Art & Science of Complex Sales

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.

 

Building Winning Sales Teams for the Future with Two Tall Guys

Do you know the key strategies that effective CEOs use to empower their sales teams for success? Join us with guests Sean O'Shaughnessey CEO of New Sales Expert and Kevin Lawson, President of Lighthouse Sales Advisors as we explore the victories and challenges facing sales teams as we head into 2025. In this episode, we highlight the essential actions leaders must take, such as defining ideal customer profiles and crafting compelling value propositions, to navigate the complexities of the sales funnel and build a winning team.

Data-Driven Sales Leadership for Growth (13:28)

This chapter focuses on the importance of data-driven decision-making for CEOs and their sales teams. We explore how understanding core data, such as call volume, customer life cycle, and attrition rates, can guide strategic decisions. By analyzing customer behavior and demographics, companies can refine their ideal customer profiles and improve sales and marketing strategies. Additionally, the chapter highlights the evolving nature of a CEO's dashboard, emphasizing that the key metrics should adapt annually to address the most pressing challenges. We also touch on the necessity for CEOs to anticipate external factors, such as geopolitical events, and to communicate effectively with their teams to maintain alignment and focus on resolving the current top priorities.

 

Driving Sales Team Improvement Through Coaching (24:01)

This chapter explores the importance of incremental improvement in sales teams and the power of coaching to achieve these gains. We discuss the value of gradually enhancing the performance of salespeople by focusing on skills development, rather than just pushing for more calls or deals. By emphasizing coaching and personal growth, sales leaders can transform C-level performers into C plus or B-level, and motivate B's to aim for A-level performance. Using sports analogies, we highlight how small improvements, like gaining an extra yard in football or an additional hit in baseball, can lead to significant successes. Additionally, we touch on the need for structured coaching plans, supported by resources available on our websites, to effectively assess and elevate team capabilities.

 

Sales Process and Coaching Strategies (29:16)

This chapter explores the importance of understanding the varied strengths within a sales team and how structuring a coaching plan around these can lead to improved sales performance. We discuss the significance of assessing product fit, probability, and ideal customer profile before classifying a lead, likening this to the crucial addition of salt in cooking. We highlight how small adjustments in key sales metrics—such as a 7% improvement in sales projects created, win rate, average deal size, and a reduction in sales cycle time—can potentially double revenue. Sean and Kevin emphasize focusing on customer success and establishing a repeatable sales process as essential strategies for a successful 2025. 

From Entry-Level to Industry Leader │ Andrew Barbuto

Ever wondered how a career in digital media sales can transition from an entry-level position to an industry-leading role? Meet Andrew Barbuto, a digital media sales expert and Author of "Top Sales Producer: How To Crush Your Sales Quota", who shares his intriguing journey from the trenches of budget management and report generation to becoming a top-performing sales producer. His initial hands-on experience as an account manager played a crucial role in understanding complex sales and educating clients, laying a robust foundation for his remarkable success.

Complexity of Sales in Digital Media (5:16)

In the digital media industry, sales are inherently complex, and this complexity is highlighted when comparing managed services sales with software sales. Managed services involve full-service campaign management, while software sales require onboarding, change management, and long-term client support. Mastering industry-specific knowledge, managing multiple stakeholders, and building lasting relationships are all key to addressing these challenges effectively. Moreover, staying engaged with clients post-sale is essential for maintaining trust and satisfaction, even after transitioning them to an onboarding team. This approach underscores the importance of adaptability and commitment in navigating the complexities of digital media sales.

Maintaining Balance (14:29)

Balancing an active sales career with the responsibility of writing a book to help others succeed presents significant challenges. Despite the demanding nature of his work, Andrew dedicates early mornings, late nights, and occasional all-nighters to refine his approach. Writing the book required him to step back and analyze his methods, transforming his practices into a clear, step-by-step process. This experience not only deepened his own understanding of sales but also provided a structured framework that others can adopt to achieve lasting success.

