Getting to Club

Kyle Coleman has spent 15 years architecting outbound motions that don't rely on volume - first as the founding SDR at Looker, then building Clary's outbound engine from $15M to nearly $150M in revenue, and now as Global VP of Marketing at ClickUp.In this conversation, Chris and Kyle unpack the difference between personalization (which is now table stakes and largely useless) and a real point of view - the kind that makes a CRO stop scrolling and actually reply.Kyle walks through the exact 5-step framework he's used to train SDR teams on POV-led outbound, why "signal monitoring" without interpretation is just dressed-up spam, and how he scaled this approach at Clary to triple qualified pipeline while sending 25-30 emails a day instead of thousands.If you're a sales leader watching your team's reply rates collapse under the weight of AI-generated noise, this episode is the antidote.

Chris Orlob shares five patterns he's observed across the most elite revenue organizations after working with thousands of sales teams at InsideSales.com, Gong, and now Caliber.From maniacally focusing on where you win, to obsessing over narrative, to building rock-solid sales stages with binary exit criteria - these are the habits that separate top-performing teams from mediocre ones.Plus, why treating skill development like a performance system (not an HR exercise) is the missing piece behind every great sales process.A practical breakdown for revenue leaders, founders, and frontline managers who want to operationalize excellence.

Welcome to the Caliber Show, a reset and a rebrand.In this opening episode, Chris Orlob unpacks why 84% of sales training initiatives fail to produce lasting behavior change, and walks through the 15-step operating system elite revenue teams use to durably upskill sellers, install reinforcement, and reduce performance variance across the org.Tune in every Monday and Friday morning for the latest Caliber Show!

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 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 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 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 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 tackles the often intimidating task of discussing pricing with potential clients. He shares six indispensable tips for making pricing calls that not only convey value but also sell effectively. Whether you’re new to sales or looking to refine your approach, this episode's practical advice on pricing will empower you to handle these crucial conversations with ease and professionalism.

In this episode of Getting to Club, Chris explores the intense and often unspoken truths about the competitive nature of top-tier salespeople. It's undeniable that the most successful sales professionals operate with a relentless, almost ruthless drive to outperform competitors—not merely to succeed, but to dominate the sales field. This episode offers a candid look into what it really takes to be at the top in sales, suggesting that achieving extraordinary results sometimes requires an extraordinary competitive spirit... while maintaining ethical integrity.

Is AI coming for your sales job? In this episode of Getting to Club, Chris explores AI's role in the future of sales and discusses how artificial intelligence might impact different roles based on if you're a "value communicator" or a "value creator." This episode is a must-hear for anyone curious about the intersection of this growing technology and sales.

In this episode of Getting to Club, Chris takes you inside a recent negotiation, culminating in a $110,000 deal with significant expansion potential. He outlines four key lessons learned, including the power of a solid business case, the importance of differentiation, leveraging champions effectively, and the critical strategy of knowing when to walk away. This episode is a must-listen for anyone looking to refine their negotiation skills and understand the delicate balance between persistence and flexibility in sales.

In this episode of Getting to Club, Chris unveils a surprisingly simple yet profoundly effective strategy for skyrocketing your close rates. With a simple post-sale interview, you gain a better understanding of the intricate motivations, hidden objections, and internal selling processes of your buyers, which can nearly double your effectiveness in the market.