Anna is an experienced conversion copywriter and email strategist, with a proven track record of crafting compelling copy that drives engagement and sales. Trained by Copyhackers and certified by Hubspot, her background in publishing, marketing, and PR informs her unique approach to copywriting — an approach that helps clients connect with their ideal audience.
A proud Jamaican and avid traveler, Anna’s diverse experiences and passion for exploring the world fuel her entrepreneurial spirit. Her background is as varied as it is rich, encompassing everything from publishing, retail, and customer experience to public relations and digital storytelling, making her an effective secret weapon for her clients.
Jump to the topic you are most interested in:
I got my start as a freelance copywriter on Fiverr in 2015. It was a way to make extra money while I was working as a marketing manager for a small boutique publishing company.
Fast forward to 2018 when I quit my cushy senior management position to travel full time — copywriting was the thing I relied on to earn money while traveling. The COO at Wishpond found me via Linkedin and I worked remotely and took further copywriting training with Copyhackers while traveling full-time.
During my time at Wishpond, I wrote copy for social media, PPC ads, chatbots, landing pages, websites, SEO blogs, and other channels, but email was about 50-60% of the workload. I loved it so much that I took further training through Copyhackers to continue improving my skills in email copywriting and strategy.
I started AFIWI Marketing officially in 2019 and have been serving clients since then, sometimes alongside a 9-5 and at other times, full-time.
Being Jamaican is a point of pride for me, so it made sense to make our local dialect part of my brand, through my company’s name. It allows me to show up online as my authentic self.
As for BlackFemaleCopywriters.com, I started the directory as a way to create a space online for black female copywriters who in my own experience, sometimes struggle with promoting themselves and finding customers. While as a Jamaican, I am used to seeing people like me holding senior roles across all industries, I find that is not always the case in a global environment. With BFC, I can help bridge that gap on the international stage.
It’s still early, but my plan is for the site to eventually be more than just a directory, and serve as a space for us to share industry knowledge and collaborate while supporting each other.
Copywriting can serve many functions — information, education, entertainment, or inspiration, for example. And it can take many forms — taglines, website copy, blog posts, emails, brochures, to name a few.
What separates conversion-focused copy is its singular focus — to get the reader to take a desired action. That may be to register for a webinar, sign up for a demo, start a free trial, buy a product or service, download a resource, or something similar.
Because there is a specific goal, audience research is required so we can write effectively for that audience. And persuasive techniques based on behavioral sciences/psychology are also important.
With regular copy you may write something on a whim because it sounds catchy or clever; with conversion-focused copy, you employ persuasive techniques and write based on what the research tells you will work for your target audience. It’s not a perfect science, but it’s a million times more effective than guessing.
I believe AI tools have their place in most industries, but we must be careful to not assume they are more competent than they actually are.
AI tools aren’t (yet) able to conduct customer research, distill those findings, and craft conversion-focused copy the way a trained copywriter can. But that doesn’t mean we can’t use these tools to support our research process and pre-writing.
I’ve experimented with several AI tools and some of them were not as impressive as they claimed to be.
Right now, I use ChatGPT for personal projects like my various website blogs. I use it to brainstorm content ideas and create outlines for long-form content. If I’m stuck with a blank page, I like using it to generate ideas that I can iterate on.
I may be biased because my background prior to copywriting was in customer service, but I truly believe that prioritizing the customer experience is the best way to do business.
I think all marketing strategies should consider the customer lifecycle and the customer’s experience. Because ultimately, we’re selling to people — whether they’re making decisions as individual consumers (B2C) or as part of an organization and its goals (B2B).
When I’m thinking about an email campaign for a client, I always consider the recipient:
When I talk about lifecycle marketing and customer experience, I’m simply saying “let’s get to know our prospects or customers intimately so we can send them the right message at the right time to drive desired outcomes while helping them achieve their own goals with our solutions.”
The key stages of the customer lifecycle are essentially an expansion of the stages of the traditional sales funnel.
While the traditional funnel ends with the purchase, the customer lifecycle extends beyond that to the post-purchase nurture stage (usually where onboarding happens), retention, and advocacy (where that customer becomes a brand ambassador of sorts, telling their network about a brand’s product/service).
Emails are a great tool to use throughout these different stages because they’re one of the easiest ways to maintain communication with customers. A few examples come to mind:
And there are many more use cases beyond these.
If the emails are for a new audience, I start with research to learn as much as I can about them — review mining, voice of customer data, founder/owner interviews, demo call recordings, etc.
Once I complete the research process I clarify the goal of the sequence and the audience.
Do we want readers to reply to our emails to book a discovery call or click a link to purchase a product?
Is this a cold email sequence being sent to B2B prospects or a sales sequence being sent to an engaged segment of subscribers who open most of our emails?
