MySalesDay

Michael Hess
  • 5.0 (1)
  • BUSINESS
  • UPDATED WEEKLY

Sales is hard...brutally hard.   And it's messy.   My Sales Day is a podcast BY Sellers, FOR Sellers. I’m Michael Hess, Founder and Chief Seller Advocate of “My Sales Day”, and it's my job to make “the sales life” "less messy" for you...and of course,  to help you excel and perform at your peak abilities.  My goal is to make your time here educational, inspirational, and actionable.  And yeah, entertaining too…sales doesn’t have to be boring!  Selling is fun too, so let’s have some of that here as well. You'll get skill ideas, action items, and hugs.   Yes, hugs.   You need support and you don't often get it from inside your org, and you certainly don't get it from the street.   The goal of this show is that you walk away with ideas, confidence, and a whole lot of skip in your step.   And if you need more of this positivity in your sales day, be sure to read  the MySalesDay email which you can get by subscribing at  mysalesday.io (http://mysalesday.io). Hosted on Ausha. See ausha.co/privacy-policy for more information.

  1. 08/19/2025

    Complex Sales: Why Nuance Is the Spice of SaaS

    In this episode, Grant le Riche, VP of Client Strategy at Eighty Twenty joins me to dive into the mindset required to master the complex sales process. Grant shares how his career evolved from highly transactional sales to a more strategic, consultative approach. We talk about the importance of preparing for every interaction, even when you think it's just a formality, and how he recovered a deal after his boss "junked up" a meeting. Grant also reveals his secrets to building authentic champions and why self-appraisal is a critical skill for any professional seller. Join us as we discuss: [2:29] Working with siloed departments and the nuances of complex SaaS sales  [13:45] Why every informal meeting isn’t and champion development [24:23] If AI is the canary in the coal mine for critical thinking in sales [37:02] Proactively addressing and shrinking your buyer’s objections For more My Sales Day, subscribe to the inspiring My Sales Day newsletter at mysalesday.io, follow the show on Apple Podcasts, Spotify, or search for “My Sales Day” in your favorite podcast player. Hosted on Ausha. See ausha.co/privacy-policy for more information.

    43 min

  2. 07/22/2025

    Qualifying Your Buyers: Sharpen Your Invisible Sword to Win More Sales

    Qualifying clients is the invisible sword every seller must wield, but too few do so effectively. Penry Price, Founding and Managing Partner at Charcoal Advisors, joins me to explore why qualifying is foundational to successful selling, despite often being underutilized. Penry leans on his experiences at Google, LinkedIn, and other major media entities to highlight how a disciplined approach to qualifying protects precious selling time, uncovers genuine client needs, and ensures that efforts align with opportunities most likely to close. Listen to learn how properly qualifying clients can transform your pipeline, sharpen your strategic focus, and dramatically improve your sales outcomes. Join us as we discuss: [1:40] Managing external factors through preparation and persistence [15:51] Navigating big expectations and why a little paranoia is a good thing [21:19] How qualifying your clients is your ultimate timesaver [25:03] Flipping the sense of urgency on its head and the art of brand storytelling For more My Sales Day, subscribe to the inspiring My Sales Day newsletter at mysalesday.io, follow the show on Apple Podcasts, Spotify, or search for “My Sales Day” in your favorite podcast player. Hosted on Ausha. See ausha.co/privacy-policy for more information.

    51 min

  3. 07/08/2025

    Don't Just Pitch: A Masterclass in Point of View Selling

    Charlie Thomas, Founder of Charlie Thomas Coaching & Consulting, doesn’t focus on pitching harder. Instead, he leans on point of view selling to think bigger. Charlie joins me to share how bold ideas and strategic alignment can transform not just deals, but careers. He recounts the day he closed a multimillion-dollar partnership with Dr. Pepper Snapple by inventing a value-driven offsite on the fly, and how that single act helped multiple clients climb to CMO. From there, he breaks down the mechanics of POV selling, the role of strategic discovery, and why cultivating alignment is key to speed, health, and trust in every sales relationship. Join us as we discuss: [2:29] How an authentic point of view creates action and builds trust [17:33] Why speed and health make up the golden rule of performance — alignment [25:40] The importance of strategic initiatives and a sense of urgency For more My Sales Day, subscribe to the inspiring My Sales Day newsletter at mysalesday.io, follow the show on Apple Podcasts, Spotify, or search for “My Sales Day” in your favorite podcast player. Hosted on Ausha. See ausha.co/privacy-policy for more information.

