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Gray MacKenzie is the CEO of ZenPilot, an agency training business that gives digital agency teams the structure they need to grow quickly and sustainably. They’ve helped over 1,600 agencies over the past 10 years. ZenPilot enables agency transformations from chaos to clarity through a combination of hands-on consulting, analysis, community, training, pre-built assets, templates, and processes. They serve to accelerate and de-risk your agency’s journey towards growth.

Gray is also the Founder of GuavaBox, a company that helps B2B tech and SaaS companies build a better growth strategy by applying a proven process to the four pillars of growth: positioning, lead generation, sales, and pricing.

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Here’s a glimpse of what you’ll learn:

  • Gray MacKenzie geeks out over productivity tools for agencies — especially ClickUp — and why he uses it
  • Essential agency tasks that ClickUp can help you achieve, including automation and efficient onboarding
  • How to create smooth onboarding experiences for your clients
  • Why and how Gray narrowed down ZenPilot to serving agencies only
  • Is your agency eligible to work with Gray and ZenPilot?
  • Your agency’s advantage over freelancer and in-house hires
  • Common mistakes agencies make
  • The benefits of using a scorecard to evaluate your agency

In this episode…

Your kickoff call can either create an efficient onboarding process or set off alarm bells in a client’s mind. One of the biggest onboarding mistakes your agency can make is mismanaging the kickoff call. How so? A common misstep is forgetting to restate expectations or misrepresenting them.

You can misrepresent expectations when your sales promise does not align with the deliverables you state during your kickoff call. Such misalignment of expectations is one of the many onboarding roadblocks. What are the other onboarding frictions, and how do you smoothen them out?

Listen to this episode of the Inspired Insider Podcast with Dr. Jeremy Weisz featuring Gray MacKenzie, Founder of ZenPilot. They talk about productivity tools for agencies, how to create a smooth onboarding process, and how ZenPilot is helping agencies grow. Stay tuned to catch all the insights.

Resources Mentioned in this episode

Special Mentions: 

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Sponsor for this episode

At Rise25, we’re committed to helping you connect with your Dream 100 referral partners, clients, and strategic partners through our done-for-you podcast solution.

We’re a professional podcast production agency that makes creating a podcast effortless. Since 2009, our proven system has helped thousands of B2B businesses to build strong relationships with referral partners, clients and audience without having to do the hard work.

What do you need to start a podcast?

When you use our proven system, all you need is an idea and a voice. We handle the strategy, production, and distribution – you just need to show up and talk.

The Rise25 podcasting solution is designed to help you build a profitable podcast. This requires a specific strategy, and we’ve got that down pat. We focus on making sure you have a direct path to ROI which is the most important component. Plus our podcast production company takes any of the heavy lifting of production and distribution off of your plate.

We make distribution easy

We’ll distribute each episode across more than 11 unique channels including iTunes, Spotify, and Google Podcasts. We’ll also create copy for each episode and promote your show across social media.

Cofounders Dr. Jeremy Weisz and John Corcoran credit podcasting as the best thing they have ever done for their businesses. Podcasting connected them with the founders/CEOs of P90xAtariEinstein BagelsMattelRx Bars, YPO, EO, Lending Tree, Freshdesk, and many more.

The relationships you form through podcasting run deep. Jeremy and John became business partners through podcasting. They have even gone on family vacations and attended weddings of guests who have been on the podcast.

Podcast production has a lot of moving parts and is a big commitment on our end; we only want to work with people who are committed to their business and cultivating amazing relationships.

Are you considering launching a podcast to acquire partnerships, clients, and referrals? Would you like to work with a podcast agency that wants you to win?

Contact us now at support[at] or book a call at

Rise25 was co-founded by Dr. Jeremy Weisz and John Corcoran who have been podcasting and advising about podcasting since 2008.


