Last week I spoke at Harvard Business School with MBA students who are thinking about a career in Sales. Thanks to Mark Roberge for having me.

Most of the students were looking at Sales as a path to CEO.  It’s not the only path, but it’s a good one. If you or someone you know has the same strategy, here are some of my suggestions:

1. Pick the Right Company

Warren Buffet likes a “margin of safety” when he invests. I suggested three key elements that would increase the odds of success:

  • Pick a Growing Company in a Big, Growing Market. Facebook COO Sheryl Sandberg said, “If you’re offered a seat on a rocket ship, don’t ask what seat! Just get on.” In a growing company, you will have many more sales “at-bats.” You will grow your network faster. That means more mentors, customers, partners, investors, and co-workers.  And when you build your team someday, you’ll have a large, ready-made group of people who know and trust you.
  • Pick a Company with a Great Brand Name and a Successful Track Record. Later in your career, you will get more opportunities because you worked for a “known quantity.” You will be part of the “GreatCo Mafia.” As a VP of Sales, I see so many resumes with companies I don’t recognize. I almost never interview those people. If the company is #1 or #2 in its market, you will have more sales success.
  • Pick a Company with Great Training Programs and Proven Sales Leadership. Early in your sales career, take time to build your foundational skills. Companies that train you in proven sales strategies, tactics and techniques help you build that foundation. Work for sales leaders who have been successful as reps, managers and executives. They will teach you the most. Maybe that first-time sales time manager will be great. Maybe not.

One caveat: you should also pick the right company that is right for YOU. Many paths can lead to success if you work hard. Examine your personal preferences:

  • Customer Type. Do you prefer selling to line-of-business executives or IT executives? Do you prefer business apps or IT apps?  Do you prefer selling to large companies or small-medium ones?  Do you prefer selling into a certain industry like high-tech, financial services or healthcare? Do you prefer selling to certain functions like sales, marketing or finance?
  • Sales Type. Do you prefer high-volume, lower price, short cycle inside sales?  Do you prefer complex, high price, long cycle field sales?  Do you prefer hunting for new customers or growing existing accounts? I have a bias for hunters.

2. Carry a Bag First

Many of you would like to start your sales career as a manager. I say carry a bag first. Why?

  • Learning. You’ll learn a ton about sales, business, communication and human nature. And you’ll learn it first-hand by doing. You’ll succeed and you’ll screw up. Personal sales skills will also help you as a sales leader and CEO down the road.
  • Credibility. You’ll be a better coach and manager because you’ll have first-hand knowledge and empathy. When I was a Marine officer, I learned the value of “leading from the front” and “leading by example.” The same principle applies here. Salespeople will follow you if they see that  you can sell.
  • Money. Top performing salespeople are the highest paid employees in a company. Give to charity. Save money for your own company. Blow it all in Vegas. The choice is yours.

3. Think in 2 Year Sprints

One strategy is to spend about two years in a single role, then move onward and upward. Spend 100% of your time during the first 18 months being the best at the role you’re in. Then, in the final 6 months, spend 20% of your time putting yourself in position for the next one. One path could be

  • Inside Sales
  • Field Sales
  • Sales Manager
  • Regional VP
  • National VP
  • Global VP
  • Chief Revenue Officer

Bonus: B2B Sales VP Reading List

If you want to learn about sales and sales management, these are a good start.




Sales Management



I’d love to hear your thoughts in the comments.

Happy Selling!