Welcome to the Brave Women at Work podcast. This is your host, Jen Pestikas. I’m so glad you’re here. Well, hello everyone. How are you doing out there? I’m gonna ask for your grace and compassion over the next few weeks as I recover from just an epic nasty sinus and ear infection. I sound dramatic, but I promise you getting an ear infection as an adult is serious business. You’re gonna hear my voice, it’s a little raspy. I’m a little off my game on various levels over the next few weeks, but I wanted to make sure to share all of these guests. I have all these guests scheduled and I wanted to share these awesome interviews with you. So I am asking for your grace and compassion in advance.

Today I am interviewing someone that I look up to tremendously in business, Kym Insana. As you will hear, Kym not only is a wife and mom to four boys, I’m like, what? Wow, I know, four boys, but she has also built a very successful marketing and media execution business. Kym’s mantra is you can work hard, have career success, and the family life you desire. As soon as I heard that, I was like, tell me more, Kym, tell me more. Who doesn’t want to have career success and personal lives we desire?

During today’s podcast, Kym and I chatted about why Kym decided to build her multimillion-dollar business, Always On Digital, why Kym is so passionate about working parents and how she helps her own employees that are working parents with their values and their policies within her own company. Kym’s advice for women who want a high-powered career and life, she believes that it is possible. How Kym manages her teams, both in person and remote. Digital marketing and media, we touched on it of course. I had to talk about this since I am also a marketing nerd. So just bear with me as I go into that part of the conversation because I’m like, yes Kym, yes I wanna hear more. Hopefully you find it interesting as well. And just so much more. Kym was a joy to have on the show.

So here’s a little bit more about Kym. Kym Insana is a multimillion-dollar business owner, digital marketing expert, wife and mother of four boys. As the founder of Always On Digital, she helps leading brands reach the masses through dynamic digital campaigns that generate consumer interaction and sales so they can scale. Top brands lean on Kym’s expertise, including the U.S. Air Force, American Enfamil, the Texas Rangers, and Johnston & Murphy.

Kym jumped into the digital marketing world before it became part of the modern fabric for business growth. For more than 20 years, she’s led sales and digital campaigns for top advertising agencies in New York City. But dealing with a two-hour commute while growing her family proved to be a turning point. She felt compelled to start a business and gain her time back. The yearning for freedom quickly outweighed the desire for a corporate career. At the same time, Kym noticed other successful women quitting the workforce for similar reasons. That prompted her to ask herself, what if I could build a business that fit these talented women and their ideal work schedules while still providing them with a career? In 2016, Always On Digital was born.

Today it’s a multimillion-dollar company that proudly offers creative and flexible work schedules for employees who are made up mostly of super motivated mothers, often former executives who desire income and increased work-life balance. As I said earlier, Kym’s mantra is you can work hard, have career success, and the family life you desire. She has shared her story and expertise on stages across the country, including The Big in San Francisco and iMedia Brand Summit. Always On Digital is certified as a women-owned small business through WBENC.

So if the Brave Women at Work podcast has helped you both personally or professionally, I’ll ask every week, just share it with a friend, a family member, or a colleague. And of course, your ratings and reviews help the show get in the hands of more women. It’s amazing, sometimes I love a show and maybe a different show hits differently. But then someone will contact me and be like, I love that particular show. So you never know. All the different topics, and the show ranges a wide gamut of topics. Everyone takes the shows differently, everyone gets inspired by different topics. So if you’re inspired, please do me a favor and share the show.

Also, if you haven’t yet joined, and I haven’t shared this in a long time, there is a private podcast Facebook community. If you’d like to be on the inside, join us over there. Simply search for Brave Women at Work Podcast on Facebook and I will let you in. I’m planning to share special news and updates within that group, so just join us over there. I’d love to see it continue to grow.

We also have, and this is super fun, I am on with my business partner and dear friend, Hope Mueller. We are on our fifth book in the Brave Women at Work anthology series, and we have one to two author spots still available. The upcoming book title is Brave Women at Work: Lessons in Authenticity. If you have a dream of becoming a published author, look no further.

