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William Macaitis

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SaaS CMO ProSaaS CMO ProHow Slack Skyrocketed: Lessons from their original CMOToday I'm diving into a question I often hear from founders: How did Slack grow so fast? What was the key factor that really made the difference?I was fortunate enough to get an inside view of Slack from the early days, joining as CMO around employee #50. During my time there, I built out the marketing team and eventually led sales, customer success, and support.In this episode, I want to share some of the most effective growth strategies we used—practical approaches that I genuinely believe contributed significantly to Slack's rapid growth. My goal is...2025-06-0744 minSaaS CMO ProSaaS CMO Pro5 Proven Ways to Beat Internal Resistance to PLG (Product Led Growth)Big believer in Product Led Growth?  In charge of implementing PLG at your company?  Well you are most likely going to encounter some stiff resistance.  Not everyone drinks the PLG juice and you may have some internal stakeholders (sales, finance, board members, c-suite) who actively try to keep the status quo and are afraid of what PLG might mean.I walk you through 5 proven strategies to identify internal resistance and smash through it.  Look, implementing a PLG initiative is a LOT easier if you build it out when you are in the early stages (seed, series A).  When...2025-04-2624 minSaaS CMO ProSaaS CMO ProAI Founders Are Making This CRITICAL Go-To-Market MistakeSomething has been bothering me recentlyNew AI startups using old marketing & sales playbooks Skipping straight to the enterpriseCold calling and cold e-mailsAI spamTop down salesMindless press releasesTrying to buy off analystsLong deal cyclesLooks and sounds like everyone elseNo one knows about their startupI’ve been trying to work with more seed AI startups to break this patternNormally I don’t get involved in s...2025-04-0604 minSaaS CMO ProSaaS CMO ProWhy Tech Marketers Lose Promotions (Your Outfit Matters)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 strategies successful professionals use to navigate office dress norms.============================ 🦥 SaaS CMO Pro=============================Official website: https...2025-02-1206 minSaaS CMO ProSaaS CMO ProThe better (and cheaper) alternative to multi-touch attribution. 🧪📊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, and provide definitive proof of ROI—all without expensive attribution tools. ============================= 🦥 SaaS CMO Pro=============================Official website: https://www.saascmopro.com/============================= 🚀 About Bill:============================= Bill Macaiti...2025-01-2907 minSaaS CMO ProSaaS CMO ProShould you skip the SMB segment?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.============================= 🦥 SaaS CMO Pro=============================Official website: https://www.saascmopro.com/============================= 🚀 About Bill:============================= Bill Macaitis is an advisor and board member guiding aspiring AI & SaaS unicorns/decacorns.  Bill works with companies to build out capital efficient go-to-market strategies and world class teams. Over his 30 year career Bill has achieve...2025-01-0811 minSaaS CMO ProSaaS CMO ProMy best productivity hacksWhen 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 periods. Save low-energy times for simpler tasks or breaks.3️⃣ Recharge Strategically:I’m a sprinter, not a marathoner. After a focused...2024-12-2704 minSaaS CMO ProSaaS CMO ProUnlocking Hyper-Growth: The Art of Removing Friction in PLGLearn 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. 🚀============================= 🦥 SaaS CMO Pro=============================Official website: https://www.saascmopro.com/============================= 🚀 About Bill:============================= Bill Macaitis is an advisor and board member guiding aspiring AI & SaaS unicorns/decacorns.  Bill works with companies to build out capital efficient go-to-market strategies and world class teams. Over his...2024-12-0614 minSaaS CMO ProSaaS CMO ProThe Golden Rule of Professional Communication ✨📜💼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.============================= 🦥 SaaS CMO Pro=============================Official website: https://www.saascmopro.com/============================= 🎥 Key items in Zoom/Youtube setup ============================= FULL 150+ item gear listing: https://www.saascmopro.com/gear============================= 🚀 About Bill:============================= Bill Macaitis is an advisor and board member guiding aspiring AI & SaaS unicorns...2024-11-2104 minSaaS CMO ProSaaS CMO ProScale Your Marketing Team: In-House 🏠 vs. Agency 🤝 GuideWhen 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!