Liam, how are you doing? Nice to see you. You too, man. Doing good. Welcome to Between Two Hires, the subtle art of not f*cking up your sales team. Liam thanks for joining. I don’t know if you just want to give a very brief sort of outline of how you’ve got to where you are today. Yeah. I’d be happy to do it.
Thanks again for having me on. So I work at Kleiner Perkins. I’ve been here for two years. I’ve focused on working with the B2B portfolio companies on anything Go-To-Market related, primarily with sales, but I think everything culminates with sales, so that also means I have to work across marketing and customer success and solutions engineering and everything else in between.
Before this, I was at another venture firm seed stage fund called Unusual Ventures that I helped get off the ground. I was there for three years. We had raised two funds. I’d done something very similar where I basically jumped in as the first sales hire for a lot of the portfolio companies we invested in.
I did that for probably 30-ish companies. And then before that I was at MongoDB as a sales leader and a sales rep. And then what feels like many moons ago, I was at a healthcare startup and then started my career in advertising. Very good. I must say, I’ve seen some of the most successful transitions from SaaS sales, particularly in good companies like Mongo and others, moving into TA.
Very curious how that happened. And if you feel like the same when it comes to that experience blending into now what you’re doing. Yeah, I- when I was at Mongo, I think the most enjoyable part of that journey for me was the run up to the IPO, just because it almost seemed impossible. It was a audacious goal.
I’ve never been part of such a group that had such talent density and focus and drive. And it was just very intense. It was a formative stage of my career. And when we went public after that, nothing changed and everything changed. I think from what they’ve done from the moment we went public in 2017 to where they are now is incredible.
But to me, I just love being a private company. So then I thought, how can I craft a career where I spend the majority of my time with private companies? Who does this all the time? VCs do this all the time. I didn’t have any contacts in the industry, so I just started the cold outreach to the Midas list in 2018.
I reached out to probably 80 of the a hundred on the list. I heard back from 10 or 12. Half of those were no or go to business school. And then ended up through the network, getting conversations with John and Jyoti that started Unusual. And they, before they even took a bet on me, which I think was appropriate, they were like, look, you seem good.
We know Mongo is great. Why don’t you moonlight with one of the founders we’ve already invested in, and they’ll make the call on if you’re good enough to do this job. So I would manage the team that I was managing from eight to six. And then from six to 10 PM, I’d work West coast hours with this founder of a seed stage company, trying to get it off the ground.
And it worked. And then they were like, “Hey, all right, we’re going to give you the job. We need you to move out to California in 30 days.” And that was not on my roadmap. That was not on my wife’s roadmap for sure. So luckily she gave me the thumbs up and we moved out there. And, uh, you know, working at Unusual was a formative experience, not only in just transitioning to venture, but what early stage is. When I started at Mongo, we were already doing like 50 or 60 million ARR.
I left, when we were around 250. So then I really got to see what it is to close your first 10 deals, 20 deals, million dollars of ARR. And then I met KP through the industry and wanted to work again with sales leaders and sales teams, which usually happens after seed stage. And been here two years doing something pretty similar.
And I’ve only heard pretty phenomenal things from anyone that I’ve introduced your way. So the feedback’s always been extremely high, which is not surprising for one second, but we’ll probably get into a bit more about why that is in a bit. So yeah, just thinking about the numbers here.
How many people have you hired, sort of directly and maybe indirectly as well? It’s got to be above 50. It’s honestly probably above a hundred at this point. And I think the majority of that hiring has occurred in the past five, six years I’ve been in venture because I’ve worked with probably over a hundred portfolio companies across two firms.
Hiring is one of the biggest ways we can have a outsized impact on any given portfolio company. And whether that’s, whether it’s a CRO and SDR, a head of CS, demand gen, marketer, anybody on the Go-To-Market side, I’m usually involved with interviewing. So it’s probably over a hundred at this point.
And when I was at Mongo, I had recruited reps that were on my team as well. But it’s been a pretty nonlinear ramp since I started in venture of recruiting being a outsized portion of my job. Good. I’m curious about some of the stories now. So if you could, best hire story, followed by worst hire story.
