Originally published in January 2025
Rachel Segal-Sklar has sharpened her writing skills across a range of different industries—spanning from fintech and AI to entertainment, cosmetics, and interior design. As a senior copywriter and content strategist at Block Club, she brings over two decades of marketing experience to our B2B tech clients, all with a creative flair that makes even the most complex topics clear and engaging.
When she’s not wowing our team with original song renditions at karaoke, Rachel can likely be found playing Homescapes, studying Spanish, or preparing an elaborate eggplant parmesan. Her dynamic personality shines through in this edition of 37 Questions—our twist on Vogue’s 73—where she shares her top tips for overcoming writer’s block, maximizing the value of content, and a whole lot more.
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What’s your favorite way to start the day?
Coffee. Lots of strong coffee. I am not a morning person!
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How long have you been writing for tech companies?
I entered the fintech space in 2021 at a banking-as-a-service (BaaS) company serving Latin America and the US. It was a great crash course into the industry!
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What other industries have you written for?
I’ve written for a wide variety of industries, including interior design, DTC cosmetics, executive leadership development, customer experience… the list goes on! But B2B SaaS and fintech are nearest and dearest to my heart.
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Where did you pick up your writing abilities?
As a kid, I absolutely loved reading. I think the combination of voracious reading and my weird imagination created the perfect storm to develop as a writer.
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What books were formative for you growing up?
So many! The Giver was an early one. I discovered Vonnegut in middle school, and that really shaped my worldview in a lot of ways.
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Can you give us an example of how your worldview was affected?
Vonnegut introduced me to a level of higher thinking that I wasn’t familiar with as a twelve-year-old. He was fiercely critical of war and capitalism and unchecked power and extremely empathetic toward humankind. And so, so funny.
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How do you help clients determine the right kind of content for them?
In most cases, there’s not just one “right” type of content. I think it’s important to choose content that supports your larger business goals and meets your audience where they are.
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How has your experience in content creation prepared you to meet the diverse needs of tech companies?
I’ve been on both large and small teams, so I’ve had very focused roles as well as broad ones where I’ve had to wear many hats. On the more focused side, I’ve developed and executed written content across channels, including video and podcast. On the broader side, I’ve created content strategies and led creative direction for both copy and design, as well as executing it all!
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Some business goals—like improving ROI—are relevant across industries. What strategies do you recommend for businesses to get the most value out of their content?
You can get the most out of your content by repurposing it into different formats. You could take a short blog post and turn the main points into a video; you could take the video and turn it into an infographic; you could take those main points from the infographic and turn them into talking points for a webinar; you could take the webinar discussion and turn it into a guide on the topic. You get the gist.
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Which elements or attributes make content binge-worthy to you?
If it’s narrative content, it has to be intriguing characters and cliffhangers. Intriguing doesn’t even necessarily mean well-developed. I can think of a handful of characters that are horribly under-developed but have a je ne sais quoi that hooks me—like reality TV stars or Che Diaz. The cliffhanger element is also essential to keep the momentum of a good binge going. The actual quality of the content is irrelevant.
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How do you know when a body of writing is finished?
Even if you’re not writing prose, the most effective writing has a narrative element to it. Decide what story you want to tell, and when you’ve explored it in full, you’re done.
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Do you have any tips for overcoming writer’s block?
Don’t push through alone! It’s usually helpful for me to talk things out with someone else, especially if there’s a certain element or point I’m stuck on. I’ve spent a lot of time trying to work through blocks mentally and alone, and it never works.
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What’s a skill you think all writers should have?
Writing is often thought of as a solitary process, but I think every writer should learn how to collaborate really well. It’s actually one of the most important aspects of the job for me, since being able to incorporate feedback from different types of stakeholders can make all the difference in a piece of content. It’s common that you’ll have to collaborate with other creatives, like designers, so it’s important to learn their language as well as knowing your own, so you can all create a coherent final product.
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What advice would you give to someone who is new to writing for B2B tech?
Lean into the human side of B2B. Try to imagine what excites you about tech. It probably excites other people, too!
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What’s the key to getting hired as a writer in tech?
As a creative of any kind, having a strong portfolio is key. As a writer, I try to think of every public piece of writing as my portfolio—from client work down to my LinkedIn profile or an email.
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What’s a fun trip you went on recently?
I hate to be one of those people who goes to Japan once and never shuts up about it, but that’s unfortunately who I’ve become. I went in October 2023, and I’m plotting my way back ASAP!
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Give us a fun fact about yourself.
I was once in the early stages of casting for an MTV reality show, but my life was too normal/drama-free to move forward.
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Name a hobby of yours that might surprise people.
Despite my recent travels to East Asia, every year since maybe 2020, my resolution has been to learn Spanish. I have spent hundreds of dollars for basic Spanish lessons I repeat over and over, so at this point you could call it a hobby. 😭
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Do you have any guilty pleasures?
Sure! I definitely have more than I can mention here, but my guiltiest is probably playing the mobile game Homescapes. I’m embarrassingly on level 11,586, so that should tell you how much time I’ve wasted on this game. If I were as dedicated to learning Spanish as I am to Homescapes, I would be fluent by now.
