The SalesHandicapper: Your Winning Edge

In this episode of Your Winning Edge, host Skip Balch speaks with Bobby Jacobs, Head of Growth at Thread, an AI-powered service desk built for IT service providers (MSPs).Bobby shares how Thread is redefining IT support with AI and what it takes to build a scalable, repeatable sales motion in a fast-evolving market. The conversation dives into the role of SDRs, the growing impact of AI on sales and marketing, and why delivering real customer value is the foundation of sustainable growth.You’ll also learn practical insights on hiring the right sales talent, setting clear expectations, and maintaining strong customer relationships while staying focused on your ideal customer profile.What you’ll learn in this episode:* How AI is transforming IT service providers and service desks* The importance of building a repeatable sales process* The role of SDRs in scaling outbound and inbound efforts* How AI is reshaping sales and marketing strategies* Why understanding customer needs is critical when selling AI solutions* Hiring strategies: why attitude and potential matter more than experience* The importance of setting clear expectations for sales teams* How to maintain strong customer relationships and retention* Why focusing on your ideal customer profile is essential for growthKey insights:* “We say death to the ticket.”* “You can’t hire work ethic.”* “It’s all about activity.”This episode is ideal for sales leaders, founders, MSP operators, and anyone looking to understand how AI is reshaping the future of IT services and go-to-market strategy.Timestamps:00:00 Introduction to Thread and Bobby Jacobs06:36 Building a Repeatable Sales Motion12:37 AI’s Impact on Sales and Marketing18:21 Hiring for Sales Success33:05 Customer Relationships and Ideal Customer ProfileSubscribe for more conversations on sales, growth, leadership, and AI.#AIinIT #MSP #SalesStrategy #B2Bsales #ArtificialIntelligence #TechSales #StartupGrowth #CustomerSuccess #YourWinningEdgeWe hope you enjoyed this episode of SalesHandicapper!– Skip and the SalesHandicapper Podcast team :)Connect with me: LinkedIn - https://www.linkedin.com/in/skipbalch/Listen to The SalesHandicapper on these podcast platforms: Spotify: https://open.spotify.com/show/6yfFwczRTqruBsyi3PMD7pApple Podcasts: https://podcasts.apple.com/podcast/the-saleshandicapper/id1878682655Amazon Podcasts: https://music.amazon.com/podcasts/4b791f16-e916-45cf-a66d-4efb324e24f3/the-saleshandicapper-your-winning-edge#SalesHandicapper #SkipBalch #B2BSales #SalesStrategy #TechSales #SalesLeadership #StartupSales #SalesProcess #ICP #PipelineManagement #SalesCoaching #RevenueGrowth #FounderSales #SalesEnablement #GTMStrategySalesHandicapper is a podcast for B2B tech founders and sales leaders building and scaling their sales engines. Hosted by Skip Balch, a sales strategist with over 45 years of experience in B2B sales and product development, each episode explores the real challenges of creating repeatable, scalable sales processes. Skip brings a diagnostic approach to sales, helping leaders distinguish between people problems, process problems, and ICP problems.The podcast features candid conversations with founders and sales leaders who share their journeys from early customer wins to scaling sales teams. Whether you're a founder systematising what's working, a VP of Sales managing inconsistent team performance, or a sales leader navigating the shift from early stage to scale, SalesHandicapper delivers practical frameworks and honest insights to help you build your winning edge.

