Content Marketing Expert Interviews: Series 1

Erica Schneider: The Queen of Editing

Erica Schneider

1. How did you get started as a content writer and editor? What was your journey like?

I knew I loved writing but had no clue how to apply that passion into a real-world job. So I didn't fall into writing and editing until my 30s. I decided to teach abroad and had to relearn English grammar. The act of working with and explaining words got me thinking: "I wonder if I can make money editing?" All the digital nomads I was friends with in Thailand were on Upwork, so I created a profile and applied to hundreds of gigs. If memory serves, my first job was proofreading a digital magazine. I got paid next to nothing but still, I got paid. From there, I started dabbling in article writing and learned everything on the job. One thing led to another and I found a Grizzly. Started as an editor and moved up.

2. If you could give writers one piece of advice that will help them improve, what would it be?

Pay attention to feedback. Every single suggested edit, comment, and note. You are getting on-the-job advice from people that (hopefully) are experienced and know what they're talking about. It won't always feel good, and can sometimes be unhelpful, but most of the time it's gold. If you don't understand why an editor/client made a change, ask. They may not have time to explain every single one, but anything is better than nothing.

Eva Gutierrez

1. How did you get started as a freelancer? What has your journey been like?

I got started on Upwork in 2017. I used to sit on my computer and constantly refresh the feed so that I could be the first person to respond to a writing gig.

At that time, I took anything and everything. I thought it was so cool to get paid to write and didn’t care about the topic (yet).

I wrote about lawn care, e-commerce product descriptions, moving company copy, etc. There was no job I would turn down at that time, haha.

I stayed on Upwork for way too long. This had a pro and a con.

Pro: I learned how to become REALLY good at pitching my services. I used to respond to 10+ writing gigs a day, and I started to learn what made me stand out based on how many of the gigs I landed.

Con: I worked on small, one-time projects for so long (like 2 full years). This meant that I was constantly in sales mode. I’d land a project, feel amazing, and two minutes later realize that I needed to land another one immediately.

This was so draining and kept me in a famine mindset when it came to writing work.

2. What has your journey been like?

You can’t be what you can’t see. It wasn't until I talked to another freelance writer and he told me about retainer contracts that I realized how to actually freelance.

Retainers meant consistent income. I would know how much money I was making that week, that month, and that year. It was such a mind-blowing concept to me.

Because I’d become so good at pitching my services thanks to my Upwork days, I started pitching myself to companies I wanted to work for.

I pitched a company, and they brought me on for a $4k/month retainer. That was the most I’d ever made in one month, let alone with one client.

I pitched another company and landed a $2,400/month retainer. This client wasn’t even looking to hire a writer. I just crafted a pitch that showed the value of my writing so well that they decided to bring me on for a retainer.

After that I never worked on one-time projects again and exclusively worked with companies who wanted long-term work.

What is one piece of advice you'd give another freelancer who is interested in selling digital products?

I’m going to make the safe assumption you’re trying to coach other freelancers or teach people how to do your freelance writing skill (example: how to write better).

You have a lot of competition. That’s not a bad thing - it just means you have to play the game differently than somebody who has 0 competition.

Your goal is to become the person that doesn’t have competition. How do you do that?

Differentiate yourself. Look at your skill set and what you’re trying to teach and figure out what makes you different.

For example, I ran a coaching program for freelance writers a few years back.

Here’s a generic description of what I did: I showed freelance writers how to get clients.

Here’s what differentiated my program: I showed freelance writers how to get clients through cold pitching so they never had to rely on a platform or their network for work.

You have to differentiate yourself to stand out. And luckily for you, everybody finds success as a freelancer slightly differently.

Whatever you’re teaching - look at how YOU did it and how you can systemize that for other people. Then, write copy and content endlessly about that differentiating factor.

