Getting to Club

Most revenue enablement teams are guilty until proven revenue positive and right now, most can't prove it.In this solo episode, Chris Orlob breaks down why "vanity enablement" is about to go the way of vanity marketing, shares two real stories of CROs and CEOs taking a hacksaw to their enablement orgs (17 people cut to 4, 6 cut to 1), and lays out the only path forward: re-positioning enablement as revenue risk management.If you lead enablement, run a revenue org, or sit on a board asking why your enablement spend isn't showing up in the P&L, this one's a gut-check.Chris explains how AI is finally making skill and capability measurable, why that single shift rebuilds the entire power structure of the function, and what it sounds like when an enablement leader walks into a QBR speaking the language of dollarized skill gaps instead of training completion rates.

Most sellers were taught to surface a problem and then ask some version of "so how is that impacting the business?"Chris Orlob argues that question is the fastest way to sound generic, cheesy, and a little manipulative, even when the theory behind it (SPIN's implication questions, building urgency) is right.In this solo episode, Chris breaks down consequence mapping: a discovery skill where you pre-map the two to three predictable consequences that follow each problem you solve or persona you sell to, then lead with those consequences as a point of view.

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.

The SDR role has changed more in the last 24 months than in the previous decade.AI flooded the market with outbound noise, buyers stopped responding, and an entire generation of SDRs got "developed" through remote work, a pandemic, and almost zero coaching.The result is a skills crisis most teams haven't named yet - pipeline that looks healthy on the dashboard but doesn't convert, a handful of star performers carrying everyone else, and unpredictable pipeline generation no matter how much tech you stack on top.In this episode, Chris walks through the 2026 State of SDR Skills Report - the 10 skills defining the new standard of SDR performance - built with input from an industry council including Kevin Dorsey, Kyle Coleman, Kyle Norton, and Emily Worrell.If you lead an SDR or pipeline gen function, this is the diagnostic lens you've been missing.

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.

Chris Orlob breaks down seven lessons from personally closing a multi-six-figure deal with the CEO of a $1B+ company - in under 30 days.From positioning that made the CEO come to him, to leading the buying process, diagnosing instead of discovering, and why opinionated proposals win at the top.A tactical playbook for anyone selling complex deals to senior executives

Going upmarket is the single biggest valuation lever most B2B tech companies have at their disposal and most of them blow it.In this episode, Chris Orlob walks through the 11 non-negotiable AE skills that separate companies who successfully break into the enterprise from those stuck in mid-market prison.His core argument: upmarket success is determined by the capability floor of your revenue team, not your best rep, which is why "just hire a rainmaker" strategies produce a few big deals and then stall.Chris organizes the 11 skills into three pillars: unlocking, navigating, and closing the enterprise deal and turns the episode into a diagnostic you can run against yourself or your team.Identify four-plus gaps and your upmarket motion is already at risk; six or more and it'll break before it gets off the ground.Timestamps(00:50) Why most upmarket attempts make the business worse(04:43) The acid test: what "going upmarket" actually means(07:30) The 3 pillars and how to use this episode as a diagnostic(08:30) Skills 1 & 2 - Multi-threaded and multi-channel prospecting(13:00) Skill 3 - POV formation (with the HubSpot inbound example)(17:30) Skill 4 - Discovery that creates value, not just takes it(22:00) Skills 5 & 6 - Champion development and access to power(27:00) Skill 7 - Economic buyer alignment (not approval)(31:30) Skill 8 - Mutual action plan orchestration(35:45) Skill 9 - CFO-worthy business cases(39:45) Skill 10 - Navigating enterprise closing motions(43:00) Skill 11 - Negotiating with business acumen(45:30) Why you can't hire your way into the enterprise

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!

Welcome to Revenue Rewired!The conversation delves into the shift in demand from positive to negative, impacting the sales environment and requiring upskilling of sales reps and leaders. It explores the importance of building sales skills and systems, selling against the competition, and providing consistent and daily reinforcement. The traits of elite sales reps, the use of volume, signal data, and outbound strategies, the art of discovery, and the screening of traits in sales reps are also discussed.TakeawaysDemand has shifted from positive to negative, requiring sales reps to upskill and leaders to be more cognizant of their teams.Top 1% of reps control the deal, set the agenda, define next steps, and force clarity on the decision process.The best sales reps ignore internal and deal noise, focus on high-value selling conversations, and qualify opportunities ruthlessly.Chapters00:00 The Shift in Demand and Upskilling05:07 Selling Against the Competition10:46 Traits of Elite Sales Reps22:15 The Art of Discovery

I recently found out that our win rates jump from 42% to 68% when we are multi-threaded across THREE or more people. Access from one to two people makes no difference. 3-4 is where we make our money.This led us to codify five multi-threading "plays" we now use based on the situation. Here they are for you to steal or experiment with.

