Women Of The C-Suite: Julie Schechter and Monika Shah of ‘Small Packages’ On The Five Things You Need To Succeed As A Senior Executive
By: Candice Georgiadis
Tags: Business

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?

Julie: My backstory is sort of unusual. I started out as an attorney, and while I loved the advocacy and relationship-building aspect of law, I craved something more creative. I’m very much a “move fast and break things” person, and that doesn’t really fly in the legal context. I left law for entrepreneurship, and founded my first company, fitBallet. I’ve been a ballet dancer since I was a kid, so it was live fitness classes in NYC, sort of a combination of ballet and Crossfit. I ran that company for three years, but eventually realized that, while I loved being an entrepreneur, I wanted to run a product-based business with a wider addressable market, something much more scalable. So, I closed my first company and started working on Small Packages.

Monika: My first job was in supply chain and finance, and then I got my masters in marketing. That was really the perfect preparation for being a single digit hire at a start-up, since I have a wide breadth of experience. What really led me to Small Packages in particular was that I believe strong relationships can improve one’s health. Just as much as eating well, or working out, and yet there’s so little emphasis in society on this idea of fostering relationships. So, when I met Julie and understood that those were her key values, and the reason she developed this business, I was totally aligned and excited to join.

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

Julie: I think some of the most “interesting” moments were at the very beginning, when much more established entities would be asking for something (a resale license, or some other specific paperwork) and I’d have to say, “Oh, yes, of course, we’ll get that to you right away!” and then frantically turn to the University of Google and figure out what they were talking about and how to accomplish it. You learn so quickly, not just to think on your feet, but also not to be intimidated when there’s something you don’t know. You can always figure it out, and usually within 24 hours.

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?

Monika: Sure! We were trying to plan inventory in advance for a certain box, and so we started reaching out to our suppliers, to give them a heads up on what we’d likely need for the next six months. Unfortunately, we didn’t phrase that email exactly right…and that meant that we accidentally got 200x what we needed for one of our inventory items. The good news was that it was a delicious cookie, and there’s always somewhere to use that,including just consuming it ourselves! But we learned a great lesson, and implemented a new, super-clear template for our inventory-ordering emails, because our vendors are just as busy as we are.

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?

Monika: To be honest, I don’t think I would have gotten to where I have today, if it wasn’t for my close friends, family, and my partner. Starting your own business requires a lot of support and cheerleading on the side, and you can’t put that burden on just one person. I have also found great support from others who have traveled this same path before as they are able to relate to your highs and lows. Having a large diverse support group is key.

Julie: I completely agree. And in addition to the sheer amount of encouragement we both get from our family and friends, we’re also supported by other women who are walking the same entrepreneurial path, and are willing to give advice and just hear you out when the chips are down. I belong to a group of women who all gather once a month (well, at least we did pre-Covid!) to brainstorm solutions and share what’s going on in our respective businesses. One woman, Annie Evans, really was the “den mother” of that group, and took it upon herself to make sure that we kept meeting, that the group had a structure every time we got together, etc. She certainly wasn’t being paid to do so, but she just saw it as her calling to keep that engine running, and it’s done all of us a world of good.

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?

Monika: I believe your brain is a muscle, so if you’re stressed, you not only need mental inputs like reading and meditating, but also physical activity. So whether it’s doing a workout class or honestly just going on a walk, doing something physical is what really helps me calm my mind.

Julie: I’ll definitely echo the physical activity. As a dancer, that’s always been top of mind for me. The other thing I do is to make an effort to completely tap out of reality at least a few times a week, whether that’s getting really engrossed in a TV series or a great book, or (in normal times) traveling. I find that stress comes, for me, from dwelling in one context for so long that it starts to become all-consuming and the high-stakes meeting or decision feels like the most important thing in the world. Switching contexts helps my brain to regulate a little better, and to see the real size of problems more accurately.

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?

Julie: Our company’s mission is to end the loneliness epidemic, to make it easier for people to connect to each other. In order to do that, we have to have a sense of what their basic needs are: what’s challenging them, what’s keeping them from solving this problem, how can we help? And different people are going to have different answers to those questions, so it’s up to us to make sure that the team we’re assembling is diverse enough to speak to those different vantage points. We’re making big strides in that direction, though we’re certainly not all the way there yet.

As a business leader, can you please share a few steps we must take to truly create an inclusive, representative, and equitable society?

Julie:

I think the way you build your company is a microcosm of the kind of society you’re helping to build. We run a really democratic company, in the sense that everyone is encouraged to weigh in, and Monika and I (as the executives) are very open to feedback. We’re also very conscious of diversity and representation in the imagery we use on our website, and on social media, because we want everyone to see themselves reflected in Small Packages.

Monika:

As we look to scale our team, we’ve found that it’s really easy to look at your own network: what school did you graduate from, who do you already know, etc. But we know that automatically creates an in-group bias, and we want to avoid that. Diversity is important to us, so we consciously cast a broader net and make sure we always stretch beyond our network, when we’re developing our recruiting pool.

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?

Julie: I think the difference is that the responsibility of setting the strategy, setting priorities, rests with executive leadership. It’s the very fundamental steering of the ship that has to be done before anyone else on board can do their job effectively.