Hope of Hunter Street Press, she’s the founder and CEO, and I take you step by step through the entire publication and book marketing process. It’s about nine to 12 months long. And the best part, you do not need to be a professional writer. You do not need to have an English major, I promise you. You simply need to have a dream of becoming an author and a story of authenticity within your heart. If you would like to learn more, email me at hello@bravewomenatwork.com

I am happy to jump on a one-on-one call with you to explain the process, the investment, and what you’ll get out of it to see if this is a fit for you.

Okay. Let’s welcome Kym to the show.

Hello Kym. Welcome to Brave Women at Work. How are you today?

I’m great. How are you doing?

I am so, so good. Thank you so much for being here.

Thank you for having me. I really appreciate it.

Yeah, of course. Why don’t we jump right in. My longtime listeners and even my newbies know that I love women’s stories. It’s one of the reasons I get so much joy and pleasure from doing this show. So tell us a little bit about you and how you’ve gotten to where you are.

I am a mom of four boys. I have children that range from eight to 18, so a little bit of a wide spread there.

Wow, okay.

I left corporate to start my own business basically without any knowledge of starting a business or if I should be doing it at all, and just kind of jumped right in. Share on X

Very involved in sports, so I’m a big sports mom. And the second part of me is I left corporate to start my own business basically without any knowledge of starting a business or if I should be doing it at all, and just kind of jumped right in. We have an advertising and marketing business that helps agencies and advertisers run media campaigns.

That’s pretty fascinating. Were you in marketing before, or why did you decide to go and start your company, AlwaysOn Digital? What’s the story behind that?

I actually went to high school in New York City and I got an afterschool job at a radio rep firm in the nineties. It wasn’t that I necessarily thought my path would be advertising, it just was where I was placed. A friend told me they were looking for part-time folks, I started there and I worked my way through college.

My big dream was actually to be a sportscaster for basketball or something like that. At the time it was all about Marv Albert and the Knicks. I thought that would be my path, so radio seemed like a good fit. But my boss was leaving to start this new internet company, similar to radio, like a rep firm for websites. I joined in around the end of 1999, 2000. I ended up staying in digital advertising from then on. It wasn’t necessarily a passion, but I liked it. I liked the people, and I stuck with it.

I have to ask because I’m going through this right now, and there are probably a lot of women that have side hustles or big dreams. What was it in you that said, I’m gonna leave corporate? What’s the story there?

Honestly, going back to the radio days, we all have something in the back of our mind that nags at us. I was only 16 when I started in radio, but there were these women that worked there as sales reps. They did part-time job shares. I was fascinated by it because they were so good at their job. They were outselling a lot of people, they had their stuff together, and I was impressed. They were mothers, they took care of each other’s kids on different days, they each worked three days a week.

This was before cell phones and laptops. I thought that model should apply to every mom and be available as a resource because moms get it done. I’m not saying others don’t, but I just felt like they always did.

So as I was going through my career and started to have children, I kept asking for this. I’d say, can I work from home? One of my jobs was fully remote.

Okay, that’s good.

This was the early 2000s. They were a California-based company. I was able to work from home. When I went back to more of a corporate role, I said, I’ve proven myself in these situations, why can’t I do it? The answer was, that’s not the way it is.

It became frustrating over time as my life got more complicated, trying to get the kids to before care and aftercare, having babysitters, traveling. I thought, why do I even have kids if I don’t see them? I was starting to break. I noticed other women leaving the workplace or taking steps back. It felt unfair that if you want kids, you don’t get to have both.

Our CEO was kind in helping people start their own businesses. I went to him and said, you help all these people, but a bunch of us don’t fit here. Business models were changing and I didn’t agree with the way customer service was happening. I thought it should be a certain way. I asked him to give me his blessing to take these people that didn’t fit here. I said, I’m gonna hire some people and maybe we can partner on stuff that doesn’t make sense for you.

That was my initial hook with them. They helped me get started. Little did I know, I didn’t really need them. I could have started an LLC on my own. They set it up and then basically said, see ya. Which was good for me personally. That ended up being my breaking point.

Some of the best employees and team members I’ve worked with were in a similar boat. They were passionate about doing a good job while also being there for their family. It doesn’t have to be complicated. Share on X

Wow. So is that why in your company, at AlwaysOn Digital, you have that mission of supporting working parents? Is that why it’s so important to you?

Yes, exactly. Some of the best employees and team members I’ve worked with were in a similar boat. They were passionate about doing a good job while also being there for their family. It doesn’t have to be complicated. I want to make sure there is a place for them, as many as I can hire.

