Sales Leadership, Team Building & GTM Strategy with Mark Kosoglow

The number one thing you need to do is just talk to customers, man. I talked to like 70-some-odd people before I even like wrote down my first idea for Operator. Like, by the time I was ready to write it down, I didn't even need to write it down. I just knew what it was. And, uh, and then we've very much iterated a lot since then because if you ask people what they want, according to Henry Ford, they'll ask for a faster horse. They don't, they don't know that they want a car. So If you get to faster horse, your job is to think of what is car.

I'm excited to say that I have Mark here, Mark Costoglo. I hope I said that correct. If not, I apologize, Mark. But I've been following Mark for, I wanna say since my SDR days in Mailjet when I did my 500 dials. Like I've been following you for quite some time.

I know.

Yeah, been since Outreach.io was like still new, new and all that. So really looking forward forward to having him today. If you don't know who Mark is, go right now. Fahima, if you can just drop his LinkedIn in the chat, go follow him. His content is fire. Like, he just does an amazing job of breaking down like how people are thinking about sales and launching a business and all of that type of stuff. So highly recommend it. I'll— or my colleague Fahima will drop it in the chat. But maybe Mark, to kick things off, do you just want to give a very high-level intro to yourself so anybody who doesn't know who you are and like maybe talk about your early days in outreach and what you're up to at Operator?

Sure, yeah. So, uh, thanks for having me, uh, Ayan. So listen, here's pretty simple. I'm a career salesperson. I'm a sales professional. I've started, um, selling professionally, uh, back when I was, uh, 16 years old and I got a job at a shoe store in a mall and I was lucky enough that my manager of that store actually taught me how to do consultative selling and laid the foundation of the right way to diagnose someone's problem and then offer them up a solution if we have one that could fix their problem and then help them understand why that solution is, is good for them. And, uh, you know, been selling ever since. I think most people would know me as, um, I was the first employee at Outreach.io. I led sales there till about $230 million and a $4.4 billion valuation. I went to Catalyst as CRO and helped them grow from about $5.5 to $10.5 million in ARR in about 14 months when they'd taken 5 years to get to $5.5. And then I'm currently the CEO and co-founder of a company called Operator that's trying to help people break through the noise of outbound communication and make sure that they are only reaching out to companies where they can prove with data that the company has a problem that you can solve and provide value for.

Awesome, thanks so much. Uh, we'll talk about operator because I do want to get into that towards the end, but like, let's start at the genesis. Um, guys, like, again, I can encourage you, go check out Mark's, uh, LinkedIn. He's got a really interesting story and how he started, like he said, in shoe sales, going to outreach. Maybe let's kind of start a little bit there, Mark. You had a very unconventional way of getting into outreach and then just B2B SaaS in general. What was going through your head at that time? Why SaaS? Were you not happy at the mall? Like how did you make that transition? Let's maybe, let's start there.

Yeah. And I'll try to talk from a founder's perspective since it seems like that's mostly what your audience is geared to. Yeah, perfect. And like what, why, what? Happened to me might be replicatable or relevant to you. Uh, listen, I, um, I had, uh, become the youngest sales director at a publicly traded, uh, billion-dollar revenue company that sold stuff to schools. Uh, I'd always been in education sales for the early part of my career, and, uh, uh, it— education sales is very hard, but it also is very boring. And what I mean by that is, is you can only sell during certain windows because kids are off in the summer and then there's testing periods and, you know, the kids are off during the holiday season in the middle of the year. And so there's only so much that you can do. And I probably was working, you know, maybe 20 hours a week because I'd really automated my team and how we were doing, and we were always a very high-performing team. But I was writing a sales blog in my, uh, in my spare time. This is back in 2013. And I met a guy named Izzy Gertzowitz in the, uh, that who's a, um, a guy in New York City. Helped him out, and then he connected me to Manny Medina. Manny is the CEO of Outreach, and I started doing coaching with Manny on his sales calls, his approach, how he did stuff, and we became friends. And after a little while, I said, why am I not selling Outreach? And he's like, well, we can't afford you. And I said, well, I'll do 100% commission. And so, uh, my first 6 months at Outreach were on 100% commission. I sold over $1 million in the first 6 months. That allowed us to raise a round, a seed round. We raised, I think, $2.7 million. And Manny asked me to build out the sales team, and then I just led sales until about 2 years ago, uh, for 8 years, almost 8 years at Outreach. So, uh, yeah, very unconventional way. I live in the middle of nowhere, Central Pennsylvania. I lived in a town of 5,000 people. Um, there was, uh, you know, nothing, you know, a good job in that area is low, very, very low, 6 figures. Anything around 6 figures is considered a really really good job. And, um, I had one of those jobs, but it just still wasn't getting me where I wanted to get to. And I'd always listen to podcasts about startups and, and how they worked, and I was just very fortunate that, um, an opportunity came along. And when it did, I grabbed on really hard and I worked my ass off and made sure that I made it work. But, um, from a founder perspective, if you're thinking about this kind of stuff, really, like, the lesson in it is there are really good, smart, hardworking people everywhere. If you think that you need to look at like where somebody's worked and it maybe it looks a little regional or it doesn't look tech enough or whatever, then you probably have a— you probably are going to have a very tough time finding the right people that you need. But if you kind of open up your mind a little bit and look for traits And I'm a big— I hire for traits, I train for skills. If you hire the right traits, then the person will usually find their way to success. If you hire for skills, then maybe or maybe not those skills map to what you need.

