How to Hire a Diverse Team Of Rockstars In A Fast-growing Remote Startup—Interview with Pointed Copywriting

7 min

Before making the jump to freelance and eventually agency owner, Brittany Ryan traveled the globe as a production manager, hosting elite B2B events from Cannes to Australia’s Gold Coast.

But it wasn’t all sunshine and rainbows. After putting in time both on the corporate and freelance fronts, she spotted some real problems in the way teams operate. 

“I have loved every minute of my career so far, but when you’re working in a bigger organization, especially if you’re middle management, you can’t help but see how problems like red tape and rank pulling sneak into the culture,” says Brittany. “But when you move into freelance, you also see how many remote teams struggle to offer the right structure and support to their contractors, which can definitely impact quality of work.”

In her past life, Brittany Ryan produced high profile B2B events, recruiting star headliners like Bill Clinton, Paul Krugman, and Tony Blair.


Brittany was determined not to make the same mistakes in her own company. But like all things entrepreneurship, things always look easy until you roll up your sleeves and start executing. “There’s this misconception that remote teams are automatically diverse and inclusive, but unfortunately, that’s just not true.”

As owner and Content Chief of Pointed Copywriting, Brittany leads a small but mighty remote team of marketers, copywriters and content creators serving disruptive SaaS and B2B brands. 

They’re picky about who they work with—both on their client and team roster. Brittany knew that if she wanted to secure a steady stream of quality talent from all types of backgrounds, she’d need to revamp her recruitment process to stand out from the hundreds of other content agencies vying for top talent.

We caught up with Brittany and Pointed’s Content Lead Maddy Bartlett, to find out exactly how they focus on hiring a diverse, powerful team even when they’re strapped for time—here’s how it’s done.

Remote team culture: Don’t let complacency stop you from building your dream team

“At Pointed we’re all about providing high-quality copywriting and content strategy services for clients who actually care about how they impact the world. That’s why we’re committed to hiring people who add value to our team through different experiences and perspectives,” says Maddy Bartlett, Content Lead and pro wordsmith. 

Maddy has helped Brittany craft an intentionally diverse team of writers and editors. But inclusive recruiting wasn’t always as high a priority as it should have been.

“After seeing the problems in both corporate and remote work cultures and waking up to the devastating impact of systemic racism in 2016 after the murders of Philando Castile and Alton Sterling, I said that if I ever had the opportunity to build my own team, I would do it right—different perspectives from different people. Not everyone would look or sound just like me.”

But when it comes to the topic of racial justice, Brittany admits that white complacency is definitely a thing. (At least, it was for her.

“I’d gotten to a place where I’d become complacent—and not because I didn’t care, but because I was simply too damn busy to give our recruitment process the attention it deserved,” Brittany admits.

Today, the Pointed team has three writers and one editor (plus Brittany), based as far apart as the US, Nigeria, England, Russia and Cyprus. 🌎

“When you’re creating branded content, you’re effectively giving a voice to a business—which at the end of the day is just a group of people. And for that group of people, you are shaping their message, their core stance in the world. It’s a massive responsibility,” explains Brittany.

“I knew that by having a homogeneous team, we were missing out on important perspectives and opportunities, both for ourselves and our clients.”

So when she needed to bring on a new copywriter and team editor, she knew it was time to step back, take a breath and double down on amplifying diverse voices. “It feels so great to see that the diversity of the brands and readers we serve is finally reflected in the diversity of our team,” says Brittany.

How to hire a diverse team for your remote business (when your to-do list just won’t quit)

“The copywriting world is a competitive place,” says Maddy, “We get a lot of prospective candidates coming through and it can be hard to manage with such a small team—especially when you wear all these different hats. In our last hiring round we had 300+ applicants, and we get plenty through even when our roles are closed.” 

And it’s no surprise so many people apply.

“We’re a very intentional team,” says Brittany, “We have strong values we stick by no matter what. There are over 30 million bloggers in the world. Volume isn’t a problem but finding quality writers is a huge challenge in our industry. I don’t want to say that we’ve been able to attract great writers simply by doing the right thing but yeah, it kinda is that way.” 

When Brittany wrote her first job description for Pointed, she was crystal clear about the qualifications that really matter. 💎

Here’s what she always (and NEVER) puts into her job ads at Pointed.

