Bret Taylor knows transformation in tech: He’s been the incumbent and the disruptor, on both sides of mergers and acquisitions, involved at all stages of scaling, and an initiator of many major products: Google Maps and Google Maps API, for starters.

As the founder and CEO of Quip, Taylor became president and COO of Salesforce at acquisition — a move he had experience with, having created FriendFeed and becoming CTO of Facebook with that sale. Since arriving at Salesforce, he’s played a major role in its acquisition of Slack, MuleSoft, and Tableau, with a strategic eye toward the future of work.

At the core of his leadership is a willingness to learn, stay curious, and adjust his approach as the product — and the world — demands.

“The best founders are the most curious people in the world,” says Taylor. “At every stage of your company — especially as an entrepreneur, because it changes so rapidly — you need to bring a different version of yourself.”

The grit and growth-oriented humility that approach requires has paid off in Taylor’s experience, and it’s centered on proactively hearing from customers. Rather than treating consumer listening as just some nice-sounding tagline, Taylor actually seeks out and deeply considers direct customer input, insisting that insularity and navel-gazing are company death knells.

So, what is Taylor looking toward for the post-pandemic future of the information workforce? An all-digital work-anywhere world, to be sure, but one that goes beyond trying to recast the previous in-person office onto a screen. At its center, he believes the future is about investing in and developing products to support asynchronous work for a distributed workforce — while not underestimating (or ignoring) the importance of company culture and values.

In this installment of Greylock’s Iconversations series, Taylor talks in detail with Greylock’s Sarah Guo about his vast experience, and how it applies to the current reorganization of work.

Listen to the conversation on the Greymatter podcast here.

Watch a video of the interview on Greylock’s YouTube channel here.

Episode Transcript

Sarah Guo:
Hi, everyone. Welcome to Greylock’s Iconversations. I’m Sarah Guo, a general partner at Greylock, and I’m thrilled to be joined by Salesforce president and COO — and former Greylock-backed founder and CEO of QuipBret Taylor.

In addition to leading operations at one of the most important tech companies in the world, Bret’s an extraordinary product leader who has helped conceive, create, and commercialize technologies that have touched hundreds of millions of lives. He’s the co-creator of Google Maps and the Google Maps API, and joined Facebook when his startup, FriendFeed, was acquired. Bret served as the CTO of Facebook for three years before founding productivity startup Quip, which partnered with Greylock and was acquired by Salesforce in 2016.

Since joining Salesforce, Bret has pushed for innovation and has been instrumental in the company’s acquisitions of Slack, Tableau, and MuleSoft. Bret also serves on the board of Twitter.

Most recently, Salesforce, already a dominant SaaS company, has been a leader in the all-digital work-anywhere world. Those companies have had to digitally transform through the pandemic.

Bret led the Slack acquisition, bringing Salesforce and Slack together to create the digital HQ, which we’ll get to hear more about.

Bret, thank you so much for being here. It’s a pleasure. I have so much respect for you, Kevin, and the extraordinary Quip team. I remember telling John Lilly when we invested, “This is a company I’d consider joining full-time.” And it was one of the first times I thought that at Greylock. Thank you for continuing to be part of the family.

Bret Taylor:
Thanks for having me. It’s great to see you. And it’s been a long time.

Bret, today you’re running operations in one of the largest tech companies in the world; you’ve scaled zero to one to tens of thousands of reports, and across consumer to enterprise. You remain an extraordinary technologist and product leader, but you’ve also obviously taken on a good market. It’s an incredible story of just personal growth. Tell us about how you got to now.

Sure. I went to college at Stanford, was a computer science major, code terms. I got a master’s degree. And I was there during the dot-com bubble, so it was interesting. The career fair my sophomore year in college was free pizzas for every student in the computer lab, jobs falling from the sky. And by the time I got there for my junior year, it was like tumbleweeds going through, as every single one of those businesses had gone under.

I ended up at Google largely through luck in the sense that there just weren’t that many companies left after the carnage of the dot-com bubble bursting. But most importantly is Marissa Mayer. I was a section leader while she was a teaching assistant in a class, and [she] had ended up at Google and started what became the associate product manager program at Google. And I was a member of the first associate product manager class.

It was probably the first kind of career change I made, in some ways, because all of my other job opportunities were to be a software engineer. Marissa had made the case that I should consider product management. I not only didn’t really understand Google’s business model at the time, I didn’t know what product managers did, either. But I really liked Marissa and I loved Google the product. So I kind of took a leap of faith, and it turned out to be a great decision.

Probably my crowning achievement at Google was Google Maps, but I worked on a bunch of products while I was there. And then right around 2007, I got really obsessed with what at the time was called Web 2.0 — the read-write nature of the web. And Google wasn’t really that interested in making products that were social at the time, anyway. The Facebook envy came a little later.

I tried a lot of proposals to build more social capabilities and maps at the company, but sort of fell on deaf ears. I came to the conclusion that if I wanted to work in that space, I’d probably have to do it outside of Google. So I left and started FriendFeed.

Give us a sense of scale: How big was Google when you joined, and when you decided to go do FriendFeed?

I want to say it was between 200 and 500 people when I started. We were in one small building in Mountain View. That was before we moved into Silicon Graphics’ old campus. We had a lot of contract employees doing support at the time, and I’m not sure how they play into the employee numbers. I’m not totally sure, but certainly under 1,000. And when I left, probably over 12,000. It was just a rocket ship over five years.

