09: The CEO Journey - 4 stages of a SaaS CEO

Being the CEO of a SaaS start-up is a giant journey. Darren and Aaron discuss a recent podcast from a16z with David Ulevitch that lays out this journey into four specific phases a SaaS CEO goes through. We are each in a different stage of the 4 right now and we discuss how that looks to us and where we are trying to get to.

Helpful links from the episode:



00:12 Aaron Weiche: Episode nine, The CEO Journey.

00:16 INTRO: Welcome to The SaaS Venture podcast, sharing the adventure of leading and growing a bootstrap SaaS company. Here the experiences challenges wins and losses, shared in each episode, from Aaron Weiche of GatherUp and Darren Shaw of Whitespark. Let's go.


00:42 AW: Welcome to the SaaS venture podcast. I'm Aaron.

00:45 Darren Shaw: And I'm Darren.

00:47 AW: And we are back in front of a microphone, sharing our business secrets, our love secrets, everything in between, and making them public, so that we can share them with our listeners. And, if anything, sometimes it's probably cathartic and healing and everything else, wouldn't you say?

01:07 DS: Yeah, definitely, I have not yet shared any love secrets, so I'm not sure where you're going with that, but...


01:15 DS: May be a future episode. I don't know.

01:17 AW: I'm just trying to keep things broad, all the time, right?

01:20 DS: Broad, yeah. 'Cause you know we never know what we're gonna talk about.

01:22 AW: Yeah, no, if this turns into a relationship podcast on how you and I get along, and our friendship and being there for each other and everything else, we could pivot right, like, software is all about pivoting at different times.

01:35 DS: It really is, yeah, and I think we should definitely keep that in our back pocket.


01:40 AW: Alright, so with that, we'll both get up off the davenport and the attempt to talk on a few different topics today, especially the deeper content we want to get into on kinda the CEO journey. We have a lot to cover there, we will probably, once again, have a hard time keeping ourself to 40 minutes but hopefully the content is appreciated. But what have you been up to since our last episode on churn a few weeks ago, Darren?

02:12 DS: What have I been up to? Well, we've talked about this Local Search service a number of times, and how we're re-pivoting that actually, speaking of pivoting, into a Google My Business Management Service. And so I hired someone new for that. Basically Allie is my primary person that is running that service and she's at capacity, so we need to hire, and so can't really launch it until we have new people hired and trained and ready to do the service. So, I hired Sydney, she worked with us in the past, she's pretty awesome. And so she started yesterday.

And I put out a job posting too. And so we're just trying to get the people in place to be able to service the service because we have a waiting list of 30 people that are interested already. I don't even... Honestly, I worry that we might never even launch the landing page because we'll just keep picking people off the waiting list, 'cause the waiting less seems to be growing faster than we can hire and train people to build the service up.

03:10 DS: So, it's very interesting to me that there's that much interest in the service, I think it's gonna be very successful for us, and I think we've dialed in our processes really well. So, the next thing to dial-in, is hiring and training and scaling it up so I'm excited about that. That's big for us, for sure.

03:24 AW: That's awesome to have that type of demand. That part has to feel really good.

03:29 DS: It feels great, and I think it's like... I had read a tweet or some one... Some luminary of the modern age, had tweeted that the biggest success factor for companies is not really product or anything, it's timing. And so having the right product at the right time, that people need, and I feel like that's precisely what we're doing with this service. So I'm excited about that. And I know there's competition out there, but it's early stages. We have a great reputation that we've built up in this space, and so I think we're really well positioned to do well with the service.

04:01 AW: I'm interested, you seem to be comfortable in productized services and things like that, where the whole reason, not the whole reason but one of the reasons I got into SaaS after well over a decade in agency is I wanted to get away from services and I wanted to be strictly product-focused. But you have a good comfort level with that. But yet, man, I would be really, I would be frustrated right now. Like really, I gotta wait on services to get this awesome new thing launched?

04:32 DS: Totally. And you're like, you have a software, you just flip the switch. "Okay, sign up everybody." And so there is something beautiful with that. There are two types of services. There is a complex agency, SEO service where every case is different and everyone's got different needs, and some clients are more of a hassle than others. Same thing with something like web design where you're building out a website. There's just so many touch points with the client that it's really hard to scale that.

And what I have found is with a very simple streamlined one thing type of service, so citation building, for example, it scales really well. It's like, this is what it is, you buy it, you basically get a product, really, it's a very specific thing. And there's not a lot of back and forth, there's not too much... Not to many questions about it, right?

