Episode 011: From ESL Instructor to Freelance SaaS Writer | with Ashley Cummings

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In this week’s episode, we chat with Ashley Cummings, a freelance writer for SaaS, e-commerce, and marketing brands.

Ashley has written for top brands like Shopify, Copyhackers, Clearscope, Dreamhost, HostGator, Salesforce, and many others.

On the personal side, when Ashley is not being a freelance SaaS writer, she’s writing a newsletter called Content Connect that reaches 7,000 content marketers and writers.

I hope you enjoy the episode, and let us know what you think about it.


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(00:00) – Introduction

(00:46) – Meet Ashley Cummings

(01:20) – Will AI replace marketing jobs?

(03:37) – How can you join the 5% of marketers whose jobs cannot be replaced by AI?

(05:17) – How and why did Ashley Cummings get into marketing?

(06:53) – What client acquisition method does Ashley use to work with leading SaaS, E-commerce, and marketing brands?

(09:15) – How do you balance work and motherhood?

(11:36) – How do you create a SaaS writing portfolio for anyone transitioning from other content writing industries to SaaS?

(14:28) – How do you write content your readers will remember and share?

(19:26) – How do you find subject-matter experts to interview for SaaS blog articles?

(21:31) – What tools does Ashley use as a freelance SaaS writer?

(22:52) – Least and most amount earned as a freelance SaaS writer

(24:17) – When and how to raise your rates?

(27:32) – How to become a successful freelance SaaS writer and be easily recommendable?

(29:16) – Ashley’s career’s biggest challenges and how she overcome them

(30:49) – Predictions: How will marketing evolve in the next 5 or 10 years?

(31:57) – Favourite type of wine

(32:33) – If you could have a glass of wine with any marketing professional, past or present, who would it be?

(33:10) – Learn more about Ashley Cummings


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This episode was edited and produced by Olawunmi Olaniyi.


Ashley’s Facebook Group: Freelance Copywriters & Content Writers

Ashley’s Content Connect Newsletter

Read Ashley’s Freelance Writing Rates Report 


All background music used is by various artists on Pixabay.