Awesome. Thank you so much for that, that rundown of kind of the career and how you ended up at Outreach and all that. So I guess maybe just to build on that, like, we have a lot of early stage founders here. Some are B2B, some are B2C, but like, you know, if we keep it fairly generic, like what are some of the kind of misconceptions that now you're wearing your founder hat, before you were wearing your head of sales hat, but like what are some misconceptions at early stage? Within the early stage, would you say, is there for sales and go-to-market? I can like maybe kick us off and say like, I speak to founders all the time and they're like, "Yeah, yeah, I just need to raise $2 million. I'm gonna spend $500K on ads. I'm a millionaire, buddy. Like I got it. I'll just put them all to my ClickFunnels, Russell Brunson, let's go." And you and I both know that's not the reality. It's about doing your dials, ops, ops convert into deals and deals convert into ones. And like there's a process to this. So I think for me it was like going through that motion and like realizing, oh my God, like I actually don't know a lot about this stuff and I have to learn more about it. But I'm curious to see like, or to hear, you know, when you did it with Outreach, you had probably one perspective and now you're doing with Operator, you might have another perspective and the landscape has changed. But yeah, like, what are some of these misconceptions you've come across and that you could share with some of our audience?

Yeah, I think that, um, the stage you're in really dictates the type of person that you need and, and what your needs of your, your company are. So if I take it like back to, you know, sub— let's call it sub-$5 million, uh, you're still probably searching somewhat for product-market fit. Your founders are probably still very involved. If you're a founder, you're still very involved in, in the selling of things, and that, that's all fine and good. But ultimately, the misconception that I see most often is that we need to come in and hire a leader, uh, or they come in and say we just need to hire a rep. And really, you, you could hire a leader or hire a rep, but it doesn't matter what you think you need. What you actually need is a doer. And a doer is somebody that just does shit. They don't sit around asking for help. They figure it out. Like, I didn't— I'd never used Salesforce before I started at Outreach, you know, over 10 years ago. I watched hours and hours of YouTube videos, and I set up our own Salesforce instance. And when I left 8 years later for a $230 million company, I would still say 20 or 30% of the stuff that we did was stuff that I created in Salesforce way back in the day. Maybe not that much, 10 to 20% maybe. And so that's the thing is, is like, don't convince yourself of what you need. Do I need a leader to build things out and to create processes? Do I need a rep that can like take what I'm doing and then do it, and then we can hire a leader after that? You just need a doer, like somebody that doesn't make excuses. Somebody like— here was my schedule for the first year at Outreach. I'd wake up at about 6 in the morning. I had like a pretty good morning routine where I do some meditation and reading and stuff like that. My first meetings were between 7 and 7:30 in the morning, and I would have back-to-back demos from 7 to 7:30 in the morning till 4:30 or 5 o'clock at night. And when I mean back-to-back, I'm talking 20+ meetings. Then what I would do is I would take my kids to sports practice, help with dinner, do all that kind of stuff. I have 4 kids at that time. They were all pretty young. Youngest one at that time was probably 14 years old. Our oldest one, the youngest one was 5 years old. And then I would come back, we'd have a little family time. I put my wife at the time and my kids to bed at about 10 PM, and then I would watch YouTube and build out Salesforce and do my follow-ups from 10 to 2 AM. And then I wake up the next day at 7 AM and start it all over again. And that's not like hustle culture. That's because it takes a lot of work to get things off the ground. And I was passionate about what we were doing. I had the energy, I had the support of my family, which helped a ton. And I was just, I just knew that, that I had a great chance to change the trajectory of my career. And so I just worked my butt off. And I'll tell you that, like, that's what I mean by the doer. The doer just does that. I didn't even realize I was doing it until way late afterwards when somebody's like, hey, You share a lot of old ops with you in here. How many meetings were you doing a day? And I kind of went back and looked at my counter. I was like, holy crap. So that's the thing that you really need. Don't convince yourself you need a rep or a manager. You just need another doer that can get some shit done.

You remind me of, have you watched Pain and Gain with Mark Wahlberg?

No, no, I never heard of it.

The scene where he just screams, he's in a seminar and he just screams with his biceps, I'm a doer. And what you remind me of, you just need people to get shit done. I am a doer. So that's, I 100% agree with you. Early stages stuff, it's— there's a grind, there's hustle, there's a lot of stuff that needs to be done. Just because you brought it up, how do you define product-market fit? Like, at what point did you say like, hey, Outreach got product-market fit? Was that on meeting velocity, opportunities, or closes? Or you're like, inbound is kicking in? Like, how did you identify that?

I think, um, product-market fit is like a very ephemeral, slippery thing. And I think to define it in a singular way is extremely dangerous because what it does is you kind of drive for that versus actually driving for product market fit. You know what I mean? Like, it's the same thing, like, if I have a headache and my doctor drives to solve my headache but actually have a brain aneurysm and they never actually do anything about what's wrong with my brain. That's exactly how product market fit works. Product market fit is something that you just need to be completely on top of. And I would say it's probably healthy to think that you never quite have it because that constantly gets you closer and closer to your customers and, you know, keeps you in that kind of like ever, ever rotating mode of like, I gotta keep getting better. But listen, if I was to like take a stab at defining product market fit, it's when you explain what you do to someone Do they get it? That's the first part. You'd be surprised, so many products, the person can't explain even what they do. I've sat on demos with new founders for 5, 7, 8, 10 minutes and still don't understand what they do. Definitely can't understand. So first thing is, is like, can you describe it simply and easily? And do people get it? The second thing is, is when you start talking about it, are people starting to make that leap of, I see how I could use this? Oh, just by him telling me what we do, I could apply to this problem and this thing over here and that thing over here. That's the second step, is you can't— if you have to shove into their face all of the different, um, value propositions and think and challenges you solve, then it's not intuitive enough. And there's no— the, the market knows what it needs to fix itself. If you— when you describe it, they can't start figuring out how to fix those things with what you do, then you don't have product-market fit. And then the last is people pay. Like, you know, you gotta have, you know, you know, a million bucks I think is like the generally accepted whatever. I think that that's pretty arbitrary, like a million things all these investors do while they pick a million bucks is because it's round, not because it's actually accurate number or backed by data in any way whatsoever. But yeah, I think once people like start reliably and predictably paying for stuff and you're winning, you know, 20 to 25% of the opportunities then you probably have product market fit.

