Joining Facebook

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Alex Kracov: So I'd love to start with your time at Meta, which was Facebook when you joined. I think you joined as the Group Director for Global Marketing Solutions. How did you get that job, and what was the role when you first started?

Rich Liu: Yeah, that's a great question. I often wonder how I got that job myself. I started my training as an engineer. I spent about eight years in financial services building out sales operations, services teams. But I really wanted to break into tech. I loved Facebook as a user, and I had no idea how to convince them to hire me for a sales or a customer-facing account management success role. So I basically figured out, oh, there's a big project that they're leading around segmenting and tearing the ads business. This was one of the first times they were doing this restructuring of the business org.

I had been at this investment shop while it was scaling from about 300 people to maybe 1,500, a couple 1,000. Based on my experience there, I had a lot of just stories to tell about how I had helped bring different innovations into the sales team — how do we restructure the hours of an inside sales team so they're maximizing time when they're going to reach people on the phone based on the data we have, how do we restructure sales support so we're regionalizing reps, regionalizing support versus doing one-to-one, how do we go recut, how we distribute inbound leads or appointments set to people to minimize drive times.

All these kinds of things that I was able to convince them that I could help solve and drive some of these projects around segmentation, that was really my first job there. Going in helping to lead a cross-functional project to basically decide what are the guardrails between what is field sales, sort of inside, outside sales versus online sales, how do we define what gets what treatment, bringing together all the teams in the different segments and the different functions to go implement this different strategy for how we were going to cover our account. And so that was really my foot in the door that led to running account management teams, and later sales teams.

Alex Kracov: Was that something you advocated, or were you sort of hired to do that specifically? Like, Sheryl Sandberg was like, "All right. We need to restructure and sort of split up the business in this way." How did that all work?

Rich Liu: Yeah, funny enough, my wife had worked in Sheryl and David Fischer's org at Google way back in earlier years. And so I managed to finagle an introduction that was bounced around, across Sheryl to David, to Grady Burnett. It was sort of one of those true startup stories where you're like, "Hey, you've talked to a bunch of people. You seem like you got a good head on your shoulders. We can't hire you to go run sales teams because we can easily go hire 50 of you out of Google to go run ad sales teams. But why don't you come in, and we'll figure it out?"

I remember Alexa Pope was my hiring manager, another ex-Googler. She brought me in and basically said, "Well, we have this project. Can you just help drive it for the next few months? Then we'll see what happens." Basically, I was just excited to get my foot in the door and work across the aisle. I said, "Great. Send that shit to me. We'll figure out what happens." That was really it. Sort of that classic when you're able to find a rocketship, as Sheryl says, find whatever seat you can get and go from there.

Early go-to-market at Facebook

Alex Kracov: What was Facebook like at the time? Because it was pre-IPO, right? It's still just trying to figure out a business model, right? There's clearly an insane growth on the consumer side. But you were trying to figure out, okay, how do we actually make this go-to-market? How do we actually make money from all the growth, right?

Rich Liu: Yeah, I came in 2010. At the time, they were already maybe 1,500, over 1,000 employees easily. There was already an ads business there at the time. It was very, the biggest advertisers weren't P&G, or Nike, or Walmart. It was like Zynga and Groupon and some of these dating advertisers. So it's not the sort of world-class brand platform that we think about today. It was actually driving a lot of game installs and app downloads. That was actually where the meat potatoes were. And so, at the time, we were really looking to sort of legitimize social media and, eventually, mobile as places where advertisers needed to spend their TV dollars, not the test dollars or a couple $1,000 here and there. That was really a lot of the big journey that we were on as an advertising platform, as a publisher — to legitimize it as not just the test thing, moving from sort of early adopters to the mainstream of marketing. That was really the four years I was there. And so it was a really cool adventure and experience to be able to see how we were able to drive that transition and how people thought it would drive adoption so that we wouldn't get left out of CMO's offices, but they would actually be looking to work with us.

Facebook in the 2012 US presidential election

Alex Kracov: Really interesting. I think you were — I don't know if you're responsible for it, but you sort of ran Facebook's go-to-market for the 2012 US presidential election. I think that was that really famous election where Obama obviously won for the second time. But it was famous for using digital channels to mobilize online communities. What was that like building up the analytical book of business for Facebook?

Rich Liu: First of all, I'm not a politics person. I'm not a DC person. And so that was a really eye-opening experience for me on a personal level, not just a professional level. The manager on my team that led that effort, AJ Tennant — who's now at Glean, by the way. Awesome sales leader — we were sort of tasked with trying to figure out, okay, in the 2008 election, we had 0% of online ad spend. It was sort of an experimental platform. Now in 2012, Facebook was very much in the mainstream. How do we go from basically having a fledgling team that was servicing some of these emerging advertisers, the campaigns, the super PACs, the different organizations, to as quickly as possible spooling up in order to capture as much of the online ad spend as we could during the election?

And so it was very much that startup within a larger company mindset. All right. We have this objective. We have a limited amount of time. What do we do? And so a huge credit to AJ and the sales leadership team and success leadership team working closely with Mariel Lean, Joel Kaplan's public policy sort of DC folks, just surrounding and figuring out, all right, well, let's take a look at this election cycle. We have a year, year and a half to go after it. Who are going to be the biggest spenders? The campaign's themselves, Romney, Obama, and obviously, the smaller folks that didn't make it to the final. The outside spending, the different organizations, let's figure out how we want to staff those orgs from a high-touch mode embedded at Obama for America offices in Chicago. Where are we going to support them in more of a sort of slightly more scaled model? Where are we going to play the inbound game of, okay, let's see how many of these state races, these down-ballot races we can capture through a broader classical inbound online sales model?

