Richard Harris shares insights and lessons learned over his 20+ years of technology and SaaS experience

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Episode Outline

[04:39] Richard’s background

[07:16] Understand that early customers are buying that CEO's passion, that founder's passion

[10:13] Importance of getting a quote from the decision maker of the deployment

[11:18] Realize that your customers aren't fortune companies with big legal team

[12:04] “If you're a one to 10 million and you're going after a new customer, what's the first thing your potential customer is probably going to ask you about?”

[14:34] So everybody wants a discount, know that's going to happen and get your leverage

[16:35] Situation that they have a legal department they're just red lining for the sake of red line, they just know to eliminate everything. They don't really stop and read that.

[17:04] Success depends on how, how strong the marketing leader is in understanding sales.

[19:22] Importance to relearn and unlearn that process. Those who've taken that stronger leadership position accelerate faster.

[20:19] Why it is crucial to redefine product market fit and to re-onboard our entire organization to work from home.

Richard's inspirations:

Blake Hudson

Dickie Walsh

Lori Richardson

Connect with Richard:



The Harrison Consulting Group

Elias Rubel: (00:02)
Hey there all you cool cats and kittens. And welcome back to another episode of best in SAS, where each week we take you behind the scenes for conversations with some of Silicon Valley's best and brightest operators and investors, crack a beer, get comfortable and join us on our quest to find the patterns and playbooks that accelerate the sprint to 10 million of that good stuff. That repeatable stuff, that stuff we call a R R. So today's guest has clients like Google visa, zoom, Intercom sales, loft, Terminus, Gainsight, Panda doc. Datanize Richard. Welcome to the show.

Richard Harris: (00:41)
Thank you. I appreciate it. Good to be here.

Elias Rubel: (00:45)
So, you know, today, I thought we'd do something a little bit different because you see so many patterns and so many organizations on the site, sales and revenue side, uh, what are some of the things that you see just butchered time and time again, that you come in and you have to clean up and coach. So it's a good question. Let me ask you to dive in a little bit. Are we talking sort of that zero to $10 million size company, the 10 to 50, 50 to 100 million? Like just cause there's always context, right? Cause that's a great question. I'd say, let's assume that there at at least a million in ARR, so they're probably post product market fit in some capacities or some repeatability and they're, they're looking to make that first sprint to 10. Gotcha.

Richard Harris: (01:30)
Um, I think the couple of mistakes I see one is that they forget, or they don't know that sales is hard. Sales is not easy if you've gotten to a million in ARR, um, you, most of your clients might be friends and family, right? It also depends on what level of VC funding you have and the introductions you've gotten, which are great. Like, I think that's fantastic, like take what you can get. Um, but then when you start to go after outbound, cause you know, nobody knows you yet unless, you know, unless you're really, really, uh, fortunate, um, they forget that it's hard. They forget that it's not easy. They forget that as the founders CEO, the early customers are buying that CEO's passion. That founder's passion as much, if not more than the actual product or service itself. So that's the first mistake. The second mistake I see people make.

Richard Harris: (02:29)
And again, you know, I don't even want to say mistake. I, I, it's not fair if someone just doesn't know yet, right? It's not a, it's not that kind of thing. So I think the next thing that I see is that they forget to start writing down their use cases in case studies like wholeheartedly, you know, those first five to 10 customers, you need those stories documented. Um, and I make this recommendation to everyone in every one of your contracts. Everyone, you have a default marketing logo usage piece. And in that it says that they agree to a case study.

Richard Harris: (03:13)
They agreed to a case study that they'll agree to a quote from the CEO or founder, a quote from the decision maker of the department using it and a quote from the end user by default, that's an every contract I send out. Um, I love that. I want to, I want to zoom in on that before you keep going. So, cause I, I, you know, I'm familiar with like the, you know, get permission in the contract to use their name in a case study or that they agree to a case study pending certain success metrics. But I love that you're isolating each persona in the deal. What do you find? I mean, there's so many times you put that in there and then you get pushback. How in the sales process do you navigate the pushback that you get without, you know, you want the deal to close.

Richard Harris: (03:59)
You also want to be able to use them as social proof. Right? So here there's a couple of thoughts. I would change your mindset. So the first thing is, particularly if you're zero to 10 million, a lot of cases, your customers, aren't fortune companies with big legal teams. I can say at least 30, probably no, it's probably like 60 to 70% of my clients just sign it. I don't even know if they ever read it. Like they don't even stop to read it or they don't care. So that's the first thing. The second thing is I want them to push back on it. Cause I already know what they're going to push back on in the first thing, Eli, what's the first thing someone's going to ask you if you're a one to 10 million and you're going after a new customer, what's the first thing your potential customer is probably going to ask you about, uh, I mean, they're going to want to make sure that there's something worth talking about and they want to know about the ROI.

