Why Less Is More for Content Marketer Andy Crestodina

With more than a million visitors and almost 1,000 leads per year, Andy has never published content more than twice a month. Find out how less is truly more for this content marketer.

Interview with Andy Crestodina from Orbit Media

We interviewed content marketer Andy Crestodina, co-founder and CMO of Orbit Media Studios, to better understand how he gets over a million visitors and almost 1,000 leads per year—and never publishes more than twice a month.

We also talk about the 3 biggest challenges that content marketers are facing today (and how to overcome those challenges), as well as his advice for folks just starting out in content marketing. Read his interview below.

Andy Crestodina interview

Andy Crestodina, Co-founder & CMO, Orbit Media Studios

Name: Andy Crestodina
Job title: Co-founder & CMO
Company: Orbit Media Studios
Location: Chicago, MI
Degree: BA, Asian Language & Literature (Chinese)
Author of: Content Chemistry: The Illustrated Handbook for Content Marketing

Fun facts about Andy Crestodina:

🥙 Food you’re craving right now: Falafel
☕ Tea, coffee, or something else?: Lots and lots of coffee (~6 cups per day)
👪 You’re a parent to: Eli (6) and Ada (4) …they have short first names because their last name is “Crestodina”

Can you tell us about your career journey?

Andy Crestodina: Well, Plan A was to teach Mandarin in high schools in Iowa. Instead, I decided to see what was happening in the world of business. I was an IT recruiter in the late ‘90s and quit because it wasn’t creative. I didn’t get to make anything. 

I wanted to be a designer, and it was easier to start a company than to find a job because I didn’t have a portfolio. So I joined a friend who was already building websites, and we started Orbit Media in 2001 and never looked back. 

But the full-circle story is that years later I realized I had to hone my skills as a content marketer to attract an audience and generate leads without a budget. So in a way, I became a teacher after all because so much of content marketing is about creating useful, helpful materials. There’s a learning objective, just as teachers have with lesson plans.

What are 3 of the biggest challenges content marketers face today?

1. Lack of time

The number one challenge content marketers are facing is lack of time. According to all the surveys, marketers want to spend more time with their content, but we’re all under the gun because of publishing deadlines and our calendars.

Solution? Do fewer things—and make them bigger and better

It’s more efficient to publish more detailed answers and stronger pieces with lower frequency.

A lot of people think they need a weekly article. In 15 years, my frequency has never been more than twice a month. I still have more than a million visitors, I’m generating close to a thousand leads a year, and we’re hitting all of our goals.

Be very efficient with your time and stop publishing medium-quality content. Reduce your frequency and make each piece that you publish hit harder. Success really comes from not publishing a thousand good things, but publishing a hundred really great things—and keeping them updated.

2. Buy-in

Another big challenge is buy-in. We get input from our clients or from executives who are forcing us to justify our actions on a time scale that sometimes isn’t realistic because content marketing is slow.

Or we get pushed into topics and strategies that really just don’t make sense. There are sales teams and executives who say, “Why aren’t we writing about X?” even if X was not part of our content strategy.

Solution? Document your content strategy so you can defend yourself from stakeholder requests.

Unless you have a documented content strategy, you’ll always be on the defensive when stakeholders ask for things that aren’t part of the plan.

Maintain a list of hypotheses: when someone has a new idea, you can put it on your list of hypotheses and score it against the other things that are also on that list. This way, you’re deprioritizing bad ideas wherever they come from, including yourself, and prioritizing the most impactful ideas wherever they come from, including others. 

When someone says, “Why don’t we do X?”, use data. You can say, “Well, we tried that and the results were flat.” The only way to combat a bad opinion is with good data.

3. Algorithms and big tech are in between us and our audiences

For example, if Google decides to fill search results pages with tons of visuals, it’s harder for writers to get traction as click-through rates decline. This is the biggest trend in SEO.

Also, AI is going to start answering all kinds of people’s questions. Our target audiences will rely less on clicking on a website to get an answer.

Solution? Make the algorithms irrelevant by building a community and relationships

Reach out to sales support. Create content specifically for your current leads—content that closes deals. Go to the bottom of the funnel. Algorithms matter much less down there.

What advice do you have for content marketers worried about economic uncertainty?

Andy Crestodina: The people who are best positioned to succeed in a downturn or in the face of stiff competition or a new technology like ChatGPT are the people who wrap their services in strategy and measurement. 

People don’t like to pay to have things created for them. People don’t mind paying for strategic advice, plans and the measurement of activities that were taken. For anyone who’s trying to make a living by just making something—Orbit builds websites—there’s always going to be a cheaper option. 

It’s easy for people to discontinue or pause your contract. But when your services are considered strategic, you’re far more secure in the value that you offer when the value you’re adding is something that far fewer people can do, when you’re proving results through Google Analytics or some other metric.

