Art & Science of Complex Sales

Sales Leadership, Playbooks, and Account Growth | Des McCluskey

Join us as we explore the complexities of B2B sales with Des McCluskey, Managing Partner of Padeda and former Sales Director at Johnson & Johnson. Des shares practical insights on building effective sales playbooks, the critical role of first-line sales leaders, and navigating complex sales cycles. Drawing from experience in medical devices, professional services, and financial services, he provides actionable strategies on sales enablement, coaching, and account management that sales leaders can apply immediately.

The Cultural Gap in Sales Playbooks (6:09)

Des highlights a fundamental difference between American and European sales approaches. While U.S. teams embrace structured sales playbooks, modeled after football plays, European teams favor a more flexible, improvisational style inspired by soccer. This cultural contrast makes implementing playbooks a challenge in Europe, requiring a shift in mindset and execution.

The Rise of Bureaucracy in Sales Processes (14:10)

Des discusses how an increase in technical buying influences and complex procurement systems is slowing down deal closures. Even with verbal approval from decision-makers, deals are now delayed by an average of six weeks due to finance checks and system inefficiencies. This trend creates forecasting challenges for sales teams, emphasizing the need for more proactive post-approval management.

The Power of Retention Squads (23:35)

Des introduces “retention squads”—cross-functional teams dedicated to managing and growing existing accounts. Unlike traditional account management, these agile, project-based teams engage multiple stakeholders to maximize renewals and drive account expansion. By fostering deeper relationships and broader outreach, retention squads help organizations secure long-term growth and uncover new opportunities.

 

Breaking Stereotypes in Sales | Leslie Venetz

In this episode, Leslie Venetz founder of The Sales-Led GTM Agency joins us for a captivating discussion on her journey into the sales profession and her pivotal role in the Women Sales Experts Conference. Once viewing sales as merely a temporary gig, Leslie discovered her true passion when she embraced her ability to help people solve their problems.

The Soul-Sucking Impact of Bad Data (10:04)

Leslie discusses one of the biggest challenges sales teams face—poor data quality. She explains how bad data demoralizes sales reps, turning outreach into a frustrating and ineffective process. Leslie emphasizes that having accurate, enriched data combined with the right tech stack not only improves outreach success rates but also alleviates the mental fatigue caused by ineffective efforts.

The Power of Signals in Sales Tech (14:04)

Leslie highlights how modern sales tech has transformed outreach by leveraging signals—indicators like new hires, financial shifts, or market events. She explains that the true power lies in connecting these signals to build timely, relevant, and personalized outreach. By integrating these insights, sales teams can craft pitches that resonate with prospects' current challenges and priorities, making outreach significantly more effective.

Discovery Meetings: The Final Step of Top-of-Funnel (30:11)

Challenging a common misconception, Leslie argues that discovery meetings should be seen as the last step of top-of-funnel, not mid-funnel. She explains that this stage is where sales reps earn the right to advance conversations by actively listening and understanding prospects' needs. Leslie criticizes the practice of turning discovery meetings into box-ticking exercises, emphasizing that meaningful dialogue is what truly qualifies prospects for the next step.

Navigating Sales | Mario M. Martinez Jr.

Join us in this episode with Mario Martinez Jr., whose journey started unexpectedly at a photo lab and soared to leading digital sales prospecting training. Mario's story is not just about achieving success but about redefining it. From grappling with financial hurdles to purchasing his first home at age 21, Mario's experiences demonstrate the power of tenacity, strategic thinking, and the art of helping others in sales. Listen to how a crucial mentoring moment with Hunter Anderson changed his life and philosophy forever, proving that sometimes a setback is just a setup for a breakthrough.

Elevating Sales Performance Through Intentional Development (12:51)

Great sales leaders understand that coaching is the key to driving performance and long-term success. While many organizations focus on coaching their teams, the best sales managers consistently develop their people, helping them refine their skills and improve results. Mario shares how early in his career, he identified gaps in his own abilities and made the decision to invest in sales training—a move that later shaped his success and positioned his company, Vengreso, as a global leader in sales prospecting training. He emphasizes that today’s sales landscape demands an omnichannel approach, combining email, voice, LinkedIn, video, and live events to effectively engage buyers. By prioritizing coaching and continuous learning, sales leaders can equip their teams with the tools and strategies needed to succeed in an evolving digital-first world.

