Pay Attention!

In this episode, we speak to Adam Jay, the Co-founder and CEO of Revenue Reimagined.

Adam shares his insights on; 
  • Sales leadership and team building
  • Evaluating product-market fit 
  • The importance of transparency and accountability in sales
  • And more...

Creators & Guests

AB
Host
Anis Bennaceur
Co-Founder and CEO @ Attention
AJ
Guest
Adam Jay
CEO of Revenue Reimagined
RM
Producer
Rory McDermott
Growth @ Attention

What is Pay Attention!?

Welcome to Pay Attention, where Attention's CEO and Founder, Anis Bennaceur, interviews some of the smartest minds in sales, growth, and product leadership.

Anis Bennaceur (00:03.284)
Adam, welcome to the show. Very excited to have you here.

Adam Jay (00:06.062)
Thanks for having me, man. It's weird to be on this side of the table. I'm used to being the one welcoming people to the show and seeing all the fancy controls. It's weird to be on this side, man. Thanks for having me.

Anis Bennaceur (00:16.11)
course, very happy to have you. At this time, we're sitting at the opposite sides of the table. I'm the one interviewing you and very excited to have you. Ladies and gentlemen, if you're listening to this podcast, I want to introduce you to a revenue legend here, Adam Jay. He is the co -founder and CEO of Revenue Reimagined, multiple time sales leader, and someone that I personally adore. Adam, thank you for being here.

Adam Jay (00:45.147)
You forgot the important one. It's the recovering CRO. Like we have like recovering addicts. We have recovering this and that. I'm a recovering CRO, which I'm sure we'll get into in a little bit.

Anis Bennaceur (00:56.714)
I'd love to know what that means. So yeah, I want to start with my usual question, which is, tell me about the three pivotal moments that led you to who you are and where you are today.

Adam Jay (01:11.17)
Yeah, so I think there's a few and I'm gonna go a little off script. The number one pivotal moment that shaped me as a human, me as a leader, me as a father, me as a husband. Those who are close to me know this, but most people don't. So I grew up in a family of addiction, right? My mom was an alcoholic up until the day she passed, excuse me. And my father was and is still a heroin addict.

And I could remember as a child walking into we lived in Florida. We just moved back here. was 17 years old. I used to do radio. So I did I did an overnight shift. I came home. It was five thirty in the morning. I was beyond exhausted. And my dad is laying in a bathtub with a needle in his arm and every piece of furniture in the house was sold, gone, sold for drugs, like gone. And I could only laugh because it makes you better. But like growing up like that.

really taught you what to appreciate and how to appreciate it. And I think that's fundamentally shaped me as a human being. So that's number one. Career wise, if anyone's listened to my podcast, they've heard me tell the story of like, I was turned down for countless promotions, right? Like I was a number one seller for years. I applied for a district manager position, turned down, applied again, turned down. And I finally had this wonderful, incredible leader, Whitney Parachak. She was our VP of sales.

She sat me down. I'll never forget it. It was at the San Diego Marriott marquee at a national sales meeting And she's like do you want to know why you didn't get promoted? Yeah, of course. I want to know and she looked at me. She's like don't ask questions You don't want the answers to I'm like no, I really want to know She said it's because you're an asshole and I'm like, excuse me She's like you're great at what you do But you have to tell everyone how great you are and you're not willing to share your secrets and it's always about Adam Adam Adam Adam

Adam and no one wants to work for someone like that. And that was a like, remember it vividly to this day. I could close my eyes in these and picture sitting there and seeing the water and it fundamentally changed the way that I lead, the way that I operate, the way that I talk about myself, my business, people, coach, et cetera of it's got to be less about you and all about them. And we talk about this when we talk about leadership a lot.

Adam Jay (03:33.634)
but it was, it used to be all about me and now I very much have this no asshole policy, not just for myself, but for anyone that we work for and work with. We get to choose who we work with, which is a very nice thing, but you can't be an asshole. The best thing you can do as a leader is to share your secrets, is to give back, is to help others. Because at the end of the day, I could share every secret I have about how to lead or how to be the number one rep and.

