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37 Questions with Sierra Sessions

Originally published in July 2025

Sierra Sessions is someone you want in your corner. As an account supervisor at Block Club, she’s part strategist, part creative partner, and part client confidante—always bringing energy, clarity, and a solutions-first mindset to the table. Whether she’s collaborating on a brand launch, leveling up internal processes, or helping clients find new ways to connect with audiences, Sierra always shows up with thoughtfulness and heart.

When she’s not orchestrating seamless client experiences, you can find her journaling, throwing frisbees to her dog Sully, or playing rugby with her local women’s team. In this edition of 37 Questions (our twist on Vogue’s 73), Sierra shares her insights on embracing change, being a “procrastinating perfectionist”, and the power of kindness.

  1. What is your role at Block Club, and what does it entail?

    I would describe my job as being a trusted advisor and strategic partner to clients. As an account aficionado, I’m not only responsible for ensuring we’re set up to meet the mark internally, but that the work we’re identifying and delivering on aligns with our clients’ marketing objectives and overall business goals.

  2. Do you have any rituals that help you start the workday right?

    My non-negotiable before-work ritual involves waking up early, making the bed, at least an hour of movement at the gym, a functional (non-psychoactive) mushroom tincture, and journaling outside with hot coffee while I listen to birdsong and throw a frisbee for my dog Sully in the morning sun.

  3. What’s for breakfast?

    More of a brunch, but I usually eat something hearty and high in protein. Always includes eggs and some sort of leafy green. Definitely too much butter.

  4. What’s the most interesting thing on your to-do list today?

    I’m currently taking a course to learn more about how to use AI for problem solving and how it affects the role of marketers. There are some really cool masterclasses out there about leveraging AI and how to effectively incorporate it into daily work across verticals. Really makes the quote, “AI won’t take your job, but someone who knows how to use it will,” ring true.

  5. How did you end up in marketing? Was it always the plan?

    Not so much a predetermined plan as it was a natural evolution. I first developed my chops in client services by joining as the third person at a SaaS startup and solving problems in product management with creative and sometimes unconventional solutions, which required me to develop a deep understanding of consumer behavior, communication strategies, and market dynamics—all core elements of marketing. Once I learned to anticipate demand and promote solutions effectively, the transition to marketing was a natural progression.

  6. What’s something about your job that energizes or inspires you?

    That would be my professional evolution from a prescriptive, formulaic digital consultant into a creative thought partner. I love being able to help clients with their brand development in a more hands-on way—from identifying the need firsthand, collaborating with my internal team to make it happen, and then seeing that concept exist out in the wild (and watch it perform well) feels really energizing.

  7. What’s your silliest irrational fear?

    I believe all my fears are rational, but the silliest one is probably chickens. Don’t let one get near my Achilles tendon.

  8. What do you think makes a great client relationship?

    Being someone your client actually wants to work with! I’m a firm believer that you have to actually like the people you talk to every day, so finding things you can relate to each other about and cultivating trust means your client (and internal team) feels comfy reaching out to you for anything, which makes for efficiently run projects and a more fun work day, in my opinion.

  9. What’s a brand or public figure you admire for how they show up?

    I really like how Tonya Papanikolov, the founder and face of Rainbo (the tinctures I was talking about earlier), shares her knowledge about the benefits and science of mushrooms, how she’s positioned her brand through Instagram, her podcast, and her “reset” retreats, and the rate at which she’s (mostly organically) grown her company in about six years. I admire her dedication to making an impact through community initiatives like forest restoration, women’s empowerment, and funding for Indigenous communities, to name a few. She’s branched out her marketing tactics in ways that feel authentic and inspiring for a CEO today. Plus I like a little “woo” with my science and activism.

  10. Can you tell us about a city or destination that’s shaped you in some way?

    Wilmington, North Carolina! I moved here in late summer of 2021, all the way from Salt Lake City, Utah, to follow an inner-nudge (that turned into a yell) and buy my first house by the beach, and I can’t even express the ways in which I’ve grown with this place.

  11. What’s something that always makes you laugh at work?

    Seeing my colleagues’ responses to “watercooler topics” in Slack, which is basically just various questions Rachel submits that the Slackbot regurgitates. I love an inside joke.

  12. What’s your go-to productivity trick when you’re in a rut?

    Purge-writing/brain-dumping. Even when I think I have no solution and nothing to say, it’s my morning ritual to fill out at least one page in my journal. Almost every time, I will resolve a problem I’m having by dumping all my thoughts onto paper in time with my pen. We already have all the answers, but I think hearing them requires taking the time to slow down and listen, even if it comes a few days later. You can’t think faster than you can write.

  13. What’s one lesson you’ve carried with you from a past job?

    To let people, processes, and companies change. Working in this industry requires adaptability—not just to trends and technology but to cultural shifts, leadership, ways of working, personal developments, etc. Learning to become a more flexible person has not only helped me extend more grace to others while they navigate their own (personal or professional) shifts, but also to think outside of the box when things become stagnant. Growth and evolution rarely follow a straight line, so I’ve learned to meet (and even embrace) change with curiosity over resistance.

  14. What’s your favorite campaign (yours or someone else’s) of all time?

    Nike’s “Dream Crazier” campaign. I still think about it. As an avid feminist and athlete, the video and all around messaging addressing the gender gap and double standard in sports (and elsewhere) stuck with me. Such a powerful example of inclusive, emotionally resonant, and successful social media marketing.

