Mastering Modern Selling

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What if your next sales hire wasn’t human?

In this episode of Mastering Modern Selling, Isabella Bedoya, Co-CEO of Infinite AI, shares how sales teams are evolving by bringing AI “employees” into the mix. 

We go beyond the hype to explore practical use cases, ethical concerns, and the new skills sales pros must master to stay competitive in this AI-enabled landscape.

Whether you’re curious, cautious, or already experimenting with AI, this episode will help you think more strategically about the future of your sales team.

1. AI Employees Are Not Just Chatbots

 Isabella defines AI employees as task-performing agents embedded in workflows, not just tools you prompt, but systems that take action automatically across SMS, email, calls, and CRM. 

Think of them as digital team members handling your follow-ups, reactivations, and more.

2. Sales Reps Won’t Be Replaced, But They Will Be Repositioned

 AI handles the mundane and repetitive. 

Human reps move into strategist roles managing AI workflows, handling complex objections, and owning the emotional intelligence required to close.

3. Scaling Outreach Without Scaling Headcount

 Instead of hiring more SDRs or BDRs, companies are using AI to nurture leads, qualify opportunities, and schedule demos. 

It's not theory, it’s happening now, and Isabella walks us through real-world use cases like post-trade-show follow-ups and digital sales assistants.

4. Trust Isn’t Lost, It’s Rebuilt Through Value

 AI can build trust when it delivers consistently valuable, fast responses. If it’s trained well, it may outperform junior reps. 

Still, Isabella emphasizes that closing deals and earning emotional buy-in remains a human function for now.

5. New Role of the Seller: Coach, Manager, Strategist

 Sales pros will soon manage a team of AI agents, much like GMs in “Moneyball.” The skills to build prompts, tweak workflows, and analyze data will be key differentiators. 

Coaching AI and being coached by it will become a real scenario in sales teams.

The rise of AI employees in sales isn’t about replacing talent, it’s about redeploying it. As Isabella says, the reps who win will be the ones who embrace these tools, build systems, and create more space for the kind of selling only humans can do.

Sales isn’t going away. It’s getting smarter.

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In this powerhouse episode of Mastering Modern Selling, Brandon Lee, Tom Burton, and Carson Heady are joined by JD Miller, a seasoned sales executive turned private equity advisor. 

With six successful exits under his belt, JD brings a rare blend of operational insight and boardroom savvy. 

The discussion centers on how private equity firms evaluate and scale their portfolio companies—especially in the sales and marketing domains—and what sales leaders can do today to thrive in that high-expectation environment.

• Repeatability Is the Foundation of Scale

 JD highlights that scaling isn’t just about hiring more reps, it’s about implementing repeatable, measurable systems. 

When transitioning from a founder-led sales model to a broader team, companies need to get critical knowledge out of leaders’ heads and into structured playbooks. 

This is essential when growing from five sellers to two hundred. Without repeatable processes, scale isn’t sustainable.

• Sales Leadership Must Be Fluent in Data

 Today’s top CROs are expected to lead with data. 

Whether through deep CRM analysis, conversation intelligence, or funnel metrics, modern sales leaders need to understand how to break down growth targets into tactical, trackable levers. 

JD emphasized the need for CROs to either personally embrace analytics or work closely with RevOps to translate insights into strategy.

• “SMarketing”: Sales and Marketing as a Single Engine

 JD introduced the concept of "SMarketing", a true merger of sales and marketing into one go-to-market function. 

He shared real-world examples of aligning revenue goals with both teams’ activities and discussed how metrics like sales velocity can guide joint decision-making.

Bi-weekly check-ins and shared accountability are critical to keeping both teams rowing in the same direction.

• Messaging for the Modern Buyer

 Buyers today expect a well-informed, highly personalized approach. JD stressed the importance of showing up with a point of view rooted in research, data, and empathy. 

In a volatile economy, messaging must pivot from “growth at all costs” to helping buyers reduce risk and improve efficiency. 

Sales and marketing alignment ensures these themes are consistent across every touchpoint.