You know, you sent the questions in advance and I was thinking about the best hiring story. I don’t necessarily have like a heroic hiring story. I think one learning that I’ve had across recruiting for startups is don’t think that anybody is unrecruitable. And I think even if you go after someone who see- like I can’t tell you how many people in different portfolio companies are like, “Hey, do you think we can get Chris Degnan to be our CRO of this series A company?” CRO at Snowflake from the beginning
for those that don’t know. Nice. And I’m like, “Hey, look, probably not. But I love the fact that you’re thinking that big. So who would you put in the same caliber or who is a couple o and let’s go after them because they may be able to introduce us to the perfect candidate, or they’re going to give you some incredible feedback as to
how you can pitch the opportunity better, why they wouldn’t join, who they think might be a great fit”. My best recruiting story might’ve been how I broke into tech. I know that seems self serving, but I do think there’s a good lesson in it for people. I was working in advertising. Then I took a bet and worked at a healthcare startup that ended up getting acquired.
It was nothing, you know, nothing spectacular. I wanted to go do that again, but at a real tech company that had VC backing, my previous company had been private equity backed. I made it to the last round of interviews with MongoDB and the CRO said, no. He’s like, you don’t have a traditional profile.
I don’t want to take a bet on somebody right now. We have too much to do. So I went home and told him I didn’t agree, but he’s settled to his own opinion and tried to figure out just how can I stand out? A lot of people that I’d been interviewing against had a very classic background, EMC, App D. Let’s go to Mongo and do it all over again.
A big part of any sales role is just getting people’s attention, especially executives. So I had a cardboard cutout of myself made. It was like six feet tall. So I gave myself an extra couple of inches. And I mailed it to the office and it just said, can’t you see me working here now? Because I had nothing to lose.
He had already said no. And then I got an email the following Monday, cause I overnighted it. And it was like, “Just got your package…” And they ended up taking a bet on me. I found out years later that there was a handshake bet between the CRO and the SVP, that I wouldn’t make it two quarters and they’d have to buy each other dinner and I ended up, going to president’s club that year.
And then I was the top manager in the company, and the year following. And that CRO now, I’d consider a mentor and a friend. So I think just go for it. There’s another guy in our portfolio at Rippling that did something very similar. He tried to get hired by Google early in his career and had a skywriter write
“Hire me” in the sky and the stuff isn’t like as expensive as you think, but it’s a way you can get attention from executives and just shows that you’re willing to have that persistence. The worst hiring story happened recently. Really important hire for a portfolio company. We’ve been going at it for three to four months, the CRO role found what I thought was like the perfect candidate in terms of their make up as a person, their background of experience and the alignment of where this company needed to go.
Really hard recruiting process. And then they sign. Everything’s good to go. Sign the offer letter. I talked to his family about it over the weekend, sign on Monday. And then the next day it had to be 24 hours later, 48 at the most, called the CEO and was like, “Hey, you know, I just talked to my founder here and I’m going to stay.
And I changed my mind.” And that to me was the first time I’ve ever had an exec sign an offer letter and like really commit to a company and was going to travel to the offsite and then just completely back out at the last minute. And we got caught flat footed because at that point, I also had kind of let the pipeline for this role dry up because we were all focusing on this one candidate.
So a lesson in there for candidates, like if you’re having an existential crisis about a role, just be upfront about that and definitely don’t sign an offer letter. And a lesson for me that like, it’s not done until they show up for the first day, right? I think anybody who’s been recruiting for a while and those stories of candidates just not showing up for the first day and that’s how you find out they had a change of heart.
So it’s not done until they’re working from a laptop, then sending emails from their company email. Very true. I was not aware of this cardboard cutout- phenomenal idea. After year one, they were rethinking how they evaluated you in the process too given your performance, so. Really well done there.
Hey, I get it. I don’t know if I would have hired me right at that stage of the company, but I’m glad it was a really important chapter of my life. And it was probably the best 80 I’ve ever spent, so. Very nice. In keeping with that performance aspect, what’s your secret weapon to recruiting and sourcing top talent?
I can tell you what I do. I don’t know how much of it is a secret per se. If you want to go find top talent and you’re, I’m assuming the baseline for most people is they know what top talent is for what they’re recruiting for. Use their networks. I think it’s something that people don’t really do enough, right?