Register for the 2025 Skill Stacker Awards contest and ceremony here: https://www.pclub.io/skill-stacker-awardsIn this episode, Chris Orlob announces the first annual SkillStacker Awards, a contest designed for B2B sales professionals. The awards will recognize top sellers, transformational stories, and various categories within the sales profession. The event will kick off on February 13, 2025, with opportunities for participants to win prizes, including a trip to Fiji. Chris encourages listeners to join the live event and highlights the importance of recognition in the sales industry.TakeawaysThe SkillStacker Awards are open to all B2B sales professionals.The contest will run throughout 2025, culminating in an awards ceremony.Categories include top sellers, rookie of the year, and mentor of the year.Participants can win a trip for two to Fiji for the best success story.Recognition can enhance a sales professional's resume and career.The event will feature success stories from 2024.Chris emphasizes the fun and competitive nature of the awards.Joining the email list is crucial for updates and participation.The awards aim to celebrate skill transformation in sales.This initiative will be an annual event, building on its success each year.

In this episode, Chris Orlob discusses the importance of setting clear revenue goals for 2025 and the math behind achieving those goals. He emphasizes the need for sales professionals to calculate their required opportunities and contacts to reach their desired income, while also highlighting the significance of clarity in motivation and success in sales. Takeaways People are feeling cautiously optimistic in the sales world. Setting clear revenue goals is crucial for success. Calculate how much revenue you want to close. Understand your average deal size to determine the number of deals needed. Identify your close rate to calculate required opportunities. Break down annual goals into monthly and weekly targets. Reach out to a specific number of contacts to generate opportunities. Improving sales skills can positively impact conversion rates. Clarity in goals enhances motivation and performance. Sales success is a simple math equation when broken down.

In this conversation, Chris Orlob reflects on his journey of success and ambition, sharing insights about the importance of acknowledging and celebrating achievements. He discusses a limiting belief that prevented him from appreciating his successes, fearing it would lead to complacency. Through self-reflection, he realizes that recognizing accomplishments fuels motivation and ambition rather than diminishing it. Orlob encourages listeners to take pride in their achievements and to avoid glossing over their successes, as this acknowledgment is crucial for continued growth and motivation.

In this episode of the Getting to Club podcast, Chris Orlob discusses effective strategies for discussing price in B2B sales. He emphasizes the importance of context when presenting price to avoid sticker shock and maintain trust with potential buyers. The conversation outlines the worst and best practices for discussing price, providing actionable insights for sales professionals.

In this conversation, Chris Orlob discusses the detrimental effects of passively awaiting decisions in sales, recruitment, and funding scenarios. He emphasizes the importance of actively influencing outcomes rather than waiting for verdicts, sharing practical strategies to engage with potential customers and candidates effectively. By adopting a proactive approach, individuals can significantly improve their chances of success in various decision-making processes.

In this conversation, Chris Orlob discusses the critical distinction between ROI as a justification for demand rather than a creator of it. He emphasizes that while ROI can validate a purchase decision, it does not generate the initial desire or need for a product or service. The discussion highlights the importance of creating demand through understanding customer pain points and building urgency, rather than relying solely on ROI metrics. Orlob provides actionable insights for sales professionals on how to effectively uncover and amplify demand, ultimately leading to more successful sales outcomes.

This this lesson, you're going to learn the sales world's newest and most powerful concept: "Negative impact/market fit." Just as with "product/market fit," you can find a repeatable set of negative impact questions that predictably resonate with your target buyers. When you master this skill, you will see results in your bank account in 30 days or less. If you want to take the full course on Mastering Negative Impact so you can accelerate urgency and close more deals, head over to www.pclub.io and sign up as an individual. From there, you'll have instant access to this course and can start growing your income and bank account immediately. Enjoy!

In this lesson, you get access to the first lesson in our new Mastering Negative Impact course in pclub.io for free-99. You'll see an exact, word for word breakdown (actual sales conversation) of a rep using negative impact questions to create urgency where none existed before. If you want to take the entire course, you can sign up for pclub.io right here: https://www.pclub.io/platinum-passport

In this episode of the Getting to Club podcast, Chris Orlob shares his top three tips for new Sales Development Representatives (SDRs) looking to advance their careers in SaaS and technology sales. He emphasizes the importance of defining one's next role, dedicating time to skill development, and the necessity of hard work to achieve success. Through personal anecdotes and insights, Chris provides a roadmap for SDRs to elevate their careers and achieve exceptional results.

In this episode, Chris Orlob discusses insights from analyzing over a million sales calls, highlighting two conflicting data points regarding the number of questions to ask during discovery calls, especially with C-suite executives. He emphasizes the importance of preparation and crafting context-led questions to engage effectively with high-level decision-makers.