You and I are just going to execute it fundamentally differently, and that's OK. But if I can help you be a better seller, that's incredible. And then the last one, not taking recent events into account, which have certainly given me a new perspective on life. What got me into Revenue Reimagined? I was working for a nameless company. I thought I did all the diligence in the world, wound up selling a product and demoing a product that turned out to be vaporware.

Literally, we were demoing Figma and telling a customer like here's the product we'd go through the demo and if you don't know Figma you would never know right because all I'm clicking on is on the spaces that will click if you click on the wrong space you're gonna see nothing But when we were finally trying to close a multi -million dollar deal with coincidentally deal and they asked to see features and click in places that we couldn't click and the deal crumbled

I was like, I'm not putting my integrity on the line anymore. And I realized talking to people, this happens a lot more often than we'd like to admit. And that is what kind of led to my exiting startup corporate life and starting Revenue Reimagined with Dale.

Anis Bennaceur (05:14.53)
That is pretty wild. So today, as you work with different startups and you decide to partner with them, how do you evaluate whether they have product market here or not if you're going to put in your reputation on the line to help them grow as a business?

Adam Jay (05:18.284)
Yeah, it was.

Adam Jay (05:40.43)
It's a great question. So having product market fit is not a requirement for us to work with the company. And I think that's important. What is important when it comes to product market fit is that the founder and the executive team be very aware of whether they do or do not have product market fit, because the decisions that you make are going to be guided based on that. So we look for several things, right? Everything we do,

is done in this kind of mindset of bridging the GTM gap. And what do I mean by that? Oftentimes, we'll come in, we start everything with an audit, as cheesy as it sounds, the rationale is simple, and it goes back to selling vaporware. If we don't know the problems, if we don't know the truth, we can't help you. And our ethos is to decrease your burn and extend your runway while making revenue go up and to the right.

And if you're going to pay me what you're going to pay us every single month, and we don't know the truth, you are literally flushing money down the toilet and we won't take your money. So when it comes to product market fit, it's bridging that GTM gap. have to start with stabilization, right? Unfortunately, no one calls us to say, Hey, Adam, everything's going great. Please come help us. One client out of all our clients, I think got to us early enough that it's like, Hey, we want to engage you before we build out anything, which was

awesome. But generally speaking, we've messed up, right? We either had a mishire on a VP of sales, or we hired 27 people too fast, and please come in and fix it. So we have to stabilize first, which is the very first stage of the GTM gap. Then we're going to go to build foundation. And what you find is you still have a lot of founders who are in this growth at all costs mentality, where it's

Just go hire 712 reps and you know they'll just be able to sell it top down build it. They will come 12 reps quote a million dollars a year. We're going to hit 12 million this year. You're not PS you're not, but let's take a step back. We got to build the foundation. We have to make sure that we have the proper ICP, the proper buyer personas, the proper value proposition, etc etc etc. Once we do all that, now we could start looking at do we have product market fit?

Adam Jay (07:57.422)
How many initial clients do you have? Did they all buy because of the same reason? Can you validate that they all bought because of the same reason? Do we have those calls recorded? Have we interviewed them? Have we asked people, hey, Anis, why did you buy this product? Are you getting value out of this product? You then have to be able to prove the usage, right? We work with a lot of SaaS companies, and nothing amazes me more when I talk to a founder and they're like, we have 27 customers. They're all happy. They're all great.

And we go to look in, whether it be Pendo or whatever it is, and it's like, wait a minute. Of your 27 customers, like six of them have actually logged into the product in the past like 90 days. That's a problem. You don't have product market fit. So we have to really look at that. And then it's the value exchange. And I just simply ask customers as we're doing audits, if I were to take this away from you and rip this out of your tech stack, what would those implications be? And unless you could really articulate

how bad those implications are, you don't have product market fit. So we really work to help founders understand what's needed and to make those refinements to achieve product market fit before we'll get into that repeatability and ultimately scalability of hiring people.

Anis Bennaceur (09:13.004)
That makes sense. It's at the end of the day, the superhuman question, which is, if you are to lose this product, how disappointed would you be? Yeah.