• Performance Plans: Tools for Growth, Not Punishment

 In JD’s view, performance improvement plans should be part of every employee's journey, not a disciplinary action. 

He advocates for quarterly development conversations that blend short-term performance goals with long-term career aspirations. 

JD Miller’s episode is a masterclass in bridging strategy and execution in modern selling. Whether you’re a CRO in a high-growth startup, a founder looking for investment, or a marketer working closely with sales, the principles JD shares can redefine how you scale. 

By focusing on repeatable systems, cross-functional alignment, and buyer-centric messaging, you can transform your sales motion into an engine that attracts not only customers, but also investors.

Don't miss out, your next big idea could be just one episode away!

This Show is sponsored by Fist Bump
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Check out our Live Show Events here: Mastering Modern Selling Live Show

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In this episode of Mastering Modern Selling, Brandon Lee and Tom Burton explore the evolving world of sales and marketing in 2025. 

They focus on the strategies that are truly working in today’s fast-changing landscape and provide actionable insights on how businesses can thrive. 

From content strategy to social selling and the importance of patience, this episode is packed with thought-provoking ideas for sales professionals.

• Patience in Sales and Content Strategy

In an era where instant gratification is the norm, Brandon and Tom emphasize the importance of patience. 

Consistency in content production and strategic engagement is essential for long-term sales success. 

Sales success doesn’t happen overnight. Consistent, value-driven content and outreach, especially on platforms like LinkedIn, build relationships that will pay off down the line​.

• The Importance of Authentic Content

One of the most significant shifts in content marketing is moving away from self-promotional messaging to authentic, educational, and human-centered content. 

Both Brandon and Tom stress that creating content that shares real-life experiences, teaches valuable lessons, and offers insights is far more effective than traditional sales pitches​.

• Social Media Strategy: Evolving with LinkedIn

LinkedIn continues to be a critical platform for B2B sales, but success requires more than just posting regularly. 

Brandon highlights that engagement with others’ posts, especially with meaningful comments, plays a crucial role in increasing visibility and positioning yourself as a thought leader. 

• Live Events and Podcasts as Trust Builders

Tom shares his experience with podcasts and live shows, especially in niche industries like manufacturing and wholesale distribution. 

These platforms have proven to build trust and establish authority, even if they don’t immediately generate sales. 

The real power lies in educating and nurturing relationships over time. The more you share and contribute to the community, the more likely you are to be seen as a trusted advisor when the time comes for the prospect to make a decision​.

• The Shift from Sales Pitches to Educational Conversations

Both hosts highlight the shift in how buyers view vendors. The focus is no longer on selling products but on educating potential clients and positioning yourself as a partner who helps solve their problems. This transition, however, requires patience and a long-term mindset​.

As we head deeper into 2025, the key to success lies in building meaningful relationships, whether through social media, live events, or thoughtful content. Patience, authenticity, and a focus on educating rather than selling will set businesses apart. 

As Brandon and Tom show, modern selling isn’t about immediate returns, it’s about laying the foundation for future growth.

If you want to be our next guest and share your insights, book your preferred date from this link Be Our Next Guest!

We’d love to have you on the show!

Don't miss out, your next big idea could be just one episode away!

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Check out our Live Show Events here: Mastering Modern Selling Live Show

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 In this episode of Mastering Modern Selling, where Brandon, Tom, and Carson were joined by the legendary Tim Wackel. With four decades of experience and stories from the trenches, Tim unpacked the habits and strategies that consistently deliver sales success—regardless of changing tools or trends.

In a world overwhelmed by automation and AI-generated pitches, Tim reminds us that the core of selling hasn’t changed: it’s still about people, curiosity, and meaningful conversations.

1. Sales Fundamentals Never Go Out of Style

 Tim kicked things off by emphasizing the importance of sticking to basics. 

From having a clear prospecting list to refining your follow-up approach, success in sales comes from doing the simple things consistently—and doing them well.

2. Your Sales Story Needs a Makeover

 Forget the "me, me, me" pitches. Tim laid out a five-part framework for creating sales stories that resonate with your specific buyer. 

