Welcome to the Win Lab with Mike - Blog, the home for sales insights, strategies, and stories from the field.
Here, you’ll find two perspectives:
For founders and executives scaling their business: strategic advice from Michael Oreskovic OGC Founder, on building sales processes, hiring teams, and creating repeatable revenue engines that help startups and SMBs grow with confidence.
For sales professionals (SDRs, AEs, and new managers): practical frameworks and coaching on cold calling, discovery, objection handling, pipeline management, and leadership.
Every post is built around one goal: helping you master the art and science of selling—whether you’re chasing your first quota, designing a go-to-market strategy, scaling your Start-Up.
And Why So Many Startups Learn It Too Late
Many startups rely too heavily on a product-led growth model and delay building a true sales motion. Drawing insights from the Revenue Builders podcast with John McMahon, John Kaplan, and Dan Fougere, this article explores why PLG alone cannot sustain enterprise growth and how founders can build sales leadership early to scale successfully.
How to Drive the Right Behavior Fast!
Most leaders try to fix sales performance with new messaging or new metrics.
The fastest way to change behavior is through the compensation plan.
When I help SaaS founders and sales leaders rethink their go-to-market, we always start with one question: “Does your comp plan tell your team what you actually value?”
This article breaks down seven lessons I’ve learned about sales compensation from years leading and coaching high-performing teams.
...And Why It Should Scare Every Sales Leader
AI isn’t the enemy of sales...blind trust is.
Data can reveal patterns, but it can’t understand context.
And too many teams are building GTM strategies straight from dashboards instead of real-world experience.
I wrote about the quiet cost of over-relying on AI, and what it’s doing to the art of selling.
Elon and the Stoics Say Use That Failure to Win
Most startups don’t die because of bad ideas. They die because no one stops to ask what guarantees failure. Here’s my take on how inversion thinking from Elon Musk, Charlie Munger, and the Stoics can help founders survive and win.
Start-up culture scales just like innovation. Founders face a critical moment of crossing the cultural “chasm” as they grow, where the DNA that made them great is at risk. Inspired by Simon Sinek’s talk on cultural change and the Law of Diffusion of Innovations, this article explores how those principles apply to start-ups and what founders can do to protect their culture while scaling.
Startups and scale-ups demand very different types of sales talent. In this post, I break down why scrappy, hands-on reps thrive early on, why disciplined and process-driven talent drives growth at scale, and the hard truth about who can (and can’t) make the leap between the two.