05:22 DS: And so everyone gets the same thing. And that's where the pivot happened actually, 'cause I had turned the Local Search service into something more complicated than it needed to be, which opened the flood gates for all of that like different clients and how do we handle practitioner listings, and just lots of complication. So scaling it back to just this really helps us to build something that's scalable. And so I am comfortable with this as a productized service but I totally hear you on just services in general. They can be a real pain in the ass and very hard to scale.

05:53 AW: Yeah, well, good for you. You are a braver man than I am and totally... Nothing wrong with it. Not in my wheelhouse of a fit right now but how is it right? You said you're posting, and I know this, I've talked a number of episodes on hiring, especially for sales positions, which I'll give an update on and we're continuing to do. But in talking before the podcast, you kinda have a few little tips for people in hiring and posting to job boards.

06:27 DS: So yeah, this, this job posting I actually forgot to do it when I first launched the job posting. I put out... So I posted the job and I had done this last time, but we use Indeed.ca, I think, I'll see if there's any indeed.com, but we post our jobs to Indeed and so, we get a flood of applications and most people, they just press the button to apply through Indeed.

I have a very specific note that says, "How to apply," and it says, "Include your resume and cover letter," and it says, "and email it to darren@whitespark.ca." It also says right in the, "How to apply," "If you just apply through Indeed, instead of emailing Daren directly then we'll know you didn't read this and it'll be really helpful for us for filtering our candidates."

So this is awesome because I get... So far I've probably had about 40 applications for this job and only five of them read this instruction. Most of them are just like, it's like a volume game, they apply to every job that's on Indeed, and I don't wanna waste my time with those people, I want people that actually took the time to read this, decided this if is a job for them, and they emailed me directly. And so I have three really solid candidates already, and I just posted the job yesterday, and then the other ones, they just go straight to the bin. I don't even look at 'em. I just archive them.

07:45 AW: Awesome.

07:46 DS: Yeah.

07:46 AW: Totally agree with you. We always ask, "Tell us about yourself, share links to wherever you're creating content or are a part of content on the web. And yeah, you get the ones that are just plain but the ones that actually take the time, you can see that they're just so much more of a qualified candidate. And it is amazing to like, if it's a job you really want or you're really interested in, put in the effort to differentiate yourself. It blows in my mind that people just fall short on that.

08:13 DS: Yeah, they don't care, they're just playing a numbers game, they're like, "Well, if I apply for 100 jobs I might get two interviews, and then one of those could turn into a job." They're just lazy.

08:23 AW: Finding a job should not be like a marketing funnel. I don't think.

08:26 DS: Seriously. And it's like how are they not a little bit more discerning in what they apply for? It seems like they're... Like people that just do not have the right skill set that we're looking for are applying for everything it seems.

08:37 AW: Yup. Well, that's a great tip. Include something that knows people care, they want it, they pay attention to detail and read things through before they take action. Those are all great pre-interview filters to help you know what you're dealing with.

08:52 DS: Yeah, totally. Also, we signed up for Stripe. We did the deal yesterday. So I've been talking with a salesperson over there. So I'm so excited 'cause we're building our new account system, and Stripe just looks amazing. My developers are doing the happy dance all over the place. Just getting off of PayPal, moving over to Stripe, and Stripe billing looks so nice.

Did you know they have this feature? This is a tip for all of our listeners. Stripe has a magical feature that will automatically update credit cards that are expiring. They have an agreement with Visa and MasterCard, and let's say your credit card is expiring, then, this system which only costs an extra 0.4% recurring revenue, will automatically update credit cards that are expiring. So you don't have to chase people with expired cards. Did you know that that was a thing?

09:44 AW: I didn't, I didn't at all. That is mind-blowing.

09:47 DS: Right? Holy, I'm so excited about that. So this is... I think it's fairly new. But he told me that and I was like, scrambling to find a pen, so I could sign this contract 'cause oh my God, that's gonna be such a great feature.

10:01 AW: Yeah, now there's a few. My CFO and some of our customer success team members would love to hear that. We run an internal report, and that will show us like, "Alright, here's who's failing, and we're communicating and making attempts." And then they usually get involved with a human reach out and it's only... It might be anywhere from three to 10 accounts in a month out of thousands that need that. But man, they would love to have that off their plate, and some of them turn into cancel billings, right? There's even more of what those are. So, wow, that sounds really interesting.

10:36 DS: Yeah, look it up. They got a new feature. I think you're already on it. Yeah, 'cause I recalled getting Stripe invoices from your team. So I'm pretty sure that you already have the feature. You just need to flip the switch, maybe.

10:48 AW: Yeah, no, we're not in Stripe, so.

10:51 DS: Oh, you're not?

10:51 AW: No, we're not, we're on PayPal.

10:54 DS: My condolences.