This includes understanding their role, desired outcomes, challenges, emotional drivers, and how your solution uniquely helps.

3. Follow-Up that Doesn’t Annoy

 Checking in with “just touching base” is a surefire way to get ignored. Tim advocated for follow-ups that provide insight, spark curiosity, and deliver value turning your name into something prospects look forward to seeing in their inbox.

4. Plan and Block or Bust

 Top performers don’t “wing it.” They plan their week in advance, time block their days and protect space for proactive selling. 

Tim recommends structuring your time into three two-hour focus blocks to maintain momentum and pipeline health.

5. Be a Sponge and Stay Curious

 Success favors those who constantly learn and adapt. Tim encouraged sales pros to watch others, ask questions, and stay hungry for improvement. 

Listening and curiosity, he says, are still the most underrated skills in sales.

This episode was a masterclass in sustainable sales. Tim’s refreshing take? Success isn't about chasing the newest trend; it’s about mastering what works and doing it better than anyone else. In a world chasing hacks, discipline is your edge.

Don't miss out, your next big idea could be just one episode away!

This Show is sponsored by Fist Bump
Your prospecting partner to authentically fill your pipeline with ideal customers.

Check out our Live Show Events here: Mastering Modern Selling Live Show

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In this powerful episode of Mastering Modern Selling, co-host Tom Burton sits down with Carson Heady to explore his latest book The Show Must Go On. 

This isn’t just a typical sales book—it’s a deeply personal, tactical, and tested playbook from one of the top voices in modern sales. 

The episode unpacks Carson’s journey from early setbacks to building a repeatable sales model that’s generated over a billion dollars in revenue—primarily through LinkedIn.

Whether you're navigating complex sales environments or looking for new energy in your approach, this episode delivers strategy, mindset, and inspiration in equal measure.

1. LinkedIn as a Relationship Engine

 Carson credits LinkedIn for over $1 billion in influenced sales, calling it the "largest coffee shop in the world." 

He shared his exact prospecting rhythm: high-quality outreach, consistent engagement, and reactive messaging based on real-time customer signals.

2. Your Network Is Your Net Worth

 After applying for 1,600 jobs during a tough career moment, Carson realized the critical importance of personal branding and networking. 

That journey fueled his investment in content creation and community-building across platforms, growing his reach to over 300,000 followers.

3. Embrace the Voices in Your Head

 Drawing from personal stories—like being cut from his high school basketball team—Carson discussed using negative feedback as fuel. 

"Who's in your head?" isn’t just a chapter in his book; it's a mindset of resilience and continuous improvement.

4. Your Superpower Isn’t Just a Buzzword

 Identifying and maximizing your superpower (Carson's is orchestrating value for others) is key to creating lasting customer impact. 

He encouraged listeners to understand their own strengths and those of their colleagues to build winning teams.

5. The Show Must Go On

 Inspired by Queen’s iconic lyrics, the book—and Carson’s philosophy—champions perseverance in the face of personal and professional adversity. 

It’s about delivering your best, even when life is at its toughest.

This episode is more than a discussion—it’s a masterclass in navigating modern sales with intention and authenticity. Carson’s story is a reminder that success is a mix of mindset, method, and meaning. 

Whether you’re rebuilding a network, refining your process, or redefining your "why," this conversation will push you to show up stronger and stay in the game.

Want the playbook that’s helped generate over a billion in revenue? Pick up Carson’s The Show Must Go On and discover the tactics, mindset, and stories behind modern sales mastery.

Don't miss out, your next big idea could be just one episode away!

This Show is sponsored by Fist Bump
Your prospecting partner to authentically fill your pipeline with ideal customers.

Check out our Live Show Events here: Mastering Modern Selling Live Show

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In this episode of Mastering Modern Selling, Tim FitzGerald joins the team to discuss key strategies for early-stage companies, particularly around navigating sales during the startup phase. 

With decades of experience in software sales, Tim offers his expertise on how founders can streamline sales efforts, make strategic decisions, and avoid common pitfalls when scaling their businesses.

