Creating Distance

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In this week’s episode of Creating Distance, Tom Alaimo sits down with Mikaela (Mohr) Lentz, GTM Strategy & Enablement Manager at Uber, to explore the rapidly evolving role of AI in modern sales. Together, they unpack how technology is reshaping the buyer–seller dynamic and redefining what effective selling looks like today.

Mikaela highlights a major shift: today’s buyers are more informed than ever, often researching sellers, companies, and solutions long before a conversation even begins. Because of this, she emphasizes the growing need for deeper preparation, sharper messaging, and a...

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In this week’s episode of Creating Distance, Tom Alaimo sits down with Tenny Tagg, Head of Sales - Customer Growth and Account Management at Lattice, for an insightful conversation about career growth, leadership, and the future of sales in an AI-driven world.

Tenny shares her inspiring journey from customer service to sales leadership, highlighting the pivotal role of mentorship in shaping her career. She introduces her leadership philosophy, DYAB (Do Your Absolute Best), and explains how this mindset has guided her approach to developing high-performing teams.

Tom an...

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In this week’s episode of Creating Distance, we feature Tom Alaimo’s recent appearance with Scott Finden, Top AE at Monday.com and Founder of BD Best Practices. Tom shares his journey from a shy beginner to a confident sales professional and trainer, emphasizing his philosophy of turning prospects into “raving fans” through research, creativity, and personal touches like handwritten notes and timely follow-ups.

They also discuss one of sales’ biggest challenges today: turning new knowledge into consistent habits. Tom offers practical strategies for building systems that stick, from blocking t...

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In this week’s episode of Creating Distance, Tom Alaimo sits down with Jordan Winston and Taylor Ouellette, founders of Not Your Dad's Media, to discuss the power of volume and persistence in achieving success. They explore how consistently producing a high quantity of work can lead to higher-quality results over time, turning effort into experience and mastery. Drawing inspiration from Hormozi’s thought-provoking quote, they encourage listeners to embrace high-volume efforts as a practical strategy for making success more attainable, even when early attempts feel imperfect.

The conversation also high...

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In this week’s episode of Creating Distance, Tom Alaimo sits down with Deb Jenson, a revenue enablement leader at IBM, to explore the evolving landscape of sales enablement. Deb shares her unique journey from a technical background to leading large sales teams, offering insights into the challenges and strategies of managing enablement at scale. She emphasizes the importance of personalization in sales and introduces her 'layer cake' model of enablement, which highlights the need for strong foundational skills and structured methodologies.

Deb also discusses the role of technology in en...

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In this week’s episode of Creating Distance, Tom Alaimo sits down with Christian Krause to explore the transition from corporate sales to entrepreneurship. Together, they dive deep into the power of personal branding on LinkedIn and how social selling is reshaping the modern sales landscape.

Christian shares actionable insights on video prospecting, the importance of consistent follow-up, and creative ways to motivate teams to adopt social selling. The conversation emphasizes that building a strong personal brand isn’t just a short-term strategy; it’s a long-term investment in credibility, connec...

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In this episode of Creating Distance, we feature Tom Alaimo’s recent appearance on the Sell Better Daily Sales Show with host James Buckley. Together, they explore the art of context first sales messaging and how authentic personalization, rather than relying on surface-level details, can create genuine conversations and lead to better response rates. Tom shares insights from his sales experience and offers listeners actionable advice to improve their outreach strategies.

We unpack the pitfalls of generic or AI-generated outreach and discuss how to identify meaningful buyer triggers, leverage signals, an...

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In this week’s episode of Creating Distance, Tom Alaimo dives deep into the critical topic of time and energy management for sales professionals. He emphasizes that mastering your schedule and maintaining high energy are just as important as learning the tactics of prospecting. Without these skills, even the best sales strategies can fall short.