============================= 🎥 Chapters============================= 0:00 Introduction to In-House vs. Outsourcing0:46 Key Factors for In-House vs. Outsourcing in Marketing1:32 Advantages of Outsourcing for Speed2:10 Common Marketing Functions to Outsource2:52 Weighing the Costs of Outsourcing3:39 Building Core Competencies In-House4:21 Benefits of Outsourcing Creativ...2024-11-0606 minSaaS CMO ProSaaS CMO Pro🔑 Two words took Zendesk from zero to IPO 🚀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 Zendesk to huge heights.============================= 📖 Table of Contents=============================00:00 - Introduction00:20 - Background00:40 - Revealing the Key Concept...2024-10-3008 minSaaS CMO ProSaaS CMO ProThe 🔒 HIDDEN Potential of 💬 In-Product Messaging in SaaS 🚀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.  ============================= 🎥 Videos mentioned =============================  https://www.youtube.com/playlist?list=PLFhqt_82AGLqM_XRLLqHqbsLHrA6rlSX_============================= 🦥 SaaS CMO Pro============================= Official website: https://www.saascmopro.com/Newsletter: https://saascmopro.substack.com/Hire me: https://www.saascmopro.com/advisor-se...Brand partner: https://www.saascmopro.com/brand-partnerSpeaking opps: https://www.saascmopro.com/speaking-opps============================= 🎥 Key items in Zoom...2024-10-2309 minSaaS CMO ProSaaS CMO Pro7 tips for more customer references 💬🤝✨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.  ============================= 🎥 Videos mentioned ============================= https://youtu.be/FcQ-Qxdvq_8https://youtu.be/Ol6kMjzMOAs============================= 🦥 SaaS CMO Pro============================= Official website: https://www.saascmopro.com/Newsletter: https://saascmopro.substack.com/Hire me: https://www.saascmopro.com/advisor-se...Brand partner: https://www.saascmopro.com/brand-partnerSpeaking opps: https://www.saascmopro.com/speaking-opps============================= 🎥 Key items in Zoom...2024-10-1615 minSaaS CMO ProSaaS CMO ProPLG 100% ❌ Does Not Work for This Industry 🏭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.============================= 🎥 Videos mentioned ============================= https://www.youtube.com/watch?v=qUZngF95dyo============================= 🦥 SaaS CMO Pro============================= Official website: https://www.saascmopro.com/Newsletter: https://saascmopro.substack.com/Hire me: https://www.saascmopro.com/advisor-se...Brand partner: https://www.saascmopro.com/brand-partnerSpeaking opps: https://www.saascmopro.com/speaking-opps============================= 🎥 Key items in Zoom/Youtube setup ============================= FULL 150+ item gear listing: https://ww...2024-10-1005 minSaaS CMO ProSaaS CMO ProHow I handle work mistakes. The simple 3 step process 🛠️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.============================= 🦥 SaaS CMO Pro============================= Official website: https://www.saascmopro.com/Newsletter: https://saascmopro.substack.com/Hire me: https://www.saascmopro.com/advisor-se...Brand partner: https://www.saascmopro.com/brand-partnerSpeaking opps: https://www.saascmopro.com/speaking-opps============================= 🎥 Key items in Zoom/Youtube setup ============================= FULL 150+...2024-10-0303 minSaaS CMO ProSaaS CMO Pro10X Your SaaS Growth: Advanced Pricing StrategiesSupercharge 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.============================= ⏰ Table of Contents============================= 0:00 - Introduction to Advanced Pricing Strategies for SaaS & AI0:11 - Why Pricing & Packaging Matters for SaaS Growth0:40 - Common Pricing Mistakes in SaaS Companies1:26 - Who Owns Pricing in Your Organization?2:08 - Choosing the Right SaaS Pricing Models2:49 - Keeping Pricing Simple for Pros...2024-09-3030 minSaaS CMO ProSaaS CMO ProWhy B2B Marketers Feel Overwhelmed 😩 & How to fix it!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.============================= ⏰ Table of Contents============================= 00:01 - Feeling Overwhelmed in B2B SaaS Marketing00:57 - Common Challenges Faced by CMOs01:37 - Focus on Mastering a Few Channels02:41 - Building a Marketing Team with Strengths03:21 - Leveraging Video for B2B SaaS Marketin...2024-09-2308 minSaaS CMO ProSaaS CMO ProThe Weird Truth About SaaS Freemium PlansDiscover 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, or looking for capital-efficient growth, this video will uncover why freemium could be your secret weapon.============================= 🦥 SaaS CMO Pro============================= Official website: https://www.saascmopro.com/Newsletter: https://saascmopro.substac...2024-09-1829 minSaaS CMO ProSaaS CMO ProWhat the Heck is PLG? 