10:57 AW: Yeah. [chuckle] But, yeah, we'll see as our process, we're just starting in on the billing system stuff decisions and... Month down the road I'll have updates on what that looks like, but that's in step. But yeah, the payment processing might change for us some day.

11:15 DS: Sure. Well, what do you have updates on what's new in your world?

11:18 AW: Yeah, on the good side of things, really happy, I know I mentioned this in our last episode, but our customer success team with bringing in a new leader there, a couple of months ago is really going great. We've added on to our onboarding process where... We used to... We did a great job of getting people onboarded and set up, but we missed a number of opportunities to kind of be a little bit more consultative and outline things. And then once they got to, "Alright, go," then we just weren't as good as following up and making sure that things were progressing well. We were there if they had questions, but we weren't really leading them.

12:00 DS: Totally.

12:00 AW: And he already in a couple of months, Taylor has just done a great job of putting that together and getting that in motion and that was just a great example of things I know that needed to be done, but in being too many places and too many things, like it just was an area I can focus and I could lead, so I'm super happy with that. We're getting ready for... We have a couple events in the near future, Minnesota Search this week and their Summit which you've just spoken at and been at in the past.

12:32 DS: Yup, that's a great one.

12:33 AW: Yup. We're a sponsor at that, so excited to talk to all the local agencies and in-house marketers, at roughly around 300 to 400 attend that great one-day event. And then we're kind on a three-and-a-half weeks until MozCon. So really excited about that from every aspect. We're a sponsor from the biz dev side, seeing so many friends in the industry, yourself included, like it really is just a fun three or four days to everybody together. Yeah.

13:04 DS: Yeah, I can't wait. It's going to be so fun. We'll be hanging out.

13:07 AW: Yeah, on the sales side. So I'm trying to feel better about this. We did extend an offer to a new sales person on Friday. I'll know in the next couple of days, that they've accepted. I'm feeling confident that we're able to kinda meet the needs and we're a good fit for each other. But I was really, I was really trying hard to hire two or three at once and maximize training and get more output and things like that, and I just couldn't find out of the group I was talking to a good second or even a third candidate. So, a little frustrated.

I'm still... I wanted our outbound sales to be up and running months ago and just hitting stride now, but yet I'm still at the beginning and really actually need another body or two for how we're planning to work this. So, that part's a little frustrating, and I go back and forth between beating myself up about it and then having to re-motivate to, it's okay, these bumps happen and work through them.

14:09 DS: Hiring sales is so hard. So yeah...

14:12 AW: It is.

14:12 DS: And I think finding one good person is great and you might be able to get into this position where this new person is just fantastic. And that they're able to be the one that trains the next two people.

14:24 AW: Yep. No, absolutely. And then from an overall perspective, it's just been a lot of fun. Google's had a number of updates, lately. It just seems like they've been on a tear, it's still around local and other things, but we're just seeing reputation and in having a product with GatherUp being related to capturing customer feedback and generating online reviews, reputation is just... The easiest way put it is, it is becoming the most visible piece of data about your business.

14:53 DS: Yeah.

14:53 AW: Yeah, Google just released some things today. If you're Googling phone numbers for a business or an address for a business, they're attaching reputation call-outs to all those simple type of informational services. Two weeks ago, it was a Google Q and A. That feature having automated answering that, it'll pull up reviews related to the question you're being asked. So, this shift to consumer, customer-generated data in the form of reviews and Google is doing more and more and more with it. That's fabulous for us. It just plays into what we've been talking about and we haven't seen maybe these exact things, but we are really... It feels good to know that it's right in line with what we knew was gonna happen, we didn't know how, but we've really figured it would.

15:44 DS: Yeah, it's just like as I see more and more of these features come on, it's like, "Google's squeezing everybody else out, it's like they're just gonna become the only review site, it almost feels like. Other than a first party, it feels like Yelp is gonna get pushed out and some of the industry sites will get pushed out. It's just Google is doing such a good job of putting their content front center and really using their content. So, yeah, that's pretty amazing.

16:09 AW: Yeah. No, and I don't wanna steal any thunder from our co-founder and my friend Mike Blumenthal but he's had his finger on the pulse of this. And you're exactly right with that. And I think at the LocalU Advanced in Denver in September, I already have seen some of this data and studies. But you're right it's gone from a dozen review site players to really one review site player. And he has some really interesting data on how it's impacted Yelp and some of the other things. And for us it even pushes more the reason why we say first-party reviews really should be treated with a lot of respect and a lot of value, because if you leave everything, all of those eggs only into Google's basket, we just think that that that's just such a huge mistake and you're missing the boat on so many other things that you can do to both improve your business and market it.

17:01 DS: Yeah, is that new feature where they highlight the reviews, and then they show the different review sites on mobile, will it pull first-party into those?