Richard Harris: (04:53)
Let me rephrase that. You're in the contracting phase, right? Yeah. Talking about doing a deal. What's the one thing we know that everybody's going to ask for an out clause or a big fat this Oh yeah. All right. Well that went right over my head. They wanted this now. So everybody wants a discount. Well, I already know that's going to happen. Well now I got my leverage. So push back all you want now for me and what I do. And it's different, I think, than a lot of places just cause I have that clause in my contract. Doesn't mean I'll give anybody a discount. In fact, I rarely do. But if it is the right logo, right, if it's, you know, big zoom or Google, you know, I'm going to try and put that clause in there. Right. Um, and when they ask for the discount, then I can say, Hey, more than happy to do that.

Richard Harris: (05:48)
But I need to guarantee you're going to give me those things right now. I've got leverage, Hey, whatever, I give you an a discount. I got to make up with the next customer. And there's not a business person in the world who doesn't understand that concept. Every CFO gets it. Everybody does. Right. And you're the biggest pushback you're going to get that I've found, particularly with your zero to 10 million, the biggest pushback you're gonna get is from someone who's really good at legal. They, if they have a legal department they're just red lining for the sake of red wine, they just know to eliminate everything. They don't really stop and read that. Like they read it and they're like, no, we have a policy about not letting people use logos. So I'm just gonna scratch the whole paragraph. So even when that gets scratched, I can still push back.

Richard Harris: (06:35)
So the thing that I want people to remember, what, particularly when you get to the contract and phase, when you're there, they've emotionally committed to you. It's not done. It's never done until the paper signed and depending on how competitive it is, they're not going to let the deal get ripped apart because a logo usage, they think that you're afraid of that. And that's possible that you're afraid of that, but you have more leverage there than I think most people like. And I'm going to pause here because I know I've been [inaudible]. Yeah, no, no, no. That was a great, that was exactly what I was hoping it would be. All right. So let's get you back up on the soap box of like you've been around the block a long time. You've been coaching some of the best organizations in the world on sales. What are some more of the things that you just kind of like face Palm?

Richard Harris: (07:25)
Oh, this again in that early revenue sprint. Yeah. Um, so one lack of a decent CRM, lack of a process. Can't stand it when there's no process. This one bothers me the most, um, is when you actually pay, make your SDRs or AEs actually do research and data entry. It's the most expensive data entry I've ever seen. And it's a double edged sword because if I'm only working eight hours a day and I'm an hourly employee, if I've got to spend an hour and a half to two hours a day looking for data to get into the CRM, not only did I lose that hour and a half of hard costs, I also didn't make a single phone call to generate business. So over the course of a week, I've lost five to eight hours over the course of a month. I've lost 20 to 30 hours of time because I'm doing data entry, right.

Richard Harris: (08:26)
And those 20 to 30 hours, I should then be able to extrapolate out, okay. If I want them to make, you know, 10 calls per hour and four emails per hour, that it gives me to here. And if I see my conversion rate to there and that conversion rate to close, well, it didn't just cost you the hour and a half of time. And their base salary, it's actual true revenue. You lost because you're making somebody do data entry, which is ridiculous. Still. I wanna, uh, talk, you brought up SDRs, uh, I'm curious, do you think SDRs sales side or marketing side? Where should they sit? Um, it depends on how, how strong the marketing leader is in understanding sale and, and they don't have to be that's okay. Like I it's, everything's falling under the revenue team now. Right. And which now people can be specialized and the revenue person can make this decision.

Richard Harris: (09:27)
Um, you know, if I've got someone like Sidney Sloan from sales law, um, who really gets sales and she wants to own the SDR team, I'm all for it. Right. Um, otherwise I do tend to, like, I do feel like there's greater alignment with the sales leader, but it's not, you know, it just depends. And let's be honest if we're still talking about the zero to 10 million, it's a little bit more of a Trish for Tuesday. You said as well as who's got the bandwidth to do it importantly, do it mean to actually sit and coach not overlook and be a dashboard manager of them. Yup. Right. So that, that's my answer. So in that specific space, as you get bigger, then it can become a much more strategic and tactical decision. Right? Sometimes it's just a practical decision, zero to 10 million, where do we do this? You put them under whoever can do the most coaching.

