The Future of Selling – Details, episodes & analysis

In this episode of The Future of Selling, host Rick Smith is joined by Michael Gallagher, founder of the Stevie Awards and co-founder of two AI-driven companies: Reqsy and ImageShield.

Michael shares why recognition matters more than ever in an AI-powered world, how storytelling is the key to standing out, and why building your personal brand is crucial—especially for early-career sales professionals facing automation threats.

🔥 Key Topics:

Why Michael launched the "Oscars for Business" in the shadow of Enron

How AI is changing sales recognition—and how to use it wisely

How to tell a story that gets noticed (and wins awards)

Advice for sales reps who want to future-proof their careers

💡 Whether you’re a seller, a team leader, or just curious about the future of recognition and AI, this conversation will leave you with clear, practical takeaways.

Connect with Michael Gallagher https://www.linkedin.com/in/michael-gallagher-a8b785/
Nominate a Sales Pro for a Stevie Award: https://stevieawards.com//sales

Connect with Rick Smith https://www.linkedin.com/in/rick-smith-094b29b
Connect with Conquer https://conquer.io/

Cold outreach is broken—and this founder has a plan to fix it.
In this episode of The Future of Selling, we explore what happens when you stop spamming inboxes and start respecting your prospects.

Our guest is Ryan O'Hara, founder of Pitchfire, a paid-prospecting platform that flips traditional sales outreach on its head. Instead of begging for time, reps pay for responses—and it’s working. With reply rates up to 60% and meetings booked in just 3 pitches, this is not your average cold outreach conversation.

🎯 We cover:
– Why reply rates have plummeted and how to turn the tide
– The difference between buying a meeting vs. buying a response
– How creativity (like sending piano songs!) builds trust
– What “zero-click marketing” and personal branding mean for sellers
– Why paid prospecting could actually be more ethical
– The future of B2B sales, AI, and buyer-led deal rooms
– A real story about how a cold call led to a life-changing conversation

Whether you lead a sales team or carry a quota, this conversation will challenge the way you think about outreach.

Connect with Ryan O'Hara https://www.linkedin.com/in/ryanmohara/
Connect with Pitchfire https://www.pitchfire.com/

Connect with Rick Smith https://www.linkedin.com/in/rick-smith-094b29b
Connect with Conquer https://conquer.io/

In this episode of The Future of Selling podcast, host Rick Smith sits down with Andrew "AD" D’Agostino, a sales enablement leader with deep expertise in aligning teams, simplifying processes, and driving revenue growth. With over 14 years of experience, AD has navigated the startup journey, scaled revenue to $50M, led through 10+ acquisitions, and now plays a critical role in sales enablement at Conquer.

💡 Key Topics Covered:
✅ What sales enablement really means and why it’s more than just training
✅ The top three components of a high-impact sales enablement strategy
✅ How to align sales, marketing, and customer success with a common language
✅ The role of ruthless qualification in boosting deal velocity 🚀
✅ The game-changing impact of AI on coaching and sales enablement
✅ Tools and strategies to cut friction and increase flow in the selling process

AD shares real-world insights, practical frameworks like MEDDIC and force management, and actionable takeaways for sales enablement professionals looking to simplify, align, and drive results.

🔔 Don't forget to like, comment, and subscribe for more insights from top sales and enablement leaders!

 📢 Learn more about Conquer
📲 Connect with Andrew D’Agostino
📲 Connect with Rick Smith

🚀 What makes a great mentor? How is mentorship different from coaching? And how can sales leaders build a culture of mentorship that drives long-term success?

In this episode of The Future of Selling, host Rick Smith sits down with Brian Kludas, a sales enablement and leadership expert, to discuss the transformative power of mentorship in the sales industry.

🔹 What You’ll Learn in This Episode:
✅ The key differences between mentorship, coaching, and leadership
✅ The three levels of mentorship and how to apply them
✅ Why mentorship matters in scaling high-performing sales teams
✅ How to become an effective mentor (and mentee!)
✅ The biggest mistakes mentors make—and how to avoid them

📌 Whether you're an individual contributor, a sales leader, or a business executive, this conversation will give you actionable strategies to build stronger relationships and accelerate career growth.