  • Info about the company - Keep it clear and fun, no fluff.
  • Info about the candidate - Add an ‘About You’ section to help paint a picture of what excelling in the role looks like.
  • Key outcomes - Make sure these are the same criteria you use to measure team performance.
  • Responsibilities - Keep it short and focused on the core tasks that matter most.
  • Perks - Doesn’t matter if you don’t have a snack-packed office kitchen, focus on differentiating wherever you can.
  • EEO Statement - Don’t rely on boilerplate legalese for this. Be honest and open about why you want diversity for your business.
  • Compensation - Be as clear and straightforward as possible.

The team at Pointed is honest about who they are. As a boutique agency, they can’t afford to offer fancy wellness stipends or 401Ks. But they can offer a level of support, coaching and autonomy other, larger agencies simply can’t deliver.

“We get a lot of people applying who say, ‘I had to apply when I saw your diversity statement’. One candidate emailed us and said, ‘I’ve never felt so seen by a job ad before’, and that’s a huge win for us,” says Maddy. 

“One candidate emailed us and said, ‘I’ve never felt so seen by a job ad before’. That’s a huge win for us.”

Maddy Bartlett, Content Lead, Pointed Copywriting

Yet for many companies, diversity fatigue is a real issue. From employee resistance to lack of time and resources, there are tangible reasons why D&I initiatives fail

But for Pointed, failure is not an option.

Because, despite 87% of global businesses agreeing D&I is an organizational priority, Black unemployment is on the rise, women continue to lose out to men, and stories about workplace discrimination against the LGBTQ+ community are still common.

So how does Pointed successfully hire diverse candidates for their remote team, despite the avalanche of candidates and neverending to-do lists?

“It’s been a learning curve,” says Brittany, “And we’re by no means perfect—we know there’s a long way to go. But the first step is being open about what we want to achieve. We live in a biased world, so it’s important to us to lay our cards on the table and say, ‘This is what we believe.’”

Here’s how Brittany and Maddy changed Pointed’s team demographics from being 100% female, white, US and UK-based and straight to including team members from underrepresented communities all over the world.

Here’s what the 5-person team’s diversity stats look like now:

  • Gender: 60% male, 40% female
  • Race: 60% white, 40% Black
  • Nationality & Ethnicity: 60% US and UK, 40% other nationalities
  • Sexual Orientation & Gender Identity: 100% straight and cis-gender
By being transparent about this process now, we’re setting the bar for what team growth at Pointed should look like moving forward.”

Brittany Ryan, Founder & Content Chief, Pointed Copywriting

“We’re not perfect, but one of the first things you learn as a white person trying to stand in solidarity with folks from underrepresented communities is that there is no such thing as ‘perfect’ when it comes to the fight for equality. But that doesn’t mean you should stop trying to do the absolute best you can. By being transparent about this process now, we’re setting the bar for what team growth at Pointed should look like moving forward,” Brittany explains.

Stage 1: Proactively source diverse candidates

Finding great talent is about more than letting candidates come to you—for Brittany and Maddy, it’s about getting out there and finding the talent you really want.

But their hiring process hasn’t always been so proactive. When Pointed first started out, their approach was pretty traditional—LinkedIn posts and Upwork shout-outs got a solid number of applicants.

“We’ve never had a problem with candidates applying for roles—we get a steady stream through our careers page, LinkedIn and job boards, and often they’re good quality,” explains Brittany, “But we realized pretty quickly that wasn’t going to get us the diverse talent we wanted.”

They knew they needed to step up and make time to find the right talent.

“We’re always on the lookout for top talent now. We hit LinkedIn, Google and Breezy’s talent search, plus we always check out the authors of powerful words online,” says Maddy, “At first it felt like an extra task, but now it comes naturally. When we find diverse talent we love, we use the Chrome extension to pull their details into our candidate pools on Breezy and ping them an automatic email to gush about their work so that we’re on their radar too.”


Breezy’s Talent Search feature makes it easy to screen for the candidates you want.


“We’ve found some incredible talent through proactive sourcing,” adds Brittany, “It’s an awesome way to be super intentional about your hiring and actively pursue people from diverse backgrounds.”

Only once they’ve sourced a rich pool of diverse talent do they post a job ad. 

“We use Breezy’s free job posting to promote our job ads, and we always check the top diversity job boards too,” says Maddy, “The wording we use is super important. We’re very open about our diversity values, and we always use fluff-free inclusive language.”

