Betting on yourself, overcoming obstacles, and mission-driven companies with Jen Lyttle (VP of Sales at Aunt Flow)

Jen Lyttle 00:00

That also triggered something in me to be successful enough to not only support my daughter financially but also put her in a situation where she would never have to worry about her health ever again.

Callan Harrington 00:16

You're listening to That Worked, a show that breaks down the careers of top founders and executives and pulls out those key items that led to their success. I'm your host, Callan Harrington, founder of Flashgrowth, and I couldn't be more excited that you're here. Today's guest is Jen Lyttle. Jen is the VP of Sales at Aunt Flow. Jen, welcome to the show.

Jen Lyttle 00:43

Thanks. I'm excited.

Callan Harrington 00:44

I am as well. We've worked together for a long time now.

Jen Lyttle 00:46

Yes, we have.

Callan Harrington 00:47

Before we dive into that, why don't you tell us a little bit about Aunt Flow and what you're doing for them?

Jen Lyttle 00:53

Definitely. Aunt Flow is a company I've been following for a long time. They started here in Columbus in 2018. The CEO and founder, Claire Coder, started the company because she had started her period in public, had no supplies whatsoever, and realized that bathrooms offer everything you need for essential bodily functions except period products. She's been on a mission for a number of years to fix that. We now support stores like Apple across the United States, as well as Google and Netflix, all the way down to your local coffee shop, providing them with free period products. I came on board almost a month ago to help develop their sales strategy across the company, and it's been a really fun ride so far. We just hit all of our January KPIs, which was a big win for me in my first month.

Callan Harrington 01:48

That's excellent. I saw the story you posted on LinkedIn. How did this even come about?

Jen Lyttle 01:55

It is a good story. In 2018, I was at dinner at The Pearl, a restaurant here in Columbus, and I started my period, just like Claire's story, and had an "oh shit" moment. The server, who is a really good friend of mine, told me they had products in the bathroom. It was the first time I saw Aunt Flow products, and I thought it was cool. I immediately Googled who it was, saw that Claire was a Columbus native, and thought it was incredible. I sent her a cold LinkedIn message, just saying that what she was doing was fantastic, and I wanted to stay connected. A year later, I was working for a local organization, came across her products again, and we met in person. We followed each other's careers over time, and a few months ago, she reached out with an opportunity that was perfect timing. So it was about five years in the making since I first met Claire and took this role.

Callan Harrington 03:02

So you knew you wanted to be at this company, but the timing just wasn't right initially. Over time, you nurtured that relationship and ended up being there when the moment was right. Is that correct?

Jen Lyttle 03:15

Exactly. I actually interviewed with the company a few times for different roles, but other opportunities came up that were just better timing-wise. I wanted to make an impact, and this year was the right time for that to happen.

Callan Harrington 03:36

I love that. Where did your career start?

Jen Lyttle 03:39

I'm a Columbus native, born and raised here. I grew up on the east side of Columbus, in Groveport. I had the usual teen jobs, serving tables, bartending. One of my first "big girl" jobs was as a property manager for a company here in Columbus that was scaling quickly. They were building properties, leasing them up, and selling them. That's actually how I met Ilya Bodner, who we both know. I think I rented an apartment to someone he knew, and we connected on LinkedIn. He told me he had a role that he thought would be interesting and asked if I wanted to meet in person to talk about it. I'd never been in inside sales before, so I kind of thought it was a pyramid scheme, to be honest. But at that time, I was a single mom, not making much money, and very money-driven. So I met him in person and we talked about that first inside sales role.

Callan Harrington 04:40

Why did you decide to make the leap?

Jen Lyttle 04:41

Funnily enough, I met Ilya at a coffee shop that doesn't exist anymore, and we hit it off instantly. At the time, he was moving a company called People to My Site over to the Shipyard. He said they had an inside sales role, and it would be the first SDR/BDR they'd hire. They had just landed an account with Nationwide and were trying to figure it out, but they didn't have health benefits yet—no medical, no dental. I had a kid, so I turned the role down and went back to my leasing and property management role. A few months later, Ilya reached out again and said they had benefits now and asked if I wanted to come on board. I said yes, and I became one of the first SDRs/BDRs at the Shipyard, which was a startup here in Columbus. I don't want to say how long ago that was—probably 10 years ago. It was a while ago.

