How I Quit Being a Restaurant Server To Become a 6 Figure SaaS Content Marketer

Michael Keenan is a SaaS Content Marketer and SEO who has worked with leading brands like Shopify, Descript, HelpScout, Fiverr, Segment, Aura, and WorkRamp.

He helps them get new users from Google and turn them into paid accounts.

Mike is also the co-founder of the Peak Freelance community for freelance writers and cohosts freelance bitters with Ashley Cummings.

But Mike didn’t start there. At age 12, he began working in restaurants as a waiter, bartender, and cook. Later on, he worked as a customer support before getting into freelancing.

This is the career story of Michael Keenan—it’s inspiring and exciting.


Subscribe: Spotify | Apple Podcasts | YouTube | Castro | iHeartRadio

What drew you to marketing, and how did your journey as a SaaS content marketer begin?

I grew up in restaurants. My mom worked in a restaurant – we had a lot of restaurant workers in the family. So, my mom got me into working in restaurants when I was about 12. As the years went by, I managed restaurants in big cities throughout the US, worked as a bartender, and cleaned gunks off the floor with toothbrushes. 

After a while, around when I was 22/23 years old, I got tired of working in restaurants and was ready for a change. I was living in Portland with some friends at the time.

Back then, Portland had many digital nomads and freelancers hanging out in cafes and bars to work online. I was interested in that lifestyle and asked a friend, “What do you do? How can I get into it?” 

He said, “Think about your skills, what you’re good at, and what you’ve done in the past.”

So, I leaned into the things I was already good at—relationships and treating customers the right way—all of the things I’d learned in restaurants—and started working in customer support. But that lasted for a short time.

Later on, I decided to try out Upwork. Sadly, the platform is not the same as it was back then. It was right when it was still named E-lance.

Long story short, I started writing articles about things I was more familiar with, like yoga and the benefits of water, and was paid $25 per article. I don’t know where these articles went, but somebody deposited money into my account after I wrote them.

When E-lance (which became Upwork) took 20%, I was left with beer money. 

That’s how it started and what got me into marketing. Then, I learned more about SEO and content management operations, leading me to where I am today: content marketing.

Presently, I have my freelance business and a separate agency.

The freelance business does smaller projects and consultations, while the agency does bigger projects, working with ten to twelve contractors per project. It’s a small agency and takes only two to three clients at a time because that’s how I want it: I don’t want a mega agency. 

Did you take any courses to teach yourself how to write?

Not for writing! That’s where my degree comes into play; I used to write research papers in college and worked in a research lab where I wrote for the professors.

Later on, I learned SEO writing while working for a luxury brand client. Then, I took the Ahrefs blogging course; it’s like an amalgamation of everything SEO. I also remember signing up for another course but never taking it.

I believe practical experience is the best course you can do. 

But if anyone is interested in learning, Ahrefs has a fantastic blog where you can learn SEO outside of a standard course, and I learned a lot from them.

How would you describe SaaS content marketing in simple words?

I get this question a lot at family dinners, and I say that I help software brands get found on Google because everyone has used the search engine before. That’s another way of saying that I help software brands get found on Google, and I do it by writing articles. 

Then, I use a basic example they most likely search for, like, “How to water your outdoor plants?” I explain further that when you search for that on Google, the first article you see is what I try to achieve for brands.

For marketers, it’s easy to understand the different jargon in the marketing world, but ultimately, we help brands get found on Google. Their goal is up to them, whether it’s free or paid users. 

What are common misconceptions you’ve heard about SaaS content marketing?

One misconception is that I do nothing. Now that everyone is familiar with ChatGPT, it gets interesting; they believe that I make ChatGPT write all the articles for me. Anyone who works in our industry would know that it’s impossible.

Ironically, I’ve had people in my life send me links to articles I’ve written because they searched for something online, and it came up. 

They were surprised to see my name and reached out to me. They were like, “Oh, this is what you do?” I said, “Yeah, there you go. That’s an example of what I do.” 