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If you could have any superpower, which would you pick?
Teleportation, hands down. I think about it all the time, including potential security measures like doorbells and passwords. I know they say life is all about the journey, but let’s be honest—most of the time you just wanna get where you’re going. It’s eco-friendly, too!
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What have you learned recently?
Radiatore is not a good pasta shape to cook risotto style. It gets mushy. Hard lesson to learn, since I’m a perfectionist not only about my writing, but also my cooking.
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Who do you admire?
People who live loudly and unapologetically, especially when it’s easier not to
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What excites you currently?
My roots are creative/comedy writing, and after a short stint in entertainment, I pivoted strongly away from writing for pleasure. These days, I’ve gotten back into it with a push from a friend whose novel I’m editing (also exciting!) and it’s been a really neat experience to get back to a place I haven’t been acquainted with in a decade.
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Is there a type of content you look forward to working on the most?
I love projects that allow me to tap deeply into my creativity and push boundaries or learn something new. That could be working in a new format, like podcasting, or coming up with taglines, or even working with designers on infographics.
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When do you know it’s time to leave your comfort zone?
It can be hard to put yourself out there, especially as a creative, but over the past decade-plus doing this work, I’ve probably gained the most confidence when I’ve gone outside of my comfort zone. I’ve worked in a handful of industries, with many different types of people, at companies of varying stages, and they’ve all helped me become a better teammate and writer. When you feel a strong aversion to something, it’s time to examine it. Usually, the scariest things are the most worth it.
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Name something you’d like to accomplish that is outlandish yet feasible in this lifetime.
Buying a two-bedroom apartment in my neighborhood in Brooklyn
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Do you plan on staying in Brooklyn for a while?
Until I’m priced out! But seriously, I grew up on the Upper West Side of Manhattan, and where I live now is just far enough away for it to feel novel.
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Name a recording artist you love.
To quote Sister Mary Clarence (played exquisitely by Whoopi Goldberg) in Sister Act 2, one of my favorite films of all time: “I’m what you call eclectic.” I like mostly everything!
But I will call out Moses Sumney here because he’s someone I saw perform at a party in LA back in 2013 and instantly knew he was going to make it. This was before a record deal, an album, anything. It’s been wild to see his trajectory over the past decade. He is such a rare talent and has a new EP out this year!
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What are you listening to right now?
I’ve had Beyonce’s Renaissance on repeat since it came out in 2022. I’ve also been listening to Chappell Roan and Charli XCX like everyone else since the summer! But I do also revisit well-loved albums like Be the Cowboy by Mitski and all of STRFKR’s catalog, along with more funky albums from Kaytranada and Toro y Moi.
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Do you have any hidden talents?
I kind of have a former hidden talent! I used to play the cello in middle school and was even in a quartet that won a competition. I also am quite familiar with the Harold structure of improv—I even used to host a weekly comedy show with my own indie improv team!
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What do you do to avoid burnout?
It’s so important to understand your own boundaries and stick to them. Most of the time, schedules can be shifted, priorities can be rearranged. You have to listen to yourself when you’re starting to burn out. Equally as important is communicating your needs to your team as soon as possible, so you can all problem-solve together. Something that can be hard to accept is people usually don’t know what you’re going through unless you explicitly tell them!
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What do you like to cook on a day off?
There’s a dish I really like to make occasionally that takes forever to make, so it’s good when you have nothing else to do. It’s a Claire Saffitz recipe for eggplant parmesan that’s assembled like a lasagna, and every component takes at least an hour to prepare. Two to three hours for the sauce; an hour to draw moisture from the eggplant; an hour to bread and assemble; an hour and twenty minutes to bake; and then you still have to wait thirty minutes for it to cool before eating. Truly an undertaking.
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Would you rather: a strict work routine or a flexible schedule?
A flexible schedule! I do appreciate routine, but it can get too tedious after a while. That’s why I love working at Block Club—no two days are the same!
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What’s the last movie you watched?
I have a Criterion channel subscription, and I love its 24/7 feed, which is how I’ve been discovering movies lately. The last film I caught was a Fellini short film called Toby Dammit, based on an Edgar Allen Poe story. A pretty unhinged, surrealist take on fame, performance, and Hell.
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Which movie are you most likely to force people to watch as they’re getting to know you?
I don’t think I’d have to force someone to watch a movie to get to know me when I could just show them the list of Nicolas Cage films my husband and I have watched over the course of a year and a half. The TV show Clone High was also formative for me as a middle schooler—my first tattoo is a Clone High tattoo! If you google “clone high tattoo,” mine is the first that pops up. 💅
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What’s a technology you couldn’t live without?
I know it’s a bit uncouth to say, but I very much have a screen addiction. I feel uneasy without my phone close at hand. But I do also feel nostalgic for the days when using computers was a hobby and cell phones were rare. I suppose some days I say burn it all down, and others I couldn’t bear to part with anything.
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What’s a goal you’re working towards this year?
Creo que ya lo sabes.