Tom shares actionable strategies for prioritizing revenue-generating activities, building consistent prospecting habits, and creating “Outbound Mode,” distraction-free time blocks to maximize focus. He also explores the power of systems, task batching, and aligning work with your e...

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In this week’s episode of Creating Distance, Tom Alaimo dives into strategies for sales professionals to successfully close out the year, with a strong focus on the fourth quarter. He emphasizes the importance of reflection, looking back at past performance to identify strengths and opportunities, and setting clear, actionable goals to finish strong.

Tom shares practical insights on prospecting and building a healthy pipeline, while also highlighting the power of referrals in accelerating sales momentum. Beyond tactics, he stresses the role of mindset and energy in driving success, encouraging sal...

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In this episode of Creating Distance, we feature Tom Alaimo’s recent appearance on the Sell Better Daily Sales Show with host Leslie Douglas. Where they dive deep into the art and science of cold emailing with expert guests who share their proven strategies for boosting reply rates. Discover why the traditional, fully templated cold email is no longer effective and how a blend of personalization and creativity can set your outreach apart.

Key topics include:

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In this episode of Creating Distance, host Tom Alaimo sits down with Jenn Nguyen, a leader in Account Management at PandaDoc, to explore her career journey from affiliate marketing to managing high-performing teams. Jenn shares her leadership philosophy rooted in mentorship, emotional intelligence, and core values, while discussing how the role of Account Management has evolved, why customer value matters more than ever, and how AI is reshaping efficiency in sales. She also highlights the importance of curiosity, creativity, and setting personal boundaries, introducing the concept of work-life rhythm as a healthier a...

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In this week’s episode of Creating Distance, Tom Alaimo goes live with Millennium Alliance and shares his sales strategies with a mixed sales team. He emphasized the importance of personalization, using multiple channels like email, LinkedIn, and direct mail, and leveraging data to optimize outreach sequences. Tom suggested using internal camouflage in subject lines and focusing on the prospect's top three problems. He also highlighted the effectiveness of creative tactics like crumpled letters and videos. The team discussed their current outreach methods, including email cadences and texting, and explored the potential of...

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In this week’s episode of Creating Distance, Tom Alaimo sits down with Sriharsha Guduguntla and Atul Raghunathan, Co-Founders of Hyperbound, to explore their journey in building an innovative AI sales platform. They dive into the early challenges of finding product-market fit and emphasize the crucial role of persistence in sales success. The conversation highlights their strategies for identifying ideal customers, navigating the steep learning curve of sales, and striking the right balance between in-person and remote selling. Additionally, Sriharsha and Atul share valuable insights on hiring and managing team dynamics as the...

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In this week’s episode of Creating Distance, Tom Alaimo sits down with Jacco van der Kooij, Founder of Winning By Design, to explore the evolving landscape of sales. They dive into the transformative impact of AI on revenue growth and the critical role of cultivating strong customer relationships. Jacco shares his journey in building Winning By Design, highlighting the contrasts between AI-native and traditional SaaS companies, and underscores the importance of a user-centric approach to product development. Throughout the conversation, he stresses the power of passion in sales and the need to...

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In this week’s episode of Creating Distance, Tom Alaimo dives deep into how AI isn’t just the future of sales — it’s transforming the way top teams work right now.

We’re sharing highlights from our free live workshop where we reveal exactly how we’re using AI to supercharge our sales process.

You’ll learn:

Welcome Back to the Show! 

In this week’s episode of Creating Distance, Tom Alaimo sits down with Steve Travaglini to dive deep into the evolution of modern sales. They trace Steve’s path from BDR to CRO, highlighting the shift from traditional, high-volume tactics to a more refined, quality-first approach. The discussion covers how AI is transforming outreach, the power of storytelling in sales, and the importance of crafting unforgettable client experiences.

Steve and Tom also unpack key leadership themes—like empathy, co-discovery, and adaptability—as essential tools for today’s sales professionals. With a focus on...

