Office Hours: I'm co-founder of Pillar, an online wellness coaching platform and former employee #1 and Chief of Staff at L., acquired by Procter and Gamble.Featured

Hi everyone - Iโ€™m Caroline Early, co-founder of Pillar, an online wellness coaching platform dedicated to building the future of proactive health starting with redefining our relationship to stress and burnout. Check out our website to join the waitlist - link above!Prior to Pillar, I was employee #1 and Chief of Staff at L., an organic personal care brand for women. The company grew to be the fastest growing feminine care company in the U.S., selling to Procter and Gamble in 2019. L. made over 250 million pads accessible through female entrepreneurs with our one-one-one give back model. We were also the first solely female founded Y Combinator startup to have an exit!Ask me anything about the founder journey, managing wellness, social enterprise and more.
Thanks so much for joining us @carolineearly!Elphas โ€“ please ask @carolineearly your questions before Friday, March 26th. @carolineearly may not have time to answer every questions, so emoji upvote your favorites ๐Ÿ”ฅ๐Ÿ‘๐Ÿพโž•
What's something you learned from your journey building L. that you're now using at Pillar?
At L., I witnessed the power of a rapidly growing company to drive impact across its products, brand and give back model. In school, I became quite fascinated with social enterprise, which is what led me to join L. in the early days. I'm now committed to building solutions to social problems, but beyond that have witnessed how it can be an incredible motivator for myself, my team and our partners particularly when the going gets tough. At Pillar, weโ€™re committed to reducing the socioeconomic disparities in health through empowering coaches to advance health education as entrepreneurs within their communities. For every coaching session, one is made accessible by funding the National Board of Health and Wellness certification for a coach from a low-income community.
Procter and Gamble, ahem..
Hi @carolineearly,How do you cultivate wellness as a co-founder?
It's been a very long journey to finding wellness as a professional. For the majority of my career I've fallen into the trap of assuming the expectations of those around me at my own expense, as many women often do. During my time at L., I admittedly pushed myself to the limit and was left with health issues that forced me to take responsibility for my experience if I wanted to be a leader with Pillar. A major shift was finding the confidence to honor my value through investing in the boundaries and resources that supported my wellness for the long-haul. I now work with a health and wellness coach to tackle a combination of cultivating my inner leader while navigating an elimination diet, which has been revolutionary for my mysterious chronic fatigue. Unfortunately, endless coffee will only take you so far! I found that out the hard way.
Thank you! "A major shift was finding the confidence to honor my value through investing in the boundaries and resources that supported my wellness for the long-haul" - love this!
"Chief of Staff" can take on so many different meanings at different companies. What was your experience like in this role? What were the best/worst parts? Who is a great Chief of Staff candidate?
It's true - I've come across a huge variance in terms of individuals who have also occupied a Chief of Staff role. My main takeaway is that it's largely dependent on the executive with whom you're more or less attached at the hip. In that way, it's essential that your skills compliment theirs while also having the confidence to step into their place when they're absent and the team requires an executive decision. Beyond that, the role requires an ability to do many different jobs at once because when there's any gap in the team, it inevitably falls on your shoulders in addition to your recurring responsibilities. The worst and best part, was the level of responsibility. When sh*t hits the fan, you're a critical part of the solution but it also means late nights with minimal glory. That being said, it provided unparalleled visibility as far as what it takes to make a company successful - for example, I was the first team member under the tent during our acquisition and led the integration with P&G after the sale was complete. If you have the determination, grit, and patience to take on what can be a bit nebulous at times, it can be truly transformative for your career. One way to sum it up is a quote from our former VP of Ops, "you're the wind beneath all of our wings".
Thank you! I appreciate your thoughtful response. Have a great weekend!
Congratulations Caroline on your accomplishments! As a healthcare ops exec, and after a year of fighting a global pandemic, I am more sensitive to the need to redefine my relationship to stress and burnout. I have formally joined the Pillar waitlist :) I am looking forward to becoming a client! Also, I have been wanting to transition my career even before the pandemic to a health tech startup. I am unsure where to start. Might you have any advice for me?
