Case Study: How High Five 5x’d Their Meeting Conversion Rates with a New Outbound Playbook

Introduction

High Five is a tech recruitment and Employer of Record service provider on a mission to help companies hire top-tier talent across Southeast Asia. Their ideal customers are Founders, CTOs, and HR/Talent Acquisition leaders at tech companies (10-200 employees) that are actively hiring, recently funded, or have new leadership.

Like many early-stage startups, the initial go-to-market strategy heavily relied on cold outbound to build a customer base. However, the team quickly discovered that their initial approach was not only ineffective but was actively burning valuable leads.

The Challenge: Spray and Pray, and Getting No Replies

In the early days, High Five’s outbound strategy was a classic numbers game. The process involved:

• Generic Templates: A single, one-size-fits-all message was sent to hundreds of prospects at a time.
• Lack of Personalization: Messages used basic tags like [First Name] but lacked any genuine, individual research.
• Product-Focused Pitching: The emails focused entirely on High Five’s service, not the prospect’s problems.

Here’s an example of what their old outreach looked like:

“Hi Matt,

Glad to be connected with you here. I love what you’re building at [company name].

I founded High Five – a company that provides tech recruitment, Employer of Record and payroll services. Our mission is to help companies find top-tier talent across Southeast Asia.

If you’re hiring, please use this meeting booking link to find a time with me: [meeting booking link url].

Looking forward to chatting!”

The result? A conversion rate of nearly 0%. The team was spending countless hours on outreach with nothing to show for it – no replies, no meetings, and no pipeline. It was a demoralizing cycle that wasted precious time and resources, forcing the founders to question the viability of their entire GTM strategy.

The Solution: A Shift from Volume to Value

Realizing the old method was broken, the High Five team went back to the drawing board. They abandoned the “spray and pray” model in favor of a highly personalized, value-driven approach built on a few key pillars:

1. Targeting High-Intent Leads: Before writing a single message, the team built a highly curated list. For them, “high-intent” meant finding companies with clear buying signals:
   • Are they hiring now? They crawled job boards to find companies actively looking for talent.
   • Were they recently funded? They used a subscription to Crunchbase to identify companies with fresh capital.
   • Do they have new leadership? They used LinkedIn Sales Navigator to find companies undergoing strategic shifts.
2. Multi-Channel Outreach: The team engaged prospects on both LinkedIn and email to increase their chances of starting a conversation. They used tools like Apollo.io to find accurate contact information and email addresses.
3. Deep Personalization: Every message began with a unique, genuine compliment or observation based on the prospect’s recent LinkedIn activity, company news, or public interviews.
4. Focusing on Pain: Instead of pitching features, the team led with a clear understanding of the prospect’s primary pain points, using language that resonated with their specific challenges.
5. A Compelling Offer: The meeting request was replaced with a high-value, no-brainer offer, such as a custom audit or a mini-playbook, providing immediate value for free.
6. Specific Social Proof: Vague claims were replaced with concrete results, such as, “We helped a similar company increase their pipeline by 250% in 60 days.”

Here’s an example of their new, effective outreach:

“Hi Matt,

It’s great to see [company name] is growing so fast. I’m a big believer in the [company space] space, not just in Singapore but globally too. What do you think about [key insight]?

I’m reaching out because I saw that [company name] is hiring a [role].

It just so happens that the company I founded, High Five, specializes in filling this exact role. We’ve helped companies like [company A] hire for a similar role in less than 30 days.

On pricing, we’re doing things a bit differently, we won’t charge you any upfront fees for recruitment as long as you allow us to be your Employer of Record.

If this sounds interesting to you, I’d love to show you 1-2 candidates we currently have that match your requirements.

Would you have 15-mins for me this week?”

This new playbook transformed outreach from a sales pitch into a helpful conversation starter.

The Results: A 5x Increase in Meetings Booked

By implementing this new strategy, High Five completely turned its outbound performance around. Within six months of implementation, the company saw:

• A 5x increase in conversion rates from email sent to a meeting booked. This translated to a jump from booking just 4 meetings a month to consistently booking over 20 meetings in a good month.
• A significant jump in positive reply rates, with prospects often thanking the team for the well-researched message.
• The creation of a predictable, scalable pipeline that has become a core pillar of their growth engine.

This systematic approach proved that cold outbound is far from dead, it just requires a more human, thoughtful, and value-driven strategy.