The Decline of Traditional Outreach: Why Omnichannel is the Future (21:54)

Cold outreach methods like email and phone calls are becoming increasingly ineffective, with engagement rates plummeting. Mario shares his frustration with industry standards, where a mere 1% engagement rate on emails is now considered a success. With email volume skyrocketing and platforms like Google and Microsoft cracking down on deliverability, sales teams must rethink how they engage prospects. The key to breaking through the noise lies in an omnichannel approach—combining email, voice, LinkedIn, video, text, and live events to create multiple touchpoints. But personalization must go beyond basic AI-driven details like a prospect’s location or alma mater. Instead, outreach should be genuinely hyper-personalized, delivering real value and meaningful connections that stand out in an oversaturated digital world.

The Power of Referrals (27:05)

Many sales teams overlook one of the most powerful tools in prospecting—referrals. Mario emphasizes that 84% of buyers begin their purchasing journey through a referral, yet most sales cadences fail to prioritize this step. Instead of starting with cold outreach, the first move should be identifying mutual connections and leveraging introductions to create warm conversations. He explains how following prospects on LinkedIn is a crucial yet underutilized step, as it guarantees visibility without being blocked by spam filters. Additionally, optimizing LinkedIn profiles to focus on who you help and the problems you solve—rather than just sales achievements—creates a stronger first impression. By making referrals the foundation of a sales cadence, sales teams can dramatically improve engagement rates and secure more meetings with less effort.

From Chaos to Clarity: Building Better Sales Teams | Liz Heiman

What if you could transform a chaotic sales environment into a well-oiled machine? Join us for an enlightening conversation with Liz Heiman, CEO and Chief Sales Strategist of Regarding Sales. With her extensive knowledge in strategic selling, Liz shares her insights on creating scalable, manageable, and predictable sales infrastructures. She also shares how leaders can align company vision and values with strategic frameworks to eliminate chaos and foster a thriving sales team environment in this episode.

 

Building a Sales Strategy That Drives Purpose and Results (8:20)

The first step to eliminating chaos in a sales organization is establishing a clear strategy. Without a guiding plan, sales activities become aimless, leading to inefficiency and misalignment. A strong strategy starts with defining the company’s vision, values, and mission—ensuring everyone understands the direction and expected behaviors. Sales goals alone aren’t enough; they must be supported by context that clarifies priority clients, key products, and target sectors. By providing this strategic foundation, leaders empower their teams to make informed decisions that align with the company’s long-term objectives rather than just chasing quick wins.

Crafting the Right Message for the Right Audience (12:42)

Having a well-defined messaging strategy and ideal customer profile (ICP) in driving effective sales conversations is important. Many organizations believe they understand their ICP but often lack the depth needed to connect with all the decision-makers involved in complex B2B sales. Customers care more about how a product solves their problems than the product itself. Effective messaging must speak directly to each stakeholder’s relationship to the problem, using language that resonates with their concerns. Companies that align their strategy, goals, messaging, and sales process can achieve remarkable growth—whether aiming for consistent, predictable increases or dramatic year-over-year expansion. The key lies in developing clear messaging that prompts potential clients to think, "Can you do that for me?" rather than overwhelming them with product features.

Managing Sales Teams Through Funnel Metrics (20:02)

Accountability in sales leadership is crucial for effective team management, with a deep understanding of the sales funnel playing a central role. With only 40% of U.S. sales reps meeting their quota, the root causes often lie in the absence of strategy, inadequate systems, poor management, or hiring missteps. True accountability starts with mastering key funnel metrics—volume, velocity, and conversion ratios—at every stage of the sales process. Sales leaders must shift their focus from short-term closings to regularly analyzing the entire funnel, enabling teams to meet goals not just for the current month but for the next 3, 6, and 12 months. By managing the funnel rather than focusing solely on final outcomes, leaders can uncover bottlenecks, improve forecasting, and drive sustained success.

Sales Trends and Strategies for 2025 | Mike Stokes

In today's episode of The Art & Science of Complex Sales, we're thrilled to welcome Mike Stokes the Founder of Indicator. With a strong connection to sales leaders in New Zealand and Australia, Mike will share insights from the 10th annual Mood of the Sales Leader Survey, offering practical advice and real-world examples to navigate economic shifts and technological advancements. Don't miss this opportunity to learn how to harness current trends to elevate your team's performance.