That’s great. How big is the company now?

We have 18 folks right now.

Okay.

We’ve been growing steadily. We haven’t taken any outside investment, which was on purpose. I didn’t want to fall into that trap of corporate again. But we made a decision this year to grow differently, still not taking outside investment, but doubling down on the team and sales so we can maybe double by next year.

Oh, that’s amazing. That would be amazing. And you keep growing the team and your mission. You said something that really stuck out to me: the workplace is still broken. What advice would you have for mothers or caregivers who want to balance a big career and a big family life?

Maybe the family life is travel. We’ve hired people without kids who were passionate about being somewhere else. To your point, our job is not our life. Our life is our life and how we want to live it.

The advice I have came from Tim Ferriss’s The 4-Hour Work Week. Just ask. The worst they could say is no. Or maybe they’ll try a different scenario. After COVID, more flexible options appeared, but now there’s a shift back to offices. There has to be a hybrid somewhere.

It’s not one size fits all. I think managers should lead to the individual, not the team. Everybody has individual needs, and they should be managed as such. It doesn’t have to be, well because he got it or she got it, I have to get it. Some of it is earned. Go to the table with ideas, show your track record, reduce the risk for them.

Sometimes the answer will be no. That doesn’t mean it’s no forever. Maybe it’s no right now. Or maybe it’s no forever, and then it’s not the right situation for you.

Right, which you did. If you don’t ask the question, the answer will always be no. But if you ask and it’s a no, you still get information about your environment, your manager, and yourself.

I agree 100 percent. Sometimes they wanted you to ask so they could see your drive. I had a boss that didn’t give raises unless you asked.

Wow.

He thought, if you can’t ask me, how are you going to ask a client? Whether or not I agreed, I understood what he was trying to do.

I say this when I have a negotiation freebie. It’s knowing how far you can push with who you report to, when to step off the pedal, when to push, or when to reapproach.

Absolutely. Doing the heavy lifting helps too. When you ask for something, make it easy for them to say yes. Show your track record, ask for a trial period, agree to regular check-ins.

I once had a manager obsessed with my IM status being idle. They assumed I wasn’t working. But sometimes you want to take a call while walking around the block. It doesn’t mean you’re not working, it just means you’re not sitting. Knowing your manager’s fears helps so you can set them aside.

Yes. And I struggle with that too. Are you a manager or a leader? Leaders trust. If trust is broken, it’s different. But constant monitoring shows a lack of trust.

Exactly. If I was on a performance plan, fine. Otherwise, let me work.

You said you manage to the individual. What about big corporations with HR policies and fairness issues?

The larger the organization, the harder it is. At one point I was getting some work-from-home flexibility, others weren’t. For sales it was easier because we had metrics.

But brushstroke policies like “nobody can work from home” are ridiculous. I had team members with very different needs. One didn’t want a 100 dollar bonus, they just wanted to leave early to make a train. I pushed back on those situations. It was a tradeoff. It wasn’t unfair, it was just different.

Yes, I like that. It’s about tradeoffs. Some people care about perks like food or foosball tables, but others just want to leave early.

Exactly. I saw this at a company acquisition. They brought in massages and a ping pong table. But salespeople weren’t even in the office to benefit. Parents didn’t care about ping pong, they wanted to finish work and go home. Culture perks don’t fit everyone, and what’s called “fair” can actually be unfair.

Totally. And smokers get smoke breaks, but nonsmokers don’t get breaks. Life isn’t fair. We need to understand what motivates people.

Yes. When I was pumping at work, people thought that was an unfair break. Meanwhile, I had my laptop and was still working. The audacity.

I think I understand why you left.

Exactly.

So with four boys, how do you find balance?

I agree balance is a weird term. It’s more like a seesaw. I try to just get through each day. People ask, how do you have four kids? I say, you deal with it. You accept it and move forward.

There’s always a lot of balls in the air. Some are glass, some are plastic. You just need to know which is which. Sometimes you can drop a plastic ball at work and it’s fine. But don’t drop the glass ones.

I thought working from home and starting a company meant I’d bake for the kids and not go to bed at midnight. That’s a joke. I’m still at the supermarket at 11 pm. Laundry’s worse. It’s about giving yourself grace. You can’t be perfect.

