Meet the Wailers

Leathers joined the team in 2020, making the jump from retail. A tip from her friend brought her to Widewail, and 4.5 years later, she leads the response team with energy, focus, and a healthy dose of humor.

Outside work, Leathers balances her busy role with cooking, gym sessions, and a love of the outdoors. “If I can blast whatever music I want and get choppin’, that is the best form of meditation I can imagine,” she says. She’s also a fan of live music, painting, reading, and following Liverpool (Up the Reds!). Around Burlington, she loves catching sunsets on the rocks of Oakledge Park and grabbing a bite at Zabby and Elf’s Stone Soup or Café Mamajuana.

At Widewail, Leathers oversees operations for a team that responds to thousands of reviews daily, making sure every response aligns with the client’s voice. She’s been surprised by how casual relationships and trust among colleagues boost productivity and creativity, proving that culture and efficiency can go hand in hand.

Her colleagues know her for dad jokes that outnumber most actual dads, a competitive streak at foosball, and a knack for keeping the team aligned and engaged. Leathers’s leadership blends precision with personality, making her someone everyone on the team can rely on—and enjoy working with.

Annie found Widewail on LinkedIn and decided to take a chance and apply. What followed has been a mix of creative problem-solving, remote camaraderie, and daily challenges that keep her on her toes.

Outside of work, Annie is deeply creative. She’s passionate about fiber arts, from sewing and crocheting to construction paper collages, and enjoys video games—particularly survival-style games that allow for customization. She also enjoys spending time with her dog and makes music, regularly playing the French horn and trombone, with an unusual fan club of crows who respond (sometimes) to her riffs.

At Widewail, Annie’s role is to respond to reviews with accuracy, timeliness, and personality. She thrives most when crafting responses to unusual or humorous customer comments. Even from a remote setup, she’s a connector: “You can message anyone on the team at any time and get a friendly response, like you walked up to them in real life,” she says. “It’s really cool how we’ve built a strong sense of camaraderie with very little face time.” For Annie, Widewail is a place where she can enjoy her work, support her team, and make each customer interaction count.

Claire’s path to Widewail started with a friend’s recommendation and a bit of good timing. After exploring new opportunities, she heard about an opening on the sales team, applied, and landed the role by the end of the week. She started as a BDR, sharpening her sales skills and learning the industry, and now supports clients as a Strategic Account Manager—helping them navigate each step of their journey.

Off the clock, Claire is all about ultimate frisbee, a sport she’s played since college. It keeps her active, allows her to travel, and builds community—qualities she carries into her professional life. She’s also a coffee aficionado, hopping between Burlington spots like Zero Gravity, Specs in Winooski, and Scout Coffee whenever she needs a productive work session or just a moment to recharge.

What sets Claire apart is her combination of high drive and collaborative spirit. “I have never been on a team where everyone works hard and supports each other like this,” she says. She brings the same energy to her clients, helping everyone succeed while maintaining a personal touch. 

Ellie grew up in Southern Vermont and earned her English degree from UVM. After graduation, a tip from her friend led her to apply for an opening on the Response team, and she’s been part of it ever since. Now based in New York City, she continues to bring thoughtfulness and creativity to her role.

Outside of work, Ellie is deeply creative and community-minded. She is a jazz musician, actor, and community organizer, bringing people together through art, education, and mutual aid. She thrives on collaboration and loves projects that blend creativity with connection. When she’s looking for a local favorite, Pho Hong is her go-to spot for delicious, affordable food in Burlington.

At Widewail, Ellie serves as the Response Operations Lead, acting as the go-to person for overseeing the team’s day-to-day. She ensures workflows run smoothly, supports team members, and keeps operations aligned and efficient. She’s drawn to Widewail’s supportive culture, where team members are encouraged to pursue their passions and share their skills.