We put together a team and what was probably the course of a few short months to really tackle. You have to segment the right and left wing, because we don't want the same folks servicing both sides for trust reasons and also sort of privacy reasons, right? We got to segment between the size of account and potential size of account and how much touch we would put on then. We had to segment between the end customers and their digital agencies or ad agencies, and figure out how we were going to cover those. And what were the collection of people who knew politics and who knew the campaigns, and the people that actually know advertising and know digital and know social media? And trying to construct a high-functioning team that would actually work across all those different aisles.

We were able to go from capturing less than 1% of digital ad spend in the '08 election to something about 20% of digital ad spend in the 2012 election. So it was a really cool win of how the team came together really quickly, really solved for let's forget the functional lines. Let's forget the department lines, and just put together an effort to go capture this thing. It was a really cool story. Obviously, at that time, we were a little dense to some of the broader issues that were posed around bad actors and the ways that they could exploit the algorithm in Facebook. I don't talk about that era too much. But at the time, there were some really cool stories about how we help people find their voice. Obviously, looking back, it's a little more complex in the history.

Customer segmentation at Facebook

Alex Kracov: It's a great story when it comes to just go-to-market segmentation and focusing on specific segments. Because if you didn't sort of wake up and think, all right, there's a business when it comes to political ad spend, I don't think you would have — if you didn't structure the team in that way, you wouldn't have captured that opportunity. You can see that story as you go through different industries, whether it's the automotive industry or just going to convince B2B companies to start spending money on Facebook. So yeah, I know. Because at Lattice, in the early days, segmentation was huge for us when it was just like SMB mid-market and enterprise. So yeah, that's a good experience.

Rich Liu: I know Dini recently did share some of those early Lattice stories. So really awesome to hear how you all approached it in the early days. Because you've got to start somewhere. And it's always a matter of trying to figure out, do we go industry first, or region first, or size first, and which of those are going to come from first?

Alex Kracov: Yeah, absolutely. And so, "Move fast and break things" is obviously the famous motto at Facebook. Everyone knows that one. Did you have a favorite experiment that you ran during your time at Facebook? Was there anything that sucked up?

Rich Liu: Yeah, absolutely. So many. The funny part about that one was, in the early days, it was sort of this radical 'don't be afraid to break things,' which I mentioned in a recent podcast around how that was a really empowering culture. Like, you don't have to be a senior leader. You don't have to be some kind of a department head or manager to just come up with good ideas and execute against them. I really just love that era and that culture that I know Mark is working to bring back.

One of the interesting things when we were doing this original segmentation exercise, I still remember it was called ASTS. It was about — the classic thing would be, let's go get the biggest spenders and put them with the highest power, most-experienced sales and account management people. But in our industry, we realized, well, hold on. The most high-powered or high-spending advertisers and clients at the time weren't the PNGs and Walmarts and Nikes, and fill in the blanks. They were the folks like Zynga, and LivingSocial, or Groupon, or some of these performance advertisers. The classic thing would have been, "Okay. We'll put them with the high-touch reps who are going to take the most care of them," except when you think about traditional advertising, those folks don't need a really cool creative program. They don't need to go to Super Bowl games or being taken out to steak dinners. They need a great access to the platform. They needed optimization from account managers who knew how to go drive efficient installs of apps on the platform.

Funny enough, we actually started realizing, hold on, it's not about putting the biggest advertisers just with the most experienced sales reps. Segmentation is not just about the dollars. It was about, oh, what is the specialization of this mid-market org, this inside, outside, call it national sales org, that was really good at working in certain core competencies that were not the traditional media sales reps. And so we actually decided to profile some of these accounts differently rather than just pure spend, which in a lot of worlds is not what you would expect out of a segmentation exercise. It ended up working really well. Because that team that had the specialization of how to optimize business, how to account manage, how to work across Facebook to the platform org, to the product org, to build the right ad units, to make sure they had the right API access, that team really unlocked the potential of those clients and those advertisers in a way that the classical ad sales rep simply wasn't going to be able to do.

So that was a really cool experiment that I think was well-founded. Obviously, over time, we had to be smart around. Well, that served us well. But as we built more vertical expertise, as we built more industry expertise, to have the confidence to say, "Hey, you know what? We're going to go recut and re-segment based off industry's first, not based off of these service-level capabilities of the teams, because we wanted to push ourselves to build that expertise, to build that specialization of how different industries should be leveraging the platform." And so even before we truly had, this is the right narrative and automaker should be using on the platform. This is the right narrative that a B2B software company like SalesForce should be using on the platform, as soon as we started having those semblances of expertise and learnings and best practices, we created a bold bet and said, "Let's go after this and see if we can segment, and therefore challenge ourselves to build better vertical offerings," which I think ended up happening but was really scary at the time.

Alex Kracov: Yeah, it's an amazing story. Because I feel like for Facebook, building up this go-to-market function, the incentives are so aligned with the platform and the advertisers. The more that the advertisers see success on the platform, the more money they're spending. And so it's really interesting to hear as you build up the expertise and you educate the users, they get more results. So they spend more money. It's a win-win for everybody. They're happy. They're acquiring more people. Facebook is happy because they're spending more ad dollars. So it's really an interesting story.

Selling through Facebook's rocky IPO

Alex Kracov: You were at Facebook during the IPO. I remember at the IPO, there was a lot of question marks around whether Facebook could take advantage of the shift to mobile. I'm curious what it was like working at the company at the time. How were you able to sort of take advantage of that shift in retrospect?

Rich Liu: Yeah, it felt scary at the time, but it was like the classic. We talked about the ups and downs of the startup roller coaster. Even though the company was about several 1,000 people at the time, it was really scary. It was scary because we had been a private company. And I, for one, actually appreciated a lot of elements of the culture Mark created around competitiveness, around conquest and this mission that we're on, and really enrolling the employees at the time to go work for something bigger and towards something bigger than just ourselves — the idea of opening the world and connecting people.