In this episode of the Getting to Club podcast, Chris Orlob shares 52 habits of successful salespeople who earn $350,000 or more annually. The discussion covers key strategies, mindset shifts, and personal development techniques that can help sales professionals elevate their performance and achieve greater success in B2B sales. Chris emphasizes the importance of continuous learning, effective selling strategies, and the development of essential skills such as negotiation and storytelling.

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.

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 delves into the intricacies of selling to the C-suite and what you can learn from the strategies of million-dollar earners who excel in this high-stakes arena. Chris breaks down five pivotal techniques bolstered by real-life examples that offer valuable lessons in engaging effectively with upper management.

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.

In this episode of Getting to Club, Chris delves into a foundational concept for sales success: the chain link system of skills. True sales mastery isn't about excelling in just one area, but rather improving incrementally across a spectrum of skills—discovery, negotiation, objection handling, and more. Success is about how these skills interlock and strengthen each other, limiting the impact of weaknesses and enhancing overall performance.

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 dives into the most common misconceptions and flat out lies surrounding SaaS discovery today. We'll challenge common practices and shares insights on how discovery should create value for both salespeople and their clients, rather than just gathering information for a sales pitch. Follow along to elevate your sales strategies and learn why great discovery is the key to success.

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 tackles a common yet critical issue facing sales teams: ineffective meetings. With insights drawn from Shawn Gentry's pclub.io course, Chris lays out a five-step agenda that promises to transform the way sales meetings are conducted. Discover how to make your sales meetings productive and engaging, ensuring your team is motivated, informed, and ready to excel in their roles.

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.

In this episode of Getting to Club, Chris explains how a simple yet profound question can unlock the true potential of a lead by transporting them back to the decisive meeting that initiated their search for a solution. With practical advice on when and how to deploy this question, Chris ensures you're equipped to deepen your discovery process and engage your buyers more effectively.

In this episode of Getting to Club, Chris tackles a common yet counterproductive practice among sales leaders: dominating sales calls. He outlines five compelling reasons why taking over sales calls from reps is detrimental, emphasizing the long-term impact on team development, rep dependency, and leadership growth. This episode is a must-listen for sales leaders and managers aiming to build resilient and autonomous teams capable of driving success without constant oversight.

In this episode of Getting to Club, Chris unveils his seven predictions for SaaS sales in 2024, drawn from over 300 discussions with Chief Revenue Officers and VPs of Sales. As the sales landscape evolves, Chris breaks down the anticipated shifts in decision-making, the heightened scrutiny on purchases, and the expanding complexity of buying committees. This forward-looking episode is a must-listen for anyone looking for help navigating the challenges and opportunities of the coming year.

In this episode of Getting to Club, Chris sheds light on why SMB sales reps often out-earn their enterprise counterparts. He explores market demands, compensation plans, and the strategic advantages of SMB roles over enterprise positions that can result in outsized returns. This episode is perfect for sales professionals aiming to maximize their earnings and career opportunities.

In this episode of Getting to Club, Chris debunks the common sales mantra that optimism is the key to success, especially in B2B sales. Great salespeople adopt a mindset of short-term pessimism and long-term optimism, allowing them to realistically assess risks and manage expectations. This episode is a deep dive into the psychological dynamics of sales, offering listeners actionable strategies for more thoughtful, effective selling.

In this episode of Getting to Club, Chris discusses the undeniable link between sales proficiency and achieving monumental success, illustrated through engaging stories, including a conversation with a highly successful CEO. This episode is a must-listen for anyone looking to elevate their sales game and achieve their professional goals.

In this episode of Getting to Club, Chris introduces a new approach to selling with benefits vs. pain: selling benefits that are at least 2x better than what the buyer currently has, using vivid examples from technology to everyday consumer decisions. Discover how to make your product irresistibly compelling by offering unparalleled value, and why settling for marginal improvements might not cut it in today's market.

In this episode of Getting to Club, Chris delves into the sales secrets that could have boosted his earnings a decade earlier. He shares timeless insights on targeting the right prospects, the crucial difference between solving problems and capitalizing on opportunities, and the unparalleled advantage of selling to power. This episode is a treasure trove for anyone looking to elevate their sales game and unlock their true earning potential.

In this episode of the Getting to Club podcast, host and pclub.io CEO Chris Orlob delves into the psychology of fairness in sales negotiations. Using compelling research and real-world examples, Chris explores how our innate desire for fairness can sometimes hinder achieving optimal outcomes. The episode offers a thought-provoking perspective on how re-evaluating our approach to fairness can lead to more successful deals. Tune in for a powerful blend of research and practical advice that can transform your sales strategy.

In this episode, Chris focuses on maximizing productivity through energy management. Chris discusses the four types of energy - physical, emotional, mental, and spiritual - and their profound impact on sales success. He shares insightful tips on enhancing each energy type for optimal performance. Join us for an enlightening journey to elevate your sales game and achieve top results.