SaaS CMO Pro

Something has been bothering me recently

New AI startups using old marketing & sales playbooks

Skipping straight to the enterprise

Cold calling and cold e-mails

AI spam

Top down sales

Mindless press releases

Trying to buy off analysts

Long deal cycles

Looks and sounds like everyone else

No one knows about their startup



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Most people think promotions are all about performance—but like it or not, perception plays a role too. In this video, I dive into the surprising impact your outfit can have on your career growth as a B2B tech marketer. Does what you wear really matter? How do top marketers think about workplace dress codes? And can dressing a certain way actually help you get ahead?

I’ll share my own experiences, practical tips, and a few...

Learn how to use control groups to measure the effectiveness of your marketing efforts with precision. In this video, I’ll share practical examples from my time at Slack, Zendesk, and Salesforce, showing how control groups can help you evaluate ad campaigns, website changes, customer success initiatives, and more. Whether you’re a marketer, CEO, or VC, this simple yet powerful technique can save you money, improve decision-making, ...

Every SaaS and AI founder is forced with this question early on ... should you skip the SMB segment and go straight to the enterprise?  I dive into the pros and cons here and lay my case for what I think is the clear answer.

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🦥 SaaS CMO Pro
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Official website: https://www.saascmopro.com/

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🚀 About Bill:
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When Are You at Your Best? 🔋

I didn’t always think about my peak energy hours—but once I did, it changed everything.

Here’s what worked for me:

1️⃣ Map Your Energy:
Take note of when you feel most productive and energized during the day. For me, it’s 8–10:30 AM. That’s when I tackle big projects or creative work.

2️⃣ Plan Around It:
Align your toughest tasks with those high-energy period...

Learn how to identify and eliminate friction in your Product-Led Growth (PLG) strategy. From pricing and adoption friction to cognitive and invite friction, I’ll share actionable tips to help SaaS and AI companies grow faster and more efficiently. Perfect for founders, marketers, and product teams looking to accelerate growth. 🚀

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🦥 SaaS CMO Pro
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Offic...

Hey folks. Today, I want to share one crucial lesson I learned the hard way: never put anything in writing that you wouldn’t be comfortable with everyone at your company seeing.  Let's dive into this topic and I'll share some strategies I used to help avoid this.

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🦥 SaaS CMO Pro
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Official website: https://www.saascmopro.com/

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When I built marketing at Slack, Zendesk and Salesforce, I always had to make a fundamental decision.  Which functions should we hire internal marketers for and which should we outsource to agencies?  In this video I walk you through the pros and cons of in-house vs agency in this ultimate battle royale!

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🎥 Chapters
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0:00 Introduction to In-House vs. ...

I had the great pleasure of working with a spectacular team at Zendesk.  I joined at an early stage (about 65 people) and came on as their first CMO.  I built out the marketing team and in a couple years we took Zendesk IPO. 

We had a guiding principle at Zendesk and it could be distilled into two words: Beautifully Simple.  This video dives into how those two words manifested into practical strategy that helped propel Zen...

Spend a little time learning about In-Product Messaging (IPM) and why I'm such a huge fan of it.  IPM is an incredible way to educate and nurture your users within your SaaS or AI tool.  

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🎥 Videos mentioned 
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 https://www.youtube.com/playlist?list=PLFhqt_82AGLqM_XRLLqHqbsLHrA6rlSX_

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🦥 SaaS CMO Pro
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Great customer references are always hard to get.  I spill the beans on my top 7 strategies to get more and better customer references.  These help even if you are going after the elusive enterprise segment.  

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🎥 Videos mentioned 
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https://youtu.be/FcQ-Qxdvq_8
https://youtu.be/Ol6kMjzMOAs

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🦥 SaaS CMO Pro...

Ok you teased me Bill with that title.  I'm a PLG fan.  What the heck industry doesn't work for PLG?!?.

Listen on my friend.

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🎥 Videos mentioned 
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https://www.youtube.com/watch?v=qUZngF95dyo

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🦥 SaaS CMO Pro
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Official website: https://www.saascmopro.com...

Mistakes happen.  It's just the truth.  And at some point you or your team will make the mistake and it will get called out in a big meeting.  Here is my simple 3-step formula that my Dad taught me on how to communicate the problem.

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🦥 SaaS CMO Pro
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Official website: https://www.saascmopro.com/
Newsletter: https://saascmopro.substack.com/

Supercharge your SaaS growth!  I reveal six advanced pricing secrets I've used to help ignite your y/y ARR growth to new levels.  These are advanced strategies but can be leveraged by any SaaS and AI company.  Go get em!  Carpe diem my friends.

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⏰ Table of Contents
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0:00 - Introduction to Advanced Pricing Strategies for SaaS & AI
0:11 - Wh...

Are you a B2B SaaS Marketer?  Do you feel a bit overwhelmed?  Don't worry, you are not alone.  There are just so many internal stakeholders that all want a laundry list of things from marketing.  I share my best tips on how to handle the chaos and focus your marketing team.

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⏰ Table of Contents
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00:01 - Feeling Overwhelmed in B2B SaaS Marketing

Discover the weird truth about SaaS freemium plans as former Slack CMO, Bill Macaitis, dives into the pros, cons, and hidden benefits of this controversial pricing strategy. From transforming millions of free users into a powerful marketing force to creating an unbeatable defensive moat, learn why freemium might be the game-changer your SaaS company needs. Whether you’re struggling with brand awareness, tackling enterprise sales, o...

Want to learn a little bit more about what Product Led Growth (PLG) is?  You are in the right place.  I'm the former CMO of Slack and I've helped SaaS and AI startups with dozens of PLG implementations.  In this video, I give you my perspective on what PLG really is, why it matters, and how to implement it successfully. Learn about the key elements of PLG, including self-service, reducing friction, infusing sales, marketi...

Did you ever get a really good piece of career advice that you stowed away in your head for life? I want to hear it! Share it so everyone can learn and get a little better.

Well I got mine on my first job out of college. There was a tradition we had where we would all go out to lunch when it was someone’s last day. And I made it a habit to ask the last day person what their best piece of career advice was.

One time I got a ...

Marketing metrics demystified.

I've spent 30 years thinking about what should be the right marketing metrics that incentivize the right behavior for the team.  Here are the six categories I used at Slack, Zendesk and Salesforce for my B2B marketing teams.

1.Funnel Metrics 🔄

These are the bread and butter of every B2B SaaS marketing team. I really advocated for moving beyond just leads.

•Website visits

•Form completes

•Leads

•Marketi...