Richard Harris: (10:26)
All right, let's get you back on the soap box. What's next? You tell me, what do you got? Well, let's instead of doing all of the negative things, let's flip this around. I want to know, and it doesn't even have to, it could be, it could be teams that you've worked with. It could be teams that you have observed and, and know something about what are some teams who have kind of defied gravity as far as how quickly they've grown in the industry in the last let's call it five years. And what do you think it was that really made the difference that separated them from your kind of good teams to just being like exceptional. These numbers don't even make sense, just amazing growth. Um, well I think it's a, it's, it's a stronger leadership team who understands how to manage human beings, right?

Richard Harris: (11:20)
So I'm a gen X or, and I'm of that generation of, you know, STF, you get back on the phone. I had to learn, I had to relearn and unlearn that process. So I think those who've taken that stronger leadership position accelerate faster. Right. I think that those who are willing to acknowledge, um, such things as you know, and mental health day is a good thing. That's a, that's a big indicator for me cause everybody needs one. Um, I think those who have adopted technology obviously accelerate faster, uh, I think the whole sales enablement space, which, you know, I think we typically think of, you know, everything from connect leader to vanilla, soft to sales loft, to outreach, to, um, uh, Videolicious, to, you know, all the video platforms those have all done really, really well. Um, just because of the cost of technology has gotten to a place where it's palpable, where we can tolerate it right.

Richard Harris: (12:22)
Where we can actually build something and sell something that doesn't break the bank. Right. So that those are the places that I've seen the most accelerated growth. Um, so I think that's, that's the biggest piece. So it's the ones who are willing to adopt the technology. So what do you see as shifting in the landscape from a technology and selling perspective? I mean, obviously everything just shifted, right? Your it's harder to do. It's harder to campaign to people because they're now at their homes and not in their office. And people are inundated with digital campaigns and outreach and noise because that's how everyone gets to reach them now in lieu of, uh, events and conferences and being able to do those field activities. How do you see the landscape of sales shift? Because obviously marketing has to shift in a major way right now, but how do you see the landscape of sales shifting?

Richard Harris: (13:18)
Well, I think that always come back to what's your product market fit. And so for the last 90 days, we've had to redefine product market fit and we've had to re onboard our entire organization, right. To work from home. Then you have to re onboard boredom coming back to the office. Right. Like there's just, those are the biggest shifts I've seen. Um, obviously I think the biggest shift that I will see is I think the SDR is going to come roaring back first way before eight. Um, because why would I want to go higher, expensive eighties? Right. Like I don't have business, I don't have meetings for them. Why would I hide? And you know, if you're saying, well, they've got a Rolodex, you know, my first, my first question is if you, if you use the word Rolodex, when you consider hiring a salesperson anymore.

Richard Harris: (14:11)
Right. So find a better way to say that. Right. Um, so that's sort of my that's where that's the big change. I think that's going to happen in the sales world and people ask me all the time, well, what should I do next? I'm like hire two or three SDRs. And they're like, well, when do I hire a salesperson? Well, as soon as you can't handle it anymore like that, right. That's not how I look at. It would have been some of the hardest lessons for you personally in your career. I mean, you've, you've really just rocketed up to the top of, of sales, training and coaching. So I'm curious, surely there were some stumblings and hard lessons along the way that have made you as good as you are today. Well, first of all, thank you. Um, it's interesting. Cause I, I suffer from a terrible imposter syndrome. Um, cause I'm like, I'm not at the top. Like as soon as you said that, I'm like, yeah, this list came out and this list came out and this list came out and granted their lists by whoever, you know, and I'm kinda like, you know, why do I care? But then I do care. Right? So, so it it's annoying for me that I am annoying to me, not you asking me that I annoyed myself.

Speaker 3: (15:25)
Um, that's probably the honesty.

Richard Harris: (15:27)
It was probably one of the hardest lessons for me is to, is to be willing to accept that I do belong here and that I am good enough, even though, you know, you read off all those logos and sometimes, you know, if I'm in a slump, I'm in a slump like everybody else, right. It's not fun. Um, so I think that that's a, that's a big thing. I think, um, you know, I'm a big proponent of supporting mental health. I wish I'd understood that earlier in my life, not just in my career. Um, do I think my own mental health? Um, probably, well, I know it held me back because it let my ego get in the way. Um, I actually just had a conversation this morning on our coffee talk session about, you know, biggest mistakes I've made, um, and not understanding that, uh, is, has been a big challenge.

Richard Harris: (16:15)
Um, and, and keep in mind, you know, when I say mental health for those listening, um, I'm lucky in terms of mental health, I'm not someone who's ever wanted to hurt myself or hurt others or, um, had a rage issue or any of those kinds of things. I'm just a guy who's sad all the time. I have depression and um, and I've been working on it for a long time, so I feel good about it, but you know, so mental health for me, isn't, you know, isn't, isn't sort of off the deep end that I think sometimes people think about. So that's probably one of the biggest challenges I've had to get over. Um, I also think getting out of my own way to just go for it, right. I, in the last year I've gotten way better at saying yes. People ask me to do stuff.