17:09 AW: Yeah, reviews from the web?

17:10 DS: Yeah.

17:11 AW: Yeah, yup, it absolutely will.

17:13 DS: Okay.

17:14 AW: Yeah, there's just a number of things... I don't know... I'm just off the... Look, first party reviews are like the utility knife that a marketer really needs to focus on because it's a tool that you can use where GMB reviews are absolutely visible and have a great amount of visibility and draw to them, but you are just missing out if you don't whip out that Swiss army knife that's in your pocket to be able to MacGyver a million things on the marketing side.

17:45 DS: Yeah, totally. Totally.

17:46 AW: Well cool, with that, we kinda wanted to talk about a podcast. I was lucky enough, I had a long time industry friend who passed along this podcast to me and said, "Hey I think this would be of interest to you." So thanks, Ed Kohler, for passing that along, but it's the a16z podcast, and the topic of this podcast was really understanding that the journey and the stages of being a SaaS CEO. And the title of it and we'll link it in our show notes, you can give it a listen but it was, "What time is it?" And it was from being a technical to a product to a sales CEO. And the guest on the podcast was David Ulevitch. He founded OpenDNS sold it to Cisco. He's kind of morphed into a few different things now, he's on the VC side. But the high level of it and where I wanted you and I to discuss it, I sent it your way after listening to it, but it outlined that he looked at it as like four stages that every CEO goes through or has the opportunity to go through. The first stage is more of a technical CEO.

19:00 AW: You're trying to build it, get it built, is it feasible, do people want it? Then the next one you evolve into is being that product CEO, and now you're trying to figure out, do you have product market fit? You're doing discovery with customers that you think you have that with. You're listening to them so you can build the right features and evolve the right way, and ultimately are you solving those right problems? Then the next one is the sales CEO, and once you have that fit, now you're like, "Great, how do I generate more revenue so I can grow the company, acquire more customers?" And then lastly, if you are able to make it out of that is then you're that go-to-market CEO at the higher level. You have a VP of sales and a VP of Customer Success and all these other things and you're looking to, how do I scale and accelerate and have all the right pieces so that I can grow this as much as possible? 

19:50 DS: Yeah.

19:50 AW: And that simple look of it and just building it into four stages was something that really resonated with me that I looked at like, "Oh, I can identify with that," 'cause I've gone through... I wasn't a technical CEO 'cause I wasn't a founder day one, but I definitely came in and had to be the product CEO, and now I'm transitioning into that sales CEO.

20:13 DS: For sure. You see that as you build your sales team and as you personally experiment with some of this outbound sales stuff, like yeah, you're really into that sales CEO position right now. Does it feel that way to you? Are you still... You must still though go back to product 'cause you're always on... It's a big touch point. Like, what are the new features? How are we solving problems? What are the new problems that are coming up that we want our product to solve? So you kinda jump back and forth, do you know? 

20:37 AW: Yeah, no, I definitely do. I think if I had to pick one, I'm absolutely in the sales CEO. My initial thing a year-and-a-half ago when I kinda took the reins over, it was like, it gave me more control to get the right features that I felt were missing when I was out doing sales and interacting with customers. And I think we achieved...

20:57 DS: Right. Right.

21:00 AW: Better product market fit and we're able to do it in a good cycle. But I do. I wanna get to be that go-to-market CEO, the overseeing, and I have smart people better than me in all of these areas to do all of the right things. So I definitely wanna get there. But I do have a... I have a love for what we do and I'm very passionate about the high level of vision and problems we're trying to solve and things like that. So I think I'll always have a toe in the water over there on the product side. But, I don't know. I don't know if I'll always wanna be the stuck-in-the-sales-cycle, the one generating the majority of the bigger accounts.

21:38 DS: Yeah, I feel like I'm pretty firmly seated right now in the product CEO stage. I spent a lot of my time thinking about product market fit, trying to thinking about features, a lot of the sort of research I do, like I'm kind of in the trenches as an SEO still, like I'm not...

22:00 AW: Yeah.

22:00 DS: I spend a lot of time researching SEO things 'cause that's what I'm really passionate about. And so, that permeates into the products that we build and then I'm the one that's sort of reviewing everything that the team is building and advising on it and working on design and layout and so... And features. So I really feel like I spent too much time in the product CEO role, and I should have the right people in place that can do that for me so I can move to that next stage. That's sales CEO. This four stages, this podcast, is a little bit illuminating for me in like helping to direct maybe where I should be because I love being a product CEO, but in order to grow the company, I think I need to focus more on becoming a sales CEO. So this has been super valuable for me to think about it in these terms.