So, the biggest misconception is that I do nothing, sit down every morning with my phone and coffee, write 1000 words, and make $1,000. We all know that’s untrue.

On a smaller scale, many people think I do landing pages. For example, I have friends who are in the manufacturing industry, and they are “familiar-ish” with SEO. Sometimes, it gets slightly confusing when people think I offer copywriting services.

I don’t do copywriting, but I can offer clients landing page optimization if needed because, at the end of the day, it helps improve my content marketing results. 

How do you create relevant content that ranks consistently? 

Mike Keenan, SaaS content marketer - When writing an article, answer the people's questions first: what's the most crucial information someone needs when searching for a query?

That’s a good question. Semrush recently released a new study about what it takes to rank content, and the process is similar to the one I use to create content. A lot of it revolves around content relevance.

Content relevance means creating content specifically for the query, not a “long-ass” guide for every search query you’re targeting.

Another part is having the right people write your content. Ensure that the people writing the content have some firsthand experience. We’re seeing that more since Google is pushing the guidelines for content. 

So, when I’m outlining content, the first thing I’m thinking is, “For this query, what’s the answer they need first besides the SEO stuff? 

Answer the people’s questions first: what’s the most crucial information someone needs when searching for a query?

If it’s an article on how to mix audio with video, the first thing you’re putting in that article is the steps to get it done or a video showing the steps.

Then, if you find other things in your research related to the query, like, “What are the benefits of doing that? Or what are some examples of doing that?” That needs to go into the article because those are the questions people have related to it. So, we want to take those types of questions and write about them.

There are other tools, like Ubersuggest and Answer The Public, to find what people are searching for besides pulling directly from Google. 

Don’t just go to the first-ranking article and rip the outline. Look for areas of improvement. Think about the new information and product content missing from the top articles but relevant to the search query.

Finally, I pop the article through Clearscope. 

The Clearscope report is the final step after we’ve entered the product content and completed the outline. It is like the icing on the cake.

How do you create content that converts to leads and sales?

I’d say the traffic part is the standard, and my advice is to make sure you’re writing relevant content for the search query. 

What I do and what people consult me for (because this is also what I talk about when I’m on a sales call with a software brand) is that, within the agency, we have an entire QA layer of the content production process dedicated to incorporating product content into articles. 

You can’t expect a writer to know everything about a brand, and you don’t expect twelve to fifteen freelancers working on a product to know every single product detail. 

So, what I’ve done in the agency side of things and as a freelancer is make sure that I go through the help document for the client and that their product is well represented in the articles—not in a showboat, look-at-what-we-can-do way, but in a standard integration that flows with the article’s story.

Sometimes, we pop in screenshots, and if they have a YouTube channel, we plug in a YouTube video that makes sense. 

That’s the secret sauce because it’s also two-sided. 

The reader can see exactly how the product is used to help solve their problem, and the client loves it because you’re showcasing their brand. Brands want to rank and ensure the blog represents them well to their audience.

Even when doing strategy, I look for keywords that allow me to incorporate different product elements—screenshots, videos, and so on.

In summary, the first step in the secret recipe is to focus on driving traffic. Then, you can optimize the article to add the products—things about the product, and, in turn, convert into buying the product and becoming paying customers.

Meanwhile, the direct blog-to-pay process isn’t always easy, but you can get many free trials. We also work on down-funnel content, but I wouldn’t say direct traffic to a top-funnel keyword. 

Then, the brand should also have lower funnel content available to feed to the audience in their free trial, email newsletters, and app homepage, where they can push relevant content to them.

How did you go from sending out 20 to 30 cold pitches daily to making 6 figures?

The real turning point was when I learned SEO; that was how I transitioned out of hitting job boards all the time and pitching the Upwork connections. I could show results from the work I was doing instead of shipping out articles to random companies like I previously mentioned. 