Justin Moore

1. How did you get started as a sponsorship coach?

My wife, April, and I have been involved in the online world since 2009. My wife started her first channel in 2009. At that time, I wasn't really involved, but as more brands started to show interest in collaborating with her, especially when they wanted to compensate her for discussing their products on her channel, I was drawn in. I was in business school then, and thought I could assist, particularly with understanding contracts and other behind-the-scenes aspects.

Fast forward a bit, collaborating with brands became a significant part of our business. Seven years ago, I started an influencer marketing agency to facilitate brand partnerships for other creators. Over time, I acquired a wide range of experiences. We had been in the trenches for years as creators, completing hundreds of deals.

I think I just invoiced sponsorship number 530, or something like that. We've completed many, but I also secured over a thousand sponsorships through the agency. This gave me experience from multiple perspectives, not just as a creator, but also working behind the scenes with brands and agencies on how they decide to allocate significant funding to creators. We often discuss the platform strategy for large budgets, like $500,000.

About three years ago, I wanted to address a concern I had been noticing. I felt that creators were making many mistakes when interacting and negotiating with brands. So, I started making YouTube videos on the topic. At first, I didn't envision it becoming my new business. I simply wanted to share advice on how to pitch to a brand, set rates, advocate for oneself, get on a brand's radar, and develop long-term partnerships rather than just one-off transactional ones.

My YouTube channel began to gain traction from there. Initially, I made videos about a range of topics, not just sponsorships, such as link-in-bio tools and other things. But about a year and a half ago, one of my followers messaged me suggesting that I focus solely on sponsorships, as that was my area of expertise. I thought that was a good idea.

I updated my Twitter headline to "Sponsorship Coach". It seemed novel at the time, as I hadn't heard of anyone else using that title. I'm clear in defining my role as an educator, not a manager. You can't retain me in the traditional sense, but I can provide you with knowledge.

People started reaching out, asking for help with complex negotiations. I saw a need among creators who had a significant, but not huge following, ranging from 10,000 to several hundred thousand followers. These creators were earning money and needed assistance, but they weren't large enough to require a manager. Even as creators grow, many prefer not to have a manager. For example, my wife and I have never had one.

My model, which is to provide objective advice, has appealed to many creators. I have no vested interest in the deals I advise on, so I'm equally ready to tell a creator when a deal is not good for them. Often, the financial incentives of managers can be misaligned, as they take a cut of every deal.

2. What is one piece of advice that you'd give freelancers with a small but growing social or newsletter audience for monetizing through sponsorships?

My one piece of advice is: start now. I've found that for all, like the majority of creators, freelancers, solopreneurs, whoever it is, they all have this arbitrary milestone or threshold in their mind that they have to hit - 10,000 followers on my newsletter, or 10,000 people on Twitter, or 10,000 subscribers on YouTube, whatever it is.

And when I ask people where that number came from, it's either 'I made the number up' or 'I tried to sign up for a sponsorship platform marketplace one time and they said I had to have a certain minimum number'. So they thought that was the threshold for everyone. This is a big misconception. You do not have to wait. Every advertising agency has different metrics, success metrics, in terms of who they're looking to partner with. The more niche you are in your craft or space, the better. The easier it is to pitch partnerships because there aren't as many people like you around.

So, the biggest piece of advice that I can give to those people is: you have to overcome this limiting belief that you have to have a certain minimum size audience to actually start engaging with sponsors. If I could add one more tip, it's this: stop waiting for the partnerships to come to you. A lot of people think, especially in this early trajectory, 'I'm just going to wait until an opportunity lands in my inbox'. But in reality, the most lucrative partnerships that you're ever going to land are going to be from you shooting your shot and reaching out and pitching.

You could probably relate to this in your own freelance career - those opportunities where you're the one pitching and saying, 'Hey, let me do this for you', it's going to stretch a partner's mind. They might think, 'Oh, I didn't even know you'd be interested in something like that. Let's talk.' So yeah, hope this helps, and let me know if you have any other questions.