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In this week’s episode of Creating Distance, Tom Alaimo sits down with Lisa Killeen, Enterprise Sales Leader at monday.com, to dive into her career journey and the key lessons she’s learned in sales leadership. They unpack the shift from product-led growth (PLG) to sales-led growth (SLG), highlighting the critical role of business acumen and the core skills needed to thrive in enterprise sales. Lisa offers practical strategies for impactful first calls, emphasizes the power of face-to-face meetings, and outlines her approach to strategic account planning. The conversation also explores leade...

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In this week’s episode of Creating Distance, Tom Alaimo reconnects with AJ Giaccia, who shares his journey from being an individual contributor in sales to stepping into a leadership role at Tines. AJ discusses the personal growth he has experienced, including becoming a father, and how this has influenced his leadership style. He emphasizes the importance of mastering the fundamentals of sales, effective time management, and building a strong team culture. AJ also highlights the significance of technical acumen in sales and shares insights on coaching and development strategies for his tea...

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In this week’s episode of Creating Distance, host Tom Alaimo sits down with Miriam O'Donnell, Enterprise AE at Pocus, to explore her dynamic journey through the world of sales. Miriam shares insights from her time at various companies and offers a candid look at the challenges and rewards of being a founding account executive at a startup. The conversation dives into modern sales strategies, building positive buyer experiences, and what it takes to hire great sales reps. With a focus on the evolving tech sales landscape, Miriam highlights the importance of rel...

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In this episode, we sit down with Colum Lundt—entrepreneur, sales leader, and CEO of CoachEm—to explore his unexpected journey into the world of sales and how it led him to build a platform that’s redefining sales management.

Colum shares how early failures shaped his mindset, why referrals and in-person relationships still matter, and the crucial role managers play as coaches, not just task managers. We dive into how technology can empower better coaching, and what the future holds for sales leadership in a rapidly evolving business landscape.

Wh...

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In this conversation, Anne Pao shares her extensive experience in RevOps and GoToMarket strategies, discussing the importance of RevOps in scaling businesses and the dynamics between sales and operations. She emphasizes the need for companies to recognize when to implement RevOps and the value of building strong relationships within teams. Anne also provides insights from her perspective as a buyer, highlighting best practices for sales engagement and the tools that can enhance RevOps effectiveness. The discussion concludes with Anne's thoughts on prioritizing time and energy, as well as recommendations for future guests o...

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In this episode, Hayes Davis shares his unique journey from software engineer to sales technology leader. He introduces the concept of the “10x rep,” inspired by the legendary “10x engineer,” and explores how AI is reshaping the future of sales. Through a compelling thought experiment, Hayes breaks down different paths to achieving 10x sales performance—whether through increased volume, higher deal sizes, or improved efficiency. The conversation also delves into the evolving nature of sales strategies, the role of automation, and why adaptability and skill development are critical in today’s fast-changing sales environ...

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In this week’s episode, we sit down with Keith Rabkin, President of PandaDoc, as he reflects on his diverse career journey through companies like Google, YouTube, J&J, and Adobe. Keith shares how he transitioned into sales and developed an operational, strategic approach to sales leadership. He emphasizes creating multiple career paths, cultivating urgency, and applying practical business school lessons.

Keith dives into leadership principles, highlighting the importance of tenacity, adaptability, and hiring for grit. He outlines strategies for managing large teams, setting priorities, and using effective sales tactics—parti...

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In this episode of the Creating Distance podcast, host Tom Alaimo reflects on key takeaways from the recent CRO Pavillion Summit with over 200 B2B tech CROs. The discussion dives into the changing landscape of sales, focusing on how AI is driving sales efficiency, the shifting preferences of Gen Z buyers, and the emergence of new go-to-market strategies. Tom highlights the need for adaptability in the CRO role and introduces the concept of user-led growth as a rising sales model. He also shares data-driven insights on current sales performance and practical strategies f...

