Collin Stewart is the Founder and CEO of Predictable Revenue, a sales outsourcing company that helps B2B businesses build repeatable, scalable sales development teams. Under his leadership, Predictable Revenue has become a recognized leader in sales consulting, delivering over 10,000 booked meetings and scaling outbound sales for more than 55 companies. Recognized for his data-driven, practical approach to solving sales challenges, Collin also hosts the Predictable Revenue podcast, which boasts over 400 episodes.
Here’s a Glimpse of What You’ll Hear:
- [2:14] Collin Stewart recounts how his childhood hustle built his entrepreneurial drive
- [4:07] How officiating hockey games built unshakeable confidence
- [7:39] What happens when you skip true customer development?
- [15:46 Why rapid product growth can break your business overnight
- [22:34] How today’s cold email landscape raises the stakes
- [27:26] Why targeted messaging still dominates cold outreach
- [28:56] The founder’s guide to nurturing leads for long-term wins
In this episode…
Struggling to turn sales calls into paying customers can feel like hitting a wall, even when your tools and tactics seem solid. Many founders assume their scripts or CRMs are the problem. But could the real problem run deeper, with outbound sales success depending less on what you say and more on how well you listen?
Collin Stewart, a seasoned entrepreneur and sales expert, discovered this lesson the hard way. He spent years building a CRM to compete with industry leaders, only to realize sales teams didn’t need another tool — they needed clearer processes and better support. By asking questions instead of making assumptions, Collin aligned his solutions with real customer pain points and unlocked lasting growth. His advice is simple: listen closely to your customers before building anything.
Tune in to this episode of the Smart Business Revolution Podcast as John Corcoran interviews Collin Stewart, Founder and CEO of Predictable Revenue, about effective outbound sales strategies. Collin explains how active listening drives better product–market fit and shares insights on nurturing early leads, avoiding over-automation, and landing your first customers on a tight budget.
Resources mentioned in this episode:
- John Corcoran on LinkedIn
- Rise25
- Collin Stewart on LinkedIn
- Predictable Revenue
- Entrepreneurs’ Organization
- The Predictable Revenue Podcast
- The Terrifying Art of Finding Customers by Collin Stewart
- Predictable Revenue: Founders Edition
Special Mention(s):
Quotable Moments:
- “Cold email is still effective, but the table stakes have gone up — what worked before won’t cut it anymore.”
- “Most companies fail at outbound because they give up too early, not realizing it just hasn’t worked yet.”
- “The most important piece is the connection — today, it’s about sending a few hundred really targeted emails, not 10,000 blasts.”
- “I don’t give up easily. I never wanted to quit; I wanted to figure out the answer to the problem.”
- “If you reach out to start a relationship, nurture it, and stay helpful, you’ll be top of mind when customers are ready.”
Action Steps:
- Listen deeply to your customers and prospects: Ask open-ended questions to uncover real pain points and avoid building solutions that don’t meet actual needs.
- Refine your outbound targeting and personalization: Build intentional lists and craft messages that align directly with each contact’s current context.
- Nurture long-term relationships, not just quick wins: Establish follow-up processes to convert leads over time instead of discarding them too early.
- Embrace iterative learning and willingness to pivot: Stay open to feedback and adjust course when needed rather than clinging to failed ideas.
- Leverage creativity and multiple outreach channels: Use varied and unique engagement methods to stand out and be memorable in competitive outreach.
Sponsor: Rise25
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Episode Transcript
John Corcoran: 00:00
All right. Today we’re talking about why you’re killing your own sales calls and what you need to do about it. My guest today is Collin Stewart. I’ll tell you more about him in a second, so stay tuned.
Intro: 00:12
Welcome to the Smart Business Revolution Podcast, where we feature top entrepreneurs, business leaders, and thought leaders and ask them how they built new relationships to get where they are today. Now let’s get started with the show.
John Corcoran: 00:29
All right. Welcome, everyone. John Corcoran here. I’m the host of the show, and you know that if you’ve listened before, every week we have smart CEOs, founders, and entrepreneurs from all kinds of companies on this show. We’ve had Netflix and Grubhub, Redfin, Gusto, Kinkos, Activision Blizzard, LendingTree.
Check out the archives. Lots of great episodes for you to check out. And before we get into this, this episode is brought to you by Rise 25, where we help businesses to give to and connect to their dream relationships and partnerships. How do we do that? We do that by helping you to run your podcast.