Michael Keenan

1. Tell me more about yourself

My name is Michael Keenan and I’m a freelance content writer and SEO for software brands. I work with many clients in the ecommerce tech space, which has given me much respect for retail brands and what they go through for customer acquisition, support, and retention. Anyway, I do a lot of content updating these days to help big blogs optimize their old content. It’s a newer niche that I’ve truly fallen in love with doing, more so than writing net new content.

I’m also the co-founder of Peak Freelance, the premier community for freelance writers. We have over 250 members that come together to learn, collaborate, and inspire each other to become better writing business owners. Peak Freelance is also an education hub, where we provide courses, templates, prompts, and interviews with content experts to help writers improve their skills.

I live in Guadalajara, Mexico, with my partner and two Xoloitzcuintles, which are Mexican hairless dogs. I love being outdoors, running, investing, and starting new businesses.

2. If you could only give new freelancers one piece of advice, what would it be?

My first instinct would tell you to find a niche. But you’ve probably heard that advice a million times already. The truth is, though, that there are riches in the niches. Becoming an expert on one topic helps you build a source network, write more in-depth (and faster) about the topic, and earn more money.

BUT since I don’t want to bore you with the standard tip. My one true piece of advice would be to build a network. That’s something I did not do that I wish I had done in the beginning. I had zero network when I started freelancing. I didn’t come from an agency or corporate role with pre-existing contacts. I came from sending out 20 to 30 cold pitches per day on job boards and Upwork. It took me years to even get on Twitter and LinkedIn to start connecting with clients and peers. One client I have now, which nets me 5 figures per month, I got from a friend who I had a virtual coffee with years ago. She was leaving freelance and passed off her clients to me… and now, she’s my client at her new company

So thinking back on it, I would say to get your beautiful face out in public and start building your network. Obviously you want to connect with potential clients (hence, the whole niche thing), but you also can connect with other freelancers. Many of us pass on work to our network, and those leads are warm. It serves as another lead generation channel for your business, AND you get to meet awesome people along the way. Freelancing alone is boring. Freelancing with friends and peers is exciting.

Alexa Richardson Kilroy

1. How did you get started with marketing/branding? Take us through your journey up to Triple Whale.

Weirdly enough, I started my career as a High School English teacher. I graduated from Boston College with a dual degree in Secondary Education & English, with a business minor. I thought I was going to teach forever, but after moving to a new city with a rapidly rising cost of living (Austin, TX) right out of college, I found it pretty unsustainable. After teaching, I worked for a bit in ed-tech, and then dabbled into the world of ecommerce. I fell in love with the industry quickly, and spent a lot of time educating myself with the resources and experiences necessary to become a successful growth marketer.

Marketing on the DTC brand side was so rewarding; I had the opportunity to manage seven figure ad budgets for multiple DTC brands, spent hours studying consumer behavior and digital marketing data, developed creative strategy from the ground up, wrote LOTS of copy, shot product creative, and built performance marketing teams for brands. Basically - if it's in eComm and it's related to marketing, I've probably done it. In early 2022, I was recruited by Triple Whale’s former CMO, Rabah Rahil, to join as Head of Brand. In case you can't tell from my blue-on-blue event outfits or Twitter presence, I love my job & my company so dang much.

2. What made you take up branding for a SaaS tool? What were the considerations before you said "yup, this looks like a feasible idea"?

Honestly, I credit so much to Rabah Rahil, our former CMO. I wasn't itching to jump from the DTC brand to the ecommerce SaaS side by any means. It took a few meetings over cocktails and snacks before I really started to consider the idea - and that's no fault of Triple Whale at all. I was honestly worried that I'd be bored in the SaaS world, since the DTC brand side is so fast-moving. Little did I know how quickly Triple Whale would start shipping products...And of course, these conversations happened in January of 2022 - before Triple Whale's Pixel release (attribution solution), also well before we hit our stride in brand awareness.