No, I love that. And the reason I asked that is because I remember, like, I remember when I was an SDR at Mailjet and I had to explain, I'm like, to my sales ops lady, I'm like, hey, I need outreach. And she's like, what is that? And I was like, it's a sales engagement platform. And she's like, what is that? And like, sales engagement or outreach came out, was like, that category was like nonexistent, right? Arguably it was still being developed. So that's why I say like, like, how did the market know that they needed a product like that and stuff? So it's interesting to hear your journey of that, um, and where that point of inflection was. Um, cool. Let's move on to the next, uh, portion here.

Um, again, I'm gonna do the Q&A. There's a— there's quite a few questions in the Q&A.

I don't know when you want to do that, but yeah, I'll get to that closer to the end. I have a slot that I'll do. Um, So one of the things I wanted to talk about is go-to-market. Obviously you're doing it right now with Operator, you've done it at Outreach. Maybe for some of the early stage founders here, like again, how are you defining your go-to-market? How do you even think about it? What are some of the channels that you're actively exploring? You know, like how does Mark think about go-to-market when he wakes up in the morning? Because you're pretty much going through this emotional as an early stage founder, right? Like, what— how are you?

Yeah, but, but it's not, it's not normal, man. Like, I, I wouldn't be able to tell you what I do and you do it because I got to spend 10 years in SaaS, in GTM tech, meeting with some of the best leaders in the planet, building out a huge network, going to tons of conferences, doing podcasts, having tons of— hosting tons of podcasts. I I, I'm really, really lucky that I have hundreds and hundreds of acquaintances, friends, and people in my network. So, you know, just to give you an example, like when I, um, when I launched the fact that we'd raised money and we're going to start a company called Operator, um, I sent out a few emails and a few texts, and I had over 100 people post for me on that day that I was launching a company, that they were excited about what we were doing and why we were doing it and all that kind of stuff. And that generated a waitlist of over 2,000 people to get started with. So the way that I think about GTM right now for me is I feel like, um, my— I get about 7 million views a year on my content on LinkedIn, and all I'm trying to do is to create content that gets people, that helps people and makes them want more help. And then when they request, or I ask if they need more help, and they have— they need help in an area that operator serves, then that makes a very natural progression for me to move them into my pipeline as an opportunity or whatever. So what I'm trying to create with GTM right now is a much more of a, um, put value out there and attract people into me. And that's actually some of the underpinnings of the product we've built at Operator too, is like, I want people to be attracted into a conversation with me where they open up and we can talk about what's going on, and then I can truthfully tell them whether I can help them out or not. And that's really what I think about GTM right now. But I could tell you how I think about it if that wasn't in my situation too.

Yeah, for sure. Maybe the reason I say that is because obviously I follow the outbound space quite a bit and we have all this thing called outbound and how people are doing the stuff you're doing with content and pushing it, being, let's say, founder-led or personal brand-led or whichever. So I think it sounds like you're going that approach, but back in the day at Outreach, how were you thinking of GTM at that point?

Yeah, so again, GTM 10 years ago is very different. Nobody had Outreach. Very few people were doing mail merges. I thought, you know, Manny was the CEO and co-founder. He was my SDR. He would send me 1,000 leads a week. I'd throw them into Outreach with automated emails and I'd wake up with 100 meetings every single week. Like it was, insane. It was too many meetings for me to even run. So that doesn't work anymore with the current noise. If I was a founder today, uh, what I would do is I would use what, uh, is the technique that got my AEs, my sales reps, the best self-sourced pipeline. And so, you know, you can get pipeline from marketing. AE has really no control of that. You can get a pipeline over SDRs, from SDRs that you have some control but not much. Really, if you want to be a great rep, you have to control some of your own pipeline, and that includes you having to do some of the work and figure things out. I tried this several times at Outreach and failed 2 times. The 3rd time we got it right. And what we did in the 3rd time was rather than say, all right, an SDR has 400 accounts and they work 5 days a week and this is what we expect from them. We're going to give an AE 100 accounts and they— we want them to prospect about 20% of their time. So we're going to expect 20% of the output and 20% of the activity and 20% of the metrics. And that doesn't— that did not work. What worked is, hey, let's look at your quota for the quarter. $250,000. All right, great. That's a nice quota number. $250K, $1 million for a year. All right, what is your average deal size? $30K. All right, great. $30K. How good would you feel knowing that you have $100K of high-quality deals and 3 deals sitting in your pipeline every single quarter, and then marketing and SDRs were filling in the rest? Well, everybody feels really great about that. So, okay, so what we did is we started to say, listen, here's 10 accounts. That's all you get this quarter, 10. And we're going to research why. We're going to figure out what makes us excited about them being a customer other than they're just a big deal or a nice logo. Like, what is the reason why we're reaching out? What is our approach? What do we— what's going on? And we do a bunch of work around that, and then we would create a really strong account plan to break into that account. And when we did that, uh, every rep on my team just about would break into 2, 3, 4, sometimes 5 or 6 accounts. And if I was a founder, what I would do is I'd be like, who are the 10 accounts this month or this week or whatever, you know, depends on how much revenue you need to generate, but like Who are they? And then I'm going to create a really specific plan, and I'm going to convert at least 20 to 40% of those accounts. Rather, rather than what most people are doing right now, which is this kind of spray and pray, spraying clay. I'm gonna— I'm— most founders are technical, they can figure out how to do technical automation, but it's toxic automation, and it's not automation that a single one of those founders would want to be on the receiving end of. Yet they queue it up and start throwing out thousands of emails a week and doing things to others that they wouldn't want done to themselves. We know what happens. Like, we've had, you know, 2,000 years of different religions teaching us what happens when we sow bad seeds. We reap a bad harvest, right? When karma is a real bitch in sales too. If you're gonna spam 2,000 people a week, you and your co-founder, you're not gonna— it's not gonna work. Because karma's a bitch and it's gonna get you.