Adam Jay (09:14.151)
Thank

Adam Jay (09:25.516)
Listen, shameless plug for what y 'all are building over there. It's no secret that I'm a huge attention fan. If someone were to say to me, hey, I'm going to turn off access to your attention tomorrow, what would you do? I would damn near have a heart attack. And that's product market fit. And there's a few tools I feel that way about. But there's also other tools transparently in my tech stack that we've adopted that I'm like, this is kind of cool. But if you took it away from me, I don't know.

Anis Bennaceur (09:52.876)
Yeah, difference between a painkiller and a vitamin, right? Just love that. And one of the other things that you mentioned earlier was that, you you don't want to have any assholes around you in your team. so whenever you'd hire a sales rep, how would you evaluate how big of an asshole they were?

Adam Jay (09:57.358)
100%.

Adam Jay (10:15.446)
You know, that's kind of the hardest thing to screen for. To me, it's a couple of things that I look for. Number one, and a lot of people don't necessarily look at it from the lens of, you an asshole if you do this? But like, are you on time? That's a huge one. I am a big believer that whether you're the CEO or the BDR, no one's time is more valuable than anyone else's. And if you're going to be late, just say you're going to be late. It happens. But I like to ask questions about how sales reps have overcome adversity.

how sales reps have dealt with difficult managers. Listen, let's face it, not every manager is a leader. It's sad. How do you deal with that? How do you deal with challenges? I like to do very specific role plays about like difficult customers and how do you handle that? What are your responses? And then I really like to dig into examples of how do you give back and giving back. And I ask it just like that, know, and he's give me two or three examples of just how do you give back?

I don't care if you're giving back to your community. I don't care if you're giving back to your church, to a charity, to other reps. Just show me that you do something that shows that you want to elevate and lift up other people. Doesn't matter what it is. And you'd be amazed how many people have no answer for how they give back. It's the hardest thing to screen for. It is the no asshole rule because unfortunately until you're in a difficult situation,

where you have to challenge someone or where their numbers aren't hitting and you have to push back or they have a difficult customer. Like you don't really know how people are going to react. And there are a lot of people out there sadly that I think have this great LinkedIn persona of like they're kind and they're wonderful and they're awesome. But if you do enough digging behind the scenes, you'll hear over and over again that they're an asshole.

Anis Bennaceur (12:06.393)
So how would you answer that question? What do you like to give back and who do you like to give back?

Adam Jay (12:11.182)
I love that. So a couple things. There's a charity locally called Big Dog Ranch Rescue that we volunteer at a couple times a month. Animals are near and dear to my heart. So that's just one way to give back. We also encourage, I have a 13 year old son to do the same. More professionally, I have four hours a month every month that I donate free coaching time to. It is a open Calendly link. It books up relatively quickly, but there is no charge. They are 60 minute sessions. You only get one, so someone can't come over and over again.

but that's kind of my way of giving back. And then we typically have one to what I'll call one and a half clients that we'll do some no charge work for that can't necessarily afford our services, but we really believe in the product so much that while I'm not gonna give you 20 hours a month, we'll do an hour here or there of coaching or we'll listen to some sales calls, no fee, no equity, no anything, just, like we wanna.

Anis Bennaceur (13:05.166)
was awesome. That was great.

Adam Jay (13:06.766)
It's important, man. It's important. We all got here because someone believed in us or our product or lended us a helping hand. And the day we forget where we came from and we think that we're better than everyone else is the day that you have no business doing what

Anis Bennaceur (13:20.622)
100%. We all tend to see so many people who actually surround themselves with mentors. And then when you ask them for any sort of help, they would very quickly dismiss things. 100%. And so there's the no asshole rule that you mentioned. What are some of the other common denominators that you try to find across your, let's say your top sales reps or anyone that you'd want to have in your team that you would

Adam Jay (13:29.912)
Crazy, right? Absolutely crazy.

Anis Bennaceur (13:50.52)
really value more than anything else. Yeah.