Nothing gets written before I’ve answered all these questions because these considerations usually help shape the final campaign.
They also inform things like email length, format (text-only vs images and text), number of emails in the sequence, and wait time between emails.
When it comes to writing the actual copy for each email, subject line, and preview text, I’m always guided by the rule of one — one big idea, one reader, one promise, one call-to-action.
I start with my call-to-action and write the rest of the email once I’m clear on what I want the reader to do. I write my subject lines and preview text after the email is finished. I find it easier to work this way since the body copy usually gives inspiration for subject lines.
Last year an e-commerce client approached me to write her welcome sequence and a nurture sequence for new subscribers.
She had a great skincare product, a long list of satisfied customers (with tons of testimonials to prove it), and was looking for a way to connect with new subscribers who sign up via her website popup for a 10% discount.
One thing we decided to do differently with the sequence was to have each email come directly from her as the founder, instead of making it seem like a generic email from a faceless brand (which is often common in e-commerce). And I recommended this approach because when mining her customer reviews and researching her audience on social media it was clear that a connection to her as the founder was a key part of the relationship with her customers.
I also used a lot of testimonials — which worked great because she had sooo many available for me to choose from, and the Before & After photos worked well to enhance her social proof.
A key understanding of her target audience and their goals (as well as how her products helped them achieve those goals) made the campaign very successful. She was able to recover her investment for working with me within one week of the welcome sequence being implemented. And it continues to generate revenue to this day, though when we last spoke recently we talked about refreshing it.
Finding the right lead magnet is tricky if you’re not clear on your target audience or your offer. But once you’ve nailed those two things it does become a little easier.
A rule of thumb is to think about what you offer and the problem you solve for your customers, then brainstorm for lead magnets that either:
In addition, I would say don’t make it complicated. Make it actionable and give your subscribers a quick win.
I’m not sure what it is with emojis but I’ve had success with emojis in email subject lines when I’ve run split tests (just one per subject line though).
I also find that questions as subject lines work well to pique the reader’s interest, along with shorter subject lines.
Beyond those approaches, I think the best way to get people to engage is to send content they want to read and engage with. It’s also helpful to use a sender name that’s consistent and recognizable so they know when you’re emailing them.
I’m not a fan of trends when it comes to email marketing, and marketing in general. Trends come and go, and sometimes hopping on that bandwagon can do more harm than good for a brand, especially when that trend negatively impacts the customer experience. So I typically steer clear and recommend the same to my clients.
An example that comes to mind is the use of “re:” in an email subject line. That one has been around for a while but I’ve been noticing it more in my inbox of late and I see more people complaining about it.
It’s a terrible practice that I would never recommend, regardless how popular it may seem. Because using re: in the subject line of an email that is not a reply is a quick way to lose your subscribers’ trust and damage your integrity.
Once you get someone to open your email (this is where) the real work begins.
There really are only 2 effective ways to measure engagement — replies and clicks, and in some instances, you may even consider forwards. For this question, my focus is primarily on replies and clicks.
I think the approach that works best is going to be dependent on your audience, your offer, and your goal.
I ran an A/B test for a B2B campaign where we sent out a demo invite sequence and asked leads to reply in one set of emails and asked leads to click a link to book a demo in the other set. We had more success/engagement with the reply request emails.
This approach would not work for an e-commerce brand selling a product or for a coach sending out a cart open email for a new course. In the e-commerce example, a call-to-action button with clear compelling copy that drives action would be most effective, while the coach may have better luck hyperlinking an action-driving sentence or phrase to the sales page.
I’ve been reading a lot of newsletters for the past year or so, so I haven’t been getting a lot of marketing emails. But of the few I still get, I love reading the subject lines for AppSumo emails. It’s clear that whoever’s writing them is having fun while doing it!
I’ve also been loving TLDR — a weekly financial newsletter from the WealthSimple team. That’s another one where it’s clear the writers are having fun writing the content.
I love their generous use of emojis and GIFs and the way they make an otherwise boring topic interesting for me.
DO get to know your audience and their needs. Whether through polls or encouraging them to reply to your emails…don’t make assumptions about what they want from you or how you can help them. When in doubt, ask.
(I want to add a caveat here that this approach may not always be feasible for a more sophisticated audience — especially in the B2B space. For some audiences, you will need to find other ways of confirming what they need from you. That may be online forums, Reddit threads, social media, industry/trade publications, sales call transcripts/recordings, live events, etc.)
As far as things you should not do, NEVER send an image-only email to your subscribers. This is common with e-commerce but it is a trend that absolutely must die. It’s really bad for accessibility, makes it impossible for your reader to see anything at all if they don’t have images enabled, and makes it impossible to confirm what worked when trying to track conversions.
Just don’t do it.