I love that advice so much. Like I grew up in the different, I used to talk about this a lot about the history of sales going from door-to-door to like the outbound motion to the inbound motion and then, you know, a mass outreach. And now we're very to this like one-to-one level where like, hey, I need to do all the research before I do that outreach to you. So I think that's sound advice for any early stage founder is that you have to take this account-based approach and really learn more about the accounts and then penetrate it. So I think that's amazing. So I guess on that note, and maybe this will be the last question and then we can go to audience Q&A, is where does the future of outbound or the future of sales or the future of all this stuff that we're talking about with AI in mind, where do we end up?

Right?

Because this stuff is changing. I remember when I was an SDR 5 years ago, it was all calls. And then midway it went to emails and now it's like multi-channel and now it's like A/B, like what? Like it's like all this stuff is getting spewed out. Obviously it changes if you're mid-market enterprise, I get that. And like if you're B2B SaaS, fintech, regulated, but I guess overall, like where do you, because you've had the privilege of seeing it from different perspectives, like where do you see it going? And then like, yeah, I think like plugging in Operate and like what you guys are solving might be helpful.

Yes, see 3 paths. Uh, path 1 is people that are completely resistant to AI in the future and they continue to try to do the stuff that they do now with people. And, you know, listen, I think that if you have a good process and stuff, that's doable. I think that there's the other end of that spectrum where you're like, I'm going to get rid of people, I'm going to automate everything, and you're going to use AI instead of people, or instead of you're going to replace a certain percentage of people with AI. I think that that is super dangerous. And I think what I'm seeing from that is these AI SDR companies are raising money, and they're raising money though on smoke and mirrors, and they don't have referenceable customers. They're pretty good in the beginning when they're going after low-hanging fruit. Once it gets hard, they completely fall apart and don't deliver anything. And the more that you remove the human The more transactional the sales become, the more transactional the sales become, the smaller it's going to be, the more competitive pressure you're going to have, the harder it is going to be to differentiate. And so you have to really be careful of moving over into that like toxic levels of automation world. But there are a lot of companies— I mean, I see people on LinkedIn all the time bragging about how they send a million emails a week. Listen, I don't want to get a million emails a week. I'm glad that you can figure out how to send the million emails a week without getting shut down because you're skirting around the rules that we all want in place to protect us from spam, but you figured out a little shortcut around it. Listen, you're really smart. That's cool. Doesn't mean it's the right thing to do, right? And then I think that there's the middle where there is some stuff that AI is extremely good at. and we need to help AI do that, to empower the human to do the things that the human does really well. And that's a bit cliché, quite honestly. Like, I wouldn't say that's a mind-breaking thing, but I think that we are getting to a point in GTM where if you reach out to a company hoping that they have a problem, you are a problem. You are a— that's called spam. If you reach out hoping You are spamming, you're fishing for a problem, right? And people don't want to hear about what you're doing. If you instead— there's so much data, it's so— it— not all of it is accessible, but you can get it. We at Operator, we have it. We bought a ton, a ton of data. You can have AI run and you can only reach out to companies that actually you can prove have indications of a problem and are suffering from that problem. And that's You know, not the pitch, but that's the value prop of operators. Like, we, we give— take— can take a list of companies and we can find the companies that data shows that they have a problem that you solve and that they're suffering from it. And then we create really compelling, unique messaging for an audience of one. The email can go to anybody and it makes sense, but it's only relevant to the one person that we send it to, or the phone call or LinkedIn DM, whatever we're creating. And that's where I see things going, is like Let's stop. We used to say activity was important because you have to churn through so many nos and I don't knows and not I don't have a not right nows to get through it. And that's because we didn't— we— it was impossible or very difficult to figure out does a company have a problem before you call in and before you just target it with your outbound. But I think that we can reverse that now and, and 100% know for sure that the company has the problem before you reach out. And then that takes care of the messaging, right? If you know the problem is, makes messaging easier.

You can reverse engineer it. Dude, that was awesome. I appreciate it so much. Uh, we're going to jump into audience Q&A, and then we'll do that for about 10-15 minutes, and then we'll start to wrap up. So folks, if you head over to the Q&A button, uh, I'll start to screen those. But we have this great question from Steve who put in the other chat. But Mark, he's asking What are the traits you look for when you're hiring for an impactful candidate?

