AIMinds #039 | Michael Ocean, Founder & CEO at SellMeThisPen

About this episode

Michael Ocean is a dynamic entrepreneur from Ingersoll, Ontario, known for his innovative community-building platforms. His entrepreneurial journey began over 15 years ago when he observed a friend organizing local meet-up groups for non-native English speakers. Inspired by this, he envisioned a global digital marketplace for language learning, leading to the creation of his first startup, which revolutionized how language communities connect and grow.

Michael is a 3x founder with 10 years of sales experience and previously served as a Leader at Hopin.

Listen to the episode on Spotify, Apple Podcast, Podcast addicts, Castbox. You can also watch this episode on YouTube.

In this episode of AIMinds, we explore the journey of Michael Ocean, a former musician turned entrepreneur and CEO of SellMeThisPen. Michael shares insights into his transition from music to the corporate world, highlighting how early experiences in fast-paced startup environments sparked his entrepreneurial spirit. He recounts his foundational work with a startup focused on fostering English practice among non-native speakers, which evolved into a global digital marketplace that nurtured a sense of community.

Michael’s corporate stint at PCM revealed the limitations of traditional corporate culture, leading him to seek more dynamic environments like Hopin. At Hopin, he contributed to rapid growth while navigating the complexities of scaling and organizational change. His experiences with sales teams during this time exposed inefficiencies in training methodologies within high-growth settings, ultimately inspiring him to create SellMeThisPen.

SellMeThisPen provides real-time sales training and enablement through AI technology, addressing the challenges of traditional training methods. Michael emphasizes the importance of targeted, personalized training that adapts to individual needs within sales teams, critically analyzing the effectiveness of broad sales methodologies and showcasing AI's potential to enhance sales performance.

Fun Fact: One of Michael's first startup ventures involved creating a global marketplace for English practice. It started from physically organized group meetings in a small town and evolved into an online platform that attracted users worldwide to practice English in tiny sessions, leveraging his friend's background in teaching.

Show Notes:

00:00 Startup for global English practice marketplace idea.

06:09 Sales teams prioritize product over buyer personas.

07:03 Poor sales training and inadequate coaching resources.

11:32 Simplified, accessible playbooks are valuable, complex ones aren't.

13:53 Understand gaps, focus on improvement areas.

19:37 Added AI training for comprehensive sales coaching.

20:52 Warm-up strategies enhance sales call effectiveness.

24:11 Tailored coaching aligns with individual selling styles.

27:39 Excited for your success, keep going!

More Quotes from Michael Ocean:

Transcript:

Demetrios Brinkmann:

Welcome back to the AI Minds podcast. This is a podcast where we explore the companies of tomorrow. Built AI first, and I, like always, am your host, Demetrios. And this episode is brought to you by Deepgram, the number one speech to text and text to speech API on the Internet today. Trusted by the world's top conversational AI leaders, startups, and enterprises. Some of them you may have heard of, like Spotify, Twilio, NASA, and Citibank. In this episode, we're joined by my man Michael, the founder and CEO of SellMeThisPen. How you doing, dude? Pretty good.

Michael Ocean:

Appreciate you. Good to be here. I'm doing right.

Demetrios Brinkmann:

Well, let's back up a bit before SellMeThisPen. You started off in your journey as a musician. You quickly jumped into the business world, went corporate first, and recognized you didn't like that atmosphere where you had to scan your badge and you were being watched like a hawk. And so you got familiar with startups, right? What was the first startup that you joined?

Michael Ocean:

Good question. So, first startup? It was with a best friend of mine, I actually staying at his place in a tiny little town called Ingersoll, 2 hours away from Toronto. So he was running this group meetings for people to practice their English. So just imagine if you're in a country that you don't, you know, hang out with a lot of english speakers. If you want to improve your English, you need the community to be able to openly, you know, have conversations, make mistakes, get some feedback, et cetera, et cetera. So he was doing this basically in physical events, if you will. And when I joined in, the idea was like, can we make it a marketplace? Can we get a global presence where people from all over the world can actually come to this in a tiny little sessions and practice? And we were talking 15 something years ago when we started this.

Demetrios Brinkmann:

Wow.

Michael Ocean:

So again, we started as a community, running some sessions. My friend got some background in teaching, and then we started bringing more teachers to the platform. So it was just kind of like a connect with an expert and get some practice with the community, sort of like environment. And we raised some angel money. The guys ended up joining a startup, Chile, at some point, and I. I moved to sales. I started my first sales job at this corporate called PCM, selling Microsoft Solutions, Office 365, dealing with ctos and IT departments. And to your point, I hated the culture.

