Alyssa Kropp's Journey to Founding a Firm That Grows Leaders and Revenue

Please share a brief introduction about yourself and your business:

Hi, I’m Alyssa Kropp. Coming from a typical type A over-preparer, it takes a lot for me to be caught off guard. But that’s exactly what happened in August, 2022 when, 11 weeks into a 12 week maternity leave, I was laid off from my senior sales leadership position at a unicorn tech company. I had been in sales and sales leadership for 15+ years and looked at the layoff as an opportunity to pursue a dream of launching my own business, The Casslo Group. Through my work, I'm able to help growth stage tech CEOs move from founder-led sales to an over-performing revenue engine. When I'm not setting up sales teams, I love being a mom to my 2 favorite humans, attempting to try every coffee shop in Omaha and traveling back to the east coast to visit family and friends.

Who are your customers?

Growth stage founders who are overwhelmed by founder-led sales but don't know how to transition to hiring a sales team (much less, make them successful).

What was your background prior to starting your own business?

I'd been in sales my entire professional life working as an individual contributor and leader of sales teams. I joke that I've sold anything and everything, from commercials on Comedy Central to wedding advertising to advocacy software. You name it, I can sell it.

What made you take the leap to start your own business?

I was laid off 11 weeks into a 12 week maternity leave so the choice was semi made for me. I look at the lay off as one of the biggest blessings of my life because I don't think I would have ever made the jump from corporate on my own. Being let go was exactly the push I needed to pursue this dream.

Did you always know you wanted to be an entrepreneur?

No! In fact, growing up, I saw my dad as an entrepreneur and it always looked stressful. I thought it would be a much easier road to just work at a traditional job. And I was right, the road is probably easier but this work as an entrepreneur is much more fulfilling.

Take us back to when you first launched your business; what was your marketing strategy to get the word out and did it go as planned?

My marketing strategy has, and maybe continues to be, not strategic at all. I've built the business on connecting with others and unabashedly telling everyone what I'm working on.

What is the biggest challenge you have encountered along the way so far and what have you learned from it?

Loneliness & motivation. Once the cheering and enthusiasm of the initial launch of your business dies down, it gets real quiet as a soloprenuer. Finding the drive every day to motivate yourself (especially on things that you're not particularly skilled at or have to learn), has been a challenge I didn't anticipate. From this, I've learned that I don't need to be working every single hour to be successful and that I'm much more resilient than I ever thought possible.

What accomplishment are the most proud of to date in your business?

I'm most proud that in the first 2 years of my business, I've brought in over $100,000 in annual revenue, a milestone achieved by only 5% of female owned businesses.

Do you have any recent wins from the last year that you'd like to celebrate with our community?

I launched a local meetup here in Omaha that focuses on empowering the next generation of leaders. So often, individual contributors are promoted up to management with little tools, resources or support. At Rising Omaha, we bring in local leaders to speak on how they've approached some of the most common challenges in leading others.

What's next for your business? What can we expect to see over the next few years?

I'm growing The Casslo Group to be a million dollar company. Only 2% of female owned companies achieve this milestone and I've never been one to back down from a challenge. We are going to continue to hit our ambitious revenue targets while still keeping the heart of The Casslo Group which is to prioritize people for who they are before we consider what they can deliver for us.

What is your top productivity tip? 

Block your calendar by category to avoid context switching. So for example, I try to do most of my coaching in the mornings, mid afternoon is client work with my clients and then afternoons for me are spent working on my business (social posts, newsletters, proposals, etc).

On the flip side, how do you avoid burnout?

I assign myself the must do tasks of the day and try to limit it to 3. Once those are completed, I can choose to keep working or take a break for rest, exercise, a long lunch, etc. This maintains my energy and excitement around the work and helps me break down my previously held beliefs that in order to be successful, I need to be working 40+ hours a week.

What is your approach to work-life balance / integration?

I've actively tried to redefine success for myself. In my corporate roles, I believed success was my title and salary and chased them at all costs. Now I try to consider that success in my life is taking my girls to school, it's exercising every day, it's making lunch instead of ordering out, it's spending time watching Love is Blind with my husband instead of working at night. Viewing those things as me being successful has allowed me to prioritize them.

What is one thing you wish you had known when you started your Entreprenista journey?

Get someone to handle your taxes. I made a lot of early mistakes with taxes that could have easily been avoided.

When hiring, what is your go-to interview question?

What's one thing I didn't ask you that you hoped I would?

Are you a Mamaprenista? If so, please share your best advice for simultaneously managing a business and a family:

My girls are watching. I tell this to myself a lot because it reminds me of the example I want to set for them. I want them to push through when times get tough, to problem solve with out of the box ideas, to have a strong work ethic but to not lose themselves in the process.

What's the one app on your phone you absolutely cannot live without and why?

The YouVersion Bible app. It grounds me and reminds me that I am on a predestined path that was laid out for my life long ago.

What is your favorite business tool or solution and why?

ChatGPT.  Hours of time savings. If you're afraid of AI or don't know how to use it, reach out to me. It can be your most powerful tool in business.

What advice do you have for aspiring Entreprenistas?

Don't give up because it's hard. It's not a matter of if it gets hard, it's a matter of when it gets hard. And when it does, the majority of people will give up. You're not the majority of people. There's a reason you started this business and a vision you have for it that the world needs to see. You can give yourself permission to give up for a multitude of other reasons (it doesn't serve you, it's not financially the right move, etc) but just because it's hard? As Glennon Doyle would say, "we can do hard things".

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