I credit Jessica Greene, who’s the director at TestBox. She taught me how to refresh content, and that was how I started working with more prominent brands because I now had a niche specialty.

Then, the excellent writing and the refreshing process combined to create the workflow that I have now. 

Interestingly, I worked with some of those brands through people who recommended me. It all started right around COVID-19 when people started refreshing content a lot more because so many people were cranking out new content, everything was getting saturated, and everyone realized it was much cheaper and more effective to refresh. 

So, it was a mix of catching that wave and being more public about it, as well as nailing down a specialty.

However, that’s not every writer or marketer’s story. Some people are good writers, while some people are good investigative journalists. Everyone has a very particular thing they’re good at, and that’s how they get in with some of these bigger names, like Forbes and Independent. 

An example is Kaleigh Moore, who does content operations but is also very good at investigative journalism about e-commerce and fashion trends. 

In summary, a major part of transitioning for me was getting myself known about something and then letting people talk for me. 

It was a constant building process. In addition, I’m naturally curious and in search of the next thing out there. I’m really like a 100% person. I go all the way or don’t do it at all.

I also like what I do. Obviously, there are some days when everything is boring, but if you like what you do, it helps.

If you were to do it all over, would you still be a content marketer, or would you get a van and go camp somewhere, like the Wenatchee River?

I did both of them at the same time. So, if I had to do it all over again, I would probably do it the same way that I already said I did it. I’m grateful for the path that was laid out for me. 

I wouldn’t change it at all because, at this point, I love my life, my work, and what content has given me and enabled me to do in this life so far. So, if I had to go back and do it all over again, I would probably follow it step by step until this moment where I’m sitting here chatting on the Marketing Over Wine podcast.

How do you set your rates and when should you increase your rate?

For me, I have an end-of-the-year income goal. If I wanted to make $95,000 pre-tax or post-tax, I would break that out into a monthly scale. Then, I will break it further into the working hours of the month and how long it takes to write an article. 

Let’s look at it on a smaller timescale: if it takes 6 hours to write an article and you want to make $1800 per week. 

You can do that by charging $600 for an article and writing 3 articles. That’s 18 hours of work, and you can make $1800 a week. 

Calculating rates and setting pricing has always been difficult for me, but I always ask myself, “What’s my hourly rate?” It’s not what I quote forward because I do per article rate. But it’s based on “How much money do I want to make in an hour?”

“Do I want to make $100 an hour? $150, $200, $300, or $350? And what work can I fit into those hours to make the hourly rate I want to make?

Based on the previous example, if you want to make $1,800 a week and it takes you 6 hours to write an article, that’s $100 an hour if you work 18 hours per week. That’s very achievable, and that’s good money.

So, I have an end end-of-the-year goal that I want to hit, and then I work backward from there—yearly, monthly, weekly, day, and hourly.

I don’t have the correct answer for the second part—the right time to increase your rates—but in the beginning, I increased my rates for every new client I got, and I never priced the same for each new client. 

Every time I got a new client, I increased the rate, even if it was a $25, $50, or $100 increase per article, 

However, there is a price ceiling, and it’s very different for everybody. Some people make $1,000 per article, others make $2,000 per article, but everyone has a ceiling. There will be a point where you can’t increase your rates anymore because you have priced yourself out of the market.

So, keep increasing the price until someone says no. Then ask yourself, “Why? What can I do to show how much I am worth?” Maybe you can learn SEO and how to write product content, case studies, etc. 

The best thing about freelance writing and marketing in general is that you can create any path you want to take. There’s no one to limit you besides yourself. You can keep moving into different sectors and create this beautiful scheme for yourself.

What’s the least and highest amount you have been paid as a SaaS content marketer?

The least I was paid for an article was $25, which was back in the day. Then, the most I’ve been paid was a dollar and 10 cents per word, and given that the standard article was 2000 or 2500 words, that rounded up nicely.

I’m not too fond of the pricing per word method, but I have tried it. Now, I don’t have those clients anymore. The issue with pricing per word is that it’s very hard for clients to budget. 