Yeah, great, great question. I have 3 basic buckets. One is effort. I want to know that if you have to make 100 calls a day and it's 5 PM and you're on call 95, do you stay the extra 10 minutes to make the extra 5 dials or do you not? That is where the— that's where real, real outcomes lie is in the doing and the effort. The second thing I look for is curiosity. There's two types of curiosity: internal and external. Internal is, why is my product the best? Why do we do this process the right way? Why do I respond to this objection that way? And then external— external is like, why does that company have the problem? What have they done to fix it in the past? And so you take— and then the last trait is making connection. Is, do you have the business acumen to connect what you know about your company because of internal curiosity, what you figured out about the other company because of external curiosity, and can you make a connection that shows them that they have a need and that they should be motivated on that need, are motivated to move forward on that need. Just despite that, just, uh, in, um, in addition to those, I would think like the biggest thing to me is coachability. Like, I need to know that you're, you're coachable. If you're coachable, you work hard, you're curious, and you have enough business acumen to make connections, I can make you into an unbelievably good seller. So that's the candidate, that's the stuff I look for. But there's other stuff depending— like at Outreach, we needed passion. Like we needed people to have like this John the Baptist, I'm talking about something that's never existed in the world and I need to baptize you because you believe in it so much. So we had to work on like passion. The other thing we had was, or the ability to transfer passion, right? I can not only be excited, but I can get you excited about it. So that was an example, um, of one of like something that was specific to a company, but I can't tell you how important it is to narrow down and figure out exactly what are the 5 traits that you need in a seller, and then look for those, and then take the time to actually figure out how to look for those. So like, for me, hard work is a trait. I can tell if somebody works hard within 5 minutes because I have sat down and thoughtfully figured out what questions do I need to ask to do that. The other one is coachability. I can figure out somebody's coachable with 100% certainty in less than 10 minutes. And, uh, but that's because I thoughtfully sat down and figured it out how to do it. And so, uh, and then what you don't want to get confused with if you're an early-stage founder is skills. Traits and skills are very different. Traits are the innate personality traits of who you are. Are you naturally curious or not? If you are not, nobody can train you to be curious. You either are curious or you're not. Now, you can change yourself become curious. But nobody can change your traits, only you can. The others are skills. Skills are like, can I negotiate? I can teach anybody to negotiate. Can I do a cold call? I can teach anybody to do a cold call. That's just a skill. But if they don't have that trait of coachability and effort, they never can learn the skill. So see, that's why the traits are important. You hire for traits, you train for skills. And if you get your traits right, you will hire really, really good people.

No, I love it. We, we preach that quite a bit at FI as well with, uh, we have some of the protocol entrepreneur DNA tests and, uh, it's all about the traits and then go upwards from there. I'm going to show this question from Thad. Uh, he's, he was asked, he or she was asking, um, uh, what were the signals that convinced you to go 100% commission for 6 months? At what product stage was Outreach at, at that time to help you make a decision to make it easy for them to give you the green light? Um, so I think you briefly talked about this, but if you want to, uh, go—

yeah, so, um, uh, listen, what, what was my motivation for doing 100% commission is, number one, I have— I will always bet on myself. I know how to sell. I know how to be good. I'm not a cheesy used car salesperson. My mantra is I help people make confident decisions. If they go for me, great, I'll take the commission check and I've helped the person. If they don't go for me, one of two things happens. Either they make the right choice with a competitor or another solution and it helps out their business, in which case I'm happy for them, or they make a wrong decision and they come back to me because I help them feel confident in the beginning. And so like, that's the first thing is, is, um, you, uh, I bet on myself because I understand what great selling is. And so there was no nothing other than this was a technology that I understood, uh, you know, that they have this thing called founder market fit. Like, I think I have perfect founder market fit for what Operator does right now. I've spent the last 25 years dealing with the problem that I'm solving. Um, I wasn't the founder at Outreach, but I definitely had extremely good fit, uh, for what I was doing. And so, um, that's kind of what I was looking for. And then the product was— had just become sellable. Like, I met Manny in August I want to say, and he demoed to me kind of out of mocks. He didn't even have like a real product yet when I joined, or maybe that was in May. In August when I joined and started selling, we had just started doing it, and all you could do was automated emails with a sequence. That was it. It was super, super basic. So, uh, but I could— I knew where it was going, and because I was so entrenched in the problem, like, I saw what was going to happen and You know, lucky for me, I jumped on the train. But I would say that what convinced me to go 100% commission was me, my own confidence in my own skills, and my understanding of exactly the solution I was selling and the problem and seeing such a good fit there. But the product was just brand new. We didn't even have a paying customer when I started.

Wow, thank you so much for that backdrop. Um, all right, let's, uh, go to the next question. This question's from Steve. You spent some time talking about PMF, but he was asking, hey, if you're dealing with multiple issues, uh, how do you know which ones you should be prioritizing?

Um, multiple issues for product market fit— I don't, I don't know if there are multiple issues. There's just either have product market fit or don't. I think maybe what you're referencing, Steve, is that there's multiple variables that you are seeing poor product market fit on. Like, you know, maybe you're just not booking enough meetings, maybe people aren't willing to pay, you know, maybe the product doesn't work correctly or something like that. Um, listen, I can tell you what I've done at Operator. Um, I'm— again, I have a platform and people have an inherent, inherent trust in me because of that platform and because I've helped so many companies out in the past, and they can you know, probably reach out to a friend that knows me or knows somebody that knows me and, and can get a really strong reference. But really, man, the number one thing you need to do is just talk to customers, man. I talked to like 70-some-odd people before I even like wrote down my first idea for Operator. Like, by the time I was ready to write it down, I didn't even need to write it down. I just knew what it was. And, uh, and then we've very much iterated a lot since then because If you ask people what they want, according to Henry Ford, they'll ask for a faster horse. They don't, they don't know that they want a car. So if you get to faster horse, your job is to think of what is car, and then you certainly need to start putting that in front of people that think that they want a faster horse and see what they think and what are their comments. And, and are you a good teacher? Can you teach people why you're doing it? Like, you know, big part of what I do is like, this is what people do now and why it doesn't work. This is what we're doing and why that approach makes sense in an environment where what is happening right now doesn't work. So yeah, I would say that if you have multiple poor variables with product market fit that might make you nervous, is your product right or not? I would tell you schedule 4 to 5 conversations a day for 2 to 3 weeks in a row and work your ass off. People will meet with young founders and even older founders. I'm an old guy, I'm almost 50, but people will meet with founders that and give that kind of early product feedback. People really like that. It's an ego boost. It makes them feel like a subject matter expert and that they're part of something. And so that's what I would tell you is, um, if you have multiple variables, you need to start to have a lot more conversations with customers.

