Jeff Bailey

I describe myself as a %22blue-collar executive.%22 My career began at age 14 as a brick mason’s helper, followed by years as a union railroad employee, before I earned my way up into software technology leadership. Because of that background, I look at business from a practical, grounded perspective. Having served as a COO, CRO, and CEO, I focus on bridging the gap between high-level growth goals and the real work that happens on the front lines.

Rather than telling you how to run your company, I serve as a collaborative, objective sounding board to help you stress-test your strategy, review key decisions, and look around corners. My collaborative approach is backed by measurable results from my seven years leading a major software business unit:

Balanced Scaling: We grew an established operation from $15M annual revenue ($3M recurring) to $50M annual revenue ($26M recurring), building a diversified customer base that included double-digit Fortune 500 accounts.

People-First Retention: We achieved this growth while maintaining a 98% customer retention rate and a 95% employee retention rate. This sustainable focus earned us Best Place to Work in Atlanta for five consecutive years, and I was honored twice as a Titan 100 Executive in the state of Georgia.

The Companies That Benefit Most From My Advice

I am built to support business owners who value steady, practical leadership:

Founder-Led SaaS Scaleups ($10M to $50M ARR): Companies that have found product-market fit but need to structure reliable enterprise sales, marketing, and customer success frameworks without disrupting a healthy company culture.

Traditional Businesses Modernizing Through Tech: Established professional services, logistics, or industrial firms that want to adopt modern software and automation. I help you vet these tools to ensure they protect your margins and deliver a clear return on investment without interrupting day-to-day operations.