We have the easy button for any company to launch and run the podcast. We do three things strategy, accountability, and full execution. We’ll even send gifts on your behalf if that’s what you want to do. And so go to our website. You can learn more at Rise25.com or email our team at support@rise25.com and my guest today is a podcaster has gotten over 400 episodes, which is really exciting. That is in the rarefied air top 1% of all the podcasters out there. And his name is Collin Stewart.
He’s the Co-founder and CEO of Predictable Revenue. He’s based in Vancouver, Canada. He co-founded VoltageCRM back in 2012 and later Predictable Revenue a couple of years later, focusing on helping companies to build outbound sales development teams. And so we’re going to talk a bit about how to get really good at sales in today’s day and age. And but I always love to start getting to know our guests a little bit about what they were like as a kid.
And, Collin, you said that as a kid, you’re basically slave labor. Slave labor as a young kid, you started with helping neighbors with garage sales and then you basically indentured servitude, decided to go start working in a warehouse at a young age. So tell me a little bit about young Collin. What you were like. You were raring to go, like, forget about soccer balls.
I’m going to go to work.
Collin Stewart: 02:14
Yeah. I remember buying a in. It was the like, library our library used to have, like a book fair every year. And you would have to, you know, get a little money from your parents. And I remember buying a Lamborghini Countach picture.
Obviously not a Lamborghini. That’d be like a Lamborghini.
John Corcoran: 02:32
Like you saved a lot from that. Those garage sales.
Collin Stewart: 02:35
I was a wealthy six year old. Let me tell you, John.
John Corcoran: 02:37
Yes, those counters man, those are hot cars.
Collin Stewart: 02:41
Very hot cars. And I remember having the like I bought the poster, it hung in my bedroom. And I remember telling my dad like I wanted to get one, and him explaining to me exactly how much it cost. And I just it was like an unfathomable amount of money. And I was like, okay.
He’s like, if you want one, you can do it, but you’ll be able to, you just have to work really hard. And I think that stuck with me. And so like I, I had a paper route I would help out at garage sales. I refereed hockey, you know, good Canadian kid. And then at 12 I think it was 12, I think because the law there was like a legal limit to work.
But you could start at 12 if it were a family friend. And my neighbor owned a warehouse, a textiles warehouse, and they had a factory outlet there. So they hired me as an idiot 12-year-old to fold laundry and stock shelves for them. And I was sure I was terrible at it, but I did that. That was like my Sunday.
Saturdays was hockey Fridays and Thursdays was the paper route. And yeah, I just kept going from there.
John Corcoran: 03:44
My kids play baseball and soccer. And there’s a sign at the baseball field about the parents to remind them not to yell at the referees because the referees are kids and they’re like, you know, making like, whatever, 15 bucks an hour or something like that. So. Is the reason you got good at sales because you were refereeing hockey games, getting yelled at by parents?
Collin Stewart: 04:07
I don’t know if it was the reason I got good, but it certainly helped build confidence. Like there was one really lippy coach in the league and I made him out to be a real asshole. One game and I made him get out on the ice and take a knee and sit and like, take a knee next to me on the ice. Oh, really? Marty, I can kick you out.
Or you can take a knee with me on the ice. Come step down to my level. And he got down on his knee and we’re like, knee to knee and had a chat and. Yeah. And send him back on the bench.
It was amazing. A weird thing for a 13 year old to be able to command an adult.
John Corcoran: 04:43
Yeah it is. If I hope your parents took a picture of that, that would be an awesome picture for you to have.
Collin Stewart: 04:47
Now I’m old enough that, yeah, there were cameras, but they were like film cameras.
John Corcoran: 04:53
Yeah, it was like. It was like, we’re not wasting a frame on that.
Collin Stewart: 04:56
That’s going to cost me like $12 to get developed.
John Corcoran: 04:59
Developed?
Collin Stewart: 04:59
Yeah. Also, like, I was refereeing hockey. I saw like I was out there playing, so I totally I yeah, it wouldn’t be surprised if my parents were, like not paying attention at all.
John Corcoran: 05:10
But it is funny though. It wouldn’t be funny though. You look back on your childhood and you mentioned that moment in time as being impactful, like having an impact to this day on your career development and your confidence.
Collin Stewart: 05:25
Yeah. For sure. Yeah, I think I still have the record for tossing out the most fans in a, in a, in a particular rink because I basically tossed I went from here to here, you all can leave. And then I went and ran the clock until they left. So like, I ran the game clock.
Oh, like a kids game is going to be over. I went and sat in the box like, I’m getting paid. Either way, you all need to leave. Or like, I’m still going to get my 20 bucks.
John Corcoran: 05:48
Well, that answers my question. I was going to be like, how like, how do you throw out? Fans are like, we’re not leaving, but you just ran down the clock and said, like, until you just.