Setting Up for Success (23:31)

Setting up for success in sales involves several key components. First, selling a product that you truly believe in is essential, as it ensures long-term client satisfaction. Andrew also emphasizes the need for strong support, including a skilled team that manages day-to-day operations and resources that free up the salesperson’s time. Another crucial factor is company culture and support. Having the flexibility to work with clients in non-standard situations can make a significant difference. By focusing on customer-centric values and leveraging organizational support, Andrew demonstrates how the right environment can empower salespeople to thrive.

 

Future-Proofing Sales for 2025 │ Matt Ferguson

What if the secret to skyrocketing your sales success lies in refining your Ideal Customer Profile (ICP) and optimizing your team structure? Join us as we sit down with Matt Ferguson, Founder of MDF Coaching and Consulting, who shares his invaluable insights on navigating the challenges of complex sales in today's fast-paced world. As 2024 wraps up, Matt highlights the importance of aligning the right people with the right roles, and how an overload of modern sales tools might be hindering rather than helping your process.

Targeting the Right Accounts (0:03)

Matt discusses key sales challenges as we move into 2025. He highlights the importance of aligning talent with tasks and avoiding the mistake of targeting the wrong accounts. A key issue is the lack of a well-defined Ideal Customer Profile (ICP), which leads to wasted time on irrelevant leads. Matt also addresses the paradox of sales tools, noting that more tools often complicate processes. He emphasizes the need to focus on quality over quantity when building sales lists, targeting ideal customers with clear, objective criteria to improve efficiency and conversion rates.

The Balance Between Prospecting and Closing (20:02)

Matt discusses the challenges of maintaining focus and consistency within sales teams. He emphasizes the importance of full-cycle reps who can handle both hunting for new business and closing deals. However, he warns that salespeople often lose their hunting drive once they start closing deals, leading to a decline in pipeline activity. Matt stresses the need for managers to stay engaged with high-performing reps and ensure they remain focused on the right tasks. He also highlights the value of celebrating both meetings booked and revenue closed, as both are essential for long-term success. He draws parallels between sales and sports, explaining that success in both requires discipline, practice, and consistent effort over time.

Mastering Consistency: The Key to Long-Term Sales Success (28:58)

Matt stresses the importance of consistency in sales for achieving long-term success. He highlights that success doesn’t come from drastic changes but from consistently taking small, positive actions every day. Whether it’s booking meetings or closing deals, defining what a successful day or week looks like helps sales reps stay focused. By stacking small wins week by week, sales reps can build momentum, leading to significant results over time.

Adaptive Strategies for Modern Sales Leaders │ Nicole Babel and David Mullins

Explore how personalized sales strategies and why the importance of leveraging individual strengths to engage effectively can help you with Nicole Babel and David Mullins from SalesStar. 

 

With decades of experience, Nicole and David offer invaluable strategies to help sales leaders and teams adapt to rapid changes, such as accelerated decision-making and niche market specialization. This conversation sheds light on the challenges of setting appropriate metrics and KPIs and the benefits of integrating a robust referral strategy to enhance lead generation and foster meaningful conversations in an increasingly noisy world.

 

Effective Sales Strategy Discussions (8:53)

This chapter focuses on the diverse strategies sales professionals can employ to effectively reach and engage their target audience. We explore the importance of identifying personal strengths and preferences, whether it's through networking, social media, or traditional methods like phone calls, and using those strengths to cultivate a community. The discussion highlights the challenge for sales leaders to set appropriate metrics and KPIs in a world where communication styles vary widely. Emphasis is placed on the need for personalized approaches to sales activities, ensuring that each team member leverages their unique skills and passions. The conversation also touches on the increasing difficulty of capturing attention in a noisy world, suggesting that while traditional methods may require more effort, integrating a strong referral strategy can significantly enhance lead generation. Examples include engaging with influential partners or centers of influence who can provide valuable referrals, ultimately moving relationships forward and achieving productive conversations.

