Human-centered selling requires more than just closing deals — it means understanding people, showing empathy, and leading with purpose. In this episode, Doug Weaver (https://www.linkedin.com/in/doug-weaver/), Founder and CEO at Upstream Group (https://upstreamgroup.com/), joins me to share the timeless lessons he’s learned from decades of teaching and practicing sales. From a creative career-defining win at Allure Magazine to decades of training top sellers in digital media, connected TV, online audio and ad-tech space, Doug argues for a return to authentic, process-driven selling rooted in curiosity and courage. Doug and Michael talk about the threat and promise of AI in sales, why the best sellers are “a little bit unreasonable,” and the importance of closing the gap between sales behavior and real human behavior. Join us as we discuss: [3:58] Pivoting from overcoming objections to making the human connection [9:09] Why the sales game has been losing the human touch and the AI conversation [22:06] Not just taking “yes” for an answer and the current state of sales skills Check out these resources we mentioned during the podcast: The Challenger Sale: Taking Control of the Customer Conversation (https://www.amazon.com/Challenger-Sale-Control-Customer-Conversation/dp/1591844355) by Matthew Dixon and Brent Adamson For more My Sales Day, subscribe to the inspiring My Sales Day newsletter at mysalesday.io (http://mysalesday.io), follow the show on Apple Podcasts (https://podcasts.apple.com/us/podcast/my-sales-day/id1762721602), Spotify (https://open.spotify.com/show/6zPdbIpzZLeNOtqoYkTFCJ), or search for “My Sales Day” in your favorite podcast player. Hosted by Ausha. See ausha.co/privacy-policy for more information.

Sales career growth takes more than just hitting quota. In this episode, Joe Didato — a sales veteran with over 25 years of experience in media, ad tech, and SaaS — breaks down what it really takes to advance and stay relevant. From relationship-driven selling to winning big accounts through custom value alignment, Joe shares practical wisdom that’s helped him thrive across industries. He also reflects on lessons learned the hard way, including a tough interview miss that reshaped his mindset forever. Join us as we discuss: [2:12] Selling urgency without being heavy-handed [9:04] Correcting negative behavior in sales career development [17:35] Why people won’t just put the time in for preparation [20:27] Transitioning from traditional sales to SaaS and essential skills Check out these resources we mentioned during the podcast: RepVue (https://www.repvue.com/) For more My Sales Day, subscribe to the inspiring My Sales Day newsletter at mysalesday.io (http://mysalesday.io), follow the show on Apple Podcasts (https://podcasts.apple.com/us/podcast/my-sales-day/id1762721602), Spotify (https://open.spotify.com/show/6zPdbIpzZLeNOtqoYkTFCJ), or search for “My Sales Day” in your favorite podcast player. Hosted by Ausha. See ausha.co/privacy-policy for more information.

Strategic sales relationships take time — and Erin Frey (https://www.linkedin.com/in/freyerin/) knows the payoff. As Senior Account Executive at Nexxen (https://nexxen.com/), Erin shares how she transitioned from the buy side to becoming a trusted, long-term partner to clients.  In this episode, Erin dives into the power of empathy and relationship-building in a fast-moving and unpredictable sales world. We discuss how to balance transactional and strategic selling, why courage matters more than confidence, and the daily grind of building structure in an unstructured sales day. Join us as we discuss: [2:13] Why sellers shouldn’t be afraid to dig deeper into their client relationships [7:57] The biggest mindset shift after jumping into sales from the buyer’s side [12:11] Confronting and correcting passive sales behavior [18:07] How to get your virtual sales call participants to turn on the camera For more My Sales Day, subscribe to the inspiring My Sales Day newsletter at mysalesday.io (http://mysalesday.io), follow the show on Apple Podcasts (https://podcasts.apple.com/us/podcast/my-sales-day/id1762721602), Spotify (https://open.spotify.com/show/6zPdbIpzZLeNOtqoYkTFCJ), or search for “My Sales Day” in your favorite podcast player. Hosted by Ausha. See ausha.co/privacy-policy for more information.

