Sam McKenna
Just not having to ever do that again is... I mean like that's worth it.
Pouyan Salehi
You're just selling the dream on all fronts. Sales without having to do cold calls, leadership without having to do forecast calls.
Ross Pomerantz
I know what paradise is this? What utopia?
Pouyan
What did we walk into here? This is a whole different type of reality.
Ross
Sounds like Valhalla.
* Beyond Quota Intro *
Pouyan
I'm Pouyan from Scratchpad. We've got Corp with us, as always -
Ross
As always.
Pouyan
And I'm really excited for our guest today, Sam McKenna.
Sam
Hi, guys, thanks for having me.
Pouyan
Why don't you tell us a little bit, Sam, how you got into sales in the first place?
Sam
I think you guys are probably in the same boat. I fell into sales. I wasn't, you know, six years old, new to the states and thinking about how I can't wait to be a salesperson. In fact, I realized too the most pivotal jobs I ever had were jobs I actually turned down at first. So sales was that. I got offered a job to be an account manager. And I was like woof. Cold calling and sending sales emails and no thanks. And I was a master negotiator in my young age and asked for a whopping $5,000 more in base salary, which they gave me I was very, very excited about -
Pouyan
I'm sorry can I interrupt you and just pause there for a second. What you just shared is more than what most folks know. I just want to get this right. You turned down an account management job because no thanks to cold calling. So you actually knew what it was?
Sam
Oh, yeah.
Pouyan
A lot of folks we've talked to are like enamored by this title of business development. Gosh, that sounds magical.
Sam
I totally knew what the gig involved. And in fact, I hated for the first like year to 18 months of the job, I hated so much [saying] I was in sales. I felt like it was a derogatory thing. So I said I was in business development. And everyone's like, you're not in business development though you're in sales. And I'm like, SHHH don't tell anyone. But yeah, I think the only exposure I really had to sales, like true sales was like Mary Kay. And I'm just gonna hustle people into buying my crap so I can pay my mortgage. And that sounds awful.
Ross
How did you know about sales? I mean, how did you know like anything about sales? Like where did you learn that?
Sam
Well both my parents were entrepreneurs. My dad managed a bunch of really enormous hotels. He was the general manager at The Waldorf Astoria in New York City in the 70s. So I learned a lot about that. And then my mom ran a series of businesses. So how to sell, what to do what was involved in it, learned all about that from her, and then just got early exposure to sales technology and what that selling process was like. I had friends that were at DuPont that were doing this and it just sounded, you know, again, it sounded like we're hustling people into buying stuff for our own benefit, which is the opposite of everything I stand for. But I think it couldn't have been a better fit on my side right? Like it was a perfect puzzle piece to exactly what I'm really good at.
Ross
But knowing that, you still did it. Or thinking that, you still did it. So was it just a lack of options here?
Pouyan
You read my mind here. Like you knew exactly what you were getting into.
Ross
You chose this life. What is wrong with you? Why would you do that?
Sam
So when I moved to DC in 2007 It was really hard to find a job, right? Like we were going into 2008 and it was a really, really terrible climate to be in. After a couple months I couldn't find a job so I took a job - I actually never talked about this on a podcast before - but I took a job at Pottery Barn. And I actually loved that job. If it actually paid normal things I'd probably still be there. I loved working there, but after like insane weekend and night hours I'm like I have to find something different. So I fell into a marketing role. Don't laugh at me Ross! And then 2008 rolled around I got laid off, but the cool thing about that is like when I interviewed for the sales role, they were impressed or whatever and they really wanted me so they said you don't have to cold call. We'll let you come and do everything else but no cold calls whatsoever and I was like, okay, that I think I can handle. Let me take a gamble here.
Ross
Do you feel like account management is sales? Or is it kind of like a little watered-down, soft, like you can't say fall on your sword, type-version of sales?