  15. What’s one thing you’ve learned about yourself in the last year?

    I’ve very recently learned that I am a “procrastinating perfectionist.” I’ve just finished reading The Perfectionist’s Guide to Losing Control by Katherine Morgan Schafler and it was super empowering. I’ve been working to apply the lessons from the book to every facet of my life, and it feels both like celebrating my particularities and not waiting for a special occasion to light the nice candle anymore. I might not ever be able to decide on a paint color, but you can bet your bottom dollar I’ll help you achieve the highest quality output where it matters.

  16. How do you unwind after a long day?

    A non-negotiable ~2 mile neighborhood walk so Sully can sniff out the latest “hot goss” that other dogs leave behind on bushes and fire hydrants. Walks are to dogs as scrolling is to humans.

  17. What are you into outside of work right now—any hobbies or creative outlets?

    I play flanker on my local women’s rugby team, and I volunteer with a horse ranch that provides equine therapy to people with special needs. I’m also into strength training, camping, walking in nature, reading, cooking, and, most recently, gardening—but I’m not very good at it. Can’t wait to have a super sketchy salad in about two months.

  18. Do you have a favorite way to spend a Sunday?

    Usually house chores like groceries and mopping. Nothing beats a stocked fridge and clean floors.

  19. What’s the most adventurous or unexpected thing you’ve done?

    Sell all my belongings and move across the country with no plan and less than three months notice

  20. What’s a piece of advice that’s stuck with you?

    OMG, so many. The first to come to mind is the question, “how are we to treat others?” Ramana Maharshi says, “there are no others.” I really love the notion of people and experiences being reflections of your inner world.

  21. What’s something small that brings you a lot of joy lately?

    Might be the mushrooms talking (kidding), but I just love being outside in nature. I try to spend as much time as possible in the backyard or on the beach or in the forest—anywhere surrounded by trees or bodies of water!

  22. What’s a song, book, or show you can’t stop recommending?

    I’ve been loving the shows Shrinking, Hacks, Somebody Somewhere, and Love on the Spectrum lately. I have too many books. My top recent reads for personal development: Eastern Body, Western Mind by Anodea Judith, Braiding Sweetgrass by Robin Wall Kimmerer, All About Love by bell hooks, Women Who Run With Wolves (a classic) by Clarissa Pinkola Estés, plus a handful of fictional thrillers.

  23. Have you ever gone viral?

    Unfortunately, yes, about a decade ago…Google “Sierra Sessions grandma.” That very choice haircut of mine lives on the internet forever now, all because I love my grandma and didn’t have a private profile. Lessons were learned.

  24. What would you tell someone who wants to go viral?

    I only know how to do it accidentally. Otherwise, I’d probably tell them to just be themselves.

  25. Do you have any weird talents or party tricks?

    No, but Sully has about 15. He brings me a pair of sweats every morning on command (my personal favorite).

  26. What’s your go-to karaoke song (or car karaoke jam)?

    For karaoke, it’s usually some angsty-girl-rock like Joan Jett, Alanis, Blondie, Cranberries.. But in the car I’m singing every single song across multiple genres for the entire drive! LOL. I’m super fun on roadtrips.

  27. What’s your most-used emoji?

    The hug (love you) or the devil horns (rock on)

  28. What’s your comfort food (or favorite takeout order)?

    Grams’s homemade fried chicken, gravy, mashed ‘taters, and fresh, local corn

  29. What’s your favorite way to get inspired creatively?

    Be around other people. I tend to be a bit of a homebody, so when I find myself doing the same thing over and over or getting blocked, catching up with a friend or working at a coworking space and just hearing other peoples’ thoughts gets my wheels turning again.

  30. What advice would you give to someone just starting out in client services?

    Be yourself, own your mistakes, and try to learn something every day. Remember that nobody knows it all.

  31. How do you approach giving tough feedback—whether to a client or teammate?

    By being objective and taking any personal feelings out of it. I always try to look at a situation from the other person’s perspective and give the benefit of the doubt, but I always communicate where I’m at and how the work could be affected first.

  32. What’s something you’ve changed your mind about recently?

    Podcasts (and podcasters). I like them now.

  33. What’s a tool or platform you use every day and swear by?

    The Apple Notes app. I have notes dating back 5+ years. It pretty much contains every thought and to-do/grocery/invitation list and dream I’ve ever had.

  34. What’s a misconception people often have about your job?

    I think a lot of people assume that account managers are just PMs or people who only schedule meetings and build project timelines, but there’s a much more significant relationship-building, strategy, and business growth aspect that goes into this role.

  35. What’s a personality trait you’ve come to really value in teammates?

    Kindness. The people who are definitely the smartest ones in the room, yet they’re still able to learn from others or see a different way of doing things. I admire those who compliment other people on their accomplishments and give credit for their ideas without expecting anything. There’s no ego involved, and it really does feel like we’re working towards the same goal—like a true team—which has a ripple effect!

  36. What’s your ideal vacation vibe—packed itinerary or no plans at all?

    I like to have a general sense of what I’d like to do or see each day—like a hike or something active, a nice restaurant, etc—then tool around and go with the flow exploring for the rest of it.

  37. What’s a trend (in culture, design, or marketing) you’re loving right now?

    Responsible marketing practices like ethical AI, data privacy/GDPR, DEIB, and digital accessibility to name a few. I will always be passionate about creating a more just internet that not only bolsters a purpose-driven economy but works toward a hopefully climate-neutral and sustainable technical future for all.