 

Target Market Clarity and Messaging (15:58)

This chapter explores the significance of identifying and understanding the ideal client profile and target market in today’s noisy sales environment. We discuss the necessity of having clarity on the target market, the problems being solved for that market, and crafting a compelling message to capture attention. The conversation touches on the challenges salespeople face with the overwhelming amount of noise and the importance of niche marketing. We also emphasize the critical nature of targeting exercises and how they contribute to successful sales strategies. Additionally, we examine the common pushback from sales teams reluctant to turn down deals, stressing the need to focus on projects that align with a company’s strengths. Lastly, the chapter addresses the role of discipline and accountability in sales, questioning whether these traits are diminishing in today’s workforce or if this perception is a myth.

 

The Impact of Sales Leadership (22:01)

This chapter addresses the pivotal role of sales leaders in fostering team success and accountability. We explore how genuine care for a team's growth and understanding individual motivations can lead to a more effective and motivated sales force, regardless of generational differences. By discussing real-world experiences, such as insights from a Vistage presentation and interactions with sales leaders, we emphasize the importance of systems, processes, and coaching to empower sales teams. The conversation highlights that many sales leaders are well-intentioned but lack the framework and resources to coach their teams effectively. Providing these leaders with the right tools and guidance can transform a culture of simple directives into one of supportive leadership, ultimately enhancing team performance.

Navigating Complex Challenges in Sales │ Amy Franko

Join us as we welcome Amy Franko, the Founder of Amy Franko Associates to the show for an insightful discussion on navigating sales challenges across various industries. Amy's impressive journey from her early days at IBM and Lenovo to her current role in entrepreneurship offers a wealth of experience. She shares how her initial positions, surrounded by successful female leaders, shaped her approach to enhancing sales strategies for mid-market organizations, particularly in professional services, technology, and manufacturing.

Essential Skills for B2B Sales Success in Complex Markets (7:56)

Paul and Amy discuss the evolving skill sets required for success in B2B sales, particularly in challenging decision-making environments. Amy emphasizes that resilience is essential, as mindset drives behaviors and results. Tactically, sales professionals need to excel in filling pipelines and identifying opportunities, paired with strong business acumen. The ability to distill complex information into actionable insights for clients is crucial, enabling salespeople to frame problems, pose impactful questions, and offer unique perspectives. Amy highlights the importance of recognizing patterns across industries to streamline this process. She advises focusing on manageable insights for each client and leveraging broader perspectives to add value, acknowledging that sales professionals need not know every detail of a client’s business but should aim to facilitate meaningful, high-impact conversations.

The Role of Coaching and Fundamentals in Modern Sales (18:04)

Paul and Amy discuss the renewed emphasis on foundational skills and coaching in sales. They highlight that perseverance, pipeline building, and business acumen remain essential for sales professionals, while managers must focus on coaching, fostering shared accountability, and mastering the fundamentals. Amy notes that although technology provides numerous tools to support sales, it often adds complexity, making it crucial to identify the "vital few" that drive success. She emphasizes that integrating skills requires more than learning concepts—it demands practical application and coaching. Both agree on the growing global focus on coaching as a critical component in skill development, helping teams apply and internalize what they learn while building stronger relationships and effectiveness in the sales process.

Redefining Accountability in Sales (21:23)

Paul and Amy explore the evolving nature of accountability in sales, emphasizing its shift from hierarchical directives to a collaborative and mutually beneficial practice. Amy highlights the need to personalize accountability based on individual and team dynamics. Sharing her experience with a writing coach, she illustrates how agreed-upon commitments drive progress and productivity. They also touch on generational shifts, and the idea of "non-negotiables"—essential tasks like prospecting that are critical for success. Together, they emphasize the need to balance a supportive accountability culture with firm standards to achieve organizational goals.

The Growing Importance of Face-to-Face Interaction in Sales (27:00)

Paul and Amy talk about the growing importance of face-to-face meetings in sales. Amy explains that in-person meetings are becoming more popular because they offer energy, connection, and better decision-making. She talks about how she balances working from home, coworking spaces, and meeting clients in person to stay motivated and engaged. She also points out the benefits of events like sales conferences, which virtual meetings can’t fully replace. Paul agrees and adds that AI and digital tools can create too much information, making face-to-face meetings a clearer and more productive way to connect. While they both acknowledge that in-person meetings can be expensive, they believe the results make it worth it. Amy also shares how she combines in-person training to build relationships with virtual coaching and AI tools for better efficiency.

