About the episode:
In this episode, Michael and Gail dive into why enablement is more critical than ever despite AI hype and recent industry upheaval. They talk about how enablement teams can prove their value, why building confidence and removing obstacles is at the core of the role, and how AI can actually empower enablement professionals to be more strategic instead of replacing them.
About the guest:
Gail Behun is a passionate enablement leader who transitioned from being a sales leader for nine years to founding her own practice, driven by her belief that enablement is a force multiplier when done right. She served as president of the Revenue Enablement Society until last year, where she connected with enablement professionals across the country and now advocates for the community through coaching, LinkedIn engagement, and helping both enablers and CROs maximize their impact together.
Where to find Gail Behun:
LinkedIn: https://www.linkedin.com/in/gailbehun/
Where to find Michael (Founder & CEO @ SellMeThisPen AI):
Email: michael@sellmethispen.ai
LinkedIn https://www.linkedin.com/in/michaelocean/
Try SellMeThisPen AI @ https://www.sellmethispen.ai/
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.
The result?
👉 Faster onboarding
👉 Consistent methodology adoption
👉 Continuous skill development that scales across your entire team.
Your reps get unlimited practice in a safe environment, real-time call assistance, and objective coaching that reinforces your sales framework. No more “hoping training sticks”, see measurable improvement in deal outcomes.
About the episode:
In this episode, Michael and Dina break down the real stages of change management and why most transformation projects fail before they even start. They explore how to gain leadership buy-in beyond just "we need AI," why enablement needs to manage up with data instead of gut feelings, and how to create actual adoption instead of just rolling out more training that nobody uses.
About the guest:
Dina Berger is a sales enablement veteran with over 11 years of experience who made an unconventional career pivot from university professor to leading enablement teams at organizations like Amazon Web Services, where she currently focuses on change management for product launches. With deep expertise in learning development, field enablement, and driving organizational transformation, Dina specializes in helping teams navigate complex change initiatives and build scalable enablement strategies that drive adoption and results.
Where to find Dina Berger:
LinkedIn: https://www.linkedin.com/in/dinabergerkoecher/
Where to find Michael (Founder & CEO @ SellMeThisPen AI):
Email: michael@sellmethispen.ai
LinkedIn https://www.linkedin.com/in/michaelocean/
Try SellMeThisPen AI @ https://www.sellmethispen.ai/
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.
The result?
👉 Faster onboarding
👉 Consistent methodology adoption
👉 Continuous skill development that scales across your entire team.
Your reps get unlimited practice in a safe environment, real-time call assistance, and objective coaching that reinforces your sales framework. No more “hoping training sticks”, see measurable improvement in deal outcomes.
About the episode:
In this episode, Michael and Bryan dive into how insurance agencies can thrive in an increasingly regulated and competitive market by embracing AI and building a culture of continuous learning. They discuss why process beats price in today's landscape, how to get buy-in from skeptical high performers, and why AI tools should amplify leaders rather than replace them.
About the guest:
Bryan Dinklenburg is the Director of Operations at L&T Agency Group Inc, where he's been since 2005, with a BA in organizational leadership from Arizona State University and a passion for developing people and processes. Bryan is leading his 45-person team through the rapidly evolving insurance landscape by leveraging AI tools and creating a culture where training, development, and continuous improvement are at the core of driving results.
Where to find Bryan Dinklenburg:
LinkedIn: https://www.linkedin.com/in/bryan-d-38179518a/
Where to find Michael (Founder & CEO @ SellMeThisPen AI):
Email: michael@sellmethispen.ai
LinkedIn https://www.linkedin.com/in/michaelocean/
Try SellMeThisPen AI @ https://www.sellmethispen.ai/
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.
The result?
👉 Faster onboarding
👉 Consistent methodology adoption
👉 Continuous skill development that scales across your entire team.
Your reps get unlimited practice in a safe environment, real-time call assistance, and objective coaching that reinforces your sales framework. No more “hoping training sticks”, see measurable improvement in deal outcomes.
About the episode:
In this episode, Michael and Tim dive into why account management is the most underappreciated role in SaaS and how to fix it. They discuss why AMs need to be in the room from day one, how to turn around at-risk accounts, and why companies need to start investing in post-sales teams the same way they invest in new business acquisition.
About the guest:
Tim Work is a Senior Director at Actabl with 20 years of experience in sales leadership, specializing in account management and customer success across B2B organizations. He's passionate about transforming AM from a transactional role into a strategic revenue-generating function and helps companies protect their base while driving expansion in today's competitive landscape.
