Making your customers your secret weapon (with Highspot's Oliver Sharp)

Ben Gilbert (0:00)

Hello, Acquired LPs, and welcome to another very special episode of the LP Show. David and I are here today with Oliver Sharp. Hello, Oliver.

Oliver Sharp (0:10)

Hello. It's great to be here with you guys. I've spent many, many hours listening to you on your podcast, so it's great to be a guest as well.

Ben Gilbert (0:19)

Well, Oliver is, for folks who've never met him, one of the most thoughtful people. Every time I get into a conversation with you, I leave feeling smarter, I explore topics I didn't expect to explore, and we can be talking about anything here on the podcast today, and I'm sure it would make for great content. And so I think actually you and I were first chatting at the Convoy live show when you came and I was like, oh my gosh, there's so many episodes in here. What direction should we go with it?

I think we'll get a lot into Oliver's background, but just as a quick aside, they are Seattle's most recent unicorn. He is the co-founder of Highspot, a great local company here that we're going to talk all about today.

A lot of the different strategies and tactics that they use and lessons learned over the years. Congratulations, Oliver, on the big financing round, well, announced earlier this week.

Oliver Sharp (1:08)

Yeah, we announced on Monday and it's a really exciting moment for us because we have some really big strategic goals that we're trying to achieve and this gives us a little more fuel to go after them.

Ben Gilbert (1:22)

Well, I'm going to turn it over to you a little bit.

You have a storied background, a big company life at Microsoft, startup life and back again. You were a TA for Bill Gates, is that right? A technical advisor?

Oliver Sharp (1:35)

So Bill has a technical staff, which traditionally was one person, the TA. And when I was on that staff, there were two of us. There was Eric Rutter, who was his TA, and then I worked with Eric. So the two of us kind of supported Bill in a variety of ways. And that ranged from investigating technical questions.

We were kind of an independent voice that didn't have a stake. So if multiple teams were having challenges with each other, you could send us in and we could be sort of the ombudsman, if you will, and go dive in and pull together a way of thinking about it that didn't adhere to any one particular team's point of view. We also ran, for example, his Think Week twice a year. And we also attended many or almost all of the Bill G reviews, which are kind of a famous institution at Microsoft at the time, where every team in the company basically would come in and present to Bill, often for many hours, and go deep into their particular technology or their industry.

So we got a pretty amazing view of all the different things that the company was up to.

Ben Gilbert (2:39)

And this is like a pretty storied function at Microsoft. Oliver, I feel like that's a good place to start over in sort of Microsoft land a little bit.

How did you end up joining Bill's technical staff and then, you know, what is the tour of duty on that look like in terms of number of years and what did you do afterwards?

Oliver Sharp (2:57)

Yeah, so my history with Microsoft is actually kind of funny. I've worked there three times.

I was an intern in 1984 when the company was behind the Burger Master in Kirkland. Then they bought the first company that I was involved in getting started, which I also did with Robert, who's the CEO of Highspot.

And we were grad students together. And then we did a startup out of grad school and Microsoft acquired it. So that's how we ended up at Microsoft. Then I left and did another startup, a second startup. And then Robert got me to come back to Microsoft for a third time. So I kind of got to see the company at three different stages in its evolution. And I got to see how the culture evolved. When I was there the second time, which was after the acquisition, I got to know Eric Rudder, who was our GM when we first joined the company, our general manager. For those who don't know, Microsoft traditionally divided their world up into product units and then product units reported into a general manager. And so he was the general manager over a set of product units, one of which was the one that I was in.