How Holly Stanley Creates Content for Shopify, Vimeo, and Hootsuite as a Freelance Content Writer

Discover how this freelance content writer creates content

At ease, Captain!

Welcome to a free edition of the Content Captains Newsletter where I answer your questions about creating content, generating traction, and becoming a full-stack content marketer.

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Introduction

Holly Stanley is a freelance content writer based out of Buenos Aires, Argentina.

For the last six years, Holly has created content for B2B SaaS companies like Shopify, Vimeo, Hootsuite, Ahrefs, and Clearscope. When asked how she’s been so successful as a freelance content writer, she said:

“It’s super important to fully understand the scope of the project and client expectations before starting. I don’t shy away from asking plenty of clarifying questions about their audience and goals.”

In today’s interview, we cover how she got started, how she works with clients, and what skills you need to be a successful content writer. 

1. How long have you been a freelance content writer for B2B SaaS companies?

I’ve been a freelance writer for 6 years. But I only went full-time and decided to go all in following a pandemic layoff in March 2020. Up until that point, I had been freelancing on the side. 

I went freelance because I realized that securing another full-time job in travel would be nearly impossible during the pandemic. Then, 6 months into full-time freelancing, I was making more money than in my previous full-time job, so I never looked back. 

I chose B2B SaaS companies because I thought there’d be a tech boom due to the pandemic. I also felt it was a niche with long sales cycles that made it suitable for content marketing. 

2. How did you land your first client? 

My first freelance client approached me on LinkedIn. At the time I had been working for an English news outlet in Buenos Aires, Argentina. The client, a B2B marketing agency, also based in Buenos Aires, was looking for an English-speaking content writer. The founder used to read a column I wrote titled “What to do in Buenos Aires at the Weekend”, and decided I could write some content for their clients. 

It felt great, as I realized that content writing was a viable way of making money while working remotely!

3. Who was your first “big” client? 

My first big client was Shopify. I was lucky that it came through a referral. A content marketing manager I had previously worked with, put a call out on a Slack community channel for freelancers. I wrote to her and she put my samples forward. A few weeks later, she started assigning me posts. 

I had wanted to write for Shopify for a while before starting work with them so I was hyped. They’re very well-respected in the content marketing world so I was excited to see my name as a byline. 

4. How do you acquire new clients? And what kind of work do you do for them?

I find clients through a whole mix of channels. Right now, LinkedIn works well for me. Some clients write to me directly after engaging with my content, and sometimes I approach content managers if I think I’d be a fit for their program. 

Sometimes clients contact me through my website or after reading a piece I’ve written for a big website. 

I also find clients through community Slack channels and referrals too. 

My preferred method of working is to agree on a set number of articles a month––usually between 3 and 5. I’d say, generally, it’s easier to project manage a recurring set of deliverables. It’s also nice to get into a rhythm with a client and help them reach long-term goals. 

Currently, I’m doing more ad-hoc work, which allows for more variety. I think this is due to instability in the tech world and uncertainty around marketing budgets.

5. How do you price your services? 

I prefer to price per blog post or content asset. It makes sense to me to price for research, writing, and editing at one flat rate. It’s then up to me how to budget my time for the project. For some content, I may charge per word. 

For me, per hour can feel tricky. How am I meant to charge for the time I was thinking about content while walking the dog? Every year I write, my processes get faster and more efficient too, so I don’t want to feel penalized for working efficiently. 

6. How do you keep clients happy and coming back?

It’s super important to fully understand the scope of the project and client expectations before starting. It sounds obvious, but making sure I have access to all Google Docs, platforms, and internal SMEs before I start is essential. I don’t shy away from asking plenty of clarifying questions about their audience and goals. 

Following that, it’s about delivering what you said you would on time. I try to be super responsive to edits and feedback too. I’ll make any edits within 2 business days and I keep a running doc of feedback so each piece gets better and better.  

7. What are the types of projects you usually get hired for? How do you measure success for yourself/your clients?

B2B SaaS brands usually hire me to scale up their blog. I mainly write and refresh blog content but also take on customer stories, whitepapers, and ebooks. This year, I’ve started offering thought leadership too. 

Most clients I work with already have their content strategy down. So success is a case of executing projects to a consistently high standard and on time. 

Success for me looks like a steady workflow where I’m working on projects I like, meeting financial goals, and enjoying a good work-life balance too. 

8. What’s your superpower? 

My superpower is research! I dig into industry reports, interview experts, and read loads of content before I write. At the same time, spend a lot of time learning SEO and subscribe to Ahrefs and Clearscope to improve on-page SEO. 

9. What’s your number one content writing tip? And what are the top 3 skills every content writer should know? 

Make time to read. Choose some of your favorite content writers and spend time reading their articles. You can learn a lot from reading great writing––everything from structure to word choice, and how they tell a story. 

Reading fiction is also important. Call it osmosis or something else, but I find it much easier to write when I make time to read a good book. 

Top 3 content writing skills: 

• Solid research skills - You need to be able to leave no stone unturned and be prepared to dig when others wouldn’t bother. This is what will make your content stand out for originality. 

• Project management - You’ll probably work on multiple projects at once, so you need to learn how to block your time and get things done on time. 

• Editing skills - I often spend more time editing my work than writing! You need to know how to turn an ugly first draft into something your client and their audience will love. 

10. What’s the biggest mistake you made when you first got started in freelance content writing? What did you learn from it?

I used to say yes to every project that came my way and overbook myself! I started full-time freelancing during the pandemic and sometimes there wasn’t much to do besides work. This led to lots of late nights and work on the weekends. That might be sustainable in the short-term but it’s not for months on end. 

I burned myself out and realized I didn’t want to put myself in that position again. So I learned how much I can realistically deliver in a 5-day work week. I now use time-tracking software to help me estimate how long each project will take so I can block time properly. 

Thank you, Holly, for jumping aboard and sharing your story with us. 

For more content writing and freelancing tips, you can follow Holly on LinkedIn or check out her website for examples of her work. 

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Thanks for reading,

Content Captains