Callan Harrington 05:36

Yes, it was.

Jen Lyttle 05:38

So that was my first saturation into the startup world here in Columbus, and then I kind of moved through the startups, especially in the InsurTech space.

Callan Harrington 05:51

To circle back, you guys met via LinkedIn. Timing wasn't right initially because you had a family to take care of, but as things changed, you felt more comfortable taking the leap. Is that right?

Jen Lyttle 06:11

Yeah, it did. I always took roles that were high commission and low base because I knew I could bet on myself. That was one thing I was always really good at. In roles that were direct sales, like when I was working at Bath and Body Works for five and a half dollars an hour, I was really good at hitting sales goals. I was always good at sales and influencing people, maybe because I'm the oldest of five. I wasn't worried about roles with a lower salary. What I was worried about was making sure my daughter was taken care of and that we had medical benefits in case something happened. Thank God I thought about that because, as you know, my daughter was diagnosed with diabetes while I was at the Shipyard. If I had taken that role without benefits and that happened, it would have been life-changing in a bad way for us. So it was a really good decision for me to prioritize benefits moving forward.

Callan Harrington 07:13

Let's talk about that a little bit. Already, it was tough—single mom going into a startup company, a brand new role, and a company that just got benefits. To put that in perspective, about how early stage was it?

Jen Lyttle 07:30

It was very early stage, and I'd never been a BDR before. All the sales I'd done up until that point had been in person. I was really good at reading body language and selling face-to-face, so picking up the phone and calling someone who had no idea who I was to sell something was terrifying because I didn't know how good I'd be at it.

Callan Harrington 07:55

What was that transition like?

Jen Lyttle 07:56

It was hard because, for the first couple of months, I wasn't earning a lot of commission. We were figuring out how to reach out to allied agents, what our product offering was, and what we were selling to them. We were figuring out packages and different things, so not a lot of commission upfront. I remember I started in the fall—I can't remember the exact month—but by January, something had clicked. I got my first $1,000 commission check, which I had never gotten before, and I cried. I remember sitting in my car, seeing my direct deposit, and thinking, "Holy shit, this is working."

Callan Harrington 08:38

Why was that so important to you?

Jen Lyttle 08:41

Because at the time, my bank account was negative. I knew how to manage my finances so that I could avoid late fees, but it was a struggle. We were ordering Little Caesars' Hot-N-Ready pizzas constantly. So being able to pay my rent and bills with one check was something I'd never been able to do before, and that was life-changing at that moment.

Callan Harrington 09:12

How did that change your life?

Jen Lyttle 09:15

It motivated me to never be in that position again. I never wanted to wonder how my rent was going to get paid. I'm very stubborn—I remember my dad always offered to help, but I always said no because I wanted to feel that pain of not making it every month. It gave me a perspective that not a lot of people have. I'm also not a college graduate, so I had to fight harder to get ahead. Once I figured out that this inside sales thing could really work and I could make money doing it, I went heads down and kept grinding. My daughter was four or five at the time, and we were kind of growing up together and figuring it out. It's a core memory for me, sitting in my car, looking at that direct deposit, and thinking, "Holy shit, this is it."

Callan Harrington 10:16

That's such a good story. So for you, it was about taking a risk but making sure you had the safety net of benefits. You were protecting against the catastrophic but betting on yourself to figure it out.

Jen Lyttle 10:44

Exactly. And I'm so glad I thought that way. I could have taken riskier moves, but I was thinking about being an entrepreneur before it was even cool. But benefits were a non-negotiable for me because I didn't know where my next paycheck would come from. Knowing I had a consistent paycheck, medical benefits, and enough money to support a roof over our heads and food on the table, even if it wasn't the most nutritious, was crucial until we hit that point of smooth sailing.

Callan Harrington 11:26

So during this time, you're gaining a lot of steam, confidence, and then your daughter was diagnosed with diabetes, correct?

