How Allyn Bailey and SmartRecruiters Succeeded with a Mascot and Marketing Savvy

SmartRecruiters doesn’t just want to help companies identify the right people; they’re interested in transforming the hiring process itself. The company’s platform combines automation and AI to streamline recruitment, helping organizations attract, select, and hire employees easily, effectively, efficiently, and, well, smartly.

Speaking of smart, we had the pleasure of talking to Allyn Bailey, SmartRecruiters’ senior director of brand experience and communication, about her multi-pronged campaign to challenge the status quo. Allyn discussed turning their AI co-pilot and semi-official mascot, Winston, into the centerpiece of a memorable, highly effective, low-budget marketing campaign. Read on to learn more about how scrappiness and storytelling combined to help the company grow its sales pipeline.

Q: Tell us about your role at SmartRecruiters and some of your market challenges.

Allyn Bailey

When I stepped into my role, the market was in a tough spot. There was a lot of growth in our space, but the buyer landscape had really narrowed. Companies had two options: go with a best-of-breed talent acquisition (TA) platform like ours, or default to the recruiting module inside their human capital management (HCM) suite.

But HCM tools were old, and most users didn’t love them. They were told to use them because the decision was coming down from the CFO level, not the TA team. 

We saw that as an opportunity. Our CEO, Rebecca Carr, decided to make a radical shift and rewrite how TA technology worked by creating a fully AI-driven platform. As our team built the platform from scratch, Rebecca turned to me and said, “I need you to convince the market that we know what the heck we’re doing. And I need you to make people believe we’ve already done it.” 

That’s the role I play. I take the vision and bring it to life for our customers and the market.

Q: Your mascot, Winston, is a cute little guy who played a huge part in that effort. Tell us about him and how he became so important to your marketing program.

Allyn Bailey

Winston was initially launched as an AI assistant designed to help hiring teams eliminate friction in the recruiting process. His reimagination, though, came from the creativity of Michael Stevens, our product marketing leader at the time, who was the real brainchild behind giving Winston his AI-first identity. We also worked closely with a brilliant agency team who helped refine Winston’s story and look, giving him the polish to match the bold vision behind him. 

We knew that if we were going to lead with an AI-first vision, we needed more than just features. We needed an identity, something that made the AI infrastructure approachable and accessible. We aimed to cut through the market noise with an emotional connection. So we leaned into this quirky, lovable creature and created an entire ethos around him. 

Once we did that, Winston became more than a mascot; he became the entry point into an insider experience. We invited media, analysts, and influencers into our company narrative. For instance, in our company kickoff, we gave select media raw, unfiltered interviews with our CEO and CPO, and even let our SVP of Engineering share how we were reimagining not just the product, but the way our teams worked. That transparency made people feel like insiders, part of the journey of a company in motion.

Q: You really used conferences and trade shows to your advantage. Talk a little about your event presence and how it played into the Winston campaign.

Allyn Bailey

We kicked things off at HR Tech with a “future is coming” theme. Instead of overspending on a huge booth, we limited the number of demos. We created a unique experience, including bringing in a fortune teller and handing out Winston-branded AI fortune cards. It was playful and a little weird in the best way. It sparked curiosity and framed the conversation: change is coming, and Winston is part of it.

We also made a deliberate bet to show up bigger than maybe even we should have at times, but that boldness was the point. Every live experience,  from the fortune teller to the speakeasy activations,  was polished and purposeful by design. That intentionality was critical to turning Winston from a quirky character into a driver of serious brand momentum.

Then we layered in exclusivity. At each event, we hosted behind-the-scenes speakeasies. Attendees needed a special invite to get in, which helped create buzz and made the whole thing feel like an inside experience. 

This evolved into our “Friends of Winston” program, which wasn’t just a fun club; it became the amplifier. Influencers, analysts, and insiders didn’t just repeat our story; they helped shape and spread it. Over time, everyone wanted to be part of it,  and in a way, everyone became a Friend of Winston. 

All of this led up to UNLEASH World in Paris, where we announced that Winston was landing. For two and a half weeks, we ran a tightly coordinated social campaign around his arrival. That announcement included a complete narrative arc: Winston had left Earth, had been reimagined as AI-first, and was now coming back to redefine recruiting.

Winston was everywhere, including on our swag, in our videos, and every campaign touchpoint. People connected with him immediately. They stopped by our booths just to get Winston stickers or pins. One person even asked if he had his own LinkedIn profile. And we didn’t spend a dime on celebrity influencers or over-polished creative. The real magic came from leaning into the character, letting our partners and community amplify him, and creating a sense of shared insider access.

Winston gave us a way to talk about innovation without sounding like everyone else. He turned our AI-first shift into a movement that felt tangible, fun, and collective. In a crowded, often sterile industry, that was exactly what we needed.

Q: What kind of results did you see from the Winston campaign?

Allyn Bailey

Since December, our pipeline has grown exponentially, week over week. We’re now sitting on the largest pipeline numbers in SmartRecruiters’ history, and our conversion rates have been strong too.

Q: What’s your advice for marketers who would like to emulate your success?

Allyn Bailey

Let your weirdest, boldest idea lead the way. For us, that was Winston. A literal sock puppet-like alien creature representing our AI. Sounds crazy on paper, but it worked because it made people smile and got them talking. That’s half the battle in B2B. If you can entertain and educate at the same time, you’ll win hearts and deals.

Also, scrappy doesn’t mean sloppy. It means knowing where your message hits hardest and doubling down there. If you can create something your audience genuinely wants to engage with, it doesn’t need to be expensive. It needs to be sharp, authentic, and memorable.

Want to enjoy Winston-levels of success in your marketing programs? Let REQ show you the way. Contact us today to learn how we can help.