Adam Jay (13:53.592)
Transparency and candor are number one. I think people have this mindset that like you can't be direct again without being an asshole. I tell everyone that works for me in any way a few things. Number one, I actually work for you, right? My job at the end of the day is to be your administrative assistant. It's to block, tackle and get shit out of the way so you could be successful. Number two,

when it comes to working with folks is I can't fix what I don't know. So I need you to be brutally honest with me. And number three is I don't want yes people. I don't just because I technically sit here on an org chart and you sit here, although when I build an org chart, I do actually invert them. Doesn't mean that when I roll something out or ask you to do something that I just want you to look at me and say, okay, Adam said so this is a great idea. Now, what I don't want is for you in a room full of 50 people to be like, hey, Adam, your idea sucks.

Probably not the best way to do it I've had that happen but privately like hey like have you thought about this or have you looked at it differently or I have another suggestion how we could do this I Love that. I don't want people to just yes me to death Challenge me and push back in a way. That's inappropriate and that's gonna help you grow your career and me it me as well Number two is curiosity. I think that the most successful reps I've ever worked with the most successful leaders I've ever worked with

Anis Bennaceur (14:51.488)
You

Adam Jay (15:20.13)
have had this innate curiosity to know about everything in the business. How is the product built? Why is the product built that way? Why is the logo a lightning bolt? Like it's just questions that help you better understand who it is you're working with, what it is you're selling and why, so that curiosity. And then lastly is coachability. And I think that's the one that I look for more than anything else, is are you coachable?

I will take a rep who has limited sales experience, who's sold six months, whatever, who is coachable and hungry and wants to learn above anything else. We have a client right now that we promoted a solutions engineer, and he's a solutions engineer kind of by default. He used to use the product. He knows it really well, so he came in as like an SE role. He's never sold anything.

but he was so coachable and so hungry. He beat out people in the interview process for an AE role that had five, six, seven years of sales experience. And he's killing it because he is willing to try anything. He's willing to learn and he's willing to ask.

Anis Bennaceur (16:32.354)
Yeah, that's what we call over here, slope over intercept. And that is so much more important than people with X amount of years of experience, especially, would say, in the world where things are changing so much. Your buyers are changing so much as well. And you kind of always need to be on top of your game, understand kind of like what...

Adam Jay (16:39.245)
you

Anis Bennaceur (16:58.594)
what surrounds your business, your company, your competitors, your industry, and really have a strong ability to push things further too, right? Rather than just repeating a lot of the same things over and over again. So tell me, how, I wanna know, how is your day -to -day today, you know, as a fractional reader, as a fractional,

Adam Jay (17:23.502)
you

Anis Bennaceur (17:28.332)
revenue leader with all your clients versus, you know, sales director, revenue director, VP sales, CRO at one company where you used to be in the past.

Adam Jay (17:42.19)
That's a great question. A lot more stressful and a lot more hectic, but I'll be a little more specific. The context switching is hard. And I think that's what people don't really talk about when they go into doing fractional work or running an agency. Like today, I had a executive call with a client who's in the ed tech space. I had another executive call with a client who's in the recruiting space.

We then move to a client who's in the healthcare space. I, after this, I'm doing a demo for one of our AI clients in the healthcare space where I'm actually running the demo. Like I'm the AE, so to speak, which I don't do a lot, but I still love to throw the clothes, so to speak. So the context switching is hard and making sure that you are, and I teach this to AEs a lot, but like ruthlessly prioritizing and time blocking your day. It's so much more important for me now.

I don't know if I've ever shown you, like my calendar is like color coded. So like I can tell like every client has a color. So very easily I know what's coming up and what type of call it is. But making sure that you're prepared I think is even more important when you're working with multiple clients. The stakes are incredibly high for our clients, right? We are probably one of if not the most expensive in our space. Our clients demand excellence. There is no excuse of like, I forgot.

Or like I was on the call like no client one of the questions we get every time we do an engagement anise like I shit you not is how much time do we get with you, right? And then the next question is well, how many other clients do you have? So I know like what your bandwidth is And I won't get into how we answer those but what I will tell you is it is never acceptable to say anise I missed that because I had another client meeting or I can't take your meeting at 12 o 'clock because I have you know, Jack's meeting at 12 o 'clock like that can't happen

So managing the calendars is hard and I'm very blessed that I have two incredible partners that helped me do a really, really good job doing

Anis Bennaceur (19:46.776)
So how are you able to balance handling your clients' expectations versus lending your clients?