In the age of AI and ChatGPT, what advice would you give to someone just starting out in content marketing?

Andy Crestodina: There’s no question that ChatGPT is a fantastic research tool, and when used as such, it has huge value for the content creator, editor or researcher. But if you’re worried about it taking your job, there are lots of things you can do to be secure in your work. Do what it CAN’T do: 

  • It’s not good at writing strong opinion pieces 
  • It’s not good at empathy
  • It’s not good at hard-hitting first sentences 

ChatGPT tries to be accurate and useful in a broad way, so it frequently starts with a long, boring paragraph of throat-clearing language to qualify itself. It just tastes like water. How do you beat that? Make your content taste like whiskey. Stick your neck out. Take a stand. Make stronger assertions. Be unexpected.

People who are good at social media are probably not worried about ChatGPT. The people who are worried about it are the people who are trying to produce large volumes of medium-quality content that appeals to broad audiences.

If you were competing before with cheap overseas writers and now you’re competing with an actual robot that’s free, these are never good places to be. Be more human. Get contributor quotes from experts. ChatGPT is a tool for all of us to be more efficient in doing research, but it can’t replace a human voice.

P.S. Want more marketing insights?

If you’d like access to more content marketing insights like this, sign up for our newsletter to catch all of our interviews with content marketing leaders. 

No spam, we promise—just two value-packed content marketing newsletters every second Monday. 

Plus, if you’re interested in customer stories and customer marketing, you can opt-in to receive a two more newsletters on alternating Mondays where we chat with leaders in customer marketing.

Speaking of customer stories, have a look at our 2024 Customer Story Trends & Insights Report, where we surveyed 115 customer marketers to gather their insights and experiences with customer stories.

Here’s a preview:

20+ Best Case Study Questions for Customer Interviews

Your customer is short on time, so be prepared with exactly which case study interview questions you need to ask. Also find out what 4 interview mistakes not to make.

Updated April 2023: Case studies are a critical element of most SaaS marketing strategies. But what case study questions do you ask in the interview to ensure you elicit an authentic and compelling story?

In research we conducted this year, SaaS marketers ranked case studies the #1 most effective marketing tactic to increase sales—ahead of general website content, SEO, blog posts, social media and other marketing tactics.

Gathering the insights, data and customer quotes that make a case study resonate, however, takes some savvy when coming up with relevant case study questions for interviews with customers.

In this post, we’ll explore the best case study questions to ask at your next customer interview. 

  1. Prepare your case study questions in advance
  2. The best case study questions for interviews with customers
  3. Find a convenient time for the interview
  4. Send the case study questions ahead of time
  5. An email interview won’t cut it
  6. Take notes and record the interview
  7. Watch out for these 4 common interview mistakes

20+ Best Case Study Questions for Customer Interviews is the 4th post in a 7-part series on best practices for case studies.

Prepare your case study questions in advance

Prepare your case study questions ahead of time

You’ll probably have just 20 or 30 minutes to capture your customer’s story so be thoroughly prepared before you even schedule the case study interview. Case study questions generally fall into these categories:

  • who your customer is (background)
  • what their pain is (challenge)
  • why they chose your solution (solution)
  • what results they experienced (results)

Usually, the most logical way to structure your case study questions is chronologically—it’s helpful to think of the case study as a story with a natural narrative arc:

  • beginning (background and challenge)
  • middle (solution, including implementation)
  • end (results)

Do you need help with your case studies? Partner with Uplift to drive more sales with case studies that convert.

The best case study questions for interviews with customers

Use the 4 categories below to craft a list of case study interview questions you’ll want to ask your customers:


  • Tell me a little about your company.
  • What do you love about working there?
  • Tell me a bit about your role.
  • What are your goals? Your company’s?


  • What business challenges were you facing that caused you to look for a solution?
  • Why were these challenges such a big problem for your company? For you?
  • What were you hoping to achieve with a new solution?
  • What criteria did the new solution need to meet?
  • How were you planning to meaure the success of the new solution?


  • What solutions did you try before you came to us? 
  • How did you discover us?
  • What did the vetting process look like?
  • Why, specifically, did you choose to work with us?
  • What services are we providing for you?
  • What challenges do those services solve for you?
  • Tell me a bit about the implementation process. 
  • How are we supporting you when you need it?


  • How has our solution impacted or benefited your end users?
  • How has our solution impacted or benefited your company as a whole?
  • Do you have any measurable data you can share around the impact or benefits of our solution?
  • Overall, what’s it like working with us?
  • What’s next for your company and us?
  • What advice would you have for others considering our solution?

Tailor these case study questions to suit the person you’re talking to. Eliminate any that seem repetitive or irrelevant—and highlight 1 or 2 from each category that are most important. Leave space and time for follow-up questions.