22:50 AW: Yeah, and that was a really big that... There's one comment that David made in here, right, where he said it's all about making the right decisions for the right time, and I feel like you just alluded to that, right, where you realized where you're at and then it's maybe... So what are your options to move out of that, right? Like, do you... I...

23:09 DS: Yeah.

23:09 AW: You need to find a product manager that can take over the product part and you...

23:13 DS: Exactly. I got one, I know who he is.

23:15 AW: Yeah.

23:16 DS: Yeah.

23:16 AW: Yeah, where you can still influence it and do whatever, but the lion share of it is off your plate so you can focus your time on the other, right? And that's... That's that same progression when I've looked at a number of these is like in order to get yourself out of it, you have to replace yourself there or find someone better than you specifically at that, and that can be hard too because to some extent, you might look at... Do you feel like you're better at product than sales and you'd only be doing sales because the company needs it, or what does that look like for you? 

23:46 DS: I feel like I'm... Like, when it comes to doing sales, like if we think about any enterprise leads that come in, I have a much higher close rate and I think because I'm so familiar with the product and the industry, it helps me to come across as very trustworthy, right? People wanna hire me because I know what I'm talking about, and it really helps to close the sale. So, I think there's a great opportunity for me to transition into a sales CEO and then build our sales culture, so then start to hire, basically get to the position you're at right now.

24:17 AW: Yup.

24:17 DS: And so... And I have a really good guy, Nick. He is fantastic. He could definitely be the product manager. I have him doing client work right now and it's like, "Man, we gotta just ditch those clients, bite the bullet and have Nick become the product manager and I'll step out of it and spend my time on sales."

24:34 DS: But you know what the trouble is? I'm the type of person that I only like to do what I like to do. [chuckle] And so, I don't love doing sales, and so that... I'm just like, "Argh, sales." Like sometimes it's like I'll have a great sales call and then it's like, "Yeah, sure, I'll send him a proposal eventually, I guess." Like, I'm just not good at staying on top of it and I'm not... I don't get pumped about sales and excited about closing the deal.

25:00 AW: Yeah.

25:01 DS: I just want money to come to me though I didn't have to do anything for it. I just wanna sit back and money just rains in.

25:06 AW: Yeah.


25:07 DS: That's what I want.

25:08 AW: And it does sound nice, but maybe that's where you realized like, "Okay, I actually need sales people," but they utilize you as an asset, right? Where...

25:17 DS: Yeah, maybe.

25:18 AW: Bring Darren to the call to build trust and answer so many questions and salesperson Sarah or Sam, they're handling the communication. They're staying on top. They're doing all those things, right? Like, I think there's ways to architect that.

25:32 DS: Oh, my, that's a genius idea, Aaron.


25:34 DS: I will do that because I love the sales call. I love being on the call and chatting with the clients and learning from them and it really helps to inform the product side too, right? 

25:42 AW: Yeah.

25:43 DS: So, I do love that, but I don't wanna put the proposals and statements of work together and go back and forth with legal. No thanks.

25:52 AW: Yeah. And I don't mind those things. I do, like I love to evangelize our product. I love to tell the story of what we do and show people, like just before we started recording today, I just got off a sales call, and we are taking someone from a competitor in the space and we are giving them exactly what they want at a massive cost reduction. Like it's just...

26:14 DS: Great.

26:14 AW: Yeah, wins across the board, and I love that. I get a high off of winning that deal and doing whatever, but I've realized over the years and in building agencies, like that self-awareness, here's what I'm good at, here's what I'm not very good at, and I need to find people who are good for those other areas. And then even if I like, even if it fills my tank to participate in those, then participate as long as you're not taking away from it and figure out what can you add to it without missing the gap on all of the other little pieces, right? I love being part of product, but if I had to be the product manager and all the detail and writing Jira tickets and all those other things, I would fail within weeks at that too, like I'm not a detail. I'm a big vision type person. So you gotta understand those things and then figure out how you can add to it and make it work.

27:08 DS: Yeah. I think it's a bit of a lesson for me. I tend to get way too detaily. I get really deep and I'm like, "Make this donut chart slightly thicker." Like I'm really fine into the details where it's a lot of my time, right? 

27:22 AW: Yeah.

27:22 DS: And so this is where a product manager would fill that role for me.

27:26 AW: Yep, absolutely. One thing that we talked about when we were kind of comparing notes on this was also understanding and you and I's world of running bootstrapped companies and limited resources, that some of this seems over-simplified and it's coming from someone with VC experience and revenue backed startups that's already there to play with it and everything else.

27:46 DS: Yeah.

27:50 AW: But what's really important is you can take from those. You can take from podcasts, from VC and big companies and whatever else, but it's finding the little pieces that you can work into your own framework, right? 

