Enterprise deals are won before the first C-level conversation ever happens.

Most reps don’t understand this. They burn through LinkedIn InMail credits trying to land meetings with VPs and Chief Officers, wondering why their outreach gets ignored.

After building sales playbooks for enterprise teams over the past 18+ years, I’ve seen what separates reps who consistently close six-figure deals from those who flame out.

It comes down to three things: rigorous account planning, strategic relationship building, and knowing when to leverage your ecosystem.

Stop Swinging at C-Level Executives First

Bob Spina, former enterprise sales leader at Gong, shared something on my podcast that changed how I think about prospecting into large organizations. He calls it “groundswell outbound.”

The idea is simple but counterintuitive: Don’t start at the top.

Instead of cold-calling the CRO who gets 50 pitches a week, start with regional directors or frontline employees. Test your organizational hypothesis. Gather real data about how the company actually operates.

When you finally do reach that C-level executive, your conversation isn’t generic. It’s sharp. It’s informed. You’re not guessing at their priorities because you’ve already talked to the people executing their strategy.

This is how you avoid the “flying blind” problem that kills most enterprise deals.

Build Your Point of View Before You Prospect

Enterprise buyers can smell lazy research from a mile away.

If your outreach sounds like it could apply to any company in their industry, you’ve already lost. Your prospects need to believe you understand their specific business, not just their vertical.

That means doing the work:

  • Study their annual reports for strategic initiatives
  • Track recent leadership changes and what they signal
  • Monitor industry regulations that might be forcing their hand
  • Understand which competitors are winning and why

Your SDRs should be organizational cartographers. They need to map out the complex web of decision-makers, budget owners, influencers, technical evaluators, and potential blockers before an AE ever takes a meeting.

This is account-based prospecting done right. Quality over quantity. Depth over breadth.

When your AE walks into that first call with a multi-threaded strategy already in place, you’re not hoping for a deal. You’re running a campaign.

Leverage Your Ecosystem

Here’s what nobody tells you about enterprise deals: They often die because of a partner relationship you didn’t know about.

Autum Grimm, founder of PartnerTap, breaks down co-selling better than anyone I’ve heard. She defines it as “activating the connection point between sales professionals so that they can work across organizations to source, influence, or accelerate a sales process.”

In short, you need to know who else has relationships in your target account, and you need to work with them.

This includes:

  • Technology partners who already have a foothold
  • Resellers who’ve earned trust over the years
  • Influential consultants who navigate these organizations daily

Autum even shared that when LastPass implemented a real co-selling strategy with just one partner, they identified 15,500 new logo accounts. Revenue went up 4X in the first year.

That’s not a fluke. That’s what happens when you stop treating partnerships as a nice-to-have and start treating them as a core prospecting strategy.

Final Thoughts

Enterprise prospecting isn’t transactional. It’s strategic.

You’re not booking one meeting. You’re building intelligence, mapping relationships, and positioning your organization as the obvious choice before your prospect even realizes they’re in a buying cycle.

Do the research. Build the groundswell. Leverage your ecosystem. Collaborate like your quota depends on it.

Because it really does.

Explore Further: Recommended Resources

In my interview with Bob Spina, he details how he built Gong’s strategic sales team and scaled their successful enterprise sales division. He explains that after realizing the traditional SMB playbook wouldn’t work upmarket, they had to pivot their value proposition to focus on business value and strategic initiatives.

A key element of their outbound strategy was the “groundswell approach.”

If you are planning your GTM strategy to break into the enterprise segment, it’s important to understand how to build a highly repeatable playbook using this data-driven process.

Give it a listen here:

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