Connect with Brian on LinkedIn

Connect with Rick on LinkedIn

Learn more about Conquer

🎧 Listen now and subscribe for more insights on the future of selling!

Why do deals really fall through? It’s not always about price or features—there’s often a deeper reason. In this episode of The Future of Selling, host Rick Smith sits down with Ron Carson, CEO of Thirdside and an expert in B2B marketing and Win/Loss analysis.

🔎 Key Takeaways from this Episode:

✅ The #1 reason sales teams lose deals (Hint: it’s not price!)
✅ Why sales discovery is more critical than ever—and how to do it right
✅ How Win/Loss reports uncover what CRM data doesn’t tell you
✅ The biggest blind spots in B2B sales—and how to fix them
✅ Why human connection still wins over AI-driven sales insights

Ron shares real-world insights from conducting thousands of Win/Loss interviews, revealing what buyers aren’t telling your sales team—but wish they would. If you're in sales, marketing, or customer success, this episode will change the way you think about deal wins and losses.

Connect with Ron on LinkedIn
Learn More About Thirdside
Read Thirdside's How-to Guide to for Win-Loss Research

Connect with Rick on LinkedIn
Learn More About Conquer

🚀 Don’t let another deal slip away—watch now and level up your sales game!

🔔 Subscribe to The Future of Selling for more expert insights!

🎙️ Future of Selling Podcast – Episode: Fixing Your B2B Sales Process with Jim Trimarco

📢 Welcome to the Future of Selling Podcast! Hosted by Rick Smith, Chief Customer Officer at Conquer, this podcast dives into the latest trends, challenges, and innovations in B2B sales. Whether you’re a sales leader, account manager, or founder, we bring you real-world strategies to navigate the evolving sales landscape.

🎧 In This Episode:
We sit down with Jim Trimarco (JT), a seasoned sales leader with over two decades of experience driving growth in SaaS and enterprise sales. JT shares his insights on what makes a winning B2B sales process and the key strategies sales teams need to stand out in competitive markets.

📌 Key Takeaways:
✔️ The #1 mistake most sales reps make—and how to fix it.
✔️ Why discovery is everything in sales.
✔️ The "Teachable Moment" and how it wins deals.
✔️ How to build credibility and trust in a crowded market.
✔️ Why "Time Kills All Deals" and how to keep urgency in the sales cycle.
✔️ How AI is transforming sales teams—and why you need to embrace it now.

📅 Timestamps:
00:00 – Introduction: Meet Jim Trimarco
02:00 – Fun facts about JT (including his love for fitness & food!)
06:00 – The fundamentals of a strong B2B sales process
10:35 – How to run an effective discovery call
12:31 – The power of the “Teachable Moment” in sales
18:13 – Emotional connection: Why buyers choose one company over another
25:20 – Common mistakes B2B sales teams make
31:52 – AI & the future of sales—how it’s changing everything
36:32 – JT’s top 3 takeaways for new sales leaders

🎯 Who Should Listen?
🔹 Sales leaders looking to improve their team’s performance
🔹 Account executives and SDRs navigating complex B2B deals
🔹 Founders and entrepreneurs scaling their sales process
🔹 Anyone interested in the future of selling

🔗 Connect with Us:
📌 Guest: Jim Trimarco
🎙️ Host: Rick Smith
💡 Learn More About Conquer

🔥 Don’t Forget to Like & Subscribe! If you found this episode valuable, hit the like button, subscribe, and leave a comment with your biggest takeaway!

#FutureOfSelling #B2BSales #SalesLeadership #SalesProcess #SalesPodcast #AIinSales 🚀

Join Rick Smith, Chief Customer Officer at Conquer, as he sits down with Elizabeth Richardson—a seasoned B2B sales professional and a proud SMU alum—to dive deep into the power of women in sales and the unique qualities they bring to the table. 🌟

Key Highlights:
✨ Why women are outperforming men in sales roles.
✨ Breaking barriers: Overcoming underrepresentation in sales leadership.
✨ Work-life balance: Elizabeth shares her personal journey as a mom and sales leader.
✨ Practical advice for women looking to enter or grow in the sales industry.