Yeah, I like your advice of just narrowing it down, go speak more to prospects and customers and just bring it further, uh, closer.

And it's a little bit— it's a little bit more known now, but, you know, we have— as humans, we have biases. I think the last time I looked, there was like 48 different biases that a human operates inside of. Some of those keep us safe, but most of them lead to bad incestual type of thinking that doesn't allow us to break out. And honestly, like, the, the probably the biggest bias of them all that sucks the worst is confirmation bias. And that is where most founders live, is they're just trying to confirm what they already believe. They're not actually trying to figure out, does what they believe, is it true or not? And so you, in those customer conversations, you cannot exhibit confirmation bias. You can't push people to a situation. You have to see where they lead the conversation. If you have enough conversations that lead in the right direction, then you know that you're starting to build something that has product market fit. Here's the other thing that we did, Ian, that I thought was really good at operators. We basically fake everything in the beginning. We will build the least amount of stuff that we can that has the most manual effort. I mean, it used to take me like 3 or 4 hours to get ready for a sales meeting. And once we did all that, then we were able to review what our results were. After 30 of those meetings, they were all the same. And I knew exactly what people liked and didn't like. So we, we went into the hole for a month and we built the stuff that we actually needed to build to do that, to go figure out what was the next thing that we needed to fake and get real feedback on, you know. And now when I sell the product, it won't be fake anymore, but it is okay for it to be fake in the beginning and for you to show this is the results, get email, get all of the feedback on the results and the outcomes that that would provide. Then now you know what to go build. Rather than building something, hoping it works, and then having to deconstruct it or change parts of it. We only build when we get a critical mass of customer feedback on our extremely manual, quote-unquote, fakey stuff to make sure that people like it. I don't mean like a Figma. I mean, we actually gave people outputs of our system. It's just we had to do a whole bunch of work to get them because we hadn't built in the the tool yet to be able to do it at scale or do it quickly.

For sure. You're doing that one-to-one kind of demo environment. I really like that. That dovetails into the next question. How are we for time? We have 2 minutes. Sureta is asking, when you were starting out at Outreach or even now when you're doing at Operator, you kind of answered this a little bit, but you don't have a paying customer, you're on the sales process, the product is coming fresh off the press. Maybe walk us through, like, were you demoing with clickable prototypes? You just mentioned you're giving your customers output. Like, what, how are you, um, thinking about all this and how are you kind of executing it?

Yeah, what I did at Operator is the first thing I did is I created a design partner group. I was lucky enough to be able to get about 35 people that agreed to be design partners, and that's who I started talking and having regular conversations with. And we would send out Figmas or whatever right, to get feedback. Um, I built out a process though that the testing process is also the initial— excuse me, the initial sales pipeline. So as we would test something, not only would I move them to the next phase of testing, but I would also move them deeper into the sales cycle. And so now, you know, um, I haven't done one single bit of outbound. I'd even started going after my waitlist people yet, and I have, you know, about $1 million in revenue in my pipeline, all from testers and extremely early adopters that made it through a bunch of systems and checkpoints to kind of get to us along the way. Rather than— because I, you know, you just can't deal with everybody that clicks demo, I want a demo, or wants time on your website in the beginning. Like, that's just a lot of focus that's out there, especially when I'm, I'm already having, like, you know, between 4 and 8 meetings a day. So that's what I would say is like, you gotta, uh, you have to create some design partners that you're constantly sending stuff out, talking to them, showing them what things up, show them our mock-ups. But the key is, if you do that, um, again, that confirmation bias will kill you if you don't— if you try to sell them in the design meetings versus just get feedback and see where their head goes. You'll never really understand what you're doing. That's the That's like the biggest problem I see people make is they— you need to have a perspective, and I'm not saying that you need to have an opinion, but in this design phase, what you're looking to do is see, do people come to that opinion without your help, or does it take a shit ton of selling and pitching and all that kind of stuff for people to understand what you're trying to do or not? But do the design partners and then call some friends and get some friends into deal cycles. Give them some output of what your system is, let them see the value, and then And if they're giving you good feedback, then it's time to start selling to people.

I really like that advice. One thing maybe we can dovetail into, because as you were talking, I was thinking about it, is doing a bit discovery, doing like, I figured out the discovery portion of like from sales, but when I started touching product, I'm like, hey, product discovery is very similar to the sales discovery. Maybe the point in the journey is a bit earlier. What is your general take on doing discovery? Do you have a certain framework of thinking about it? Again, I know product sales is a bit different, but a lot of the stuff you just talked about, getting a design group and getting all of this stuff is essentially doing a really good discovery. And I feel like that's one skill some sales reps just still have not perfected because they're taught, just ask, give me a band, give me the, it's so prescriptive that they lose the human element of it. right? So would love to get your, your two cents on that.

