1. Your First Sales Hire Can Make or Break You

Most startups wait too long or hire the wrong profile. One company Dale spoke with had 6 failed sales hires before realizing they needed help.

Tip: Don’t hire someone who’s only worked in corporate. Look for doers who can operate without hand-holding, generate their own leads, and aren’t afraid to build from scratch.

2. Don’t Just Ask Why You Lost. Ask Why You Won?

We obsess over loss reasons, but the gold is often in the win reasons. That’s where your strongest messaging lives.

Tip: Ask your newest customers why they chose you. You may discover value props or differentiators that even your own team hadn’t articulated clearly.

3. Don’t Hire a Sales Leader Until You’re Ready

Most founders try to hire a CRO or Head of Sales too early, often before they’ve figured out how to sell themselves.

Tip: Founder-led sales is a must in the early stages. Do it yourself first so you can write the playbook and coach others.

4. Compensation Plans Drive Behavior, So Design Them Carefully

Founders often wing their first comp plan and end up rewarding the wrong behaviors.

Tip: Your comp plan should align with your business goals and reward the activities you need most, whether it’s hunting new logos, closing fast, or growing expansion revenue. When in doubt, get expert help.

5. If You Don’t Know Where Your Deals Come From, You’re Flying Blind

One of the first things Dale does with clients is audit deal sources. Where deals actually originate, not what the CRM says.

Tip: Track wins, losses, and referrals. Double down on what’s working. And if all your leads come from your network, it’s time to build a real GTM engine.

6. Nail Your ICP, Then Stick to It

Too many teams waste time on edge-case customers or chasing random interest.

Tip: Your Ideal Customer Profile (ICP) should be based on customers who get the most value, not who shouts the loudest. And don’t bend your roadmap to close one big logo. That usually backfires.

7. Free Isn’t Always Better. Don’t Let Discounts Devalue Your Product

Early-stage companies are tempted to slash prices to win early deals, but that can attract the wrong customers and hurt long-term retention.

Tip: Be confident in your value. Customers who pay more are often more committed and easier to work with.

8. Urgency Is Created, Not Discovered

"Time kills deals," Dale says, and you can’t always rely on the customer to move fast.

Tip: Use deal rooms, mutual action plans, and commercial incentives, but more importantly, tie the deal to your buyer’s personal win. What’s in it for them if this project succeeds?

9. LinkedIn Is Your Best GTM Channel. And It’s Free

Dale credits much of his pipeline to personal content on LinkedIn. His first deal came not from cold outreach, but from someone who had seen his posts and DMed him on Facebook.

Tip: If you're a founder or sales leader, post regularly. Share what you're learning, who you’re helping, and what problems you're solving. You’re not too early, it compounds.

10. Big Events Are Overrated. Go Small and Targeted

Dale spent thousands attending big-name summits in year one. “It was exciting, but nothing came of it.” When he shifted to niche, curated events, everything changed.

Tip: Focus on smaller events where your ideal customer will be. Build relationships, not just badges.