Mood of the Sales Leader Survey (1:40)

Indicator, led by CEO Mike Stokes, is a sales development firm that has spent the past decade facilitating sales leadership groups across New Zealand and Australia, gathering firsthand insights into market trends. This effort led to the Mood of the Sales Leader Survey, now in its 10th year, offering a comprehensive look at industry challenges. The 2024 survey revealed that last year was the toughest sales environment seen in years, with economic slowdowns, rising costs, and declining revenue growth impacting sales teams. One of the most striking insights was a dramatic shift in salesperson motivation—remuneration and incentives became a top priority due to stagnant salaries and rising living costs. As companies struggle to balance financial constraints with retention strategies, sales leaders must navigate an increasingly complex landscape to support and motivate their teams.

Reigniting Growth - The Future of Sales Development (15:28)

As 2025 begins, business confidence is gradually improving, with companies seeing a light at the end of the tunnel despite lingering economic challenges. While small and medium-sized businesses pulled back on training investments last year, they are now beginning to reinvest, driven by optimism and a need to prepare for future growth. Sales leaders are particularly focused on AI and technology, as well as coaching, yet many still underinvest in their own development. Despite AI adoption among salespeople rising significantly, overall company investment in sales technology remains slow. With growing confidence, businesses are shifting their attention back to refining their processes and structures to build momentum for the year ahead.

Technology in Sales (21:30)

AI and emerging technologies have created a technology confusion gap, where companies struggle to implement and optimize existing tools while trying to keep up with new advancements. Many businesses still underutilize foundational systems like CRM, missing valuable opportunities. The key, as Mike Stokes emphasizes, is to first define sales processes and objectives before layering on technology. While AI adoption is accelerating, companies risk chasing trends without strategic implementation. The real opportunity lies in using technology as an enabler—focusing on what truly adds value rather than being swept up in the hype.

Crafting Authentic Relationships in Sales | Brynne Tillman

Ever wondered how to navigate the declining efficacy of traditional methods in the sales world? Brynne Tillman, CEO of Social Sales Link shares her strategies, honed over 15 years of leveraging LinkedIn, to build authentic, relationship-driven networks. Her insights promise to reshape your perspective on digital selling by aligning advanced technology with genuine human interaction.

From Cold Calls to AI (3:43)

Sales professionals today face a major shift as traditional methods like cold calling and inbound referrals become less effective. Many struggle to secure the first conversation with prospects who no longer answer unknown calls. Brynne emphasizes LinkedIn and AI as key tools for overcoming this challenge—LinkedIn enables trust-based social selling, while AI helps create authentic, targeted messaging. Having once relied on strategic introductions rather than cold calls, she now teaches salespeople to adapt by leveraging these modern tools to build credibility, engage prospects, and start meaningful conversations.

Authentic Selling on LinkedIn (7:56)

Brynne emphasizes the importance of leveraging LinkedIn for trust-based relationship-building rather than transactional sales. She advocates for three key mindset shifts: detaching from a prospect’s monetary value and focusing on the value you bring, treating online interactions like real-life conversations, and slowing down outreach to build genuine connections. Instead of using a "connect and pitch" approach, sales professionals should engage prospects through meaningful conversations and relevant content, ultimately leading to stronger relationships and better sales outcomes.

Leveraging AI for Sales Conversations (18:08)

While AI promises speed and efficiency, Brynne highlights the challenge of maintaining authenticity and personalization in sales. Early AI tools were flawed—generating misleading content, citing competitors, and lacking a structured approach. To address this, her team built a platform that organizes prompts, tailors messaging to different clients, and enforces brand-specific guidelines. She introduces the CRISP+ model for effective AI prompts: Context, Role, Inspiration, Scope, Prohibitions, and the key addition—asking AI to clarify uncertainties before generating responses. This structured approach helps sales teams harness AI responsibly, ensuring consistency, compliance, and genuine engagement.

B2B Sales Strategies for 2025 and Beyond | Matt Green

In the fast-paced world of tech sales, staying ahead of the curve is crucial. As we step into 2025, sales strategies are being reshaped by shifting economic conditions, expanding buying committees, and the integration of new technologies. In the latest episode of our podcast, we dive deep into these changes with Matt Green, CRO and co-founder of Sales Assembly, to uncover the essential skills and strategies that sales professionals need to thrive in this evolving landscape.

Join us as we explore the transformation of sales tactics, where old meets new in dynamic ways. From creative cold call openers to the resurgence of physical outreach like gifting, businesses are finding innovative methods to rise above the digital noise. We emphasize the value of in-person interactions in moving sales forward and the importance of setting clear expectations for sales teams at events. Matt also shares the journey of co-founding Sales Assembly, filling a gap in resources for tech sales leaders. Experience how their platform has enabled sales teams to receive practical, applicable training from industry experts, setting a new standard in sales excellence.