Even if you know somebody who’s not on the market and you think they’d be the perfect candidate or you think they’d just be a great person for the team to talk to, to understand what the mold for excellent looks like. Ask them if any of their friends or anybody in their network is looking for a role.
Like who do they think the best salespeople are at their company or in their network or in their friend group? I actually think people don’t use their networks to the full extent, or just go cold to someone and say, “Look, I think you’d be phenomenal. Here’s the role. My guess, you’re probably not in the market right now. But if you know anybody who is that you think is excellent, it’d be really meaningful for me to talk to them and just calibrate.”
So one, I’d say go find excellent people and mine their networks. Whether you know them or not. I think the second thing, and this is very specific to sales and it’s very specific to early stage sales. Let’s define that as series A to series C. I tend to only recruit out of companies whose products do not move without a sales team.
I think there’s been a lot of myth of like the field of dreams company building model at the early stage. If I build the best onboarding experience, if I build a self serve product and if I really have slick marketing, there’s going to be a flywheel of self serve usage in some form or fashion.
And then I can throw a sales team against that inbound or that pent up demand. I just haven’t seen it happen. And when it does, it’s extremely rare. So I go to find companies whose products are a little bit heavier, like they’re probably not really great for PLG. You definitely need a salesperson involved to crack into accounts.
Maybe it’s a complete new use case, or they’re a challenger brand. They probably need a solutions engineering team because it may be non trivial to set up. And all of that just means you have to do three things really well. You have to know how to outbound and you have to understand the importance of that.
You have to be incredibly good at qualifying and you have to be incredibly accurate in your forecast. Because if you can’t do two of those three things, you’re probably going to be unemployed by companies like that. At least that was my experience at Mongo. And then I’d say the third is go look at markets that you think could be really good to recruit from and go to the second or third place companies and go find the best salespeople at these second or third place company. And unlock them from the burden of not being able to catch up to whoever the market leader is.
Because if they’re still excelling at whatever their metrics are, and their product is seen in whatever light as not the market leader, I think it’s a really good place where people can learn how to sell in some pretty adverse environments. I just have made it a rule that I will not recruit from companies that have had incredible PLG flywheels, unless the company I’m recruiting for has one.
And again, it’s just incredibly rare that that’s the case. Good. The fortunate position of seeing some quite weird and wonderful things along the way, working on talent, working with people. What’s the weirdest interview, weirdest interview moment you’ve experienced? Weirdest thing I can tell you- the weirdest interview moment I’ve ever had.
And I don’t know if this was the biggest, one of the biggest lack of self awareness moments or one of the best power moves I’ve ever seen. And I’m still on the fence. I’m interviewing somebody and they were in New York. They’d come to the interview and they were like, “Hey, is it okay if I just eat something while we’re interviewing? I haven’t had a chance to have lunch.”
And I’m like, Hey, that’s fine. You’re sneaking this in. You got a full time job, like just here’s the snacks. You know, do your thing. He came back with an apple and I was like, okay, interesting choice for an interview, but not a big deal. Like I get it. I’ve been there too where I’m starving.
Throughout the interview, he’s eating the apple, not in the most slick way between answering questions, gets down to the core and I’m kind of like, okay, good, that’s now that that’s done. And proceeded to just eat the core. And I’ve never seen someone eat a full apple. And I didn’t have to say anything because I think my face said it all.
I was stunned. That to me stands out as probably the weirdest experience I’ve had. We didn’t end up moving forward with the hire, but who knows? Maybe that’s a level of grit I just wasn’t ready for, where Apple cores were nothing to an individual like that. Sounds like this guy goes all in.
All in. Yep. Finishes the job. You can take it a lot of different directions, but that was pretty unforgettable. That’s a new one to me too. Very good. Oh man, that’s, yeah. I’m trying to get past that mentally at the moment. Same, yeah. Years later. I’m still trying to get past that. Do you have a conventional interview question or tactic that you like to use?
Yeah. Again, I’m going to preface this with the majority of the last six years for me have been early stage recruiting. So I wouldn’t use this tactic if I was at a company that was past product market fit, call it, I don’t know, 50, 60 million in ARR. What I try to do in a lot of interviews, especially for sales people or sales leaders is push them away from the job in our first call.
