podcast ·Oct 14, 2025

Building a Sales-Ready Organization with Christopher Filipiak

by Drewbie Wilson

In this episode of Call The Damn Leads, I sit down with Christopher Filipiak — a sales strategist, engineer-turned-entrepreneur, and creator of the Sales Ready Organization Framework. Christopher has helped hundreds of CEOs ditch the fear of selling, stop wasting resources, and build scalable, repeatable sales systems that actually work.

We dig deep into why so many founders hide from sales, how skipping the fundamentals leads to expensive hiring mistakes, and why the first person who needs to master sales in your business is you.

If you’ve ever thought, “I’ll just hire a sales team and they’ll figure it out”, you need to hear this.

🔥 Episode Highlights

10 Minutes to 2 Sales Meetings – Christopher shares a real-life example of calling just three leads, booking two meetings, and advancing both to discovery calls — all in under 10 minutes. Proof that a well-targeted, well-practiced outreach crushes “spray and pray” dialing.
The CEO Sales Avoidance Epidemic – Founders often choose “comfortable” tactics over effective ones, building sales processes around what feels safe rather than what works. Christopher calls this out as selfish — if you can solve someone’s problem better than anyone else, hiding from sales is robbing them of that solution.
The $400,000 Sales Hire Mistake – On average, CEOs fire 3.25 salespeople before finding the right one. Each failed hire can cost upwards of $400K when you add up lost time, missed revenue, and onboarding costs.
Your Business is a Lamborghini – Throwing a rookie into sales without training or systems is like handing the keys to a luxury sports car to a 16-year-old and expecting a perfect lap time.
Why Salespeople Fail in Small Businesses – Most failures happen because of unclear expectations, no client avatar, and broken processes — not because the salesperson is bad.
The Sales Ready Organization Framework – Five pillars that every business needs before scaling sales:

Mindset – Sales confidence from the top down.
Leadership – Direction, accountability, and vision.
Marketing – Targeting the right people with the right message.
Sales – Documented, repeatable, proven process.
Project Management – Continuous improvement on the sales operation.

Stop Wasting Time – Too many businesses overproduce: proposals nobody asked for, calls to unqualified leads, and “busy work” that doesn’t lead to revenue.
The Three-Step CEO Sales Path –

Master sales yourself to create consistent revenue.
Build a sales-ready organization with processes, clarity, and systems.
Hire and equip salespeople who can scale what’s already working.

💡 Key Takeaways

Conversations with the right people beat mass outreach every time.
CEOs must lead sales at the high-value deal level until their process is bulletproof.
Hiring salespeople won’t fix a broken sales system — it will magnify the problems.
Clearly define your ideal client avatar before you make a single hire.
Stop expecting salespeople to do marketing — give them qualified leads and a clear process.
Document your sales process so it’s “microwave instructions” simple.
Build mindset into your sales culture — it’s as important as skills and scripts.
Use project management to improve sales operations continuously.
Eliminate wasted effort — measure activities by how directly they lead to revenue.

🔗 How to Connect with Christopher Filipiak

Take Christopher’s Sales Ready Organization Assessment to find out exactly where your business stands: (link to be included in blog post)

🌐 Website: https://www.christopherfilipiak.com/
💼 LinkedIn: https://www.linkedin.com/in/christopherfilipiak

🎯 Call to Action

Call The Damn Leads

"By sales professionals, for sales professionals - Tales of your wildest sales stories and tactics to succeed in your sales career across various industries."

Join Drewbie Wilson, a sales veteran with over 20 years of experience, as he brings you insider stories, humor, and actionable strategies to excel in your sales journey.

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Wild Sales Stories: Engaging tales of real-life sales adventures.
Proven Tactics: Actionable strategies to boost your sales game.
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