Articles

How We Booked 50+ B2B Meetings in 30 Days

Nov 27, 2025

Everyone's talking about how long B2B sales cycles have become, and they're right.

According to the Dentsu Superpowers 2025 study, buying decisions now take 54 days longer than they did a few years ago, with an average of 7.4 people involved in each deal. More stakeholders, more opinions, more delays.

But here's what's interesting: our team at Hey Sid has been doing the opposite.

Over the last month, we booked 50+ meetings in 30 days using Precision Connect. And importantly, we achieved this by following the same warm outreach structure we recommend to our customers, a system built on familiarity, relevance, and timing.

Here is what worked, and how it aligns with the way modern B2B buyers make decisions.

Familiarity Comes Before Outreach

The results started long before the first message was sent.

Instead of rushing into outreach, we began by making sure our ideal buyers had already seen and recognized our team. Our commercial team stayed active on LinkedIn by posting consistently, commenting on industry conversations, and showing up where our ICP spends time. Over time, prospects repeatedly saw our names and perspectives, which meant that outreach later on did not feel cold.

Once that familiarity began to build, we started sending personalized LinkedIn connection requests to the people who showed meaningful engagement. We did not pitch. We did not rush. The goal during this stage was simple: create recognition and ease prospects into our ecosystem naturally.

Familiarity is the foundation that makes everything else work.

Warm, Human Outreach on Their Timeline

After prospects had seen our activity and engagement on LinkedIn, we gradually introduced short, value-driven messages. These messages focused on insight or relevance, not selling. A few weeks later, we followed up with conversational check-ins. When interest appeared, we closed the loop with a concise, personalised message summarising value and offering a clear next step.

The timing mattered.

We did not try to push prospects from connect to meeting instantly. Instead, we allowed space for familiarity to develop so each touchpoint felt warm and intentional rather than abrupt or forced.

This rhythm consistently created real conversations and, eventually, meetings.

Experience Is the Shortcut to Trust

Strong buying experiences dramatically shorten sales cycles.

Dentsu highlights that brands with better buyer experiences see:

Sales cycles that are 27 percent shorter
Three times higher likelihood of increased customer spend
Significantly higher NPS scores

We saw the same effect. Thoughtful outreach led to faster replies and fewer touchpoints. Buyers immediately recognize automated messaging, but they also immediately sense when communication is genuine. When they feel respected and understood, the buying process accelerates.

Experience builds momentum, and momentum shortens cycles.

Relevance Outperforms Volume

We did not send thousands of messages.

We focused on a curated ICP list and used Precision Connect to identify who engaged, who replied, and who showed interest. With that visibility, we doubled down on what worked and ignored what did not.

Our best conversations came from messages rooted in real relevance.

A VP of Sales responded because we addressed challenges around slow deal cycles.

A CMO engaged because we highlighted the importance of familiarity in enterprise buying.

Shorter, tailored outreach consistently outperformed long, generic messaging.

Relevance is what earns the reply.

LinkedIn: The Channel Where Modern B2B Buying Happens

Almost 90 percent of our clients came directly from LinkedIn.

This reflects what we see across all B2B clients: buyers are active and reachable when approached in the right way.

Because prospects had already seen our team’s posts and engagement, our connection requests and messages did not feel cold. They felt familiar, credible, and aligned with what they had already observed. As visibility compounded, so did replies, interest, and meetings.

This was not automation.

It was human connection supported by precise targeting.

What We Learned

After using our own outreach system exactly as a customer would, several truths became clear:

• Personalization works when it is relevant
• Consistency outperforms volume
• LinkedIn is the strongest channel for building commercial relationships
• Experience shortens sales cycles because trust compounds
• Buyers move faster when they feel understood

Dentsu’s findings reinforce these patterns.

Modern B2B buyers reward brands that feel credible, familiar, and human.

The Hey Sid Takeaway

At Hey Sid, we did not just build an outreach tool.

We built a system.

Precision Connect enables teams to reach the right people at the right time with the right message while letting familiarity from organic activity do the heavy lifting.

The result is simple. More conversations. More meetings. Faster-moving deals.

Relevance builds trust.

Trust drives revenue.