I left having made Google Maps, so the last thing I did at Google was our first developer conference, because the Google Maps API — which ended up being used by Trulia and Yelp and others — was sort of my passion project. I wrote it, product managed it, marketed it. I was more of a one-man band on that. And it was the first real developer product. We had an API for ads system, but not really other than automation. There wasn’t a true developer product.

And there were a number of early products there, [so we] kind of herded those cats and made our first developer conference in San Jose, which was about probably three weeks before I left the company. I was really proud of that, and seeing what Google IO is now is pretty cool — to see that evolution over the years.

I became passionate about social software. I started FriendFeed. I joke we were sort of the Apple Newton of social networks: not commercially successful, but we invented a lot of the interactions in the newsfeed that I think a lot of other social networking services adopted, much to our chagrin.

At the time, we had a good reputation in the Valley. It was a real, classic fly high and fall quickly. In the middle of, I think it was 2008, it might’ve been 2009, we were this big spread in the middle of Business Week and kind of the darlings of Silicon Valley. And then by the end of that year, Twitter had totally kicked our ass.

And so, in that six month period, I was like, “This is viable. We found product-market fit. We’re going to take over the world.” And six months later, we’re like, “OK, we’ve lost, there’s no silver medal in social networking.” We ended up running a process we knew that we had lost.

We debated pivoting, but decided that we really wanted to work in social software. We were passionate about it. So we decided that M&A was probably the better approach, ran a bit of a process, and chose Facebook at the end of that.

We had a few different offers, this was a pretty emotional decision, but chose Facebook, and I ended up CTO there. Only for about, I want to say, three years, maybe three and a half years there. I saw it through the IPO, which was really fun. I’d been at Google during the IPO, but not in an executive role. And it’s a really different vantage point to see scale.

And you talked about my career trajectory. [Facebook] was really where I learned how to become a manager, from Mark [Zuckerberg], but also from Sheryl [Sandberg], who’s really amazing. She spends a lot of her time quite generously mentoring. She taught a lot of the Facebook management team what it means to be a manager.

And so, I learned the hard way. I definitely wasn’t perfect there, but the organization scaled much larger than I ever had before. And I’m very grateful to this day that Mark gave me that chance and that opportunity.

It’s still funny, though, because I think I was 29 at the time and often the oldest person in the room at Facebook that year. It’s just a different, other company [now].

The big transformation there was mobile. Facebook is doing so well now, I think people often forget that, when we went public, our stock was depressed for almost the entire first year, in part because our user base had moved to the smartphone, but our monetization hadn’t. And so there were a lot of questions about Facebook as a business.

What became our mobile app, installed ads, and a few other things [happened because] we were in real-time trying to move our business model to mobile. [We were] still dominated by the right rail of ads on the side of Facebook and a browser.

We similarly had lots of fits and starts and just adopted into the smartphone revolution. [It was] a famously poor application for a while. I led the reimplementation on iOS and Android. And we got through all that, but [with] a lot of battle scars from that experience.

On the other side of it, I realized just how much our consumer lives have shifted to the smartphone, but enterprise software hadn’t, and became obsessed with that. And that’s where Quip came from. It was one angle of saying: If you were to reimagine the way we work around push notifications, around the smartphone, around the tablet — which at the time seemed like it was going to be bigger than I think it turned out to be — what would you build, and how would you re-architect the way we work?

I started Quip at the end of 2012. And then, as you mentioned, Quip ended up being acquired by Salesforce, and I’ve been here for about five and a half years. So a pretty long time.

It’s been that long. Oh my gosh. It’s an extraordinary set of companies and products that have changed the world.

You mentioned that you had to learn to be a manager and a leader. You have — as one of an exceptionally small group of people — managed both very small teams having a big impact, and then very large teams having a big impact.

One analogy we use with entrepreneurs at Greylock is: If you’re lucky enough, you have rapid organic or enterprise adoption, and each year your company is suddenly two or three times bigger. And I personally haven’t grown as a leader two or three times in the past year. It’s a really hard thing to ask of people. It sounds like there are certain people who helped you, like Sheryl, for example. What helped you stretch back and forth across these different modes of operating these different scales?

Yeah. I mean, one of the things that I’ve learned, as a CEO and as an entrepreneur, but in general with my jobs — I think the flaw, and the mistake I made early in my career that I’ve gotten better at, is, rather than trying to conform your job to you, think about what is the most important thing this job demands of me and change yourself.

I remember when I first became CTO of Facebook, everything from my staff meetings to just the cadence of my job was sort of what I wanted to work on. And I realized over the course of some swings and misses in that experience, that, if I approach the state and say, What’s the most important thing that I want Facebook to achieve, and how can I affect that outcome?, it would really transform my day and transform the way I worked.

I look at scaling a company, and really early on in a company’s life cycle, probably the answer [to that question] is products, right? You don’t have one yet, you need to work on it. And you need to spend a lot of time with your early customers and make your product useful.

If you’re on the enterprise side, you need to make your customers successful and create enough value that someone will actually pay for the thing. It’s a lot of rapid fire for the duration. You might get to that next phase, where you found product market fit, and maybe the thing that’s most valuable for your company is recruiting and finding the leadership team that you need.