Sam
First of all, I'm offended by that, but second of all, here's what I'll tell you. For me account management was cushy. I had a base of clients I had people I could build relationships with. I knew how to build rapport. I knew how to ask for business. I think that account managers get a bad rap because they just wait for the renewal to come in. But it can still be, especially if your account managing for enterprise deals, it can still be a hustle and grind to just figure out how to expand. But when I got promoted to net-new enterprise sales two years in so I never did SDR. I never did any of that stuff. And I was terrified, because there's no way to hide. You have no clients. You have a book of business and good luck. And that was scary as shit.
Pouyan
So tell us about that. Because you had a pretty awesome run. You somehow skipped the line on cold calling which was masterful -
Ross
Yeah, everyone here is gonna be like how?
Sam
Working for a small company was it. The leaders there didn't even have time to think about what you were doing to get your activity in. They were so over-extended on everything they had to do. So it was just like, go figure it out. It was one of those environments where it's like, here's your book, make it happen. I will say the cool thing from the account management perspective and I think something that really led to my success is when I was terrified of moving from expansion to net new, my CEO was like, you can take three accounts with you. There are three accounts that are unassigned, you can take those as a base. And so I looked to see where we had a great install base. And we had three of the largest law firms in the world working with our tiny $25 million company. And so I basically called up their CMO and I said, Hey, I'm gonna take over your account, I'd love to understand why do you work with us when you could work with anybody else. And then the cool thing is social selling started early for me. I met with one of the CMO's Jim Durham, who was super, super nice and told me all the reasons why they use us. Got exposure to what we impacted at the C suite level. And then at the end, because I took the time to build a relationship with him, he said look at my LinkedIn network. If there's anybody that I know that you want to meet, just tell them, you're a friend of mine and they should take a meeting with you. And I literally went back to our office in Richmond, Virginia, I stayed up the entire night and I did exactly that. I went through his entire network through every law firm that I had that was in my book of business and then found the common connections and sent that. Threw it in the subject line. Got a shitload of meetings. And then in two years, I signed 43 law firms and they got recruited away.
Pouyan
You skip the line on cold calling, entered into account management, moved to net-new business. But, you know, it looks like you had an awesome run of actually going into management and then leadership. Tell us about that.
Sam
Yeah, I think when I got into net-new and I got the 43 accounts in two years, our company actually switched gears and resold a different product and I actually quit. The product was so bad that we were reselling that I was like, I'm gonna burn all my bridges. But my CEO was like, it sucks that you're gonna leave, but you're incredible. So he actually called up the VP of a company called On24, where I spent six or so years and was like, she's leaving if you want her, go get her. Because that's what we were originally reselling. So I got recruited over there. And then that's where #SamSales started because I would give all this sales advice and then my boss's boss's boss would be like, Oh, I never thought to do that. And I'm like, well... why are you sitting there, and I'm here? So I started to post and build a brand on LinkedIn, do all that crap. Then I realized I wanted to be in leadership, you know, other people's wins were as sweet as my own, like, I really was inspired by helping other people. And that's what I love about sales, too.
So in terms of going into leadership, I basically set our VP down. This was after the second year of, you know, I think I finished my first year at number two, second year, number one, and I'm always like, how do I get promoted? So what are your issues, what are you trying to solve for? And he gave me three issues, one of which was attrition, and one of which was making people feel more valued. So I created a mentorship program and onboarding program. We had nothing other than a culture club, which is the saddest name ever, which is why I'm in sales and not in marketing because that's all I could come up with. But it made impact. We tracked ROI and I got promoted, and then just kept, you know, crushing our quota of bringing on people that made President's Club. I interviewed 50 people before I hired my first rep Katie, who's now at Salesforce, and she obliterated everybody else, because we just worked in tandem really well. And then I was really loud on LinkedIn. Really loud about LinkedIn Sales Navigator and LinkedIn asked me to come to a testimonial. I peed my pants for a little bit with excitement. And then I was like, sure and played it cool. Much like when I got asked to be on this podcast, and then I went over there and basically fell off my stool with enthusiasm of the platform, and they're like, You should come work here. So I did and then while I was at LinkedIn, I broke my 13th sales record. And I was just like, What can I do on my own? I'm making ton of money for everybody else, I wonder what I can do on my own. And so I took the scary leap in the fall of 2019. To do that. I will say like, pro tip, you cannot be an SDR for six months and then decide that you're going to release your own playbook or guide or $999 system. You need some experience before you go out and talk about that.