Learn how to write a SaaS case study in 9 steps.

Find a convenient time for the interview

Your customers are busy—and they’re doing you a big favor by participating in the case study—so be as flexible as possible when you’re scheduling the case study interview. And while you’ll likely want to talk to them for hours, be respectful of their time and ask for 30 minutes.

Send the case study questions ahead of time

Some people worry that sending case study questions in advance will result in less candid and honest responses. Not true. You want your customer to be at ease during your case study interview, and you want them to have all the information and data they need at their fingertips.

Providing the case study questions for interviews with customers ahead of time will lead to a more informative and useful interview. It also helps ensure that you have enough time to cover all the important points. During the interview, you can jump in with follow-up questions to dive deeper into certain areas if needed.

9 components your case studies need to include.

An email interview won’t cut it

Case study interview methods from worst to best

Don’t settle for a case study interview done by email. Not only are people more candid in conversation, but you’ll also be able to ask spur-of-the-moment questions and explore ideas as they’re presented.

Here are the 4 best ways you can conduct your case study interview:

  • face-to-face (this is the best and most personable choice; try to arrange this if your customer is in your region)
  • video call
  • phone interview
  • repurposing webinar

Take notes and record the interview

A recording and transcription of the case study interview will ensure accuracy and give you peace of mind. Down the road, you can also use the transcript for other marketing activities, such as grabbing testimonials and pull quotes, writing blog posts and more.

Use an app to record phone calls, or use Zoom or Google Meet to record video calls. Make sure you have permission to record the conversation.

Watch out for these 4 common interview mistakes

4 case study interview mistakes to avoid

1. Using yes/no questions

Does your list have any yes/no questions? If so, be ready with follow-up questions. Better yet, revise the question so it’s open-ended to elicit a more thoughtful response.

2. Not pushing for numbers

Don’t be afraid to ask for numbers, concrete examples or more information. You need these for a quality case study and this is your chance to get them. Don’t be afraid to repeat case study questions or rephrase them to make sure you get what you need.

3. Not allowing the conversation to flow

You don’t need to be rigid about asking every single question on your list. The best insights are often unexpected so allow the conversation to flow a little—but don’t get too far off-topic or you’ll run out of time.

4. Not listening to your customer

Don’t think you already have all the answers. Go into the case study interview with an open mind and be ready to listen.

Download our case study interview cheat sheet

Get help with your case studies

As a SaaS content marketing agency, we write case studies, ebooks and blog posts for high-growth SaaS companies like ClickUp, WalkMe and Lean Data. Check out our case study writing service.

Top Customer Marketing Challenges From the Field

Once you’ve got your customer marketing program off the ground, what do you do next? Read our interview with Heather Pritchett, Director of Customer Voice at OutSystems, to hear about the challenges she faces as she leads a growing and maturing customer marketing program.

Interview with Heather Pritchett from OutSystems

No one ever said customer marketing is easy, but that’s likely why so many creative, smart and engaged marketers are drawn to the field. Overcoming challenges is what keeps so many customer marketing professionals on their toes and always innovating.

And one such customer marketer is Heather Pritchett, Director of Customer Voice at OutSystems. Heather and I had a wide-ranging conversation about customer marketing, including:

  • new challenges she’s facing as her customer marketing program grows and matures
  • how she measures the performance of her case studies
  • some of the tactics Heather uses to streamline the case study approval process

Looking for a customer marketing solution?

Check out 29 Best Customer Marketing Solutions to Drive Customer Growth and Retention (2023)

Heather Pritchett interview

Heather Pritchett, Director, Customer Voice, OutSystems

Name: Heather Pritchett
Job title: Director, Customer Voice
Company: OutSystems
Heather’s hometown: Alpharetta, Georgia
Degree: BSc Marketing

Fun facts about Heather Pritchett:

☕ Tea, coffee, or something else?: Both! I have both coffee and tea most every day. And I’ve been known to enjoy some wine on occasion 😊
👉 We’ll often find you: At the gym….Or outdoors walking. I love being active and also in nature. When I can combine both it’s the best!
👪 You’re a parent to: Our hound dog Cooper – a rescue that has been with us for four years, and I enjoy being a foster mom to rescue dogs in need!
🛫 Last place you’ve traveled to: Hawaii, just after Christmas. It was my 2nd visit to the islands and I already can’t wait to get back!

How did you get your start in customer marketing?

Heather Pritchett: I went to school for marketing and my first role was in a small software company. I hadn’t thought about the technology industry for a career, but, looking back, I am really grateful for that opportunity as it gave me the chance to work in a dynamic, always changing and in-demand industry.