Maybe you’re the effective chief product officer, and you need a chief product officer for the first time. Maybe you’ve gone from a sort of grit-driven sales [team], and you need a real head of sales. You’re going to really need to scale that motion. Maybe you’ve relied on PR and word of mouth for marketing, and to get to that next level, you actually need to optimize your paid customer acquisition.

And then, later, you might find that your leadership team’s not working, and you need to dive in and fix something or change out your leadership team.

“At every stage of your company — especially as an entrepreneur, because it changes so rapidly — you need to bring a different version of yourself. “

And I think that’s really hard. I think it means that some parts of that journey might be really fun, and some might feel totally unnatural and actually quite uncomfortable. You might be kind of miserable through it, because the part that made you successful in the phase before is not the part that will make you successful in the phase after.

If you look at the great entrepreneurs, the ones who have scaled from those early stages all the way to becoming successful CEOs of public companies, I think they’ve gone through these transformations. And that’s one thing that I’ve really embraced, and it was really hard for me at times.You end up having to have the humility to recognize how you need to show up, and then just how rapidly that changes.

I think it’s an amazing lens. You’re a legendary founder, a legendary product guy and operator. But I think sometimes there is a type of legend that actually is a disservice to founders and operators as they’re scaling, that’s like, You’re perfect. You’ve got the vision and you don’t need to change yourself. You don’t need to grow. That’s just clearly not the case in terms of the scaling and the learning that people go through. So thank you for sharing that.

I probably spend half my time thinking about recruiting. When you are evaluating whether leadership hires can scale down from jobs at bigger companies — so I’m thinking like Molly Graham, for example, or any of the other early Quip folks and operators at that startup, or when you hire at Salesforce and you’re looking at non-obvious backgrounds — what do you look for? How do you get yourself comfortable with the risk of people’s profiles, what they haven’t done?

First of all, there’s not a magic wand here. I’ve made a lot of bad hiring decisions and a lot of great ones, and you learn from all of them. There’s not one litmus test that determines whether people can be successful.

But I’ll say a couple of things. One is that there’s a certain amount of grit necessary to be successful at any early-stage company. And so, I think, if you’re looking at that big hire from a Google or a Facebook or any large company, when you’re talking through their experience and talking through the anecdotes, you move out of your swim lane and you make something happen because it’s the thing that needs to be done.

I think it’s the most important thing, because when I’ve seen folks fail to scale down — as you put it, it’s a great phrase — it’s largely [because] they’re psychologically or genuinely just reliant on the infrastructure of these large companies. And they’re good at being a functional owner, but not good at really working on the most important thing.

“If you think about what makes early-stage companies successful, it’s that everyone runs towards the fire.

Whether it’s a big opportunity or a big problem, you just have to. There’s not much room for error. And if you don’t fix it, no one will. Right? I think a mentality that you find in large companies is that people can become indoctrinated and reliant on the infrastructure of these companies.

The other thing I found, though, is you also bring people’s networks, which is really positive. You mentioned Molly, one of my closest friends, who was the chief operating officer of Quip, and is now the COO of Lambda School. We obviously came from a similar network, but actually some of the executives that Molly and I brought into Quip, like our heads of sales and marketing and other things, really helped us transform as we were maturing as a business.

Because, I think, in some ways we had a great network from Facebook and Google and my previous startup, but those were all consumer companies and — especially as we discovered product-market fit — we really needed to be a real, enterprise SaaS company.

To some degree it was both an advantage, in the sense that we made, I think, consumer-grade software at Quip, which was a huge selling point. But I think on the go-to-market side, we were learning a lot of things the hard way. Learning lessons that some grizzled veterans of enterprise software had learned 12 times before.

So I’d say another important thing, particularly for startups, is: Recognize where you have blind spots. And if you can bring in a senior leader that has done it before, that’s also compatible with your culture, you can skip a step. You can skip some learnings that other people have learned before.

And I do think that I’m a huge believer in cross-pollination of experiences producing great outcomes. I had never worked in APIs before Google Maps. I’d never worked in enterprise software before Quip. And if you have a beginner’s mind and you’re willing to learn a new domain, your naïvete can be a huge asset, too, because you see things that other people don’t.

I think it is really, really important — finding that right balance of not being too stuck in your existing network, and making sure the senior people in particular broaden the network of talent that you’re bringing into your company, and broaden their perspectives.

It’s no surprise to me I’m friends with a huge percentage of the successful founders in the Valley at this stage in my career. And when you have dinner with great folks like Patrick Collison at Stripe, 80 percent of his conversation is questions. I mean, the best founders are the most curious people in the world. If you embrace that, you’ll end up bringing in a much more diverse range of talent into your company, and you’ll really benefit from it.

Yeah. Many entrepreneurs are uncomfortable with the idea of bringing in go-to-market DNA because it’s less familiar, because they’re concerned about changing the DNA of the company. What advice would you have for them about managing that discomfort?

I may have been drinking the go-to-market Kool-Aid pretty deeply at this point. I’m at Salesforce, and I think we’re one of the best companies in the world at marketing and sales and distribution, but I think it’s a huge strategic mistake.

“Essentially, I talked to so many founders who view product-driven and sales-driven as polar opposites. And my answer is: Why not both?”

