With weeks of prep work, exciting itineraries, and top-notch speakers, SKOs are usually an epicenter of excitement after a grueling end-of-year rush.But despite the traditional approach to designing SKOs as a rallying cry for motivation, they truly serve two main purposes: resetting and refocusing the team by providing clarity and creating energy, commitment, and movement around action items.Paul Stansik, operating partner at ParkerGale Capital returns to the show to discuss designing the most effective SKO. He wants CROs to focus in on two overlooked facets of a successful SKO: clarity and purpose, with follow-up. When your sales team doesn’t understand the main problem you’re trying to address or the strategy you’re implementing, it leaves them in a whirlwind of energy with no direction to point it in. And when you don’t build in touchpoints and reminders throughout the year, the SKO becomes just another event on the calendar. Particularly in a remote environment where SKOs may be the only opportunity to meet with teammates and collaborate, these events are crucial in assuring team-wide alignment and enabling sellers to show up with the right knowledge. Industry-rattling speakers are fantastic for rallying the team together, but without clarity, SKOs will fall flat. Join us as we discuss:The importance of balancing clarity and motivation, and how you can attain bothIdentifying and addressing the company's biggest bottlenecks as guiding factors in designing a stellar SKOBuilding collaboration and continuous improvement with mid-year meet-ups and hybrid approaches

A seller’s greatest enemy? It’s not “no.” It’s “We’ll see.” The average seller loses between 40% and 60% of their qualified pipeline to no decision. Matt Dixon, founding partner of DCM Insights and co-author of The Challenger Sale, The Effortless Experience, and The Challenger Customer. Matt and his co-author analyzed 2.4 million sales calls over the course of 18 months, which they turned into the definitive guide to overcoming customer indecision — The JOLT Effect. They dove into the underpinnings of no-decision losses, uncovering exactly how they happen and the surprising approaches that top-performing sales professionals take to shift customers out of hesitation and into action...In this bonus episode, Matt joins us to talk about what The JOLT Effect uncovered about buyer psychology and intent, the role fear of failure plays in customer indecision, and how sales teams can employ the JOLT Effect to push customers past their fear of failure to an unqualified yes.We discuss:The three major drivers behind the fear of failure that leads to no-decision losses (and how the JOLT process can help mitigate them)Creating flexible, shared decision-making for buyers while taking inaction off the tableCounterintuitive habits that set high performers apart from the rest

Cynthia Barnes, founder and CEO of the National Sales Network, discusses the importance of building an inclusive sales culture. Topics include the difference between equity and equality in DEI initiatives, practical measures to promote diversity, and why diversity matters in sales and marketing.

Game up on one screen, Discord on the other, thousands of people are connecting with one another at any given moment. Whether you like dodging red shells and drifting across iterations of rainbow road or you have an interest in specialized aircraft simulation, there’s an online community and gaming system for you.Evan Patterson, Marketing Consultant & Freelancer Marketer at Evan Patterson Consulting accidentally found his way into marketing through online gaming communities. His gatherings for gamers quickly grew and garnered the attention of gaming platforms, companies, and enthusiasts alike.Evan now uses his hands-on expertise in social selling to enable B2B SaaS companies to foster communities and connections with the same spark. He joined us to explain how social selling is best fueled by authentic connection, and how sales leaders can build healthy, high-performing teams by harnessing the power of social selling.We discuss:How a simple question can help leaders move beyond “equality” and toward true “equity.”How authentic allyship does (and doesn’t) show up in businessAddressing the skill, hill, or will challenge of social selling

Sales leaders, let’s try an exercise: if given a blank sheet of paper, can you write down three “superpowers” for each of your reps?The best sales leaders aren’t those who force reps to sell like them. Sales teams that consistently win lean into diversity through supportive leadership that enables psychological safety and amplifies individual strengths.By intentionally welcoming diverse voices into the room, these leaders bring more solutions to the table.In this episode, we’re joined by Chantel George, founder & CEO of Sistas In Sales, which she founded to bring the mentorship, opportunities, and networking, and training that she wishes she had when she started in sales to women from diverse backgrounds. Now with more than 5,000 members, Sistas in Sales hopes to build a more inclusive, well-rounded profession for generations to come.Join us as we discuss:Why failing to build a diverse sales team leaves important, problem-solving perspectives — and money— on the tableHow the best leaders trust their sellersWhy it’s important to build psychological safety

