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SellMeThisPen podcast
By SellMeThisPenEducation
SellMeThisPen podcast episodes
- #50 How to Coach Sellers Who Don't Want Help (Proven Tactics) | Edward Cannon on SellMeThisPen Pod
About the episode:
In this episode, Michael and Ed dive into sales enablement and the power of tactical support. They discuss the importance of building individual relationships with sellers, understanding their unique motivations, and providing hands-on help rather than just theoretical training. Ed shares his journey from sales to enablement, emphasizing how empathy, timing, and being genuinely helpful are the keys to successful enablement.
About the guest:
Edward Cannon is a seasoned sales enablement professional with over 3 years of dedicated experience, who transitioned from enterprise sales at Verizon to sales enablement at JLL after proving himself as a top-performing seller and natural coach. Today, he leads sales enablement initiatives covering deal coaching, sales methodologies, and process optimization, applying his hands-on sales experience to make sellers' lives easier.
Where to find Edward Cannon:
LinkedIn: https://www.linkedin.com/in/edward-cannon/
Where to find Michael (Founder & CEO @ SellMeThisPen AI):
Email: [email protected]
LinkedIn https://www.linkedin.com/in/michaelocean/
Try SellMeThisPen AI @ https://www.sellmethispen.ai/
🌟 SellMeThisPen AI is the only all-in-one AI sales coaching platform that helps sellers in every step of their journey.
Before client calls - Role-play realistic sales conversations with AI to perfect your pitch and practice objection handling, without burning precious leads.
During client calls - Receive real-time guidance to handle objections consistently and get reminded to ask the right questions so you can win deals faster.
After client calls - Get unbiased feedback so you can improve next time. And it doesn't stop there—SMTP takes care of your notes and CRM updates so you can focus on selling instead of admin work.
41 min - #49 Data-Driven Sales Leadership: Turning B-Players into Top Performers | Guy Rubin on SellMeThisPen Pod
About the episode:
In this episode, Michael and Guy dive into the latest Ebsta benchmark report on sales performance. They explore why just 14% of sellers are responsible for 80% of revenue, how top performers qualify deals earlier based on ICP, and why data-driven consistency across sales processes is the key to transforming B and C players into quota-crushers.
About the guest:
Guy Rubin is a passionate sales and data leader who founded Ebsta, a revenue intelligence platform with nearly 400 customers that's focused on solving data quality issues in Salesforce and providing relationship intelligence. Last year the company has grown by 68% last year and developed benchmarking tools that help identify what top performers are doing differently, enabling organizations to prompt B and C players with actionable insights that drive consistent sales performance across teams.
Where to find Guy Rubin:
LinkedIn: https://www.linkedin.com/in/rubinguy/
Where to find Michael (Founder & CEO @ SellMeThisPen AI):
Email: [email protected]
LinkedIn https://www.linkedin.com/in/michaelocean/
Try SellMeThisPen AI @ https://www.sellmethispen.ai/
🌟 SellMeThisPen AI is the only all-in-one AI sales coaching platform that helps sellers in every step of their journey.
Before client calls - Role-play realistic sales conversations with AI to perfect your pitch and practice objection handling, without burning precious leads.
During client calls - Receive real-time guidance to handle objections consistently and get reminded to ask the right questions so you can win deals faster.
After client calls - Get unbiased feedback so you can improve next time. And it doesn't stop there—SMTP takes care of your notes and CRM updates so you can focus on selling instead of admin work.
46 min - #48 Leadership Development: From Tactical Manager to Leader | Jenny Floros on SellMeThisPen Pod
About the episode:
In this episode, Michael and Jenny dive into the realities of leadership development for mid-level managers. They discuss why embracing both tactical management and true leadership is crucial for company growth, how good mentors can transform career trajectories, and why intentional time management is the secret weapon for today's overwhelmed managers.
About the guest:
Jenny Floros is a seasoned leadership development expert with over three decades of experience across live entertainment ticketing, tech startups, and an 11-year journey at Groupon where she discovered her passion for developing leaders. After building her foundation in sales and leadership, Jenny launched her own business two and a half years ago focused on leadership development for mid-level management in tech companies, helping managers unlock their potential through coaching and practical frameworks.