But at the time of the IPO, we were so excited. We did this hackathon. We were shipping all sorts of stuff. We were up all night before the button press on Hacker Square. I remember shortly thereafter, we all sort of thought, "Oh, the company is so great. We're going to go up. It's just going to be up into the right." Sure enough, I think within the first day or two, yes, there was a trading glitch or whatnot. But it quickly went to, well, the stock price is down by a half or more. All of a sudden, for all the good work we thought we were doing, it felt bad to be judged by the outside world. "Hey, you might think you're amazing. But we think you're actually half as good as you say you are." And by the way, you have this existential threat of, "We don't believe that you can manage the shift to mobile, that you yourself has said is inevitable for the future lives." All of a sudden, there was this delta between what we believe in ourselves and what the outside world saw in us. And so there was a real tough dealing. There were people that left. There were people that felt like, "Oh, wow. It doesn't feel like we're winning anymore." All of a sudden, maybe the shine has worn off.

But real credit to Mark, Sheryl, and the leadership team for acknowledging that and saying, "You know what? We've heard that. We know what we're building. We do need to accelerate our mobile ads, our mobile monetization strategy," which was already there and already in motion. But that was something where we had to deliver against, and we had to ship the product against that. We had to keep the advertisers and clients engaged while we were doing that, and find the appropriate level of selling the future and helping them build for the future that we knew was coming, yet not lose patience because it wasn't there yet and call us charlatans. And so there was this mix of reaffirming commitment to: one, do you believe in the mission? Two, do you believe in the team's direction and the ability to ship? Three, do we believe in the future that we've said is going to happen, of this massive drive to mobile, and that's where the future is going to be, worn or lost, is real? If so, then we need to be able to tune out the outsiders and be able to say, "Let's go take care of our business and go grow, and then see what happens."

I certainly know and have felt that feeling of hoping and believing most days but certainly having that inside doubt. Sometimes we're out in front of the customer saying, "Yes, this is the world that will play out. Yes, this is why we believe in it. This is the product we're building. And yes, while we have a black eye in the stock market with our stock price, we firmly believe that we're building a quality product and a quality business. You need to be on board." It's funny that experiences like that really build camaraderie. They really build resilience. They really build commitment. Because everybody has looked inside and had to make that active decision to be a part of it and to stay and actually carry that water forward.

Transitioning to B2B sales at MuleSoft

Alex Kracov: I love it. Thank you for sharing that story. And so after Facebook, you went to work at MuleSoft, which is a very different business than Facebook, right? It's B2B. It's a technical product. What made you make the switch to B2B?

Rich Liu: I think the only similarity is probably they both have blue and white in the logo. It pretty much stops there. When I went into Facebook, the goal was to break into tech. And if you don't work in tech, sometimes that word 'tech' means so many things, right? It means some company that some investor or analyst has said is a tech company. Meaning, they do something with technology or software or something or other. I didn't know the difference really between a publisher, an ads online media company versus a software company, versus SaaS. I was actually very much of a neophyte.

But over my time at Facebook, I started to realize, partially by having the tech industry vertical as one of the teams that I work with and I work closely with, as I started to learn about that industry seeing, oh, there's consumer. There's B2B. There's hardware. There's software. There's infrastructure versus more sort of surface of the enterprise applications. There were all these different flavors that started to emerge. But one thing was really clear was that, a lot of what we think about when we say the tech industry isn't Facebook, or Google, or these consumer products that we use. It's actually a lot of B2B software and SaaS companies, right? Particularly, as a go-to-market person, as an operator, a lot of building organizations to go drive, at the end of the day, distribution — whether it's online, sales-assisted, sales-led, mid-market, SMB selling, or enterprise, large enterprise selling — that tends to be B2B, right? Because most of the consumer platforms are really around driving growth, driving adoption, and driving a growth funnel to go get users and keep them engaged. That's much more product-led.

And so, for me, I started to realize, hold on. If I want to build a career in tech, at some point, I think I need to learn what is classically B2B software SaaS selling because that's what actually a lot of tech go-to-market is rooted around. Now, in the same way that I really didn't have a right to go run a sales team at Facebook coming out of the investment industry, I really didn't have the right to go build and weed software sales teams having sold ads, which I know a lot of folks have referred to as like sales light. It's not a classical Medpick challenge or sales, documented sales process repeated time and again type of model. But it might look a little more like account management at the mid-market and enterprise level. I wanted to get that experience. I wanted to do it in a company that I thought could become something. I wanted to do it with leaders that I thought I could learn from.

That's how I found MuleSoft, and Simon Parmett and Greg Schott, the leaders that I clicked with that were pretty experienced and I thought I could learn a lot from. Really, that was a chance to go report to the president of the company, get a chance to sit at the table and understand how it was being built and what sort of the DNA was. The tradeoff was basically going from running effectively feel large enterprise organizations working with some of our largest customers at a reputable company like Facebook, and going back and running SDRs and inside for a software company named after a random animal, that my mom still asks me about why I made the change to do. With every one of these career decisions, there's always that sort of trade-off of like, okay, what am I consciously trying to get, and how do I make a decision that will solve for that? Even if I trade off some other things, in this position, a name brand of a really well-known company, the comfort and great perks and benefits and pay of a high-flying public company. Really, it was with that. How do I learn B2B software selling? How do I get a chance to learn from strong leaders? And let's figure out where it goes from there. Fortunately, there were some good lessons learned.

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Focusing MuleSoft sales on business outcomes

Alex Kracov: And so from my understanding of MuleSoft, a big shift for the sale was it went from a more technical sale. I think you tried to push it towards more focused on business outcomes. Can you talk about that shift in the sales process and the transition?

