next day a better leader than I left.
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?
I believe strongly in the value of building a diverse company, and incorporating many different perspectives and viewpoints in our daily collaboration. We’ve seen over and over again in just the past few years that companies with diverse leadership teams are able to better innovate and drive successful outcomes while companies who lack diversity or build monocultures fall into their own blind spots.
While Double is still a small company, we began conducting D&I surveys when we had just 15 employees to collect data and feedback as we prepare for future growth. I’m proud to say that Double has a leadership team with strong female representation, but I know we need to improve our racial diversity at that level. Understanding where we are today has been critical to informing our hiring roadmap and recruiting practices. It has also helped launch conversations that lead to improvements in the way that we build an inclusive culture, such as hosting more D&I learning talks, creating spaces for honest conversations, and iterating on our recruiting practices.
On a very practical level, having a diverse company also enables us to better serve our customer base. We have customers coming to us from all over the US and Europe, from all different industries and backgrounds. By building a team that comes from as many different backgrounds as our customer base, we can better empathize with their day-to-day experiences and needs in the business world.
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.
Businesses in this country are in a unique position to drive meaningful change when it comes to diversity and equality. I’m not naive enough to believe that a few companies launching better D&I programs will change the world, but I do believe that business leaders have more impact in the lives of their employees and communities than they sometimes accept responsibility for.
As table stakes in today’s world, I’d like to see more CEOs and founders commit to a few things:
- Inclusive hiring practices. Hiring employees from a strict set of ten elite universities, or relying on employee referrals for most of your hiring will only build a company where everyone looks, thinks, and acts like each other. Investing in recruiting beyond your immediate network will provide access to a greater candidate pool, and ultimately brings in even more candidates with unique and valuable perspectives.
- Fair pay standards. It’s inexcusable that we have to hear over and over again that the gender and racial pay gaps still persist. At Double, we’ve created a totally transparent compensation structure based simply on role levels and years of experience to ensure visibility and accountability in this space.
- Reflection and education. As a leader, it’s on you to continually educate yourself on the issues in your immediate community and the country as a whole. Having hard conversations with experts and your own employees is foundational to knowing where you need to improve as a leader and a company.
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?
Early in the lifecycle of a business a CEO is often doing many roles to fill in gaps throughout the organization that may not have been hired for yet. While other leaders in the company like a Head of Sales or Marketing have a functional role, a CEO has to be a horizontal player. In my experience, a CEO also has the unique responsibility of flexing between long-term visioning to set the mission and company strategy, with a very short-term focus of tactical execution. Finally, CEOs need to constantly be re-inventing their role as the team grows, much more than others, which can cause a lot of pressure as the CEO is always learning and figuring out new things.
What are the “myths” that you would like to dispel about being a CEO or executive. Can you explain what you mean?
Our audience at Double is CEOs and executives of high-growth companies. When we are onboarding new customers to our platform, we talk to them about their current pain points and daily challenges. Almost universally, these smart, confident leaders tell us that they are overwhelmed with the pace of their job and feel like they’re falling behind. So the first myth about being an executive is that you have it all figured out!
But beyond that, there are a few specific themes that we hear from executives consistently that they are struggling with:
- Delegation: It’s a common perception that executives delegate every single task and don’t do anything themselves. The reality is that nearly all of Double’s executive customers start out by labeling themselves as “bad delegators” or the type of person that is still doing everything themselves. Our platform aims to make delegation easier through tools like a task management app, a Chrome extension, and Slack integration.
- Administration: CEOs and entrepreneurs tend to be ideas people, but it’s common for them to come to us explaining that they spend more time doing bookkeeping and administrative tasks than they imagined. Entrepreneurship and business acumen aren’t mutually exclusive among business leaders.
- Time Management: There is a myth that CEOs should always be on — always connected — otherwise, the business is going to crash. The reality is that taking time off, taking breaks, disconnecting from the business and focusing on finding a strong work/life balance is actually one of the most beneficial things you can do for your business, team, and yourself.
In your opinion, what are the biggest challenges faced by women executives that aren’t typically faced by their male counterparts?
As a sample size of one, it’s hard for me to know which challenges I’ve faced because I’m a woman, and which I’ve faced simply because starting a business is hard. But based on my own experience as well as other women founders in my network, it is clear that we haven’t reached gender parity yet. Sometimes this comes out in big explicit ways, but often it’s much more subtle. I once had an investor tell me I was too vulnerable during a pitch because I was honest about potential challenges the company may face. Would he have said that to a male founder?
What is the most striking difference between your actual job and how you thought the job would be?
