272: How Technical Founders Can Win in the Software Business - with Eric Weiss

Matt Wolach: 0:10

If you're a technical founder, how do you know how to achieve product market fit? How do you know how to manage your team? How do you know how to do anything within your business, they don't train you that in engineering school.Fortunately, Eric Weiss here,he's a coach to technical founders, he helps them understand how to manage those processes within the business side of their company, and also how to achieve Product Market Fit amongst a bunch of other things. He came in and shared a total mass of wisdom with us,you're gonna really enjoy this one.

Intro/ Outro: 0:41

Welcome to Scale Your SaaS, the podcast that gives you proven techniques and formulas for boosting your revenue and achieving your dream exit, brought to you by a guy who's done just that multiple times. Here's your host, Matt Wolach,

Matt Wolach: 0:57

and welcome to Scale Your SaaS very happy to have you here. Thank you very much for being here. And taking time, our goal is to help you grow your software company. So today, I'm really excited to have Eric Weiss with me. I was on Eric show a few months ago.And now he has an opportunity to come on to our show, because I just love this guy. He's doing some great stuff, Eric, thanks for coming on the show.

Eric Weiss: 1:18

Thank you so much,Matt. I appreciate it. Happy to be here. And I hope I can match your incredible energy.

Matt Wolach: 1:24

I'm sure you can.I'm sure you can, my friend. Let me tell everybody about you,Eric. So Eric is an executive coach at fullcycle. Executive Coaching Eric works with technical founder, CTO, CEOs and VPs of engineering and product to intentionally mature with the needs of their business. He helps really develop strong leadership and and overcome growing pains that people face when they're in that growth stage. He helps executives discover their critical areas for growth, create clear intentions, and an actionable plan and hold them accountable to achieve their goals. He's also the host at chaos to clarity podcast, definitely some great stuff on that podcast, go check out his show chaos to clarity right now. Once again,Eric, thanks for coming.

Eric Weiss: 2:06

Appreciate it. Thank you, man.

Matt Wolach: 2:08

Absolutely. So tell me what's going on with you lately.

Eric Weiss: 2:12

Oh, my gosh, well,you know, the life of an entrepreneur, several different irons in the fire. But as you mentioned, you know, I've been been been loving and enjoying doing the podcast having you on the show recently was a was a real treat. But being able to talk to some incredible SAS executives and thought leaders,we just had the CEO of Envision on the show, the CEO of Gong,and some pretty incredible ones coming up that I don't think I want to spoil just yet. But some big names that momentum is growing. And and again, it's just been a lot of fun. And then also, I have a obviously I'm an executive coach. And I also have a startup accelerator called chaos to clarity as well, a chaos clarity accelerator, and I'm working with some really great early growth stage founders, helping them find product market fit, build really incredible teams and get to scale.

Matt Wolach: 3:04

Super cool stuff you're doing. I just love it. So tell me why did you choose to become an executive coach?

Eric Weiss: 3:10

Well, it's really,it's actually just sort of, in my DNA, it's always been my leadership philosophy or my leadership style. You know, I grew up obviously, as an engineer, I was an engineering leader and a CTO. And I always just found that I got the best out of people, when I didn't make it about me, but really made it about them. And helping them realize their potential and realizing their goals, through the vehicle of our of my team and our company. So it's just something I've always done even as a sort of a side business throughout my career. And about five years ago, I started by my own executive coaching business.And again, been able to work with some incredible companies.You know, open AI, as an example, was a was a client of mine, a couple years ago and had a lot of fun before they went and broke the world. You know,and big companies, small companies, everything in between, but I love helping tech leaders, become better leaders build better products and actually have some fun while they're doing it.

Matt Wolach: 4:14

Super cool. I think that's really what it's all about making sure you have fun.I know that there's a lot of stresses that come with running a business, of course, but you know, when I look back at some of my early stage companies, I just think about all the fun that we had and the good times,isn't that right?