Yeah, listen, there's two types of discovery. There's informed discovery and organic discovery. Informed discovery is where you come into the call with a perspective, an observation, a hypothesis of what their problem is and how you can help, and then the conversation centers around that. Then there's organic discovery where you might say something like, what are your top three initiatives for the year? That can be effective too, but it usually is a little bit harder to get there than informed discovery. So that's the first thing that I like to do is to have somebody come in with informed discovery. So I have kind of like a 4-step process that I use for discovery. The first thing is, you know, you need to make sure that you ask an open-ended, provocative question. And that means usually something that's data, something that's pre-prepared, something that you haven't— that's not like a simple, what are your top 3 business initiative type of things? So you ask that question. And then the second step is you do what I call dig the pain hole. And what digging the pain hole is, is that is you taking whatever they say and digging until you get to the understanding of it. The way that most people do discovery is kind of like finding a gold coin on a beach. They pick up the gold coin, they're so happy they got it, they run off to the casino and blow it. You know what really smart people do when they find a gold coin on the thing? They run to the store and get some shovels because they know there's a treasure chest filled with gold coins around there somewhere, and they start digging. And that's how really great sellers work. They, when they get an answer or hear something that they like, they don't just run to the contract and try to close the deal. They try to understand and they dig deeper. So you dig that pain hole. And the way that you do that is you say things like, well, listen, Ian, outbound— or you could say something like, you know, lead conversion means a lot of things to a lot of different people. Like, how do you describe it? Like, what metrics do you look at that define lead conversion for you? And you'll find out like almost every single company has a nuanced definition of that. And figuring out how to speak to their nuance is really powerful. After that, you do something I call diagnose and confirm. So after you, you ask questions, and the point of asking questions is to reach a diagnosis. You don't keep digging past the treasure chest. You dig to the treasure chest, then you open it up. And the treasure chest is the diagnosis. That is, Hey, you know, I talk to a lot of revenue leaders and you know what, like, uh, what I'm hearing from you sounds like your lead conversion's off because you don't have something on your website that can convert people into meetings and you don't have a scheduler on your website. Like, do I have that right? And diagnosis, you share your diagnosis and then you ask, do I have that right? And that's to confirm if you get it right. The call keeps going and you look smart. If you get it wrong, guess what? They correct you and then you get the information and you keep going. So it's a no-lose. And then the last thing is a brief vision of the future. And what that is, is at the end of your diagnosis and confirm, once you have it right, you understand, that's when you say something like, you know what, uh, you don't mention your product, you don't mention your features, you just talk about a future state that could exist. Well, you know what, what if you could get your lead conversion up 3x and all you had to do was to add one little thing to your website? Like, does that sound like, uh, something that would be interesting to you? If they— when they say yes, then that's when you're like, all right, well, you know what, we have that thing. Let me— I'm going to make a note and I'm going to demo that in our demo next call. And that— and you do that, repeat this process 2 or 3 times, and you'll start to understand what are their problems. You'll understand them deeply. You'll have them confirmed by them. Of exactly what's going on using the business acumen that you have and connecting the dots from your questions and answers. And then lastly is they'll start to build excitement to see your demo because you're suggesting specific things that can solve their problems and building that list for that really contextualized demo.

Man, I love this so much. This is like, I wish I had you as a coach and when I did my SDR days. This is really awesome. But even as a founder, It's— these are some really important concepts that people need to digest and stuff. Uh, just— I didn't— I mentioned earlier, we're not— I thought it would get 100 people live. We are about 163 people live right now. I think it went up to 180. So I'm sure there's a lot of people getting a lot of value from this stuff here. Um, we do want to wrap up to make sure we have enough time for networking. Um, what I do want to end is— and I give this to all the speakers— is like, you know, we haven't just the audience is early-stage founders, some individuals are thinking of making that leap, some are already in that pre-seed, seed level, you know, you're kind of going through this motion, kind of what's that number one piece of advice you'd like to give them, something that you've picked up along the way, something that you've picked up as a new founder or kind of like a founder 2.0 kind of hitting this all over again, but like you have so much wisdom to share, so I feel like what is that one final word you wanna give the founders? Founders before we wrap up today?

Yeah, I think there's like 3 major things that a founder does is they, they have conversations, they do work, and they think about work. And I think what, where, what I've learned is, is if you don't create for yourself— and I actually did a post on this today because I was messing it up for a while, uh, because, you know, you constantly, you get into a good rhythm, then you fall out of it slowly, and then if you're not self-aware, you'll find yourself dealing with the problems that you've solved in the past. And so I was able to quickly self-correct, thank goodness. But like, you need to make sure that you have a quota for how many conversations you're having a day. Those can be with future customers, internal team conversations, people in the field that are subject matter experts to the problem you're solving, you know, maybe it's mentors, uh, I don't know. But like, you need to be talking to people. If you don't talk to people you will get into an echo chamber that will never go anywhere. The second thing is there's work to do. Listen, I am an inbox zero guy. I will always like just go try to clean out my inbox, and— or I'll go try to do tasks. Or like, I like to— like, you know, this weekend, on yesterday, like, I painted my bathroom ceiling because there was some grout that some tiler had put in that would gotten on the ceiling. I cleaned out my garage. I washed both cars. I I rearranged something for a Christmas present that was a toolbox I got. I, uh, I did the laundry. I, I made my bed. I, you know, I did like 8 or 9 things. I made— I like to do, do, do, do, do, do. But if you're a doer, sometimes you get stuck in— you're not thinking about what you're doing and you're just going along doing, and then you realize a week later you haven't done anything important. And the last piece is that thought, like the thinking work, your thought work. Do you have several blocks a week or a handful of blocks, a couple blocks a week where you meditate and kind of get in your alpha zone and then turn everything off and be like, I need to think today about how I'm going to get my waitlist bigger. And you just sit down with a piece of paper and a pencil or an iPad and an Apple Pencil or whatever. And you write, you don't type. There's something special that happens when you write and you write out and you think through the things that you need to think through that are really getting in your way. If you, um, if you set aside time to do those 3 specific things, uh, you'll, you'll— I think you'll drastically accelerate, uh, your progress because you'll be thinking about the important things, which will dictate your work, and that will dictate the kind of conversations that you need to have.

Man, so much nuggets here. I feel like, I feel like just learning on you, like, let's go launch something right now, Mark. Let's go. I'm inspired. I'm, I'm ramped up. I think this is Awesome, um, guys, we're coming close to the end. Thank you so much, Mark. This has been—

you want me to like machine gun some of these questions, man? Like, I hate not asking questions when people actually take the time. Can I start at the bottom and just move my way up?