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In this week’s episode, we’re joined by Sarah Kiley, Chief Sales Officer at ChurnZero, who shares her remarkable journey from her early days as a passionate Girl Scout cookie seller to becoming a strategic leader in the world of B2B sales. Sarah takes us through the key milestones of her career, reflecting on how her childhood experiences helped shape her competitive spirit, entrepreneurial mindset, and authentic leadership style. She opens up about the core values that have guided her—curiosity, transparency, and continuous learning—and how these principles have helped he...

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In this week’s episode, we sit down with Nate Vogel, a veteran sales leader and enablement strategist, as he shares the story of his remarkable journey—from humble beginnings selling lemonade to leading high-performing sales and enablement teams at industry giants like Southwestern Advantage, Tableau, and Gong. Nate opens up about the values that have guided his career, including the importance of service in sales, the impact of strong mentorship, and the role of authentic relationships and networking in long-term success.

Nate dives deep into the evolution of sales enabl...

Hey listeners! 

In this conversation, Nora Hanagan-Breen shares her unique journey into sales, starting from her non-traditional background and experiences abroad. Her experience in Turkey helped her realize her passion for working with people. She discusses the evolution of sales training, her transition into leadership, and the insights gained from her time at HubSpot and Outreach. Nora emphasizes the importance of ownership in sales, the challenges of balancing work and parenthood, and offers valuable advice for aspiring sales professionals. Nora believes that every deal and conversation is unique, requiring tailored approaches. She encourages aspiring sales professionals to i...

Hey listeners! 

In this week's episode, Sean and Tom discuss Sean's career progression, particularly his recent promotion to Director of Sales at Webflow, and the importance of maintaining a work-life balance. Sean highlighted his achievement of having zero voluntary attrition in his team over two and a half years, attributing it to his focus on personal and professional development. Tom and Sean also discussed the importance of maintaining a work-life balance, especially during high-pressure sales periods.They also shared their personal experiences, with Sean discussing his journey from acting to sales and the importance of outworking and o...

🎙️ We're Back – And Better Than Ever!🎙️

Hey listeners! 

After a little time away, I am thrilled to announce the official relaunch of the podcast. Not only a relaunch, but a rebrand. 

Creating Distance — is your go-to space for unfiltered conversations, expert insight, inspiring stories, and helpful tips.

I have been cooking up something special behind the scenes: fresh content, new guests, a sharper focus, and the same passion you’ve come to expect. Whether you’re a longtime listener or just tuning in, get ready for weekly episodes packed with personal development, sales, tr...

In this episode, Tom was invited as a guest on Sell Better Show.

Credits: This was a webinar that originally aired on the Sell Better Show.

If you enjoy the podcast, would you please consider leaving a short review on Spotify or Apple Podcasts?

It takes less than 60 seconds, and it really makes a difference in helping to grow this show and find the best guests possible for you.

Follow The Podcast:

Apple/Spotify: Millennial Sales

Twitter: TommyTahoe

Instagram: TommyTahoe

YouTube: TA Sales<...

In this episode, Tom was invited as a guest on Sell Better Show.

Credits: This was a webinar that originally aired on the Sell Better Show.

If you enjoy the podcast, would you please consider leaving a short review on Spotify or Apple Podcasts?

It takes less than 60 seconds, and it really makes a difference in helping to grow this show and find the best guests possible for you.

Follow The Podcast:

Apple/Spotify: Millennial Sales

Twitter: TommyTahoe

Instagram: TommyTahoe

YouTube: TA Sales<...

In this episode, Tom was invited as a guest on Sell Better Show.

Credits: This was a webinar that originally aired on the Sell Better Show.

If you enjoy the podcast, would you please consider leaving a short review on Spotify or Apple Podcasts?

It takes less than 60 seconds, and it really makes a difference in helping to grow this show and find the best guests possible for you.

Follow The Podcast:

Apple/Spotify: Millennial Sales

Twitter: TommyTahoe

Instagram: TommyTahoe

YouTube: TA Sales<...

