SaaStr founder and CEO Jason Lemkin joins Dave Gerhardt on the Exit Five podcast to talk about all things marketing in SaaS:

  • How sales and marketing had changed since 2020
  • What motivates people to keep going
  • Solopreneurship
  • Jason’s content creation process
  • What makes a great VP of Marketing
  • Questions every marketer and founder should ask in interviews
  • Should the CMO report to the CRO

And much more! You can listen to the full podcast here.

#1: How Sales and Marketing Have Shifted Since 2020

Expectations and the types of people working in SaaS have shifted over the past few years, and much more in sales, marketing, and customer success. Jason recently interviewed a SaaStr superfan, and about 40 minutes in, the person said they didn’t want to do some of the work required for the job.

Why? They were looking to do at least 4-5 jobs at the same time now. While different than ‘typical’ interviews Jason notes as leaders, we all need to recalibrate what we expect out of people.

There are so many vibes out there, one of which is, “I quit. I’m out of here.” A senior engineer posted on LinkedIn that they worked at Spotify for four years and quit on the spot. Now, they can’t find a job.

So, how do we recalibrate in this world where we need to get shit done, but people don’t want to do the work? Folks are either burnt out or came in during the boom, and they don’t know what the real world of SaaS looked like before.

The problem for founders and CEOs is you have to do more with less. There’s no choice. “I’ve had a lot of good learnings over the years, but I don’t know the answer to this one,” Jason says.

He had a friend help him hire an email marketer to send ticket emails to the events. It’s a good job, and Jason could pay an insane amount for it, but he can’t find anyone who wants to do the work. His friend has a great group of folks that follow him, and about 40 responded to the job. He asked each of them to do one tiny bit of follow-up, and none of them did.

You have to hire the pirates and romantics, the quirky folks passionate about what they do. But tech got so big in the run-up to 2019, and beyond that, they’re just job workers, not pirates and romantics.

#2: What Keeps Someone Motivated In The Startup World

Jason has been successful, has had exits, has invested in great companies, and has built SaaStr into what it is, so what motivates him and other founders to keep going?

“It changes over time,” Jason shares. In the early days, back when SaaStr was just a blog and an email, it was a sense of creating meaning and contributing to the world. Up until 2020, the wave of passion for events and content was so strong that all he could do was ride the wave with no strategy. It was all organic.

Then 2020 hit and forced a reset. Jason asked Aaron Levie, CEO of Box, why he still does it after almost two decades while a lot of people are quietly retiring this year.

“At scale, this is a jigsaw puzzle,” he said. You’ve got a billion in revenue per year at Box, and yes, some of it goes to hosting and storage. But this is software. We have 80% gross margins. Out of that billion, Aaron gets to play with $800M. It’s intellectually stimulating and frustrating, which drives many founders.

When 2020 hit, the woe-is-me moment hit, too. “Why am I selling insurance software while my neighbor saves lives at the ER? The world is crumbling, and I’m here peddling software.”

Dave says he thought he would live in the woods and write poetry forever. He beat the drum of solopreneurship and solo content creation until about a year or two ago when he saw something there with Exit Five.

Now, he’s the most excited he’s ever been. The purpose now is that it’s fun to build something, even if you’re not saving the world.

“Builders gotta build,” Jason says. There are founders in it for nothing else but to make money, but most folks who can get something off the ground to 7 figures in revenue are builders.

#3: Solopreneurship Has a Toxic Element To It

Solopreneurship is less alluring today, and it has a heavy toxic element. “I can leave my horrible sales job making $240k OTE and be a solopreneur. On this guy’s newsletter, he says he’s up to $6M a year doing it.” Sure, one or two people make it, but if you think you’re going to be a solopreneur and are not sure if you should leave your current job, maybe find joy in the journey you’re on.

Before you become a solopreneur or sell courses, pause, meet with a few friends, and see if you can find joy within 90 days in your job. Businesses have to make money. It’s not kindergarten, where it’s always fun.

Almost everyone has a 6-figure job in tech, with an average fully-burdened cost of $250k. You might not be taking that home, but that’s what you cost. Where does that money come from? Working hard. Take a vacation, come back, and find the joy. If it doesn’t exist, move on.

#4: Jason’s Content Creation Process

Lots of marketers want to know how Jason does it. He is a prolific content creator, so let’s peek inside his process.

For SaaStr posts, content is still as pertinent today as it was 7-8 years ago. How does it stay relevant? Jason has a Google Doc full of 200 articles he fully updates, not just reposting. Take out the dated stuff and share it again.