In this episode of Your Winning Edge, host Skip Balch sits down with Sean Patrick Fleming, Head of Growth and Revenue at Aztra, to explore how businesses can successfully adopt AI and drive real ROI through decision intelligence.Sean shares how Aztra is bridging the gap between AI applications and implementation, helping companies move from experimentation to measurable outcomes. The conversation dives into the shift from service-based to product-based models, the true cost of AI, and why change management is critical for success.You’ll also learn how to navigate the AI adoption curve, align AI initiatives with business goals, and use data effectively to unlock growth and competitive advantage.What you’ll learn in this episode:What decision intelligence means and how it drives faster ROIThe real total cost of AI and how to justify investmentWhy most companies are still early in their AI adoption journeyHow to align AI projects with business goals for successThe importance of data quality in AI implementationWhy AI augments human roles instead of replacing themHow to slow down the sales process to better understand client needsStrategies for smaller firms to compete using AIThe role of curiosity and continuous learning in an AI-driven worldKey insights:“We focus on getting outcomes faster.”“Total cost of AI is often misunderstood.”“AI will augment people, not replace them.”“You need to understand the business DNA.”“AI is the great equalizer.”This episode is ideal for founders, sales leaders, and operators looking to leverage AI for business growth, improve decision-making, and stay competitive in a rapidly evolving market.Timestamps:00:00 Introduction to Aztra and AI Applications03:13 Transitioning from Services to Product05:59 Understanding Decision Intelligence and ROI08:54 Client Engagement and Adoption Challenges11:48 Total Cost of AI and Justifying ROI14:53 The Role of Change Management in AI Adoption17:58 Sean’s Background and Perspective20:51 Leveraging AI for Sales Efficiency24:08 Differentiating in an AI-Driven Market26:52 The Future of AI and Human Collaboration30:39 Understanding the Sales Process32:05 Navigating the AI Adoption Curve34:58 Identifying Business Use Cases for AI36:51 The Importance of Data in AI Implementation39:30 Aligning AI with Business Goals40:49 The Future of AI and Continuous Learning43:59 Fostering Curiosity in the Age of AI45:40 Leveraging AI for Business Growth50:54 Competing with Larger Firms Using AI52:29 The Unique Value Proposition of Small FirmsSubscribe for more insights on AI, sales, leadership, and business growth.#AI #DecisionIntelligence #ArtificialIntelligence #BusinessGrowth #SalesStrategy #AIOperations #DigitalTransformation #Leadership #StartupGrowth #YourWinningEdgeWe hope you enjoyed this episode of SalesHandicapper!– Skip and the SalesHandicapper Podcast team :)Connect with me: LinkedIn - https://www.linkedin.com/in/skipbalch/Listen to The SalesHandicapper on these podcast platforms: Spotify: https://open.spotify.com/show/6yfFwczRTqruBsyi3PMD7pApple Podcasts: https://podcasts.apple.com/podcast/the-saleshandicapper/id1878682655Amazon Podcasts: https://music.amazon.com/podcasts/4b791f16-e916-45cf-a66d-4efb324e24f3/the-saleshandicapper-your-winning-edge#SalesHandicapper #SkipBalch #B2BSales #SalesStrategy #TechSales #SalesLeadership #StartupSales #SalesProcess #ICP #PipelineManagement #SalesCoaching #RevenueGrowth #FounderSales #SalesEnablement #GTMStrategySalesHandicapper is a podcast for B2B tech founders and sales leaders building and scaling their sales engines. Hosted by Skip Balch, a sales strategist with over 45 years of experience in B2B sales and product development, each episode explores the real challenges of creating repeatable, scalable sales processes. Skip brings a diagnostic approach to sales, helping leaders distinguish between people problems, process problems, and ICP problems.The podcast features candid conversations with founders and sales leaders who share their journeys from early customer wins to scaling sales teams. Whether you're a founder systematising what's working, a VP of Sales managing inconsistent team performance, or a sales leader navigating the shift from early stage to scale, SalesHandicapper delivers practical frameworks and honest insights to help you build your winning edge.