 

(00:04:10) - Frontline Sales Skills and Trends 

This chapter brings listeners into the world of complex sales with insights from Matt Green, the Chief Revenue Officer and co-founder of Sales Assembly. We explore the critical skills that sales teams need today, focusing on multi-threading and storytelling as essential competencies in the evolving tech sales landscape. With buying committees growing and budgets tightening, the ability to navigate enterprise sales motions is more crucial than ever. Additionally, the importance of storytelling is highlighted, not just in sales but also in post-sales environments, as organizations reevaluate their customer success teams. Through Matt's experience and the knowledge shared among hundreds of CROs and VPs of sales in Sales Assembly's community, we uncover the trends and challenges shaping the future of B2B sales

 

(00:10:50) - Navigating Shifts in Sales Tactics

This chapter explores the evolution of cold call openings, highlighting how techniques have shifted from traditional permission-based openers to more varied and creative approaches. We discuss the effectiveness of different tactics, such as directly pitching or using humorous openers, and how companies are customizing their strategies to suit their needs. We also touch on the resurgence of physical outreach, like gifting, as a way to break through digital noise and make meaningful connections. Additionally, the importance of in-person interactions is emphasized, particularly in advancing the sales cycle and qualifying opportunities. Overall, this chapter sheds light on the blending of old and new methods in sales outreach to achieve better engagement and results.

 

(00:18:55) - Building Sales Community and Networking

This chapter focuses on the importance of setting clear expectations for sales teams at conferences and events to maximize engagement and networking opportunities. We highlight how simple guidelines can enhance the effectiveness of salespeople, moving beyond mere training. Additionally, we explore the origin story of Sales Assembly, founded by Matt and his partner Jeff, who identified a gap in community and training resources for sales leaders in the tech industry. The chapter shares insights into how Sales Assembly has grown over the past eight years by leveraging an ecosystem of B2B tech companies to provide relevant, live training sessions. We emphasize the value of bringing in experienced sales professionals to lead these sessions, ensuring that the content is both practical and directly applicable to the challenges faced by sales teams today.

Navigating MSP Growth | Ian Richardson

Join us for an insightful conversation with Ian Richardson, co-founder and CEO of Fox and Crow Group and MSPSalesProcess.com, as he explores the world of Managed Service Providers (MSPs) in 2025. With nearly 45,000 MSPs nationwide, Ian shares his expert advice on overcoming sales barriers and attracting top talent in the industry.

From transforming technical expertise into a solid sales strategy to driving customer-focused growth, Ian offers actionable insights to help MSP founders thrive in an ever-evolving and competitive market.

 

Challenges in the MSP Industry (3:04)

 

Ian discusses the challenges MSPs face with their sales pipeline, including the intangibility of IT services, customer churn, and the lack of outbound sales efforts. He explains that many MSPs struggle because they are founded by technical experts without formal business or sales training. This often leads to difficulties in hiring sales talent, a fear of phone outreach, and a lack of structured marketing campaigns. Additionally, the commoditization of IT services and the absence of differentiation make it harder for MSPs to stand out in a competitive market.

Sales Process and Differentiation in MSPs (15:35)

While MSPs excel at technical processes, they often struggle with adopting a structured sales process due to negative perceptions of sales. Ian Richardson highlights how the word "sales" can create resistance among MSP leaders, who tend to see themselves more as engineers than entrepreneurs.

He explains that smaller MSPs (below $2M in revenue) often avoid formal sales discussions, while more mature MSPs ($3M+ in revenue) begin recognizing and addressing gaps in lead generation, marketing, and messaging. Ian stresses that having a clear process is essential for scaling an MSP business, especially since fixed-fee agreements depend on operational efficiency.

With 45,000 MSPs in North America and only 8,000 surpassing $2M in revenue, Ian emphasizes that success comes from taking ownership of the sales process—whether explicitly labeled as "sales" or not.

Differentiation Strategies and Hiring Processes (22:38)

Ian underscores the importance of differentiation for MSPs, suggesting that specializing in specific industries, such as healthcare, can help MSPs leverage industry knowledge to build stronger client relationships. He also recommends flipping traditional service models, such as placing technicians onsite, to create a more personalized experience and reduce churn. Additionally, targeting underserved markets or clients that others overlook can provide a competitive edge.

Ultimately, Ian stresses that combining these differentiation strategies with a solid sales process, effective hiring practices, and outbound marketing is key to driving growth and long-term success.