Where to find Tim Work:
LinkedIn: https://www.linkedin.com/in/tim-work-revenue-enablement/
Where to find Michael (Founder & CEO @ SellMeThisPen AI):
Email: michael@sellmethispen.ai
LinkedIn https://www.linkedin.com/in/michaelocean/
Try SellMeThisPen AI @ https://www.sellmethispen.ai/
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.
The result?
👉 Faster onboarding
👉 Consistent methodology adoption
👉 Continuous skill development that scales across your entire team.
Your reps get unlimited practice in a safe environment, real-time call assistance, and objective coaching that reinforces your sales framework. No more “hoping training sticks”, see measurable improvement in deal outcomes.
About the episode:
In this episode, Michael and Iulia dive into the identity crisis of RevOps and why it's stuck between strategic planning and endless admin work. They explore how to roll out AI tools the right way, why adoption beats features every time, and how fractional RevOps is becoming the new normal for companies doing more with less.
About the guest:
Iulia Tesfai is a seasoned RevOps professional with over 15 years of experience across SaaS companies in SaaS and supply chain, and recently transitioned to full-time fractional Head of RevOps after being laid off a year ago. She’ve founded RevTectonic, specializing in helping scale-ups untangle operational chaos while building strategic RevOps foundations that drive measurable revenue impact.
Where to find Iulia Tesfai:
LinkedIn: https://www.linkedin.com/in/iulia-tesfai-mba-84a06a1a/
Where to find Michael (Founder & CEO @ SellMeThisPen AI):
Email: michael@sellmethispen.ai
LinkedIn https://www.linkedin.com/in/michaelocean/
Try SellMeThisPen AI @ https://www.sellmethispen.ai/
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.
The result?
👉 Faster onboarding
👉 Consistent methodology adoption
👉 Continuous skill development that scales across your entire team.
Your reps get unlimited practice in a safe environment, real-time call assistance, and objective coaching that reinforces your sales framework. No more “hoping training sticks”, see measurable improvement in deal outcomes.
About the episode:
In this episode, Michael and Lisa dive into selling through downturns and why investing in people beats playing not to lose. They explore how to authentically rebrand yourself on LinkedIn, the power of understanding your buyers deeper than the competition, and why account managers need to be strategic ninjas who know more about customers and competitors than anyone else.
About the guest:
Lisa Honaker is a seasoned revenue leader with over 30 years of experience across Fortune 100 companies like FedEx and SaaS organizations including Highspot and Actabl, where she currently leads the account management organization. Lisa is passionate about building growth mindsets, leading through downturns, and helping revenue teams sell strategically by deeply understanding their customers and competitors.
Where to find Lisa Honaker:
LinkedIn: https://www.linkedin.com/in/lisa-honaker/
Where to find Michael (Founder & CEO @ SellMeThisPen AI):
Email: michael@sellmethispen.ai
LinkedIn https://www.linkedin.com/in/michaelocean/
Try SellMeThisPen AI @ https://www.sellmethispen.ai/
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.
The result?
👉 Faster onboarding
👉 Consistent methodology adoption
👉 Continuous skill development that scales across your entire team.
Your reps get unlimited practice in a safe environment, real-time call assistance, and objective coaching that reinforces your sales framework. No more “hoping training sticks”, see measurable improvement in deal outcomes.
About the episode:
In this episode, Michael and Kate dive into the realities of implementing AI in sales enablement, from building foundational knowledge before jumping into tools to managing the challenge of reps using their own AI solutions. They explore why starting with education beats rushing into adoption, how to measure real behavior change beyond just usage metrics, and why treating AI implementation like any other sales methodology requires proper change management and integration across the entire organization.
About the guest:
Kate Stringfield is a reformed seller turned enablement expert who spent nine years in sales before discovering her passion for enablement in 2019. At her last position as a Senior Manager of Enablement at Dialpad, she managed six enablers globally and focused on building strategic programs around emerging technologies like agentic AI to help sales teams change behavior and drive revenue outcomes.
Where to find Kate Stringfield:
LinkedIn: https://www.linkedin.com/in/kate-stringfield/
Where to find Michael (Founder & CEO @ SellMeThisPen AI):
Email: michael@sellmethispen.ai
LinkedIn https://www.linkedin.com/in/michaelocean/
Try SellMeThisPen AI @ https://www.sellmethispen.ai/
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.
The result?
👉 Faster onboarding
👉 Consistent methodology adoption
👉 Continuous skill development that scales across your entire team.