Beyond Rabah's persuasive pitching, what energized me the most was the quality of the team, and the vision for the product. As a former growth marketer/media buyer, I understood the massive impact Triple Whale could have in the market. I believed in the value of the product before I even joined the team, and I knew how hungry DTC players would be for a solution like ours. After some reflection, I realized that marketing a product that solves highly frustrating challenges for folks in roles just like mine could be incredibly rewarding. I also spoke with a few of my professional mentors who agreed that the role would be an awesome growth opportunity. Thankfully, I took the plunge. It's been such an honor and a blessing to be a part of team whale!

Kristen Hicks

1) How did you get started as a content writer? Take us through the detours in your journey till here.

I went to a liberal arts school that did a great job of teaching me how to research and write, and a terrible job of showing me how those skills could translate into a career. I ended up in an admin job for a small business whose owner recognized my writing skill, and shifted me over to marketing.

That same employer later misclassified me as a contractor, which led to a harsh lesson in the differences between freelancing and employment (don’t misclassify your employees, people!). But I came away from that lesson understanding that freelancing was what I wanted to pursue. After some negotiation, that company became my first client.

I spent my first three years or so as a freelancer learning everything the hard way. Then I started more actively networking with other freelancers, and it changed everything. People (mostly other women) shared their insights about typical rates, contract terms, important boundaries to draw all the stuff it’s hard to figure out on your own. I started to charge more, say “no” more often, and focus my services on the types of work I do best (blog posts and longform content assets, mostly for B2B tech brands). That’s worked well enough to keep my business going for over 12 years now.

2) How have your opinions evolved on the AI/chatGPT in the past few months? Do you find it somewhat useful for marketers?

Confession time: I have not used ChatGPT or any comparable products much yet. Most of my experimentation with ChatGPT so far hasn’t produced much that’s useful. But I recognize that it takes time to learn how to use these tools well. So I’m still mostly in “listen and learn” mode, with some experimentation mixed in.

When all the buzz around ChatGPT was new, my initial sense was that it was overhyped. Which I still think is mostly accurate—a lot of people went too far in their early proclamations about its influence. But at this point, I do think it has the potential to be a valuable tool if you use it for the right reasons.

Don’t ask it to write you a blog post and expect it to produce something relatable, original, or even accurate. But for other tasks—brainstorming topic ideas, coming up with title options, or creating social content based on your blog posts—it could become a useful part of the writing process. I’m paying attention to what I hear from other writers on its best uses, and intend to work it into my own processes more over time.

Kat Ambrose

1. How has your content marketing journey been? How did you get started?

My content marketing journey was a bit atypical (but what is “typical,” really?).

I got into content marketing over five years ago now. I left my mentally-taxing agency job to try to make it as a freelance writer. At the time, I was more like a freelance social media manager and wanted to transition to long-form content like blog posts and ebooks.

I signed up for Kaleigh Moore’s 1:1 freelance writing coach program and she helped me figure out my strengths and interests as a writer, which led me to content. It was one of the best decisions I made for my career hands down!

From there, I started working with B2B SaaS and ecommerce companies. I had the pleasure to write for companies like Stripe, Shopify, Loom, and RingCentral. Now, I’m working in-house on the content team at Shogun, which has been an incredible experience. We’re working on some really cool things in Q2, so stay tuned for that 😎

2. What's one marketing principle that you feel designers should use and vice versa (design principle for marketers)?

I think there’s a ton of overlap between what designers and content folks do at a super high-level. We’re both concerned with creating things that engage our audience and provide value in a way that isn’t too overwhelming.

The “how” and “what” varies between teams, of course, but we’re all focused on building the best asset for our audience.

I think both teams could benefit from asking the other more often, “What do you need for success? How can I support you to improve what you’re building?” Questions like this not only show that you want to better understand their goals and break down silos, but it can help your collective team ship something even better.

For more expert interviews, visit the Searchlight Content blog.