Demetrios Brinkmann:

So you got out of that. And as a former ESL English, as a second language teacher in Spain, I understand the pain. And I think that product that you all were working on is a fun one. I wished there was something like that to help my students back in the day. If only I would have met you a little earlier, it could have been a little easier. But then you went on to work for some bigger names, right? I know you were working for Hopin for a little bit, and you started your own stuff too, in those years after corporate. Can you tell us about what that journey was?

Michael Ocean:

Yeah, absolutely. So with Hopin, I actually failed a second startup. So we had some, you know, massive success before actually failing. So we hit $1 million in ARR in six months, and we had to go through some, you know, iterations and be pivoted because of some of what was the startup theory. So at the time, I was actually in the Middle east. So being crazy enough, you know, traveling around the world that I was in the Middle east, and we started this startup there. We grew really quickly, but then because of sanctions and some political issues, we had to do a number of pivots, and we ended up actually shutting down the company. So I'm back to Canada and started doing consulting with a bunch of startups, and then Hopin popped up.

Michael Ocean:

So at the time, if you remember during COVID it was a big name, fastest growing startup in history, et cetera, et cetera. I joined right after series A, and I stayed with them until a $400 million series C, where things actually started to get a little bit messy. And kind of like the idea of SellMeThisPen was born inside Hopin because some of the things I had to do, you know, manually helping some junior reps get up to speed, kind of like translated to the platform that we have today. And I decided to quit Hopin and go full time with SellMeThisPen. And it's been almost, what, two and a half years that I've been doing this full time right now.

Demetrios Brinkmann:

So talk to me about the messiness of going from a series a company. And I imagine there was probably 40, 50 people working at the company to a series C getting a lot of cash. And then I can imagine a good chunk of that cash was invested into the sales team. So you're scaling up, you're also getting all different caliber reps, and you have to, like you said, train up some of them. How did it get messy? What do you mean by that word?

Michael Ocean:

That's a great question. Look, hyper growth to startups, obviously things are messy. It's not only about sales team. Everything is crazy. You're moving fast, you're experimenting, and there's not necessarily a problem with that, and especially those days like with Hopin, obviously we are getting this massive, you know, imbalance because of, you know, Covid. So everybody wants to run their events, they don't want to go out of business, but it's, you know, physical event anymore. Right?

Demetrios Brinkmann:

Yeah.

Michael Ocean:

I can talk about challenges that sales team in particular actually faced. And to me it was kind of like similar to anywhere else that I worked at. Even with the corporate, you know, we had, you know, trainers flying from, I don't know, states to Canada to teach us about Microsoft products or we have some materials. Companies typically are really focused on the product they're selling to their clients. So learn about all the bells and whistles that our product offers rather than focusing on buyer Personas because that is really difficult to teach. Let's say a fresh green rep, how to have a great conversation with a CTO, with the CMO. Like the age gap itself, if you think about it, makes things really difficult. So Hoping was not different compared to other startups or companies I worked at.

Michael Ocean:

We didn't have a really good structured sales training relevant to the bar Persona we were selling to. And also in terms of coaching, that basically helped reinforce that training and adjust some of the mistakes and problems, you know, reps actually face during their, you know, interactions with clients was almost, you know, invisible. Why? Because managers didn't have the bandwidth. You faced with this massive, you know, fast growth. So you need to focus on hype reviews instead of coaching during one on ones. And then at some point in, I think it was around close to serious c, we brought someone for sales enablement, but the expectation was wrong. You have a sales organization of 200, 250 people struggling differently because each individual is different, right. And you have one person enablement team try to build a program around, you know, efficacy of their practices.

Michael Ocean:

And obviously, like anywhere else, enablement is typically, you know, tracking adoption to methodology or people attended to my training session, but because these practices are really event based. So you get us during onboarding, you get it when you screw up your quota this, this quarter, you get it when we have new product launch. It's not really continuous and around foundational skill sets and that's where all the problems actually started to, you know, pop up when inbound leads get a little bit less heavy compared to three month, you know, when things started to open up, people realize, okay, we need the outbound muscle to work, but we don't have the skill sets. And it's really hard to quickly, you know, bridge that gap, especially when you're in that hyper growth mode.

Demetrios Brinkmann:

So the enablement was there to try and help the sales team get better at what they're doing. And they were doing that by running sessions. Is that what I understood?