Pouyan
You just crushed so many dreams.
Sam
And triggered you both intensely.
Ross
They all want me to come on their podcast, I'm like, Oh, my God. Like, if I did every one of those podcasts, I'd do nothing.
Sam
How do you say no to that, Ross? You tell me because I get these all day, every day and I'm sure you get it tenfold? How do you say no?
Ross
Honestly, it's really fucked up. I say you need to email my agent or Chief of Staff. They'll coordinate and, you know, the coordination just somehow doesn't work? I don't know why! I don't know why it never works out.
But I'm curious. What did you learn when you went into that management role? What kind of shifted in your perspective around like, you know how most reps believe leadership, management, whoever is in charge is like very out of touch, or they kind of lose their edge so how did your perspective change in that switch?
Sam
I don't know if this is a good or a bad thing still, but I never really saw that line, especially from frontline manager to managing ICs. I just really always felt like we were a team. And I think that leaders often think like when they're the leader, they can't tell you things, whatever. I was never that way with my team. Full transparency, super honest about what was going on. But I think what made me different, and I posted about this today, like, I was just pretty insubordinate. And what I mean by that is we've all been there. We have leaders who are like, give them a 50% discount! Get it in by the end of q3! And you're like, I'll see if it'll work. And then you absolutely don't do it. Because you know, it's the worst strategy on the planet. That's basically what we did left and right. That's how we always overperformed was by not listening to leaders that just didn't know how to do it. I think that that was it, like, you know, figure out how to still be, especially as a frontline manager, figure out how to still be in the trenches with your leaders, or your reps and coach them actually coach them on what to do better.
Ross
That's true. Most managers just kind of sit back. They're much more reactive to, "Oh pipeline's not looking good. Oh, your forecast and not exactly what I want to see." And then they get involved.
Sam
I think you've got a lot of leaders who just - and it's a lot of guys who were in sales for like six months and then someone in leadership was like, "You're not doing so well, but we think you'd make a great leader." And so they promote them to like manager, director, whatever! And I'm like, This person has no idea how to sell! The first time I was passed over for a promotion it was for someone else who had been at the company for three years and had never once had above 80% of his quota. Meanwhile, I had President's Club like the last 2 years, and I'm like, how did this happen? So you have leaders who don't know they don't know how to sell, they don't know how to engage, right? Or you have leaders who are great at that, but they're not great at operational stuff. And I find the seller leader is really rare. The operational like "here's your forecast and the run-rate" is very common. But the “how to dazzle” a client, how to actively listen, how to just give a shit about another human seems to really lack.
Pouyan
But I do want to get into working for yourself, Sam, because there is a lot of glamour that seems to surround that. And you've now done it. So maybe you can share what that was actually like.
Sam
Full glamour. All I do is get facials all day. It is a grind you guys. It's so. Much. Fucking. Work. But it's the best job you've ever had. I'll tell you when I started the whole idea was I'm going to work part-time and work 20 hours a week, and I'll make half the money I made in SAAS and like that's enough for me. And that went out the window within a week, right? And I signed a few clients and then February of the next year - we started in September - February the next year, we hired our first person. And now we're an all women team of 14 and have 160 or so clients. We've done okay for three years in business. But the thing that people don't think about is like you don't set something up in a business and then let it sit. Like you're always reinvent revamping your website, your offerings, your pricing, your proposals, your pitch deck here, all of the decks that you present, right and then as a solopreneur, right, or as a solo salesperson, you are selling, you're managing, you're doing the finances, you're doing all of that and then you have to do the work that you actually sold. So it's more work, you know, than I've ever had in my life, but it's the best and I think that's also how we grew. When I was at my desk for 12 or 14 hours a day or working two additional hours at night, I started to think like, what can I shove off my plate that doesn't need my brain, right? So finances gone. Scheduling. Just scheduling me, right like you were saying Ross, gone.
Ross
Yeah. Gotta get that one out.