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

Monika:

I guess the myth here is that executives are delegating tasks so they can go to fun lunches, and that they’re getting paid well. Given we’re an early stage startup, the reality is that we’re working around the clock, and focused on paying our team first. If you’re looking for the title and prestige, having an executive title at a start-up is not going to get you there. Your focus is instead on trying to motivate your team; it’s more like being a coach and getting your team on board because you’re leading by example.

Julie:

I’d agree. I’ve done every single job at Small Packages. Even though I’ve handed a lot of that work over to other people now, it was crucial for me to have gone through those experiences. You have to be empathetic, have to know what’s hard about a given role, in order to lead effectively.

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

Monika: If you’re at the age of having a family, you may get judged by investors on the level of your commitment to your company. Men aren’t really viewed through that lens. We’re also women solving a problem that is easily understood by other women, and it’s been hard to get a man involved in this conversation when it comes to raising capital.

Julie: Yeah, I think the thumb just sits on the scale in the other direction, when it comes to capital conversations. I’ve seen fundraising conversations with men that fall more into the camp of “tell me how you’re going to make me money,” and with women, it’s often more, “reassure me that I won’t lose my money.” We try to just take it in stride and redirect the conversation.

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

Julie: I thought I’d reach a point where I basically knew what I was doing, on a day-to-day basis! But the great thing is that we’re growing so fast that we’re a completely different company than we were 6 months ago, and that’s only going to continue to be true. So, I’ve tried to mentally rearrange. Instead of racking up a check-mark list of competencies, I focus on the fact that I’m good at figuring out what needs to be done, and then learning that skill, as fast as humanly possible. Shifting that worldview to one where I’m successful as long as I’m learning quickly, has made a huge difference.

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?

Julie: You need to be great at taking feedback. Ultimately, the buck stops with you, and so you have to be able to set your ego aside and approach problems from an open perspective. If you’ve done your job well with hiring, you’ll be surrounded by people who know more than you do on a given subject, so you want to listen to them and make them feel heard and appreciated. And then, on the flip side, you also need to be able to make decisions, clearly (and often, quickly). Nothing makes a team feel shakier than a leader who can’t set a clear direction.

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

Monika:

I don’t know if this is gender-specific advice, but as a leader, you have to realize people are choosing to work for you, when they could be anywhere. We only have so many days in a year, and your team is choosing to spend their time working towards your dreams. You have to make it clear that you’re very thankful for that, and that you share your appreciation for their hard work.

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

Start small and build from there. I started Small Packages with 9 different box types and 3 different price points for each, which made the initial capital investment and logistics pretty intense. The plan has always been to help with our customer’s gifting needs end-to-end, so I wouldn’t say that was a mistake, but we also could have taken our time and built more slowly. Save more money than you think you need. Nothing ever happens as fast as you want it to, whether it’s acquiring customers or raising capital. The best gift you can give yourself is to not also be stressing about your personal finances on top of everything else you’re building. It’s okay to have a day job. Rome wasn’t built in a day, and not everyone is in the position to quit their job and go all in on building a start-up from day one. Beautiful things can be built slowly. Find entrepreneur friends. No one, no matter how supportive they are, is going to truly get what you’re going through unless they also are going through it. You need people in your corner to commiserate and brainstorm with, who are in the same position. Figure out your zone of genius, and outsource the rest as fast as you can. Everyone is really great at some things and not so fantastic at others. The minute you identify your really weak points, you’re that much closer to being able to find the person who complements you and lets you shine.

You are both people 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.

Monika: I’d encourage people to read more. I really enjoy nonfiction, but I’ve found more lately that fiction is just as valuable to me, mentally. I’ve found insights in my reading that I’m able to apply to my everyday life and my work. There’s a statistic that reading increases empathy and compassion, so it’s been one way I continuously learn and grow myself.

Julie: I’d say: the movement toward just reaching out. I think we all have this tendency to feel uncomfortable about the text message or the email that’s been sitting for ages, like it’s gone too long and now it would be weird to reach out to that person and say hi. But the truth is, they want to hear from you! We all want to hear that we’re important to someone, that we’ve been on someone’s mind. I think the world would be an immeasurably better place if we all just sent a “hey! How are you?” text in the moment that we thought of someone.

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

Monika: Walt Whitman said, “Be curious, not judgmental.” It aligns with the mantra of “assuming positive intent” that I value. It makes you remember to take a step back and not be quite so reactive to what you may have heard or seen. It’s a reminder to understand there is more to people or an issue than just a headline and it’s when we go beyond that headline that we can learn to empathize and connect.

Julie: “Everything you want is on the other side of fear.” I think it’s attributed to Jack Canfield. Running a start-up means just perpetually jumping through hoops and learning on the fly, and it’s very easy to get in your head about whether you have the inner fire to keep doing it. But when you can just remind yourself that fear is a natural part of the process, it’s easier to acknowledge it and just keep going.

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.

Monika: We’ll start with an easy one: how about Oprah? I’d also love to meet Kirsten Green from Forerunner Ventures, since she’s the queen of DTC. I read Forerunner’s weekly newsletters written by KJ Sidberry, and I feel like I get a great pulse on startups that way.

Julie: I’ll add Rose Marcario, who until recently was the CEO of Patagonia. I’ve always admired the way she set the strategy for Patagonia to be a product company that added real value to the world, without encouraging blind consumerism.

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