In this episode of Your Winning Edge, host Skip Balch sits down with Michael Byrd to explore how AI is transforming sales leadership, sales management, and overall sales performance.Michael shares his journey from sales rep to Chief Revenue Officer and explains how AI is reshaping the way sales teams operate from lead qualification and CRM management to coaching and performance tracking. The conversation dives into how AI-driven intelligence engines are helping sales leaders make better decisions, improve efficiency, and gain a competitive edge.You’ll learn how data-driven sales strategies, machine learning, and automation are changing the sales landscape and what sales leaders need to do to stay ahead.What you’ll learn in this episode:How AI is transforming sales leadership and managementWhy data quality in CRM systems is critical for successHow AI improves lead qualification and prospect scoringThe role of AI in sales coaching and performance trackingHow automation reduces manual work for sales teamsWhy deal age is a key indicator of closing successHow AI creates a competitive advantage in salesThe future of sales roles in an AI-driven worldKey insights:“Garbage in, garbage out.”“AI has been behind it.”“The model will tell you that.”“You need to dive headlong into AI.”“It’s going to be critical.”This episode is perfect for sales leaders, founders, CROs, and anyone looking to leverage AI to improve sales performance, streamline processes, and stay competitive in a rapidly evolving market.Timestamps:00:00 Introduction to Sales Leadership and AI Innovations03:54 The Impact of AI on Sales Management08:16 Building an AI-Driven Intelligence Engine12:21 Transforming Sales Coaching with AI16:51 Engagement and Performance Tracking in Sales Teams22:50 Future Developments in AI for Sales24:07 Data-Driven Sales Strategies26:44 AI in Sales: Enhancing Lead Qualification30:31 The Future of CRM with AI34:10 Sales Management in the Age of AI38:47 Leveraging AI for Competitive Advantage40:34 AI’s Impact on Lead GenerationSubscribe for more insights on sales, AI, leadership, and growth.#AIinSales #SalesLeadership #SalesStrategy #B2Bsales #ArtificialIntelligence #CRM #SalesManagement #TechSales #BusinessGrowth #YourWinningEdgeWe hope you enjoyed this episode of SalesHandicapper!– Skip and the SalesHandicapper Podcast team :)Connect with me: LinkedIn - https://www.linkedin.com/in/skipbalch/Listen to The SalesHandicapper on these podcast platforms: Spotify: https://open.spotify.com/show/6yfFwczRTqruBsyi3PMD7pApple Podcasts: https://podcasts.apple.com/podcast/the-saleshandicapper/id1878682655Amazon Podcasts: https://music.amazon.com/podcasts/4b791f16-e916-45cf-a66d-4efb324e24f3/the-saleshandicapper-your-winning-edge#SalesHandicapper #SkipBalch #B2BSales #SalesStrategy #TechSales #SalesLeadership #StartupSales #SalesProcess #ICP #PipelineManagement #SalesCoaching #RevenueGrowth #FounderSales #SalesEnablement #GTMStrategySalesHandicapper is a podcast for B2B tech founders and sales leaders building and scaling their sales engines. Hosted by Skip Balch, a sales strategist with over 45 years of experience in B2B sales and product development, each episode explores the real challenges of creating repeatable, scalable sales processes. Skip brings a diagnostic approach to sales, helping leaders distinguish between people problems, process problems, and ICP problems.The podcast features candid conversations with founders and sales leaders who share their journeys from early customer wins to scaling sales teams. Whether you're a founder systematising what's working, a VP of Sales managing inconsistent team performance, or a sales leader navigating the shift from early stage to scale, SalesHandicapper delivers practical frameworks and honest insights to help you build your winning edge.

