Betting on Yourself: Navigating the Leap From Sales Leader to Business Owner
- Robb Conlon
- Mar 17
- 4 min read
In this episode of B2B Business Class, host Robb Conlon sat down with Steve Wallace, President of MaverickApp, to discuss the leap from being an employee to becoming a business owner.
Steve shared his journey from a successful career in sales to leading a company, offering valuable insights on entrepreneurship, sales strategy, and building a business around solving real problems.
The Moment to Bet on Yourself
Steve has always believed in betting on himself, but his career pivot wasn’t a sudden leap — it was a natural progression built on years of experience.
“I've been betting on myself for a very long time. The real question is what was the pivot moment?” Steve opined. “How do you end up going from insurance to [leading] a tech company?”
Having started in insurance sales, he was already operating as an independent professional under the umbrella of larger organizations.
Over time, he realized that his ability to train, motivate, and guide other sales professionals was in high demand.
Steve’s pivotal moment came when sales professionals began asking for his advice on messaging, prospecting, and positioning.
“ There are parallels between what I was doing in insurance and what I'm doing now,” he explained. “ Selling intangible things like results can be difficult for people.”
What started as informal coaching evolved into a structured approach that ultimately led him to MaverickApp.
From Sales Coaching to Sales Automation
At its core, Steve’s transition wasn’t about leaving behind one career for another — it was about recognizing a gap in the market and filling it.
What ultimately drew Steve to MaverickApp was his realization that the challenge many professionals face isn’t just prospecting — it’s maintaining consistent prospecting efforts while juggling other responsibilities.
“As soon as you schedule a meeting with a lead, now you don't have time to prospect because now guess what you have to do? Report to your upline, report projections, manage your follow up, admin — even your business meetings are at odds with your prospecting.”
By automating essential sales prospecting tasks — account research, outreach, and follow-up — professionals can focus on closing deals rather than getting bogged down in administrative work.
”You can focus on high dollar activities, like calling people who have expressed interest,” Steve said.
The Decision to Stay and Lead
Our conversation came back around to the time Steve considered stepping away from his role as Chief Revenue Officer at MaverickApp to pursue his own venture in sales consulting.
“ I started to test the waters and have an impact on people, and they were paying me to do it,” he shared. “I'm like, ‘Wow, there's something to this. I can go create something totally new.’”
Like many budding entrepreneurs, the idea of starting his own business appealed to Steve. However, after discussions with the company’s founder, he saw an opportunity to incorporate his vision into MaverickApp’s evolution rather than building something entirely new.
“ I asked myself, ‘Do I care if it's over here or there?’ No,” he concluded. “Either way, it's my baby. Either way, it's my creation.”
The company’s founder stepped aside, giving Steve the reins as the president of MaverickApp. But Steve noted that rather than a takeover, the transition was a handoff that allowed him to implement his ideas.
“Every company has to evolve,” he said. “If anything, the founder actually took the blinders off and let go of some of the controls, which can be a huge challenge for entrepreneurs.”
Bootstrapping and Automation Tools
Steve is a firm believer in a bootstrapped mentality — the idea that success comes from putting in the work, not shortcuts.
”Do the work. Hit the ground running,” he stated. “We don't believe in silver bullet solutions and we'll never be the company to tell you that there is one.”
He emphasized this when he said that automation is simply a vehicle for enhancing efficiency for those already willing to put in the effort.
“ I knocked on doors. I followed up with people the old school way. I built lists the old school way. I followed all of the sales advice. I did all this stuff,” Steve said. “And then, I came to MaverickApp, and I'm like, ‘Oh, wow, this company is founded on these principles. It just so happens to automate.’”
The Most Rewarding Part of the Sales Journey
The transition from a sales leader to company president hasn’t been without challenges.
Balancing operations, customer success, and continued sales efforts has required a shift in focus, but Steve’s passion for creating real solutions has kept him motivated.
For him, the biggest reward isn’t just financial success — it’s seeing something he built take shape and deliver results.
“It’s getting to eat what you kill,” Steve said. “ I created this and now I get to see it grow… I've always loved waking up in the morning and manifesting my reality.”
Steve’s journey is a testament to the power of betting on yourself and recognizing the right opportunities.
His leadership at MaverickApp reflects his core belief that success isn’t about waiting for the perfect moment — it’s about committing, adapting, and executing.
“If you ever find yourself ranting about something that bothers you, start a company to fix it,” Steve suggested. “Whatever you're complaining about in life, it will resonate with thousands of other people. Go sell the solution to it.”
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