28:03 DS: Yeah, absolutely. Well, one of the awesome things from this podcast, I really liked where he talked about laying out your packages and plans. So I love that idea. What he suggests is taking your packages and plans and sort of designing them for your different customer profiles. For example, small businesses, agencies, enterprise in my case, right? And so they have different needs, and so I can push the different tiers based off of those needs. So something... So, small business is our base plan, and then if you want white labeling, well, you have to have the agency plan. If you want enterprisey-type reporting, you need to be on the enterprise plan. And so having those levers that will push people to the next tier is really smart, and I don't really do that right now. So I definitely took that.

28:54 DS: But yeah, it felt frustrating to be on a podcast, to listen to some of those things and think, "Well, those are all great when you are a CEO that has a leadership team where you can sit back and be big picture, but personally as a bootstrapped company, I feel like I'm running around answering everyone's questions." Right? So all the questions kinda come to me 'cause I am for the most part the leadership team, and so I'm not there yet. I don't have the resources to hire a leadership team. And so it is a little frustrating to hear these big picture things, but that's not to say that you can't take so much from it, right? 

29:32 AW: Yeah. Now, understandable when you look at it and there's certain parts of it, it's like, "Oh, they make it sound so easy and this is what you do and you have a lot of room to offer a salary and all these other things to implement that."

29:48 DS: Yeah.

29:49 AW: But for us, all I can say is that that's what's led me that I've already seen in scaling past businesses how important that was, and really in a couple of them, I was one of those pieces, right? I wasn't the CEO, but I was the one tapped to like, "Okay, Aaron will come in and handle sales," or, "Aaron will come in and handle the brand and marketing and putting this team in place."

30:06 DS: Yep.

30:10 AW: And what I saw in participating as part of those teams is like this is really where the company is run, right? Because if everything hits a bottleneck of one person, the CEO, or whatever that is, you just become infinitely limited in what you can do. But it's hard in those early days where that's all that you have room for is your one thinker and a lot of doers, but you need those additional thinkers and leaders within those areas to hit those bigger strides. But it's tricky on when who's the right one, especially your first one, right? How do I find the right person to trust, invest in and know that they have, they're in great alignment with what I wanna see done with the company? 

30:57 DS: Yeah. No, you're already a few steps ahead of me for sure in terms of leadership team. So you've got... Describe your structure right now. So you're a CEO and then you have a product manager.

31:07 AW: Yep.

31:08 DS: You have... You now have a sales manager, right? Yeah? 

31:10 AW: Not sales manager. That's really the last area I need to close. So I have one person that... I do kinda double as VP of product, but we have a product manager that handles all of the day-to-day and communication with their engineering team and all those pieces, so they are pretty much the owner of that area. We have a CFO to own finances, HR, hiring benefits, all of that kind of stuff. With the recent hire of a VP of Customer Success, I have someone that owns that team and is, like I said, in 60 days has already had a fabulous impact there. And then I have someone in head of design that he kinda works with the product manager for all interface design and feature design and all that kind of stuff. So it's a little bit of a tandem there, but that really gives me that.

32:01 DS: Yeah.

32:02 AW: And sales is that last place where it's like I completely own that right now. We only have one sales person on staff. We're trying to bring on a second, but I need to get enough bodies and I either need one to emerge as a leader that I can say, "Hey, this is yours to own and you need to build goals and you need to train and do whatever else," or I need to find that person. But right now I'm just at the stage where I just need more staff allocated to doing sales even more so than I need a leader or a builder of that area.

32:30 DS: Interesting, and you talking about your structure and all these different people and me thinking about me being that CEO bottleneck, one sort of spark of an idea that I just had was all these questions that come at me, it's a good exercise for me as a leader to look at that and say, "Who else could own this question?" Rather than me answering this, who could be the person that can make a decision on these things and then building up those people within my team and saying, "This is something you can handle," or at least, or thinking about a role of someone that can handle that and then slowly trying to siphon off these decisions, 'cause what does a CEO do? 

They just make decisions all day long, deciding what this should be, that should be, and it's like trying to put other people in positions to make those decisions for the company, I think, is the key to getting into that stage where I would be able to focus on being a visionary rather than the person that has to answer every question.

33:32 AW: Absolutely. And yeah, I don't ever wanna be that bottleneck and I don't wanna be the only resource too. Number one, I am incredibly opinionated. And sometimes that's a strength because I'm gonna have a strong opinion and I'm gonna do research and get experience to back it up and all those different things. It's not gonna be... It's not just gonna be thrown into the wind. There's a lot to support it, but on the other end of that, sometimes that causes me to just be too stuck in my ways or only viewing it one way. And that's one thing that I found by empowering other people and giving them decisions.