Rich Liu: Just as I shared about Facebook was sort of the era of trying to navigate the transition of an industry from a online equal search and maybe some fancy picture display to 'online should be social and online should be mobile,' MuleSoft was navigating it at a separate transition. From a corporate IT standpoint, what MuleSoft does, it's an integration of an API platform. For example, I'm a developer inside a corporate IT organization, and I need to connect SalesForce and Workday. I can write custom code to connect it, or maybe I can write, bring on a platform like MuleSoft to connect the two things. Now, historically, the way that people would do it was oftentimes point to point code. I'm just going to connect things by writing custom code to connect systems. Our pitch was: well, hold on. You should have a platform for that. Because every time you connect it to the platform, you're not writing the spaghetti code that was brittle, that you'll need to rewrite every time you swap one of the endpoints. Instead, you have a reusable set of — let's call it tools that you can then pull off the shelf. Every time I'm Sutter Health, and I need to build the next app for the next type of specialist, I can pull off quite patient data. I can pull off drug data. I could pull off location data and just easily pull it off the shelf to build an app that can be shipped really quickly.

The transition was this industry going from on-prem to cloud, from consumerization of the IT world, dealing with more demands from their end customers to ship the next app, the next service, the next online ordering kiosk, if you're McDonald's, more quickly. Our world was trying to shift it from this technical solution that a developer would buy to, "Wait a second. There's actually a highly strategic framework that you need to construct your IT org, Ms. CIO or Mr. CIO, that we will help you navigate." The way that the world is going, this is no longer just some tool that your developer needs. It's actually a platform that's going to help you develop and ship applications and projects way more quickly than ever before. And so that was sort of that ship that we were trying to navigate. Actually, up leveling the sale to something that is solving a big business problem that is inevitable, that doesn't have other good solutions to it, to an economic buyer that actually controls large budgets. Not a developer who picks up a tool for a project.

Within that transition, we were also going from necessarily inbound, outbound. Because the inbound demand is people who know you for who you are, developers coming in looking for an open source or freemium type product to somebody who's looking for business transformation platform, who's looking for a thought leadership in IP that they can build and construct a new way of operating their IT org around. And so part of that was shaping — I can't take credit for this. I was only part of this machine — the narrative we have to be able to speak to the economic buyer with a true business value narrative that is quantifiable, that is in the terms of the things that they care mostly about, how they can ship IT delivery more quickly and more efficiently, and providing them a way to evaluate that, measure what the business impact they can expect from that is, and giving them a delivery model to go realize that.

As we started to build that, it was about making sure every part of that organization — whether it's the marketing organization, or the SDRs and BDRs, to the sales reps across all segments, to the delivery teams downstream of the sale — we're able to actually speak that language prospect into those right folks of that language, actually sell to them in an effective and believable, credible way, and then go deliver the outcome that we sold to them. That was the transition that I think took a couple or two, probably two to three years, to actually really get through the system, and really helped us unlock a different level of sale and a different level of strategic engagement with these large enterprises. That was really the learning there of going inside to outside, and shifting from a tactical solution to something that really solves and drives business outcomes.

MuleSoft's hiring process for sales

Alex Kracov: And it worked, right? MuleSoft went on to get acquired by SalesForce for a ton of money. I forget the exact amount. The team grew quite a bit, right? Can you talk a little bit about MuleSoft's hiring process? Because I think the company grew a lot, and I think MuleSoft had a reputation for a really good hiring process. Can you talk a bit about that?

Rich Liu: Yeah, I'm happy to share about this. We were fortunate that I think the company grew from maybe about 300, 400 people to similarly 1,500, 2,000 people during my years there. I credit Greg Schott for really giving me religion around what good hiring looks like. I had come out of Facebook. My wife was a longtime Googler. So I was very familiar with the hiring philosophies and rigor that those companies had put on hiring.

MuleSoft took it to another level. On one hand, it's not simply the quality of candidates, but it's really designing a process that measures specifically what we need a role to do. What are the outcomes we need to deliver? How do we measure those outcomes in terms of the metrics and qualitative outcomes that that role needs to drive? Then breaking that back to what kind of skills and what kind of competencies that candidate needs to possess to actually deliver on those outcomes well. Then devising a way to measure for those skills and competencies in an effective and repeatable way that we can then scale across the org. And so we called it hiring 2.0, which Leslie Kurkjian, Leslie Krow's team really helped partner with us to build. Basically, it was that.

Instead of I have a team that has the same role in London, in Sydney, in Singapore, in Atlanta, in SF, how do I make sure that that team is repeatedly driving really high-quality candidates really repeatably no matter what office they're in? And so for every single role, we basically said, "Okay. Let's go define out what are the competencies needed to do that role well. What are the jobs we need to deliver well against it? Let's go actually define those. Let's call it for AEs, an enterprise AE, linear execution. Can they drive a sales process, orchestrate across a lot of orgs? Are they compelling in the room? Can they lead an effective meeting, an effective PG call, an effective follow-through on an executive meeting? In an SDR role, it might be coachability and high-growth mindset and passion for sales. Because we're not just looking for recent college grads who are smart and capable. But they actually have done a passion for going out there and mixing it up and searching for a career in sales.

As we start to define those metrics, I should share that we actually looked at some of our strongest hires historically and some of our weakest hires historically, and tried to actually do some analysis to figure out, okay, what were the skill sets? What were the competencies? What were the backgrounds and prior track records that these folks have had, so that we can actually inform this not just by using our gut, but actually looking at what the data showed us? Being able to map that back to the competencies and then actually figuring out how to evaluate them. And so when we think about evaluation, everybody talks about, "Okay. Let's do an interview." Great. That's like 101. But how do you do an interview loop really well? Well, let's actually make sure that for each of those competencies, we're breaking each interview round to go measure for one or two of those competencies, not all of them, and prescribing the questions that you can use to precisely and repeatedly ask and know what a good answer looks like and a bad answer.

For example, for team player, you can say, "Okay. Tell me about your biggest win. Great. All right. Tell me who was involved in that deal." Do they talk about themselves? Do they talk about the team? Do they effectively break that out, their role versus others? "What would you have done differently in that? Did you get any feedback?" Making sure that those questions are really well-framed and you know what types of answers look good for whether it's team player, whether it's growth mindset, whether it's how they run a process really soundly. Making sure that those are really repeatable questions with follow-ons that, ideally, the same interviewer or a couple of interviewers are always doing so they become experts in betting for that type of skill.