Her coworkers know her for quick wit in Slack, creative energy, and her wide-ranging experiences—from fruit farming in the desert to working in a castle in the French countryside—that make her perspective unique. Ellie’s approach to work blends focus with curiosity; she aims to start the day early, power through tasks, and take a midday recharge to stay sharp.

Ellie sums up her Widewail experience in three words: supportive, consistent, fun—a reflection of her role and the culture she helps sustain.

Originally from New Hampshire and a Burlington local for over a decade, Ian came to Widewail after moving from beer sales into tech via a software development bootcamp. LinkedIn and local networking brought him to the team, and he’s become an essential part of the Review Response crew ever since.

Outside of work, Ian keeps busy gaming, DJing, snowboarding, playing sports, making music, traveling with his wife, and exploring with his dog, Spruce. He also plays the trumpet—sometimes loudly, always memorably.

When asked about his role, Ian quips: “We are the engine that brings Widewail to life.” He jokes, but the point is real: he’s a part of the team that keeps things running smoothly. Standing at his desk with house music on, he handles reviews with focus, all while keeping things light for the team.

Ian enjoys the camaraderie at Widewail the most. Whether it’s making fun of Kyle in Slack or celebrating a Wailer softball win, he balances humor with getting the work done. His colleagues know him for his jokes, easygoing attitude, and the way he keeps the day moving.

Ian sums up his Widewail experience in a few words: “Real good.”

Jackie joined Widewail after a friend let her know about an opening on the team. From the start, she felt welcomed and part of a collaborative environment, and she’s been helping Widewail customers maintain their online presence ever since.

Outside work, Jackie enjoys yoga, writing poetry, and watching TV and movies. She’s also a fan of Burlington’s local spots—Cosmic Grind is her go-to for coffee, and Sarom’s Cafe in Winooski is perfect for authentic Vietnamese food.

At Widewail, Jackie prides herself on making sure that each review gets a thoughtful, on-brand response. She’s known by her coworkers for being kind, dependable, and steady—a presence that keeps the team aligned and supported. Quick with a helpful tip or a friendly nudge, Jackie makes it easier for everyone to stay focused and connected.

Jackie sums up her Widewail experience in a few words: supportive, engaging, and consistently enjoyable. She brings care and attention to every task, making her someone both clients and colleagues can count on.

Jessie joined Widewail in the summer of 2020 after the pandemic temporarily closed the restaurant where she worked. Originally applying for a role on the Review Response team, she shifted to Onboarding & Support, stepping into a role that would let her guide new customers through every stage of their journey—from signup and setup to training and post-launch support. “I think of our role as, essentially, holding our new customers’ hands and making sure they feel confident using our platform,” she says.

Staying active is a big part of Jessie’s life outside of work—walking, running, biking, hiking, and playing tennis with her dad. She also enjoys reading, recently finishing The Fire Next Time and starting Braiding Sweetgrass, and she brings that curiosity and attentiveness to her work.

What sets Jessie apart at Widewail is her commitment to quality and collaboration. She knows she can rely on her colleagues across departments to tackle complex customer issues, and she’s intentional about creating connections and community within the team. Her go-to productivity hacks—detailed Slack to-do lists, calendar blocks for deep focus, and quick mental refresh walks—keep her organized and responsive.

Jessie also values the small, human moments that make her work meaningful. Whether sharing updates with customers who ask about Vermont’s changing seasons or exchanging friendly banter with coworkers, she blends diligence with warmth, ensuring every interaction feels thoughtful and personal.

After college, Joe moved to Denver and built a career in financial services and fintech, eventually landing in Maine. When he and his wife had the chance to buy her grandmother’s house in Vermont, Joe discovered Widewail through some creative Googling. “I’ve always felt at home in the startup world,” he says, grateful for a role that welcomed him even though he came from outside the industry.