Your reps get unlimited practice in a safe environment, real-time call assistance, and objective coaching that reinforces your sales framework. No more “hoping training sticks”, see measurable improvement in deal outcomes.
About the episode:
In this episode, Michael and Shannon dive into the real talk about win-loss analysis and how to turn raw data into actionable insights that actually help sales teams close more deals. They explore why you need multiple data sources beyond CRM notes, how to build cross-functional alignment around customer feedback, and why giving sellers less content with more context beats drowning them in materials they'll never use.
About the guest:
Shannon Izquierdo is founder of the Prompt Insight Group, a consulting company focused on enablement and branding, with extensive experience at major companies like FedEx and Kinaxis where she specialized in using win-loss analysis and market insights to enhance sales content and processes. With a journalism background that evolved into a deep expertise in content strategy and sales enablement, Shannon helps organizations turn raw data into actionable insights that drive real results for their sales teams.
Where to find Shannon Izquierdo:
LinkedIn: https://www.linkedin.com/in/shannonizquierdo/
Where to find Michael (Founder & CEO @ SellMeThisPen AI):
Email: michael@sellmethispen.ai
LinkedIn https://www.linkedin.com/in/michaelocean/
Try SellMeThisPen AI @ https://www.sellmethispen.ai/
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.
The result?
👉 Faster onboarding
👉 Consistent methodology adoption
👉 Continuous skill development that scales across your entire team.
Your reps get unlimited practice in a safe environment, real-time call assistance, and objective coaching that reinforces your sales framework. No more “hoping training sticks”, see measurable improvement in deal outcomes.
About the episode:
In this episode, Michael and Matt dive into navigating AI transformation as a sales leader and why authentic human connections still matter most. They discuss how to stay relevant in a rapidly changing landscape, the importance of face-to-face meetings over endless AI tools, and why being genuinely curious and real with customers beats any sales trick in the book.
About the guest:
Matt Marshall is a startup sales veteran with over 20 years of experience scaling teams at companies like Embarcadero, Successfactors, Citrix, and Iterable, where he helped grow revenue from $1.5M to $75M. He's passionate about building authentic sales cultures and currently works in executive search and coaching, helping sales leaders navigate the rapidly evolving AI landscape while staying focused on human connections.
Where to find Matt Marshall:
LinkedIn: https://www.linkedin.com/in/mattlmarshall/
Where to find Michael (Founder & CEO @ SellMeThisPen AI):
Email: michael@sellmethispen.ai
LinkedIn https://www.linkedin.com/in/michaelocean/
Try SellMeThisPen AI @ https://www.sellmethispen.ai/
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.
The result?
👉 Faster onboarding
👉 Consistent methodology adoption
👉 Continuous skill development that scales across your entire team.
Your reps get unlimited practice in a safe environment, real-time call assistance, and objective coaching that reinforces your sales framework. No more “hoping training sticks”, see measurable improvement in deal outcomes.
About the episode:
In this episode, Michael and Rob dive into the evolving world of sales development and how AI is reshaping the game. They explore the balance between human connection and AI augmentation, why outbound is getting harder in today's noisy market, and how to build SDR teams that actually drive pipeline instead of just booking meetings.
About the guest:
Rob Lotzer is a seasoned sales development leader with extensive experience across major SaaS companies like Salesforce and various startups, currently leading North American SDR and BDR organizations at Clio, a leading Canadian legal tech company. With over 125 team members under his leadership, Rob focuses on building scalable sales development processes while exploring innovative approaches to integrate AI augmentation with human expertise in both inbound and outbound motions.
Where to find Rob Lotzer:
LinkedIn: https://www.linkedin.com/in/rob-lotzer-a4283215/
Where to find Michael (Founder & CEO @ SellMeThisPen AI):
Email: michael@sellmethispen.ai
LinkedIn https://www.linkedin.com/in/michaelocean/
Try SellMeThisPen AI @ https://www.sellmethispen.ai/
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.
The result?
👉 Faster onboarding
👉 Consistent methodology adoption
👉 Continuous skill development that scales across your entire team.
Your reps get unlimited practice in a safe environment, real-time call assistance, and objective coaching that reinforces your sales framework. No more “hoping training sticks”, see measurable improvement in deal outcomes.
About the episode:
In this episode, Michael and Nina dive into the realities of building enablement programs that actually drive behavior change and business impact. They explore why manager buy-in is crucial for sustainable success, how to design programs that stick beyond the initial rollout, and share a real case study of a career development program that achieved 70% promotion success through strategic champion building and peer-to-peer learning.