Where to find Jenny Floros:
LinkedIn: https://www.linkedin.com/in/jennyfloros/
Where to find Michael (Founder & CEO @ SellMeThisPen AI):
Email: [email protected]
LinkedIn https://www.linkedin.com/in/michaelocean/
Try SellMeThisPen AI @ https://www.sellmethispen.ai/
🌟 SellMeThisPen AI is the only all-in-one AI sales coaching platform that helps sellers in every step of their journey.
Before client calls - Role-play realistic sales conversations with AI to perfect your pitch and practice objection handling, without burning precious leads.
During client calls - Receive real-time guidance to handle objections consistently and get reminded to ask the right questions so you can win deals faster.
After client calls - Get unbiased feedback so you can improve next time. And it doesn't stop there—SMTP takes care of your notes and CRM updates so you can focus on selling instead of admin work.
49 min - #47 AI Implementation That Actually Drives Sales Results | Steve Smith on SellMeThisPen Pod
About the episode:
In this episode, Michael and Stephen dive into the realities of implementing AI in organizations. They discuss how to drive user adoption through leadership involvement, why starting with practical use cases beats broad implementation, and the importance of creating a culture where experimentation with AI tools is encouraged and celebrated.
About the guest:
Stephen Smith is a technology and strategy veteran with over 30 years of experience across tech companies, startups, and consulting firms, having served as CEO, CFO, and SVP of RevOps before transitioning to focus exclusively on AI about three years ago. Now running his practice at NextAccess as a senior partner, Steve helps law firms, private equity firms, and tech companies implement AI across their organizations through custom training programs and workshops that transform daily workflows and drive productivity.
Where to find Steve Smith:
LinkedIn: https://www.linkedin.com/in/smithstephen/
Where to find Michael (Founder & CEO @ SellMeThisPen AI):
Email: [email protected]
LinkedIn https://www.linkedin.com/in/michaelocean/
Try SellMeThisPen AI @ https://www.sellmethispen.ai/
🌟 SellMeThisPen AI is the only all-in-one AI sales coaching platform that helps sellers in every step of their journey.
Before client calls - Role-play realistic sales conversations with AI to perfect your pitch and practice objection handling, without burning precious leads.
During client calls - Receive real-time guidance to handle objections consistently and get reminded to ask the right questions so you can win deals faster.
After client calls - Get unbiased feedback so you can improve next time. And it doesn't stop there—SMTP takes care of your notes and CRM updates so you can focus on selling instead of admin work.
36 min - #46 Sales Coaching Mastery: The Art of Asking the Right Questions | Kieran Smith on SellMeThisPen Pod
About the episode:
In this episode, Michael and Kieran dive into the realities of sales coaching and what it really takes to develop high-performing reps. They discuss why quality questions trump feedback dumps, how true coaching creates psychological safety through self-reflection, and why the fundamentals of curiosity and consistency matter more than chasing silver bullets in today's tough market.
About the guest:
Kieran Smith is a seasoned sales enablement expert with 17+ years in the sales world, starting as a frontline seller and spending over a decade in sales leadership before pivoting to enablement. Currently serving as Senior Director of Enablement at Technology Advice, Kieran brings a coaching-focused approach to helping teams perform better through thoughtful questioning techniques and a belief in mastering the fundamentals that "take no talent.”
Where to find Kieran Smith:
LinkedIn: https://www.linkedin.com/in/kieransmithvp/
Where to find Michael (Founder & CEO @ SellMeThisPen AI):
Email: [email protected]
LinkedIn https://www.linkedin.com/in/michaelocean/
Try SellMeThisPen AI @ https://www.sellmethispen.ai/
🌟 SellMeThisPen AI is the only all-in-one AI sales coaching platform that helps sellers in every step of their journey.
Before client calls - Role-play realistic sales conversations with AI to perfect your pitch and practice objection handling, without burning precious leads.
During client calls - Receive real-time guidance to handle objections consistently and get reminded to ask the right questions so you can win deals faster.
After client calls - Get unbiased feedback so you can improve next time. And it doesn't stop there—SMTP takes care of your notes and CRM updates so you can focus on selling instead of admin work.
