Is your company product-led, sales-led, or marketing-led?

When I started as a product manager at Microsoft Outlook in January 2015 I read a post on Quora that said you should 10x something in the first 90 days on the job to set yourself up for a good career trajectory. In that same post it said “engineering types” like me tend to miss the point of companies which is to make money. And so was born my plan out of college: 10x money for Microsoft Outlook. (I know…)

During my first day at work my manager took me to lunch. I asked him to introduce me to someone in finance. He said that was an unusual request but proceeded to put me in contact with someone in marketing. 🤷‍♂️ I then tried to figure out the money situation by asking my skip level manager to help me fill out the “Business Model Canvas” for Microsoft Outlook. He was reluctant to take the meeting and when he did he was very confused. He told me not to think about that. I vividly remember what he told me I should think about: “Philipp, think how to get people to upgrade Outlook Desktop to newer versions because a lot of the issues people have stem from the fact that their on-premises Outlook is from 2010 and those things have already been fixed in the new Outlook.”

I was pretty annoyed because things weren’t going according to my plan one month in. I was also not a fan of being patronized. I didn’t feel valued. Before joining Microsoft, I had just crushed it at Amazon the summer before and was in constant communication with Andreeseen Horowitz (AH) where I was treated as “talent”. My talent manager at AH vehemently tried to dissuade me from joining Microsoft and warned me that if I joined two things would happen:

  1. I would be forced into the “rat race”, constantly fighting for the next crumb with my peers instead of actually acquiring and growing skills.
  2. I would never leave Microsoft because of the “golden handcuffs” a.k.a. the large amounts of money they pay you.

Being a poor immigrant from Russia all my life who just borrowed $100,000 to attend University of Michigan, I really wanted to get to the part where I was “making money”. I had idolized Microsoft from a young age. At the age of 12 my family was able to afford my very first Microsoft Windows Dell computer on which I learned how to code. I assured him I would leave after 1 or 2 years max and refuted him by saying I would “learn a ton”. As you can imagine though, right around this point I was really starting to bide his words and decided I had made a terrible mistake and would quit and look for a startup job.

Luckily, we had a “reorg” the next Monday and both my manager and skip level manager were no longer that. It was Satya’s new “growth mindset” management changes making their way down the organization. My new manager was incredible, she listened, she helped, she mentored.

With her help I quickly got to the TRUTH: Microsoft Outlook is part of Microsoft Office which is sold to CTOs or CIOs at large enterprises by small sales teams with someone extremely charismatic taking point. (I don’t know if the swanky steak dinners and yacht trips are exaggerations though?) The subscription is a 3 year plan bought up front and Outlook is one of 30 or so products.

“Oh shit”, I remember thinking, “How can what I do, product development, 10x that?” It dawned on me that I was in a sales-led division of Microsoft. No big deal I thought though, I just need to figure out how to have product tied directly to money. New plan: Turn Outlook into a product-led division of Microsoft by tying product to money. (I know, I know…)

When the disparity between being “sales led” and product gets too large problems arise. If you are exceptional at sales you need to at least be good enough at product. If you are not, competitors emerge and take advantage of your weaknesses. For example, if they are product led and you are not, they will showcase that their product makes employees much more productive and happy.

With GSuites breathing down Microsoft’s neck, Outlook was already on its way to improve the product development process. It was critical to transition Office from the 1/1/1 waterfall model (1 year research/1 year of building/1 year of stabilization) to an agile methodology to compete with the way Google was releasing 10s of changes per month. As part of this plan, Microsoft acquired Accompli founded by Javier Soltero. There were really two purposes:

  1. The obvious one of a mobile client for Outlook and,
  2. The less obvious goal of getting Outlook to be more product led. 

The transition duties of #1 delayed #2, but finally Javier Soltero was named the VP of all of Outlooks right around when I had my “oh shit” moment. So with a ton of luck and a totally revamped leadership team I made my career at Microsoft working on beefing up Outlook’s product team. 

When thinking about career now, my startup, and doing sales, that lesson sticks with me. It’s absolutely critical to understand if a company is product-led, sales-led, or marketing-led. It is the air which the company breathes. It will formulate the context of how everything is done, the amount you can learn, and the things that are valued. After all, it is what makes money. You will feel like you are always swimming against the current if there is a mismatch. Don’t make the mistake like me, figure it out beforehand. 

Being product led attracts the best product talent, being sales led attracts the best sales talent, and so on. If you want to be valued and work and grow around the best talent in a discipline, that’s where you’ll want to head. If you’re maximizing wealth however, you can look for such mismatches where companies are trying to beef up a secondary discipline or react to a competitive threat. You can perform a type of “financial arbitrage” to help along that transition instead. I’ll warn you, it’s painful work though. Even with the support of the leadership team.

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