My early days of working primarily in corporate marketing exposed me to working with customers through customer stories, customer events, etc. I enjoyed interacting with the people who were actually using the product or service that I was marketing—and learning how they use it and how it brings value to them.

Then, as I spent several years leading marketing for the US region, I got the opportunity to spend more and more time with the customers and thinking about how to engage them.

The Chief Marketing Officer at OutSystems saw the need for and the value of customer programs. He said, “We’re going to make this a full-time role, and it’s global.” So I jumped head-first into it because it was a great fit for my interest and passion around working with customers.

Our team does not—and my role has never focused on—upsell, cross-sell, expansion or anything like that. It’s more about customer advocacy and engaging customers. A lot of expansion and retention comes naturally through the programs that we do, but that’s not been the focus. 

What has been your biggest customer marketing challenge in the past 12 months?

Heather Pritchett: One of the biggest challenges for me, especially as the team leader, is the shifts we’re trying to make. We’ve gone through a lot of the traditional stages of advocacy where we start with references or stories or reviews and more of the tactical programs.

We’ve gotten to a point now where we have a lot of stories, a lot of online reviews, a lot of customer advocates. Now it’s, ‘we’ve got these assets, so where do we go from here? How do we leverage what we have? And then how can we be strategic in the way that we’re serving the needs of the business? How do you really quantitatively measure what you’re doing and the impact to the business?’

It’s been a shift of trying work towards those goals, but then also maintaining the stuff that still needs to be done, like fulfill reference requests and speaker needs, publish stories and those kinds of things. 

Have you had any other challenges recently?

  1. One challenge is engaging those larger customers because it can be difficult to get some of the larger organizations that are more broadly known to tell their stories.
  2. Another challenge is thinking about how we need to shift our storytelling model. We’re getting higher demand for video and shorter formats, and we’re trying to determine the strategy around how stories fit within that. What types of stories do we need when and where?

What’s your biggest customer marketing success in the past 12 months?

Heather Pritchett: It’s not one defining thing. Seeing our company become more customer centric is extremely rewarding. To see our customers featured and highlighted as successful and innovative is a huge success to me. Having our team be seen as highly valuable to our organization is a huge success!

How do case studies play a role for OutSystems?

Heather Pritchett: Case studies aren’t just assets that live on our website. There’s also a huge amount of value in leveraging the stories in many different ways: 

  • Case studies are one of the first places that our PR team goes to look for story ideas to pitch to the media.
  • The Demand Gen team uses them in campaigns for customer proof.
  • Sales are asking for case studies with different use cases all the time.  Case studies definitely help provide a foundation for Sales to have something to point to.

How are you measuring the performance of your case studies?

Heather Pritchett: For a while we were watching web traffic. Then, as we shifted our strategy to focus more on story impact outside of our own properties measuring traffic brought less value.

One of our best indicators from a case study perspective at this moment is internal consumption. We’re looking at Highspot, which we use as our field repository for content. We watch consumption levels to make sure that we’re educating our teams on what is available for use.

What are some of the challenges with producing quality case studies?

Heather Pritchett: The first thing that comes to mind is that it’s a lengthy process. Case studies can be expensive, and the approvals are challenging.

Getting business value metrics is also pretty difficult sometimes. Either the customer doesn’t know them or they don’t want to share them. A full-length case study of the quality that we like can take a very long time and can be very challenging with the customer’s approval processes. 

What tactics do you use to streamline the case study approval process?

Heather Pritchett: Connecting with our customer’s Communications Team upfront has worked well. The better aligned we are with them, especially with the larger companies, the more easily we can produce the story that the customer wants to tell. 

Our awards program has also been a great way to showcase the success of our customers. This is a big recognition and celebration for them and their teams, and the case studies generated through this program are a great tool for the customer to promote their achievements internally. 

We also want to try shifting into some of the smaller, lighter-lift case study and testimonial formats, so we can get them produced and approved faster. It would be less where we’re writing the customer story and more letting the customer tell their own story. We’re in full experimentation mode with this. The idea is to have a range of case study and testimonial formats so we can decide what’s right for a specific purpose and customer.

What advice do you have for someone new to customer marketing?

Heather Pritchett: Understand what your business goals are, and focus on the top two or three programs that will impact those goals. Then build from there!

P.S. Want more customer marketing insights?

If you’d like access to more customer marketing insights like this, sign up for our newsletter to catch all of our interviews with customer marketing leaders. 

No spam, we promise—just two value-packed newsletters about customer marketing and case studies every second Monday. 

Plus, if you’re also interested in content marketing, you can opt-in to receive two more monthly newsletters on alternating Mondays where we chat with leading content marketers.

And just in case you missed it, check out our 2024 Customer Story Trends & Insights Report, where we surveyed 115 customer marketers to gather their insights and experiences with customer stories.

Here’s a preview:

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