Eric Weiss: 4:28

Yeah, absolutely.There's a there's a there's actually a Buddhist quote that I like to use. That is, life is a journey, and the destination is death. So you might as well enjoy the ride, right?

Matt Wolach: 4:41

So true. I love that. I think I've heard that when she said it. I remember it.But man, that's so true. And I think it is all about that destination. I want to ask you working with technical founders.What do you feel are some of the differences in how they approach tasks versus you know, someone who have more of a business side background?

Eric Weiss: 4:58

Yeah, well, yes. Uh,you know, working with CTOs a lot, they're definitely a bit more. Well, I would say sometimes detail oriented,process driven data driven, and which is, you know, a blessing and a curse. So they can provide some structure and some rigor to maybe the more flighty or impulsive, CEO counterparts. But that also does become a challenge when maybe they lack some of the vision and the story behind what they're doing. So I actually coach a lot of CTOs to be more story, story driven, and customer focused so that they can actually inspire the folks on their team because, you know,against traditional wisdom,engineers are not robots,they're humans. And they actually care about the work that they're doing and the impact that they're having in the world. And many engineering leaders don't do enough to really connect their work to the customer in the meeting.

Matt Wolach: 6:01

I do believe that for the engineers that I've worked with, I think back to some of my CTOs. And I feel like they really do care that the product is helping, and it's so cool to see and, you know, maybe coming in not being an engineer myself, I might have had a different perception, but I've just really enjoyed my working relationship with them and how they approach what they're doing.

Eric Weiss: 6:22

Yeah, yeah,absolutely. I think we all are looking for meaning and inspiration in our work. And unfortunately, engineering is a little bit downstream are sort of down the assembly line. And they tend to get really disconnected from the customer.And really from the from the mission. And so I'm always coaching, you know, CEOs, CTOs,engineering leaders, etc. find compelling stories, with every feature with every task that you release, say, what, what, what does, what impact is this thing making in the world.

Matt Wolach: 6:55

I love that I think that's so important too, because you're right, engineering gets a bit disconnected from the rest of, or at least from the customer base, right. And they don't really have that feel like customer success might like sales does, of course. And so figuring out how they're improving how they're making impact how they're helping people out there, I think is critical. One of the things I did was I would have each member of that team sit with our sales team once a month, or sorry,once a quarter, it was not once a month, but that would have been a bit too long. But they would sit and listen to a sales call. And they would hear some of the things that the market is going through. And they would hear, you know, what people are facing out there and what they're thinking about and what they're trying to accomplish and what they need within a software product. But they would also hear how much they love it when they see the product and sales shows them this and walks them through this. They're like, Wow,that's so cool. And I think it's important for engineering to hear that people absolutely love it. Right?

Eric Weiss: 7:54

Yeah. Oh,absolutely. I mean, of course,we, you know, we're builders,right. And we wanted to see that what we're building, people are excited about right, that we're not just a cog in the machine.So I love that I also with my own teams, would have them do a shift on customer success. So you, you want to get the kind of unvarnished view of how people are seeing your product, if especially when it pertains to quality. So especially engineering teams that are maybe disconnected from QA or don't really feel don't really feel the impact of all those bugs sitting in their queue, have them go do a shift on QA and have to actually make excuses for and, and atone for the quality issues in your product.Not only does it you know, help them be more voting motivated around quality, but it also again, helps them connect with and care more about the customers

Matt Wolach: 8:45

love it, I definitely think that they're gonna see a lot of things that they're gonna want to improve.Because I know sitting on some of those customer success calls myself, it gets a little nerve racking, when the system doesn't do quite what you're hoping it would do.

