Jay Holstine

Managing Director of Compass Partners

Jay Holstine’s passion is building an empowering and high-achieving CEO Peer group that produces more effective leaders. The CEO peer group enables members to make better decisions, grow their companies, build a more fulfilled workforce, and provide benefits to their communities.

Jay Holstine meets with members one-to-one to discuss issues, opportunities, and business strategy, on top of the monthly CEO peer group meetings. The one-to-one drives the purpose and focus of the overall Vistage experience and enables more effective CEO peer group monthly meetings. The select group of 18 motivated business leaders from non-competing companies helps process each other’s opportunities and issues to surface root causes and provide experienced judgment and perspectives. In addition to benefiting from shared wisdom, the CEO peer group provides a confidential space for brainstorming, troubleshooting, and camaraderie. That cannot be found among a CEO’s business team of advisors with competing interests.

As a growth-oriented former CEO, Jay brings pragmatic methods and incisive analysis to help CEOs improve their work-life balance and transition from working-IN-the business to working-ON-the-business more effectively.

Concurrently, Jay Holstine serves as managing director of Compass Partners, advising early-stage startups on strategic go-forward plans, governance, building teams, key talent acquisition, board presentations, raising investment capital, and building scalable structures. Historically over 30% of Compass Partners client companies have had a successful exit.

With a mechanical engineering degree from the University of Kansas, Jay Holstine began his career as a manufacturing operations consultant with Accenture in New York and worked as a supply chain strategy consultant with Deloitte Consulting. Jay left consulting to serve as the plant manager for Taylor Instruments near Asheville, NC. In 2001, Jay founded SigmaFlow, a cloud-based process management solution that he successfully sold to a private equity company in 2012. Subsequently, Jay has been the CEO of several software companies.

Where did the idea for your career come from?

I’ve co-founded 5+ companies, and we start by identifying a preferred niche, then arrange conversations with thought leaders to inquire about high value processes that involve multiple departments and are currently manually managed. This approach has been successfully applied in diverse industries such as Oil & Gas, Electric Utility, Healthcare, and multiple compliance solutions.

What does your typical day look like and how do you make it productive?

My days are very full with one-to-one executive coaching sessions, planning speakers and logistics for the monthly Vistage meetings, and consulting projects. My calendar is my most important productivity tool, and I use Calendly so that clients can schedule time with me.

How do you bring ideas to life?

Working backwards from the voice of the customer, and focusing on the customer pain, then assessing the market, then assessing the competition.

What’s one trend that excites you?

Bringing technology to blue collar industries. For example a roofing company using drones for estimates to reduce the quote cost by 90%, or a painting company using robots to reduce the labor cost by 30%. Applying technology is disruptive, improves scalability and margins.

What is one habit of yours that makes you more productive as an entrepreneur?

Listening to the Voice of the Customer. Asking probing questions. Low hubris. Entrepreneurs need to talk less, and listen more.

What advice would you give your younger self?

Be more patient and vet deals.

Tell us something that’s true that almost nobody agrees with you on.

Employee engagement is more important than customer engagement.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Quantify customer pain. Quantify value. Effectively deliver value.

What is one strategy that has helped you grow your business?

Create a good company culture to attract the best possible employees, who in turn will take great care of the customers.

What is one failure you had as an entrepreneur, and how did you overcome it?

We utilized a third-party component to perform complicated simulation calculations. After some time we became concerned about the third-party company, and the potential risk for our customers, so we hired experts to internally build our own simulation engine.

What is the best $100 you recently spent? What and why?

Golf lesson. I was struggling, and the pro was able to quickly recognize what needed to be changed.

What is one piece of software or a web service that helps you be productive?

I like using LinkedIn Navigator to identify subject matter experts.

What is the one book that you recommend our community should read and why?

The Road Less Stupid by Keith Cunningham. Keith is down to earth, and provides pragmatic advice that can be applied by businesses of any size.