The clients I’ve retained over the years are the ones that pay a fixed amount. They know they are getting an article, and I know I’m getting paid a particular amount. We are both happy and satisfied at the end of the day.

How do you get clients to work with as a SaaS content marketer?

Firstly, the people who come to me from stuff they read online are always the worst leads, and they never have enough money or a strategy. 

In the beginning, I had a mentor specializing in UX design, but he never promoted his brand and kept his circle very small. I did that for a while after getting off Upwork. Later on, I thought I needed to be everywhere—in the public eye—and I hated it. It was also not working, so I went back to being quiet. 

My client relationships are very good. I bend backward and constantly bother them on Slack with “Tell me what I need to do to improve. How else can we support the brand? What else do you need from me?” I will do anything! 

That type of mentality stems from my restaurant experience, where the customer is always right, and I will do anything for them.

Every client I have currently is from referrals. In recent years, I’ve not gotten one good client that wasn’t through someone telling someone about me. 

I know posting on LinkedIn works for some people, but I don’t have the desire or energy to create LinkedIn, Twitter, Instagram, and blog content.

I spend all my day in front of a computer, and I don’t want to spend more time in front of it. Once the computer is off, I am done. I have no interest in creating social media content. 

So, my client acquisition comes from referrals and good client relationships. As I said, many of my clients have been with me for years, and I don’t lose them.

How do you build a content operations framework?

My content operations involve freelancers, and I like to start with a good brief.

When I’m running the agency side of things and working with freelancers, I don’t put too much on the freelancers. That could be because I am also a freelancer.

Previously, when I worked with a company, they had an onboarding call. There were four different platforms to sign up for. There was another thing you had to do, and then you had to talk to the finance team. They later shut down the operation three months later, and it was such a waste of time.

So, if you want to work with good freelancers, it’s by not overwhelming them. 

I keep everything in Google Tables. It’s where everyone sees everything. My onboarding email is a document that describes the client and project. 

Outside of that, it’s keeping things pretty simple. We give the writers ten days to write a first draft, while editors have three days to turn around the editing draft so you can produce a good article within two weeks. I think that’s a reasonable frame to put out good content, especially at the scale where you’re working on multiple articles at once. 

I think the most significant bottleneck that we see happens in the editing. They think the freelancer isn’t that good, but they never give all the information needed to write on behalf of the brand. 

You can’t expect a freelancer to know everything about a brand. 

One way we solve these challenges is by having a QA layer. I do this at an agency scale, but you can do this much more easily in-house. 

You hire one person to QA every article after editing, and that person makes sure the article is fantastic. They can add product content or a video if it’s needed, and that has sped up everything.

We recently posted about it on LinkedIn. At the end of December, the agency put out 50 articles in about 20 days because we had a big client expectation to meet. Then, we did 90 articles over six weeks, and that QA layer was massive. 

Also, I spend a ton of money on good writers. You can’t expect to have a good content operation if you’re not working with good writers. The editors are also well-versed in the brand. Then, that QA layer speeds everything up. 

By the time it comes to the end—when it’s time to ship—the articles are clean. We never get edits back from a client because we hire good writers, excellent editors, and a QA person.

The QA person is the key. They work on behalf of the client for the agency. They’re not a client, but the goal is to pretend they’re the client if they’re reading us. They answer if an article is good enough to be on the client’s blog. If yes, get it out there. If not, they add what it needs, and we get it moving.

Generally, everyone complicates content operations, and they’re not complicated at all. To reiterate, you need good writers, a good editor to be real with the writers, a QA person, and a content manager to get involved.

What books would you recommend for marketers to read?

I would recommend “Company of One” by Paul Jarvis. You may have heard of it—many people have heard of it. Paul is a great guy and really smart. 

There’s also “Content Design” by Sarah Richards, a good book related to content. Then there is “How to Make Sense of Any Mess” by Abby Covert. 