Thank you so much Jennifer! Your concerns are right up our alley. As far as approaching stress and burnout in a new way, Iโ€™d first consider doing a triage from an integrative perspective. Try ranking the following categories on a scale of 1-10 based on your current state, and where youโ€™d like to be. These categories might include: Physical Health, including Sleep, Movement and Nutrition as well as Emotional Health, Career, Finances, Romance, Family + Friends and a combination of Fun and Self-Care. What would then be the action items associated with each to advance the flag? Another great sanity check is reflecting on your core values, to ensure your goals are aligned with expectations that are truly your own. As far as joining a health startup, Iโ€™d consider looking at TechCrunch for funding announcements that feel values-aligned and from there, reaching out to the founders on Linkedin or through their jobs page, if applicable! One layer of complexity is that startups are traditionally cash poor, so it will be important to weigh your own needs and then select a company that is at a stage where theyโ€™re able to meet them both monetarily and in terms of the role. :)
Thanks @carolineearly for sharing your experience. I founded Ready set Dinner to help families answer the ever-reoccuring What's for Dinner question. We launched the first version of our meal-planning and shopping-assistant this year and we are currently looking to bring some strong advisors on board that can help us with networks into the grocery retail industry and on the fundraising journey.Do you have any tips and tricks on bringing advisors on board at a very early stage, especially getting those that are most complementary to the current teams' skill set (and therefore also "far" away from the own network)?Thanks again.
A cold email can really go a long way, if it clearly articulates the mission of the company and how it's relevant to that persons domain. Particularly with persistent follow ups! I find that asking people about their expertise can yield incredible results, because somehow everyone enjoys speaking about their passions to an engaged audience. This was exactly how we brought on Margaret Moore, the co-founder of the National Board of Health and Wellness Coaching, founder of Wellcoaches and faculty at Harvard. If you connect with someone who turns out not to be the right fit, kindly ask them if they would be willing provide a personal introduction to someone in their network who might be more appropriate. Beyond that, my co-founder and I have been lucky to land introductions to strategic advisors through our networks grown over the course of several years in previous roles. I hope this helps!
What do you do about insurance at Pillar? What kinds of safeguarding or public liability risks are there and how do you manage them?
What advice would you give to a founder who is trying to reach to a new country?
Hi @carolineearly,Thank you for taking part in office hours! โ˜บ๏ธAs a female founder and the first solely female founded business to go through the process, what advise would you give to female founders applying to Y combinator vs their male counterparts? Was there anything you felt was different for you as a female on the journey? As someone who has scaled teams, what is your advice when looking to make early hires? Thank you!
Of course! When applying to YC, it's essential to have a mature idea that's well articulated in a concise manner. For example, it's useful to think about your "one liner" when it comes to describing your company. If you're able to make it to the interview, it's critical to not only have a strong pitch but also to identify the gaps in your strategy and create bullet proof answers to each one. I'd advise you to embrace your unique style in a way that conveys authentic confidence. There is absolutely no replacement for practicing your pitch repeatedly with an audience in order to optimize for a powerful presence - push yourself! In the early days of Pillar, I used YC's start-up school as a framework for my ideation process as it can get super abstract. As a result, I realized how much amazing content there is online as far as the principles that YC values. For hiring, we were introduced to the phrase "hire slow, fire fast". While there can be hair on fire moments in a startup environment, it's critical to ensure that new hire is a strong fit for the role and the company culture because if they aren't, it can only create more headaches. There's value in doing a contracting period initially to get a feel for each other, and sanity check both that the potential hire enjoys working for you and visa versa. Otherwise, ensuring they are willing to wear multiple hats, roll up their sleeves, take initiative when guidance is unavailable, have patience when the going get's tough, and believe in the mission are key.
Hi! Itโ€™s great to see founders in the health space ๐Ÿ˜ŠHow does the team at pillar keep up with research news in the health space and best practices?How do you deal with sensitive data ?
This is a great question and a massive motivator for myself and my co-founder when starting Pillar. Shockingly, thereโ€™s a 17 year gap between the latest studies and when it reaches your primary care doctorโ€™s office. The question then became, how can we create a proactive, continuous care model with coaches who are trained in an evidence-based approach? After interviewing over 100 people, we found that 50% of those we spoke with wanted a health coach but didn't know where to find one that was credible. Not long after user interviews, we discovered that the National Board of Medical Examiners also saw the need for credibility in the health coaching industry giving way to the introduction of national standards in the last 5 years. Instead of building our own standards from the ground up, we currently only work with coaches who have formal training from programs that are affiliated with the National Board. These include programs at Georgetown, California Institute of Integrated Studies, Duke, Wellcoaches and more - all having a strong focus on the latest research in integrative health, lifestyle medicine, and motivational theory. As far as sensitive data, we were surprised to find that a lot of off the shelf tools have HIPAA complaint options!