Try to unqualify them. Usually they’re in a position where they’re doing well. Maybe they’re at a similar stage company. Maybe they’re a little bit later down the road. Maybe they’re at snowflake and they’re doing really well. And they’re looking at joining a team at a series A or a series B sub 20 million in ARR. A lot of wet cement.
A lot of things need to be figured out. I’ll just ask them. Why do you want to do this? Look at your W2 from last year, cut it in half. This is going to be a tough year in terms of you getting your feet wet, the company figuring things out. You don’t come to startups to get cash rich in the first year.
That’s that’s generally the rule of thumb that I’ve seen happen. It’s really brutal. It’s super competitive. We’re still somewhat unknown. The incumbents are pretty deep that we’re trying to unseat. Budgets are getting tighter. The current macro environments is pretty tough. I’m sure it’s even tough at companies like snowflake and the like.
So why would you do this? Why is this appealing? You see, you have to be a little bit nuts.
So yeah, that’s typically what I’ll do is try to push them away from the role, right. And then I just want to see how they jump back in. Because what that gets to, which is the second point of what I tried to look for is what’s their intrinsic motivation? What really drives them? At the end of the day
what is the ember inside that’s really going to propel them through these hard moments? Because that’s going to be the majority of the time, is hard moments, even when it works well. So if they come back and they tell me that, you know, this is what they’ve been dreaming of. They want to get to the early stage.
They think they have so much potential that’s not being realized at their current opportunity. They’ve seen their VPs make a lot of money and they wanted to be those individuals. They felt that they caught the bus a little late, even though their current company is great. Whatever they end up anchoring back to that to me is what’s important.
And they have to start trying to take the job out of my hands instead of me pushing the job on them. I think founders can take a similar tactic. And then after you dig into the internal motivation, to me, it’s like, I like to ask reps and leader candidates, what are you going to do in the first month on the job?
And what you should look out for and what to me is negative signal is again, at the early stage and answer that it’s like way too much learning. I’m going to learn. I’m going to do a listening tour. I’m going to- and I’m like look, there’s not that much to learn. Like this company is not going to move unless the sales team moves it.
There’s no inertia that we can just ride. So obviously we’re going to learn and help you ramp and stuff, but there’s not that much, it’s a thin book. You know, like nine month ramps are inappropriate for startups. So I’d rather them start to answer and really dig into what actions are you going to take?
How would you measure progress? I almost want to hear them saying they’re going to do so much I don’t think it’s possible in the first month. That to me is how I would skew on that. And then I think from the company standpoint, for what it’s worth, if you can find candidates like that, really good intrinsic motivation, lines up at the early stage, has a bias for action.
You have to take their onboarding and their ramp as serious as you take recruiting. I think that’s one of the worst handoffs in startups. You really go in, maybe you’ve even, you work with a recruiter and you’re spending a lot of time, a lot of expensive time getting these people. And you make a really important decision for them and you to change their life and your company’s.
And now they’re here. And then I see a lot of teams are just like, okay, great. You got your laptop. Here’s your Slack login. Here’s a couple of Google G drive docs. Go for it. You know? There has to be like an orchestrated first 30 days where every week that new hire leader or individual should feel exhausted.
After their first week, they should feel exhausted because they’ve been talking to so many people. They’ve been getting into the weeds. They’re probably already taking action on whatever’s in their purview. They’re presenting things back to the team. They’re doing a pitch in front of their peers, remote or in person.
You got to nail that 30 days and that’s on the founder and the team to do that. Because if you can find a candidate like that with incredible drive and real deep focus, if you blow their onboarding or the ramp, it’s going to be their first hesitation of like, was this, did I make the right call here?
Because they know how to value their time and they know how to evaluate good environments and opportunities. So shoot yourself in the foot by not having a plan for what their first month looks like. Couldn’t agree more. I think you nailed so many pretty important aspects there. And even down to the period of time between the offer acceptance and them starting also being pretty crucial and where I think a lot of companies maybe
lose some of that momentum that they have had through the interview process. It’s also a really important period of time too. Yeah. It’s a confidence builder or breaker. Yes. If I got hired by a startup and I was enamored with the team and decided to take that incredibly risky bet, and then my ramp or my first 30 days felt very unstructured, I’d be very paranoid about the decision that I’d just made.