Sales is more than just closing deals — it’s about discipline, evolution, and knowing when to adapt.   Nik Kontoulas (https://www.linkedin.com/in/nikkontoulas/?originalSubdomain=au), Managing Director ANZ at Seedtag and CEO and Founder of JustEggs (https://justeggs.digital/), joins me to share his journey from an ambitious young seller to launching and selling a business — twice. Nik unpacks the evolution of the sales pitch, explaining why the best sellers are those who anticipate market changes before anyone else. He also discusses the power of discipline, why being the first in the office still matters, and how to win deals without relying on a pitch deck. If you're a seller looking for an edge, Nik’s battle-tested insights will give you the confidence and strategy to take your career to the next level. Join us as we discuss: [4:04] The evolution of the sales pitch process as an entrepreneur [12:53] Why you shouldn’t be afraid to hound leads for their business [21:08] Getting your sales team to buy-in on leveling up their skills For more My Sales Day, subscribe to the inspiring My Sales Day newsletter at mysalesday.io (http://mysalesday.io), follow the show on Apple Podcasts (https://podcasts.apple.com/us/podcast/my-sales-day/id1762721602), Spotify (https://open.spotify.com/show/6zPdbIpzZLeNOtqoYkTFCJ), or search for “My Sales Day” in your favorite podcast player. Hosted by Ausha. See ausha.co/privacy-policy for more information.

What are the ingredients to a great sales pitch? According to Matt Rosenberg, Principal Consultant at First Chair Marketing, they’re storytelling, collaboration, knowing how to find and use sales enablement help. Matt shares insights with me from his experience leading sales solutions teams and working hand-in-hand with sellers as well as consulting for businesses with widely different sales cultures. He discusses why team selling creates better outcomes, how sales enablement teams should (and shouldn’t) frame proposals, and why the best salespeople make the buyer the hero of the story. From practical strategies to get enablement teams on your side to the importance of excitement and confidence in a sales pitch, this conversation is packed with insights every B2B seller needs. Join us as we discuss: [3:32] How to build your sales storytelling round your buyer [9:49] Where sellers often struggle in their storytelling scripts [20:14] Crafting a custom narrative that gets your buyer talking For more My Sales Day, subscribe to the inspiring My Sales Day newsletter at mysalesday.io (http://mysalesday.io), follow the show on Apple Podcasts (https://podcasts.apple.com/us/podcast/my-sales-day/id1762721602), Spotify (https://open.spotify.com/show/6zPdbIpzZLeNOtqoYkTFCJ), or search for “My Sales Day” in your favorite podcast player. Hosted by Ausha. See ausha.co/privacy-policy for more information.

Big sales typically don’t happen overnight — momentum builds in increments. Stuart Prentice (https://www.linkedin.com/in/stuartprentice/), Senior Account Executive at Nexxen (https://nexxen.com/), joins me to break down how resilience in sales isn’t about grinding endlessly but about recognizing and capitalizing on small wins. We discuss the power of incremental selling and keeping deals alive through consistent engagement, adding value before contracts are signed, and strategically re-igniting stalled conversations. If you’ve ever felt stuck in a long sales cycle, this episode will give you a new perspective on how patience, persistence, and well-timed nudges lead to big wins. Join us as we discuss: [2:27] How Stu proved his value over a 3-year deal build-up [11:59] Maintaining momentum in the day-to-day sales grind [16:25] Getting out of a “sales slump” and knowing when to hit pause For more My Sales Day, subscribe to the inspiring My Sales Day newsletter at mysalesday.io (http://mysalesday.io), follow the show on Apple Podcasts (https://podcasts.apple.com/us/podcast/my-sales-day/id1762721602), Spotify (https://open.spotify.com/show/6zPdbIpzZLeNOtqoYkTFCJ), or search for “My Sales Day” in your favorite podcast player. Hosted by Ausha. See ausha.co/privacy-policy for more information.

In this compelling episode, Steve Loguidice (https://www.linkedin.com/in/stephenloguidice/), CEO and founder of Varisa Strategic Advisers (https://varisa.co/), shares hard-earned lessons from his 22 years in the industry. Steve talks about how he turned a long-shot pitch into a groundbreaking deal with MTV during his time at BuzzFeed. By focusing on the client’s needs and aligning with their long-term goals, Steve was able to create a campaign so effective it became the blueprint for future collaborations. We also discuss the importance of asking the right questions, such as “What do you need for your money?” — a blunt perspective that transforms conversations from transactional to strategic.  With practical advice on leveraging data, building trust, and understanding buyer motivations, this episode is packed with actionable insights for professionals aiming to elevate their strategic sales game. Join us as we discuss: [2:50] Beavis and Butthead and the psychology of salesmanship  [13:05] What it means to understand before being understood [20:08] Intentional self-improvement and the value of role-playing [24:57] The importance of tracking your personal sales KPIs For more My Sales Day, subscribe to the inspiring My Sales Day newsletter at mysalesday.io (http://mysalesday.io), follow the show on Apple Podcasts, Spotify, or search for “My Sales Day” in your favorite podcast player. Hosted by Ausha. See ausha.co/privacy-policy for more information.