And with older kids, the clock is ticking. There are only so many years left. It’s sad, but it makes you focus on them. Work is important, but family time is fleeting.

There’s always a lot of balls in the air. Some are glass, some are plastic. You just need to know which is which. Sometimes you can drop a plastic ball at work and it’s fine. But don’t drop the glass ones. Share on X

Yes. There’s a book called Drop the Ball by Tiffany Dufu that talks about this. And I try to “be where my feet are planted.” When I’m with my kids, I try to really be there.

Exactly. Sometimes it’s just carpool. My kids tell me everything in the car. That’s quality time too. At night we rotate activities, movies, puzzles, even blackjack.

We do that too. My daughter even got in trouble at daycare for gambling because my husband loves Vegas.

That’s hilarious.

Let’s pivot again. What advice would you give to women who want to start their own business?

I went headfirst because of a layoff. Fear is always there, should I commit or go back to corporate? My advice: research a little first. I didn’t go to business school. I don’t have a business degree. The most important piece I was missing was accounting. It’s critical.

My son is studying finance because I drilled into him how important numbers are. That’s the piece I wish I had learned more of.

Also, there are so many resources now. Business plans, tools, local organizations, women-owned business groups, you’re not alone. I didn’t know about these for my first couple years. Tap into them. Start slow. Adjust expectations. Sometimes you don’t need the same money you made in corporate. Costs change. You keep 100 percent of what you make.

Yes. And remember it took years to reach your corporate level. You can’t expect the same success overnight.

Exactly. Even now, nine years in, I wouldn’t say I’m at the same level I was in corporate. It takes time. Referrals have been our best friend. We had early curiosity, but keeping momentum is hard. You need motivation to keep going.

The first couple years, it always felt like the bottom could fall out. One lost client could sink you. Now we’re more stable, but it took three years before I felt the business had legs.

How did you manage the fear in those early years?

I remembered why I left. I was seeing my kids in daylight. Did I really want to give that up? Staying in touch with corporate colleagues helped too, I heard their horror stories. I didn’t want that life back.

It kept me going. I also thought about legacy. Maybe my kids will take over one day. I want to build something for them. That became my goal.

That’s so cool. And your kids are proud of you.

Yes, even if they mock us sometimes.

Let’s talk marketing. How do you decide what platforms to use for clients?

It depends on the brand. Not every brand belongs on TikTok or Snapchat. Facebook skews older. Instagram, search, Reddit, it depends on the demographic and goals.

Most mid-sized companies have three or four core platforms they should focus on. From there, test and learn.

Some people think they need to be everywhere. Do you agree?

No. If you’re McDonald’s, sure. But smaller companies should focus. Diluting budget and energy across too many platforms doesn’t work.

Algorithms are tricky. Is it harder now to get noticed?

Organically, yes. Paid depends on budget. Algorithms and AI are there to make money for the platforms, not necessarily for advertisers.

AI is everywhere now. It can even create ads for you without your input. That’s scary, because you don’t always control what goes out under your brand.

That is scary. And what about AI for personal branding?

AI has its place. But don’t lose your authenticity. People can tell when it’s not you. My son used AI for a paper and got caught. It wasn’t his writing.

Use AI as a tool, but don’t outsource your voice. When it comes time to do the work, clients expect you, not AI.

I agree. Boundaries are key.

Yes.

What are one or two ways women can be braver at work today?

Ask for what you want, especially if it’s reasonable. Stop doubting yourself. We judge ourselves more harshly than anyone else does. Speak up. Bring your ideas. Don’t let imposter syndrome silence you. Do the work, build trust, and find your allies.

Thank you so much. Where can women find you and Always On Digital?

I’m on LinkedIn, Kym Insana. Our website is getawayson.com. My email is kym@getawayson.com

Thank you so much for being here. We covered a lot today. Things are like Marie Forleo, I think she’s a New Yorker too. It’s, what is her book? Everything is Figureoutable, right? You went from corporate to running a multimillion-dollar business and being a mom of four. It’s inspiring to see.

Thank you so much for having me. I appreciate it.

That’s a wrap on my discussion with Kym today. I hope you found our conversation valuable and inspiring.

As a reminder, please rate, review, and subscribe to the podcast in Apple Podcasts and Spotify. The show is also available on any other podcast platform you enjoy.

Until next time, show up toward your own path and be brave.