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Salesology® - Conversations with Sales Leaders

Salesology® - Conversations with Sales Leaders

By: Wendy Weiss
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 When you are ready to transform your sales for today’s transforming market, this is the show for you. In the Salesology®️ podcast, you’re going to be getting the real scoop, the inside story from sales leaders who will deliver the goods on how to grow sales faster, more easily and more profitably. With your host, The Queen of Cold Calling®️ and Founder of Salesology®️, award winning author, speaker, sales trainer and coach, Wendy Weiss.2023 Economics Marketing Marketing & Sales Personal Development Personal Success
Episodes
  • 146: Ben Filkouski – Finding Your ‘Why’

    146: Ben Filkouski – Finding Your ‘Why’
    Jul 14 2025
    Guest: Ben Filkouski Guest Bio: ​Ben graduated from the University of Wisconsin – Madison in 2018. Upon graduating, Ben worked for Goldleaf Development, a Multi-Family Developer in Dane County, where he obtained his Real Estate License. In September of 2019, Ben joined Madison Commercial Real Estate. Since joining Madison Commercial Real Estate, Ben has become a Partner with the firm, obtained his Real Estate Brokers License, and earned his CCIM (Certified Commercial Investment Member) designation. Ben currently serves on the board of Commercial Brokers Group Inc. (CBG) a CRE Organization based out of Madison, WI. CBG recognizes top deals completed annually, and Ben has won Land Deal of the Year in 2021 & Overall Deal of the Year in 2021, Industrial Deal of the Year in 2022, and Land Deal of the Year in 2024. Ben is also an active member in the Commercial Association of Realtors Wisconsin (CARW) where he was formerly on the NextGen Committee and was runner-up for Industrial Deal of the Year for the State of Wisconsin in 2022. Ben is also an active member with Smart Growth Greater Madison, a real estate development lobbying & networking organization. Key Points: Entry into Real Estate: Ben initially resisted going into real estate despite a family background in it. He became interested after experiencing different aspects like construction, deal-making, and sales. Ben fell in love with real estate during a brokerage role, especially the dynamic nature of the work and helping clients grow. Unexpected Career Path: Ben originally considered a career in the arts due to a love of creative thinking and writing. He found that creativity and communication are actually essential to being successful in real estate sales. Natural Networker: Networking comes naturally due to a talkative personality and curiosity about people. Ben enjoys building relationships, whether or not they lead to direct business. He learned the value of strategic networking, focusing on a few meaningful conversations rather than quantity. He uses networking as a way to stay top of mind for real estate opportunities. Team Growth & Hiring Philosophy: Ben recently grew the team by hiring two new associates. Hiring isn’t based solely on experience, personality, drive, and communication skills are more important. Ben looks for self-motivation, competitiveness, and professionalism. He emphasizes the long timeline before new brokers become profitable, so cultural and personal fit is essential. Screening New Hires: Ben created a detailed training portal designed to take 50–60 hours. He doesn’t tell new hires how long it should take—completion speed reveals attention to detail and commitment. He uses early performance during training as a key indicator of long-term potential. Managing Associates: One challenge is frequent interruptions that break focus. Ben implements short, scheduled check-ins (10–15 minutes) instead of ad hoc questions. This structure improves efficiency for both managers and associates. Ben believes some level of independence should be expected after the initial learning phase. Culture and Success Metrics: Culture encourages brokers to “live the lifestyle”—be self-driven, schedule smartly, and network. The firm has seen improved success rates and retention since implementing more structured onboarding and evaluation systems. Guest Links: Connect on LinkedIn Connect on Instagram https://madisoncommercialre About Salesology®: Conversations with Sales Leaders Download your free gift, The Salesology® Vault. The vault is packed full of free gifts from sales leaders, sales experts, marketing gurus, and revenue generation experts. Download your free gift, 81 Tools to Grow Your Sales & Your Business Faster, More Easily & More Profitably. Save hours of work tracking down the right prospecting and sales resources and/or digital tools that every business owner and salesperson needs. If you are a business owner or sales manager with an underperforming sales team, let’s talk. Click here to schedule a time. Please subscribe to Salesology®: Conversations with Sales Leaders so that you don't miss a single episode, and while you're at it, won't you take a moment to write a short review and rate our show? It would be greatly appreciated! To learn more about our previous guests, listen to past episodes, and get to know your host, go to https://podcast.gosalesology.com/ and connect on LinkedIn and follow us on Facebook and Instagram, and check out our website at https://gosalesology.com/.
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    24 mins
  • 145: Matthew Freed – Simplifying the Complicated

