In this episode of Bright Founders Talk, we sit down with Danika Chilibeck, an inspiring entrepreneur and the CEO and Co-Founder of Caddie AI. With a career that started in corporate finance and quickly transitioned into the tech world, Danika brings a unique perspective shaped by years at Shopify and Rewind.

From her early roles in operations to building a business from the ground up, her journey is a masterclass in adaptability and vision. It was during a remote work stint in Puerto Vallarta that she met her future co-founder and the idea for Caddie AI was born. What started as a remote tech community soon evolved into a global hiring marketplace, designed to solve one of the most pressing startup challenges: speed and flexibility in hiring.

Caddie AI connects employers with multiple headhunters simultaneously, significantly reducing time-to-hire without compromising on quality. In our conversation, Danika shares her firsthand frustrations with traditional recruiting and how they inspired a better, tech-powered solution. Her story is one of innovation, collaboration, and building smarter systems for the future of work.

From Beachside Brainstorm to Startup Breakthrough: How Danika Chilibeck Is Fixing the Hiring Game

Danika Chilibeck didn’t set out to disrupt the hiring industry while sipping coffee in Puerto Vallarta—but that’s exactly what happened. After years of climbing the tech ladder at companies like Shopify and Rewind, she found herself juggling remote work, operations leadership, and one too many hiring headaches. The breaking point came during a winter in Mexico, where a spontaneous knock on her door from a fellow remote tech worker sparked the idea that would eventually become Caddie AI. What started as a community project to help others land remote jobs evolved into a much bigger mission: fixing the messy, inefficient world of hiring.

“I was overseeing HR, hiring, recruitment—you name it,” Danika recalls. “One month we needed to fill 10 roles, the next month zero. It was chaos.” And while having internal recruiters helped, it just wasn’t scalable. She saw firsthand how traditional hiring systems crumbled under pressure. External agencies were expensive and inconsistent, often fading in enthusiasm after the first few weeks. Meanwhile, internal teams were stretched thin, battling for prioritization with every new vacancy. The result? Bottlenecks, frustration, and way too much time wasted just trying to find the right people.

Danika knew there had to be a better way. That’s where Caddie AI stepped in—built to solve one clear pain point: speed. The platform connects employers to multiple headhunters at once, speeding up the process and cutting down on that dreaded “time to hire” metric. And it’s not just faster—it’s smarter. With automations, Slack integrations, and vetted networks, Caddie aims to give time-strapped founders and hiring managers their most precious resource back. As Danika puts it simply, “It’s all about speed and giving you back time.”

From AI Overload to Product-Market Fit: How Danika Turned a Pivot Nightmare into a Recruiting Win

When Danika and her team first launched their product, it was riding the AI wave hard. The idea? An AI sourcing agent that would handle the top-of-funnel recruiting work—basically reaching out to potential candidates so humans didn’t have to. It made sense on paper, especially for someone obsessed with automation. But once it hit the real world, cracks showed fast. Candidates were skeptical, the tool felt cold, and, as Danika puts it, “AI just isn’t at the point where it can replace a human completely.” They had some users, but no one was truly in love with the product. What followed was months of chaos, pivots, and even a brief stint as a full-service recruiting agency just to stay afloat.

Finding product-market fit wasn’t magic—it was messy. Danika got real advice from a fellow founder: stop pitching, start listening. Instead of trying to sell their idea, they asked prospects about their biggest hiring pain points. That’s when everything clicked. Time-to-fill kept coming up as the core issue. Not flashy features. Not futuristic tech. Just the need to hire great people—fast. They spoke with over 50 hiring managers, dug deep into the emotions behind their bottlenecks, and ignored all the “helpful” product suggestions. The answer wasn’t an AI agent. It was a flexible, efficient hiring marketplace that helped recruiters and companies connect faster, without fluff.

These days, Caddie AI is seeing real traction—and not because it screams "AI" from the rooftops. Instead, it quietly uses AI in the background to supercharge human recruiters. Whether it's flagging potential candidate mismatches, summarizing interview calls, or surfacing top talent in a headhunter’s own network, the tech serves the people—not the other way around. Internally, Danika’s rule of thumb is simple: automate until it stops working. “There’s always a point where you need to bring a human in,” she says. That balanced approach—equal parts efficiency nerd and people-first leader—is what turned a flailing product into one that practically sells itself.

Rethinking Hiring: Why Resumes Still Matter and Local-Only Talent Pools Are Holding You Back

While the world rushes to automate everything, Danika isn’t so quick to bury the traditional resume just yet. Sure, we've got LinkedIn, GitHub, portfolios, even social media footprints—but hiring managers still want that one-pager. “Every hiring manager still asks for the resume. I’m surprised too,” she laughs. Despite all the tech and tools, the resume remains the go-to snapshot for understanding who someone really is. But that doesn’t mean the hiring process itself isn’t overdue for an upgrade—especially when founders are stuck wading through a flood of AI-optimized applications and unrealistic expectations.

Danika sees it all the time: early-stage founders thinking they’ll just post a job, snap their fingers, and boom—unicorn hire. In reality? Not even close. With AI flooding inboxes with thousands of resumes overnight, founders barely get through the first 50 applications before tapping out. “It becomes a game of luck,” Danika says. She also warns against relying solely on referrals or limiting your search to one city. Talent is everywhere, and sticking to local-only hiring is not just outdated—it’s expensive. A junior engineer in San Francisco could cost you as much as a senior in Eastern Europe. Why box yourself in?

At Caddie, Danika and her team practice what they preach—working across time zones and continents to find the best talent, not just the closest. They track real metrics to measure success: time to hire, candidate retention, approval rates from clients. Internally, they watch funnel conversion, new customer onboarding, and lead growth—but the ultimate focus is product love. “We want people to be so happy they’d recommend us to a friend,” she says, pointing to their target NPS score. For Danika, success isn’t about sticking to outdated norms—it’s about building a platform people actually want to use, one that makes hiring smarter, faster, and genuinely better.

The Future of Work Is Freelance: Why Danika Believes Millionaire Recruiters Are Coming

For Danika, one of the most exciting trends in the hiring space isn’t just about tech—it’s about people taking control of their careers. She’s seeing a growing wave of recruiters ditch the 9-to-5 grind to become independent freelancers, and platforms like Caddie are making that jump not just possible but profitable. “One of our headhunters in Argentina made almost a year’s salary from a single role,” Danika shared, still in awe. With tech layoffs shaking up the industry, more people are choosing autonomy, flexibility, and earning potential over corporate security. And Danika? She’s all in—waiting for the day when a recruiter becomes a millionaire through Caddie alone.

But while the gig-style future looks bright, scaling a people-first platform comes with its own set of puzzles. Danika knows the classic marketplace dilemma—matching supply with demand—is no joke. Onboarding a big-name client or two could easily 10x their active job listings overnight, and Caddie needs to be ready. So far, they’ve been hands-on with every recruiter and employer, chatting through Slack and building relationships in real time. But what happens when they hit thousands of users on both sides? “We’re going to get there,” she says confidently, “but it’ll come with its own set of challenges.”

When asked what advice she’d give to first-time founders, Danika doesn’t reach for a buzzword-filled answer. Instead, she gets personal. She credits her co-founder Delaney not just for being insanely talented, but for being someone she genuinely loves building with. “Find someone you enjoy doing life with,” she says. Forget obsessing over perfect complementary skills—alignment in values, trust, and having someone who stays calm when things get messy matters more. It’s that partnership, more than any tech stack or market trend, that keeps her grounded through the highs and lows of startup life.