Collin Stewart: 05:55
Go push the button. Oh that’s.
John Corcoran: 05:57
Funny.
Collin Stewart: 05:58
That’s funny.
John Corcoran: 05:59
Well, that’ll give you some confidence for sure. So you started companies even when you’re young. So tell me a little bit about Voltage CRM. Where did that come about?
Collin Stewart: 06:10
I spent ten years as a salesperson, and I was always into computers. My grandfather was into computers. Like I remember he would always have a stack of computer magazines at his house, and I would always take them home and be reading about, like when AMD launched Athlon. And I could tell you like the CPU architecture and like why it was different from the Pentium one, Pentium was different from the 386. All that information is totally lost now in my brain.
Anyway, I’m sure it’s out there on the internet, but I was just really into computers and as the geeky sales guy that is into computers, I was always pulled into the CRM projects. And so after ten years of being pulled into CRM projects, I figured, you know what? I can do it better than these Muppets down in San Francisco. Uncle Mark’s got nothing on me. And so I decided I’m going to start a CRM company, and I’m going to take over Salesforce, which, as you can probably guess or already know, was an absolute dogshit idea.
John Corcoran: 07:05
And the tallest building in San Francisco is now the Salesforce Tower. Yeah, I’m doing okay.
Collin Stewart: 07:11
Yeah, 100%.
John Corcoran: 07:12
But the interesting thing, I mean, there has been a proliferation of a lot of different CRM. So Salesforce is a big one. I actually interviewed the inventor of the first CRM, which was like back in the early 90s, late 80s, something like that. They started it. And so there have been more CRM that have developed in different niches.
So tell me about you. What were some of the challenges in growing that?
Collin Stewart: 07:39
I mean, everything, everything was a challenge in growing that because I didn’t do any customer development for that. And let me reframe, because I did do a ton of customer development. I think I must have interviewed 150 sales leaders and asked them questions, but I was stuck on validating your idea, right? I read the Lean Startup and it said it validates your idea. And I went, okay, cool.
John Corcoran: 08:04
Got the book right behind me here. Yeah, actually. Exactly. Came to speak to our EO chapter. And it’s coming again in a month, which is really cool.
Eric Reese. Nice.
Collin Stewart: 08:13
Yeah, yeah. That’s great. And so I read that and I went, cool. I gotta validate my idea, which means I’m going to go ask people until I find the folks that tell me I’m right, as opposed to going and asking them questions to see what their pains are, to see what problems of theirs I could solve. Because I, I, I was thinking, I’m from CRM, I know exactly what I’m doing.
I know what the right thing is. I did have a valuable and accurate insight about CRM, which was when it went from something you installed on your computer into the cloud. It ceased to become. It ceased being a sales tool for salespeople. It was now a sales management tool and we still called it CRM.
But it was a totally different beast. It’s not something that’s geared for my personal productivity, like word was or outlook was. This is something for my manager to get the reports and dashboards, which are arguably extremely important. But me as a salesperson, this is a net loss for me because.
John Corcoran: 09:11
Salespeople don’t want to update the files and stuff like that. Of course, now it’s gotten easier. There’s a totally different ball game now with Fathom and Recordings and things like that.
Collin Stewart: 09:21
Yes. Yeah, there’s a lot less there’s a little bit more admin overhead of like, you got to make sure the prompts are right and make sure the things are going in the right spot and make sure you trust the information that they’re putting in. So there’s still overhead. But yes, it’s significantly easier than sending an email to a new prospect in 2012 took 27 clicks and like eight page refreshes.
John Corcoran: 09:44
Wow. Wow.
Collin Stewart: 09:45
And that’s Internet Explorer. Like 5 or 6. Something like.
John Corcoran: 09:48
That. So it took forever.
Collin Stewart: 09:49
Slow as hell. Yeah, I think I timed it once and it was like three minutes.
John Corcoran: 09:53
And were you able. Is that what you focused on? Was making that part faster?
Collin Stewart: 09:57
Yeah. I mean, not initially. The initial idea was like, I’m going to build a CRM that’s optimized for that. But it’s going to be a whole CRM, you know. And we spent a year and a half trying to sell the CRM that was a replacement for Salesforce, but it’s going to be more optimized for salespeople productivity.
And we had a lot of people. We had a lot of kicks in the can. A lot of people said it was interesting. But 80% of folks said, make it work with Salesforce or we’re not.
John Corcoran: 10:26
Working with Salesforce. Interesting. So they weren’t looking for it to replace Salesforce, which is what you thought it would be.