🤔🚀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, marketing, and customer support into the product, and how to measure success using metrics like Net Promoter Score (NPS) and Product Qualified Leads (PQLs). Btw...2024-09-1234 minSaaS CMO ProSaaS CMO Pro✨ The Best Career Advice I Ever Got 🚀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 piece of ad...2024-09-0904 minSaaS CMO ProSaaS CMO Pro📊 Mastering Marketing Metrics for B2B SaaS 📊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•Marketing Qualified Leads (MQLs)•Sales Accepted Leads (SALs)•Sales Qualified Leads (SQLs)•Opportunit...2024-09-0426 minSaaS CMO ProSaaS CMO ProWhy PLG is Your Secret Weapon in Enterprise Sales 🚀In this pod, I dive into why Product-Led Growth (PLG) is a salesperson’s best friend. I’ll break down what PLG is, how it reduces friction in the sales process, and why it’s especially effective in enterprise sales. Whether you’re dealing with long deal cycles or trying to build brand awareness, PLG offers powerful tools like freemium models and internal evangelists that can help accelerate your sales efforts. Tune in to learn how PLG can transform your sales strategy.============================= 🦥 SaaS CMO Pro============================= Official website: https://www.saascmopro.com/Newsletter: https://saascmopro.su...2024-08-2713 minSaaS CMO ProSaaS CMO ProBehind Slack’s Success: 🔥 The Fair Billing Policy 🔥In this video, I dive into Slack’s Fair Billing policy and how it became a key part of our product-led growth (PLG) strategy. By offering credits for inactive users, we aligned our goals with those of our customers, ensuring that we only made money when people actively used the product. This approach not only built immense goodwill but also drove Slack’s hypergrowth. Tune in to learn why more companies should consider adopting a similar strategy.============================= 🦥 SaaS CMO Pro============================= Official website: https://www.saascmopro.com/Newsletter: https://saascmopro.substack.com/Hire me: https...2024-08-2205 minSaaS CMO ProSaaS CMO Pro😓 4 Strategies to Survive a Toxic Workplace 😓We’ve all been there at some point. You work long enough and at some point you encounter a really bad work environment. A workplace that stresses you out, drains your energy, and makes you dread coming to work each day.Toxic environments fester like a week old fish in the fridge. No one like them.Unfortunately, it’s not always as simple as leaving for another job when these situations present themselves. Maybe you love parts of your job. Maybe you are loyal to your team. Maybe you are loyal to the mission. So...2024-08-1906 minSaaS CMO ProSaaS CMO ProAvoiding PLG Landmines ❌ 7 Mistakes That Can Doom Your Strategy ❌Product-led growth (PLG) can drive incredible results, but only if you avoid these 7 common pitfalls. I break down the top reasons PLG initiatives often fail and provide strategies to ensure your success. Don’t let these challenges stand in your way—watch now to learn how to navigate the PLG landscape effectively.============================= 🦥 SaaS CMO Pro============================= Official website: https://www.saascmopro.com/Newsletter: https://saascmopro.substack.com/Hire me: https://www.saascmopro.com/advisor-servicesBrand partner: https://www.saascmopro.com/brand-partnerSpeaking opps: https://www.saascmopro.com/speaking-opps============================= 🎥 Key items in...2024-08-1517 minSaaS CMO ProSaaS CMO ProBuilding the ultimate Zoom setup 🎥💰Watch this video podcast on Youtube for more visuals of the studio itself!If you want to up-level the professionalism of your Zoom setup, then this video is for you. Have you ever had a project that got a little out of hand? That you obsessed over and wanted to make sure every detail was right? Well, that may or may not have been me. Okay, it was me. I spent about a year and a half building out the “Ultimate Zoom Setup.” To be honest, I wasn’t trying to build out the “ult...2024-08-081h 07SaaS CMO ProSaaS CMO ProTop 8 CMO interview questions (for founders & CEOs)Are you looking to hire a CMO but unsure where to start?  I share my top eight interview questions that can help you find the right fit. Whether you’re seeking a creative genius or a data-driven strategist, these questions will guide you to the best candidate for your company’s needs. #CMO #Hiring #MarketingLeadership #SaaSLearn marketing + watch full video at  🚀 Saascmopro.com 🚀 Learn marketing + watch full video at 🚀 Saascmopro.com 🚀 2024-08-0524 minSaaS CMO ProSaaS CMO Pro🚀 How to Hire the Right CMO for Your SaaS Startup! 💡🔍 Introduction to the ChallengeHey folks! Hiring the right Chief Marketing Officer (CMO) can be a daunting task for any CEO, especially in the fast-paced world of SaaS and AI startups. But fear not, because today, I’m breaking down the key lenses you need to consider to make this critical hire. From understanding your go-to-market motion to identifying whether you need a creative or a quant, I’ve got you covered. So grab your popcorn, sit back, and let’s dive into this! 