Jen Lyttle 11:39

Yes, around the time you had come on board as the Sales Lead at Shipyard. Our team was really solid, and we were developing strong relationships. We were humming in a sales environment with SDRs and AEs. I had kicked over to the AE role but found I was better at being an SDR, so I went back to that role and was making good money. Everything seemed to be going right—I loved coming to work, I was making great money, and I knew I was getting $100 for every deal I scheduled. But in the spring of 2016, my daughter and I took a trip to New York for her birthday. She wasn't herself—fatigued, laggy, not bouncing around like she usually did. I knew something wasn't right, so we went to the doctor on March 16th, and they immediately checked her blood sugar. It was in the 800s, and at the time, I had no clue what that meant. I knew my grandfather had type 2 diabetes, but I didn't really understand what it was. It turned out to be a genetic disorder, and the only thing keeping her alive is insulin. We had to take a two-week hiatus from life to learn how to administer insulin, check blood sugars, and manage her diet. I was out of work for two weeks, and she was out of school because we had to train the school to take care of her. That's another core memory for me—coming to you and saying, "Callan, I really need to take this time." You and the team sent a life-size doll of Anna from Frozen, which terrified me, but it was so thoughtful. That time was bad—learning your child has a medical handicap—but having a team that rallied around me was amazing. My daughter is a rock star. She'll be 14 this month, and she's one of the most amazing people I've ever met.

Callan Harrington 14:50

That's an unbelievable story. How did you move forward from that?

Jen Lyttle 14:58

It humbled us and put us in a mindset of prioritizing our health. We all get into the mindset of go, go, go, especially in a startup environment, but this allowed us to step back and focus on mental and physical health. That's something I've kept with me and something I emphasize with my sales teams. I make sure they take time off and keep their health in check. If I wasn't already working hard before that happened, it kicked something into me to be successful enough to support my daughter financially and make sure she never has to worry about her health again.

Callan Harrington 16:15

From a career perspective, where did you go on from there?

Jen Lyttle 16:19

Leaving the Shipyard was one of the hardest decisions I made. I actually left for a side job for a bit and then came back because I missed it so much. But I eventually moved on to be a consultant with 10TV and The Fan here in Columbus. I knew one of the marketing directors there, and someone from the Shipyard moved over to 10TV and mentioned they had a consultant role that would be interesting for me. I took the role, even though it was a pay cut initially, because I knew I could make up for it in commission. Within the first year, I landed a $1.5 million account, one of the largest they had ever seen. It was an account that was already spending millions on TV ads but hadn't spent much on digital marketing with us or radio. I was able to get in front of their marketing director and sell an entire strategy, which landed the account. My earnings kept growing, and I stayed at 10TV and The Fan for about a year and a half. But the company was on its way to being sold, and I wanted to bow out gracefully before the sale happened. As soon as I knew that decision was coming, the opportunity at Beam Dental came into my lap.

Callan Harrington 18:21

I want to circle back to something you mentioned—cold calling. It's one of the most challenging aspects of sales. What's your mindset when you go into cold calling?

Jen Lyttle 18:47

I do love cold calling, and I think I'm one of very few who do. Most people admit that prospecting is the worst part of their job, but it's my favorite. I think it's because I'm really good at understanding a need right away. I do a lot of listening. A lot of cold callers now try to get off the phone as quickly as possible and schedule a meeting, but I always found my best prospecting calls lasted 15 to 30 minutes. I like to ask a lot of questions and understand the need. People like to talk about themselves, so it's easy to get someone on the phone, have them talk about what they're doing and their pain points, and then you have them. I love training on cold calling because you can see the results quickly. You give a salesperson a talk track, they go to the phone, and it changes instantly. That magic is something you don't see in the rest of the pipeline or funnel as quickly as you do in cold calling.

Callan Harrington 20:38

I agree. The only thing I've seen with a faster feedback loop than making a change in cold calling is stand-up comedy. Either they're laughing, or they are not.

Jen Lyttle 20:58

Totally. And in-person sales is similar. You can instantly tell if you're hitting with them or not. I've had some pretty embarrassing stories of selling in person—people walking away or slamming a door in my face—but it's easy to tell if you're doing well.

Callan Harrington 21:29

Getting back to Beam Dental, this was your first leadership role, correct? What was that transition like?