34:06 DS: Yeah.

34:09 AW: And then just creating... I think it's really important then to create a communication cycle where you're in the loop but the loop still goes without you, right? So you don't have to be in it all.

34:20 DS: Yeah.

34:21 AW: And sometimes I hear the decisions and sometimes I'm like, "Huh, yeah, I wouldn't have done it that way or thought about it, but that totally works," and sometimes has more success than what I would have dreamed up. And there's still are times where I'm like, "Wait a minute, how do that get decided? I think we missed some things," and whatever else, but those are just teaching moments that everyone to talk through it.

34:38 DS: Sure. Yep.

34:40 AW: So the next time that we have that we can approach it differently.

34:43 DS: Yep. Yeah, and the one thing I've learned more and more is that when I am not rigid on my opinion, then I often come around to the opinion of others and realize, "You know what? I think he makes some really good points and that is probably the best direction to go." And so I really try to be open and think about it from the different perspectives. I feel like that's one of the primary features of a leader, like you really have to be able to listen hard and listen well and think about what other people are suggesting 'cause that oftentimes, we'll have better ideas than you do.

35:23 AW: Yep. What would it look like for Whitespark if Darren said, "I'm taking the rest of 2019 off," who would own the different areas and make the decisions and whatever else? I think that would be an interesting scenario for you to play through in your head. And then how do you maybe implement some of those or start working through some of those things so that you can peel it away? Because I find and maybe you'd find the same, like I need space to think. I can't come up with big ideas or vision or the next partnership or whatever else if I'm just so far down in the weeds on little mundane decisions on how many pixels something is, not to say I still don't stick my head down in there, but I really shouldn't do that.

36:08 DS: Yeah, exactly. Well, you know what? I'm just gonna do it. I'm taking the rest of 2019 off. Good idea, Aaron.


36:14 DS: Thank you. That's it. I'm out. Good luck, Whitespark.

36:18 AW: Yeah, the Whitespark team is gonna send me some hate mail for sure.


36:23 DS: Yeah. No, it's a really great thought exercise and to think about who takes over because honestly, I go on vacations and I do work hard to disconnect and the company never falls apart. It runs just fine without me. When I get back, there's some decisions that are waiting for me, but I think it does come back to really trying to assign those decisions and empowering people on my team to make those decisions without me and rather than holding the reins on some of these things. So I'm gonna really use this as a starting point to look for those decisions and say, "Who else could make this decision instead of me?"

37:01 AW: Yeah. Ultimately, Darren, through those four stages, and you talk about how you're primed that second stage in the product right now, do you ultimately even wanna get to the fourth stage? Like is that where you wanna be? Because I think it's okay too to look and say like, "These things I am, this I'm not. I don't ever wanna get there. And if anything, someday I might hire a CEO and I just stay, I'm VP of Product," right? What does that look like for you? 

37:25 DS: I can tell you exactly. When I look at these four stages, this is what I wanna happen. I've already passed technical CEO, the feasibility, the building, but we have a pretty good product and obviously it needs a lot more work and that's why I'm spending so much time in product, in the product CEO stage because of churn, actually. David Ulevitch mentioned this on the podcast that if you've identified... We're talking about what time it is. Well, right now, what time it is right now, it is fix the product, and that's what we're doing right now. And so when the product is fixed, I think I would love to skip sales for the most part. I would like the model that you described where I am still on sales calls and I'm thinking about sales and I'm thinking about how to grow sales, but I'm not the person closing for the most part. And then once the product is humming and we can scale, then I would love to jump to that, go-to-market CEO stage and scale the business like to $5, $10, $100 million.

38:26 DS: That is my dream and that is where I want to get in the next five years. I wanna get there, and I think I can get there and I do think it really comes down to getting the right people in place at those stages, because once you get a really good product manager, you don't have to be a product CEO anymore. Once you get an awesome sales director, you don't have to be the sales CEO and then you can really focus on being that go-to-market CEO. And so these four stages are really... It's a really great framework to think about as the leader of a company and trying to say, "How are we," and then make your plans, right? Plan out how are we gonna get to those stages and what do we need to do to reach that stage? And for me, I know exactly what it is for the most part. It'll evolve over time, but I know how to get there. And so I think our road map looks pretty good for that, but I'll be a product CEO for at least another year I think.

39:20 AW: That's a brilliant take, and I think the most important thing when I look at that is just that self-awareness, where even he broke down, it's really about asking where are you right now, "what time is it? ". You just answered that, and where do you wanna go. And sometimes, especially when you're so busy in the business, you don't step out and look at a framework like this or see, what type of leader do I need to be and where do I need to be focusing that gets us to the right place? 