It’s interesting. If you take the greatest product-driven companies — I’ll take Slack, probably the prime example of this — the product’s wonderful and it sells itself, right? It spreads organically. The self-service purchasing process is amazing, and the onboarding process is amazing.

Slack and a number of other companies who pioneered that model have created this next generation of SaaS companies who all want to be product-driven, which is wonderful. It’s a great idea. But then, at some point, if you want to move up-market and you want to be on the minds of CIOs and CEOs outside of the early adopters, sales could be a really important part of the process.

And if your product is amazingly easy to use and spreads organically, that leads to better negative net churn; it leads to lower cost of sales. And it’s a superpower you have against companies that only focus on sales and marketing and as their distribution channel.

I think that there’s sort of a myth that it’s a choice you make that you’re either product-driven or sales-driven. I think it’s a setback. I’ve seen literally tens of companies that I think would have been more successful faster had they gotten over the philosophical hurdle of investing in sales capacity and really embraced that motion. And I do think it’s in part because of these cautionary tales of really shitty enterprise software, and people are like, “OK, that’s what sales-driven leads to.” And I’m like, “Well, that’s a choice.” And I do think that’s the next generation of companies.

I think Stewart did a great job of this at Slack, as an example. It’s, in my mind, the prime example of a product-driven company but [also] a great sales leadership team that’s now, I think, a great part of Salesforce.

I think the answer should be both. I do think that it is hard. What I’ve observed, and I certainly am guilty as charged, too: If you come from a product background, like I did, how do you identify great sales leadership? Sales culture is very different from the culture of your product and engineering team. But that’s part of growing up as a founder.

And what I would say is: If you’re not going to do it, your competitors are going to do it, and they’re going to grow faster than you are. And if you found product-market fit and you want to have the biggest impact, don’t shy away from hard problems. I would say this is probably the biggest opportunity I see from a lot of — particularly early-stage — SaaS companies.

Well, I’m super excited to hear you say that. First of all, that’s a very compelling message of: If you don’t do it, your competitors will. And, second, I’ve personally taken a career bet at Greylock in terms of backing extraordinary teams building products that I think are the best, and the best experiences. And through the Greylock network and our community, helping them add the DNA that they can grow up as businesses and be winning businesses.


But I’d say, it is a challenge, right, and it’s a process. Let’s talk about Salesforce. Obviously, you guys work with businesses and organizations across every industry vertical in their digital transformation. You cover a huge amount of surface area.

You talked about being obsessed with social, or thinking about developer platforms and being obsessed with social, and then thinking about mobile. Those are really big changes, and a strong focus for you. What’s important to you now at Salesforce now?

Yeah. As you said, Salesforce is really unique in the sense it serves such a broad market at this point. Our core platform, we call it Customer 360, is basically a platform for digital sales, digital customer service, digital marketing, and e-commerce. And then we have a platform underneath all of that we also sell, and we’ve complemented that with a number of big acquisitions, which you mentioned at the beginning of this conversation.

So: MuleSoft, which is an integration platform. Tableau, which is an analytics and visualization platform. And Slack, which I presume everybody knows who’s listening right now, given the audience.

It’s a really fun time for us because, as hard as this pandemic has been for everyone in the world, I think it’s really accelerated every company’s investment in digital technologies.

If you weren’t thinking about self-service and chat bots for support, you are now. If you were a consumer goods company who hadn’t yet gone direct to consumer, you are now. If you’re a sales team who’s not thinking about, “OK, should we sell over Slack Connect and Zoom?” you probably are now, because you’re all stuck at your house.

So, to some degree, what we’re really focused on is: How do we be a trusted digital advisor to all of our customers — who are going through these times, that are [making] really uncomfortably fast digital transformations — with our platform? That’s the landscape of Salesforce, and we’re really focused on all of those different lines of businesses and industries.

But the big bet we made this past year was acquiring Slack. That’s really what I’m focused on right now: making that successful.

It’s interesting. I think at the beginning of the pandemic, there were a lot of people talking about things like Zoom fatigue. I think it’s, in part, because we didn’t really transform ourselves. We kind of translated the old world into the new: We took every meeting in a conference room and moved it to a video-conference room. And of course, staring at your own face all day, sitting in one seat, barely able to get a glass of water or go to the bathroom. You’re going to feel exhausted by the end of the day.

When I talk to entrepreneurs like Matt Mullenweg of WordPress, who have been running distributed companies since before it was cool, they’ll talk a lot about things like asynchronous work. And they’ll talk about all the freedoms that a distributed workforce affords.

I think the bet on Slack is really about that future — that this isn’t a pandemic behavior. We’re 18 months into it with all these variants. And the great relocation and the great resignation going on right now: Clearly, flexible work is here to stay. And we want to be a part of defining what that future of work looks like.

Stewart [Butterfield] has this amazing phrase that we’ve embraced wholeheartedly, called the “digital HQ.” I love it because, especially as an entrepreneur, the most fun thing was choosing my office. I remember finding the abandoned warehouse in Mountain View for FriendFeed, and I remember finding the office above the Warfield Building in San Francisco for Quip.

And you have to think, now: If you were starting a company today, you wouldn’t start with choosing your office space, you’d start with building your digital HQ.