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Episode Transcript

Jeremy Weisz 0:19

Dr. Jeremy Weisz here, Founder of where I talk with inspirational entrepreneurs and leaders. And I’m excited about today’s guest. You know, Gray, I always like to mention other episodes that people should check out. People can check out especially because we’re going to talk about agency life a little bit. And this will be kind of part of the top agency series, everyone should check out the episode with Jason Swenk. And check out what he’s doing with his podcast and his group. It’s amazing. I did an episode with Chris Martinez of the Dude Agency, also a really interesting guy in the business he’s built. Duncan Alney check out his website at Firebelly I know we that’s a mutual friend of Gray and I’s. So check out Firebelly and they have an amazing podcast as well. And Dean Dutro Worth eCommerce, you know, this is if you have an e-commerce site, and you actually want to generate an own your deploy your media whenever you want with email marketing, SMS marketing, that’s what they help people do. So check those episodes out. And before I introduce Gray, this episode is brought to you by Rise25. And, you know, Gray the way I explain what we do is you could tell me, this is a good way of explaining or not, but I say we help people connect to their dream 100 relationships in partnerships. And we do that by helping you run your podcast. So there’s an actual strategy behind it. And the strategy is giving to your relationships. Okay, like, that’s what everyone should do. The number one thing in my relationships in my life is relationships, I’m always looking in a way is how can I give to Gray and, you know, ZenPilot? How can I give to people I know in my network, and one of those ways I can give, which I found over the past 10 years, is to have them on my podcast, and then profile them and then distributed across like 20 different places. So if you’ve thought about starting a podcast, I think, even before was self serving grads, say if you have a business, you should have a podcast period. I know you guys have a podcast as well. If you have questions about it, we’re happy to answer them go to And you can email our team, you can email me personally, and we’re happy to do we’ve been doing it for over a decade now. So check that out. Today we have Gray MacKenzie, he is CEO of ZenPilot, and they give digital agencies the structure, they need to grow quickly and sustainably. And they’ve helped over 1600 agencies over the past 10 years. And he’s also the Founder of GuavaBox. And this stems You know, I think you talk about this that you and your co founder, just want to do something together. You want to work together, you want to start something and this this stems all the way back to college. So but you could go to And check out more what they’re working on. So Gray. Thanks for joining me.

Gray MacKenzie 3:00

Yeah, Jeremy, thanks for having me. I appreciate it. You mentioned relationships is the number one thing. You’re such a good connector, I was actually just talking with somebody last week who’s a 20 year old into podcast, really into podcast trying to build a podcast production agency. I was like, Man, you should just talk to Jeremy. He should see about going and working there. Just tell him upfront, I want to build my own business at some point. Go work there, figure out what it’s like if you like it or not be upfront about your intentions. And you could probably learn a lot just from being inside of them. Have you always been a connector and like just wired the way that you are? Or is that something that’s Was there some experience of default? That’s right.

Jeremy Weisz 3:38

Yeah, no, um, you don’t actually Yeah, yes. I mean, there’s people out there, I think that you find just our natural recommending of people, they they’re, they’re, you know, evangelists have things, right. And I’ve always, I feel like always been like, oh, if I see this movie, I’ll like, go out and tell like 30 people. Yeah, like, there’s no benefit to me. I’m just like, Oh, you got to check this out. So I’ve kind of naturally wired that way a bit. To just, if I like something, telling people about so that’s awesome. A service a person. And I’m probably make, you know, five to 20 introductions every single day to people ranting I do double opt in, right. So I’m asking both parties, so I’m probably sending, like 40 emails just to make the 20 connections, right? Or actually more than that,

Gray MacKenzie 4:35

more using Gmail. This is silly question. But yeah,

Jeremy Weisz 4:38

no, I use Gmail. Yeah. But um, I use one of the things I use is TextExpander. So I don’t know if you’ve used it before. It’s like $4 a month. And so I save everyone’s bio, like, I have your bio saved. And so when I want to make introduction, I just write intro Gray MacKenzie in your nice looking thing that I pre wrote comes up and I can send it off to people

Gray MacKenzie 5:00

That is really smart. You know, what, what’s your? What’s your snippet structure? Is that what you’re doing? You’re actually Yeah,

Jeremy Weisz 5:05

yeah, I put my snippet structure is if you’re geeking out on this for a second, we’ll get to that. I mean, this is part of it. You know, this is, you know, I’ve done full, I got on a call with, like, 15 of someone’s team members. And I’ve explained TextExpander like weight sharing, what do you do? I’m like, No, I don’t represent TextExpander it goes into that referral thing. But yeah, my snippet structures like, intro, first name, last name. And then I have everyone so if I introduce you once I just save your bio in text. expander so if you haven’t looked at text expander look at it because it’s a great productivity tool. I mean, some of the, you know, this kind of goes into I’m curious about the productivity tools you use. I use Sanebox LastPass, Text Expander you know, those are a few Come come to mind. I mean, obviously you love ClickUp what are some of your productivity or tools or apps that you like,