Because it’s like, hey, if this is unstructured, what else am I going to uncover here that’s also unstructured or not thorough or thought through or effective or measured appropriately, or- and these aren’t like- most people that are hiring folks, these are not hard things to solve. They’re tedious.
But they’re incredibly important, right? So it’s like the unsexy work that can actually have the biggest impact. So it’s not higher level math. You just have to put the time in to understand what a good candidate and onboarding experience looks like, and then just run it and iterate as you keep hiring.
What’s the most important piece of wisdom on hiring you wish you’d known?
There’s a lot because I think like everything else, you get better by making mistakes, right? You kind of find all the rocks in the bay with the bottom of the boat. I think the importance of back channels. I think I can speak for myself, I didn’t do it well enough in the early part of my career and got snake bit.
And I don’t think it’s a lot of people’s default setting to do it because. They usually staple it to the end of the process. Candidates leaning in, maybe you’ve already sent the offer. Maybe they’ve already accepted. And now you’re doing back channels and you’re probably just leaning on the ones that they gave you.
And like most people, even if they’re really trying to be intellectually honest, if they’re in the names they gave you, there’s like a 1 percent chance they’re going to get a negative or a very candid back channel that’s not usually glowing. So to me, it’s like, you need to almost weigh the back channels as much as the candidate experience, because especially with Go-To-Market hires, they’re paid extroverts
for the most part. They’re going to be very good at interviewing. Salespeople are very good at convincing people of things, including convincing them that they are a good candidate for a job. But you really need to go look at their past behavior and performance because that’s probably the best indicator of their future performance and behavior.
And it’s again, this is the type of thing that is very tedious and in the weeds, wildly important and rarely done. And for the founders in our portfolio, I’ve simply just put together a list of backchannel questions that I use or that I’ve aggregated from people that are better at me at recruiting.
And it’s simply just like, hey, what was this person’s impact on the company? How did they react when they were under pressure? What would their detractors say about them? Would you agree with those comments? How did they change the most in their role, when you were working with them? What do you think they still need to change?
And then for every one of those questions, simply can you elaborate on that answer? Can you give me an example of that? So really just trying to actually uncover useful information, right? Would you work with this person again? Is there anything that we didn’t cover that you think I should have? If this person doesn’t end up working out in nine months, why do you think it would be?
You also can’t phone in the back channels too, where it’s like, “Hey, is this person the worst person you ever worked with? No. Okay, great. Then justify my decision. Let’s move on.” You know, close the candidate. That’s probably the biggest thing. And then I’m a big believer in the school of recruiting.
I came up under at Mongo, which is off the John McMahon tree and with Dave there and folks I reported into on the sales team, like Carlos. Just looking for things like intelligence, persistence, coachability, adaptability, integrity. I usually will bucket my interview questions under those chapter headings, because I think that’s what’s most important.
It’s important to walk through someone’s progression of their career to understand why they made decisions going between companies or taking opportunities or how they found them. It’s way more important to dig into the aspects that I just mentioned, because again, that’s what you’re really getting in recruit.
Like you’re not recruiting somebody’s past company logos or that company’s success. You’re recruiting like this individual as they exist today. So at the early stage of company building, that’s what really matters, right? It’s just like incredible persistence. Integrity is key. Are they adaptable? Because the company is going to reinvent itself and get rattled every nine months.
And are they coachable, you know? Can they actually take feedback and they learn from their mistakes? Have they failed? Maybe that’s the other important one Tom. I really get nervous about resumes and when I interview people that just seem perfect. Wherever they went to undergrad is a known school.
The logos they’ve been at have all done well. They got the president’s club on their LinkedIn. To me, it’s like, hey, when’s the last time you completely blew something? When’s the last time you just absolutely failed? Talk to me in depth about that. What’s the last deal that you lost? Not the company or the champion,
like you blew it and it’s on you and walk me through that and what’d you learn and what happened? And if you don’t have good answers to that, what’s the most competitive thing you’ve ever done? What’s the hardest thing you’ve ever been through? You can’t really measure for adaptability if somebody is never falling down on their face and had to actually get back up.