What are the tools and technologies that you use to connect your employees, because you’re not together most of the time? And we’re saying: OK, well, how can we take Customer 360 into this vision for a digital HQ and make it help every company in the world go through this transformation? And that’s pretty fun. It’s a fun vantage point right now, too, as someone who’s entrepreneurial, but obviously [has] embraced the other side of my leadership.

And it’s an amazing opportunity working with Stewart; he’s someone I’ve admired for a really long time. When I was at FriendFeed, he was working on Flick. I’ve known him for like a decade now. It kind of feels just like an amazing opportunity to work with someone who I’ve been really close with for a long time.

It sounds like fun to both work with people that you think are talented, and that have a strategic impact on what you’re trying to do with Salesforce strategy. There’s part of your brain that’s focused on that, and then part that’s segmented toward the other parts of M&A and growth for Salesforce. What was significant about MuleSoft and Tableau?

Marc [Benioff] has this phrase that I’ve really embraced, which is, “Have a beginner’s mind.” And one that’s not his phrase — but he says it more than any technology executive that I’ve heard, and I’ve really embraced it — is, “Wake up every morning and try to forget what you think you know. Look at the world through the lens of a beginner’s mind.” And with our M&A strategy, it’s really recognizing that great innovation can come from anywhere.

Just a quick anecdote — it’s not lost to me that Google, when we moved from the office in Mountain View to our first campus, it was Silicon Graphics’s old campus, because they were going out of business. And Facebook, we moved from Palo Alto to our office in Menlo Park, it was Sun Microsystems’s old campus because they went out of business.

And it was interesting: Like every campus I’ve ever moved into, it was a graveyard of a dead technology company that basically failed to transform because the world moved on from where they were. It’s so easy on the outside to say, Why didn’t they see that this change was happening? Why didn’t they embrace it? The classic innovator’s dilemma.

The answer is interesting. I found, culturally, having been on the inside and on the outside of the disruptor and the incumbent, you end up with sort of this myopia where the narrative — when you have tens of thousands of employees — the narrative from your colleagues becomes louder than the narrative from your customers.

I remember, a while ago, being on Microsoft’s campus and seeing everyone carrying around Windows phones. It was a long time ago. Everyone I talked to was convinced that the Windows phone was going to be successful. You walk like one foot outside the campus and it was like: No, there’s no way. But it’s interesting, because you end up with this sort of reality distortion field.

I give a lot of credit to Marc Benioff’s own philosophy and personality here. And certainly something that I embrace is that: we have a great venture’s arm, we have a great partner ecosystem, and we’re always looking for great ideas, in Silicon Valley and elsewhere around us.

If we see something that is adjacent to where we are, our customers are benefited, and, most importantly, where one plus one does equal more than two — if we combined it with our platform, we could do something greater — of course we’re going to do that. Because we’re led by our customers, and we don’t have the arrogance to think that innovation only can happen at Salesforce.

MuleSoft is a great example of that. This is an API-led integration platform, but the way we found it was through our customers. Every time we were in a service cloud deployment, MuleSoft was the tool that the IT department had chosen to integrate with the ERP system or whatever it was.

We were like, What is this MuleSoft thing? And why is it so popular? We got to know them, and we were like, Wow, this is amazing. Maybe we should shop to our customers saying, “Hey, we’re going to help make integration part of our value proposition,” rather than “You have to figure it out yourself.” And it’s been a huge success. We just had our investor day last week after Dreamforce. And, I mean, it was one of those things, looking at the revenue growth since we acquired it — it’s amazing.

Not so simple.

I’m so proud of it. But I think it shows that having a beginner’s mind about innovation is a huge part of our company. It’s interesting too, because Marc is obviously an entrepreneur and head of product. David Schmaier is an entrepreneur. I’m an entrepreneur. We’re a company of entrepreneurs. It’s a huge part of our DNA.

How do you prevent that distortion field that you talked about, because Salesforce is a large company now? You could stay in the, I don’t know, in the “Slack of Salesforce” all the time and never exit and only hear that opinion.

It’s a huge challenge. I mean, especially, one of the things I’ve observed from people who are new managers — and particularly founders and CEOs whose teams are growing — is not knowing how and when to delegate and what to delegate. And you’ll see polar opposites. You’ll see people who essentially micromanage every decision and don’t know how to really empower and bring on leaders. You also see the opposite, though, where people will delegate too much. You can end up with fires burning that you don’t know about. And it’s a real skill.

I think the best way — and I’m speaking, probably, to your B2B audience right now — is to spend time with the customers.

I mean, it’s not that hard. If you want to know if your product is starting to develop warts, you’ll hear it if you’re talking to your customers. If you want to know that there’s a competitor creeping up on you, you’ll hear it from your customers. If you want to know that there’s an adjacent product that’s really valuable, that’s always being used in conjunction with your product and might represent an M&A opportunity, you’ll hear it from your customers. Last quarter alone, I had 70 C-level customer meetings.

Oh my goodness.

Yeah, in one quarter. It’s just a huge part of developing a successful business: Are you truly obsessed with your customers? Or is that something you put on a poster in the cafeteria? Not that there are posters or cafeterias anymore.

“If you end up focused — navel-gazing — on your own organization and you’re not out talking to the people you’re actually serving, your customers, I don’t think you’re doing your job.”

