Building from Scratch: A CIO’s Candid Take on Becoming the Sole Salesperson featuring Kathleen Hurley

Sales Momentum

In this compelling episode of Sales Momentum, Howard Wolpoff sits down with Kate Hurley, an accomplished CIO-turned-entrepreneur who’s stepping into the world of sales for the first time in her impressive career. After years of leading tech strategy and operations for major real estate firms like CBRE and Madison International Realty, Kate is now the founder of Sage Inc., helping companies save time and money through smart technology solutions.

But there’s a twist—Kate now finds herself as the sole salesperson for her growing business.

Together, Howard and Kate dive deep into the mindset shift, the unexpected lessons, and the challenges that come with transitioning from internal operations to external sales. From building relationships to learning the art of patience in the sales cycle, Kate offers a raw and insightful look at what it means to start from scratch in sales—even when you’re already a seasoned executive.

What You’ll Learn in This Episode:

• Why technical expertise doesn’t always translate to sales success
• The emotional and practical hurdles of becoming your own sales team
• How relationship-building differs before and after the deal
• The hidden challenges in learning sales “on the fly” as a founder
• Why a clear “no” in sales can be just as valuable as a “yes”
• How understanding your client’s decision-making timeline is crucial
• The power of connecting through shared networks and inbound leads

Key Quote:

“You’re stacking a job you don’t know—sales—on top of the two or three jobs you’re already doing as a founder. That’s a challenge I didn’t fully prepare for.” – Kate Hurley

About Kate Hurley:
Kate is the founder of Sage Inc., a New York-based technology advisory firm. With decades of experience as a Chief Information Officer, Kate brings her operational excellence and client-facing insight to help organizations become more efficient, secure, and scalable.

Tune In To Learn:
✅ Why sales isn’t just pitching—it’s strategy, patience, and service
✅ How being “tech fluent” can both help and hinder your sales growth
✅ What every founder should consider about sales before they launch

Let’s Build Your Sales Momentum:
👉 If you’re a founder, executive, or transitioning pro navigating your first real sales journey—this episode is for you.

🎧 Available now on Spotify, Apple Podcasts, and all major platforms.

Connect with Howard:
LinkedIn: Howard Wolpoff
Website: www.HowardWolpoffSWC.com

Connect with Kate:
LinkedIn: Kate Hurley
Sage Inc.: www.sage.inc

We hope you found valuable insights to help you lead smarter, sell better, and build lasting relationships. If you enjoyed today’s conversation, don’t forget to subscribe, rate, and leave a review! Your feedback helps us bring more game-changing content to elevate your sales game.

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Keep pushing forward, keep evolving, and keep making those sales! 💥