Adam Jay (19:54.284)
Yeah, so we, I think this is one of the ways that we differentiate ourselves when it comes to expectations, again, going back to the GTM gap, everything goes in these four stages. But what we have found works really well as we utilize an agile sprint methodology. So everything that we do for our clients, we run three week sprints, everything goes in sprints with very clear deliverables. And if you wanna put something in, we're gonna have to take something out and we're gonna prioritize it.

and what that allows us to do is number one, we utilize Monday for project management. So our clients always have full transparency as to what the team is working on. number two, we produce a very comprehensive report at the end of the sprint as to what was done, what wasn't done and why, what had to be pushed and why to make sure that we're staying on top of those deliverables.

And then to your last question of how do we balance new clients. So we have three partners, myself, Dale and Jake, and then we have a team of other GTM experts. For each one of our engagements, one of us always leads it. So you have a primary, one person is a secondary, and then the third person if needed. And then we have our team behind the scenes, but we make sure that we individually are leading no more than three projects at any given time.

Anis Bennaceur (21:13.506)
Got it. So if demand suddenly increased, how would you see things? Would you bring it more to your team? Would you reject some projects?

Adam Jay (21:23.96)
So that's a great loaded question. As far as partners and employees, I do not envision a world where there's ever more than Dale, Jake, and myself. But we do have a team of folks that are not partners that work on projects. These are vetted go -to -market experts that work directly for revenue reimagined that will help work on projects.

And our clients find this out during the onboarding and interview process, right? It's not like a niece hires Adam. You think you're getting me and then I pop Eric in. We're not deceitful like that. You always have access to one of us, but sometimes it's going to be the experts who are working on your particular problem. We have a head of outbound. You don't, my hourly rate when it breaks down to it is way too expensive for me to be writing sequences. You don't want me doing that. So we have someone else doing that. Now I know you'll tell me we shouldn't write sequences and every email should be one off an individual. could talk.

to. And we do turn down clients. We turn down clients for a few reasons. Number one, we don't work with assholes. Number two is that expectation alignment, right? We met with a client the other day who is roughly 700 K and ARR and he told me that his goal in hiring us by the end of the six month engagement is he needed to triple that and that needed to be guaranteed in writing. I can't do that for you. Maybe doubtful, but I can't. If we can't align on expectations.

and a client isn't willing to put in 100 % effort and listen to our advice, then we're probably the wrong fit. We have never turned down a client yet, knock on wood, for bandwidth purposes, but I think we also try to be very good at when we onboard clients, not onboarding more than one at a time, et cetera, et

Anis Bennaceur (23:13.442)
Got it. There is also a common misconception around agencies just giving ideas versus actually doing the work. How would you like to address that?

Adam Jay (23:14.455)
Thank

Adam Jay (23:20.014)
I believe the headline on our current website says we are not consultants were operators I think I posted about this. I think I actually wrote about this in this week's newsletter There are a lot of fractional gurus or agencies out there

that will charge you 10, 15, 20 grand a month to produce a pretty slide deck and tell you, you should try this or you should try that. We're very much hands on keyboard operators, right? Like I said a minute ago, I'm doing the demo for this next client. Not because I live to do demos. I mean, don't get me wrong. I love the thrill of the close, but to get that real in the moment client feedback and listen, anyone can listen to a recording. I get it.

but to actually test the talk track with my verbiage, my tonality, my expressions and see what works and what doesn't is something that you can't get by building a slide deck, not sitting on executive call meetings, not listening to AEs, not doing one -on -one coaching. You can't build a business that way. What you're doing at that point is just recycling someone's old playbook and saying, hey,

You should do weekly one on ones and your discos should start with this and your demos should follow this flow. mean, that's great, but we could go Google that what we get paid for is to actually be in the trenches to do the work to try the work to build the revenue model. And I want to be clear. It's not that we're doing for you. We're doing with you, right? Like I'm not going to build your three year revenue model, hand it to you and say here, I'm going to show you how to build that, how to get the numbers, what you need to look for.