It’s a great way to see things early. And, also, it can be a really great reality check about your internal narratives and what’s actually going on.

So, because you’re also a consumer guy and half our audience is B2C — and, actually, the lines are less clear than they used to be, right?

I still have the vote of outsiders. I still keep some street cred there.

You’ve definitely got street cred there. What advice would you have for companies trying to remain user-centric on the consumer side?

It’s much more of an art form, because obviously you can’t talk to tens of millions of people every single day. So it’s a different thing.

Actually, Reid Hoffman gave me great advice here, which is — I think what I often see from consumer companies is: you know what you want to achieve when you’re at scale, but the hard part is getting to that scale and really recognizing the different milestones that you need to overcome to get to that point.

Facebook, I think, did this really well, where it started off as a service for universities. It expanded sort of iteratively beyond that. And I remember every stage was controversial: when we let in, or when we expanded to, the parents, that was a huge controversial thing. We let everyone in.

But even after that point, our growth team would focus on individual countries, and having maturity models, and really recognizing in every stage where we were: What are we doing at that point?

If you have three friends on Facebook, you’re doing a different job than if you’ve got thousands and you’ve been a member of the network for years. It was, like: Really have a strong point of view about what stage of your growth curve you’re on, what jobs you’re being hired for at that point, and recognizing your different cohorts of users are probably at different stages of maturity as well.

And there are a couple of failure modes that are common. One is you just never find that sort of moment to reach scale with consumer services. The other that you see, time and time again, is you become an “it” company for a couple of weeks, but your platform sort of buckles under that pressure, and you end up not really having seen the flywheel take off.

That moment is the most nuanced — where I think people end up embracing top-line vanity metrics and, often, losing sight of really durable consumer growth.

And so, the one thing I’d say is: Have a strong perspective on what those aha moments for your consumers are, and become relentlessly focused on those. Don’t get distracted by the top-line vanity metrics because — I mean, you as an investor know better than I. There’s just a graveyard of companies that hit a lot of top-line metrics, but don’t actually get that durable flywheel of attraction that comes from being much more opinionated about why people are using your service in the first place.

Both those graveyards are large, right? Of extraordinary products that didn’t get the flywheel going, and then extraordinary products that for a hot second were incredibly interesting and caught consumer attention. These are amazingly difficult things to do — to create a habitual product.

When you talk to great consumer founders — just take people like Jack Dorsey — you’ll hear the depth of their opinions about the services that they’re making. And I think that really reflects that kind of real intentionality about why their services are important. I remember being mystified in the early days of Snapchat, and all the decisions Evan was making, that turned out to be so impressive and so smart.

I think that discipline is really important as you’re scaling your service, because, as you scale it, you know how you stand apart from the crowd of adjacent competitors in that space — which is going to be a lot of them. It comes down to having a really strong perspective about What are your services and why?, and staying in that swim lane and being disciplined as you go through those growth moments.

Speaking of distinct points of view, I remember being at dinner with Evan Moore and some friends a decade ago and him talking about the importance of ephemerality and how it would change interaction completely between people — this is a very different idea a decade ago — and thinking, like, man, this guy’s a weird, weird thinker. But it’s distinct, as a point of view, as you said. And it was deeply held and deeply thoughtful.

So one question that I think is a little bit taboo for entrepreneurs is how to think about acquisitions. You’ve been on both sides. What advice, and as you said, painfully and less painfully: What advice would you have for people who are navigating that, or looking at a set of options, or deciding: Do I explore that path?

I sort of gave you my background, but [with] FriendFeed, we were for sale, [and] we sold our company in that case. And then with Quip, we were bought. We had actually just raised our Series B from Greylock, and we were definitely not for sale — it was just a different model.

Between Facebook and Salesforce, I’ve acquired as many companies as probably most people who are with me at this stage, just because we’re so inquisitive at both firms.

So I’ll tell you that there’s a lot of advice out here on this. I’ll answer [the question of] Should you consider it? I think it’s important to consider, but consider it quickly.

I’ll just take Quip as an example. We had been pursued a number of times in Quip’s history. Often I would either not engage, or have one conversation and be very clear about, like, “No, now’s not the right time.” I think it’s important to always know the market landscape, because if something changes in your business, the relationships that you’ve developed prior to the moment where you might be open-minded to acquisitions matter.

I think there’s a point of view of: It’s a distraction; don’t engage in the conversation. That’s right, by the way. But it doesn’t mean you shouldn’t be polite, develop those relationships, and then just say no and move on. Because at the point where it is relevant, you want to have a conversation you can pick back up. You want the relationship to have existed there. And I don’t think these conversations hurt.

I think it’s important to be realistic that not every company is going to end up [as an] at-scale public company. As much as that’s every entrepreneur’s dream, it’s not every entrepreneur’s outcome. And so, you should just recognize that, and make sure that you’re not arrogant in that respect.

I do think though that you can end up in casual conversations with large companies indefinitely. So, if you aren’t firm about where you are, you could end up with a huge, distracted process and it can be insidious. It can infect your brain a little bit. It will make you less confident in your organic path. And it can also mean you’re not working on growing your product, your customer base, or your team, which is what you should be working on.

If you do get to the point where you’re thinking that an acquisition is where you want to go, I think it’s important to have good advice — and I think it’s important to have advice outside of your investors, too. And [that’s] not in any way a knock on Greylock or Benchmark, the firms I’ve worked with a lot in the past.