Stephen Clifford (https://www.linkedin.com/in/stephenaclifford/) (Cliff), Managing Director of East Coast Client Partnerships at Infillion (https://infillion.com/), thinks a lot of sales professionals spend too much time behind a screen — and not enough of it getting in front of their clients. Cliff shares how creative outreach (like a game of pickleball) and empathy-driven approaches can help sellers connect with even the toughest decision-makers. He also discusses the importance of asking tough questions, managing rejection, and balancing healthy paranoia, grace, and humility in a high-stakes career. Tune in for practical advice and powerful anecdotes from a sales veteran who knows how to turn connections into long-term partnerships. Join us as we discuss: [4:00] Building a long-term relationship by getting whipped in pickleball  [14:37] How being too nice can backfire in sales meetings [19:24] Approaching sales relationships with a pizza delivery mindset [26:40] Why Cliff does hard activities to make sales feel easier Check out these resources we mentioned during the podcast: Forgotten Wisdom Books (https://www.amazon.com/stores/Stephen-Clifford/author/B0C9KGG7HT?ref=ap_rdr&isDramIntegrated=true&shoppingPortalEnabled=true) For more My Sales Day, subscribe to the inspiring My Sales Day newsletter at mysalesday.io (http://mysalesday.io), follow the show on Apple Podcasts, Spotify, or search for “My Sales Day” in your favorite podcast player. Hosted by Ausha. See ausha.co/privacy-policy for more information.

Resilience defines every great salesperson, and Nena Slifer (https://www.linkedin.com/in/nenaslifer/), Vice President of Healthcare Strategic Partnerships at iHeartMedia (https://www.iheartmedia.com/), has embodied it in every step of her career. From overcoming the challenges of being a young, single mother to mastering enterprise-level sales, Nena’s journey is a testament to grit, thoughtfulness, and strategic vision. She shares how she turned a rejected pitch into a multi-season podcast, the delicate balancing act of managing relationships between clients and agencies, and her proven strategies for combating sales burnout while staying motivated.  Nena’s story offers invaluable lessons and inspiration for surviving and thriving in the face of today’s turbulent sales headwinds. Join us as we discuss: [4:06] Establishing a sales career as a young, single mother [7:35] The delicate dance between pleasing clients and your boss [15:40] Making the most of your time during the sales doldrums [28:01] Pushing through on the account when a buyer doesn’t like you For more My Sales Day, subscribe to the inspiring My Sales Day newsletter at mysalesday.io (http://mysalesday.io), follow the show on Apple Podcasts, Spotify, or search for “My Sales Day” in your favorite podcast player. Hosted by Ausha. See ausha.co/privacy-policy for more information.

Ownership isn’t just a leadership buzzword — for Lindsey Dobbs (https://www.linkedin.com/in/lindsey-dobbs-a9579a14/), it’s her secret sauce for sales success.  The Senior Director of Sales at Nexxen (https://nexxen.com/) joins me to share how embracing ownership at every step, from preparation to delivery, has defined her career. Whether she’s building strategic partnerships or probing for insights, Lindsey’s approach exemplifies how taking charge can differentiate a sales professional in a crowded field.  This episode dives into Lindsey’s top three skills for daily success, how preparation amplifies results, and why you should go into every sales deal with an ownership mindset. Join us as we discuss: [1:26] How taking ownership of your work can lead to big opportunities [11:57] Sales traits versus skills and leaning on your core motivations [21:55] Key advice for sellers who might not be naturally curious Check out these resources we mentioned during the podcast: The Road Back to You (https://www.amazon.com/Road-Back-You-Enneagram-Self-Discovery/dp/0830846190) by Ian Morgan Cron and Suzanne Stabile For more My Sales Day, subscribe to the inspiring My Sales Day newsletter at mysalesday.io (http://mysalesday.io), follow the show on Apple Podcasts, Spotify, or search for “My Sales Day” in your favorite podcast player. Hosted by Ausha. See ausha.co/privacy-policy for more information.