In this episode, Rick talks discusses the evolving landscape of sales enablement with Brian Trautschold, co-founder of Ambition, a leading sales performance management platform.

Brian shares his entrepreneurial journey—from coffee runs and copy machines at UBS to co-founding multiple startups and building Ambition into a company that transforms sales teams through coaching, gamification, and trust.

If you're a sales leader navigating the complexities of scaling your team or thinking about how AI and manager enablement will shape the next decade of performance, this is a must-listen conversation.

Connect with Brian Trautschold: https://www.linkedin.com/in/brian-trautschold-97518219/
Check out Ambition: https://ambition.com/

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

In this high-energy and deeply insightful episode, Rick sits down with Amanda Rubin, Chief Revenue Officer at Wildfire and former EVP of Growth at Enthusiast Gaming. Together, they explore how authenticity is reshaping modern marketing, particularly through Amanda’s groundbreaking work connecting brands with communities on Discord.

Amanda explains how Wildfire is helping brands authentically integrate into Gen Z-focused communities—not through ads, but through meaningful dialogue, partnerships, and experiences. She also unpacks the difference between marketing vs. branding, why trust is the ultimate competitive advantage, and how startups should think about go-to-market strategy from day one.

In the second half of the episode, Amanda opens up about building her career as a woman in a male-dominated industry, overcoming imposter syndrome, and how she’s found purpose by blending strategic leadership with human connection. Her story is as real as her leadership style—and one that will resonate with professionals at every level.

🎧 Tune in for a masterclass in modern brand building—and how character and competence create career momentum.

Connect with Amanda Rubin: https://www.linkedin.com/in/amanda-j-rubin/
Check out Wildfire: https://www.getwildfire.gg/

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

Unlock the secrets to building high-performing sales teams and staying ahead of the curve! In this episode of The Future of Selling, host Rick Smith welcomes Phil Hernandez, Global VP of Sales at Taskus, to discuss what it takes to lead winning teams in today's evolving sales landscape.

Phil shares practical insights from his 20+ years of experience — from creating strong sales cultures and developing leadership skills, to harnessing the power of AI to scale faster. Whether you're building a new sales team or leading an established one, this episode is packed with real-world strategies you can use today.

In this episode:

• Why culture is the foundation of sales success
• How AI is reshaping sales enablement and customer engagement
• Hiring strategies that go beyond the resume
• Building resilience and learning through failure
• The future mindset every sales leader needs

If you're ready to grow yourself, your team, and your results, this episode is for you.

👉 Like, subscribe, and hit the bell to catch every episode of The Future of Selling!

Connect with Phil Hernandez: https://www.linkedin.com/in/hernandezphillip/
Learn more about Taskus: https://www.taskus.com/

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

#salesleadership #futureofsales #salesculture #AI #taskus #salescoaching #leadership

In this episode of The Future of Selling, Rick Smith sits down with Kara Smith Brown—CEO and Founder of LeadCoverage, Ironman triathlete, and author of The Revenue Engine. Kara shares her no-fluff, practical framework for aligning marketing with business outcomes by measuring volume, value, and velocity.

They dive deep into:

• Why most marketing-sourced data falls flat in the boardroom
• How to truly align sales and marketing through pipeline velocity
• The power of intent data, ABM, and programmatic media buying
• Her journey from corporate roles to entrepreneurship
• Why "share good news, track interest, and follow up" is the core of modern B2B marketing
• And yes, how she turned being underestimated into Ironman motivation

Whether you're a marketing leader, CRO, or entrepreneur looking to generate real pipeline with precision, this episode is packed with insights you can actually use.

📚 Grab Kara Smith Brown’s book The Revenue Engine: https://www.amazon.com/dp/1642259098/

📍 Catch Kara Smith Brown on the road at her nationwide workshop tour: https://info.leadcoverage.com/the-revenue-engine-workshop-2025

🤝 Connect with Kara Smith Brown on LinkedIn: https://www.linkedin.com/in/karasmithbrown/

💡 Learn More About Conquer: https://conquer.io/

🤝 Connect with Rick Smith on LinkedIn: https://www.linkedin.com/in/rick-smith-094b29b

In this episode of The Future of Selling, host Rick Smith dives into one of the most disruptive shifts shaping sales organizations today: Decentralized Talent (or "DeTal"). Joined by Conquer's Chief Revenue Officer Jim Trimarco (JT) and Chief Financial Officer Demian Costa, the conversation unpacks how companies are rethinking sales staffing, team structure, and global scalability.

From JT’s deep experience leading global sales organizations to Demian’s journey from Navy SEAL to CFO, this episode offers a unique perspective on what’s driving the evolution of modern sales teams—and why the traditional outsourcing model has failed.

🔍 Topics We Cover:

• What "decentralized talent" actually means and how it differs from traditional outsourcing
• Why global wage arbitrage is an opportunity, not a risk
• How to align remote, global teams with your company culture and goals
• The tech stack and leadership mindset needed to make DeTal work
• Why the Balkans could be the next big thing in talent sourcing
• Actionable takeaways for sales leaders looking to grow while cutting costs

Whether you're scaling a startup or leading a mature sales org, this episode breaks down how to reduce costs, maintain quality, and scale faster—without sacrificing culture or performance.

Learn More About Conquer

Connect with Rick Smith
Connect with Jim Trimarco
Connect with Demian Costa

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!