But again, it's not just through the interviews. A lot of great salespeople, great go-to-market people might be great interviewers. But the reality is, how do we actually understand how they would do the role, not just talk about it? Can you design an exercise that mimics a skill or skills that they would need to do in a role? If you're hiring an EA, "Hey, can you walk me through this calendar? What would you do with it? What would you prioritize? What questions would you ask?" If you get an email from somebody saying, hey, can I get some of Rich's time, how would you respond to that? What would you be looking for? How would you prioritize? If you need to plan an off-site for an executive team, what would you need to know? How would you look? What are the types of things that you might start to spec out for that?" It's some kind of an exercise that really helps to demonstrate an environment that looks like what they're going to be doing, how would they actually perform in that, and actually rating that with a rubric that you use every time.

Then finally, references. I know I've talked about this before in other venues. But so often, sometimes we do the reference call. It's like, "Is Alex awesome?" Jack Altman can say Alex is awesome. And if I call Jack and I said, "Hey, I really want to make sure that there's the right fit and for Alex's sake, because we like him a lot. So the more candid you are with me, the better. Help me understand what are the areas of strength. But what are the areas that you were focusing on to grow? What are the ways that you would coach me to go work with them well to make sure that we can set them up for success." Those types of questions that really help that reference feel like, oh, if I answer and I close some positivity up this interviewer's backside, it's actually not going to set the candidate who I like and trust up for success. That's really important to establish, and knowing that you actually care about that feedback. Not just you're there to check a box. That's really important.

Obviously, ring fencing those references to direct managers, not pick somebody who you work with who can say great things about you is really important as well, if you don't have trusted backchannels that obviously won't blow up the confidentiality of the candidacy. So just a few of the profile of like, I started a few of the elements of the hiring 2.0. It was making sure that you design well. You design the process well for vetting for what you need. Finally, you actually have controls of people who are pushing back and creating that constructive tension so that the CEO, the CRO, the fill-in-the-blank executive needs to personally vet and inspect and actually sign off on that hire, because he or she or they are confident that that person is going to be a 10x-er and raise the high-water line, not the low water line of the org.

Alex Kracov: I love your answer because it just describes how much pre-work there is when it comes to interviewing and hiring people. Just structuring the role and being really deliberate and thoughtful about the structure around the entire interview process, that sort of leads you to the right outcome rather than just being really good at asking specific questions to the candidate.

Rich Liu: 100%. And again, it sounds heavy, right? It sounds like, "Oh, we got to have a ton of time and a huge HR talent team to do it." You'd be surprised at how a little bit of thought, like spending an hour or two upfront to design a proper interview loop and vetting process and a proper profile, so that if you have recruiters, they know what you're looking for. If you have interviewers and your panel, they know what you're looking for. That alignment around what the role needs to be and what the right candidate looks like and how to bet for it, investing in that upfront is so valuable in driving efficiency and effectiveness in making the right hire, if you just put in an hour or two upfront.

Scaling enterprise sales at TripActions/Navan

Alex Kracov: So you joined TripActions as a CRO after MuleSoft. I think during your time at TripActions, a big part of that story was actually scaling the enterprise business. I think it ended up accounting for over 30% share of new business, you 3x day as average sales price. What was that transition moving up market? Because corporate travel, massive industry. You have a competition, a lot of incumbents. Can you talk through how that all went down?

Rich Liu: Yeah, it's a great question. Again, for me, MuleSoft was learning B2B sales and figuring out how to learn from people who've done it. For me, I knew that, where my passion lied. I thought where my skill lied was in trying to figure out go-to-market that was maybe a little more nimble and dynamic versus what was mostly a large enterprise sale. At the time, TripActions was probably — it was the earliest company I joined by a longshot. Probably only a few million run rate, less than 100 employees. Maybe 80 employees. They had a really good product, a beautiful product. It's like this consumery. It looks like Netflix for travel already even at the time. It looks great now. It actually looked pretty good. Where it was really effective was sort of this mid-market space, where early adopters, few 100-employee companies that had enough business travel where it mattered but maybe we're still nimble enough that they cared about the employee experience, and not as much about the controls and security. That was a great sweet spot for where the early adopters were.

When I joined, Ariel Cohen was the CEO and Founder. He really had a vision. He said, "You know what, Rich? We need to figure out how to get this thing as the default for all travelers." Again, he walked into the old office with stains on the carpet. We're like, "Wow, that's a long way from now." But I appreciated that that vision was always there. It's going to be everywhere. It's just a matter of time and in what order. And so with that mandate, it became, all right, let's figure out. We have this stronghold in this mid-market today. Being everywhere, down market and then up market, it meant not just these early-adopting tech companies but all industries as well. The manufacturing company, the CPG company, the services company should all be using this thing. So it became an exercise of sort of like, all right, well, let's do the chess game of, what keeps us from going downmarket? What keeps us from going upmarket? What keeps us from going into all these verticals?

First of all, when we thought downmarket, well, hold on, the product actually already worked great downmarket. We just weren't selling at a high-velocity motion yet. So that it wasn't a really, highly economical type of sale for us to do to sell or service to yet. Well, great. If that already works well with the product as is today, let's go build a velocity team to go after it. So Lauren McGuire, Lori Jimenez really spearheaded folks that came out of that Box sales leadership team under Leslie, Jim Herbold and others. They just lit it up, building an efficient sales and success motion to go service this fast-velocity business. When we looked upmarket, the product actually worked pretty darn well up into a point. Not the largest businesses on the planet that have all sorts of weird policies and customizations you got to do. But it was actually working pretty darn well even at the early days up until several thousand employee companies that were spending probably 50 million a year on trial. And so we said, all right, well, let's not go too big and spend the time selling to people that the product wasn't quite ready for. But let's actually go to that next tier up market and build a team against that, and be really disciplined around what types of sales cycles we get into and don't. Then use that team to start to learn. "The next year looks like this. They're going to want this customization. They're going to want this type of security control. They're going to want this kind of admin tools or manager tools of reporting. They're going to want these types of integrations or global inventory of travel, because that's the key places that these large companies tend to play." But it was really about trying to sequence out the different order of those efforts so that we're not trying to do the thing where it's like, okay, be everywhere all at once. Not just a great movie but a terrible business strategy.