46 min - #45 Authentic Leadership: Building Lasting Impact | Teri Long on SellMeThisPen Pod
About the episode:
In this episode, Michael and Teri dive into what makes authentic leaders successful in enablement. They discuss why getting your hands dirty with frontline teams is crucial, how leaders who don't have all the answers build stronger organizations, and why AI will enhance productivity but never replace the human connection at the heart of sales.
About the guest:
Teri Long is the VP of GTM Revenue & Customer Enablement at Mindtickle and an award-winning sales enablement leader, receiving the Selling Power Enablement Excellence Awards in 2023 and 2024. With over 25 years of experience starting as a quota-carrying rep before transitioning to enablement leadership, Teri now serves as a strategic advisor and executive coach while being recognized as an SEC One to Watch for her significant contributions to the enablement field.
Where to find Teri Long:
LinkedIn: https://www.linkedin.com/in/terilong/
Where to find Michael (Founder & CEO @ SellMeThisPen AI):
Email: [email protected]
LinkedIn https://www.linkedin.com/in/michaelocean/
Try SellMeThisPen AI @ https://www.sellmethispen.ai/
🌟 SellMeThisPen AI is the only all-in-one AI sales coaching platform that helps sellers in every step of their journey.
Before client calls - Role-play realistic sales conversations with AI to perfect your pitch and practice objection handling, without burning precious leads.
During client calls - Receive real-time guidance to handle objections consistently and get reminded to ask the right questions so you can win deals faster.
After client calls - Get unbiased feedback so you can improve next time. And it doesn't stop there—SMTP takes care of your notes and CRM updates so you can focus on selling instead of admin work.
35 min - #44 Stop Limiting Enablement to Sales Teams Only | Matt Schalsey on SellMeThisPen Pod
About the episode:
In this episode, Michael and Matt dive into the parallels between recruitment and sales processes. They discuss why recruiters are essentially sales professionals selling company vision, how bad hiring directly impacts enablement efforts, and why improving recruitment processes with better questions and AI assistance can help teams hire for roles instead of just filling seats.
About the guest:
Matt Schalsey is an award-winning Go-To-Market advisor and the CEO & Founder of Perfect Hire, where he's developing an AI-infused Applicant Relationship Manager that combines ATS and CRM functionalities to streamline the hiring process. With extensive experience as a sales enablement leader at companies like ZoomInfo, Chorus.ai, and Chili Piper, Matt is also a co-founder of an Enablement Squad community.
Where to find Matt Schalsey:
LinkedIn: https://www.linkedin.com/in/matt-schalsey/
Where to find Michael (Founder & CEO @ SellMeThisPen AI):
Email: [email protected]
LinkedIn https://www.linkedin.com/in/michaelocean/
Try SellMeThisPen AI @ https://www.sellmethispen.ai/
🌟 SellMeThisPen AI is the only all-in-one AI sales coaching platform that helps sellers in every step of their journey.
Before client calls - Role-play realistic sales conversations with AI to perfect your pitch and practice objection handling, without burning precious leads.
During client calls - Receive real-time guidance to handle objections consistently and get reminded to ask the right questions so you can win deals faster.
After client calls - Get unbiased feedback so you can improve next time. And it doesn't stop there—SMTP takes care of your notes and CRM updates so you can focus on selling instead of admin work.
43 min - #43 Why Change Management Is A Critical Skill in Sales Enablement | Crystal Nikosey on SellMeThisPen Pod
About the episode:
In this episode, Michael and Crystal dive into the realities of change management in sales enablement. They discuss why understanding company culture is critical before implementing new frameworks, how to get leadership buy-in across all levels, and why competency-led frameworks are essential for measuring behavior change and creating effective coaching cultures.
About the guest:
Crystal Nikosey is a dedicated enablement professional with over eight years of experience who transitioned from carrying a bag as a seller to becoming @Your_Favorite_Enabler across various social platforms. With a competitive spirit and holistic approach to enablement, Crystal is passionate about where the field is heading, particularly around change management and AI transformation, and remains active in the Sales Enablement Collective community.
Where to find Crystal Nikosey:
LinkedIn: https://www.linkedin.com/in/crystalnikosey/
Where to find Michael (Founder & CEO @ SellMeThisPen AI):
Email: [email protected]
LinkedIn https://www.linkedin.com/in/michaelocean/
Try SellMeThisPen AI @ https://www.sellmethispen.ai/
🌟 SellMeThisPen AI is the only all-in-one AI sales coaching platform that helps sellers in every step of their journey.
