Should You Hire a Sales Leader or Install a Sales System First?

If you’re leading a growing company in Oregon or Washington and struggling to get consistent sales performance, you’re not alone.

A few weeks ago, I sat across from the co-founders of a $7M business – a dynamic duo who had built their company from the ground up. Smart. Driven. Deeply committed to their team.

We were talking about implementing the Outgrow system. They asked great questions. But I could tell something else was underneath.

They weren’t saying, “Will Outgrow work?”

They were asking, “Will our team actually do it?”

That’s when one of them said something I’ll never forget:

“Craig, I trust you. But I’ve been burned. We spent over $60,000 hiring a seasoned sales leader. Add in the headhunting fees, monthly consulting, and training…it was a massive investment. And after six months, we had to let him go. The volume never changed. The ROI just wasn’t there.”

He wasn’t doubting the Outgrow system.

He wasn’t doubting his team.

He was doubting whether another sales investment would finally deliver.

That hesitation? It’s more common than you might think.

The $60,000 Lesson: When Sales Hires Don’t Solve the Real Problem

When revenue feels stuck, many business owners default to the same fix:

“We need someone who knows sales. Let’s hire a heavy hitter. A VP. A Director. Someone who can fix this.”

So they go out and:

• Hire a senior sales leader or VP
• Pay steep headhunter and onboarding fees
• Promise the team a new era of growth

But here’s what usually happens next:

• The new hire spends months “learning the business”
• The team gets confused about who’s driving growth
• The owner ends up still carrying the load
• The leader struggles without a clear system
• And sales? They stay flat

Six to twelve months later, the “hero” is gone.

The team is still stuck.

And leadership is even more hesitant to invest again.

Outgrow Is Not a Hire. It’s a System.

When that founder shared his experience, I looked him in the eye and said:

“This isn’t about hiring another hero to save the day. It’s about a system that will help the team you already have succeed – equipping the team you already trust with a proven process that they can actually follow.”

Then I asked him to do something important before our next meeting:

Listen to the Outgrow audiobook.

Let Alex Goldfayn explain the daily behaviors, the tracking, the mindset shift.

He did. And when we met again, he wasn’t just curious – he was committed.

Because growth doesn’t require a new hire.

It requires a team that knows what to do, and a system that helps them do it consistently.

Why Most Sales Hires Struggle Without a System

Even great salespeople flounder in companies that don’t have:

• A culture of proactive outreach
• A structure for daily action
• A tracker that measures inputs
• Coaching and reinforcement

It’s not about the person. It’s about the playbook.

The best sales hires succeed when they inherit a system that works.

The best sales teams thrive when their leaders set the tempo.

That’s what Outgrow provides:

• Proactive Calls
• DYKs and rDYKs
• Follow-up systems
• Simple, scalable accountability rhythms

Trust Your Team? Equip Them.

If you find yourself saying:

• “My team’s capable, but not proactive”
• “They’re good with customers, but don’t follow up”
• “They’re busy, but growth is inconsistent”

You don’t need to replace them.

You need to give them a system where:

• Three to five proactive calls per day are the norm
• Referrals are expected and tracked
• Outreach is structured, not sporadic
• Confidence is built through repetition, not pressure
• Small wins are celebrated, not overlooked

When that system is in place, you’ll realize:

Your people were never the problem.

They just needed clarity and consistency.

The ROI Isn’t Just Revenue. It’s Confidence.

When the founder I spoke with said yes to Outgrow, I didn’t promise overnight results.

I promised a shift:

• In how his team talks
• In how they show up
• In how they own their number
• In how they follow through

That shift builds confidence.

And confident teams sell.

You’re not just investing in calls made or deals closed.

You’re investing in a culture where everyone knows what to do – and actually does it.

Final Thought: In Oregon and Washington, Don’t Hire the Hero – Build the System

Whether you’re running a professional services firm in Portland, an engineering company in Seattle, or a construction business in Salem, the lesson is the same:

You don’t need to hire a hero.

You need a system that your team can run, without depending on personality or pressure.

Outgrow works.

It’s working right now in Oregon and Washington companies that want more than quick fixes. They want repeatable sales growth without hiring cycles that don’t stick.

The key?

It starts with leadership.

When you believe in the system, your team will too.

And when your team has a system?

Growth becomes a matter of execution, not luck.

Let’s Talk

Want to explore what this could look like for your team?

• Visit RunOutgrow.com for details
• Read my full book review of Outgrow on Amazon
• Or connect with me directly on LinkedIn

No pitch. No pressure.

Just a real conversation about what’s next.