One of Jason’s superpowers is writing content in his head automatically. Many folks who generate content aren’t writers. They may be copywriters or content marketers, but they’re not writers. That means Jason can write what he wants to say in five minutes because it’s already written in his brain.

His other superpower is taking all this knowledge, distilling and simplifying it, and making it actionable. He may not be a better writer than everyone, but not everyone can write like he does “365 days a week.”

For LinkedIn, he has morning posts scheduled through 2025. Then, while he has his morning coffee, he types up something to share in the afternoon that’s on his mind.

The actionable advice here? As a marketer, do the easiest thing. If you enjoy doing podcasts, do them. If you love to write about AI chatbots, then write for Drift. Whatever it is, if you truly love the engagement you get on LinkedIn, figure out how to do it programmatically.

But pick one type of thing you’re good at, figure out how to get the best distribution you can, and do better every month. Passions are the way to go in content marketing.

#5: What Does a Great VP of Marketing Do and What Do They Look Like

Nuances aside, the former hasn’t changed. The latter has. What does a VP of Marketing do? Unless you’re in B2C or self-serve, a B2B marker has always done the same thing: put stuff in the funnel and help move it down. The tools have evolved, and viral loops have changed, but the basic tool kit remains the same. Outbound drip marketing, content marketing, webinars, events. It all still works.

Jason thought events were archaic until he had a moment after lockdown to reflect on why they exist for marketers. He realized that until 2020, he’d never talked to one of SaaStr’s 200 sponsors. “It’s an F,” Jason jokes.

The problem today is that everyone needs a team. You might interview a marketing manager with 18 months of experience, and the first thing on their LinkedIn is “strategist.” Even if you raise a little seed capital as a founder and have a couple of million dollars, you still don’t have the budget for five marketers.

So many people take a startup marketing role and aren’t willing to do the work: host a webinar, run campaigns in Hubspot, and build a list. The marketers all want a team today.

All of that is fine if your marketing budget is north of $10M. Not ARR or capital raised, but marketing budget. If you deploy $10M of marketing spend, it better be done right. You need brand, field, demand gen, all the pieces, and a senior person. If $2M is humans and $8M is direct spend, so be it.

For everyone, whether your marketing budget is $10 or $10M, your job is to generate as much pipeline as you can. If you’re below a $10M budget, you’ll have to do work you don’t want to do.

#6: 0% of Founders Are Asking The Right Questions

The most crucial hiring point for CEOs and VPs of Marketing is asking the right questions, and 0% of founders do. It’s a simple question for founders: what are the top 3 things you’d like to do?

It might be a website, brand, messaging, podcasts, blogs, or paid marketing. As a marketer, you ask the same thing. What are the top 3 things you’re looking for in marketing? Sometimes, a deeply technical product founder with product market fit might not be interested in marketing, but they have a vision to get to developers.

Because the CEO is the CMO, you have to determine their top three priorities and see if you align. They might not say it in marketing speak, so you’ll have to ask questions. If you don’t align, stand up and say, “It’s not me,” no matter how much you need or want the job.

The worst thing that happens with executive recruiting is a mismatch. When you have a great executive and a great CEO, and it’s a mismatch, that’s the worst outcome.

#7: Having the CMO Report to the CRO is a Terrible Idea

Having marketing under a CRO is an awful idea for two reasons.

  1. Almost no CRO knows what marketers do. 
  2. You spend even more money. 

If you have marketing report to the CRO, there’s a certain efficiency when you have the same goals and KPIs. It can also be more fun because everyone is on the same team. But it removes friction, and friction is good between sales and marketing.

The CRO still has to hit their sales number at the end of the month, so if you pull in marketing, those people will focus on short-term stuff and deploying capital rapidly. There are no checks and balances there.

It’s the same problem with rolling customer success up into the CRO. Who’s going to care about customer happiness? There are no controls anymore.

Another factor is the best sellers want to close. They don’t want to help the customer one day afterward or market to them. They want to take a lead in with a 10% chance of closing and close it. Anything else corrupts the value of the best sellers.

Key Takeaways:

  • As leaders, we need to recalibrate what we expect out of people. We have to hire the pirates and romantics, the quirky folks passionate about what they do
  • Figure out motivates people to keep going and stick to it
  • Solopreneurship isn’t for everyone. Take advantage of your PTO. See if you can find joy within 90 days in your job.
  • When it comes to content creation, pick one type of thing you’re good at, figure out how to get the best distribution you can, and do better every month.
  • To be a great VP of Marketing, generate as much pipeline as you can. Don’t be afraid to roll up your sleeves and do the work yourself.
  • When hiring a VP of Marketing, make sure your top 3 priorities align with theirs.
  • Do not have your CMO report to your CRO

You can listen to the full podcast here.

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