Before I took on the role of CEO of Double, I had a premonition that, at some point, there would come a moment where I would have things figured out. In reality, this “moment” occurs over and over again, then is quickly replaced by something else I have to figure out. I frequently think of it as similar to playing Mario Kart: just as you’re getting comfortable with the current speed, it switches to a fast one and you must regain control, or a banana peel is thrown in your path and you have to diverge.
I am constantly pushed outside of my comfort zone, and that impacts the milestones we reach as a company. As soon as we hit them, it instantly feels like it was easy, and my attention moves to the next thing to figure out.
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?
While there are certain characteristics that I believe can improve performance among executives, especially in the C-Suite, I do not believe that there is an “ideal” type of person to fit a business leadership role. When we profile success in this way, it can seem like there is only one type of person capable of achieving it, which is one of the reasons there is so little diversity in the technology industry.
However, there are certainly some characteristics that I have noticed appear frequently among Double’s executive audience.
Building a company is not a short-term project. Executives have to grit their teeth and remain determined for years on end — through all the highs and lows — to see ultimate success. Staying determined to achieve your mission and long-term objectives helps you remain grounded when there are short-term challenges along the way.
The best executives are also curious, and always learning. When you first set out to start a company, you may know a lot or a little about the problem you’re trying to solve. But staying curious about the needs of your customers and potential solutions to those needs enables you to stay open to new ideas and information. Three years ago I started Double with some ideas of what our product would look like, but through thousands of hours spent with customers I’ve stayed curious and found new ways to tackle our audience’s core problems.
Finally, it’s critical to build a trusted group of other founders or executives and maintain a connection with them. This role can be lonely or isolating at times, as you’re the one person ultimately accountable for the success of your company. Having other people to lean on for support and input has helped me immensely.
What advice would you give to other women leaders to help their team to thrive?
To all leaders, regardless of their sex, I’d recommend leaning into empathy to help your team thrive. Building a practice of empathy with your team makes it possible to identify and understand the very human challenges that may be getting in the way of business outcomes. But unless you invest the time to talk with your team and see what’s happening in their lives, you’ll never understand why work is or isn’t happening.
How have you used your success to make the world a better place?
I’m really proud that Double has been able to create an entirely new type of remote employment for a largely female workforce that allows for meaningful work with much more flexibility than a standard corporate environment. We have more than 100 assistants in our Double community now, and we hear all the time how Double has enabled these professionals to stay involved in business-critical work while enabling them to spend more time with their family or pursue other endeavors.
What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)
- No matter how important the person is in front of you, no one knows your business better than you do. As a first time founder, I used to think that people with more experience would know better than I did, even on topics like the direction the company was going in. In the past, I have taken a few wrong turns because I listened to them vs. trusting myself.
- Let go of things and magic happens. I used to want to control everything and give my input and ideas on everything. I learned that when I did that, I limited everyone else’s creativity because they would always want to follow my ideas, even though they had way more context on topics. Over time, I’ve learned to let go and give people space, and they always come up with way better ideas than mine.
- Patience is a CEO’s most valuable ally: everything takes way more time than you think, from product to growth to fundraising. You need to learn that your first try is probably never going to be the right one.
- Letting go of people can actually be a good thing for them as well. I postponed a few tough conversations because I was afraid I would crush the other person, and held on for too long after it wasn’t a good fit anymore. When I’ve had to have these difficult conversations, I actually realized that in some cases, it was also a relief for them because they hadn’t been happy in the role for a while, and this gave them the opportunity to think about what was next.
- Don’t solve a problem before it’s a problem, there’s already too much to do. There are tons of things you could fix, always — but if you’re trying to do it all, then you’ll just burn out. Focus on the problems that have an actual impact on your team, your clients, your community, your business. And accept that everything else will just have to do for now.
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 would love to inspire others to commit to work/life balance. For me, that has been setting the boundary of no emails during weekends and vacations. It’s probably my French side showing, but I truly believe in the power of disconnecting and the impact it can have on the business when you’re feeling really refreshed. It’s not easy, and it takes a lot of self control, but I know this small but significant change has made me a more present leader.
Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?
“Do the best you can until you know better. Then when you know better, do better.” — Maya Angelou
As a founder, it can be very easy to be completely consumed by this feeling of never doing enough. There is an infinite list of more to do — more fundraising, more emails, more hiring — but there is only a finite amount of time and energy and the paradox can be crippling. Moreover, the pressure to know how to do everything and do it well is often enough to get too scared to do anything at all.
In times when I’m feeling low, this quote always reminds me that I’m doing my best until I can get better. My role as CEO is a constant work-in-progress, and learning as you go is how you get better at it.
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 would love to meet Kim Scott, the author of Radical Candor, who has been a great inspiration for me and my management style. As we’re all moving to a more remote world in the wake of the pandemic, I would love to know how she sees management, including giving feedback, and team building evolving.