And if you’re going to work at the early stages of company building, falling on your face becomes like a regular habit, even in spite of your best efforts. So you have to be pretty calloused to survive. I just don’t- I get nervous when I look in the portfolio and I look at a sales team and it’s like, hey, everybody here has worked for company- even companies that have never had that hard of a time.
And now they’re at an early stage startup. So it’s like the same ocean, but you’re in a raft instead of a cruise liner. And you’re like, hey the ocean feels a little different than where I’m used to. So you want to be able to get all of that out early and not figure it out when they’re already at the company.
Some great insights there, Liam. Can I just ask to wrap that up on the back channel? Of course, these are always primed when their reference is given, right? These people are going to be saying good things about the individual because they’ve been chosen to do that. Whereas though, if you seek a particular persona outside of whatever’s being asked of them in those references or someone else in addition and what you might be looking for there.
Yeah. I’m going to talk to the people they gave me, but second, usually I’ll try to find someone they worked with or someone that reported to them or someone they reported to. It’s not that hard. Again, like I think- if you can’t recruit A players and become an excellent recruiter, you’re going to have a very short or a very turbulent career in SaaS sales.
And this is actually the work that matters, right? It’s not memorizing interview questions and seeming stoic and intimidating in interviews or challenges. It’s like doing the work of okay, they were at Okta from 2016 until 2019 on the enterprise team in Boston. Who else was there? This is 10 minutes on LinkedIn of work.
Send a bunch of people notes “Hey, confidentially, we’re looking at this candidate for a company in our portfolio. I’m just curious if you worked with them. And if so, if you’d be willing to give me five to 10 minutes, just to ask you some questions. This is a really important decision for them and for us, and I don’t want to get it wrong” right?
You’d be amazed at how many people would say like, yeah, I’m happy to give you five minutes or you know. And then same thing, if they reported to somebody or if they worked with them. And then you just have to have questions prepared that actually matter, right? It’s just like any other sales opportunity.
Don’t go in and ask close ended, simplistic, biased questions, right? Is this person good at sales? Are they a good seller? Can they qualify? You’re not getting any usefulness out of that. So actually spend the time and do that. A lot of salespeople with the paper process, for example, have learned through mistakes that you don’t do that.
You don’t wait until the last step to get that started, right. Back channel to me is the paper process of interviewing. If that analogy sticks, don’t wait until the last minute to do it. If you’re feeling good about a candidate, if they’ve made it into your top three, start. You don’t need their permission per se to go and contact people, especially if you may have connections in your network
to ask about their experience working with them. So I just can’t stress it enough. That’s actual data of how this person has performed in a role. Everything else you do in an interview setting, whether it’s sales challenges or- it’s all theory. It’s all theoretical. They’ve never been at your company.
You have no idea how they’re going to react inside of that ecosystem until they’re there. So what would you weigh more on a scale? To me, I’m going to weigh like things that have actually happened and people they’ve actually worked with much more than, you know, theoretically what they would be as a head of sales at this company. Couldn’t agree more.
Not to mention the, sort of the network building element of the back channel, you know. You’re able to then have someone else in your network through this conversation that could potentially be quite good for someone else down the road. So it’s good. It’s an always be recruiting posture. I know that probably, you know, is like making people wince hearing that cause it’s a platitude. But
I’ve had recruiters do that to me. And I am always like, hey, that’s like good on you for doing that. Right. I’ll give a back channel and they’re like, hey, you seem great. Would you ever be open to- and I’m like, no, but like great approach, great tactic. That is what a good recruiter and recruiting looks like.
Because just like you can’t have enough pipeline or pipeline coverage. Again, recruiting is an ever present need at any company at any stage, right? And if it’s not now, it will be in the future. And if it’s not at this current company, it will be at your next company. And if you don’t want to be an IC forever, you need to get good at this and you need to grow a network you can pull from.
So why not just get things started? Even if you’re recruiting SDRs or first line individuals at the beginning of their career, cut your teeth as often as you can, and just have this be a muscle that doesn’t ever get fatigued.
Sound advice, Liam. Liam, thank you very much. I think, a lot gained here. I’m excited to get this out. So thank you again. Yeah, of course, man. I hope it’s useful. Wonderful. Thank you, Liam.