Before client calls - Role-play realistic sales conversations with AI to perfect your pitch and practice objection handling, without burning precious leads.
During client calls - Receive real-time guidance to handle objections consistently and get reminded to ask the right questions so you can win deals faster.
After client calls - Get unbiased feedback so you can improve next time. And it doesn't stop there—SMTP takes care of your notes and CRM updates so you can focus on selling instead of admin work.
42 min - #42 70% of Buyers Avoid Salespeople - How To Be In The 30% | Steve Reid on SellMeThisPen Pod
About the episode:
In this episode, Michael and Steve dive into the real world of sales transformation and leadership. They discuss why modern buyers have fundamentally changed their expectations, how traditional product-focused selling is failing, and why the most successful salespeople approach selling as problem-solving rather than feature-dumping to create authentic value for customers.
About the guest:
Steve Reid is a seasoned sales leader with over 30 years of experience who transitioned from marketing to sales leadership, eventually scaling a company to $50 million before a successful exit. Currently, as the founder of Venatas, he works with eight different venture-backed companies as a fractional CRO, helping them succeed by focusing on team development, sales strategy, and building effective sales processes that prioritize problem-solving over traditional product-centric approaches.
Where to find Steve Reid:
LinkedIn: https://www.linkedin.com/in/steve-reid-csl/
Where to find Michael (Founder & CEO @ SellMeThisPen AI):
Email: [email protected]
LinkedIn https://www.linkedin.com/in/michaelocean/
Try SellMeThisPen AI @ https://www.sellmethispen.ai/
🌟 SellMeThisPen AI is the only all-in-one AI sales coaching platform that helps sellers in every step of their journey.
Before client calls - Role-play realistic sales conversations with AI to perfect your pitch and practice objection handling, without burning precious leads.
During client calls - Receive real-time guidance to handle objections consistently and get reminded to ask the right questions so you can win deals faster.
After client calls - Get unbiased feedback so you can improve next time. And it doesn't stop there—SMTP takes care of your notes and CRM updates so you can focus on selling instead of admin work.
47 min - #41 Better Is Better: Sales Excellence Through Practice | Denis Champagne on SellMeThisPen Pod
About the episode:
In this episode, Michael and Denis dive into the evolution of sales practices across three decades. They discuss why personalization requires understanding both seller motivations and buyer challenges, the importance of maintaining phone conversations in a digital world, and why building character through resilience matters more than pure sales skills for developing successful reps.
About the guest:
Denis Champagne is a seasoned sales coach and consultant who has spent over three decades in the trenches, from his early days selling furniture appointments as a teenager to managing telemarketing teams and running his own call center. Currently, Denis works as an executive coach across all levels of sales organizations, helping reps with prospecting, guiding managers through leadership challenges, and advising VPs on forecast accuracy while maintaining a focus on building character, resilience and coaching those who truly want to improve.
Where to find Denis Champagne:
LinkedIn: https://www.linkedin.com/in/denis-champagne/
Where to find Michael (Founder & CEO @ SellMeThisPen AI):
Email: [email protected]
LinkedIn https://www.linkedin.com/in/michaelocean/
Try SellMeThisPen AI @ https://www.sellmethispen.ai/
🌟 SellMeThisPen AI is the only all-in-one AI sales coaching platform that helps sellers in every step of their journey.
Before client calls - Role-play realistic sales conversations with AI to perfect your pitch and practice objection handling, without burning precious leads.
During client calls - Receive real-time guidance to handle objections consistently and get reminded to ask the right questions so you can win deals faster.
After client calls - Get unbiased feedback so you can improve next time. And it doesn't stop there—SMTP takes care of your notes and CRM updates so you can focus on selling instead of admin work.
41 min
About SellMeThisPen podcast
From the publisher's feed
At SellMeThisPen, we help sales leaders transform team performance without adding headcount or management overhead ✨
Our AI roleplay and coaching platform enables your reps to practice with realistic scenarios tailored to your use case, then receive personalized feedback after every interaction - real client calls or AI simulations.
In this podcast, SMTP's CEO and founder Michael Ocean is having conversations with top sales leaders and enablement experts to explore what it really takes to drive performance across go-to-market teams.