Eric Weiss: 8:57

I did it myself,several times. And so this company I was working at, we had these these customer success,like personas, like you weren't just talking to one person, your ticket might actually get passed around. So I was Kelly, I was a20 something active, you know,person that was that was very bubbly and cheerful and really loved making customers happy.And we had our whole persona around that. And acting as Kelly I had to work with a very disgruntled Marine, who was very mad about the quality issues in our product and was just cussing at us and just saying the nastiest things, but forcing myself into that persona, and helping them through that through that issue. He actually came back and said, You know what, I'm so sorry. I didn't even think you were real people.I didn't I was just sort of yelling into the void. And you know what, I'm so grateful that you took the time and you helped me with my issue and actually became a fan and left us like a five star review on the on the App Store. So it was, it was a big challenge for me personally to get over some of my normal maybe curmudgeonly ways around,you know, as the quality, it's just it's the user problem,right? Or yeah, customer problem, but it was actually a good opportunity for me to, to make a connection. And again,take pride in our work.

Matt Wolach: 10:21

That's so cool.That's, that's one of the best experiences. If you're helping somebody and supporters, they're really upset and then turn them into a raving fan is like a gold, right?

Eric Weiss: 10:30

Yeah, exactly. And it just takes man, it just takes care. Right? When customer success, especially when it's just a numbers game, probably the same thing in sales, when you're just trying to crank through deals or churn through tickets, and you lose that customer connection. quality suffers, and customers are impacted. And, and you have to ask yourself, What's worth the trade off? cranking through a few extra deals, maybe hiring an extra support person or to or the churn that comes with?Losing a customer?

Matt Wolach: 11:00

For sure. Yeah,exactly. That's good way to think about it. What are some of the challenges that these leaders are facing that you're working with? And and how do you help them overcome these challenges?

Eric Weiss: 11:10

Yeah, well, you know, in my, in my startup accelerator, we focus on a few key areas here, mainly around people process and product,right. So how do you build a really strong team that is aligned with the mission that is talented and motivated? How do we align those teams towards a common goal, and give them the structure and the process to execute and get the job done?And then how do we create incredible customer experiences,build great products and solve really important problems. And obviously, all of this culminates in, you know, product market fit, really great team culture, scalable process. And then ultimately, that turns into runaway growth and scale and easy fundraising and easy sales and great retention, and great reviews and great sentiment and virality, and all the fun stuff that we're looking for. And on the other side of that is stalling burning money, losing people, overhead managing teams that aren't performing sloppy process quality issues, and ultimately, the death spiral.Right. So it all kind of comes down to those, those few key pillars. And that's what we're focusing on every month in the accelerator.

Matt Wolach: 12:24

I love it. And are you able to tailor your coaching approach is something I think about with with our group as well with our members? Are you tailoring your coaching approach to kind of meet the specific needs of each client? How's that work?

Eric Weiss: 12:36

Yeah, I'm not exactly each each client, but I definitely crowdsource. So I like to say it's, this is not a typical, this isn't your your dad's accelerator program. It isn't a course that you kind of jump into, and you run through a structure and there's a demo day and you graduate, and we take a chunk of equity. This is a an Agile process. I'm an agile evangelist, I always have been,I use it heavily in my coaching,that's actually where the name full cycle came from, is I'm always looking at feedback loops and continuous improvement cycles. And so the same thing in the accelerator. Every few months, I pull my members and gauge what are the biggest challenges that they're dealing with at the time. And then I craft custom customize the curriculum towards those challenges. So for example, this quarter, there's a lot of focus around fundraising. Everyone's trying to go out and raise money right now. It's really difficult. And so I'm having a really great expert on fundraising, come and do a workshop. And then we're going to do some challenges and some,some exercises around getting our story straight, getting our pitch really dialed in doing our market research and, and landing that that series a

Matt Wolach: 13:47

super cool, I love that. It's the ability to be able to take the feedback and take what people need and what's happening right now and turn it around and get them their their answers is so cool. So well done with that. That's really cool.How do you when you're working with somebody, how do you are you able to kind of draw from your own experience and what you've done to be able to help others kind of leverage their strengths and really maximize their potential?

