Brenda sits down with Jason Short, veteran CTO and consulting executive at CH2 Solutions, to explore how negotiation, leadership psychology, and self-awareness intersect in the fast-paced world of healthtech.

From learning the art of negotiation through a 12-cassette tape series during his DC commutes to advising PE-backed companies on billion-dollar decisions, Jason shares how curiosity, structure, and empathy can turn negotiation from a power play into a genuine superpower.

Together, they unpack how preparation beats pressure, why most executives mistake silence for weakness, and how to read the real game being played behind the deal.

Jason also reflects on being the first male guest on RedefineHER and what listening, allyship, and equity look like when you’re negotiating for a better future in women’s health.

If you’ve ever wondered how leaders win without ego, this episode will change how you think about influence, confidence, and communication.

In This Episode, We Cover:

✔️ Why negotiation is a daily leadership skill, not just a deal tactic

✔️ How Jason’s “cassette tape education” shaped his executive mindset

✔️ The three stages of negotiation: technique, counter, and masked offer

✔️ How to navigate “good cop/bad cop” energy in high-stakes rooms

✔️ Why preparation and silence are the sharpest negotiation tools

✔️ How to detect hidden agendas and when to plant one ethically

✔️ What PE and VC leaders need to know before investing in women’s health

Timeline:

00:00 Introduction to Negotiation Techniques

05:16 The Three Stages of Negotiation

10:28 Real-Life Applications of Negotiation15:51 Negotiating with Private Equity Firms

22:14 The Art of Negotiation

26:49 Understanding Hidden Agendas

30:05 Fundraising Strategies for Startups

34:23 Preparing for Board Meetings

36:56 Owning Your Career Path

41:38 Women's Health in Tech Negotiations

Mentioned in the Episode:

• “Negotiation isn’t a power play ,it’s a framework for understanding people.”- Roger Dawson’s Secrets of Power Negotiating

• “Preparation beats pressure every time.”
• The “Puppy Dog Close” and why it still works

• “If you’re investing in women’s health, start by asking what matters to women.”

Connect with Jason:

🌐 Website: ⁠⁠ch2solutions.com⁠⁠

💻 LinkedIn: ⁠⁠Jason Short⁠⁠

RedefineHER Podcast Credits

🎙 Host: ⁠⁠Brenda Armstrong⁠⁠

🎧 Producer: ⁠⁠Tarryn Long⁠⁠

💼 Sponsor: CH2 SolutionsWhere Technical Depth Meets Business Agility.CH2 helps healthcare and healthtech companies modernize legacy systems to scale faster, innovate smarter, and deliver impact where it matters most.Learn more at ⁠⁠ch2solutions.com⁠⁠.

📜 Disclaimer⚠️ This content is for educational purposes only and is not business or legal advice.©2025 RedefineHER Podcast. Please share with credit and direct link.