Sam
Yeah, forgot that, but I think the cool thing about this business is we don't have grand plans to be a 100 million ARR business like, we'll never be that. And frankly, I don't want to be that. I love the fact that we can impact awesome companies, awesome clients, and that we can also have a little bit of balance in our lives. Our VP of Sales just came over from a company called Cision. And I was like, one of the perks of you being here is that you will never have to be on a forecast call again. I just don't care, I don't care. We have enough predictable revenue, we don't need a forecast. I don't need to do any of that. I don't need to know what you know, whatever you've got, I just want to know how your deals are moving and what I can do to help accelerate them and that's it. And just not having to ever do that again is I mean like that's worth it too.
Pouyan
This is the dream on all fronts! Like no cold calls, leadership without having to do forecast calls.
Ross
I know what paradise is this?
Pouyan
This is a whole different type of reality.
Ross
Sounds like Valhalla.
Sam
Well, we'll see how long we survive. We might just be the new shiny penny that people are excited about then no one's gonna love #SamSales after this. But we're eagerly awaiting 161st client, something that rhymes with Scratchpad would be great. Who said that?
Ross
Sales are dope. Never ever stop selling. We love that.
Pouyan
We do this towards the end, but maybe we can fill it in right here. Why don't you drop a pitch for #SamSales here like what do you all do highlight that?
Sam
Make it cute. We have like 5-6 lines of business. We do every sales training under the sun, we help you build and re-org your entire BDR organization from techstack onboarding, training, messaging, all that stuff. Do everything on social selling, we write a ton of sequences. So you guys know the messaging that you get in sales emails is awful. So we help people write it based on data and our own style. And then I speak. I speak at a ton of conferences and all sorts of stuff like 100, 150 times a year, SKOs and all that crap. But I think the thing that's different about us is in our trainings is we're methodology agnostic. We don't do any spin, Sandler, any of that crap, like forget it. We just teach you how to be a human being. How to do your homework, how to show up prepared for a call, how to care about someone, who they are, what theywant, what they're interested in. And then everything is really tangible. So I just came from a conference and the feedback that I got was your session was the only one where I actually learned something that I can apply today. Everything else was fluffy. I don't even understand how you present for an hour and not teach someone something. Plus we're pretty energetic. Plus, I've actually been there, done that, as an IC and a leader. And we've got jokes. I made Ross laugh once I think so.
Ross
We got jokes.
Pouyan
Isn't it weird how to be a human, how to care and listen... Isn't that the curriculum of elementary school?
Sam
You would think so! Isn't writing an email and knowing how to spell the "there" correctly? Yeah, I mean, I think some of the stuff if you get it, you get it. But when we teach show me, you know me, we're like, here's how you break into a company. Here's how you do a little bit of research on the human and then write something in the subject line that'll catch their attention. So a guy submitted an example to us the other day and he's like how'd I do? And he talked about chocolate and baseball and if [the prospect] is excited about opening day of baseball in Miami. And we're like, what does chocolate and baseball have to do with this guy, I don't see anything on his profile? And he's like, well, I don't know, he lives in Miami and there's a baseball team down there and I figure most guys like chocolate... What?
And that's like 90% of what we run into. So it's, again, if you get it, you get it. But it's a cool thing. It's, you know, again, the stuff that we teach, like if even if you take one thing, you change the opening of your discovery call differently. You send a thank you note when you lose a deal. You ask for a referral proactively. If you just do one thing, you see immediate impact from what we teach. And that is how we get adoption from reps because reps are like holy shit it worked and we're like, we know, go do it again. That's, that's a little bit what's different about us.
Pouyan
I think you're spot on in that there's some basics that have seemed to be lost along the way somehow. And in some of those basics or those fundamentals just help you connect.
Sam
Like, let's say like we booked a call with Ben. And Ben was like, hey, I'm going to bring Pouyan onto our call. What I see most reps do is they'll get on, Ben will join and then we're like, "hey Ben... just waiting for your boss to join." They don't engage, they don't talk. They don't build rapport. And we're like, it's it's, it's, it's as basic as that! Forget multi-threading and negotiating and all of that. It's like, how do you even show up on the first date? Right? And if it's terrible, we've really got to fix that in the foundations of everything else before we really move on to the nitty gritty stuff,
Pouyan
There seems to be a trend of more folks getting into advisory positions, and I was looking at your LinkedIn, I was like, Whoa, like you've also got that. As an advisor to many companies, which is really cool, what's that experience like?
