Built a $1M+ Pipeline and Closed $100k+ Deals

Justin Sherlock is the founder of Caspian, an AI-powered trade advisory startup bringing modern automation to a legacy industry.

Before working with Windmill Growth, he barely touched LinkedIn — now it’s a core growth channel driving $1M+ in pipeline, multiple six-figure deals, and faster trust-building with enterprise buyers.

The Challenge

No content. No brand. No voice.
Before working with Windmill, Justin had never actively posted or built a personal brand. “I used LinkedIn for prospecting and hiring, but never for thought leadership. I wasn’t sharing ideas or showing expertise.”

An industry that demands trust.
In a complex, regulated space like customs and trade compliance, enterprise buyers need confidence — in the product and the people behind it. “We’re talking about compliance decisions made at the board level. If they don’t trust the founder, they don’t buy.”

A missed opportunity.
After raising their seed round, Justin wanted to amplify visibility and create scalable ways to demonstrate subject-matter authority — but lacked the process, creativity, and consistency to do it internally.

Why Windmill

• Fully-managed, end-to-end system. Justin didn’t want another DIY tool — he needed a partner to handle ideation, writing, posting, analytics, and audience targeting.
• Subject-matter depth. “We didn’t just post fluffy thoughts — Windmill helped me turn deeply technical topics into engaging, authoritative content.”
• Adaptive process & accountability. Even when early iterations missed the mark, Windmill quickly pivoted. “They didn’t dig in their heels. They listened, improved, built a more structured system — and results followed.”
• Embedded team. “It felt like having a growth team inside the company. They were in Slack, tracking metrics, running weekly check-ins, pushing me to show up.”

The Transformation

In just five to six months, LinkedIn became a strategic growth lever:

• 65%+ follower growth created visibility with the right audience and positioned Justin as a thought leader in a legacy space.
• $1M+ in pipeline is now directly linked to LinkedIn content — including several six-figure deals.
• Competitive edge. One major enterprise deal was won from a competitor because of Justin’s LinkedIn presence.
• Existing network re-activated. “It’s not just about new leads. Posting consistently re-engaged old contacts and turned dormant relationships into opportunities.”

The Takeaway

LinkedIn isn’t just a place to “build brand.” It’s a deal-making engine — if you treat it like one.

“Windmill became a trusted, embedded team focused on generating deal flow. They added structure, creativity, and accountability — and pushed me past founder impostor syndrome to show up consistently.”