Eric Weiss: 14:11

Yeah. Yeah, in some cases, I try not to I try not to rely on my own personal career experience, I really rely more on the perspective that I have working with so many different companies. You know, as, as an executive coach, I work with about a dozen companies at a time and in my accelerator, I have about a dozen clients, you know, coming by, so anywhere from, you know, 10 to 20companies at a time I'm seeing the patterns, I'm seeing the challenges that they're working with seeing what's working and what isn't working. And I hate to say you know, experimenting with some of them seeing let's try this over here. Ooh, that worked really well. Let me leverage that in my other clients and we tried that didn't work. Okay, not going to do that again. So I try to rely more on their experience than my own.Except when it comes to coaching Obviously coaching as a leadership style, obviously, I'm an expert in that. And so I, I lean in pretty heavily in my coaching experience trying to turn these executives into coaches themselves. Because that's really what it takes to delegate effectively. And that's what scaling up a team is all about, is being able to delegate effectively. It's not about manage, you know, management is about getting the task done,right. But coaching is about is about getting the ownership or transferring the ownership and the accountability of not just that task, but the entire role.And so that's really what it comes down to. It's just another feedback loop. Right? Coaching is a way of saying, Okay, go do a thing. Let me give you feedback, let me give you some guidance. Why don't you try this? Why don't we give you some tools and some frameworks to help you put it in perspective and continually improve? And I'm here for you when you need me,but you're the one in the driver's seat.

Matt Wolach: 15:54

That's, that's phenomenal. I love it. What are some of the biggest mistakes you're seeing that new leaders are making out there?

Eric Weiss: 16:00

Yeah, well, you know, the, the time honored tradition of of wearing too many hats, doing trying to do too many different things, and not delegating effectively, because we feel like we're so great at everything that nobody can do it as well as we can. Usually,that's wrong, we tend to maybe inflate our ego a little bit about how good we are at doing something. But also, we might be the best at a particular task,when we can focus on it. When we were an individual contributor,like, Yes, I was the best coder on my team, when that's all I was doing. But when I'm doing 17different jobs, I'm actually a pretty terrible coder, because I can't focus on it. So not only delegating the stuff that we don't like. But delegating the stuff that we do like or think we're really good at, is a really, really common pitfall that that many founders deal with. So not delegating early enough or not hiring early enough for those really critical roles. And, and not focusing across the business and really understanding the big picture of the business. So I talk about the mind, the model that I use is thinking like a founder versus thinking like an executive. So a lot of founders in the early stages, they're either really focused on product really focused on sales,typically. But that's not enough to build a business. So thinking like an executive is thinking about, what are the ramifications of this decision,or of this process, or of this product across the entire business? And how do we work together? How do we collaborate and coordinate, you know, it's not enough to build a really great product, we have to be able to sell it, we have to be able to market it, right? We have to be able to create a business model that that's profitable, or a pricing model that fits the market, and so on and so forth. So, you know, it's not just about wearing 17different hats, but it's being an orchestrator of all of these different functions into a cohesive whole. And that's something that takes a lot of maturity.

Matt Wolach: 18:03

Yeah, I totally agree. I definitely take maturity, I'm glad that they have you helping them with it,then what would you say are some of the qualities and skills that successful executives possess?

