Ashley R. Cummings Interview: Freelance Writer for Commerce, Retail, & Marketing SaaS

Back in 2011, Ashley R. Cummings was working two jobs as a corporate trainer/instructional designer and a Russian instructor at a university when she realized that colleagues were constantly showing up at her desk asking for proofreads, edits, or feedback on their writings.

That’s when she decided to go back to her roots (she had majored in English) and launched her freelance writing career.

Today Ashley has worked with some of the biggest brands in commerce, retail, marketing, and sales like LinkedIn, Uber, Shopify, Salesforce, Lume, Campaign Monitor, Omnisend, HostGator, and more.

In the following interview, Ashley was kind enough to answer some basic content writing-related questions for our readers.

Ashley R. Cummings

Let’s start with your background…What did you want to be when you were young? And how did you end up becoming a content writer?

When I was really young, I wanted to be a garbage collector (seriously) because I thought it looked fun to drive a truck. When I was older, I wanted to be an English teacher. I studied English and Russian and started teaching, but I wanted to make more money. From there, I started freelance writing.

2. Anyone who wants to build a career in content writing, how do you suggest they get started?

Start writing.

3. Any tips on how to improve one’s writing and job skills?

The longer you do it, the better you get, so keep practicing. It’s also essential to study other great content writers and read a lot.

4. How did you choose your niche (i.e. Commerce, Retail, and Marketing SaaS)?

I chose SaaS because I was mostly getting SaaS clients. Then, I kind of fell in love with the niche.

5. How did you find your first writing gigs? And any tips on pitching to new clients?

I asked my current network if they needed help and several people took a chance on me.

6. How did you deal with the initial rejections?

I usually stew about it for a day and then move on. Rejections are TOTALLY normal in freelancing. Sometimes it’s a fit. Sometimes it’s not. And that’s okay.

7. How do you maintain a good relationship with clients?

Stick to your word. Turn things in on time. Be kind.

8. Would you say building a website is necessary for beginners?

Yes, 100%. A website is your digital real estate that shows off who you are as a freelancer. It houses your portfolio and tells potential clients everything they need to know about you to hire you. It also levels up your business and shows you’re a true professional. This allows you to boost your prices.

9. How much should freelance writers charge per word?

It totally depends on the type of content, your experience, and the scope of the project. I created a 34-page report on this that you can download here

10. When is the right time to increase one’s rate?

It’s always the right time. Try increasing your rate by 10% with each client.

11. Do the rates include on-page SEO and drafting?


12. Do you use any invoicing software?

Yes, I use WaveHQ.

13. What is the best way to accept payment?

Direct deposit into your bank. There are no fees with this method.

14. In the freelance writing space, what challenges do you believe aren’t talked about enough?

I think there should be a more open discussion about how much you should charge to make a living.

15. What tools do you use to manage your own time and workflow?

Trello. Google Suite. I also really like tools like Moxie and Harlow.

16. What are some non-fiction books that helped you in your career?

Letters To A Young Poet by Rilke

17. And finally, if you had to go back in time and offer advice to your younger self at the beginning of your writing career, what would you say?

Stay consistent, don’t give up, and network with other writers.

18. Where can we find you online?

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