🍿🚀🏢 Understanding Your Go-to-Market MotionFirst up, what kind of b...2024-08-0101 minSaaS CMO ProSaaS CMO ProCredits 💡 The SaaS Growth Hack You Aren't Using Yet 💡Cash 💵, Moolah 💰, Chedda 🧀, Benjamins 💸, Bread 🍞Who doesn’t want some? And when it is free money … ooooooh baby, now we are talking. So today, I’m going to talk about CREDITS and how to use them effectively in your SaaS company. We’ll dive into the history of credits, how we used them at Slack to grow faster, and I’ll share some practical tips on implementing them in your own SaaS or AI startup. Let’s go!💡 What Are Credits?When I mention credits, I’m not talking about accounting terms like debits and credits. I...2024-07-2904 minSaaS CMO ProSaaS CMO Pro💸 How to Build a Brand with Zero Budget 🚀I’ve been doing online tech startups my entire life (past 30 years). Sometimes I had a big marketing budget, sometimes I had zero budget. ¯\_(ツ)_/¯ But I started with zero budget. And having nothing is the mother of invention when it comes to finding creative ways to build a brand. 🌟So this post is for all those AI and SaaS startups that WANT to create a brand but just don’t have the budget for it (don’t worry, you are not alone). 💪 Watch the video for the WHY behind these strategies or read below for the summary on smart, sneaky...2024-07-2511 minSaaS CMO ProSaaS CMO ProOMG it is PLG time!! 📊 Top 5 PLG metrics! 📊I am SUPER excited because we are finally diving into PLG!!!! (Product Led Growth) This is by far one of my favorite topics to talk about and I went a little crazy here. This is the first of 26 videos on PLG. That was not a typo.Yeah. Did you know you were subscribing to a crazy growth marketer who loved PLG so much? No? Well you do now. No take backs.So buckle up. Get your PLG headphones on. We are kicking it off with my favorite 5 metrics for tracking PLG initiatives. Whether you’re a...2024-07-2221 minSaaS CMO ProSaaS CMO ProUnlocking Hidden Revenue💰 The Power of Customer Marketing in SaaS 💰Unlocking the Power of Customer Marketing in SaaS: Let’s Dive Deep! 🚀Hey folks, today I’m talking about something crucial that I see too few SaaS marketing teams focusing on: customer marketing. I’m going to break down what customer marketing is, why the metrics often work against it, and why we need to do more of it. Alright, let’s dive in.What is Customer Marketing? 🤔First off, what is customer marketing? It’s one of those terms that can mean different things to different people. For many B2B organiz...2024-07-1911 minSaaS CMO ProSaaS CMO ProBillboard Ads for Tech Companies 🚀 Brilliant Move or ❌ Big Mistake💬 Speaking as someone who was a bit skeptical about these and from someone who actually ran billboard ads, I’ll give you my 2 cents on this age-old question. 💭Also if you are a fan of SaaS CMO Pro and want to see more subscribe to our social channels:📱 Tiktok SaaS CMO Pro📸 Instagram SaaS CMO Pro🐦 X Saas CMO ProThanks and have a wonderful day! 🌟Best,BillLearn marketing + watch full video at 🚀 Saascmopro.com 🚀 2024-07-1611 minSaaS CMO ProSaaS CMO Pro🚫 Career Killers 🚫 Common Mistakes New Marketing Director Makes🚫 Avoid these common pitfalls that many new Directors of Marketing face. I've seen many new managers or directors of marketing make these mistakes, and often their careers stall or even cause them to lose their jobs.And often, these are good people. I don't want to see that happen to anyone watching a SaaS CMO Pro video! So buckle in for an important marketing career video, and hopefully, this will help you or someone else down the road. 🙏As always, I appreciate all of your support for SaaS CMO Pro! 🙌 Btw, if shorts are more your styl...2024-07-1517 minSaaS CMO ProSaaS CMO Pro🚀 3 Game-Changing Metrics SaaS CEOs Overlook: Are You? 📊🎯💡 Are you tracking the right metrics? It is always interesting when I work with different AI and SaaS founders and what metrics they choose to track and put importance on. In this video, I delve into the top 3 overlooked metrics that every SaaS & AI leader should monitor. These aren't just any metrics; they're the game-changers that can supercharge your growth and maximize capital efficiency. 🚀📊If you're a CEO, founder, or VC, these insights are crucial for fostering sustainable and capital-efficient growth. Don't miss out on the metrics that could define your success in the competitive SaaS landscape. 🌟📈Learn mar...2024-07-1416 minSaaS CMO ProSaaS CMO Pro💥 Crappy Sales Response Times to Marketing Leads 💥Excited to kick off the launch of SaaS CMO Pro with a timeless B2B topic: why sales often has crappy response times to marketing-generated leads. I discuss 🤔...🚀 My name is Bill Macaitis and I am your host for the SaaS CMO Podcast.  I am a seven time marketing leader, with 3 CMO tours of duty and five tech exits.  I'm hear to help you learn about marketing in a fun and easy to understand way.In this video, I dive deep into the classic tug-of-war between sales and marketing in B2B SaaS and AI companie...2024-07-1405 min