About the guest:
Nina LaRouche is a seasoned enablement leader with over a decade of experience who has built programs from the ground up across companies like ExactTarget (acquired by Salesforce) and Bazaarvoice, where she led a team of seven practitioners through tremendous company growth. Starting her career as an educator before transitioning into 15 years of sales, Nina combines her teaching background with deep sales experience to create impactful enablement programs that drive measurable business results and sustainable behavior change.
Where to find Nina LaRouche:
LinkedIn: https://www.linkedin.com/in/ninalarouche/
Where to find Michael (Founder & CEO @ SellMeThisPen AI):
Email: michael@sellmethispen.ai
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.
About the episode:
In this episode, Michael and Vanessa dive into the real challenges of driving revenue impact through enablement and why data maturity is crucial for success. They explore how to build executive alignment, get frontline manager buy-in, and move beyond just training to create sustainable behavior change that actually sticks.
About the guest:
Vanessa Metcalf is the VP of Revenue Enablement at Showpad who started her career carrying a bag in sales before discovering enablement over a decade ago when it wasn't even a well-established field. She's since zigzagged through sales leadership, rev ops, and enablement roles at companies like Top Hat and Docebo, building her expertise in the trenches and becoming a passionate advocate for proving enablement's measurable impact on revenue.
Where to find Vanessa Metcalf:
LinkedIn: https://www.linkedin.com/in/vanessametcalf/
Where to find Michael (Founder & CEO @ SellMeThisPen AI):
Email: michael@sellmethispen.ai
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.
About the episode:
In this episode, Michael Ocean and Michael Tristan explore how to scale enablement teams effectively while integrating AI and maintaining quality through rapid organizational changes. They dive into building global enablement operations, the art of upskilling your own team before serving others, and why a patient approach to AI adoption beats rushing into flashy tools.
About the guest:
Michael Tristan is the VP of Sales Enablement at Motive, where he leads a global team of nearly 40 people across the US and Pakistan, scaling enablement for a company approaching 450 million ARR and preparing for IPO. With a non-traditional background that includes training roles at Nordstrom and compliance work at Lyft, Michael has built his expertise around instructional design, leadership development, and AI-first enablement strategies that drive measurable results across enterprise sales organizations.
Where to find Michael Tristan:
LinkedIn: https://www.linkedin.com/in/mtristan/
Where to find Michael (Founder & CEO @ SellMeThisPen AI):
Email: michael@sellmethispen.ai
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.
About the episode:
In this episode, Michael and Marcus dive into the reality of AI adoption in sales organizations and why most teams aren't using it effectively despite knowing it's here to stay. They explore practical ways to lead AI implementation from the front, share specific prompts and frameworks for better deal management, and discuss how to cut through the noise in prospecting by focusing on relevancy over fancy personalization tricks.
About the guest:
Marcus Chan is a sales consultant and CEO of Venli Consulting who spent over 14 years in corporate America, getting promoted 12 times and hitting number one in every role before building a consultancy that helps organizations with 25+ AEs uncover millions in hidden revenue. With experience working with clients from startups to major companies like Salesforce, Google, and Microsoft, Marcus specializes in helping sales teams leverage AI and performance systems to drive results faster.
Where to find Marcus Chan:
LinkedIn: https://www.linkedin.com/in/marcuschanmba/
Where to find Michael (Founder & CEO @ SellMeThisPen AI):
Email: michael@sellmethispen.ai
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.
About the episode:
In this episode, Michael and Matthew dive into the realities of going through layoffs and how it shapes your leadership style. They explore why reflecting on tough moments like RIFs can make you a better leader, the importance of playing offense instead of just fixing today's problems, and how experiencing a layoff firsthand teaches you to lead with more humanity and emotional intelligence.
About the guest:
Matthew Loria is a seasoned sales leader with over 15 years of experience across high-growth companies like Groupon, Salesforce, and now Sprout Social as VP of Sales, where he's been for nearly five years. Having personally navigated through layoffs and challenging market shifts, Matthew brings a uniquely human-centered approach to sales leadership, focusing on building resilient teams and creating environments where people genuinely want to fight to be there.
Where to find Matthew Loria:
LinkedIn: https://www.linkedin.com/in/matthewloria/
Where to find Michael (Founder & CEO @ SellMeThisPen AI):
Email: michael@sellmethispen.ai
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.
About the episode:
In this episode, Michael and Jose dive into the realities of implementing AI transformation at scale for enterprise sales teams. They discuss Jose's journey from evaluating six different AI vendors to successfully rolling out AI tools across a 100+ person sales team, including the challenges of getting buy-in from leadership and frontline managers, and why choosing the right implementation partner matters more than just the technology.