In this episode, Tom was invited as a guest on Sell Better Show.

Credits: This was a webinar that originally aired on the Sell Better Show.

If you enjoy the podcast, would you please consider leaving a short review on Spotify or Apple Podcasts?

It takes less than 60 seconds, and it really makes a difference in helping to grow this show and find the best guests possible for you.

Follow The Podcast:

Apple/Spotify: Millennial Sales

Twitter: TommyTahoe

Instagram: TommyTahoe

YouTube: TA Sales<...

In this episode, Blake Hudson engages in a conversation with Brandon Baker.

If you enjoy the podcast, would you please consider leaving a short review on Spotify or Apple Podcasts?

It takes less than 60 seconds, and it really makes a difference in helping to grow this show and find the best guests possible for you.

Follow The Podcast:

Apple/Spotify: Millennial Sales

Twitter: TommyTahoe

Instagram: TommyTahoe

YouTube: TA Sales

Website: TASales.co

In this episode, Tom was invited as a guest on the Mailshake podcast to discuss the inner game of sales.

If you enjoy the podcast, would you please consider leaving a short review on Spotify or Apple Podcasts?

It takes less than 60 seconds, and it really makes a difference in helping to grow this show and find the best guests possible for you.

Follow The Podcast:

Apple/Spotify: Millennial Sales

Twitter: TommyTahoe

Instagram: TommyTahoe

YouTube: TA Sales

Website: TASales.co

In this episode, Tom dives into an insightful interview with Zach Wright, the CRO and Co-founder of Syft.

If you enjoy the podcast, would you please consider leaving a short review on Spotify or Apple Podcasts?

It takes less than 60 seconds, and it really makes a difference in helping to grow this show and find the best guests possible for you.

Follow The Podcast:

Apple/Spotify: Millennial Sales

Twitter: TommyTahoe

Instagram: TommyTahoe

YouTube: TA Sales

Website: TASales.co

In this episode, Tom engages in a conversation with JR Butler, an entrepreneur dedicated to assisting athletes and veterans in entering the field of sales.

If you enjoy the podcast, would you please consider leaving a short review on Spotify or Apple Podcasts?

It takes less than 60 seconds, and it really makes a difference in helping to grow this show and find the best guests possible for you.

Follow The Podcast:

Apple/Spotify: Millennial Sales

Twitter: TommyTahoe

Instagram: TommyTahoe

YouTube: TA Sales

Website...

In this episode, Tom was invited as a guest on The Happily Ambitious Podcast where he shared valuable lessons and insights gained from his life journey.

If you enjoy the podcast, would you please consider leaving a short review on Spotify or Apple Podcasts?

It takes less than 60 seconds, and it really makes a difference in helping to grow this show and find the best guests possible for you.

Follow The Podcast:

Apple/Spotify: Millennial Sales

Twitter: TommyTahoe

Instagram: TommyTahoe

YouTube: TA Sales

...

In this episode, Tom interviews Trent Dressel, who shares his experience of making 60,000 cold calls, earning $300K at the age of 26, and ultimately getting fired as an AE.

If you enjoy the podcast, would you please consider leaving a short review on Spotify or Apple Podcasts?

It takes less than 60 seconds, and it really makes a difference in helping to grow this show and find the best guests possible for you.

Follow The Podcast:

Apple/Spotify: Millennial Sales

Twitter: TommyTahoe

Instagram: TommyTahoe

YouTube: TA Sales<...

In this episode, Tom, Alex & Clara announce "The Arise Retreat". If you enjoy the podcast, would you please consider leaving a short review on Spotify or Apple Podcasts? It takes less than 60 seconds, and it really makes a difference in helping to grow this show and find the best guests possible for you. Follow The Podcast: Apple/Spotify: Millennial Sales Twitter: TommyTahoe Instagram: TommyTahoe YouTube: TA Sales Website: TASales.co