Jen Lyttle 21:40

I wouldn't say I directly managed, but I "quote-unquote" managed a smaller team at The Fan and 10TV because I had account managers and a sales ops person working with me. I wasn't their direct manager, but I was playing chess a bit. I wanted to try people management because I was always good at getting people to align on common goals and work together. I figured it would be a natural fit for me. I organically got into the role—I don't think I've ever applied for a role that I ended up getting. It somehow came to me through a network. Beam Dental was another funny one, similar to the Shipyard. I met Chris Procheck, who we both know and adore. I met him at their office in the Industrious building before they were even a carrier. They were getting their Bluetooth toothbrush off the ground and selling it to insurance agents, brokers, and carriers to offer discounts on renewals. We talked a bit about the role, and I did a project day where I prioritized their client base. I was really excited because I thought I killed it, but they didn't have benefits at the time. Procheck told me they were on the verge of their Series B and would have a big runway to offer benefits and grow quickly. Six months went by, and he finally reached out and said they had benefits, changed their business model, and landed their Series B. They were hiring and scaling their sales team significantly, and he asked if I'd be interested in leading some of those teams. It was a hell yes for me at that point.

Callan Harrington 23:50

What was that transition like for you?

Jen Lyttle 23:52

It was hard.

Callan Harrington 23:53

How come?

Jen Lyttle 23:54

I had never been at a venture-backed company before. I had been at private equity and privately-owned companies, but never a company solely dependent on venture capital. I didn't even know what a Series B meant. I remember Googling venture capital and what it meant before accepting the role. I had no clue. I had a crash course with Procheck and a few others and understood that the capital we were gaining had to be spent quickly, and we had to show growth year over year fast. They hired me as one of the first sales directors, along with Steve Ruder, who we both know. We came on board with about four salespeople, and the company had less than 50 people—probably around 40 or under. In my first year, from May to December of 2019, we went from four salespeople to 75. We still hit our revenue goal that year, closing our first $10 million. Then the pandemic hit in 2020, which is a whole other conversation. But that was the fastest-moving role I've ever been in, and I learned the most in that six to eight months than I have in any other role.

Callan Harrington 25:47

You grew that fast, and then the pandemic hit. What challenges did that cause?

Jen Lyttle 25:54

Man, so I was managing the BDR team at that point, which I loved because I loved being a BDR. I got on the phones a lot with my team, and we were cold-calling back and forth. That team is still very close to this day.

Callan Harrington 26:11

You said you were jumping on the phones as well. Why was that important to you?

Jen Lyttle 26:16

I've had a lot of managers who delegate and sit on an ivory tower, looking down and delegating responsibilities. But I've always found that the leaders who get in the weeds with the team and are player-coaches are the most successful. It doesn't matter if my team is one or 20; I'm going to do the work with them and show them I'm still capable. A lot of sales leaders don't know how to cold call, close a deal, or create an opportunity in their CRM, and that's a big problem. You see leadership teams struggle because they're not able to get in and see what their teams are doing. That was really important to me—to do the work with them and show them that I could still beat them at it. I had a rep who was better than me at cold calling, and it always ate at me a bit, but I loved it. I wanted to challenge everyone to be better and keep that team camaraderie going.

Callan Harrington 27:40

You ultimately moved on from Beam Dental. What led to that decision? What was the driving factor for you?

Jen Lyttle 27:55

At the time, my partner Jared, who I met at the Shipyard, and I got pregnant with our son during the pandemic. We both went on maternity leave for 12 weeks, and Beam has wonderful benefits. During that time, there was a transition happening at Beam where the BDRs shifted out and became more like associate account executives, focusing on not just prospecting but getting deals through the funnel. I offloaded my team, and they all got promoted. I took on more of a communication, strategic sales enablement role, working with tools like Salesforce, SalesLoft, and ZoomInfo. But there was friction between sales, marketing, and operations. Jared was the Salesforce admin at the time, and we were having these conversations at home about the challenges. I started realizing that I wanted to try an operations-style role—something that would allow me to lead a sales organization and think about revenue from a high-level perspective. During my leave, I wasn't looking for new roles but was open to the idea. Then I met Matthew Verizer, who you just had on the podcast, and he presented an opportunity at Ascend Innovations in Dayton that I couldn't turn down. So I left Beam on great terms, and Jared is still there as their Salesforce operations administrator. I still feel like a part of that team, but the opportunity at Ascend was too good to pass up.