📊 Did you know? Only 20% of B2B sales leadership roles are held by women, yet studies show they consistently exceed performance metrics. Elizabeth shares actionable steps to close this gap and create a supportive, inclusive environment.

💬 Let’s Talk: What challenges have you faced in sales, and how did you overcome them? Share your thoughts in the comments!

👉 Connect with us:
Elizabeth Richardson
Rick Smith

#TheFutureOfSelling #WomenInSales #Leadership #SalesPodcast #Inspiration

🎙️ Welcome back to The Future of Selling Podcast! 🎙️

In this episode, host Rick Smith, Chief Customer Officer at Conquer, sits down with Andy Smith, Senior Vice President of Sales at Talk Me Up, to explore the evolving landscape of sales communication. From leveraging AI for best-in-class communication skills to practical strategies for improving empathy, confidence, and engagement, this episode is packed with actionable insights for sales professionals.

What You’ll Learn:

• The "3 R’s of Sales Success" framework: Relationships + Results = Revenue
• Top communication pitfalls salespeople face and how to overcome them
• How AI-powered platforms like Talk Me Up are revolutionizing sales coaching
• Why empathy and personalization are critical in today’s buyer-driven market
• Actionable tips to enhance your communication skills and drive results

Andy also shares fascinating stories about his journey in sales, his passion for broadcasting high school sports, and his involvement with One Heart, a nonprofit supporting incarcerated youth.

👉 Connect with us:

• Andy Smith: TalkMeUp.co | LinkedIn
• Rick Smith: Conquer | LinkedIn

💡 Don’t forget to like, comment, and subscribe for more episodes that help you stay ahead in the ever-evolving world of sales! 🚀

#FutureOfSelling #SalesPodcast #AI #SalesCommunication #TalkMeUp #Conquer

In this episode of Future of Selling, host Rick Smith sits down with Jason Forrest, Founder and CEO of FPG (Forrest Performance Group) and one of the world’s top-ranked sales gurus. Jason shares his insights on the future of sales, from leveraging AI to mastering advanced communication skills. They discuss the importance of hiring the right people, creating custom sales training, and building a high-performing team with what Jason calls the “Coachable GUMP” formula—traits every top salesperson needs to succeed.

Jason also dives into the concept of mindset and explains how beliefs drive behaviors and, ultimately, sales outcomes. Learn why the salesperson of the future will need to combine AI-enhanced knowledge with strong communication skills and how leaders can build a culture that supports both. Packed with actionable tips and thought-provoking insights, this episode will inspire you to rethink sales training, recruitment, and personal growth.

Tune in to explore:

The “Coachable GUMP” formula: What makes a great salesperson

How to integrate AI into your sales process for a competitive edge

Why mindset is key and how to intentionally shift it for success

The unique challenges and opportunities of the next generation of sales professionals

How to drive 100% conversion rates and achieve a true “unfair advantage”

Connect with Conquer:
Website: https://www.conquer.io 
LinkedIn: https://www.linkedin.com/in/rick-smith-094b29b/

Connect with Forrest Performance Group:
Website: https://fpg.com/ 
LinkedIn: https://www.linkedin.com/in/jasonforrest/

Welcome to The Future of Selling podcast with Rick Smith, Chief Customer Officer at Conquer! In this episode, Rick chats with Harris Fanaroff, founder of Linked Revenue, about leveraging LinkedIn to build a personal brand and drive B2B growth. Harris shares insights on sales strategies, creating authentic connections, and the importance of consistency in content. He also offers practical tips for using LinkedIn, including optimizing profiles, using engagement strategies, and how AI may shape the future of social selling.

Connect with Conquer:
Website
LinkedIn

Connect with Linked Revenue:
Website
LinkedIn