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Wynnett
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Join the Wynnett hosts as they sit down with the sharpest minds in SaaS and tech. This is not your average business chat—this is a deep dive into the repeatable systems, strategic decisions, and processes that turn startups into scaling powerhouses.

  1. What the Marine Corps Taught Me About Success In The Automotive Business

    JAN 5

    What the Marine Corps Taught Me About Success In The Automotive Business

    Dion Davenport, an enterprise account executive at Tire Tutor (https://www.tiretutor.ai), shares his journey in the automotive SaaS industry, discussing the benefits of specializing in a specific vertical. He reflects on his experiences transitioning from sales to leadership, the challenges of selling comprehensive platforms to non-technical buyers, and the importance of understanding client qualifications. Dion also highlights the resistance to technology in the automotive sector and draws parallels between his military background and his sales approach.

    23 min
  2. Lendware VP of Sales on Selling Vertical SaaS Into a Regulated Industry

    12/27/2025

    Lendware VP of Sales on Selling Vertical SaaS Into a Regulated Industry

    Joe Sclafani is VP of Sales at Lendware https://www.lendware.ai - a mortgage CRM platform that combines marketing automation, AI tools, and APIs for mortgage businesses and enterprises. Today we're talking about what breaks when you sell vertical SaaS into a regulated industry; how to build a sales process when your buyers range from individual mortgage shops to enterprises; and how to balance hiring for domain expertise versus sales skills when the product requires both.

    13 min
  3. The Productivity Problem Nobody's Talking About | James Hornblower

    12/23/2025

    The Productivity Problem Nobody's Talking About | James Hornblower

    In this conversation, James Hornblower, Vice President of Business Development at Red Hunt Labs (https://redhuntlabs.com/), discusses the challenges and strategies involved in selling continuous threat exposure management solutions to enterprise security teams. He emphasizes the importance of building trust, understanding client requirements, and structuring deals that provide long-term value. Hornblower also highlights the need for face-to-face interactions in a crowded marketplace and shares insights on navigating long sales cycles and differentiating in a competitive environment.

    23 min
  4. Building and Scaling Require Completely Different Brains

    12/22/2025

    Building and Scaling Require Completely Different Brains

    Dan San, CEO of Sitekick AI (https://sitekick.ai/), shares his experience in entrepreneurship, detailing the differences between scaling a business for others and building his own startup. This discussion highlights the unique skillsets required for startup success factors and how they contrast with leadership roles in larger companies. Our conversation also touches on saas marketing strategies.

    16 min
  5. Pre-Sales: The B2B Game Changer Most OVERLOOK

    12/21/2025

    Pre-Sales: The B2B Game Changer Most OVERLOOK

    In the ever-evolving landscape of B2B sales, pre-sales roles are often overshadowed by their sales counterparts. However, as Lorraine Abrego, a pre-sales specialist at Propensity (https://www.propensity.com) highlights, the pre-sales function is crucial for addressing buyer needs and ensuring a smooth transition from interest to decision. Lorraine’s examines the vital role pre-sales plays in account-based marketing (ABM) and how it shapes the overall sales process.

    13 min
  6. What Martial Arts Has Taught Me About Sales

    12/21/2025

    What Martial Arts Has Taught Me About Sales

    Our guest today is Stefan Lugo. He is a Business Development Representative at Bearworks https://bearworks.com - an AI-powered sales platform that helps B2B teams with parallel dialing, virtual sales floors, and coaching tools integrated into Salesforce and HubSpot. Stefan is also a BJJ brown belt and former Registered Behavioral Technician working with children on the spectrum. Today we're talking about what you learn when you compress multiple BDR roles into a short timeframe - the pattern recognition that comes from seeing different outbound motions, the meta-dynamics of selling to sales teams as a practitioner, and how skills from martial arts and behavioral therapy translate into reading prospects and handling objections.

    19 min
  7. Enterprise Sales Isn't About Price - It's About This

    12/18/2025

    Enterprise Sales Isn't About Price - It's About This

    In the dynamic world of sales, understanding the intricacies of customer interactions and internal processes can be the key to success. Mian Habib, Sales Director at Siemens Digital Industries Software, shares his journey through various roles in sales, marketing, and customer success, shedding light on how these experiences shape effective sales strategies. This episode explores the valuable lessons learned from his diverse career and how they can be applied to build a successful sales system.

    30 min
  8. The Sales Approach That Replaces KPI Obsession

    12/16/2025

    The Sales Approach That Replaces KPI Obsession

    Miguel Guerrero, Global Head of Business Development at Orbital, offers insights into effective sales management, highlighting the importance of a people-first approach beyond just focusing on KPIs. In the rapidly evolving landscape of technology, the transition from selling visually engaging AI products to revolutionizing traditional industries presents unique challenges and opportunities. In this insightful podcast episode Miguel shares his experiences in navigating the complexities of business development in the property tech sector.

    19 min
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Join the Wynnett hosts as they sit down with the sharpest minds in SaaS and tech. This is not your average business chat—this is a deep dive into the repeatable systems, strategic decisions, and processes that turn startups into scaling powerhouses.

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