The other piece was like, okay, how do we go different industries? That was really an early adopter to early majority mainstream conversation. We had a great product and marketing leadership team under Matt Smith and Meagan Eisenberg — who I'm a huge fan of — around, all right, well, wait a second. The premise right now and in the early days was, "Here's a really cool Netflix for travel. It looks amazing. Your travelers will love it. And you'll save some money if you manage it well." That doesn't resonate with a CFO. It doesn't resonate with that true economic buyer. It resonates with a traveler. It might resonate with an HR manager. It might resonate with a finance manager. But how do we actually turn this into, similar to MuleSoft, a message that actually the person who actually controls the bigger purse strings cares about?

It was funny because, at the time, MuleSoft had recently IPO-ed as you mentioned. A lot of this inspiration came from conversations that we had had with our CFO, Matt Langdon, there. We had IPO-ed. We were increasing growth. I think the goal was, let's go grow 70% year over year. Meanwhile, our T&E spend had more than doubled. Matt sort of pulled us together and said, "Hey, folks. We have a problem here because we're a public company, and we can't just double this T&E spend to grow the business 70%." We sort of looked at him and said, "Matt, it's okay. We're salespeople. It takes money to make money. Leave us alone." Matt sort of said, "No, you don't get it. T&E is the second largest line item in the company after payroll." Now, this is an enterprise software company. So plenty of travel involved. "If we don't fix this, we don't have a company. At least, not the kind of company we all want to be in." Oh, that's important. And so again, wait a second. How do we go fix it? Everybody, save money. Let's go send the head of business analytics to try to map out in Tableau all the different spend coming into Concur. Then figure out where it's coming from.

Sandeep Madhur ran business analytics. He's at Everlaw. All kind of circling now. He did this big exercise. He's trying to suck in all the receipts from Concur, and we still got to 80% accuracy. All that accuracy was like backwards looking at the last six months now board looking. And so that was like aha. It's like, oh, hold on. Instead of this cool Netflix for travel thing that travelers love, how about a better online travel solution that if travelers use it, the CFO gets real visibility in real-time around who's using it, who's not, who's in policy, who's not in policy, and can better visualize and manage this second largest line-item budget? That's a strategic tool the CFO care about. Again, with the way that Nevadans has moved towards payments and expense, now, they basically captured all the spend on a corporate card, a virtual card at the point of the sale where they can apply policy, and then bump it up against the guardrails of what people should and shouldn't be doing. So it's a whole different level now. But even back then, there was that powerful narrative of, "Oh, that's a story that doesn't go to tech early adopters. That goes to a CFO in any industry who cares about her business and running a tight ship." So that was sort of the aha to try to bring that narrative into that sort of business value world that can take us to the mainstream. Again, it sounds easier than it was. There were so many people at the table for that that played out over at quarters. But that was sort of the journey of down, up, broad and, obviously, international as well as we were trying to build that thing.

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How does Rich scale himself as a sales leader?

Alex Kracov: So you've had a tremendous career, right? You've worked at some of the most legendary companies in Silicon Valley. On the surface, it seems very positive. But I'm curious, how are you able to scale it yourself? Because you went from working at Facebook — high-growth company but a pretty big company — to kind of just being a big tech exec at these B2B companies. And so can you talk about that journey of scaling yourself? Were there any tough moments for you personally along the way?

Rich Liu: Thank you. That's very generous of you. I don't go home and have my kids call me a big-time tech exec. So I'll take that.

Alex Kracov: But you are.

Rich Liu: It's funny because, oftentimes, it's easier to look back than it is to look forward. When I think about every one of those moves, and the plenty of mistakes that I've made as well, there's a lot of learning involved. I'll say this. My old CEO years ago, Ken Fisher, used to say it's better to be lucky than it is to be good. And I would say that, for every single move that I've tried to make in my career I think at the time, it didn't really look like, "Aha, this is the natural next thing to do at the time." When I left the investment industry to go to Facebook, every other social media company before it had gone kaput. And so, who's to say that wasn't going to happen at Facebook? My mom was telling me, "Don't do it." Meanwhile, I knew I wanted to get exposure to tech at a top-tier tech company and be able to watch, hopefully, an industry transformation if it played out.

On the move to MuleSoft, similarly, my mom was like, "Don't do it." I think you'll hear a similar refrain here. You're leaving this top-tier tech company to go to some random company that's been around for 10 years, and maybe is on an IPO path but maybe not. To go back from running field sales team to SDRs and inside sales, what was the goal of it? Just to be really clear of what I was hoping to get and learn, and the experiences I wanted to have, so that I can work on completing myself and getting those experiences. Even with TripActions, even a post-IPO company that's still scaling and selling off to Salesforce for $6 or $7 billion. Would you rather be an SVP in SalesForce or the CRO of a random company that nobody has ever heard of? For me, I thought: one, I love travel. Two, I had a lot of faith in the vision and the strategic mind of our EO and the leadership team. I thought, you know what? At some point, I want to learn in an early-stage software company. Let's give it a shot. And if it doesn't work out, I can always go back and do something else.