• Sales as a CEO's Responsibility: 

Tim shares that in early-stage companies, founders often handle sales themselves, which can lead to burnout. 

Tim's role as a Fractional Chief Revenue Officer (CRO) helps these CEOs structure their sales processes and offload the responsibility, allowing them to focus on other critical aspects of their business.

• Targeting Early Adopters: 

One of the biggest challenges for startups is identifying the right early adopters those customers who are willing to take a risk on a new product. 

Tim emphasizes the importance of speaking to visionaries who are not only open to new technologies but are also eager to be part of something groundbreaking.

• The Power of Network-Driven Sales: 

Founders often start by tapping into their personal network. This “ground game” involves cold outreach, building relationships, and leveraging referrals. 

While cold calling isn’t glamorous, it remains an essential tool for early-stage sales​.

• Building a Sales Playbook: 

Tim discusses the importance of developing a sales playbook that captures the founder’s insights and strategies. 

As startups grow, it’s critical to document the methods that have worked so that new salespeople can follow a structured approach, ensuring consistency and scalability.

• The Role of Founder-Led Content: 

One of the most effective ways for early-stage companies to gain visibility and trust is through founder-led content. 

Tim highlights how platforms like LinkedIn allow founders to share their journey and thought leadership, which not only attracts early adopters but also builds credibility in the market.

The key to successful sales in early-stage companies is a balance between passion, strategy, and structure. Founders must leverage their networks, develop a repeatable sales process, and embrace their role as content creators. 

By focusing on the right customers, documenting sales strategies, and staying committed to continual improvement, founders can pave the way for growth and success. 

Tim's insights are a powerful reminder that, while the startup journey is challenging, it's also filled with opportunity for those willing to innovate and adapt.

Don't miss out, your next big idea could be just one episode away!

This Show is sponsored by Fist Bump
Your prospecting partner to authentically fill your pipeline with ideal customers.

Check out our Live Show Events here: Mastering Modern Selling Live Show

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In this episode of Mastering Modern Selling, the hosts welcome Brian Doyle, CEO of Holden Advisors, to discuss the critical role of pricing and negotiation in B2B sales. 

With a background as an Air Force pilot and extensive experience in sales leadership, Brian provides a strategic framework for setting the right price, understanding value, and negotiating effectively.

Many salespeople struggle with articulating value and justifying price, often defaulting to discounting instead of defending their worth. 

Brian breaks down how businesses can maximize profitability without losing customers, and how understanding pricing power is essential for long-term success.

1. Pricing Strategy Starts with Value

• Companies must first understand their own value proposition before setting a price.
• Three key value drivers: 
  • Increase customer revenue
  • Reduce customer costs
  • Minimize customer risk
• If businesses can quantify these benefits, they can charge appropriately without unnecessary discounting.

2. Price Increases Can Double Profitability

• Many companies underprice their offerings without realizing it.
• Brian shared a case study where a company raised its prices by 50%, resulting in $80 million in new revenue—without losing a single customer.
• The key to successful price increases is demonstrating value in a way customers understand.

3. Customer Conversations Are the Foundation of Pricing

• Businesses often rely on internal assumptions or biased sales feedback rather than talking directly to customers.
• Brian’s method involves interviewing both current and lost customers to uncover true pricing potential.
• Customers frequently reveal they are willing to pay more when the value is properly articulated.

4. Negotiation is About Framing, Not Discounting

• Sales teams should shift from a price-first conversation to a value-based discussion.
• Timing matters: The best time to discuss pricing is early in the buyer’s journey, not when an RFP is issued.
• Instead of immediately discounting, salespeople should anchor the conversation on ROI and competitive advantage.

5. The Danger of Cost-Plus Pricing

• Many companies default to "cost-plus" pricing (cost + a percentage markup), which limits profitability.
• Instead, businesses should align pricing with perceived and real value.
• Brian suggests segmenting customers: some segments may tolerate price increases better than others, and companies should avoid “one-size-fits-all” pricing.

