In this newsletter, I’ll break down why enterprise tech sales are uniquely complex, the common mistakes companies make, and the opportunities in this space. I’ll also provide a mini-playbook to help you navigate these deals and build a sustainable enterprise business.

What is Enterprise Tech?

For this discussion, Enterprise Tech refers to tech companies—primarily SaaS—selling products and services to mid-to-large enterprises. Within this space, two types of companies exist:

1. Legacy Tech Companies – Established firms from the 90s and early 2000s (e.g., Microsoft, IBM, Oracle) that have transitioned to cloud-first, SaaS-driven models.
2. SaaS-First Companies – Ranging from startups to large enterprises, these companies build and sell software primarily for enterprise customers.

This newsletter focuses on SaaS companies.

First- My Prediction on Enterprise Market given recent recession fears and macro uncertainty

Given the recent tariffs, uncertainty, and recessionary fears, here is what you’ll likely start to see as an enterprise leader:

👀 Prospect Behavior:

1. Pipeline stalls. Most prospects will hit pause on new tech. They’re focused on surviving, not spending.
2. Sales cycles get longer. Deals that were close to the finish line will drag, or suddenly require more stakeholders.
3. Tech consolidation begins. Prospects will ask current vendors if they can do what you were offering—or try to build a workaround.

🤝 Existing Customer Behavior:

4. No appetite for upsells. Some will ask for price cuts or downgrade.
5. Feature requests spike. Expect more “must-haves” delivered faster—and for free.
6. Justification pressure. Your internal champions will now need to justify their spend to the CFO—especially during Q4 planning.
7. Renewals get ruthless. Only tools with clear ROI survive. Everything else is up for review.

🏢 Your Business Impact:

8. Smaller pipeline, longer cycles. CAC rises, and short-term marketing ROI looks ugly.
9. New logo wins slow. Live revenue gets delayed. Margins tighten. Discounts go up.
10. Product demands grow. CS gets overloaded trying to retain high-risk accounts.
11. Red accounts start to show. And they won’t all be small ones.

Hence, navigating complex deals is even tougher in today’s environment.

Why Are Enterprise Deals So Tough?

Example: AI Company Selling to Construction

Consider an AI startup solving a key problem in construction. Selling to a local construction firm with $5M in revenue is vastly different from selling to a national enterprise with $200M+ in revenue. The challenges include:

• More stakeholders & decision-makers – The buying process is no longer a single decision-maker signing off on a deal.
• Higher expectations for support – Enterprises expect robust implementation, onboarding, and post-sale support.
• Longer sales cycles – Deals can take 12-18 months due to extensive evaluation and approval processes.
• Product gaps – many businesses have unique needs are ask for custom features not on your roadmap and so forth.

Where 80% of Enterprise Tech Businesses Go Wrong

It’s not just about navigating the sale—it’s about building the enterprise muscle to sustain and scale these deals. Common pitfalls include:

• Measuring enterprise P&L against SMB benchmarks
• Tracking wins and bookings on a monthly basis instead of long-term ARR growth
• Relying on product features to sell rather than solving business problems
• Selling to end-users instead of cultivating internal champions
• Letting customers dictate the product roadmap instead of driving a strategic vision
• Saying “yes” to every opportunity instead of focusing on ideal customers

What I’ve Seen:

Having been on both sides of the table— (1) building an enterprise tech business selling to large multinational enterprises and (2) purchasing enterprise tech while leading digital transformation at these same organizations—I’ve gained a deep understanding of what drives success in complex enterprise deals.

Here’s what I know for sure:

• Navigating enterprise sales is simple, but not easy—the complexity often comes from within.
• The real challenge isn’t the deal itself—it’s the lack of clarity, alignment, and communication that makes it harder than it needs to be.
• In the end, execution is the true differentiator—it’s what separates those who thrive from those who merely survive.

BONUS

What should you actually do as an Enterprise leader today given the uncertainty and potential economic downturn?

💰 Revenue & Pipeline:

1. Double down on high-likelihood, high-economics deals. Cut the rest.
2. Get in the room with prospects. Trust wins deals. Become their advisor.
3. Lean in with GTM teams. Show up. Help close deals. Lead from the front.

📈 Customers:

4. Focus on the top 20% that drive 80% of revenue. Give them premium support—even if it shrinks margins in the short term.
5. Meet their leadership. Ask how you can help—both the business and them personally.6. Deliver what you promised. Build what you said you would.

💵 Profitability & EBITDA:

7. If you’re already built with a profitability first mindset, great. Unfortunately most are not. If so —make the cuts, make them once, and cut deep.
8. Kill non-revenue projects. For example, if you’re planning a GTM partner event and partners don’t drive deals—pause it for 6–12 months.
9. Identify your top 3 pipeline channels. Pause the rest. The top 3 are your 80/20.
10. Find efficiencies across teams. Consolidate overlapping functions to boost capacity and reduce overhead.
11. Hire slow. Don’t staff ahead of revenue. Let growth force your hand.