Uh, sure. Are you in the Q&A section or in the chat?

Yeah, I'm in the Q&A.

Yeah, so let's—

yeah, yeah, actually, we'll do Deepak. I launched my health tech startup, but the business model underperformed. With a new client. There you go. Uh, new client onboard and pre-market product. How can I effectively raise awareness and generate interest? Listen, the best way to, um, is to start posting yourself and you build out an audience. And it takes time. Is it— you're like, there's zero way to do this where I could snap my fingers and you're going to do it in an ethical way that isn't some kind of mass and blast prayer spray thing that probably is going to mostly get ignored anyway. The main thing is, is if you care about this problem a ton, you need to start putting out your perspective. Don't overthink it, just write and, you know, puke it out. Just get it out and write every single day. And then what you need to do is you need to set aside about an hour every single day, and what you do is you DM every single person that likes or comments until you get up to a certain amount and it becomes unwieldy. You reach out to 20 people a day and you start to bring them in. You have to build that network, but you build it around the thought leadership that you're doing in your area. That would be the biggest way that I could say to build awareness, and it will not be easy and it will not be fast, but it will be very effective. And things that, you know, take a long time and are hard are worth it.

Um, perfect.

How do you determine the garbage leads when you're assisting a new company with lead conversion? Um, Uh, I'm a big every lead is a good lead until you talk to them. I'm gonna just figure out how to disqualify people in conversations quickly, and then as I start to see similar patterns over and over again, then I'll create automation that moves those people to a different system if they come in. So for example, like right now, uh, Operator is good for high-value accounts. If you do like sub-$5,000 deals, Operator is not a good fit for you. And there's really not any reason for me to talk to you. So we actually have kind of a, a waitlist and a queue for those type of people where we keep them a little warm on the idea of what we're doing, but we are really honest and transparent and say that we're not helping you right now, but as soon as we are, we'll let you know. And so, um, that's how I would do it, is first of all, assume every lead is good, find the patterns of people that don't move forward, then automate them out, uh, in your booking process so that you don't end talking to them. Um, how do you build a genuine waitlist pre-launch when you don't have demos in target? That's the exact thing I talked about earlier with awareness. You, you, you have to like, um, listen, I've been posting almost every day on LinkedIn for 4 years. It took me a long time to kind of get up to a decent number of followers and a decent number of views. And then, you know, now if I don't have a post that gets 100 interactions, it's a bad post for me. When for most people that would be the best post they've ever done. But I, I took my time, I invested in that channel, and, uh, I think that besides my job at Outreach, it's been the most influential thing on my career. And, uh, so, you know, I can almost get to anybody right now. There's very few people that if I want a meeting with that I can't find somebody that I know who's my friend who can personally introduce me and make sure that that meeting happens. It's So, uh, but you gotta, you gotta start. And, uh, if you, if you get started, it doesn't take as long as you think, and it's not as hard as you think. It just requires discipline and consistency.

Perfect. Um, yeah, I think maybe we'll do one more and then we can wrap up, just because I want to be respectful of your time. Is this one by Zakaria, uh, who's talking about it, making the transition into sales and sales development, you know, What are some of the resources you would recommend for people to level up or upskill in sales?

Well, I don't know if I'm turning from an entrepreneur to an intrapreneur.

I'm not exactly sure what that means, but basically he's going into an internal organization similar to your transition going from like going into outreach. There's a founder and they'll be doing more entrepreneurial initiatives.

So they're, they're kind of working with an entrepreneur then, huh?

Yeah, we're working with the founder, but they have to take the initiative to launch like a new product or a new project or a new department or whichever.

Yeah, listen, I, uh, um, what I would recommend is, is, uh, there's a weird balance when you're not the founder of ownership. And what I mean by that is, is without extreme levels of ownership, you don't push through all of the stuff that's in your way to make sure that something can live. And unlike having a baby, you know, you got to push through stuff in order for this thing to live. It's not going to just kind of like mature in your belly for 9 months and then kind of naturally slide out, you know what I mean? And I'm oversimplifying that, maybe a bit crude, apologies, but like you have to work to make it live. In order to make it work, you have to feel some ownership. And so that's where it— you just have to figure out, like, with your founders, like, how much ownership can you have? I felt tons of ownership at Outreach, and that's because the product was using my ideas. I understood it. I understood the problem better than the founders did. You know, I was doing the work every single day. Like, I saw this as my chance, and I, I I worked as hard as I could on it. Um, so that's what I would say is like, you have to find a healthy level of ownership for what you're going to do for a founder or an entrepreneur, and in their service and in the service of their vision and their product. And if you can find that level of ownership, you'll have the motivation you need. And then the second thing— I tell my kids this all the time— is that you gotta have fun and work hard. Hard. Uh, if you're not having fun, you don't have the fuel to work hard. If you don't work hard, then things won't be successful and you won't feel like you're contributing, and then that's when you start to like check out. So, uh, to me it all starts with fun. So find the right level of ownership that's appropriate for you, that makes you feel attached to the success, and secondly, figure out how you can have fun doing that, because fun is the fuel of hard work.

Awesome. Thanks so much for that. That was super helpful. Appreciate you sticking around for a bit more. What I do want to do is I will wrap up the session here because we do have networking. We can chat to see if you're still available, but folks, you'll have some tables. Feel free to talk to each other and learn from one another, and then we'll leave those tables opened up. We threw up Mark's LinkedIn, we'll put it in the follow-up email. You'll get the recording within 24 hours. It'll be up on YouTube as well. Go follow Mark, show him some love, like tweet about this. This has been awesome. I feel like this was a masterclass in like so many different things. But, uh, but yeah, Mark, thank you so much for taking the time.

Yeah, no problem. Thanks for having me.

Awesome. All right, thanks everyone.

Bye.