Product Manager to CEO
in 10 short years

People come to this site (almost always through a search engines) looking for information on writing MRDs. They also get a good product planning outline and, from the emails I receive, that seems to be worth something to them.

This article is more of a reflection of climbing the corporate ladder and my experience of moving from a product manager to a CEO with a couple of VP of marketing stops in-between. A little on how I did it and how, looking back, I could have prepared myself better.

Backpacking in a forest fire

What would have better prepared me for a role as CEO of a technology company? I think the best preparation that I had was a vacation in mid-1980s where I was out backpacking. In the middle of the trip, a forest fire was ignited by lightning which turned out to be one of the largest forest fires in California in 20 years. We were three days into the trip when we first saw the smoke. It wasn't long until there was very little visibility at all. This was before the days of GPS, so we would normally use the sun and the mountaintops to figure out our position, but none of that was visible. The water was covered in ash, so drinking was an issue as well. We had no idea exactly where the fire was or how to get back to civilization. This is exactly what it is like to be CEO of a company. There are many external forces that can impede your progress, the tools that you have for deciding on direction are very limited, and the whole situation could be completely overwhelming if you think about too much. The only way to make progress is step by step - knowing your overall goal, but going one step at a time, adjusting your path anytime you get more data along the way and rationing your food in case it takes you longer than you think. We did make it out of the fire all those years ago - scratched up and a few pounds lighter, but happy to be alive. It was extremely difficult climbing through brush and working to get our bearings with very little information available, but we managed it - step by step. That is what being CEO of a company is like - you know your destination, you know your capabilities, but you can't see what is going to happen to you just around the corner. The only way to succeed is to take it step by step, knowing your goal, and changing direction as new obstacles present themselves and never, ever, giving up.

How being a CEO different than product manager

In some ways, being a CEO is no different at all then being a product manager. You are responsible for everything and yet there is are outside influences that are out of your control. Yet in some ways it is very different. As a product manager, you have all the responsibility, but none of the authority and you need to coax, cajole, or con people into what is best for the company. As CEO you have a level of authority that is easily misunderstood and even more easily misused. But you still have to build consensus and make people feel like they are part of the decision process so, from that perspective, product marketing prepares you well for the CEO role.

Product marketing is the one job that gives you the broadest view of the way a company functions. You work closely with sales, engineering, finance, customers, suppliers, and upper management. However, you don't get the detailed exposure to some areas of the company that you will need to know more about - specifically sales and finance. I actually was a sales rep, I even managed one or two sales people before I became CEO, but I didn't get the type of sales training that you need to be CEO. When you are CEO you are always selling; whether it is customers, employees, or investors; you can't have those sales skills honed well enough. The finance side is a bit different. As a product manager, you are generally involved in pricing, gross margin, and revenue discussions from the very beginning. But it is important to know more about how that flows into the income statement, cash flow, and balance sheet. It is also important to understand the investment structure of a company. Dig into that stock plan and understand outstanding shares and who has what percentage of the company.

Another major difference is, as a CEO, you manage a more diverse group of people. Managing marketing people is surprisingly easy. They tend to be people who are team oriented and extremely independent. Managing sales people and engineers is a different story all together. They are much more individual contributors and more self-focused than marketing people.

Three things you can do to prepare yourself for the next level

Here is where I get to do the hindsight thing. If I were starting over again as product manager, what would I have done differently to prepare myself for the CEO role? Listed below are my thoughts.

Number 1 - Start thinking like a CEO now. What is that supposed to mean? As a product manager you already "think about the big picture". You are always thinking about how your product impacts the company's bottom line, so what is the difference? The difference is thinking beyond the product. As product managers, we tend to get very product-centric - if we just had these features, we could go after this market. But a company is so much more than product, it is service, it is positioning, it is people. As a product manager, you are a lightening rod for all lots of ideas within the company. Use that position to make sure that your company is offering the best service possible. Think beyond product, think of your position as a company in the market. I have covered some ideas on how to bring people together to talk about the product roadmap in my book chapter on product planning. If you are leading these discussions, you are leading one critical aspect of the company. Think about the people in your company and how you can motivate them to help you build the company. Leadership is one of the key characteristics for a CEO. Which brings me to point number 2...

Number 2 - Brush up on people management and motivation. The company is the people and the people need to feel that. You may think that you need to be a "larger than life" figure in order to lead your company to success, but the truth is that you need to be much more than that. Sure you need to motivate people and make them feel good about their company and what it is they are doing, but you also need to communicate on every level. People feel much more involved when they know what is going on. Get in the habit of telling people "why". Why this product important, why this feature important, why this market is important. As a product manager you don't get much of an opportunity to manage a large number of people so take any opportunity presented to manage people whether it is directly or indirectly.  I highly recommend Alan Loy McGinnis little book Bringing Out the Best in People.  It is an easy read and packed with valuable reminders on how to work with people.

Number 3 - Live in the sales world for a while. A CEO is always selling whether it is to customers, investors, or employees. Understand sales processes including creating a vision, the sales funnel, follow-up, closing, and knowing when to walk away. All these skills are crucial no matter what you are selling. They will also help you judge the quality of your sales staff. To many of us with a technical background, the idea of doing time in sales is about as interesting as the idea of doing time in the dentist chair. But unfortunately, learning basic sales skills takes practice and the best way to get practice is to be on the firing line. You can take sales courses, which will help you understand the theory (which I would definitely recommend), but you need practice to hone the skill.

If I allowed myself a number 4, it would be learn as much as you can about fundraising. If you become CEO of a start up, you will constantly be raising capital. Learn as much as you can about the fund raising process, including why investors invest in companies, what they look for when making investments. Unfortunately, there are not many resources available to help you. There are a couple of books that are good reads in this area though including Ruthann Quindlen's book, Confessions of a Venture Capitalist.

One more book that I think is important to recommend is Jim Collins' book Good to Great.  This book gives you an inside look at building companies that are truly exceptional. 

My personal path from Product Manager to CEO

I went from Product Manager, to Director of Product Marketing, to VP of Marketing, to CEO. When I look at the resume of someone I am interested in hiring, I always look to make sure that they have a track record of staying at a company for more than a year. One or two jaunts at less than a year are fine, but if that is all that is on the resume, I quickly put it aside. I also make sure the person has been promoted within a company.   I figure that if someone is thought of highly enough by the people that work with them every day to promote them to the next level, than they must be pretty good. Often times, when you get to know a person well, it is easy to concentrate on their weaknesses. I think it is most common, especially when promoting to a VP level position, that companies look outside to bring in help. So someone who has been promoted from within is a pretty good bet, especially if they have been promoted multiple times within the same company. (All this assuming this is in a healthy, thriving, company. Otherwise, the promotions don't mean as much.)

I promote people based on their capabilities in their current job, their leadership, and their willingness to take on new responsibilities and their ability to think outside the box.

There is a whole lot of luck and timing that goes into anyone's career and mine is certainly no exception. I had no intention of becoming CEO when I joined BoldFish in June of 1999. I had to think very hard about whether it was what I wanted to do when the job opened up. I had two small children at home (one less than a year!) and I wasn't sure that I could juggle both. But I have always loved a good challenge and I have always believed that I excel when I am overwhelmed and forced into high gear. I really believed in the company, the people, the investors, and a market space, so it was an opportunity that was almost impossible to turn down. So that would be my final word of advice - take advantage of any break that you get (you never know when you are going to get your next one) and may luck be with you!