These books aren’t related to marketing, but they help you make sense of a mess, no matter what type or industry you’re in.

It’s like a framework for examining things, which helped me put together a more simplified operation. Every operation I had been part of was so absurd that I thought, “Why are we making things so difficult?” 

Again, there are lots of factors that go into it. If you’re producing 300 articles a month, that is a lot of content. I’m not referring to those people. I’m talking about people who produce 16 articles a month, and it takes them forever. What are you guys doing? You’re wasting so much money and time.

So, “How to Make Sense of Any Mess” is a really good book to help simplify your work and life. I also recommend “Writing for Humans and Robots: The New Rules of Content Style” by Maddy Osman.

She provides specific examples from her years of running her agency, making this a really great book. I also recommend reading fiction books because they teach you how to tell a story. 

How do you choose the right hire for your marketing agency? 

I’m privileged enough to have the Peak Freelance community. There are many writers I already know who are suitable for a project, and I understand that’s not the case for everybody, but I would go into Peak Freelance as a content manager or strategist if you want to hire writers.

You could put a call out to look for people with experience writing about the topics that you’re writing about. 

Working with writers with experience in the topics you’re writing about obviously helps. It allows you to produce content from a unique perspective versus someone ripping from page one.

Although, we are currently at the client’s peak for the agency. So, we’d have to lose a client to gain a client to hire writers then, but if someone drops off, we’d be willing to hire new writers.

We have a client maximum because I’ve been too lazy and don’t care enough to grow a big agency.

What have been your career’s biggest challenges, and how did you overcome them?

The biggest challenge for me was creating peak freelance. 

A little backstory: Elise created Peak Freelance and brought me on early enough that I could call myself a co-founder. She created the Patreon group in October and then asked me to expand the brand with her in November. So, she granted me the privilege of being a cofounder with her.

That was the biggest challenge of my career thus far because it forced me to come out of my shell and be more public. I’m still not too fond of it.

I used to view freelancing as being solo and not wanting people around me because that was my perspective when I first started. Coming out of my shell and growing Peak Freelance as a community was a mental challenge. Now, I can’t imagine working without having the people I met in Peak Freelance in my life, especially what it has brought us.

So, the challenge was creating content that would be more publicly viewed and represent a brand. That was weird.

What’s your best advice for aspiring and new marketing professionals?

I will say, “do things on your own, even if you’re working in-house.”

Build a separate blog, brand, and whatever platform you want. Create your brand because that company may not be yours forever. You can get laid off, or at some point, you don’t want to work for a company anymore. 

If you already have a repertoire of things that represent you and can show that you’re a good writer or marketer, you will be in a much better position when you pitch or if someone finds you online. 

I tweeted sometime in 2021 complaining that I wanted to get pricing for a product, and the only way I could do that was to schedule a meeting with the people, and I loathed that. I tweeted about it, and my new clients referenced it in our email communications.

When people want to work with you, they search for you online—whether you think they do or not, whether they show you or not.

Everything you put out represents you, and my tip is to start building something for yourself, whether you’re a freelancer or in-house.

What tools do you use daily to simplify your SaaS content marketer work?

  • I use the Notes app on my Apple computer every single day. 
  • I use Trello for freelance stuff. 
  • I use Google Tables for the agency calendars. 
  • I use Freshbooks for freelancing and Quickbooks for the agency’s accounting software. 
  • I also use Semrush. 
  • Then, I use Google Workspace, Google Analytics, and Search Console.

What is your favorite type of wine?

I love Sauvignon Blanc. I love dry and crisp wines from New Zealand. I’m not a wine snob, and I don’t know all these things, but I’m pretty sure they come from New Zealand.

Where can we find you on social media?

You can find me on Twitter as @upmostmike and LinkedIn as mike keenan

You can join Peak Freelance on Slack. You can also figure out who I am on Reddit.

If you liked reading Mike’s career story, you will enjoy reading these ones::