If you’re reading this, you’ve probably felt the frustration of trying to book meetings with decision-makers in today’s world. It’s a grind, and the barriers keep stacking up. I’ve been in some form of sales for most of my career, and while the tools have changed, the core challenge remains the same: how do we get in front of the right people?

Years ago, you could cold-call your way into a meeting. I remember days when dialing 50 numbers meant 10 good conversations and a few promising leads. Today, good luck getting anyone to pick up the phone. Most calls go straight to voicemail, and even when you do connect, you’re often redirected to someone who’s “not the right person.” Email, once a sales lifeline, is another story. Getting a message into a decision-maker’s inbox—let alone getting them to respond—is harder than ever thanks to advanced spam filters and inbox overload.

Even when you break through, the simple act of securing a meeting can feel impossible. Decision-makers are busier, their calendars are fuller, and they’ve grown more skeptical of unsolicited outreach. The question isn’t just how to reach them; it’s how to build enough trust to get them to say yes to 30 minutes of their time.

Why It’s Harder Than Ever to Book Demos

1. Decision-Makers Are Harder to Access
Let’s start with the obvious: decision-makers are incredibly difficult to reach. Voicemails are the norm, calls are screened, and assistants or gatekeepers are more adept than ever at filtering out anything that looks like sales outreach. Even LinkedIn, which was once a goldmine for connecting with prospects, has become saturated with pitches. Many decision-makers have grown weary of the constant outreach and now guard their availability more closely.

2. Email Barriers Keep Rising
Email has been a go-to channel for years, but getting through is no longer a given. Advanced spam filters flag cold outreach as suspicious, even if your messaging is well-crafted. On top of that, decision-makers are inundated with hundreds of emails daily. Unless your subject line and content immediately stand out, there’s a good chance your email won’t be seen at all.

3. Reluctance to Meet
Even when you do connect, getting someone to commit to a meeting is a bigger hurdle than it used to be. The rise of remote work and Zoom fatigue has made people less inclined to add yet another call to their day. In-person meetings, which once offered a chance to build rapport, are increasingly rare. As a result, it’s harder to establish the trust and connection that make someone say, “Sure, I’ll give you 30 minutes.”

4. Trust Is Harder to Build
Decision-makers are more skeptical of unsolicited outreach than ever before. They’ve grown cautious after years of overpromises and irrelevant pitches. Building trust now requires more than persistence—it takes consistent, value-driven engagement over time. That means your messaging needs to deliver real insight or value, not just another “check-in.”

A Case Study in Breaking Through

Let me share an example from a client we worked with recently—a mid-sized SaaS company specializing in compliance software. They were struggling to reach key decision-makers at large enterprises. Their emails were getting blocked by spam filters, and their cold calls weren’t being returned. Frustrated, they turned to Roister to find a solution.

The first thing we did was refine their Ideal Customer Profile (ICP) to focus on roles and industries where their solution delivered the highest value. We expanded the ICP to include company and decision makers’ achievements and milestones that could be called out in a personalized, one-to-one email. Then we deployed our AI-powered ICP Data Agents to build a validated prospect list with accurate contact details and role-specific insights. This included identifying middle managers who could act as internal advocates and open doors to higher-level decision-makers.

Using this data, our Messaging Agents crafted highly personalized emails that spoke directly to the prospect’s challenges—things like navigating compliance regulations or reducing audit risks. These messages weren’t generic; they referenced specific issues the company was likely facing based on industry trends. Within three months, the client saw a 40% increase in booked meetings, including several with senior executives they’d been trying to reach for months.

How Roister Tackles These Challenges

These problems aren’t unique to one company—they’re the new reality for everyone in B2B sales. That’s why we’ve designed Roister’s solutions to address them head-on:

• Breaking Through Barriers: Our Data Agents ensure every prospect list is accurate and validated, minimizing bounce rates and improving deliverability. Messaging Agents craft one-to-one emails that avoid spam triggers and stand out in crowded inboxes.
• Navigating Complex Organizations: By analyzing organizational hierarchies, we identify not only decision-makers but also influencers and advocates who can help move the conversation forward.
• Building Trust at Scale: Trust takes time, and our agents are designed to foster it through consistent, value-driven messaging. Whether it’s sharing insights, offering useful content, or addressing specific challenges, the focus is always on creating meaningful engagement.
• Personalization at Scale: Combining AI with human oversight allows us to tailor outreach to each prospect without sacrificing efficiency. This means every message feels personal, even when targeting hundreds of leads.

Moving Forward

Reaching decision-makers isn’t impossible, but it does require adapting to a new reality. In my next article, I’ll share practical strategies we’ve used to navigate these challenges, including how to optimize multi-channel outreach and write messages that actually get responses.

For now, I’d love to hear from you: what’s been your biggest challenge in booking demos lately? Let’s share insights in the comments and learn from each other. Feel free to pass this along to your colleagues who are tackling the same obstacles.

About Rob Craig

Rob Craig has built a career on breaking into new markets and driving SaaS growth in B2B sales. As the founder of Roister, he combines decades of experience with cutting-edge AI tools to help businesses connect with decision-makers and build lasting relationships.