In this episode of Your Winning Edge, host Skip Balch sits down with Gary Tillery, the newly appointed CEO of Skkynet, to explore leadership, AI-driven growth, and the future of customer-centric technology businesses.Gary shares his journey from board advisor to CEO and breaks down Skynet’s strategic shift from a perpetual license model to a subscription-based revenue approach. The conversation dives deep into why secure data, customer trust, and operational excellence are non-negotiable in industrial and enterprise environments and how AI is reshaping everything from sales strategy to internal infrastructure.This episode also explores the human side of leadership. Gary explains why creativity, relationships, and hiring people with a servant’s heart are essential for scaling responsibly in an AI-powered world. From go-to-market strategy and free download models to building standardized processes that support long-term growth, this discussion offers practical insights for executives, founders, and technology leaders navigating rapid change.If you’re interested in AI strategy, leadership transitions, subscription business models, customer engagement, or building trust-driven technology companies, this episode delivers real-world perspective from the front lines.Topics covered in this episode include:Transitioning from board advisor to CEOShifting from perpetual licenses to subscription revenueCustomer engagement and long-term loyaltySecure data and trust in industrial applicationsAI’s impact on operations, creativity, and leadershipGo-to-market strategy and sales executionHiring for values, culture, and servant leadershipBuilding scalable infrastructure and standardized processesBalancing automation with human connectionSubscribe to Your Winning Edge for in-depth conversations with leaders shaping the future of business, technology, and growth.We hope you enjoyed this episode of SalesHandicapper!– Skip and the SalesHandicapper Podcast team :)Connect with me: LinkedIn - https://www.linkedin.com/in/skipbalch/Listen to The SalesHandicapper on these podcast platforms: Spotify: https://open.spotify.com/show/6yfFwczRTqruBsyi3PMD7pApple Podcasts: https://podcasts.apple.com/podcast/the-saleshandicapper/id1878682655Amazon Podcasts: https://music.amazon.com/podcasts/4b791f16-e916-45cf-a66d-4efb324e24f3/the-saleshandicapper-your-winning-edge#SalesHandicapper #SkipBalch #B2BSales #SalesStrategy #TechSales #SalesLeadership #StartupSales #SalesProcess #ICP #PipelineManagement #SalesCoaching #RevenueGrowth #FounderSales #SalesEnablement #GTMStrategySalesHandicapper is a podcast for B2B tech founders and sales leaders building and scaling their sales engines. Hosted by Skip Balch, a sales strategist with over 45 years of experience in B2B sales and product development, each episode explores the real challenges of creating repeatable, scalable sales processes. Skip brings a diagnostic approach to sales, helping leaders distinguish between people problems, process problems, and ICP problems.The podcast features candid conversations with founders and sales leaders who share their journeys from early customer wins to scaling sales teams. Whether you're a founder systematising what's working, a VP of Sales managing inconsistent team performance, or a sales leader navigating the shift from early stage to scale, SalesHandicapper delivers practical frameworks and honest insights to help you build your winning edge.

 If you've ever tried to buy commercial insurance as a small business and felt ignored, overcharged, or just confused about what you were even buying - this episode was made for you. Nick Del Biaggio joins Skip Balch to explain how the first native AI insurance brokerage is flipping the traditional model on its head and why it couldn't have happened until now.Nick has spent over 25 years in insurance brokerage sales and leadership. When he saw how fast AI was moving and how far behind the industry was, he made the jump to a Y Combinator-backed startup built from the ground up on AI infrastructure, operating across all 50 states and laser-focused on the small to medium businesses that legacy brokers have been ignoring for decades.In this episode, they break down why small businesses get the worst deal in commercial insurance, what 97% automation actually looks like in a brokerage, how they went from helping a taco shop in North Carolina get liquor liability in a single morning to building toward a billion-dollar company, and what the future of the sales role looks like when AI handles everything except the human conversation.If you're a small business owner, a CRO at a startup, or anyone trying to understand how AI is reshaping an industry that's