Michael Ocean:

So just imagine this week when I say everything is really event based. I can give you real life examples. We ran some role play sessions in group setting maybe once a month, which is not enough because the best way you can actually master a skillset, regardless of what it is, it's not only about sales, is to practice. You learn swimming, but most probably it's just like, you know, going back and forth many times, you know, drank some water, be scared, but you keep doing it. And then you have your trainer standing up there said, hey, fix your hand, go a little bit. This, you don't need to rush through it. So that's the coaching it. So what enablement was doing running this training session in a group setting, which is really uncomfortable, and randomly choosing a few reps to role play.

Michael Ocean:

So first and foremost, many of the other reps didn't get a chance to actually practice. And the ones who actually did practice in a group setting felt uncomfortable because I'm like, oh, dude, the VP of sales is sitting there, boy, screw up. You know, it's my career. Maybe I don't get that, you know, next position because of this. And also, enablement was really heavy on material. Let's just get all these great videos from gong. Let's gather some information from LinkedIn and all this scattered data. Although it was just like getting closer.

Michael Ocean:

As, you know, one source of truth, let's call it a playbook. Nobody goes through that playbook. You know, you never get better at a performance based career by reading, okay, I read this book. I might actually boost my self confidence a little bit, but it's not real because can you actually apply what you learn in real life?

Demetrios Brinkmann:

Yeah, you have to put it into practice. And so you were seeing that since folks were getting very sparse information on how they could get better and then not having this dojo to go and train in, there weren't the type of results that you would expect.

Michael Ocean:

That is absolutely correct. And it was for myself as well. So I was aiming for more senior positions, but I'm like, okay, I have some material in front of me, but I'm high performing in my own role. How should I actually learn? What am I doing? Right?

Demetrios Brinkmann:

Yeah.

Michael Ocean:

So it was kind of like even impossible. So it's the same thing almost everywhere. It's not only, you know, for Hopin like, I would say, I've seen this almost every, at every sales organization, at least I worked at.

Demetrios Brinkmann:

And what makes a good sales playbook?

Michael Ocean:

Look, I would say it's bad to say because I don't believe in playbooks, to be honest. I don't believe in massive hundreds of pages of Playbook that be, you know, gather only through some historic data. I would say if it's in smaller pieces and it is something that you can use it today as a seller and you can easily access to the data that you need, then it's worthy, regardless of how thick or, you know, tiny your playbook might be. Companies obsess over adding all sort of data to say, I have a complete playbook for 100 page, but do your reps actually go and read it? So if it's something that you can quickly digest and apply to your day to day, that is valuable, otherwise, it's just, you know, waste of time actually building one.

Demetrios Brinkmann:

So it's almost like if you're trying to cover all these different edge cases, you're shooting yourself in the foot.

Michael Ocean:

I believe so. I believe so. If you cannot offer practice on those specific use cases, then you're just wasting your time, you know, gathering information that is already, you know, available. Yes, it could be company, you know, specific, but information does not help you become a great performer. It's needed for, you know, reps to go through it to get familiar, you know, with your specific use case as a company. But practice is the key to actually mastering anything. That's what I believe.

Demetrios Brinkmann:

So tangible, actionable, bite sized insights are the most valuable. And I can attest that whenever I'm going onto a call and I'm trying to think about the 50 things that I need to do in this call as opposed to just hyper focused on one thing. What is one outcome that I'm trying to get from this call? The call goes infinitely better when you're just focusing on one thing that you're trying to understand.

Michael Ocean:

That is true. As long as you don't complicate the situation, I think you can expect a better result.

Demetrios Brinkmann:

And so are there certain things that you have seen in these bite sized teachings that are worth their weight in gold? For sales reps, I would say the.

Michael Ocean:

First step is to understand the gaps. So, yes, maybe you're a fresh junior rep. You just got started. You never been in sales, but there's a reason why you started in sales. For now, hopefully, it's not out of, you know, expression. Wanted to start in this career because you see the uptake, you can make a lot of money, you can make big impact you can, you know, expand your network, but you're good at certain things. And I would say most salespeople are good at building rapport, and they don't necessarily have a big problem with, you know, having conversations with people. First and foremost for companies, if you can do skill gap assessment to understand, like, what areas of improvement to focus on, you're doing a big favor to yourself and to your reps and your sales organization as a whole.

Michael Ocean:

So if Michael is struggling with digging deep for, you know, pain and finding business problem during discovery calls, this is really specific, so you can focus on actually helping with him with that rather than giving him a one on one. Let's talk about from setting agenda till the end of it. If it's, again, based on individual needs, there is value in it. If it's just a generic one size fit all practice, I would say it's a waste of time because people really have different needs, different skill gaps.