We’ve all heard that culture eats strategy for breakfast. But how can sales teams nurture a stronger culture among individual sellers? Start with mindset.Changing the way your organization sees its sellers—and the way those sellers see themselves—can unlock impressive sales growth. Our guest Catherine Brown, Founder of ExtraBold Sales, shares how managers can begin shifting away from the stereotype of sales people who push and coerce, and towards a culture that taps into each seller’s ‘why.’ After all, a strong culture is made up of thriving individuals—all of whom aregrowing toward the best version of themselves. In her recent book, How Good Humans Sell, Catherine breaks down the importance of enabling your sellers to develop into their best selves. Our conversation delves into her practical tips for building high performance ,starting at the granular human level.Join us as we discuss:Closing more sales with a simple shift in company mindsetWhy failing to coach your sellers is costing your businessHow to create highly-human interactions in the age of AIThe first steps to becoming an aspirational leader

Sales teams now see sales tech like Gong and Showpad as staples for high-performing organizations.But these platforms are just the beginning. Fringe tech, enabled by AI and cross-platform collaboration, can automate and streamline administrative tasks, freeing up your sales team to invest in, you know, selling. The robots aren’t coming for your sales team — but they are coming to help. Embracing innovative tech differentiates the best of the best from the average seller in the modern sales world.Jeff Rosset, founder and CEO of Sales Assembly, joined the show to discuss how leaders best leverage tech (tailored to their strategy and environment) to allow sales teams to dive deeper into social selling, better understand their prospects and hone new skills to emphasize and create authentic connections.In sales, AI and fringe tech aren’t just shiny tools to take up space in the stack — they create opportunities to calibrate and reach your full potential.Join us as we discuss:Opportunities to utilize tech for efficiency (and common misconceptions)What sets successful social selling teams apart from those who won’t make the cutThe future of tech in sales and beyond—tangible outcomes, increased attribution and empowered teams

Over the past few years, there have been astounding advancements in tech with no sign of slowing down—and we all have a choice to make: Terminator or Iron Man.As a sales leader (or any type of business leader, really), you have two options. You can choose to treat these innovations as a threat, run away and hide from technology, automation, and AI as if they are the Terminator, out for your job and livelihood. Or, you can embrace the superpowers these innovations can offer and become a modern business Iron Man.Danny Wasserman, Director of GTM Enablement at Gong says those who run and hide will be left behind. But those who embrace the endless possibilities and benefits of modern tech will be able to become the best version of themselves, ultimately elevating their personal and professional lives.When you leverage tech to gather, isolate and analyze data, you can identify strengths and weaknesses with ease and speed that has never before been possible.So which will it be—Terminator or Iron Man?Join us as we discuss:Achieving higher win rates by leveraging revenue intelligence and data analysisStriking a balance between standardizing practices and respecting regional differencesEmpowering sales professionals by encouraging self-reflection and embracing vulnerability

You're marching into battle, armored allies by your side. Together, you have to decide how to reign as champion, but to do that you have to share your knowledge. How much do you give away without revealing your biggest strategic strengths (and weaknesses)? After all, your ally in battle may also be your competition in other realms of life.Like allies on a battlefield, business partners must navigate prospects with precision, sharing data and insights as needed. But in reality, you only have 50% of the data you need to make an informed decision. Even the best partner in the world doesn’t want to share their entire customer list (let alone their whole pipeline). Bob Moore, Co-Founder and CEO at Crossbeam had a revolutionary idea—what if partners could exchange all the right data without giving away so much information they lose their strategic edge? Bob joins us to discuss how partners, like allies on a battlefield, can be enabled with data to win any war together, all while retaining individual privacy, security and compliance.We discuss:The importance and potential of partnership ecosystem-led growthAddressing tech stack fatigue by asking the right hard questionsIntegrating new sales tech in a way that enables legacy professionals

Truth bomb 💣 A lot of sellers fail because they fail to follow up.Your outbound can be on point, but unless it’s absolutely phenomenal, you’re not likely to close many deals with a single email. You’ve got to come back a few times, remind your buyer who you are, and show them exactly why they should execute your CTA. And guess what—tech can help without scaring prospects away with a robotic tone 🤖When is outbound a losing game? Is there a golden number of emails you should send? Craig Jordan, Founder and CEO at SaaScend and our guest on the latest episode of Winning the Challenger Sale podcast, says he won’t respond until he’s received four emails, at minimum. And more importantly—the intention and attention behind the email (seen with interesting, well-written, personalized copy) are much more important than whether robots are involved in the development.Join us as we discuss:Utilizing tech to power and personalize your communications (while avoiding complacency and tech stack fatigue)How to build a killer tech stack from scratch without overextending resourcesBuilding mentorship and collaboration into culture for cascading system success