39:49 DS: Yeah.

39:50 AW: And just as you're there right now, that... It's still, as you alluded to, I still have my hand in that a little bit, but we fixed a lot of the things that we needed to have that product market fit where I didn't get my rear end kicked on the sales calls I was on, and even to some extent, there's a couple more things we're releasing this year which really takes my confidence to an all-time record high, and it shows in your sales call. That's, if anything, I probably only did the product CEO so heavily just because I knew what I needed to sell to be the sales CEO, and I knew if I was gonna go into the ring and just get my butt kicked every time, it was gonna crash and burn.

40:28 DS: Yeah.

40:33 AW: The product had to be better. We had to shore up some of the gaps and we were able to do that. But you have to realize that, and if you're only doing... If you're not pulling up and looking at it from this level, you're gonna miss seeing that. If you only look at it in the four or five clear stages, you're not really understanding where you're at. You might not get yourself out of that stage to ever get to the next one.

41:00 DS: Yeah, exactly. This framework really helps you to see where you need to focus. Yeah, it's so defeating when I, as a sales, when I'm wearing the sales hat, when the leads come in, it'll be like... We have 10,000 locations. This is a major company that wants to work with us.

41:14 AW: Yep.

41:15 DS: And we don't have the product for them. This is what I face on a weekly basis, really great leads that I can't service. And so this is where... This is why I'm a product CEO right now. I'm a product CEO because I have to fix our product so that we have... These people are coming at us thinking we have it when we don't actually have it, and so we're building it right now, and I can't wait to have it so I can sell it to them.

41:38 AW: Then you just say, "Yep, here is your contract to sign."

41:43 DS: Yeah, exactly.

41:44 AW: That's awesome. Well, hey we, as I mentioned, we will link to this episode of that podcast in our show notes. Give it a listen, again, if you're a bootstrap company. Most likely you are. That's why you're listening to us as we put out episodes. It isn't about mirroring the VC. They're different. All those things are different, but there's just so many great little details and frameworks to pull out and hopefully us talking about where we're at within this four stage of the CEO's journey is helpful to you and hopefully you can take a look at it and figure out how you're, where you're at in it. Anything you wanna communicate on what's coming up or next for you, Darren before we talk again in a couple of weeks? 

42:30 DS: No, nothing big to announce. I'm gonna go to LocalU this week in Johnstown, Pennsylvania. So I'm looking forward to seeing some of the LocalU friends, Mike Blumenthal, Joey Hawkins, Joel Headley. So I'll be, great to see.

42:41 AW: That's a great group.

42:43 DS: Yeah, really great, and I can't wait to hang out with you and the rest of the get list or the gather-up crew at MozCon. Man, I can't wait for that. It's gonna be fun.

42:51 AW: It'll be a great week in Seattle, and yeah, we'll have to, no matter where we're at in our cycle, we will have to record the MozCon in person episode.

43:00 DS: Yes. We should actually get that on the calendar so that we know exactly what time we're doing it and we make it happen.

43:06 AW: Yeah. And something tells me it's gonna be somewhere where we can have a beverage in front of us to help with all the conversation and ideas.

43:12 DS: Yeah, with laptops far away from those beverages.


43:16 AW: My wife actually told me I can't do any more jokes on you for spilling the beer. She said I wore that out, so I'm glad you did the joke instead of me.

43:23 DS: Yeah, I brought it up.

43:24 AW: Yep.

43:24 DS: Yeah. So you're off the hook on that one.

43:26 AW: She's the most critical listener of the SaaS Venture. So...

43:30 DS: Great. It's good to have a critical feedback person. Yeah, for sure.

43:33 AW: Yeah. You passed with flying colors. You know you're an arm's length away. You can do no wrong. But I gotta work. I gotta work on my game, so...


43:42 DS: Alright.

43:43 AW: Awesome. Well, thanks, Darren. Thanks everybody for listening. We're always trying to grow our audience. So writing a review on Apple iTunes would be helpful. Sharing a link to one of our episodes on social media or letting people in your Mastermind group, your LinkedIn group, out on LinkedIn, any of that, we would so appreciate it. We're excited for the hundreds that we reach, but we would love to have more. And as always, if you have an episode suggestion or an idea, hit Darren or I up on Twitter and we would be happy to try to work that into our topics and into the upcoming shows. So with that, Darren, have a fabulous time at the LocalU event coming up, and I'm excited to see you in Seattle in July.

44:26 DS: Alright. Yep, you too. Have a great week. Talk to you later.

44:29 AW: Alright. Take care everybody.

The Saas Venture Podcast from Aaron Weiche and Darren Shaw