Saleshandicapper: Your Winning Edge

Skip Balch, The SalesHandicapper

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Management

One

17 Aug

Software for Doing Good

Sales training does not end when onboarding ends. That is one of the biggest takeaways from my conversation with @Danielle Stinson-Hill, Chief Revenue Officer at @FrontStream. Danielle leads a remote sales team selling into one of the toughest markets imaginable: nonprofits. Her reps face limited budgets, crowded competition and a job that is 75% outbound leads! Yet her average salesperson stays far longer than the SaaS industry average. Why? They do not confuse training with learning. Danielle’s team: Role-plays constantlyRecords and reviews sales callsUses AI to uncover missed questionsMeasures coachability during onboardingApplies feedback on the very next callReceives clear expectations from day one Her message to sales leaders was direct: “If I can’t show them how to do their job in real time, there’s a problem.” I agree. A sales manager does not earn credibility through a title. You earn it by knowing how to diagnose a call, ask the next question and demonstrate what better looks like. Training is an event. Coaching is a management discipline. Your salespeople do not need another person telling them what to do. They need a leader who will show them how, watch them try, provide specific feedback and stay with them until they get it right. If your team is underperforming, look at the coaching before blaming the players.
27 Jul

Selling Tacos or Software - same difference

Discover the simple yet game-changing secret to scaling a hospitality brand — and why putting your personal phone number on every receipt might be the smartest move you make. In this eye-opening episode, Anthony Valletta, CEO of Bartaco, reveals how a genuine, human connection—not sophisticated algorithms—can transform your customer experience, foster loyalty, and drive growth. His bold approach to accessibility and vulnerability has built a brand that doesn’t chase trends but instead creates superfans through authentic engagement. Anthony shares how he personally interacts with guests, managing dozens of locations and thousands of employees without losing the soul of his brand. You'll discover: Why direct, real-time feedback from guests is more valuable than endless surveys or digital reviewsHow vulnerability and transparency foster trust and long-term loyalty in an industry increasingly dominated by automated servicePractical strategies for empowering your team to recover from mistakes in ways that turn guests into raving fansThe importance of creating frictionless, customer-first experiences that prioritize human connection over technologyHow wage equity, genuine hiring criteria, and investing in your team’s growth set the foundation for scalable success In a fast-paced, tech-driven world, this episode highlights the timeless power of authenticity, emotional connection, and servant leadership. If you're a sales leader, entrepreneur, or hospitality professional eager to stand out by building real relationships — not just transactions — this conversation is for you. Who should listen: Business owners and leaders questioning the reliance on tech or algorithms, founders craving authentic customer loyalty, and anyone interested in elevating human connection in their brand’s growth. Why it works: This episode combines a compelling, relatable story with practical lessons grounded in humility and vulnerability, inviting listeners to rethink how they engage with customers and teams. The secret isn’t slick tech; it’s heartfelt authenticity. Dive in and discover how a personal touch can be your ultimate growth strategy.
16 Jun

Your Winning Edge with Darryl Worsham

When does your moat stop protecting the castle? When everyone has a boat. For GAP Velocity AI, the moat was never the legacy software they modernized. The moat was 30 years of expertise, proprietary tools, proven delivery methods, and people who knew how to move clients from old codebases into modern cloud-native applications. Then AI changed the economics. Work that once took 12 to 15 months can now happen in 4 to 6 months. Investment requirements can drop by 70% to 75%. Fewer people are needed to do the same work. That creates a major opportunity. It also attacks a major revenue model built around people-heavy delivery. So the real transformation is not technical. It is human. Darryl Worsham called it “human engineering,” and that may be the best phrase in the entire conversation. Because when AI changes the tools, leaders still have to change the people. They have to help engineers move from skepticism to experimentation. They have to help teams stop protecting the old model and start owning the new one. They have to reset expectations, retrain talent, rebuild process, and create enough trust for people to walk into a future they did not choose. That is change management. That is leadership. That is the new moat. Once everyone has access to similar technology, the difference is no longer the tool. The difference is the team that knows how to use it, the leaders who know how to guide the transition, and the judgment to know what should change, what should stay, and what risk has to be managed. AI did not eliminate GAP Velocity AI’s advantage. It forced the company to move the moat from tools and labor to expertise, trust, execution, and human engineering. #YourWinningEdge #AITransformation #HumanEngineering #ChangeManagement #SalesLeadership #LegacyModernization #BusinessTransformation #RevenueLeadership
10 Jun

Saleshandicapper - Your Winning Edge with Chris Lee

AI is not killing SaaS. It is forcing SaaS companies to adapt, prove value, and stop hiding behind old growth stories. In this episode of Your Winning Edge, I sit down with Chris Lee, former CRO of enteros.ai and a revenue leader who has been inside some of the biggest SaaS shifts of the last 25 years, including Siebel, Salesforce, and DocuSign. We talk about what has changed, what has not, and what sales leaders better understand fast. Chris brings a clear message: Nothing really dies. It adapts. We dig into: • Why lead generation and retention still make or break revenue growth • Why customer feedback is useless if you do nothing with it • How AI helps companies spot risk, trends, and value gaps earlier • Why salespeople still need likability, trust, and real conversation skills • Why companies promote too many sellers into leadership too soon • How CEOs should use provocative ideas to test the market and shape demand This is not another “AI changes everything” conversation. It is a practical look at how AI, SaaS, sales leadership, customer retention, and human connection now have to work together. If you sell, lead sellers, build software, or are trying to understand where SaaS goes next, this episode is worth your time.
1 Jun

Your Winning Edge with Jon Pace

- Growing a Multi-Generational Insurance Business with AI and Relationship Focus In this episode, Skip Balch interviews Jon Pace, Chief Growth Officer at Choice Financial Group, about managing a diverse, multi-generational agency network in the insurance industry. They explore how technology, AI, and relationship-building strategies drive growth and operational efficiency in a complex, regulated environment. Main Topics Covered: - The evolution of Choice Financial Group as a 43-agency roll-up with five generations - The importance of relationship-building and emotional intelligence across generations - How AI is being explored for risk assessment, policy checking, and revenue management while maintaining data security - Strategies for managing growth in a highly cyclical, commoditized market - The role of long-term thinking, mentorship, and cultivating a regenerative, collaborative culture

5 Episodes

One

Creator

Skip Balch, The SalesHandicapper
Years Active

2026
Episodes

5
Rating

Clean
Copyright

© 2026 Skip Balch, The SalesHandicapper