SellMeThisPen podcast

About the episode:

In this episode, Michael and Jackelyn dive into the art of effective sales coaching. They explore how building trust and asking the right questions trump telling answers, why coaching managers need more development than reps, and what it takes to create coaching sessions that drive both skill growth and mindset shifts.

About the guest:

Jackelyn Skudra has been in sales for over 20 years, starting as an individual contributor before moving into leadership roles, and now serves as VP of Sales at Xello. With a background in teaching and a passion for passing on knowledge, she's transformed her early aspiration of becoming a math teacher into a successful career developing and coaching high-performing sales teams.

Where to find Jackelyn Skudra:

LinkedIn: https://www.linkedin.com/in/jackelynskudra/ 

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.

About the episode:

In this episode, Michael and Brian dive into building resilient sales teams through coaching, exploring why continuous feedback matters more than one-off training sessions. They discuss how effective coaching requires understanding individual motivations, the importance of leading by example rather than authority, and why partnering with product teams can amplify coaching success across the organization.

About the guest:

Brian Looney is a 20+ year sales veteran who's worn every hat in revenue organizations, from individual contributor to founder and CRO, with deep expertise in SaaS and intellectual property. He recently founded Clozrr, where he helps startups and emerging growth companies build and scale their sales organizations through fractional leadership, coaching, and go-to-market strategy.

Where to find Brian Looney:

LinkedIn: https://www.linkedin.com/in/brianlooney/ 

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.

About the episode:

In this episode, Michael and Amir dive into the realities of working with sales agencies and marketplace dynamics. They explore why companies should embrace both in-house and agency talent, how to set realistic expectations when hiring agencies and why being specific about your business challenges matters more than generic lead generation promises.

About the guest:

Amir Reiter is a seasoned sales leader and entrepreneur who built his career from door-to-door sales to leading CloudTask, a marketplace connecting companies with revenue agencies, software, and talent. With experience selling everything from vacuum cleaners to surgical robotics and enterprise software like NetSuite, Amir now helps businesses make better buying decisions through his "Home Depot of RevOps" platform that hosts over 300 agencies, 1000 software solutions, and 500 revenue professionals.

Where to find Amir Reiter: 

LinkedIn: https://www.linkedin.com/in/amirreiter/ 

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.

About the episode:

In this episode, Michael and Ryan dive into how different companies approach sales training, from door-to-door at Vivint to enterprise at IBM. They explore why structured training programs work differently at companies of various sizes, and share insights on transitioning from founder-led sales to building scalable sales teams.

About the guest:

Ryan Ing has grown from selling door-to-door at Vivint to leading sales at tech giants like IBM, Oracle, and Shopify, along with helping several startups like Superlink and Tempo Labs build their sales functions. He's now working as a fractional head of sales for B2B SaaS companies, helping them transition from founder-led sales to scalable processes, while also being known for running curated events for the Toronto Tech community.

Where to find Ryan Ing:

LinkedIn: https://www.linkedin.com/in/ryaning/ 

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.

About the episode:

In this episode, Michael and Chris dive into everboarding and the importance of continuous learning in sales teams. They explore why having a strong enablement culture is crucial for revenue growth, how AI can accelerate learning programs, and Chris shares candid stories about leadership mistakes that shaped his approach to building high-performing sales teams.

About the guest:

Chris Bondarenko is a seasoned revenue leader with extensive experience leading teams as VP of Sales and now CRO of North America at 360Learning, where he champions the importance of continuous learning and everboarding. Chris has built a remarkable track record of developing  sales teams through strategic enablement partnerships, skills frameworks, and creating a culture of learning that drives sustainable growth.

Where to find Chris Bondarenko:

LinkedIn: https://www.linkedin.com/in/chrisbondarenko/ 

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.

About the episode:

In this episode, Michael and Neman dive into the essentials of high-touch onboarding programs in enterprise sales, breaking down why personalization and structured learning are crucial for new hire success. They explore how treating enablement as a competitive edge through detailed onboarding plans and role-specific training can transform new hires into trusted advisors, even in resource-constrained environments.

About the guest:

Neman Syed is a seasoned L&D professional, who previously led enterprise training at BlackBerry before joining MATRIXX Software as Sales Enablement Manager, where he now drives high-touch onboarding programs while running his own consulting firm focused on training and development. His journey started in engineering before transitioning to corporate training, where he developed a passion for building high-touch onboarding programs that transformed raw talent into enterprise-ready sales professionals.

Where to find Neman Syed:

LinkedIn: https://www.linkedin.com/in/nemansyed/ 

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.

About the episode:

In this episode, Michael and Brooke dive into the concept of Everboarding and why traditional onboarding isn't cutting it anymore. They explore how continuous learning programs can transform sales enablement, break down common misalignments between enablement teams and sales leaders, and discuss practical ways to create engaging training that actually sticks with sales teams.

About the guest:

Brooke Bachesta is a dynamic enablement leader who started as an SDR, moved into management, and led enablement at brands like Outreach before becoming the Director of Learning Design at JLL. With experience across SaaS and real estate industries, she's now focused on building scalable, structured enablement programs that drive results through continuous learning and development.

Where to find Brooke Bachesta:

LinkedIn: https://www.linkedin.com/in/brooke-bachesta/ 

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.

About the episode:

In this episode, Michael and Adriana dive into the unique challenges of leading engineering enablement after transitioning from sales teams. They explore how measuring impact differs between technical and revenue teams, the importance of letting people fail safely, and why enablement leaders should encourage their teams to be proactively curious about the functions they support.

About the guest:

Adriana Romero is a seasoned enablement leader who transitioned from engineering to sales and now leads engineering enablement at OpenText, where she manages a team of eight supporting over 7,000 engineers globally. With 26 years of experience spanning systems engineering, sales, and enablement across companies like Salesforce and OpenText, Adriana brings a unique perspective on bridging technical and revenue teams while fostering a culture of continuous learning and growth.

Where to find Adriana Romero:

LinkedIn: https://www.linkedin.com/in/adrianaromero/ 

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.

About the episode:

In this episode, Michael and Michelle dive into the realities of rolling out sales methodologies in enterprise organizations. They discuss why getting stakeholder buy-in is crucial before implementation, how to blend new methodologies with existing processes, and why keeping customer experience at the center of methodology choices leads to better outcomes.

About the guest:

Michelle Curtis is an enablement leader with extensive experience in education and sales, currently serving as the Director of GTC Programs at Polaris and participating in multiple enablement communities such as Revenue Enablement Society and Enablement Squad. Her unique journey from education to enablement spans over a decade, where she's been driving successful sales methodology implementations across organizations.

Where to find Michelle Curtis:

LinkedIn: https://www.linkedin.com/in/michelle-curtis/ 

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.

About the episode:

In this episode, Michael and Nicole dive into the realities of go-to-market team alignment and the crucial role of enablement in driving organizational success. They discuss why enablement should be the central force behind cross-functional initiatives, from SKO planning to CRM optimization, and share practical insights on building effective partnerships across marketing, RevOps, and sales teams.

About the guest:

Nicole Ward is a revenue enablement leader with over 15 years of experience across financial services, telecommunications, enterprise SaaS, and HCM industries, recently recognized as the Enablement Leader of the Year by Seismic. Currently leading the Growth team at OSV within the Workday ecosystem, Nicole has established enablement as a strategic pillar for cross-functional success.

Where to find Nicole Ward:

LinkedIn: https://www.linkedin.com/in/nicole-ward-enablement/ 

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.