Callan Harrington 31:02

It's interesting how you figured out what you wanted to do while at the job, not after taking the next job. I’ve been more opportunistic, and it wasn’t until I left to start my own company that I made a decision for me. Otherwise, I just took the next good opportunity. I love that you knew what you wanted and identified the things you liked to do and what would help you progress into more of an executive role.

Jen Lyttle 32:03

Yeah, I always joke that I take on roles I’m not super ready for, which helps me learn quickly and on my feet. I can identify process friction points and when a sales process isn’t flowing well. A lot of sales leaders are just sales leaders, but I have more of a revenue mindset. I like to manage teams that include sales, operations, and account management and see how they all work together. So, yes, I identify what my next role should look like and seek out roles that will allow me to start doing those things instantly and learn as I go.

Callan Harrington 33:01

It also gives you an opportunity to try it out and see if you even like doing it, right? So you moved on to the next company. What did you want to get out of that role?

Jen Lyttle 33:12

Ascend Innovations is a data science technology consulting firm in Dayton, Ohio. Beam had gotten to the point where it had over 300 employees, which was insane. We all didn’t fit on the floor of the office anymore. I wanted to go back to a building role that would allow me to start from scratch with a company that didn’t have anything figured out yet from a revenue perspective. At Beam, we had built and built and built, and by that point, the wheels were running. There were still things to fine-tune, but they were humming. I felt it was time for me to move on, and I wanted to work with a smaller company to build revenue processes again. Verizon came to me and said they needed someone in a revenue headspace to help with their go-to-market plan, internal technology, product-market fit, and sales strategy. The deal breaker for me was that they were serving a community and working with public health departments and recovery boards in Ohio. My sister is in recovery, and I’ve been through that process as a family member of someone in active addiction. Even though it wasn’t a frontline role, we were doing things on the back end to provide data to government entities to make better decisions. That was a fantastic opportunity for me, and the company had about 20 to 25 people, which was a great size for building.

Callan Harrington 35:06

What was it like working for a mission-driven company?

Jen Lyttle 35:09

It changed my entire mindset about my career. I had come from fast-moving industries like InsurTech and digital marketing, but Ascend was different. It was more about serving a community and doing well while doing good. After my time at Ascend, I had some time off to reflect. I had great interviews with fast-growing InsurTech companies, but I turned those down because I wanted to go back to a company with a mission I could believe in. It was important to me to work for a company that my daughter and kids would think was cool, and now my daughter brags about what I do. So it was important to me to stay in a mission-driven organization, no matter the size.

Callan Harrington 36:19

So, if I'm hearing you correctly, it's about wanting a personal connection to the work you're doing. Insurance is great, but you wanted something that resonated more with your personal experiences. Is that right?

Jen Lyttle 36:47

That's right. Even when I was consulting with you at FlashGrowth, I loved the work, but I realized I wanted to build something and see the impact later on. Insurance was great for building my career, but I wanted to continue doing work that I could see the impact of. And that's what Aunt Flow offers. Yes, we're a revenue organization and a venture-backed company, but the mission and the people here are driven by a true belief that menstruating humans across the world should have access to free period products. That's really important to me and what gets me up in the morning.

Callan Harrington 37:46

If you could have a conversation with your younger self, at any age, what would that conversation be? What advice would you give?

Jen Lyttle 37:56

I've thought about this because I’ve listened to all your episodes, but now on the spot, it’s a little different. My 20s were really hard—I had my daughter at 22, was a single mom, and took jobs just for the paycheck. But looking back, I wouldn’t change anything. I would tell myself that the hard work is going to pay off. It’s coming, just keep going, don’t give up, keep your head down, work hard, and work harder than anyone around you. That’s my biggest thing—I want to work harder than everyone around me, but also be the one in the room who doesn’t know everything.

Callan Harrington 38:57

I love it. Jen, this has been incredible to hear your full story. Thanks for coming on the show.

Jen Lyttle 39:03

Yeah, I've had a great time. This was fantastic. I was looking forward to it, and I'm excited to see your other episodes too.