Richard Harris: (16:59)
Yes. Eli pings me and says, you know, can I be on your podcast? The answer is yes. Right. I don't stop and overthink it anymore. Don't stop and go, well, let me go see who this guy is. Does it look like he has a lot of followers? Like, it doesn't matter anymore. It's just me getting out there. Right. So, uh, so that, that's sort of how I see it. I, I, that was a very long answer. So if I didn't answer properly reel me back in. No, no, that was, that was a really, I appreciate your answer. That was a very real answer. And I feel like people in the Valley don't talk necessarily about mental health as much as we probably should. So I appreciate it anywhere, but it's got nothing to do with the Valley. Got nothing to do with West coast. In fact, if anybody does talk about it more than other places, it's probably California, but it's, and what's worse is it's it's, you know, mental health just I'll go off on a little bit of a rant is it's non-discriminatory, it doesn't care how much money you made.

Richard Harris: (18:00)
It doesn't care how much money mommy and daddy made. It doesn't care how rich it doesn't care how poor it doesn't care, uh, of your, of your ethnicity. It doesn't care of your, uh, uh, sexual orientation. It, it does not care. It will literally attack everyone. It, you know, and, and you know, it, it just it's there. So, uh, so for me, it, one, it's hard for men to talk about it. Cause we were all raised in a time where it was like, you know, um, and on the other side of that is, you know, I've talked to some of my African American friends. It's even harder for African-Americans to talk about this topic. Um, one, not so much from a, from a, from a, uh, a male and I've talked, I know I'm only saying this from the male perspective, cause that's who I've talked to about it, but there's a concerned that if someone is going to see a tree, I don't know if that word's right.

Richard Harris: (19:03)
Caucasian therapist, if you come from a different ethnic background where they really going to understand, right. Is if I were a therapist and I, as a white guy, you know what I really understand the plight of an African American band twisted pulled over when he finds his life with dirty beers, I've never been pulled over. So there's, there's, I think there's a legitimate concern about trusting the process, um, which I hope we can eventually get passed and that the people can realize that a good therapist will see. So, um, again, going off a little bit over the ramp, but this is an important topic. And so when I'm given the opportunity, I talk about it. Sure. Yeah, absolutely. So what do you do to take your mind off work? What, what calms you down? What gives you clear head space?

Richard Harris: (19:51)
Um, so it's big for me, I'm a huge meditator. Um, my kids and my wife are really good for me. Um, I have a hard time that I'm, cause I really do enjoy my work and I probably bury myself too much in it. Um, and probably need to step away more. So I'm very conscious of that. I'm trying to implement a new walking talk strategy that I learned from Galen, uh, this woman who I've been speaking with lately. Um, and, uh, you know, she, you know, there, there are conversations that I talk to people all day long. I don't necessarily need to be in front of the zoo. I can be on zoom and in my car, I can be on zoom, sorry, not in my car, but you know, walking around the neighborhood just to get out and get a little exercise. So I think that's a really important piece.

Richard Harris: (20:40)
Nice. And then my last question for you as we wind this down, who are some of the folks who have inspired you along the way and perhaps in part of your journey to where you are today? Um, Scott, Lisa's a huge piece of that, um, guy by the name of Scott Tobias. Um, another guy by the name of Kenny stocker, I'm trying to think. Um, uh, another guy named Dickie Walsh Trish for Tuesday has been really good for me in the last few years. Lori Richardson has been good for me. Galen has been really good for me. Um, uh, I'll tell you, who's really like literally, and I'm not kidding when I say the last week, um, Blake Hudson, who is just on the surfing sales podcast, super smart, sharp guy, really just so far advanced in his wisdom. Um, really enjoyed him and, and you know, it's interesting, he's in his, he's in his, you know, ran for state Senate in Illinois at the age of 24, like legit ran and didn't win. Exactly. But wow, like what the fuck was I doing at 24?

Richard Harris: (21:51)
And then till we go, well, you know, he didn't decide that in 24, he probably decided at the age of 22 or 23, right. Like it's just amazing. Um, so, you know, so he's way younger than me, but he's one of those people I I'm actually gonna have him mentor me. Um, and I'm not kidding when I say that. So, um, so that's sort of my thought on those kinds of things. Very cool. Well, Richard, thanks again for taking the time. It's always a pleasure to chat and I'm sure our audience learned a thing or two through a, through our conversation today. So thank you. Thanks. I appreciate you being here and asking those questions. Absolutely take care.