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

How Justin Sherlock Closed Six-Figure Deals Thourgh LinkedIn GTM

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.

$1M+ in pipeline directly influenced by founder-led content
65%+ growth in LinkedIn follower base
Multiple six-figure deals closed with LinkedIn as a key factor
Stole deals from competitors due to stronger brand visibility
Built trust and credibility in a highly regulated, enterprise-focused industry

“We literally stole a six-figure deal from a competitor because the buyer saw me posting on LinkedIn. It wasn’t just brand — it changed who picked up the phone.”

Back to case studies

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

How Justin Sherlock Closed Six-Figure Deals Thourgh LinkedIn GTM

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.

$1M+ in pipeline directly influenced by founder-led content
65%+ growth in LinkedIn follower base
Multiple six-figure deals closed with LinkedIn as a key factor
Stole deals from competitors due to stronger brand visibility
Built trust and credibility in a highly regulated, enterprise-focused industry

“We literally stole a six-figure deal from a competitor because the buyer saw me posting on LinkedIn. It wasn’t just brand — it changed who picked up the phone.”

Back to case studies

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

How Justin Sherlock Closed Six-Figure Deals Thourgh LinkedIn GTM

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.

$1M+ in pipeline directly influenced by founder-led content
65%+ growth in LinkedIn follower base
Multiple six-figure deals closed with LinkedIn as a key factor
Stole deals from competitors due to stronger brand visibility
Built trust and credibility in a highly regulated, enterprise-focused industry

“We literally stole a six-figure deal from a competitor because the buyer saw me posting on LinkedIn. It wasn’t just brand — it changed who picked up the phone.”

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

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

How Justin Sherlock Closed Six-Figure Deals Thourgh LinkedIn GTM

How Justin Sherlock Closed Six-Figure Deals Thourgh LinkedIn GTM

Justin Sherlock

Co-Founder at Caspian

Justin Sherlock

Co-Founder at Caspian

Justin Sherlock

Co-Founder at Caspian

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.”


Metric

Before Windmill

After 5–6 Months

Follower Growth

Flat / inactive

+65%

Pipeline Influenced

< $250K

$1M+

LinkedIn Closed Deals

N/A

Multiple six-figure deals

Content Consistency

Irregular

Structured weekly cadence

Network Engagement

Passive

Active, inbound conversations


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.”

Unlock Your LinkedIn Potential!

Schedule a discovery call to explore how we can elevate your LinkedIn presence together.

Unlock Your LinkedIn Potential!

Schedule a discovery call to explore how we can elevate your LinkedIn presence together.

Unlock Your LinkedIn Potential!

Schedule a discovery call to explore how we can elevate your LinkedIn presence together.

Unlock Your LinkedIn Potential!

Schedule a discovery call to explore how we can elevate your LinkedIn presence together.