Outside of work, Joe keeps busy with tennis, skiing at Jay Peak or Middlebury Snow Bowl, and reading nonfiction—currently diving into the story of Henry Flagler’s railroad from Jacksonville to Key West. He also enjoys local adventures, from line dancing at Woodchuck Cider to sampling chocolate milk at Monument Farms Dairy, and taking the Amtrak round trip from Burlington when the mood strikes.

At Widewail, Joe is the bridge between clients and the internal team. “Customer says, ‘jump,’ I say, ‘how high?’ Then I check with the team, and together we make it happen,” he says. He sees that every request lands correctly, every voice is represented, and nothing falls through the cracks. 

Kyle came to Widewail after several years in sales, ready for a career change. A friend who had moved to the company encouraged him to reach out to the CEO—and shortly after, he joined the team. What drew him most? The flexibility to shape a role that fits his rhythm: autonomous, adaptable, and challenging enough to keep him engaged.

“I genuinely like and care about all the members of the response team,” Kyle says. Together, the team has built a role that’s both fun and reliable, balancing personality with precision in every client interaction.

Outside work, Kyle is an avid reader, with a particular fondness for Stephen King, Ray Bradbury, Shirley Jackson, Craig Davidson, and the like. He’s also a fan of Burlington’s local scene, from browsing the towering shelves at Speaking Volumes to grabbing a bite at May Day or Al’s French Fries.

At Widewail, Kyle keeps things moving with a system he calls “High-Intensity Interval Responding”: short, focused bursts of responses followed by a quick reset before diving back in. It’s a rhythm that keeps multiple client voices consistent while giving each interaction that personal touch.

Colleagues know him for his dedication and his humor, which blend into the energy he brings to the response team.

Luisa moved to Vermont from Venezuela soon after college, looking for a role that blended bilingual communication with customer service. “Widewail stood out from the start compared to other companies in the area, and joining the team has turned out to be one of the best career moves I’ve made so far,” she says.

She balances focused, independent work with plenty of collaboration. “It feels good to say my work directly impacts the voice of a business online and shows customers they’re valued. The mix of autonomy, positive culture, and collaboration is hard to beat.”

Outside the office, Luisa co-founded Hermanas Vermont, an affinity group that creates connection and support for Latinas in the region. “I love writing and bringing people together,” she says. On quieter days, she’s reading (currently reading The Rachel Incident), exploring Substack blogs, or heading to a craft or research workshop.

Her Burlington favorites include the Farmers Market in summer, Specs Café in Winooski for inventive drinks, and Santiago’s Cuban Cuisine for Caribbean flavors and lively service.

Random fact: she’s a self-described pop-culture sponge who grew up on early-2000s Disney and can still quote CSI: Miami. And if Shark Tank is on, don’t be surprised if she’s already picked the winner before the first pitch is over.

Luisa sums up her time at Widewail as “growth-oriented and community-driven,” a role where she can stay curious, stay connected, and see her work matter every day.

Meg’s journey to Widewail started with a forwarded LinkedIn post and a bit of curiosity. She began part-time, and nearly three years later, she’s an integral member of the response team, balancing focus, speed, and a sense of humor in every interaction.

Off the clock, Meg loves to be outdoors—soaking up sunshine whenever she can—but also loves curling up with a book at a local café or wandering around Church and Pine Street in Burlington. She’s currently pursuing a master’s degree in counseling, highlighting her passion for mental health and supporting others both professionally and personally.

At Widewail, Meg brings levity and positivity to her role, making her approachable for colleagues and clients alike. She tackles reviews with discipline and strategy: mornings are for rapid responses, while afternoons are reserved for deeper focus, and when things get heavy, she uses a 50-on/10-off rhythm to maintain consistency without burnout.

A Burlington local, Meg loves the Old North End’s hidden gems. Jake’s O.N.E. Market for coffee, May Day for a wine list worth savoring, and Taco Gordo for al pastor.

For Meg, Widewail is a space that balances intensity with ease. She sums up her experience as “easy-going, always-evolving, tons of perks,” and she’s proof that the people behind the service are just as important as the work they do.