But your investors have a portfolio of acquisitions, so I think, in general, we’ll have a difference. Your incentives are aligned, but not 100-percent aligned. Put another way: If there’s a 10-percent chance you’re worth billions of dollars, your investors would probably take that chance. Whereas, if you have a 90% chance at $300 million, $400 million, from whatever you’re considering, you might take that because the certainty may be worth more to you than it is to your investors.

So, whether it’s your attorney [or] entrepreneurs, what I recommend, as someone who’s been in the game before and done it, is to have a trusted advisor outside of your board that can give you advice that’s from an independent vantage point as you’re considering the strategic outcomes.

And then, the last thing is: the process matters. Probably too much for this conversation, unless you want to go there. But I’ve seen a lot of people screw these up and overthink it or under-think it. I think there’s definitely an art form to deal making, and I’ve been on both sides and seen a lot of things go well and go poorly. So I think, really, just make sure you have people who have done this before around you. And make sure that if you’re going down this process you can end up with material changes in valuation, material changes in just the likelihood these things close.

And there’s a lot more — no one writes about the acquisitions that didn’t happen — but there’s a big graveyard of those as well. I’ve just seen some really crappy advice, and entrepreneurs somewhat surprisingly following really bad advice. Find the right people as you’re considering it, and find the right mentors.

As someone who’s been part of several acquisitions, good and broken, that all resonates in scores with me.

You’ve said that Salesforce had a very [good] in-office culture prior to the pandemic, and you’re clearly a believer in hybrid work as here-to-stay, now. As somebody who’s attended Dreamforce that’s also uniquely an in-person experience, with a lot of moving pieces.

For you as a leader and for Salesforce, what are you changing and learning?

Yeah. It’s crazy. This past year, just for context, we’re at about 65,000 employees, and we’ve onboarded 20,000 people since the pandemic started — none of whom have ever been in a Salesforce office.

We typically have 200,000 people show up for Dreamforces — everyone who lives in San Francisco knows because of the traffic. We had a digital Dreamforce last year. This year we had a hybrid Dreamforce, and we had about 1,000 people in person, but 100-million-plus people watched online, which is really great.

And so, as you said, we’re famous. I joke that half the people who aren’t in tech have no idea what Salesforce does except for our towers. We’re known for our towers; we’re known for our events. And so, we’ve gone through digital transformation ourselves.

I’ll tell you, we’re really trying to embrace it. I believe the companies that will thrive on the other side of the pandemic in this all-digital work-anywhere world are the companies that really lean into the changes from this past year. Because I think what’s driving the great relocation and great resignation is just — we have this free market of flexibility that employees are now thinking: Where do I want to live? What type of company do I work for? What type of flexibility will that afford?

It’s obviously a moment in time, but I think it really reflects how permanent these changes are. So we’re really leaning into flexible work as a future.

I mean, just as one example: Every team at Salesforce has a flex team agreement where you say: What days are we going to be in the office? What days aren’t we? Part of choosing your team at Salesforce is: What is the working style? And there’s like a free market of that.

For Dreamforce, we had 1,000 people in person. Most people experienced it online. We launched a streaming service called Salesforce+. You don’t get the latest episodes of “Ted Lasso,” but you’ll get a bunch of content for CMOs and chief digital officers. And so, it’s pretty cool.

We really leaned into this change. I have a strong thesis. Obviously, we made a $28 billion bet on Slack on this thesis:

“I think this is the beginning of distributed work. And the pandemic is not the era of distributed work. I think the pandemic is the seed that got planted that will define the next generation of white-collar information work.”

And I think if you look at the history of Silicon Valley and just the influence, for example, that Hewlett Packard had on the earliest days of the office culture of tech companies, and what Google had and what Facebook did with the open office floor plan — we now have every company in every country in the world doing this experiment on working digitally. And you have to know, just intellectually, we’re not going back.

But I think the real opportunity is we still don’t know what it’s going to be like when it’s not imposed on us for health reasons. What is the true world of flexible work when you can choose to be in person and how you’d be in person? I think the entrepreneurs who predict that future — and build the tools and technologies to make companies successful in that new normal — I think there’s a huge opportunity there that, obviously, we’re investing in, but I think there’ll be multiple billion-dollar companies created to make companies successful in this new normal.

It’s actually just a really exciting time from a product- or a life-configuration perspective, because there’s never been such openness to rethinking it. And it’s not just openness — it’s demand, right? I’m sure you see from Salesforce employees, you see in all our companies: The genie is not going back in the bottle.


This is a time where there’s increasing polarization across political, social, economic issues. Salesforce, unlike many companies, is quite outspoken here. How do you decide as a company what to be outspoken about?

Yeah. One of the things that’s always been a part of Salesforce company culture, long before I arrived at the company, was that Salesforce has always been a values-driven company. Our values are more important than our mission. And it’s always been that way.

Marc and Parker, when they created the company, started the 1-1-1 model where 1 percent of the company’s equity, employee time, and software went to nonprofits and educational institutions, which has become a model that a lot of companies have adopted.

I encourage everyone online to adopt that model, too, because it’s easy when your company is not worth a lot. And by the time you go public, if you haven’t set up this infrastructure to give back, it’s a really challenging financial decision.