been running on 1980s infrastructure, this one is worth your time.Key takeaways:The traditional brokerage model was built to bundle or ignore you. If your policy only pays a broker $50-100, don't expect a callback. AI changes the economics so that small accounts are worth serving properly.97% automation is already a reality. What used to require constant human intervention - gathering requirements, matching carriers, issuing certificates - is now handled by AI, with humans stepping in only where judgment and conversation are needed.Small businesses are buying the wrong coverage. Most owners don't know what their policy actually covers or what they're self-insuring. The job is to educate first, sell second.AI can scan a contract and tell you exactly what coverage you need. No more sending documents to your broker and waiting three days while a deadline passes.The future of sales is storytelling and empathy. When AI removes the administrative burden, you can hire for people skills - the ability to explain complex things simply and make clients feel genuinely cared for.Don't out-kick your coverage as you scale. The biggest challenge isn't growth, it's making sure infrastructure can handle the volume. Building that correctly is the job.Get your hands dirty as a CRO. Learn every part of the business, sit with the engineers, understand the full sales cycle - because when something is off, you need to know where to go and who to call.Today is the worst day AI is ever going to be. The industries slowest to evolve are the biggest opportunities. If you've been displaced by AI, look at where your experience meets an industry that hasn't caught up yet.Connect with Nick Del Biaggio on LinkedIn:linkedin.com/in/nick-del-biaggioChapters:0:00 Introduction0:58 How Nick made the jump to Harper Insurance2:49 Why the insurance industry is ripe for AI disruption4:02 Serving the underserved: small business insurance in America5:30 Real example: the taco shop that needed liquor liability by 3:30pm6:58 Reversing the 90/10 rule: 97% automation at Harper8:17 36 million underserved businesses in the US11:25 Building a go-to-market team in Silicon Valley's AI gold rush12:35 The unexpected calibre of candidates applying to a startup14:17 How many salespeople and what does the role look like?15:24 Why top talent wants to work 15-hour days at Harper18:14 The salesperson as trusted advisor, not policy pusher20:06 Partnership opportunities: CPAs, referral channels and beyond21:04 The age modelling problem in traditional insurance brokerage24:08 Real talk: can Harper get you a cheaper policy?25:47 Harper's biggest messaging challenge27:36 The number one sales challenge: infrastructure keeping up with growth29:33 Marrying tech startup thinking with insurance expertise30:33 Operational excellence, customer intimacy and what AI unlocks34:09 Hiring for storytelling, not just credentials38:27 Why everyone can relate to the insurance problem39:46 The math plus commitment equation41:23 Advice for small businesses: give Harper a shot42:38 Advice for fellow CROs: get your hands dirty44:43 Closing thoughts and what's next for Harper We hope you enjoyed this episode of SalesHandicapper!– Skip and the SalesHandicapper Podcast team :)Connect with me: LinkedIn - https://www.linkedin.com/in/skipbalch/Listen to The SalesHandicapper on these podcast platforms: Spotify: https://open.spotify.com/show/6yfFwczRTqruBsyi3PMD7pApple Podcasts: https://podcasts.apple.com/podcast/the-saleshandicapper/id1878682655Amazon Podcasts: https://music.amazon.com/podcasts/4b791f16-e916-45cf-a66d-4efb324e24f3/the-saleshandicapper-your-winning-edge#SalesHandicapper #SkipBalch #B2BSales #SalesStrategy #TechSales #SalesLeadership #StartupSales #SalesProcess #ICP #PipelineManagement #SalesCoaching #RevenueGrowth #FounderSales #SalesEnablement #GTMStrategySalesHandicapper is a podcast for B2B tech founders and sales leaders building and scaling their sales engines. Hosted by Skip Balch, a sales strategist with over 45 years of experience in B2B sales and product development, each episode explores the real challenges of creating repeatable, scalable sales processes. Skip brings a diagnostic approach to sales, helping leaders distinguish between people problems, process problems, and ICP problems.The podcast features candid conversations with founders and sales leaders who share their journeys from early customer wins to scaling sales teams. Whether you're a founder systematising what's working, a VP of Sales managing inconsistent team performance, or a sales leader navigating the shift from early stage to scale, SalesHandicapper delivers practical frameworks and honest insights to help you build your winning edge.

