How a Web Design Agency Made Back Their Investment in 3 Hours
From Freelancer to Agency Owner: Dimitri’s Journey
Dimitri Bilchenko, founder of Icebreaker Agency, began his professional journey as a solo freelancer on Upwork back in 2018. Like many others starting out in web development, he wore multiple hats — handling design, coding, sales, and client management. What set Dimitri apart early on was his commitment to niching down, focusing on WordPress development with a specialization in Elementor.
"I realized early that competing with everyone on everything just wouldn’t work. So we doubled down on Elementor. Clients looking for Elementor-specific expertise knew we were the safest option."
This decision paid off. Icebreaker Agency grew from a one-man freelancing gig into a lean agency offering white-label Elementor services to other agencies, along with direct project work for clients across industries.
"We provide design, development, and performance optimization — but always within the Elementor ecosystem. That’s how we became one of the most experienced agencies in this space.”
The agency’s name itself is rooted in Dimitri’s personal story. Inspired by a wedding toast comparing Dimitri and his wife to an icebreaker ship navigating through storms, the name “Icebreaker” symbolizes the company’s ability to help clients push through obstacles in their digital projects.
The Struggles of Manual Bidding on Upwork
While Icebreaker was growing steadily, Dimitri faced the typical growing pains of scaling an agency — and the biggest issue was manual bidding on Upwork. In the early years, he handled all the bidding himself, spending long hours filtering through jobs and crafting custom proposals. Over time, this became unsustainable.
"As a solo freelancer, manual bidding made sense. But once you start managing a team, handling projects, and trying to grow the agency, it just drains your time.”
To address this, Dimitri hired an SDR to take over the bidding process. However, new challenges arose:
- Inconsistent proposal quality.
- Poor lead qualification.
- Time delays in responding to leads.
“I still had to check my SDR’s work daily. The average reply time on proposals was around 72 hours, which killed momentum. Plus, not every proposal was written well — and some weren’t even for the right projects.”
The inefficiency was frustrating, especially given that Upwork remained Icebreaker’s primary acquisition channel.
“I was spending one to two hours a day cleaning up after my SDR. It felt like I was paying for a job I still had to do myself.”
Turning to GigRadar: Why Automation Was the Only Way Forward
Dimitri knew something had to change. Scaling an agency meant freeing himself from repetitive tasks. That’s when he discovered GigRadar, a tool designed to automate proposal submissions on Upwork.
"I instantly saw GigRadar as the missing piece — it looked like an Ads Manager for Upwork.”
One of Dimitri’s initial concerns was security, but after discussing with the GigRadar team and learning more about the platform’s compliance with Upwork’s policies, he moved forward. Within days of setup, the results were noticeable.
"I kept the SDR on board at first, just to be safe. But GigRadar outperformed him almost immediately — I was getting more qualified leads faster and with fewer mistakes.”
With customizable filters and automation flows, GigRadar allowed Dimitri to:
- Eliminate human error in job selection.
- Send personalized proposals automatically.
- Optimize lead generation without hiring additional staff.
"It’s not a push-button tool. You still need to know your niche, set your filters, and guide the process. But once you do, GigRadar takes care of the repetitive legwork.”
Results: Faster Lead Flow & Revenue Growth
Since integrating GigRadar, Icebreaker Agency has automated more than 3,500 proposals, significantly accelerating their sales pipeline.
“We’ve generated hundreds of thousands of dollars in revenue thanks to GigRadar — anywhere from $200K to $300K in total.”
Dimitri emphasizes that the key isn’t just about sending more proposals, but about sending better, faster, and more relevant ones. He estimates that GigRadar paid for itself within just a few hours after activation.
“I recouped the cost of the tool in literally hours. The ROI was insane.”
With the bidding process now automated, Dimitri personally focuses on closing deals and managing client communications, while the technical team handles project delivery. Automation has allowed him to reclaim control of his schedule and focus on scaling operations.
Insights for Agencies: Dimitri’s Tips for Upwork Success
Over the years, Dimitri has learned several key lessons about succeeding on Upwork — especially when running an agency.
“Upwork is a high-intent platform. Clients come to Upwork to hire. It’s not like LinkedIn or cold outreach, where you’re creating intent from scratch.”
Here are his top insights for agencies looking to grow:
1. Specialize and Stand Out
“I’ve A/B tested offering general services vs. niche services. Niching wins every time. Clients want experts, not generalists.”
For Icebreaker, focusing on Elementor allowed them to win over clients looking for specialized WordPress solutions, beating out competitors who offered broader but less focused services.
2. Speak Directly to Client Pain Points
“Your proposal should ‘speak’ to the client before they even meet you. Address their pain points clearly and show you’re the safest option.”
Generic proposals don’t convert — Dimitri ensures that every GigRadar-powered proposal aligns with client expectations and demonstrates deep understanding of the niche.
3. Leverage Automation Wisely
“GigRadar won’t close deals for you. It’s a tool — but a powerful one if you use it right.”
For Dimitri, automation isn’t about replacing sales conversations, but about removing inefficiencies in the bidding phase so human efforts can be focused on relationship-building and deal-closing.
4. Don’t Fear a Fresh Start on Upwork
For new agencies or freelancers with zero earnings on Upwork, Dimitri suggests starting with small, strategic wins.
"Offer a free trial or demo. Redesign a hero section or write demo content — whatever it takes to prove your value fast and build trust.”
Final Thoughts: Automation as a Competitive Advantage
Today, Icebreaker Agency continues to grow, thanks in part to a streamlined internal workflow powered by GigRadar. Dimitri no longer worries about lead generation slowing down operations — automation takes care of that.
“GigRadar allowed me to remove the bottleneck and focus on scaling the business. I’d recommend it to any agency serious about growing on Upwork.”
