The “Messy Middle” Is Where B2B Growth Wins or Dies. Here’s How to Win It

By Ronan Keane

You’ve built a strong product. You’ve hit early traction. Maybe you’re at $5M+ ARR. But now, the growth curve is flattening, and it’s getting harder to forecast pipeline with confidence.

You’ve probably tried a few things: hired a growth marketer, tested paid channels, maybe even brought in an agency or doubled down on content. But the results feel random. Inconsistent. Hard to attribute. Pipeline panic starts creeping in.

Here’s the truth: It’s not just you. It’s not just your team. It’s not even just your strategy.

It’s your buyer. More specifically, it’s the unpredictable chaos they swim in every time they try to decide whether (and how) to buy from you.

Google calls this chaos the Messy Middle. And understanding it is the key to driving predictable growth for your B2B SaaS company.

Let’s break it down.

What Is the “Messy Middle”?

When someone in your target market encounters a need (the “trigger”), they don’t move in a neat line to purchase. They drop into a complex maze of digital exploration and evaluation.

Think: infinite tabs open. Slack pings from colleagues. Review sites. Analyst reports. Competitor pages. One minute they’re curious about a category. The next, they’re comparing feature sets. Then a webinar catches their eye. Then they loop back to the beginning.

Welcome to Internet Street. It’s open 24/7, bursting with options, opinions, and overwhelming choice.

The Messy Middle is that chaotic space between trigger and decision. Your ability to influence that middle zone, to show up, shape perceptions, and reduce decision friction, will determine whether you win or lose deals.

Why the Messy Middle Matters for B2B Growth

Most early-stage B2B SaaS companies still operate with a linear model in mind: awareness → interest → consideration → decision. Maybe with some nurture tracks sprinkled in.

But your buyer’s brain doesn’t work that way anymore.

Google’s research reveals two distinct mental modes in the Messy Middle:

• Exploration (adding options): They search, gather, consume.

• Evaluation (narrowing down): They compare, score, eliminate.

They loop between these modes repeatedly, often subconsciously. It’s messy. It’s non-linear. And it doesn’t fit into traditional funnels.

If your marketing and GTM strategy aren’t designed to influence both states, you’re leaking revenue.

The Six Biases That Drive Buying Decisions

This is where it gets even more interesting and actionable. Google, in partnership with The Behavioural Architects, identified six cognitive biases that heavily shape buying decisions in the Messy Middle:

1. Category Heuristics
   Shortcuts like “Top 10 software for X” or “G2’s #1 rated tool.” Simple claims can punch far above their weight.
   
   

2. Power of Now
   Faster equals better. Emphasizing quick ROI, instant setup, or same-day onboarding wins attention.
   
   

3. Social Proof
   Reviews, testimonials, customer logos, and case studies drive trust and urgency.
   
   

4. Scarcity Bias
   “Only 5 seats left at this price” still works, even in B2B. Limited-time offers can prompt action.
   
   

5. Authority Bias
   Third-party validation (Forrester Wave, Gartner, analyst quotes, industry influencers) builds credibility.
   
   

6. Power of Free
   Even in enterprise SaaS, freemium offers, free audits, or trials can reduce friction in early exploration.

Most B2B founders underutilize these. But they’re not gimmicks. They are hardwired human decision drivers.

So… How Do You Use This?

Let’s bring it back to your reality. You want predictable growth from $5M to $20M ARR. You’re looking to build a revenue engine, not run random plays.

Here’s how to operationalize the Messy Middle in your go-to-market motion:

1. Map Your Buyer’s Exploration & Evaluation Journey

Audit your current journey. Where do prospects explore (search, analyst reports, communities)? Where do they evaluate (comparison sites, product pages, webinars)?

Fill the gaps. Add middle-funnel content, third-party validation, and review-site presence. Don’t just optimize top or bottom. Focus on the loop in the middle.

2. Show Up Everywhere They Look

Google’s simulation found that simply “being present” across touchpoints like ads, search, content, and review sites was enough to shift preference by 18 to 87 percent.

Your buyers need to see you often and recognize your authority. That means retargeting, SEO, thought leadership, G2 reviews, and value-packed content. Consistency wins.

3. Embed the Six Biases into Your Funnel

• Add comparison charts to product pages (heuristics).

• Use AI to auto-personalize ROI calculators and demos (power of now).

• Showcase customer logos by ICP or industry (social proof).

• Create urgency in offers with dates or limited tiers (scarcity).

• Highlight analyst mentions and customer champions (authority).

• Offer zero-cost pilots, workshops, or assessments (power of free).

These don’t replace your strategy. They supercharge it.

4. Align Marketing, Sales & Product Around the Buyer Loop

The Messy Middle isn’t just marketing’s job. Sales must understand the nonlinear path. Product must support evaluation ease through guided tours or demo environments.

Get everyone on the same page. Build playbooks that reflect how buyers actually buy.

5. Use AI to Track, Predict, and Accelerate Buying Behavior

The complexity of the Messy Middle begs for AI augmentation. You can’t manually predict every twist in the buyer’s journey.

But with tools like Clay, Segment, or your CRM’s LLM integrations, you can:

• Predict intent based on exploration signals.

• Serve tailored nurture content based on evaluation stage.

• Use behavioral data to prioritize outbound efforts.

This is where my PRISMA™ Growth Framework comes in, especially in the Insight and Automation phases. It’s about turning chaos into clarity.

Final Thought: Don’t Try to Fix the Messy Middle. Master It.

You won’t eliminate the loops, distractions, or complexity your buyer faces. That’s not the goal.

The winners in 2025 will be the ones who influence the Messy Middle with intention, repetition, and relevance.

That’s how you scale predictably. That’s how you break through the growth ceiling. That’s how you outpace competitors who still think in funnels.

Ready to clean up the messy middle and drive pipeline with precision?
Let’s talk. Book a Discovery Call →