We're gonna go to your board meetings with you. We're gonna build that board deck with you. I think that in today's economic climate, anyone who wants to charge you money for a slide deck is someone that you should immediately thank for their time and go on to your next event.

Anis Bennaceur (25:23.438)
I love that. And so towards the end of your tenure with a specific company, what do do? Do you help them hire a full -time sales leader or how are you thinking about things?

Adam Jay (25:38.766)
It depends on the company. It depends where they are from a revenue perspective and where they are from a GTM gap perspective. So there's a couple of ways we do it. For companies that are ready to scale, that are ready for a revenue leader, we do help to hire and bring in a revenue leader without an extra 20 % that you would pay an executive recruiter or anyone else. And we caveat that by saying, listen, you don't have to use anyone that we bring in.

And anyone that we bring in, the caveat is I can get you the interview, but I can't get you the job. And the process needs to be run the exact same way as whether I was referring that person to you or you found them yourself or an executive recruiter found them for you. But I think there's inherent value in knowing that anyone we bring to the table is trusted and vetted from our network. On the flip side, there are companies that aren't ready to go spend that kind of money on a full -time revenue leader.

And in that sense, what we typically do is scale down the engagement to one of our coaching engagements where either, you know, typically the founder will continue to lead sales and lead revenue and or that AE that's being groomed to move from individual contributor to leader. I believe you had one of those as well where we're trying to coach them and groom them. And we'll work with that person also in a scale down, reduced capacity where we'll do an hour to a week of coaching.

we'll review the things that are important for them async, but we won't be as involved in the business until such point as they're ready to hire.

Anis Bennaceur (27:09.432)
So in the latter case, what are some of the specific traits to look out for when promoting an individual contributor to a manager or a leader?

Adam Jay (27:20.406)
Yeah, it's I like the word leader. I'm a big believer that managers are for factories. Managers manage process, leaders lead people. For me, I think the first thing is like people who lead without the title. What I always look for is someone, you know, let's just call it a sales rep who steps up, you know, who has ideas, who, you know, offer suggestions on how to change the process, who's looking at things from a more holistic business perspective. It's that person who innately puts the company first.

versus themselves first, and that's very, very hard to do. Someone who wants to coach other people without asking how much money am I gonna get for this or what percentage of the commission am I gonna get for this, there's just this inherent desire to coach and lead. It's the learners, it's the people who come in and they're like, hey, I read this book or I saw this article or I saw this about the competition, how could we address this? It's the people who are stepping up before they're asked to.

Or the top qualities I look for when promoting for someone and then lastly in these it's the people who ask for it Like you don't get what you don't ask for I can't promise you that I can make you a leader today But what I can promise you is if I hire you and you tell me hey, I want to be a sales leader I want to lead a team. I want to even if it's I want to be a marketing leader Whatever it is. It's my job as a leader to get you wherever you want to go

So if you put in that effort and you lead without the title, without the money, without the actual job description, I will give you my all to make you that leader when that time becomes available. I will have you shadow me on calls. I will ask for your input on things that I'm working on. The leadership development is the thing I love the most and that I get to do the least of.

Anis Bennaceur (29:07.234)
So I have a question there in those specific cases. When you promote an AE to be the leader, right, you end up having inevitably some jealousies from their peers and people, you know, threatening to quit or actually quitting. How do you deal with that?

Adam Jay (29:25.026)
Yeah, that's a tough one. It's unfortunate that people would quit because they feel that either the role should have been theirs or that's probably the most common one. To me, I think it's setting expectations early and often. I think it's when you have someone that you identify isn't going to be the leader, who wants to be the leader. And I had it happen to me, right? You owe them that.

conversation of like, listen, I want to be transparent with you because I'm committed to your career and your success. And me letting you think that you're going to get this role either in three months or six months isn't fair to you. I want you to be successful here. And I'm committed to doing everything I can to make you successful here. Maybe that's being a leader one day, maybe that's not. But in the short term, that's not going to happen. And this is why. And if that

Anis Bennaceur (30:17.272)
Mm

Adam Jay (30:21.962)
is the only thing that you want, then I owe it to help you exit gracefully. And if you leave on good terms and you do everything, like I will give you the most glowing reference in the world. But by letting you think you're gonna get that and then blindsiding you by giving it to someone else. Number one, I'm doing you a disservice and number two, I'm doing myself a disservice, because then you're gonna huff and puff and stomp off and quit and huff. And that's not good for