    38 min

  4. 06/24/2025

    Inside the Recruiter’s Mind: Landing Sales Roles That Fit

    Recruiting isn’t just about filling positions but changing lives. Mike Giunta, Managing Director at TalentClimb, joins me to talk about the deeper human side of recruiting, sharing stories of how his careful, ethical approach has built lasting trust and stronger client relationships. From his decision to lose a lucrative placement because of a recruit’s falsified credentials to understanding candidate motivations beyond just career moves, Mike demonstrates why empathy, storytelling, and transparency are essential in recruiting. Listen in to learn how his thoughtful approach to recruiting can positively impact your professional sales reputation and win trust with your long-term clients. Join us as we discuss: [4:24] Why transparency is better for long-term ROI over a questionable quick win [9:34] Emotional transactions in recruiting and the “run to” or “run from” conundrum  [20:17] The juggling act of bragging about yourself versus presenting real value For more My Sales Day, subscribe to the inspiring My Sales Day newsletter at mysalesday.io, follow the show on Apple Podcasts, Spotify, or search for “My Sales Day” in your favorite podcast player. Hosted on Ausha. See ausha.co/privacy-policy for more information.

    35 min

  5. 06/03/2025

    Sales Sabotage: Emotionally Resetting After a Busted Deal

    To Daryl Faulkner, Account Director at Heritage Werks, “patient tenacity” isn’t just a phrase — it’s a proven strategy. In this episode, Daryl breaks down how he closed a surprising incremental deal with a legacy client known for not having budget. He also shares how attentive listening, long-term relationship building, and asking the right questions set him up to capitalize when a new budget opportunity appeared. We also discuss why rapport matters more than the pitch, how he’s developed presentation skills into a true superpower, and the surprising sales lessons he learned as a paperboy. Join us as we discuss: [2:10] Playing the waiting game with a client who has no budget spend [15:30] Reframing busted deals into potential opportunities [25:41] When someone sabotages your meeting and firing clients  For more My Sales Day, subscribe to the inspiring My Sales Day newsletter at mysalesday.io, follow the show on Apple Podcasts, Spotify, or search for “My Sales Day” in your favorite podcast player. Hosted on Ausha. See ausha.co/privacy-policy for more information.

    36 min

  6. 05/20/2025

    Human-Centered Selling: Process, Empathy, and a Little Bit of Unreasonable

    Human-centered selling requires more than just closing deals — it means understanding people, showing empathy, and leading with purpose. In this episode, Doug Weaver, Founder and CEO at Upstream Group, 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 by Matthew Dixon and Brent Adamson For more My Sales Day, subscribe to the inspiring My Sales Day newsletter at mysalesday.io, follow the show on Apple Podcasts, Spotify, or search for “My Sales Day” in your favorite podcast player. Hosted on Ausha. See ausha.co/privacy-policy for more information.

    48 min

  7. 05/06/2025

    Why Sales Career Growth Starts with Raising Your Hand

    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 For more My Sales Day, subscribe to the inspiring My Sales Day newsletter at mysalesday.io, follow the show on Apple Podcasts, Spotify, or search for “My Sales Day” in your favorite podcast player. Hosted on Ausha. See ausha.co/privacy-policy for more information.

    34 min

  8. 04/22/2025

    Be Assertive: The Hardest Learned Skill in Sales Relationships

    Strategic sales relationships take time — and Erin Frey knows the payoff. As Senior Account Executive at Nexxen, 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, follow the show on Apple Podcasts, Spotify, or search for “My Sales Day” in your favorite podcast player. Hosted on Ausha. See ausha.co/privacy-policy for more information.

    34 min
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Trailer

About

Sales is hard...brutally hard.   And it's messy.   My Sales Day is a podcast BY Sellers, FOR Sellers. I’m Michael Hess, Founder and Chief Seller Advocate of “My Sales Day”, and it's my job to make “the sales life” "less messy" for you...and of course,  to help you excel and perform at your peak abilities.  My goal is to make your time here educational, inspirational, and actionable.  And yeah, entertaining too…sales doesn’t have to be boring!  Selling is fun too, so let’s have some of that here as well. You'll get skill ideas, action items, and hugs.   Yes, hugs.   You need support and you don't often get it from inside your org, and you certainly don't get it from the street.   The goal of this show is that you walk away with ideas, confidence, and a whole lot of skip in your step.   And if you need more of this positivity in your sales day, be sure to read  the MySalesDay email which you can get by subscribing at  mysalesday.io (http://mysalesday.io). Hosted on Ausha. See ausha.co/privacy-policy for more information.

Information

  • Creator
    Michael Hess
  • Years Active
    2024 - 2025
  • Episodes
    29
  • Rating
    Clean
  • Copyright
    © Michael Hess
  • Show Website
    MySalesDay