Demetrios Brinkmann:

I love that. I totally see it because my problems are much different than your problems, and especially depending on how advanced I am in the company and the understanding of the features and everything that's going on there and how advanced I am as my sales career goes on. So you were at Hopin you decided, all right, there's gotta be something that I can do to create a better experience for sales reps. How did I SellMeThisPen come about?

Michael Ocean:

I remember we hired a number of sdrs at some point, and some of them was actually coming on my calls. And I remember I joined one of the strs and one is one of his qualification calls, and he started talking about enterprise pricing. I know there's a big debate of like, SDR shouldn't talk about pricing, or they should, or surface level, etcetera, etcetera. I remember I was just sending a message on slack. Please don't say anything. This is large adapt products saying you can have deeper conversation on pricing.

Demetrios Brinkmann:

Stop talking. Stop talking right now.

Michael Ocean:

Exactly.

Demetrios Brinkmann:

Channel cut this guy off.

Michael Ocean:

And after the call was done, we had him one on one and said, why did you say that? How did you know? It's like, because you do a quick research and I can see the use case is bigger than that because of this, this and that. And then honestly, I kind of got a little bit pissed. I was like, your manager should do this, I shouldn't do that, your manager should do this.

Demetrios Brinkmann:

Plus should do what? Give you the feedback.

Michael Ocean:

Give you the feedback, should be on those calls and actually give you the feedback. We have this in startup culture that everybody should help everyone. But at the same time, we are taking people from their day to day work, and I was one of their high performing reps, not to basically go out there and sell and go help with onboarding, which I understand it helps with the culture, with team building, but we pretty much didn't have, at least at that point. I'm sure after series C, hopefully with some feedback, they figured this out. I don't know, because I have no idea. But before that, we didn't have this manager one on one sessions where we could actually go and talk about tactical things, really listen to conversations, or have a conversation around the problems that I face in this specific call and get some actionable feedback so I can do better next time. Right. So, um, I started having this conversation with a technical friend of mine, my former CTO.

Michael Ocean:

It's like, look, I'm doing this. Can we just, just imagine if you could replicate me and instead of me going on the call and managers actually don't go, so just imagine if other reps don't go on a call, could we give some direction to reps, at least by saying, don't say anything or do say that? Can we just do that? So the idea of SellMeThisPen was born as a real time assistant, right? Now, obviously, you know, it got more legs to, you know, practice and coaching, etcetera, etcetera. We started being a real time assistant, just helping reps ask the right questions and handle objections easier. So that was the MVP of this product. And then again, be iterated a few times and the product is a little bit different, but we still have that, you know, real time coaching and, you know, help as well.

Demetrios Brinkmann:

What did you pivot to? What gave you the signals that you needed to change the product?

Michael Ocean:

While I was at Hopin? Yes, the idea, I was born because of that experience, but I started doing a lot of research. I think I had over 400 conversations, spam of five, six months with sales enablement leaders, with, you know, vps of sales, head of sales. And I realized, okay, coaching is important. Being in real time, adjusting some of this behavior makes things really sticky for the rep because it's just happening there. You just imagine you're inside the ring, you're not expecting the punch, you get the punch, and then someone comes and said, that's okay, just stand up and you go from the left, right. But if the foundation is not built, this might actually just distract reps rather than, you know, giving them more coaching or help in real time. So you started looking around and said at the time it was only one company was doing something similar to what we do today, second nature. They were doing this, you know, role play practices.

Michael Ocean:

And I was like, okay, what if we can add a practice module to what we do so reps can actually practice before going on calls and burning leads through realistic, you know, practices with AI buyers. And then when they get to the point or certain, you know, score or certain skill set built, then we set them, let's say, on field and let them have an interaction with the client. So that's where we actually did not change necessarily what we had. We added roleplay as part of the offering. So kind of like we, this is what we, we say right now. We help reps before, during, and after the calls. So it's an end to end sort of like coaching cycle where they start by practice, get some coaching, like one on one setting, and then you go on actual call, you get help when you are with the client, and right after the call, you get that feedback so you're not reliant of another rep or a manager or someone from enablement. You always have access to, you know, feedback 24/7 based on real conversations.

Michael Ocean:

So we kind of like connect practice and execution together right now.

Demetrios Brinkmann:

Man, I cannot tell you how valuable it would have been for me in my sales days to have that warm up before the call of. All right, cool. Let me try to say these things or get this information that I'm looking for again, going in singular focus. All right, this is what the outcome that I'm looking for in this is, here's how I'm going to go about it. And I have a sparring partner, and I get the opportunity to ask the question in various different ways, or I get the opportunity to see, maybe there's an objection over here, maybe there's a way that they're putting it, or maybe they just don't want to tell me. So I have to try and ask again and a different way. Let me see if I can rephrase this. All of that just would get me so warmed up so that when I go on to the call and I could see myself, I 100% would have done this.