Anis Bennaceur (30:48.587)
Yeah, totally agreed. And that comes back to the earlier transparency that you were talking about,

Adam Jay (30:54.67)
It's hard, man. It's hard to have that conversation with someone who wants to be a leader and tell them that like, it's not you. And I went through it. I'll never forget it. And like it was even before the asshole thing. was something totally different. I just I wasn't the right fit for that role. in my younger self, I did take it personally. Right. And I did stomp my feet and like leave. And hindsight being 20, 20, I shouldn't have because I could. There was so much more that I could have learned.

from the leader that they brought in, that was the exact reason I wasn't the right person.

Anis Bennaceur (31:29.88)
So related to that, know that you worked at Toast, right? It is one of the fastest growing startups of our era. How has it been being in such a fast -scaling machine? What did you learn? What were some of the things that you realized that you should redo in the future, you should absolutely not do again? How has that transformed you in any way?

Adam Jay (31:59.63)
Toast was an epic time of my career that unfortunately COVID impacted. I think Toast is one of the best companies that we could all take insights from. I think from a product perspective, if I was running a restaurant, there is no platform I would run my restaurant on other than Toast. What would I do again that I

Adam Jay (32:28.078)
You talk about this a lot and toast isn't at the place that they could do this anymore But when I was there it was all about doing shit that didn't scale right like so every day every every district manager So toast had field sales So we had district managers throughout the country and then every regional vice president who oversaw the district managers We arguably operated as our own companies like you want to go try something the special pricing this promo like this way of selling like Go do it prove it works, and then we'll replicate it out through the company

much easier to do as a series B company than a public company. But doing shit that doesn't work, I think, or doesn't scale is something I've taken with me now with all our companies. Again, stabilization, foundation, repeatability, scalability. Right now, let's focus on revenue and how we could do that the quickest in the most efficient way. That doesn't necessarily mean we're gonna be able to scale this over and over again, but let's try to stand out. So I think that one's important.

Toast was really big in these on no assholes. The way that they hired was designed to weed out people who weren't collaborative, who weren't team players. They very much had no tolerance for the lone wolves. And I think that that's something I take away from toast is like when you're hiring for people, culture above all. And it's where I learned the phrase and I use it a lot now. I'm not looking to hire a culture fit.

I don't need a culture fit. What I need is a culture addition. I need someone who is gonna really enhance our culture. And Toast did a really, really good job of that. What would I not do?

I don't think the way the pandemic was handled was great for many reasons, but one of the things that I think Toast didn't do well on and has since recovered on is they just, during the pandemic, weren't in touch with their employees in the right way. And neither were a lot of companies. But I joke about this a lot is we, who it was doesn't matter, but there was a message that would go out fairly frequently when in the height of COVID of.

Adam Jay (34:37.271)
just go take a walk and calm down and everything will be okay. And like, if I was told to take a walk one more time, I probably would have thrown my laptop through the window. So I think it's really important as you scale to still remember that you're managing people, right? It's not just numbers. We're always leading people and people have to come first.

Adam Jay (35:02.828)
And then just like rewarding your people man, like Toast did a really good job of rewarding those who did well and recognizing is probably a better term than rewarding. Because it wasn't about, you know, here's a bonus or here's some equity. But like if you did something really good, you could guarantee you were going to be shouted out widely and loudly. And I think as I've gone from company to company in a fractional role and full time roles as well, like

Salespeople thrive on recognition, right? We all have big egos. We all like to hear our name. So to know that you did something really well and have that shouted out, I think is something that I definitely take away.

Anis Bennaceur (35:41.73)
Yeah, over here at Attention every week, each one of us has to shout out someone in the team for doing something incredible. And people just love being shouted at.

Adam Jay (35:52.428)
Yeah, it's important, man. It's important. People like to know they do good work. I like to know what other people are doing that I might not be so close to that really impacts the business.

