As an owner-led sales MSP, you’re in the driver’s seat—but here’s the thing: you’ve got to have a windshield mentality. Always focused on where you’re going while keeping an eye on the rearview mirror to make sure you’re learning from the past and improving every step of the way.
I’ve built multi-million-dollar businesses and sales from scratch by living this mentality every single day. Resilience has been key. I’ve faced setbacks, learned from them, and kept pushing forward. If you can embrace this mindset, you’ll do more than survive—you’ll thrive.

Before I built businesses and established revenue operations, I was learning vital lessons in discipline and leadership. As a Cadet at The Citadel, The Military College of South Carolina, I discovered the profound impact of discipline and the power of servant leadership. While many of my fellow alumni adopted the “bark orders and put people in their place” mentality, I realized early on that wasn’t the leader I wanted to be. I believe in showing by doing—leading through action, not just words.
This is a mentality I’ve carried through my entrepreneurial journey. Systems and processes are important, but the real magic happens when you roll up your sleeves and do the work. That’s where my leadership strength lies—actually driving growth and putting in the work. Sure, I have a superpower of resilience and focus, but I also know that building a startup means it’s not all on my shoulders. There are times I need to step back and build systems around what works. That’s why I surround myself with the smartest people I can. I may be one piece of the puzzle, but it’s the collective strength of a talented team that makes everything come together.
So, how do you become a sales machine that keeps momentum going and builds a reputation of trust? Let’s break it down:
1. Serve First, Lead Always
Sales isn’t about pushing your service on people—it’s about solving problems. Period. You need to serve your prospects by genuinely understanding their pain points. The trust you build comes from serving, not just selling. Trust is everything. When you earn it, you create a foundation that not only drives deals but turns clients into long-term partners.
2. Discipline to Follow Through
As an owner-led MSP, the buck stops with you. When you make a commitment, own it—no exceptions. There’s no room for half-effort here. People want someone they can count on. If you say you’re going to do something, do it. It's not just about closing a deal, it’s about living up to your promises and doing what you say you will. That’s how you build a reputation of integrity that powers your business.
3. Ask the Tough Questions, Even When They’re Uncomfortable
Sales is about discovery. You can’t be afraid to ask the tough questions because those are the ones that will unlock the real needs of your prospects. Yes, it’s uncomfortable sometimes, but it’s exactly what separates a trusted advisor from just another vendor. Get curious, dig deep, and have the confidence to challenge your prospects’ thinking. It’s how you show them you’re here for the long haul.
Some tough questions to ask:
What’s your biggest cybersecurity headache right now?
How does that risk impact your business financially?
What’s the one thing that keeps you up at night about your IT systems?
By asking these, you’re moving from “selling” to solving—and that’s where the magic happens.
4. Keep the Momentum Rolling
If you’re an owner-led sales MSP, your pipeline needs to be moving forward constantly. This is where your windshield mentality comes into play. Keep an eye on the long-term while driving day-by-day growth. Momentum is what gets you from “maybe” to “yes.” So, make it a habit to always be prospecting, following up, nurturing relationships, and keeping deals in motion. The more you stay engaged, the more progress you make—and the faster you’ll see those deals move through the pipeline.
5. Look Back to Move Forward
Here’s where the rearview mirror comes into play. Sales isn’t just about sprinting forward—it’s about being self-aware enough to learn from your mistakes and celebrate the small wins along the way. Yeah, you’re hustling toward growth, but pause every now and then to reflect on what’s working and what’s not. Celebrate those small wins. They matter.
Final Thoughts: Own Your Sales Journey
Being an owner-led sales machine isn’t easy. It’s about relentless discipline, serving your clients first, and always asking the tough questions. But it’s also about resilience. I’ve built a million-dollar business from the ground up because I didn’t stop when things got hard. I stayed disciplined, focused, and learned from every challenge.
So, are you ready to embrace windshield mentality as a owner-led sales MSP?
Own your sales journey, push forward, and level up. The road might be tough, but the rewards are worth it.
Comments