Rewind to my college days, when picking accounting as a major was pretty much a no-brainer.

Accounting was easy for me. I’d been doing bookkeeping since high school, and it ticked all the right boxes for making my mom proud with a degree in hand.

However, as I transitioned from the nuts and bolts of accounting to the broader horizons of an MBA, I felt a change in the air.

It was like the universe hinting that I was about to take a detour from the beaten path.

The tech world beckons

Jumping into the tech world wasn’t exactly on my bingo card.

Despite the well-meaning warnings from my manager, co-workers and mom, I left the safety net of my accounting job on a big team at a multi-level marketing company for a role in a tech startup. This was right at the dawn of the e-learning era when we were still mailing out video tutorials on DVDs because the internet was dragging its feet.

This seemingly small job switch changed my life forever. Suddenly, I was in a world brimming with jobs I didn’t even know existed. I worked for a CEO who let me explore different sides of the business, including eBay, affiliate marketing and the mysteries of SEO. I was hooked! I quit my job and started building websites and doing web marketing.

Fast forward three years. My internet sites hit a plateau, and I was failing at a commission-only sales job.

Then came the wildcard: “Could you build us a hiring software platform?”

Me? A non-coder with no HR background and zero experience with hiring platforms? Challenge accepted!

And so it began — just me and Heather Wells, a part-time programmer, with my tech buddy Trent Staheli on speed dial.

“The internet brings overnight success!”

Let’s get one thing straight: the tech world’s favorite fairy tale — the overnight success story — is more myth than reality. The early days at ApplicantPro were a masterclass in dodging curveballs.

Our rallying cry, “The Obstacle is the Way,” wasn’t just a mantra. It was our playbook. But it paid off — with eleven years in a row on the Inc. 5000 list.

No, really. Less than 100 companies have done that, ever.

So, let’s dig into how we did it.

And built an HR software platform that shattered conventional norms and landed on the Inc. 5000 list eleven years in a row.
The Applicant Pro team. | Photo courtesy of Ryan Kohler

“Internet business is easy!”

Venturing into the SaaS domain in the late 2000s, especially with a focus on HR software for small businesses, was like sailing into a storm. The typical HR buyer was seen as a dinosaur in the tech ecosystem, tight-fisted and tech-shy.

Funding? A desert wasteland. Angel investors just couldn’t wrap their heads around a non-tech founder wading into the HR tech space.

The chorus of advice was pretty clear: targeting HR folks without a war chest and a battle-hardened sales team was madness. These obstacles didn’t just seem big; they looked mountainous.

But for me, that was exactly where the fun began. Proving people wrong was my primary motivation in life!

Luckily, I had a team who didn’t know any better. Off we went to turn these challenges into opportunities, innovating our way through the adversity.

“You need to raise capital to grow!”

Conventional funding routes were a no-go. Banks and VCs were out of reach.

Our solution? Get creative with funding.

We pitched our clients and resellers on the idea of annual prepayments — a bold move that became our lifeline, keeping our dreams afloat during those make-or-break early years.

“HR is not a software buyer!”

Then, there was the myth that HR folks at smaller businesses weren’t software savvy or able to pull the trigger on the buying decision.

We dug deeper and realized that maybe they just didn’t trust the sales reps pitching them on the hype with no way to see it in action.

So we flipped the normal sales approach on its head and introduced free trials and month-to-month contracts, which was practically unheard of at that time in the HR tech space.

It was our “put up or shut up” moment. Either our software performed miracles, or we didn’t deserve to be paid.

And just like that, we went from just another vendor to a trusted partner.

And built an HR software platform that shattered conventional norms and landed on the Inc. 5000 list eleven years in a row.
Photo courtesy of Ryan Kohler

“You need to build a sales team!”

While the rest of the world was still playing the cold call game, we were drawing inspiration from HubSpot and doubling down on inbound marketing.

Educational webinars, tons of voices and a blog full of free advice — offering value upfront — were our magnets, attracting clients with genuine solutions and expertise.

We even played games at trade shows designed to teach our prospects about recruitment marketing in exchange for designer purses. Anything we could do to help our prospects with their hiring, regardless of whether they became our clients.

“You need an experienced team!”

Here’s where we truly broke the mold. Instead of the usual hiring playbook, we promoted our support staff — mostly working moms — into sales roles.

This amazing team, doing demos around carpool and soccer practice, was laughed at by our competition. Little did they know that there is nothing more powerful than an underestimated opponent.

The one group who wasn’t laughing at the idea was our clients. They loved our sales reps and the entire team. Their deep product knowledge and empathy were our secret sauce, enriching our sales approach with authenticity.

Did I mention that I paid for my team’s house cleaning? Let’s do the math: With almost 300 employees x $100 per month, I was basically supporting an entire house cleaning company.

Covering the cleaning bills for my MomForce wasn’t just a nice perk; it became a power play for recruitment and retention.

“Employers aren’t hiring!”

When the pandemic hit, the world paused, but we didn’t.

We focused on a mantra from my mentor: “What would you do if you only got paid if your clients were successful?”

To us, the solution was obvious. We’d break the SaaS rules! We’d go down-market to smaller essential businesses, and we’d bundle powerful services (like writing job ads) with our software.

Basically, we’d take shared ownership of the hiring success of our clients. It fueled our growth through uncertain times by driving up both revenue per client and retention.

“You can’t beat Goliath!”

ApplicantPro’s journey is a testament to the power of the underdog, constant learning and evolution, and being driven by the conviction that every challenge is an opportunity in disguise. It’s about more than just navigating uncharted waters; it’s about embracing the journey, guided by the philosophy that the obstacle is indeed the way.

Today, my amazing team continues on their course. Their mission remains unchanged: to innovate, persevere and keep flipping the script — one challenge at a time. I couldn’t be more proud of the amazing tech powerhouse that the team has become.

“It’s all about the exit!”

No matter how difficult it was to persist in the face of those challenges, the hardest one — by far — was stepping aside and letting my team sail on without me.

Today, you’ll find me working on the other side of the hiring equation: helping job seekers find jobs by sending over a billion emails a year full of free advice and job alerts.

It’s a totally different target with a new set of challenges, but the same mantra guides me: “The Obstacle is the Way!”