Sam
I think it's really cool. I think you have a chance to help founders figure it out. Especially first-time founders or even second-time that don't know how to sell, don't know how to operationalize, don't even know how to hire. A lot of these people come to us and say like, I want to hire a VP of sales, and we're like, you don't have a product yet so that's probably not a good idea. But the thing that I love about it is I feel like it's traditionally minimal time investment. Traditionally, we have an equity play in a company and we're just kind of gambling our time to see you know, if they do well, and then they sell. Some of the other ones are financial investments so we're making a play like go-to-market fund that I'm an LP in is a financial investment every year and then there's a few other companies that I've put some money into. But I think it's a really cool thing, because you get to feel like you can impact their growth. And then if they really grow or if they get acquired then it's a nice, serious payout.
Ross
But I was gonna ask Sam, what are you seeing around like the world of remote now. I can't imagine what it's like to be a little SDR in their shitty little apartment in New York trying to make cold calls. And there's no transfer of knowledge, like the tribal knowledge doesn't go to the next. All the things that you teach or the things that good reps do, like these new reps no longer get to see. What are you seeing or hearing from companies right now and how are they dealing with that knowledge transfer loss?
Sam
I think the biggest thing is how we're shadowing and then also how we're thinking about these BDRs getting to latch on to deal. So if you've got a BDR, right, like we're taking them through onboarding, we're taking them through all that training and everything. But I think there's a critical inflection point for those BDRs, right? If they do show some success and they do show potential to be an AE, what are we doing to train them while they're remote? Are we giving them a chance to go crack open an account, book that first discovery call, do all of that while the AE shotguns? I think that's a great opportunity to do knowledge transfer and also have that partnership, because then before dropping this BDR into hot water, you give them a chance to go and ride this out on their own.
I think the remote thing is, to me, it's huge, right? I've been remote for 12 years. I was LinkedIn's first employee in the US that was hired remote. Everybody else you had to work in an office and then have whatever extenuating circumstances. And it was a tough fit. Even being remote, not the knowledge transfer thing. But people being like, Why do you get to be remote and I don't?
Ross
Because I'm better than you. Next question.
Sam
That's what I said. I don't know why they didn't like me?!
Pouyan
You see that President's Club award right there?
Sam
Yeah, you see those trophies? But I think remote is where it's at. And there's so many people who are arguing about that whole idea of like, you know, we have to go back to the office, the knowledge transfer, things like that. I think if you make the baseline, we are gonna be remote. Work from wherever the hell you want to work. Here's where we have offices and support for you or wework memberships or whatever the hell it is or we want you to come in twice a week. I think there was an Adam Grant thing about that like maximum two times a week because all you really need to have that knowledge transfer. I think you can build that in. We don't necessarily have to be together. Now I'll tell you our entire organization is remote. We have people from Hawaii all the way to Dublin and everything in between. Half of our staff are military and expat spouses and they didn't know anything about sales or anything about SAAS before they started and we figured it out. You just have to have the right path to do it. What do you see? Do you think companies are failing that way?
Ross
I think that most of them are failing. I think many of them are trying but I think there's more of a psychological and mental issue, more so than I think it's the knowledge transfer. I think some of them can do a pretty good job of the knowledge transfer and the shadowing programs. You'll see sales teams all hop on the same zoom but like just be muted and kind of like be working together and have those conversations. But I think it's just for me, if I'm going to fail I want to fail around my friends who are also failing. It feels way more okay. Since sales is mostly a game of failing and it would be much harder - and I'm just speaking purely for myself - to stay motivated ripping 80 dials here by myself.
Sam
For sure. And especially new in your career. But it's like what to do beyond that, right? Because nobody wants to do the Zoom happy hour. Oh my god. Nobody wants to do the Zoom happy hour. And so how do you stay connected? How do you keep them motivated, while also giving them the freedom to do the stuff they're supposed to do every day?