Stage 1 Recap: 

  • Get everyone on the same page about what you’re looking for in an ideal candidate
  • Use LinkedIn, Google and Breezy Talent Search to dig for top diverse talent
  • Add potential candidates to Breezy’s Candidate Pools
  • Automatically email top talent to make sure you’re on their radar
  • Create a job ad that shouts about your diversity values and uses inclusive language
  • Promote job ads via Breezy’s free job posting feature and the top diversity job boards

Stage 2: Get some objective eyes on your brand

You can proactively approach as many diverse candidates as you can find online, but if they search your website or company LinkedIn page and don’t immediately see themselves in your brand, they’re not going to want to work with you. 

It’s as simple as that.

“I’ll never forget logging into LinkedIn the day after George Floyd was murdered and searching the hashtag, #BlackLivesMatter. I didn’t see a single post pop up. I couldn’t believe it. Why was the business community so afraid to speak up?”

Brittany and her team had recently spent a string of sleepless nights writing rush content to help their clients (and their client’s clients) navigate the coronavirus pandemic.

“I wrote about why I believe brands should openly address systemic racism with the same weight and gravity as the coronavirus crisis. But the truth is, I knew most brands weren’t speaking up because they were afraid of saying the wrong thing.”

Brittany had the same fears. So, she did what any proactive team leader would do and enlisted the help of an expert.

“I enrolled in Azia Ellis-Singleton’s interactive online course The Business of Race and all I can say is that it was a total game-changer. Azia really helped me understand how to bridge the gap between my intention as a business owner and the perception of our brand to other people,” says Brittany.


If you’re sourcing candidates via LinkedIn, why not take 5 minutes to update your company page with diverse imagery as a simple way to let candidates know all are welcome?

Azia reviewed Pointed’s website, careers page, company values and LinkedIn page and helped identify areas for improvement such as:

  • Using diverse imagery (using representative stock photos from places like nappy.co, Pexels, Unsplash and the Leanin Collection.)
  • Revamping luke warm values and messaging
  • Aiming for a better balance of business and human topics in our content messaging

But beyond nailing the image, Azia gave Brittany some crucial advice for walking the walk where it really counts: in her day-to-day interactions with the team.

“I think my biggest takeaway from working with Azia was that we’re not always going to get it right, but we must always be transparent about how we’re trying—the exact steps we’re taking to move forward. She reminded me to never let my team wonder what we’re doing in this area. Step up and let them know.”

Stage 2 Recap: 

  • Hire an expert to help review your brand
  • Update your company website, careers page and social media pages with diverse imagery
  • Assess your messaging to update and align with company values
  • Inform the team of the steps you’re taking

Stage 3: Choose the right tools to screen candidates

Once they’ve got a fresh pool of diverse talent lined up, it’s time to find the true copywriting heroes. 💪🏾

“We’re never going to use hidden words in a subject line or judge an applicant based on what font they’re using because at the end of the day, these things are fixable. It’s more important to us to make sure we’re not accidentally screening the right people out,” Maddy explains. 

“We’re all about a no BS approach to hiring, so we also skip the resumes—we don’t care where you went to school—for us, all that matters are two things: how well you write, and how you can add value to the team.”

Send automated candidate emails with Breezy questionnaires.

Here’s how the screening process works.

  1. Choose your tools wisely: The Pointed team uses Breezy questionnaires to easily create form templates. “Breezy’s questionnaires make screening really easy. We have a template set up that we can reuse and edit if we need to, so you don’t have to recreate it every time,” says Maddy.
  2. Use out-of-the-box questions to dig deep: “We try to add questions to dig deep with candidates,” explains Brittany, “We’ve just finished hiring for a Content Editor, where we asked candidates to tell us their best and worst editing quotes. It was a great way to find out about their editing style and how original they were.”
  3. Include a video assignment: “Recently we started using video assignments for roles that include client management, so we can check out candidate’s presentation skills. It also really helps pinpoint diverse candidates,” says Brittany.
  4. Create an automated response: Finally, they set up an automated ‘thank you’ email to all non-qualified applicants. 
“I did some deeper research into Pointed’s brand and mission and I loved how unapologetic they were. I knew it was the kind of team I wanted to be a part of.”

Jacob Pinkney, Editor-In-Chief, Pointed Copywriting

“We’re not big on titles and credentials, but when ace marketing consultant and Howard University grad, Jacob Pinkney popped into Breezy with a killer video pitch, we knew we needed to get him on the books for an interview asap,” laughs Brittany.

