"Cringe" Sales Call with $300M Chief Revenue Officer (What I Learned)

If it sounds too good to be true, you might be getting played. In this episode of Getting to Club, Chris breaks down the "pleasant surprise" tactic—a sneaky negotiation strategy buyers use to make sellers feel like they’ve hit the jackpot. But this excitement can cost you big discounts without you even realizing it. Learn how to spot this tactic, how to protect your pricing, and what steps you can take to stay ahead in negotiations. If you've ever wondered why a deal felt too easy, this one's for you!

How do you drive urgency and action without crossing ethical lines? In this episode, Chris unveils four powerful methods for "twisting the knife" in sales—techniques that ramp up urgency by exposing pain points. But these tactics come with a warning: used improperly, they can backfire. Chris dives into real-world examples, from sharing painful customer stories to asking precise, high-impact questions, all aimed at moving your deals forward faster. Whether you’re new to sales or a seasoned pro, mastering these techniques could be a game-changer. Just don’t forget your fireproof suit!

How do you transform a small deal into a record-breaking one? In this episode of Getting to Club, Chris shares the inspiring story of Brian, a mid-market AE who turned a $20,000 deal into a massive $433,000 win—all in under 90 days. Discover the three key strategies that helped Brian reframe the conversation, unlock deeper business problems, and engage with top-level decision-makers. If you’ve ever wondered how to maximize your deal sizes and hit quota faster, this episode will show you the playbook to get there.

In this episode, Chris tackles a common challenge for sales professionals: how to handle buyers who flinch at your price. He breaks down why experienced buyers often use this tactic to shake your confidence and push for a discount, and provides a structured approach to maintain control. From delivering price with value context to calmly addressing flinching as it happens, Chris outlines practical strategies to help you stay firm on your pricing. Tune in to learn how to navigate tough negotiations without sacrificing your value!

In this episode, Chris draws on a MASSIVE data set of over 1 million sales calls to reveal the top 17 takeaways that can boost your sales game. From the ideal amount of talking in discovery calls to the importance of multi-threading and handling objections, Chris distills complex research into actionable tips. These insights, based on real-world data, can help you close more deals faster and with greater success. Whether you're a seasoned pro or just starting out, these strategies are game-changers. Tune in for the key patterns of top-performing salespeople!

In this episode, Chris delivers a concise yet crucial lesson for mid-market sellers: handle legal concerns before diving into price negotiations. Using real-world examples, he explains why tackling legal terms first can save you from wasting time on pricing discussions that may never materialize into a deal. If legal terms are a dealbreaker, pricing becomes irrelevant. Chris breaks down how to structure your negotiation process for smoother, more efficient deals.

In this episode of Getting to Club, Chris dives into the seven key components that distinguish top-earning sales professionals who rake in $350,000 or more annually. From the markets they target to their mindset strategies and continuous skill development, Chris uncovers the essential traits and habits of high earners. If you're aiming to break into this elite group, this episode is packed with actionable insights that could transform your approach and earnings potential.

Chris shares his experience of a sales meeting with a chief revenue officer of a SaaS company. He discusses the company's goals of selling bigger enterprise deals and increasing their average contract value (ACV). However, there was a discrepancy in the information he had gathered prior to the meeting. Despite this, he was able to course-correct and engage in a deep discovery conversation with the CRO. Chris highlights the importance of having a 'what we heard' slide in C-suite meetings to earn instant credibility. He also emphasizes the need to let champions save face and take responsibility for outcomes. Takeaways Having a 'what we heard' slide in C-suite meetings can earn instant credibility Letting champions save face is important for building trust Taking responsibility for outcomes earns respect and credibility Deep discovery conversations can help course-correct and gather accurate information

Chris shares his experience of negotiating a deal and the challenges he faced. He discusses the importance of having a systematic approach to negotiation and introduces the first four steps of his negotiation process. These steps include summarizing and passing the torch, getting all the buyer's asks on the table, stack ranking the asks, and uncovering the underlying needs behind the requests. By following these steps, sellers can kick off a negotiation session productively and establish the business value before discussing price. Takeaways Having a systematic approach to negotiation is crucial for success. The first four steps of the negotiation process are summarizing and passing the torch, getting all the buyer's asks on the table, stack ranking the asks, and uncovering the underlying needs. Summarizing the key elements of the partnership at the beginning of a negotiation session establishes the business value and prevents the focus from solely being on price. Getting all the buyer's asks on the table before responding allows sellers to see the bigger picture and prioritize the requests. Uncovering the underlying needs behind the requests helps sellers find creative solutions that meet both parties' interests.

In this episode of Getting to Club, Chris shares the output of a recent conversation with the CRO of a $2.3 billion company. That conversation covered the shift from a "demand-positive" to a "demand-negative" market and the five essential skills needed to thrive in challenging sales climates. This episode is a must-listen for sales professionals aiming to adapt and succeed regardless of market conditions.