I think at every point, there were a lot of mistakes and screw ups along the way and certainly learnings that I've had from not doing the right thing. But I tend to think about careers as long things and over time as long as I'm still learning new things and reflecting and growing as a human and as a professional. Hopefully, that's the name of the game. By the end of it, hopefully, I'll be able to look back and say, "Hey, I grew. I had some impact. I created some impactful and memorable teams." That's really the goal. But we'll see. Ask me in 10 or 20 years, and I'll tell you if it happened.

Alex Kracov: We can record this again in 10, 20 years.

Rich Liu: Along with the New York Times from today.

Alex Kracov: Yeah, I love it. I mean, I think it's a great career advice for anyone. It's like follow your learning path and look for jobs based off, I think, where you see the most opportunity to learn, whatever's most interesting to you. I think that's a great advice for anybody who's listening.

Rich Liu: And it doesn't have to stay the same all the time, right? You might learn and go, "Oh, I really don't like this thing. I need to be back doing this other thing." But with that method of successive approximations, hopefully, you can at least cut out the types of things that don't bring you energy with every new transition.

Being the CRO at Everlaw

Alex Kracov: Now you're the CRO of Everlaw, which you sell to law firms and government agencies.

Rich Liu: And corporations.

Alex Kracov: And corporations. Okay. What's it like selling? Maybe I'm thinking about this wrong. But do you sell to more traditional old-school industries, or is it sort of to everyone? How do you think about the sales motion at Everlaw today?

Rich Liu: Yeah, it's a great question. Everlaw, in the spirit of learning and growing, I've never worked in a vertical SaaS company till now. What attracted me to the company is, you have this massive industry, the practice of law that is so deeply embedded into our society and culture. Down from watching law and order to the stuff I read on CNN about the special master digging into ex-presidents' documents. It's so deeply embedded into everything we see and do. Yet it's been so old-school in the sense of technology adoption and the risk-aversion and wanting to make sure that everything feels safe and right before moving forward on technology. We have a really interesting time in our space. Because with LLMs in AI, the idea of how AI and technology will revolutionize the practice of law and make the practitioners far more efficient than ever before, that's a more exciting time in our industry now than ever before.

Our sale is really interesting, because we have three key types of segments that we sell to. We sell to the government. The Department of Justice is a customer of ours. The state attorney's general, the team out of DC that Alan Lawrence runs to Josh Buckler's team. It's a very unique team in that they need to understand the buying cycles, who's involved, how decisions are made, and how contracting gets done. We have sort of our core legal sales team that sells to law firms — big and small. They need to understand how partnerships work, and how decisions are made in a world where there isn't necessarily a CIO or CTO who's going to, "Aha, it's my responsibility to buy technology. Here you go." That partnership is driven by profitability. Anything they invest in technology is money out of their pockets at the end of the day. How do we help frame to them that this is not just a necessary tool for doing litigation investigation? But that's actually going to fundamentally help them run a much more effective and profitable practice — whether it's closing new business better, whether it's we’re working far more efficiently, whether it's just finding better outcomes when they're trying to figure out what happened in a case?

Then finally, we have corporations who the GC is there thinking, "Well, I pay $1,000, $2,000 an hour for outside counsel. If I'm doing discovery, if I have an HR matter, if I have an IP matter, it's actually really strategic to own some of those capabilities internally so that I can actually better understand what's going on in my business before I outsource it. And to be able to do so actually helps me operate a lot more cost effectively, too." So there's like different sort of framings of where value is derived, different structures around who the decision makers are and decision process. And so for us, it becomes a question of, how many different bets can we be taking at any given time and resource well so that we can be effective and successful in those bets?

For us, it's less about, say, global markets. We have US, the UK, EMEA market, but we're not doing a large broad global play. But more about how we can think about how to sell and service and deliver really effectively for these three pretty discreet types of organizations and buyers and users. So that's really the name of the game in that world. It's how do we actually make sure that we can take on enough surface area, where we can still be successful at driving a strong sales customer adoption, value process for that buyer instead of the tempting thing to do which is to spread ourselves really thin and have a few people running at a lot of things. For earlier stage startup, a lot of value to do that to at least map the world and figure out where the places to really spend time are. In a company at our stage, late stage private, really valuable to be really disciplined in making sure that our core business is running and running really effectively end to end, and then being able to start to fund the bets outside of that.

Selling in a tough market

Alex Kracov: Super interesting. Obviously, selling in today's market is really tough. Budget scrutiny is high. Sales cycles are getting longer. I'm curious how you sort of coach your team through this market. Maybe what advice do you have for other sales leaders who are kind of dealing with all the dynamics today?

Rich Liu: Yeah, it's a great question. I was just sitting with a number of startup founders and heads of go-to-market last night with NewView Capital. A great group. A lot of folks had shared, "Well, our pipeline is slowing. Our sales cycles are lengthening. Our win rates are decreasing. It's harder to get budget." Almost anybody selling anything is saying that right now. In this environment, it's very natural. Internally, our CFO, Scott, is saying, "Hey, if it's not business critical, why are we using it? Why are we paying for it?" Or forcing us to get leaner, because that's the current climate as it is for most companies in America and beyond. What that means is, all right, well, the sale of, "Look at this amazing product. It's awesome. It's going to sell itself," all of a sudden, that sale around how amazing the product is — the features, the benefits — might not work as well.

So what I found or where we found in this market, and what we found at TripActions or Navan when travel dried up during the pandemic was, hey, if we don't have a very clear line to the economic buyer themself, or himself or herself, that sale, you cannot consider is getting done. Number two is, if you don't have a very clear articulation of what it is and understanding of what it is that that company cares most about right now — what are the biggest things that the CEO, the CFO, your economic buyer is thinking about at night, what keeps them up, what they're afraid of, what they're ambitious about — and if you can't go connect what you do very directly to those one or two things — it's not three or four. There's one or two things — in a way that is credible and quantifiable, you should not expect that sale to get done.