I think, fundamentally, there’s an area where I disagree with some very vocal CEOs and entrepreneurs out there. The idea that your business is there just to build a product to me is not true. Business is a huge part of our culture and our society. We believe in stakeholder capitalism — that our business isn’t here just to serve our shareholders, it’s here to serve our employees, our communities. It’s why every senior vice president and above at Salesforce has to sponsor a local middle school. We don’t want to be the tech company that’s here to extract value from our communities. We want to be a tech company that’s there, that makes our communities better.

And you can see it. If you just look at the headlines right now, tech is beyond being like, Oh, cool, when’s the next iPhone coming out? It’s people worried about job displacement with things like automation and intelligence. People are worried about the impact of tech and communities and rising real estate prices. And you can sit there and resent it, or you can recognize that this is what it means to be a part of a society and lean into that.

Similarly, if you look at — particularly younger — employees, when they choose where they work, the values matter. This is where you spend a huge percentage of your time, particularly at a startup. And if you think you can be there and only talk about your product, fine.

But, speaking of your competitors, they show up and say: This is a place where you can actually grow as a person and identify with the values and give back. That’s a more competitive position, particularly for employees that want to derive meaning from their work, which is a very important part of choosing where you want to have an impact on the world.

We lead with our values. That starts with trust and that means developing trust with our customers, with our employees, with our communities. And it also means that we stand up for our employees. So now somewhat famously, our policy around offering relocation expenses to people that wanted to leave Texas became public. The algorithm, if you will, is simple, which is that: Our employees are at risk, and if they are, we’re going to stand up for them. And I think it’s one of the things that makes Salesforce a great company.

I hope more companies follow that path, Bret, that you and Marc and others at Salesforce are charging ahead on.

We’ll end on something more personal. This last 18 months has been an era of exploration and learning for all of us. What did you discover about yourself or your work style or anything else trapped in your house?

That’s a great question. I’ve realized how important in-person interactions are. I remember the first time we got together as a management team, [with] a lot of PCR tests going into it, and this sense of almost euphoria when we finally got together.

It was interesting, because I was both realizing how efficient things are — I have three kids under the age of 12, and it’s been so amazing to spend more time with them and have family dinners every night and spend less time on the road — but it’s also made me realize, as we work in this new digital forum, just how important those in-person interactions are. And, I don’t know. I obviously knew that, but the actual emotional response when we all reconnected was like — it felt just like oxygen.

That made me reflect on myself a little bit. I’m the classic introvert in some ways, like many tech folks are. But it made me realize that I don’t really know what this new normal is going to be like — What is the right balance between in-person and digital? — and I’m also reflecting to myself, that you really need to balance it. That’s probably what I learned.

That resonates. I feel a little bit like, What do I want? Because not driving to East Bay for an hour-long meeting is a real joy. But we definitely have been starting to do hybrid partner meetings, and it’s a different experience. It’s great to see colleagues.

Beyond Slack, what’s an experience or an interaction — you’re an interaction guy — that you can picture in the future that you think is going to be different and better than what we have today?

I think we’ve under-invested in new, asynchronous workflows.

One of the features that Slack just introduced, which is called Clips, is asynchronous video, so it can replace the morning stand-up. I mentioned Matt Mullenweg is a close friend of mine, and Automatic, which makes WordPress. Their whole culture is focused on asynchronous.

And obviously, at Quip, we invested a lot in documents. I remember, for our board meetings, we would use documents rather than slides. And part of the culture of the Quip board meeting was everyone would read the board document — but actually comment digitally, inside the Quip document. And the actual board meeting was a strategic discussion.

All the numbers, all the product announcements: everything had been read, commented. None of the tactical stuff was in there. And it meant we’d have — I don’t know, John Lilly could tell you — only a few hour board meeting. But it’d be the densest strategic discussion ever because all the tactical stuff was done.

So when I look at the future of work, as I think a lot of people have been, I’ve seen a lot of stuff around virtual reality, and I’ve seen a lot of stuff around in-person sort-of video experiences. And I think that’s all great. There’s probably some real innovation to be had there.

But when I think about the opportunities of distributed work and digital work, it’s: Can you be productive across time zones? Can you enable people to have more flexibility and freedom, which means you can consume information on your own time rather than in real-time? I know it’s a huge area of investment for Slack, but it’s clear that there’s just tons of investment here.

If you just look at the percentage of your time you spend in meetings — or if you don’t, you’re probably at a very small company — at most companies of scale, you end up on this treadmill of synchronous meetings. I think there’s a real opportunity to innovate and enable here.

I think asynchronous communication and collaboration unlocks a lot of the value of flexible work, because it translates to flexibility for individuals and translates to more flexibility about where and how you hire, which I think are the big levers for the future of distributed work.

And then if you figure it out, the other big trend is: How do you actually transform cultures to get there? There are lots of great ideas that, if you started from day one with this company culture, it’s easy to adopt. And the harder part of that, and particularly in the future of work and enterprise software, is the change management.

I think that where the magic is going to be in terms of investment is new modes of asynchronous work. And then the product itself helps people onboard to that new experience. I think is going to be a bit of an art form and a real huge opportunity

Bret, we’re out of time. Thank you so much for being here and sharing with us.

Thank you, Sarah.