Eric Weiss: 18:15

Well, certainly, you know, humility, is probably the number one thing is just self awareness, of understanding what our strengths are and what our weaknesses are, not to the extent that it creates self doubt, or that it creates hesitation, because we also have to act decisively, even if we don't have all the information or all the skills, but just that self awareness that even if things are going incredibly well for us, there is luck involved.And there are other people that are that are helping us get there. So I would say is the the number one thing. The other one would be, I would say a resiliency or almost a buoyancy,if you will, that that challenges are going to come,you're going to take knocks you're going to take hits, and you got to be able to continue to push forward without letting it you know, get you down or, or I call it acting or leading out of confidence versus leading out of fear. So some of us when we get knocked, we get fearful,right? We're afraid we don't want it that hurt. We don't want to get hit like that again. So when we hesitate, we pontificate we get stuck in analysis paralysis. Instead, we have to lead out of confidence. It's actually one of the things I do is I actually do a kind of a meditation exercise, where I have my clients, you know, close their eyes, take a few deep breaths and think about that thing that was really scary for them. It could be you know, when when we lost a big client or I had to fire a bunch of people or we didn't make that fundraising or we were almost at a we didn't make payroll. Okay, where do you feel that in your body it's usually down in your gut somewhere? It's like a gut feeling it right now it's kind of this like tingling, right?Yeah, right that tingly, crackly feel feeling down in your gut.Okay, now think about a time where you were really confident when you when things were flowing when you were, you know,at the top of your game, and how does that feel? Okay? I'm feeling like a chills up, like up in my shoulders. I'm feeling right now, right? So now when I'm faced with a challenge, or faced with a big decision, take a moment and say, What am I feeling right now? Am I feeling that crunch down in my gut? Or am I feeling that tingle up in my shoulders? That tells me am I leading out of confidence or leading out of fear? And depending on what I'm doing, if I'm feeling that fear, I gotta reset, I got to challenge my assumptions, challenge my decision, and get to a place where I can feel some confidence.

Matt Wolach: 20:40

That's next level.That's amazing stuff. Eric, I love it. So, you know, as we wrap up here, what advice would you have for early stage software leaders?

Eric Weiss: 20:47

Yeah. You know,first and foremost, I would say,don't worry about the money,don't worry about the product,focus on the people that you're serving, I call it find your tribe. So focus on a group of people who you want to make a difference in their lives and their world. And there will be an overabundance of problems,and an over abundant abundance of solutions and potential products you can build. So don't get tied to the product, don't even get tied to the problem.But become incredibly passionate and obsessed with your customers. Build that empathy,build that connection with them,that's going to be the thing that's going to get you to stand up and dust yourself off and keep going. When times get tough. That's going to be the thing that's going to create raving fans and loyal, you know,loyal advocates for you. Because you're really putting them you know, first and foremost, and then do the same thing for your team as well. Right? Make sure that you're hiring people, not just because they can do a task or do a job. But because they're I call them your Avengers,right? They're your superheroes,they're all unique. They all have complementary skills. And you know, become that coach that they need to realize their full potential, and they're going to do great things for you.

Matt Wolach: 22:04

Phenomenal advice I love it couldn't have said it better myself. This has been awesome. Eric, I really appreciate you coming on and sharing all your wisdom with us.How can our audience learn more about what you're doing?

Eric Weiss: 22:14

Yeah, definitely.Well, so check me out at chaos to clarity.io. You can find my podcast there as well as links to my accelerator and various free tools and things that I offer there. You can also go to full cycle product.com, which is more of my sort of coaching and consulting business. Basically,either of those websites, you can also find me on LinkedIn.And I'm sure we can share all those links in the show notes.But connect with me, follow me download my tools freestyle, I love to give stuff away to founders and help them any way that I can.

Matt Wolach: 22:47

That's phenomenal.We'll put all that into the show notes. Make sure everybody has that. So click in there if you heard that and want some of that action. Eric, this has been awesome. Thanks for coming on the show. Really appreciate it.

Eric Weiss: 22:57

Likewise, Matt, it's really a pleasure. Great to see you again.

Matt Wolach: 23:00

Very cool,likewise. So everybody out there, thanks for being here.Really appreciate it. Make sure that you subscribe to the show.You don't want to miss up any of the people that we have coming up here. Now we've got some great guests and I want to make sure that you see them and hear them. So get that subscription in there. Also we are looking for reviews. So if you think this show is helpful for you, if you're learning how to get better at your company,definitely give us a review. I'd love to see it and make sure that we're getting you what you want. So thank you for being here. Take care. Bye bye.

Intro/ Outro: 23:31

Thanks for listening to Scale Your SaaS for more help on finding great leads and closing more deals. Go to Mattwolach.com