What does that mean? That means the challenge becomes, how do we make sure our narrative and our product — first of all, does our product actually do something that is meaningful and valuable and differentiated and drives business results for the buyer that we care about? If not, let's go figure out how to make sure it does that. And how to make sure the buyers that we're targeting, the personas, the ICPs that we're targeting, there's a really strong product market, product customer fit. Once we know that's the case, then let's make sure our narrative actually resonates with that, that we've built those quantifiable data points that we can show them, that we can build out for that client specifically that that kind of value that will drive for them in the criteria or the currency that they care about. Then let's make sure that we are building strong champions who will get us to an economic buyer so that we can have that conversation directly.

To me, if you don't have those elements in your sales process right now, we're actually in your go-to-market and your overall product market or where you're focused as a company, things are going to be hard. Now, that's not a doomsday scenario. It's not a, what if you don't have those things? Just fold up shop and stop doing it. It's just a challenge to say, how do we go find those things in the go-to-market and the product in the sale that we're looking to execute today, or go get us there?

At Navan and TripActions, the idea of, "Hey, let's go help you do corporate travel much more effectively" all of a sudden sounded really tone deaf in March of 2020. Wait a second. You weren't telling me to travel more? Are you insane? Do you want to get me killed? But the idea of, hold on, do you think travel will come back at some point? If no, then we probably shouldn't be talking. If you think it will at some point, yeah, let's talk. Great. Is travel when it was big when it was happening, or when it will come back, is that a meaningful part of the budget that you want better visibility? If yes, great, let's keep talking. And if those things are true, then let's actually use this time when you're not traveling to actually do a thorough review of the program, so that you're not trying to build the plane while you're flying it. That you're actually building the plane while it's in the hangar, and you have this unique opportunity to go make sure it's built right. So that's a narrative example of why the worst time is actually the best time to be looking at something.

By the way, speaking of the product pivot, hey, you might not be looking to do a lot of travel. But we have this FinTech product. We have this spend management expense solution. Are you still having people now work from home in expense lunches, or expense trainings, or expense equipment? Do you have policies around that? Let's make sure we're helping you manage that spend really well? Because guess what? In this COVID environment, we don't know what's going on and what will happen. So it's more important now than ever to manage that side well. So a product pivot, a product acceleration that really played to how do we actually speak to something that's really resonating with the same buyer right now that complimented the previous narrative. So that was really how I think, in practice, that playbook sort of works out.

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How will AI impact enterprise software?

Alex Kracov: I'd love to end today's conversation a little more forward-looking, talking about AI. Because I know Everlaw has been investing quite a bit into AI. I'm just curious what you think about the current AI wave. You don't have to speak specifically about Everlaw. You can if you want. But how is AI going to just impact enterprise software generally? How do you sort of think the future might play out?

Rich Liu: Yeah, that's a great question. I'll preface this by saying I am not an AI expert. I am not a technologist. I am a business leader. But from what I've seen, and having seen a number of industries transform or go through this period of massive shift, I'll speak specifically to the legal industry. Because there was a Goldman study a few weeks ago around industries that will be most disrupted in terms of jobs that can really be replaced from AI. I think out of 15 or 20 industries, it was like office and admin work and then legal. The two are actually pretty closely related, so I'll lump them together.

When I think about legal as an industry, historically, it's been very much driven around people. It's a professional service industry. You have people who have expertise who can help you research what happened with the evidence, who will put together a case, put together a deposition. All those require humans who are using their JDs, their expertise to go comb through evidence, to go prepare a deposition right up. When I think about the role of AI there, we've been historically already using AI to shrink the haystack to give people sort of pockets. Oh, if you're interested in this, you might want to look here. These pieces are linked. Let's shrink the haystack. But when we think about what's possible with AI, the idea of, in the future, do we use a tool like Everlaw to help think through? Hold on. There's a lot of stuff going on here. Can you simplify it for me so I can quickly understand what's happening in this document?" Or, well, there's a future world where we might say, "Hey, what's going on with this mountain of evidence? Can you help me figure out a few of the themes of whether this is going on or not, and how it's substantiated with evidence?" The possibilities start to get really mind-boggling in an exciting way around the things that we've historically relied on really smart, really experienced human beings to do. Now we cannot just simplify their lives, but we can actually help do some really heavy lifting for them in a way that has only been sort of science fiction in the past. That's the kind of thing that we're looking at as now being possible or very close to possible.

Obviously, our stance as a company is, there are a lot of people that pretty much everyone in their brother and sister are talking about how they are AI-based and AI-driven. It's really important at a time like this to actually try to separate the wheat from the chaff, and the people who actually know what they're doing to align yourselves with versus folks that are just saying, "Hey, we know AI. Trust us." There was a famous example in the New York Times just a couple of weeks ago of a lawyer who pulled out ChatGPT and said, "Hey, write me this lawsuit that I'm going to bring against a major airline." ChatGPT had some hallucinations — not through a fault of its own but a fault of the user — cited case text that was not accurate or not real. Obviously, this lawyer got an egg on his face.

Now, that's not to say ChatGPT is terrible. It's actually an amazing technology. But we need to implement it and use it in a way that's highly trustworthy and safe, and that we can help really empower the users to do really high-value things with it versus just use it in a cavalier way. That's really our philosophy of thinking about how to implement LLMs and the future of AI as it relates to legal. But we're really excited about where the space is going. And as a proxy for most knowledge work, just the things that we're working on in our roadmap, give me a lot of optimism about what the future of work looks like in the years to come.

Alex Kracov: Well, thank you so much for the wonderful conversation, Rich. If people want to follow-up with you and find you, what's the best platform for them to reach out?

Rich Liu: I'm not super active on Twitter, but you can find me there at @richliu. You can find me on LinkedIn. That's probably the easiest way to catch me. I'm not always super responsive, so I'll provide that caveat up front. But hopefully, there are some valuable stories. If I can be valuable to you and the Dock team or the community, I would love to put myself out there.