    145: Matthew Freed – Simplifying the Complicated
    Jul 7 2025
    Guest: Matthew Freed Guest Bio: ​I’ve spent the last 20 years in sales and sales leadership, and I still find it incredibly rewarding. Most of that time has been in manufacturing and distribution, where I’ve had the opportunity to lead high-performing teams and work closely with customers. I currently lead a team across the Midwest and am passionate about building lasting culture, driving results, and simplifying the complicated. A big part of my leadership style is helping sellers achieve their goals while supporting them in becoming the best versions of themselves. I believe consistent habits lead to consistent outcomes, and I aim to lead with energy, clarity, and accountability. I enjoy helping people grow in their careers while building meaningful, long-term relationships with customers and colleagues. Outside of work, I still love to compete—whether it’s on the basketball court or just a backyard game with friends. Most importantly, I enjoy time with my wife and our two daughters. Key Points: Career Journey & Sales Background His dad was in sales and eventually owned a business, which influenced him early. Matthew started with cold calling and door-to-door efforts, learning what real sales was versus the perception. Naturally gravitated toward leadership roles on teams; wanted to shift from individual sales to team success. Moved cities and took a risk to lead a sales team at a manufacturing company, eventually growing in responsibility and geography. He was introduced to Millcraft by a supplier contact and joined over 8 years ago; currently leads sales efforts after transitioning from operational responsibilities. Sales Philosophy & Simplifying Complexity Believes the sales team is his "customers" and supports them by removing obstacles and improving processes. Matthew uses what he calls a "Simplify the Complicated" Approach: · Sales fundamentals (know, like, trust) are still the core, despite evolving technology. · Use data and analytics to validate feelings and drive decisions. · Focus on what matters: simplify systems/processes to let sellers focus on selling. Challenges in Sales Leadership Reps often react emotionally, inventing stories about prospects. Ask clarifying questions, do a fact-finding mission, and use both data and instinct (e.g., the "sleep on it" approach). Helps reps stay grounded by focusing on facts and controllables rather than assumptions. CRM/ERP Adoption Success Successfully implemented a new ERP system that includes a CRM. Tailored the system to serve salespeople and their customers. Positioned CRM is used as a way to better serve customers and make smarter decisions. Gained buy-in by connecting usage to outcomes (e.g., customer satisfaction). Has most of his team (12 people) consistently using the CRM. Team Composition & Hiring A mix of new and long-tenured reps (some with 30–40+ years of experience). Has a team size of 12 sellers. What He Looks for in Hires is resourcefulness, values competitiveness, entrepreneurial spirit, and inquisitiveness. Matthew’s screening methods are assignments before interviews, looking for how much effort candidates put into research, a sports background is a strong signal (discipline, competition), and relying heavily on referrals. Team Wins & New Business Growth - 150+ New Accounts Opened Focused efforts in specific industry segments (e.g., beverage, signage, apparel, nonprofits). Leverages repeatable success models: if one nonprofit buys certain items, others likely will too. Emphasizes selling similar things to similar customers vs. reinventing every sale. Segment-focused selling allows for scalable, repeatable growth strategies. Leadership Style & Values Clearly outlines what reps should expect from him and vice versa. Believes in accountability, honesty, and mutual respect. Sees his role as equipping and clearing the path for his team’s success. Encourages feedback and builds relationships rooted in trust. Guest Links: Connect on LinkedIn About Salesology®: Conversations with Sales Leaders Download your free gift, The Salesology® Vault. The vault is packed full of free gifts from sales leaders, sales experts, marketing gurus, and revenue generation experts. Download your free gift, 81 Tools to Grow Your Sales & Your Business Faster, More Easily & More Profitably. Save hours of work tracking down the right prospecting and sales resources and/or digital tools that every business owner and salesperson needs. If you are a business owner or sales manager with an underperforming sales team, let’s talk. Click here to schedule a time. Please subscribe to Salesology®: Conversations with Sales Leaders so that you don't miss a single episode, and while you're at it, won't you take a moment to write a short review and rate our show? It would be greatly appreciated! To learn more about our previous guests, listen to past episodes, and get to know your host, go to https://...
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    29 mins
  • 144: Nick Sowards – Never Give Up

