VP, Sales Transformation
“A sales process isn't a map of your tasks; it's a GPS for your buyer's journey.”
Orlando Castillo
Super Power:
My work starts with a simple belief: great companies don’t just build sales teams; they build teams of people who trust each other. My gift is architecting the systems that create that trust, turning ambiguity into clarity and potential into predictable, career-defining success.
What You Won’t Learn from my Bio:
I believe selling is a lot like cooking. Anyone can follow a recipe, but the best chefs understand why the ingredients work together. The same is true in sales; the best teams don’t just follow a process, they understand the belief behind it.
Specialties
Sales Transformation & Enablement, Sales Process Optimization, Custom Sales Playbook Development, Learning & Organizational Development, New Hire Onboarding & Ramp-Up, Sales Leadership & Coaching, Go-to-Market Strategy
Certifications
- Objective Management Group (OMG) Certified Partner, Sales Candidate Assessments
- Objective Management Group (OMG) Certified Partner, Sales Force Evaluations
- Coaching Certification Level 1 & 2 (VRBO)
What if your revenue wasn’t a guess at the end of every quarter? What if your team’s success wasn’t left to chance? It all starts with a simple idea: people don’t thrive in chaos; they thrive in clarity. They don’t follow checklists; they follow leaders and a purpose they trust. My entire career is built around this “Why.” I believe that when you give people a clear, documented process and invest in them as human beings, the results aren’t just predictable—they’re transformative.
How we do this is by partnering with leaders to replace outdated, “watch-me” training with robust, buyer-centric sales playbooks. We create actionable frameworks that unite teams around a shared vision and give them the confidence to excel. We build systems that foster accountability not through pressure, but through purpose.
The results of this approach speak for themselves: teams that onboard faster, stay longer, and feel a genuine sense of belonging. And yes, the numbers follow—like the $400M in incremental revenue generated through this philosophy. Because when you start with the “Why,” the “What” takes care of itself. You build something that lasts.
Because when you start with the “Why,” the “What” takes care of itself. You build something that lasts.
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Some Of My Work
Your CRM Checklist Isn’t a Sales Process (And Why That’s Killing Your Revenue)
Sales teams incorrectly believe their CRM checklist is their sales process. Recognizing this distinction is the first step toward building a predictable, scalable revenue engine. A checklist lives in the CRM. It’s a rearview mirror, a map of where you’ve been. A sales process, however, is a GPS for the future. It’s a commitment to guiding your buyer where they need to go. Let’s explore why teams need to understand the difference to protect their revenue for the year.
Want to Ramp Salespeople Faster? Start With Your Sales Process
A slow ramp for a new sales hire is not just a delay; it’s a drain on capital, morale, and momentum. But the problem, in most cases, isn’t the person you hired. It’s the system you dropped them into. You can’t expect a new builder to construct a house with just a pile of bricks and good intentions. You give them a blueprint. For a new salesperson, your sales process is that blueprint. To ramp salespeople faster, you can’t afford a sales process that is unclear, inconsistent, or locked away as “tribal knowledge.”
How to Spot a Broken Sales Process
We all want a sales process that flows like a well-oiled machine, predictably turning prospects into loyal customers. Yet, for many organizations, the sales process feels more like a leaky bucket, with opportunities, efforts, and revenue constantly seeping away. Why? Because the cracks often go unnoticed until it’s too late. So, how do you spot the subtle, and not-so-subtle, signs that your sales engine is sputtering? Let’s cut through the noise and identify the core indicators of a broken sales process, because you can’t fix what you don’t acknowledge.