If your sales team is drowning in admin work and you keep hearing about AI agents but have no idea where to actually begin, this episode is for you. Sales enablement veteran Donna McCurley joins Skip Balch to break down why most companies jump straight into complex AI workflows and end up with systems that hallucinate, break, and get abandoned - and what to do instead.Donna has spent over 20 years building dynamic sales enablement programs, taught AI agent-building at Microsoft, and now helps sales organizations cut through the noise by starting simple and building trust one agent at a time.In this episode, they get into the real difference between on-demand and autonomous agents, why your CRM data is probably not ready for what you think you want, how to actually calculate the ROI of bringing AI into your sales process, and what the sales org of 2026 looks like when humans and AI work side by side.If you're a CRO, sales leader, or enablement professional trying to figure out where AI fits without blowing up your team's trust or your budget, this is a conversation you need to hear.Key takeaways:Start with on-demand agents before you touch autonomous workflows. Build one, test it, make sure it works, then connect them. Skipping this step is why most AI implementations fail.AI is best deployed on non-revenue-producing tasks first. Research, follow-up emails, client onboarding questionnaires - these are where you win time back fast and build team buy-in.You don't need perfect data to get started. Think of it like kindergarten - you find out what you have, identify the gaps, and build a roadmap from there.Benchmark everything before you build. Donna won't deploy an agent without first measuring what the current process costs in time and headcount. That's how you prove ROI.Sellers need to trust the agent before it touches the CRM. Rushing integration before your team believes in the tool is one of the fastest ways to kill adoption.A proof of concept should always be paid. If a prospect won't invest in a POC, they're not serious about moving forward.The future sales team is human plus AI, not one replacing the other. The role is evolving, not disappearing - think of it as the next layer, like when computers first landed on every desk.Find a consultant who enables, not just delivers. The goal should be teaching your team how to build and maintain agents, not outsourcing it and losing the knowledge when the engagement ends.Follow Donna McCurley on LinkedIn and reach out to explore how she works with sales organizations to build AI agents the right way:linkedin.com/in/donnamccurleyChapters: 0:00 Introduction1:52 Why static sales enablement fails sellers3:29 How Donna started her AI consulting business6:40 What is an AI agent?10:06 The data compliance problem in sales12:13 Why on-demand agents come before autonomous workflows14:33 What to do when you don't have SOPs16:02 Workstream 2: building agents and enabling the team16:40 Real client example: the event onboarding agent19:45 Using agent data to spot opportunity risk23:08 CRM integration and the trust-first approach24:15 How prospects are thinking about AI right now30:30 AI as authorship at scale33:01 How to quantify ROI from AI time savings36:10 Why Donna charges for proof of concepts37:21 Why she wins: compound interest over speed44:18 Workstream 3: autonomous agents46:13 The future of the sales role48:05 Will AI reduce headcount?49:12 Earning trust before everything else56:26 Closing adviceWe hope you enjoyed this episode of SalesHandicapper!– Skip and the SalesHandicapper Podcast team :)Connect with me: LinkedIn - https://www.linkedin.com/in/skipbalch/Listen to The SalesHandicapper on these podcast platforms: Spotify: https://open.spotify.com/show/6yfFwczRTqruBsyi3PMD7pApple Podcasts: https://podcasts.apple.com/podcast/the-saleshandicapper/id1878682655Amazon Podcasts: https://music.amazon.com/podcasts/4b791f16-e916-45cf-a66d-4efb324e24f3/the-saleshandicapper-your-winning-edge#SalesHandicapper #SkipBalch #B2BSales #SalesStrategy #TechSales #SalesLeadership #StartupSales #SalesProcess #ICP #PipelineManagement #SalesCoaching #RevenueGrowth #FounderSales #SalesEnablement #GTMStrategySalesHandicapper is a podcast for B2B tech founders and sales leaders building and scaling their sales engines. Hosted by Skip Balch, a sales strategist with over 45 years of experience in B2B sales and product development, each episode explores the real challenges of creating repeatable, scalable sales processes. Skip brings a diagnostic approach to sales, helping leaders distinguish between people problems, process problems, and ICP problems.Whether you're a founder systematising what's working, a VP of Sales managing inconsistent team performance, or a sales leader navigating the shift from early stage to scale, SalesHandicapper delivers practical frameworks and honest insights to help you build your winning edge.