    144: Nick Sowards – Never Give Up
    Jun 30 2025
    Guest: Nick Sowards Guest Bio: ​Started cleaning machines in California at 18 years old at my grandfather’s company. Graduated into selling machines at 19, then left his company at 20 to sell new machines. Left California in 2004 and joined Absolute Machine Tools, selling their imported brands. In 2015, became GM for Absolute, running their Chicago facility. 2017 needed a change in my life and left Absolute with joining Ellison Technologies in December 17, and the ride has been great thus far! I'm a sales manager for NE Ohio and a territory manager for Lake and 1/2 of Cuyahoga County. I was honored to have been the #1 salesman in Ellison for GP and units for 2023, with also getting salesperson of the year awards. Been in the top 5-10 ever since I started with Ellison in 2017. We have a great team in Ohio, so that helps! Key Points: Early Influences and Entry into Sales · Grandfather's machine shop played a formative role. He started by cleaning machines as a kid to earn money for things his family couldn't afford. · Originally planned to become an FBI agent, but his mother recognized his strong communication skills and encouraged sales. · A pivotal moment came when he accidentally made a $10,000 sale, earned $200 commission, and realized sales were more rewarding than cleaning machines. Motivation and Personal Drive · Grew up poor, became a young father, and was driven by the desire to support his family, including allowing his wife to stay home. · Has seven daughters, now expecting three grandchildren, further reinforcing his motivation to succeed financially and professionally. Leadership and Management Style · Leads a tight-knit sales team of three, focusing on trust, open communication, and family-like support. Believes success is shared: if his team does well, he does well. · Encourages open access; his team can call him anytime, for work or personal matters. Hiring Philosophy · Looks for motivation (expensive hobbies, family responsibilities) and coachability. · Avoids hiring “negative” people; prioritizes positive, adaptable personalities. · Uses personality assessments and informal settings (like lunch) to gauge candidates more authentically. Watches for signs of intrinsic drive, not just skill. Building Trust with New Hires · Leads by example: gave a full commission on a deal made the day before a new rep joined, demonstrating generosity and fairness. · Builds trust through action, not just words, follows through, supports his team, and solves problems directly or connects them with the right resources. Sales Philosophy · Be honest and transparent: admit when you don’t know something, but always get the correct answers. · Never be a “yes man”, integrity builds long-term relationships. · Success is based on persistence, teamwork, and customer focus. Guest Links: Cell: 216-347-9566 Email: nsowards@ellisontechnologies.com Connect on LinkedIn About Salesology®: Conversations with Sales Leaders Download your free gift, The Salesology® Vault. The vault is packed full of free gifts from sales leaders, sales experts, marketing gurus, and revenue generation experts. Download your free gift, 81 Tools to Grow Your Sales & Your Business Faster, More Easily & More Profitably. Save hours of work tracking down the right prospecting and sales resources and/or digital tools that every business owner and salesperson needs. If you are a business owner or sales manager with an underperforming sales team, let’s talk. Click here to schedule a time. Please subscribe to Salesology®: Conversations with Sales Leaders so that you don't miss a single episode, and while you're at it, won't you take a moment to write a short review and rate our show? It would be greatly appreciated! To learn more about our previous guests, listen to past episodes, and get to know your host, go to https://podcast.gosalesology.com/ and connect on LinkedIn and follow us on Facebook and Instagram, and check out our website at https://gosalesology.com/.
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    34 mins

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