About the guest:
Jose Carranza is the Head of Sales at Ergeon, leading a team of 100+ sellers and driving AI transformation across the organization for over two years. Starting as an industrial engineer and working his way through various roles from manufacturing to analytics, Jose has become a pioneer in implementing AI-driven sales strategies, achieving remarkable results like reducing training time by 66% and reaching 70% AI-generated code at his company.
Where to find Jose Carranza:
LinkedIn: https://www.linkedin.com/in/jose-a-carranza-h/
Where to find Michael (Founder & CEO @ SellMeThisPen AI):
Email: michael@sellmethispen.ai
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.
About the episode:
In this episode, Michael and Chloe dive into the real talk about customer success and why partnering with sales beats the traditional handoff approach. They explore what makes a great customer handoff, how to define success without overcomplicating it, and why everyone in the organization should own churn - not just CS teams.
About the guest:
Chloe Siegmann is a seasoned customer success leader with nearly 11 years at Houzz, where she currently serves as Head of Customer Success overseeing teams across the globe from onboarding to technical support. What makes her unique is her deep personal connection to Houzz's mission - her father was a residential architect, giving her firsthand insight into the struggles of home remodeling professionals that Houzz's platform aims to solve.
Where to find Chloe Siegmann:
LinkedIn: https://www.linkedin.com/in/chloe-siegmann/
Where to find Michael (Founder & CEO @ SellMeThisPen AI):
Email: michael@sellmethispen.ai
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.
About the episode:
In this episode, Michael and Jordan dive into the practical side of sales enablement and how to actually tie it to revenue impact. They discuss why enablement teams should own specific numbers like ramp metrics and pipeline generation, how to create real-world certifications that reps can immediately apply, and why adapting to modern buying behaviors is more crucial than ever in today's AI-driven sales environment.
About the guest:
Jordan Timothy is a seasoned sales professional turned enablement leader with experience across companies like InsideSales, Pluralsight, Chargebee, and now Semrush as their enablement expert. With deep roots in sales and a passion for leveraging AI and data science to drive results, Jordan focuses on tying enablement directly to revenue impact through metrics like ramp time, pipeline generation, and deal velocity
Where to find Jordan Timothy:
LinkedIn: https://www.linkedin.com/in/jordan-timothy-35814770/
Where to find Michael (Founder & CEO @ SellMeThisPen AI):
Email: michael@sellmethispen.ai
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.
About the episode:
In this episode, Michael and Haley dive into the realities of selling in service-based industries, exploring why buyers often mislead sellers and how having a solid process puts you on equal footing with prospects. They discuss the importance of being gutsy enough to run your own sales process, why sales managers need to get out of the field to make real observations, and how being wildly curious beats trying to convince people to buy.
About the guest:
Haley Haggerty is the president of Next Level Inc, a top 10 Sandler training franchise that's been around for 30 years, specializing in helping professional service organizations like consulting firms, engineering companies, and banks develop their sales capabilities. With two decades of experience training hundreds of professionals across 85+ industries, Haley focuses on empowering teams who "didn't go to school to be in sales" to build effective processes and overcome the mindset challenges that keep them from generating consistent business.
Where to find Haley Haggerty:
LinkedIn: https://www.linkedin.com/in/haley-haggerty-a403667/
Where to find Michael (Founder & CEO @ SellMeThisPen AI):
Email: michael@sellmethispen.ai
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.
About the episode:
In this episode, Michael and Lawrence dive into why traditional sales enablement often fails and how shifting to buyer enablement can actually drive revenue. They discuss the importance of developing writing skills for modern sellers, creating scalable buyer persona frameworks, and why most of the deal happens outside of sales calls - plus Lawrence shares some hard-won lessons from building enablement programs from scratch.
About the guest:
Lawrence Wayne O’Connor is a seasoned sales enablement expert with over a decade of experience who has built three different enablement programs from the ground up, supporting over 80 sellers globally across companies ranging from Apple to startups. Based in North London as an expat from Chicago, Lawrence now runs an independent consultancy focused on shifting from traditional seller training to buyer enablement, helping organizations create systems that influence buyer decisions rather than just coaching call behavior.
Where to find Lawrence Wayne O’Connor:
LinkedIn: https://www.linkedin.com/in/sirlawrencewayne/
Where to find Michael (Founder & CEO @ SellMeThisPen AI):
Email: michael@sellmethispen.ai
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.