Marketing agencies are facing an extinction event. According to Jon Tsourakis, President and Chief Revenue Officer of Oyova, 20 percent or more of marketing agencies will disappear within two years as AI reshapes the industry. But the agencies that survive won't just adapt to technology - they'll double down on deep expertise, team selling, and genuine curiosity.Jon shares battle-tested insights from leading a 30-person marketing and development agency through massive market shifts. From the death of content mills to why he fires clients who don't respect his team, this conversation reveals what it really takes to win in today's brutally competitive agency landscape. Skip and Jon dig into the realities of losing deals to insiders, why price objections mean you already lost, and the surprising power of walking away from bad-fit prospects.If you're selling complex services in a commoditized market, this episode delivers hard-won wisdom on qualification, team-based selling, and building a sales process tight enough that clients feel zero pain from discovery to delivery.Key learnings: Why most marketing agencies will disappear in the next two years and which ones will surviveThe real reason agencies lose deals and why price is never the actual problemHow to qualify ruthlessly so you stop wasting time on deals you'll never closeWhy flying out to meet prospects in person still wins deals in the Zoom eraThe one question that reveals true urgency in every sales conversationHow curiosity became the most valuable trait in modern salespeopleWhy Jon fires clients who don't deserve to get rich from his team's workThe framework for team selling that protects both your salespeople and your delivery teamHow to reposition competitors without ever talking about your own solutionWhat makes a sales process so tight that clients experience zero frictionWant more insights on building your competitive edge in sales? Follow Your Winning Edge and connect with Skip Balch.Jon TsourakisPresident & Chief Revenue Officer, Oyovahttps://www.linkedin.com/in/[email protected]:0:00 Introduction1:03 Why 20% of marketing agencies will disappear2:01 What happened to inbound-focused agencies4:00 Deep expertise as a survival strategy5:07 The final 10%: why clients come back to experts7:09 Positioning and the danger of patching yourself together8:17 What deep expertise actually means at Oyova9:48 The biggest sales challenge: getting to the decision maker10:44 Why team selling wins over solo selling12:10 How Jon structures the sales meeting13:47 Why Oyova loses: price and US-based labor costs14:40 Why getting on a plane can make or break a deal16:57 Qualify to disqualify: price conversations upfront18:47 What is Oyova's winning edge?20:02 How references and stories close deals21:16 How to hire for gratitude and attitude22:27 Where leads actually come from22:52 State of the business and optimism for 202626:13 You can't teach curiosity: what to look for in salespeople27:40 Curiosity as the fuel of AI28:54 How Jon opens a sales conversation30:49 Qualification is not a stage, it's the whole process34:42 The real reason companies don't buy35:09 Losing to insiders: the toughest deal to win37:20 The power of walking away from a deal40:14 When to send a prospect to your competitor41:33 Repositioning your competitor instead of yourself41:47 Jon's question to leave the audience withListen to The SalesHandicapper on these podcast platforms: Spotify: https://open.spotify.com/show/6yfFwczRTqruBsyi3PMD7pApple Podcasts: https://podcasts.apple.com/podcast/the-saleshandicapper/id1878682655Amazon Podcasts: https://music.amazon.com/podcasts/4b791f16-e916-45cf-a66d-4efb324e24f3/the-saleshandicapper-your-winning-edgeWe hope you enjoyed this episode of SalesHandicapper!– Skip and the SalesHandicapper Podcast team :)Connect with me: LinkedIn - https://www.linkedin.com/in/skipbalch/#SalesHandicapper #SkipBalch #B2BSales #SalesStrategy #TechSales #SalesLeadership #StartupSales #SalesProcess #ICP #PipelineManagement #SalesCoaching #RevenueGrowth #FounderSales #SalesEnablement #GTMStrategySalesHandicapper is a podcast for B2B tech founders and sales leaders building and scaling their sales engines. Hosted by Skip Balch, a sales strategist with over 45 years of experience in B2B sales and product development, each episode explores the real challenges of creating repeatable, scalable sales processes. Skip brings a diagnostic approach to sales, helping leaders distinguish between people problems, process problems, and ICP problems.The podcast features candid conversations with founders and sales leaders who share their journeys from early customer wins to scaling sales teams. Whether you're a founder systematising what's working, a VP of Sales managing inconsistent team performance, or a sales leader navigating the shift from early stage to scale, SalesHandicapper delivers practical frameworks and honest insights to help you build your winning edge.