Brian Doyle’s insights highlight that pricing and negotiation are not about undercutting competitors but about understanding value, strategic positioning, and customer perception. 

His approach provides a structured methodology for increasing pricing power without alienating customers.

Don't miss out, your next big idea could be just one episode away!

This Show is sponsored by Fist Bump
Your prospecting partner to authentically fill your pipeline with ideal customers.

Check out our Live Show Events here: Mastering Modern Selling Live Show

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In this episode of Mastering Modern Selling, hosts Brandon Lee and Carson Heady are joined by special guest Anthony Iannarino to explore how to successfully navigate the changing B2B sales landscape. 

They discuss why traditional outreach methods are failing, how buyers' expectations have shifted, and what sales professionals must do to build real connections that drive results.

1. The Evolution of the Buyer’s Journey

• Buyers no longer rely on salespeople for information; they are well-researched before engaging.
• Salespeople must focus on building unique relationships and offering value that cannot be easily found online.

2. Why Cold Outreach is Becoming Ineffective

• Traditional cold calls and mass email outreach are becoming less effective because buyers are overwhelmed with unsolicited messages.
• Instead of pitch-based messaging, sales professionals should prioritize relationship-building through social selling and thought leadership.

3. The Power of Personal Branding and Social Selling

• Posting relevant content and engaging on LinkedIn can help salespeople build credibility and stay top of mind with prospects.
• A well-placed social media post, personal story, or insightful comment can open doors that traditional cold outreach cannot.

4. Creating Strategic Value in Sales Conversations

• The best salespeople create value by deeply understanding the buyer’s business and offering insights, rather than focusing on their own company’s strengths.
• The "Four Levels of Value in Sales" framework suggests that sellers should move beyond product features and focus on delivering strategic outcomes.

5. How to Crack the Code of Modern B2B Sales

• Stop Selling, Start Helping: Salespeople should focus on facilitating the buyer’s decision-making process rather than forcing a sale.
• Introduce and Connect Decision-Makers: Providing introductions to key players within and outside the buyer’s industry builds trust and influence.
• Use Insights to Guide Buyers: Rather than pitching, sales professionals should bring valuable insights to the table, showing buyers what they might be missing.
• Adapt to Buyer Behavior: By leveraging social selling, community engagement, and digital platforms, salespeople can meet buyers where they are rather than forcing outdated outreach methods.

The key to modern B2B sales lies in adapting to the way buyers make decisions today. The old-school approach of persistent cold calling and aggressive pitching is losing its effectiveness. 

Instead, success comes from creating meaningful connections, understanding what truly matters to buyers, and positioning oneself as a valuable resource. 

By focusing on trust, insights, and strategic collaboration, sales professionals can crack the code of modern selling and build long-term relationships that drive real business success.

Don't miss out, your next big idea could be just one episode away!

This Show is sponsored by Fist Bump
Your prospecting partner to authentically fill your pipeline with ideal customers.

Check out our Live Show Events here: Mastering Modern Selling Live Show

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In this episode of Mastering Modern Selling, hosts Carson and Tom dive deep with James Buckley, host of the Sell Better daily sales show. 

James shares how going live every day transformed the way sales professionals learn, engage, and sell in today’s fast-paced digital world. 

He walks through his journey, the shift from traditional selling to content-driven engagement, and how sales teams can stay ahead by becoming practitioners—actively doing what they teach.

1. Consistency Builds Authority & Trust

James and his team went from occasional webinars to a daily sales show, proving that consistent content drives engagement and credibility. The show started small but quickly became a go-to resource for sales professionals.

Lesson: Showing up regularly (whether through content, calls, or engagement) makes you a trusted expert in your field.

2. Stop Chasing—Create Demand Instead

James emphasizes that salespeople should provide value first, rather than immediately trying to sell. 

By sharing insights, helping others, and engaging meaningfully, potential buyers naturally come to you when they need your solution.

Lesson: Be the person buyers come to for guidance, instead of always chasing cold leads.