Stage 3 Recap: 

  • Use an automated questionnaire to get to know your candidates
  • Ask questions that dig deep and tell you more about candidates
  • Include a video assignment to check for presentation abilities and other soft skills
  • Create an automated 'thank you' to send all non-qualified applicants

Stage 4: Use a rating system to avoid hiring-fatigue

Next, Pointed’s two-person hiring team selects a small number of candidates to interview. 

“Once we’ve gone through and screened candidates, we use Breezy’s scorecards to rate them,” explains Maddy, “It’s easy to get hiring-fatigue when you have 200+ candidates, so we use a structured rating system to make sure our scores are always bias-free and based on the same thing.”

Here’s how their rating system works: 

  • ‘Very Good’: High-quality candidates who hit every must-have quality for the role.
  • ‘Good’: They have almost everything we want but lack one necessary quality for the role. 
  • ‘Neutral’: They have some good qualities but lack too many must-haves for the role.
  • ‘Poor’: Not good for the company in terms of tone, experience, etc.
  • ‘Very Poor’: The candidate’s misunderstood the job ad or the industry itself.
Breezy scorecards are a great way to record and share your thoughts on each candidate.

They then choose 2-3 candidates to interview, and take steps to minimize bias in the interview process

“I’d rather pick the top two and not get anyone, than sit through six interviews with candidates who I’m not 100% sure about,” says Brittany. 

“For me, it’s important to get the right person for the role, no matter how long it takes. We look for people with their finger on the pulse, and we always make sure to give extra airtime to people from diverse backgrounds.”

With a little help from Breezy, Maddy and Brittany were able to quickly comb through over 200 candidates and find the team’s stellar new editor in less than two weeks. 

And the process isn’t over once they’ve chosen their ideal candidate. 

“For all those ‘Good’ or ‘Very Good’ candidates that didn’t make the cut, the journey isn’t over. We add all our high-quality candidates to our Writers’ Pool in Breezy—so next time a relevant role comes up we can save time by making the most of the connections we have. We’re also working on a nurture campaign to make sure we stay on the radar of those top-quality candidates.”

With Breezy, Pointed’s two-person part-time hiring team can get back to over 200 candidates in less than an hour.

 Stage 4 Recap: 

  • Ask cultural, behavioral, leadership and self-awareness questions
  • Prioritize candidates from diverse backgrounds
  • Use a standardized rating system to reduce bias and hiring-fatigue
  • Choose only the top 2-3 candidates for interview to save time
  • Hold onto other top-quality candidates and nurture your relationship for future roles

Sounds great. But what does the team think?

We checked in with Moscow-based former IT pro turned copywriter Andrew Burmistrov for the full story.

Andrew joined Pointed in February, while the recruitment process was still very much a work in progress. 

“I was astonished by how quickly Pointed matured in terms of systems and processes within the 6 months I’ve worked here. This allowed us to keep doing the great work for our clients all the while saving resources and spending time on things that are no less important, yet often left out of scope: D&I, team wellbeing, and innovation,” says Andrew.

As someone who’s been in the remote-based freelance game for nearly 7 years, he’s not one to mince words about gig industry culture.

“The majority of content agencies and content teams I’ve worked with often build processes to maximize revenue and ROI, but at what cost? The quality of their work drops while their team health deteriorates. It’s like they’re slowly evolving into content mills while trying to keep their clients around by mimicking something they no longer are.”

“At Pointed, no matter what processes or systems we put in place to optimize our work, it’s never at the cost of our humanity. It’s like there some hidden ‘stay awesome’ filter that every initiative goes through before making it part of our workflow.”

The challenge now is to make sure that their systems continue to stay awesome as the business grows. It’s a massive goal. But with a little help from the right ATS, it’s definitely doable.

Diversity as a hiring human initiative

“Our hiring process is all about a great candidate experience. We see every candidate who applies as part of the team, even if they don’t work with us directly. Whenever someone sends their samples over we offer them a little tidbit of advice, and our new nurture campaign will go even further to help writers on their way,” says Brittany. 

Brittany and Maddy are in the process of establishing a nurture campaign that will help applicants who weren’t initially the right fit access training and resources that will help them advance their skills and secure better opportunities in the future by connecting them with talented team members like Dozie Anyaegbunam who runs an awesome free content marketing newsletter for ambitious writers and marketers.

“As a freelancer, it’s easy to feel like one more cog in the wheel. But with Pointed, it’s a totally different experience. Here you feel you are on a mission. The team always aims to get your buy-in, simply by being transparent and honest. You always feel heard,” says Dozie.

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