Anis Bennaceur (36:04.206)
100%. So one of the big talks this past week, I don't know if you saw it, everyone was talking about this Paul Graham article called Sound Remote. Have you seen it? So it's about a, common wisdom tells you just to hire managers, you know, in Silicon Valley. And I know how much you don't like that word, but treat, you know, managers as a black box. You give them their goals and objectives and they just,

Adam Jay (36:14.304)
No.

Anis Bennaceur (36:32.578)
take care of it and you don't interfere with what they do as a founder, as a leader. And then so it was Brian Chesky who was giving this talk at Y Combinator in front of everyone else and saying that as a matter of fact, their results weren't good when they were in manager mode. And as soon as they went back to founder mode, which is, you know, getting a lot deeper in every single process and every single thing talking.

getting a lot more involved as a founder in the different units. Don't just talk to your direct reports, but actually, you know, skip different levels as a founder. Things get much, better. And so as Paul Graham released that article on his website, just everyone over the entire weekend on Twitter started talking about it. I think.

Adam Jay (37:24.098)
That's why I don't know about it. I'm not on Twitter.

Anis Bennaceur (37:28.438)
And then I think Twitter is for founders and then you have a lot of leaders and C -level execs actually on LinkedIn, but I think a lot more people are going to talk about it in the next few days on LinkedIn. What are your thoughts on that?

Adam Jay (37:42.69)
Yeah, so I selfishly pulled up the article while you were talking. I'm a huge believer in skip levels, always have been, you know, as a C level myself for many years. My wife who also runs customer success for a very large organization. I'm a big fan of keeping your ear close to the ground. You have to balance keeping your ear close to the ground, knowing what's going on level or levels below you would not

overstepping your leaders. And I think for me, like all my direct reports always knew that, like once, and I do once a week, I'm going to do at least one skip level with someone on your team. It's not to overstep. It's just to keep my ears close to the ground to understand what they think, what they feel, what's going on and where I could, again, block, tackle and get shit out of the way to make you all successful. I think that the founders who can do this, and I like the term founder.

and stay close to things without micromanaging and without over being overbearing and then take what they're learning in these skep levels, in these conversations, in these meetings and bring it back to their ELT, their executive leadership team meetings from a point of coaching, development, insight and to bring suggestions, not dictations, not demands, but suggestions.

I could see how they would be far more successful because what these folks are doing is putting themselves in a situation where they're not allowing people to operate in isolation and then they're not finding out about things that can cause issues or problems too late when by the time they have to get in, it's a shit show.

Anis Bennaceur (39:30.318)
Yeah, 100%. So as a founder, should also be eliminating as many bottlenecks as possible for your leadership, assisting them as much as you can. 100%. Great. So I think we're about to hit the end here. I would love to ask you one last question, which is who are three people who deserve a shout out and should be potentially invited to this podcast?

Adam Jay (39:35.278)
Every day.

Adam Jay (39:59.278)
I am not prepared for this one. And I will not. I'm not going to use the typical, ask Dale and Jake. Number one, one of my mentors and one of my friends to this day, Ross Niber, who runs centralized go to market strategy for toast, one of the most brilliant go to market rev ops sales minds you'll ever meet. has led sales, he's led rev ops, he's led BD. Absolutely.

Anis Bennaceur (40:03.17)
You

Adam Jay (40:29.026)
brilliant human being brilliant individual. So that would be first. Number two, I don't think RevOps gets enough credit. And I think RevOps is a very important hire. And one of the geniuses of RevOps, in my opinion, is Rosalind Santa Alina. She is a RevOps.

like will blow your mind with all things rev ops. think that she would be an incredible, incredible guest. And then lastly, I don't think people put enough emphasis on branding and messaging and having proper branding and messaging and how that ties in to sales, to success, and to growing a company. And Kristin and Annie, who are the co -founders of a company called Decoded Strategies, are amongst the best of the best in that space that I think would add a ton of value also.

Anis Bennaceur (41:20.226)
Awesome, we'll make sure to invite them to this podcast. Adam, thank you so much. This has been a real pleasure. I'll see you on the other side. Bye.

Adam Jay (41:22.402)
I love it.

Adam Jay (41:26.072)
Thanks for having me, man. Cheers.