3. The Phone Is Hot Again

With inboxes flooded with AI-generated emails, James points out that the phone has made a comeback as an effective sales tool. 

He still makes cold calls and actively demonstrates outreach techniques, proving that direct human connection still wins.

Lesson: Use modern tools, but don’t ignore proven sales tactics like personalized calls and relationship-building.

4. Sales Is More Than Just Closing Deals

James describes modern selling as more than just making sales—it’s about being a valuable resource, mastering time and task management, and adapting quickly. 

His structured calendar and disciplined workflow ensure he balances live shows, sales, and engagement without burnout.

Lesson: If you manage your time right, you can sell effectively while also creating content and engaging with your audience.

5. Face Your Fears & Keep Testing

One of the biggest lessons James learned is that fear holds many sellers back—whether it's making cold calls, appearing on video, or trying new strategies. He encourages sales pros to test new approaches constantly and embrace change.

Lesson: Get uncomfortable, experiment with new sales methods, and always be learning from the results.

 James Buckley proves that modern selling isn’t just about transactions—it’s about transformation. By going live daily, staying close to his audience, and constantly refining his approach, he’s built a community that trusts him. 

His advice? Stay consistent, provide real value, and never stop learning.

Don't miss out, your next big idea could be just one episode away!

This Show is sponsored by Fist Bump
Your prospecting partner to authentically fill your pipeline with ideal customers.

Check out our Live Show Events here: Mastering Modern Selling Live Show

Subscribe to our Newsletter: Mastering Modern Selling Newsletter

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In this episode of Mastering Modern Selling, Brandon Lee, Carson Heady, and Tom Burton discuss the importance of the Digital CEO—a modern-day executive who actively engages on LinkedIn and other digital platforms to build trust, credibility, and relationships. 

The conversation dives into why today's CEOs can no longer afford to remain invisible and why being digitally present is a core job responsibility for leaders in 2025 and beyond.

1. The CEO as a Brand Evangelist

• A CEO’s presence on LinkedIn is not about self-promotion, but about showcasing company culture, vision, and values.
• Companies with digitally active CEOs are viewed as more trustworthy and attract better talent and clients.

2. LinkedIn Is a Business Necessity, Not an Option

• LinkedIn is no longer just for job seekers—it’s the world’s leading business networking platform.
• CEOs and other C-suite executives who fail to engage digitally risk losing relevance and missing key relationship-building opportunities.
• The organic reach on LinkedIn is still strong compared to other platforms where paid advertising dominates.

3. What Should a CEO Be Posting?

• CEOs should not just talk about themselves or their company’s products.
• Instead, they should share:
  • Industry insights and observations
  • Company culture, successes, and behind-the-scenes moments
  • Engaging stories about customers, employees, and the journey of leadership
• Regular, authentic content builds a CEO’s credibility and strengthens their company’s brand.

4. The Time & Resource Commitment for CEOs

• Many CEOs resist social media due to time constraints, but a strong strategy can be executed in under an hour a week.
• Options include:
  • Hosting a live show or podcast to generate content effortlessly
  • Engaging briefly but meaningfully with followers and industry discussions.
• The investment in time and resources is minimal compared to the return in brand trust, sales opportunities, and talent attraction.

5. Shouldn’t Marketing Handle This?

• Marketing plays a critical role, but nothing replaces the credibility of a CEO’s personal voice.
• The best approach is a collaboration—CEOs share their thoughts, and marketing amplifies them through various channels.
• Live shows, interviews, and consistent engagement make content creation easy without requiring extensive preparation.

The conversation makes it clear: in 2025, a CEO’s digital presence is non-negotiable. Being active on LinkedIn and other platforms is not just about marketing, it’s about leadership, credibility, and visibility in the modern business world. 

Companies whose executives embrace this shift will have stronger brands, better talent pipelines, and more engaged customers.

Don't miss out, your next big idea could be just one episode away!

This Show is sponsored by Fist Bump
Your prospecting partner to authentically fill your pipeline with ideal customers.

Check out our Live Show Events here: Mastering Modern Selling Live Show

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