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Five Things I've Learned About Enterprise Product Strategy

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Over the years I've picked up both successes and battle scars on the topic of enterprise product strategy. As a former product leader at Docker, VMware, and AWS I built and managed multiple enterprise products and teams, and now as a venture investor at Mayfield I assist and advise startups on product and go-to-market strategy. Recently I had the chance to share some of these experiences in a presentation and Q&A as a part of the Angular Ventures Insights webinar series. Here's the full video for "Five Things I've Learned About Enterprise Product Strategy", and below my key takeaways and slides.
1. Prioritization: The Power of Focus Many founders and startup product leaders like to talk about their grand product vision, and then all the features they want to build to accomplish that vision. The truth is that most startups die of indigestion, not starvation. As a startup you have a limited set of resources you can choose to allocate, so there is an incredible…

Where I'm Hunting for Enterprise Infrastructure Startups in 2020

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Putting the Product in Product-Led GTM

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Product-Led Go-To-Market is a hot topic in the world of software today, and doubly so when it comes to open source software. Ultimately, getting Product-Led-GTM right comes down to getting the fundamentals of your product right, which means getting your bottoms-up value proposition, user/buyer upsell pipeline, and commercial vs. open team culture balance absolutely right. This can get tricky in practice and has its own nuances.



A few months ago, I gave a presentation at the first inaugural Open Core Summit (OCS) on "Putting the Product in Product-Led GTM", a deep-dive around how to optimize your product strategy, architecture, and teams for commercial open-source software with a bottoms-up adoption model. These insights came from experiences in both my past operator life as a product leader at Docker, VMware, and AWS, as well as my current investor life at Mayfield working with product-led GTM companies like Rancher, Hashicorp, and DEV Community.

In the spirit of the open-so…

From Servant Leader to Servant Investor: Year One of a PM Turned VC

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There is a profound intimacy that early stage investors develop with founders, and it stems from long days and late nights spent in the gritty business of company building.

Some months into joining venture capital at Mayfield, I had coffee with a friend who asked me a question I’d heard more than once up to that point. The conversation went something like this:

”So, done any deals yet?”

“Nope. I’ve actually been spending a bunch of time helping our portfolio companies with whatever they need, like product strategy, marketing, pricing, and hiring.”

“Ah got it, so they can be a deal source or reference for new deals you’re trying to win?”

“Well, not really. I'm doing it to help our companies succeed."

I am now just over a year into my venture capital career, and I have now indeed done some deals. But I have come to realize that I am not here just to do deals. I am here to help build companies. I am here to be a servant investor.

Perhaps that terms sounds familiar. Any product ma…

The Four T’s: a PM-turned-VC’s framework for evaluating startups, part two

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This is part two of a series on The Four T's. Check out part one here.

Evaluating startups is part dark arts, part science. No two companies are the same, and certain traits just can’t be quantified effectively. But like any (former) product manager, I’ve put together my own framework that has helped me to assess startups in a structured and straightforward manner. I call this framework The Four T’s: Team, TAM, Tech, and Traction. Check out last week's article for more background. This week, we discuss Tech and Traction.
Tech

This is the area that most founders focus on, and on the surface it makes sense--people naturally want to talk about what they are building and how it will fundamentally disrupt the status quo. The truth is that most founders spend a bit too long on this section and not enough time on the team and problem context. if you don’t believe me, read this report from DocSend that analyzes which slides early stage investors tend to focus on. Spoiler alert: it’s th…

The Four T’s: a PM-turned-VC’s framework for evaluating startups, part one

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This is part one of a series on the Four T's. Check out part two here.

Evaluating startups is part dark arts, part science. No two companies are the same, and certain traits just can’t be quantified effectively. But like any (former) product manager, I’ve put together my own framework that has helped me to assess startups in a structured and straightforward manner. I call this framework The Four T’s: Team, TAM, Tech, and Traction. This week we'll start with Team and TAM.

Note that I'm not the first investor to use one or more of these T's, nor will I be the last. So why write this up and throw into the depths of the internets? I recently read and was inspired by Bloomberg Beta’s Criteria for Investing, which provides a concise yet comprehensive description of how that firm evaluates companies. Similarly, I’d rather entrepreneurs are able to put their best foot forward during the pitch and focus on what makes the company a great business and a good fit for partnering wi…