Introducing Weekly Sales Office Hours:
Your Toughest Problems, Solved Together
After three decades in sales and marketing, I've seen it all. The deals that should have closed but didn't. The prospects who went dark at the worst possible moment. The negotiation that fell apart over something that seemed trivial. The salesperson who had all the potential but couldn't quite put it together.
Sound familiar? If you're nodding along, then I have something that might interest you.
What I'm Building
Starting next week, I'm launching something I'm calling Sales Office Hours - a weekly, invite-only session where sales professionals can bring their most pressing challenges to the table. Think of it as a cross between a mastermind group and office hours with your favorite professor, except the subject is the art and science of selling.
Every week, I'll set aside one hour for a small group of people to dive deep into real sales problems. Not theoretical case studies or generic best practices, but the actual, messy, complicated situations that keep you up at night.
How It Works
The format is simple: Come with your #1 sales problem, and we'll work through it together.
Maybe you're struggling with a salesperson who has great technical knowledge but can't seem to connect with prospects. Perhaps you're facing a complex enterprise deal where the decision-making process keeps shifting. Or you might be dealing with a pricing objection that you know isn't really about price, but you can't figure out what it's actually about.
In the early days, I'll be drawing heavily on my 30+ years of experience across the sales cycle - from prospecting and opening conversations to negotiation and closing. But my real goal is to build this into something bigger: a community where the group itself becomes the solution engine.
Why Invite-Only?
I've made this invite-only for a few reasons, and they're all important to me.
First, I want to create a safe space where people feel comfortable sharing real challenges, complete with all the messy details that make problems interesting. That requires trust, and trust comes from working with people you know.
Second, I'm not trying to build the biggest group possible. I'm trying to build the most valuable one. Quality over quantity, every time.
Third, and perhaps most importantly, this is my way of giving back to the people who've supported me along the way. If you've worked with me, collaborated with me, or been part of my professional journey, I want to invest in your success.
What's On (and Off) the Table
While HubSpot solutions might come up in conversation - it's part of my toolkit, after all - this isn't a HubSpot session. This is about fundamental sales challenges that transcend any particular platform or tool.
We'll tackle problems across the entire sales spectrum:
Prospecting and lead generation challenges
Opening conversations that actually lead somewhere
Managing complex sales cycles
Negotiation strategies and tactics
Closing techniques that feel natural, not forced
Managing and developing sales teams
Pipeline management and forecasting
Dealing with difficult personalities (both prospects and colleagues)
If it's keeping you from hitting your numbers or building the sales organization you want, it's fair game.
The Community Vision
Here's what I'm really excited about: I don't want to be the only one with answers.
My vision is that over time, this group becomes a community of sales professionals who support each other. Someone who solved a similar prospecting challenge last month helps someone facing it today. A sales manager who figured out how to motivate a particular type of rep shares their approach with someone struggling with the same issue.
The best sales advice often comes from someone who just went through exactly what you're facing. My role will be to facilitate these connections and add perspective from my years in the trenches.
How to Get an Invite
Since this is invite-only, you'll need to ask for an invitation. But here's the thing - if you're reading this and thinking it sounds valuable, you probably already qualify.
The criteria is simple: I should know you, have worked with you, or we should have some professional connection. If we've collaborated on a project, been introduced by a mutual contact, or crossed paths in the sales and marketing world, just reach out.
Send me a note explaining what kind of sales challenge you're facing and why you'd like to join. I'm not looking for a formal application - just a genuine interest in both getting help and helping others.
What This Isn't
Let me be clear about what this isn't:
This isn't a sales pitch disguised as help
This isn't a generic webinar with predetermined content
This isn't a platform for vendors to push their solutions
This isn't open to everyone who asks
This is a focused, professional group of people committed to helping each other succeed in sales.
Ready to Join?
If this resonates with you, and you think you'd both benefit from and contribute to this kind of community, I'd love to hear from you.
The first session is next week, and I'm excited to see what problems we can solve together.
After all, the best salespeople have always known something that others often miss: success isn't a solo sport. It's about relationships, community, and helping each other win.
Let's build something valuable together.
Interested in joining Sales Office Hours? Drop me a line and let's talk about your biggest sales challenge. If we've worked together or have a professional connection, an invitation is just an email away.