Demetrios Brinkmann:

You know, like the hour before the call, I would have just been trying to run back the call that I'm about to go on, and where I would get tripped up is go back to that and try and run it three or four or five times back. And then when I get on the call, I would feel like, oh, well, this is second nature already.

Michael Ocean:

Yep, yep. That's exactly the idea that you practice to build that muscle memory. And you ask me about my former life being a musician, sometimes people think, okay, there's magic. Like you read all these notes and you listen to, you know, the sounds of, you know, the songs and everything, and then all of a sudden you're a pro. But in reality, that the part that helped you actually become a good performer and to boost your confidence to know things by heart. And you get that through practice. Like, you practice hours and hours and hours. You know the rhythm, you know exactly.

Michael Ocean:

You know where the hook will come. So you don't need to even look at anything when you're on the safe. It's pretty much the same concept here.

Demetrios Brinkmann:

Yeah. You know how it has to sound and you know what an a note sounds like because you've heard it so many times. And so I agree with that. And I also can see the value in, after a rough call, I thought I went in there all, I thought I was fully prepared and I just got rocked. And then I go back and I get a little bit a, I can listen to the call back or I can get some choice words from a coach that never goes to sleep and is never out of office. Right.

Michael Ocean:

This is a very good point. And currently the problem with, you know, solutions that are, you know, widely available to companies is, okay, you screwed up the call first and foremost. You typically reps don't bring that call for, you know, one on one sessions with their managers because it's ugly. You know, you feel weird. But just imagine if you can bring one call first and foremost, maybe you screwed up three other calls. Maybe there's some learnings in each one of them. Maybe you face the same challenge over and over again, but because of the bandwidth problem, you can only, let's say, focus on one call, right? And the judgment, the fear of being judged at least is still there. And also with the tools to your point, if you have call recording tools, which is great, you see the reality, but what's next? Okay, I listened to this and it seems like I didn't do a good job.

Michael Ocean:

How should I change it? So if my manager don't tell me. And by the way, many managers, many frontline managers don't even know how to coach the high performing reps. They just turn to managers. So that coaching skill to give you that safe environment to open up and also have the skill sets to transfer knowledge, the way you can actually apply as a performer on your own ways, on your terms, you are not the manager, right. You have different skill sets different personality. So what we do differently right now with selling the spend, you can have a verbal conversation with your coach and the coach could be basically built based on your seller Persona. So it's not only about what you're selling, but the type of sellers you have, let's say on the platform, on board it, if they're junior reps, if someone is sensitive, if they like answers, to be straight to the point, these are the things you can adjust with. SellMeThisPen.

Michael Ocean:

And your one on one conversation with your sales coach is really personalized based on your abilities and strengths and weaknesses, if you will.

Demetrios Brinkmann:

Yeah, reminds me of, I think I just saw a study that was done by, I want to say it was Harvard on their incoming class who was allowed to use chat GPT for the class and not only allowed to, but almost like encouraged to. And they saw that people not only learned better, but they were higher engaged in the actual course because you get the learnings in the way that you want the learnings right. And so it does feel like 100% align with what you are saying. Now the last thing I will ask is, do you do specific types of teaching sales methods? Is it like, because I know the Sandler method is huge out there, you have different closing strategies. Is all of that brought into it or is it something that I can choose as a rep?

Michael Ocean:

That's a great question. So we have some templates, obviously, and we have our own practices. We call it the SMTP methodology, but you can add any methodology. So if your organization, let's say is a seller house, or if you guys using medic, you can easily build this scorecards and coaching methodologies based on your best practices or methodology, if you will. But again, to me, like sales methodologies, they're pretty much all the same. Like yes, they have different tweaks to things. One of my favorites is just gap, for example, because it resonates with me. But you don't have to limit your reps, especially if you don't have a solid methodology already embedded to your organization and you're just testing the waters with different options.

Michael Ocean:

You can evaluate them based on different methodologies and then help yourself as a leader without actually paying the big buck. Because something like command a message, command of a message for an.org with 400 500 reps will cost you $2 million something. So instead of burning the cash, you can embed them and quickly test with your reps and see which one they adopt better before pulling the trigger and go for, you know, full implementation of any of these nice.

Demetrios Brinkmann:

Well, Michael, man, this has been awesome, and I am so excited for your success. Keep rocking, dude. I really appreciate what you're doing, and, yeah, it is. It's so cool to see, so keep it up.

Michael Ocean:

Thank you very much. Appreciate it.