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7 Questions with Wilson Zehr

Name: Wilson Zehr

Current title: CEO

Current organisation: Cendix (Zairmail)

Wilson Zehr has 20+ years’ experience in high technology and telecom - over a decade working with Internet-related (SaaS) products and services. He started his career as a Software Engineer; then expanded into full life-cycle product marketing, program management, strategic alliances, executive leadership, and teaching.

Professor Zehr serves on the faculty for Eastern Oregon University and teaches marketing, finance, entrepreneurship, management, and business policy & strategy. He is also the co-founder and CEO of Zairmail (, Cendix (, and Eastern Oregon Ventures.

Over the course of his career, Wilson has created numerous new products/brands and successfully brought them to market. In addition, he has established and managed strategic alliances with many of the world’s largest technology and communications firms. Dr. Zehr is also a serial entrepreneur who has been part of, started, or advised more than a dozen technology startups.

7 Questions with Wilson Zehr

1. What have you found most challenging as an Entrepreneur?

The most challenging problem is learning how to manage many different types of activities at the same time. Finding partners with the right skills and trusting them to own part of the solution. Keeping a positive and enthusiastic attitude even when things are challenging and stress levels are at their highest.

2. How did you become an Entrepreneur? Can you please briefly tell the story?

I was always looking for business opportunities as a child (e.g., paper route, mowing lawns, growing/selling artichokes, music production, building race vehicles...), but then lost some of that entrepreneurial drive when returning to college as a 22 year old Freshman.
After graduation, I worked for 5 - 6 years as a Software Engineer. I really wanted more control over the direction of the company, rather than just putting in hours and checking bullets off a list. I returned to school to earn my MBA and moved into marketing as a Product Line Manager. I also managed our strategic alliances with computer platform vendors (e.g. Sun, HP, IBM, DEC...).
I really loved this job because it was like running a company within a larger organization. The only major difference between being a full lifecycle Product Manager and running a standalone venture, is that you don't have to worry about making payroll and covering the day-to-day expenses, the rest of the activities are very similar.
I left this role when the company transferred me to the east coast and joined one of the hottest startups (at that time) in Portland. I managed our global relationship with Oracle corporation. This relationship grew to a $300 (+/-) million-dollar business for the company. I had products to manage, customers to serve, and relationships to create and nurture.
Then in 1995, when the Internet was hot (pre-bubble), I had a chance to create a venture from scratch working with some friends. The venture was jointly funded by Intel, Microsoft, France Telecom, and Telecom Italia. We created VoIP applications for telephone companies and Internet service providers. I mapped out the market, wrote the specs, working with engineering to get it built, and then followed the product into the field, when I worked with sales to close 90% of our revenue. The company was eventually sold to a telephone company in Canada for $160 million (a lot at that time).
Since then, I have started, grown, and sold a number of technology ventures. I have also helped dozens of other early-stage ventures solve pivotal problems. I’m spending more time these days teaching marketing, entrepreneurship, and business strategy at the university level. Over the past six years I’ve worked with student teams to complete over 90 consulting engagements with community partners.

3. How do you structure your work days from waking up to going to sleep?

No two days are exactly the same. That is one of the things that makes the job so interesting. I usually start the day at 6:30 going through email, catching up on communication, and mapping out the day. Then I address the most critical issues first. It is important to identify tasks where others are dependent on your input(s) to complete their work, and make sure that they have what they need. I also carve out at least three days a week for fitness and exercise. This works well as a 90-minute lunch (break). Great opportunity to step outside the action, clear my mind, and return with a fresh (positive) outlook. A friend shared a Buddhist saying with me one time. When the body is tired, exercise the mind. When the mind is tired, exercise the body. It seems to work pretty well for me.

4. What's the most recent significant leadership lesson you've learned?

It is great to be driven, most great entrepreneurs are. However, you have to be conscious of the skills, experience, and cadence of those around you. Success is usually the product of teamwork, not just the actions of one. If you push too hard, they can push back. If you are unrealistic, they can just give up.

5. What's one book that has had a profound impact on your leadership so far? Can you please briefly tell the story of how that book impacted your leadership?

Good to Great

One of the key points in this book is the importance of people. We need to get the right people on the bus, the wrong people off the bus, and get everyone in the right seats.

This aligns well with a rule of thumb in technology ventures. A players tend to hire A players. B players tend to hire C players. C players hire D players. The slide backwards continues from there...

It is critically important to recruit the best team possible for the venture. It is also important to realize that this can be context dependent. Just because someone can hit a baseball, does not mean they can run with a football.

6. How do you build leadership capacity in your Organisation?

Recruit the best team possible. Provide clear goals and access to the resources required. Get out of the way and let people do their part. Assure that you are always available as a resource. Encourage innovation and informed risk-taking, but reward success.

This really does start with having the right people. When hiring, we are really looking for three things.
(1) The technical skills required to be successful in the role and grow. We don't want people to start maxed out in a role, we want them to be able to grow.
(2) Fit with the team. We are trying to build a cohesive team that works well together. That doesn't mean that everyone should be the same. Quite the contrary, we are looking for diversity in skills, experience, and orientation. A little constructive friction usually leads to more innovation and better outcomes. Still, we need to be able to embrace this diversity in a way that brings the team together.

7. What is one meaningful story that comes to mind from your time as an Entrepreneur so far?

There are lots of great stories from my career as an entrepreneur. I love to share them with my students.

One of the biggest pleasures I've had in recent years is hearing the stories of others. I started a series of Pub Talks in eastern Oregon that give entrepreneurs with a connection to the region an opportunity to share their entrepreneurial journey. These talks are given in person, live streamed across the state, and published online.

There are a number of key learnings and exceptional stories. You can view them at

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