Sales in a Digital World │ Anthony Nicks

Ever wondered how to master the balance between automation and personal touch in sales? Join us in this episode with our guest, Anthony Nicks, Founder, CEO at Transformative Sales Systems.

 

Anthony, a pioneer in fractional sales management, shares his journey from a mechanical engineering background to a successful career in sales. He delves into the key challenges faced by CEOs and business leaders as they navigate the ever-changing sales landscape, emphasizing the increasing importance of fractional sales management. Drawing on his expertise, Anthony provides insights into leveraging emerging sales strategies, such as the revival of cold calling, and adapting to shifts in email marketing practices.

Reviving Traditional Prospecting Methods in a Crowded Digital Landscape (5:35)

Anthony and Paul discuss shifts in prospecting strategies as digital communication faces new challenges, with email marketing becoming less effective due to platform changes. They highlight a renewed focus on traditional methods, like cold calling and personalized outreach, which remain effective when approached with consistency and preparation. Social platforms are increasingly crowded, and algorithm changes have made it harder to connect with the right audiences. In response, they note the resurgence of in-person events and creative approaches like snail mail and handwritten notes, which stand out for their personal touch. These methods are helping to foster meaningful connections, even as digital marketing continues to evolve.

Balancing Technology and Human Connection in Sales (13:32)

Paul and Anthony explore the balance between AI-driven efficiency and the need for genuine human connections in sales. While digital tools like automation and chatbots offer growth potential, they often lack the authenticity buyers crave. The rapid adoption of automation during 2020-2021 may have gone too far, prompting a shift back toward interpersonal engagement. They emphasize thoughtful use of digital tools, ensuring automation enhances rather than replaces the personal touch essential for building trust and relationships.

Building and Measuring Effective Sales Processes (23:58)

Paul and Anthony discuss the importance of building structured, collaborative sales processes and avoiding over-measurement. Anthony emphasizes that tailored systems, developed with input from leadership and sales teams, foster ownership and better adoption. Integrating these processes into CRMs with clear steps and KPIs ensures alignment with organizational goals. He warns against overwhelming teams with excessive metrics, advocating instead for focused, goal-driven measurements and personalized KPIs that drive meaningful results. Both highlight the transformative power of effective sales strategies in improving not only professional success but also personal fulfillment for team members.

The Evolving Landscape of Sales Development │ Alan Maguire

Join us as we welcome back Alan Maguire, the Founder/CEO of ESI to discuss the evolving trends in B2B sales, focusing on talent strategy and the nuanced distinction between training and education. Alan sheds light on how organizations are now more than ever investing in commercial talent to navigate the complexities of modern sales environments. 

 

From Training to Talent Strategy (00:22)

Paul Fuller and Alan Maguire discuss the shifting landscape of B2B sales, particularly in SaaS, where companies are moving from high-volume, metrics-driven strategies to a focus on developing sophisticated sales skills. Alan argues that sales should be seen as a profession requiring education, not just training, and highlights the need for organizations to invest in talent development to bridge the gap between skill expectations and real-world capabilities. This shift aims to elevate sales teams and improve long-term performance.

 

Beyond Knowledge to Application (11:45)

Paul Fuller and Alan Maguire discuss the shift from traditional sales training, which focuses on knowledge, to a more comprehensive approach that includes coaching and behavior change. Alan explains that successful salespeople are hired for their ability to think and act strategically, not just for product knowledge. True sales development requires continuous coaching and application in real-world scenarios, not just one-time training. With tighter capital and tougher sales pipelines, organizations must invest in long-term, behavior-focused education to drive performance, similar to the ongoing coaching in other professional fields.

 

Human Skills vs. AI (20:52)

Paul Fuller and Alan Maguire discuss the split in the sales market: one side advocates for long-term investment in skilled salespeople, while the other turns to AI to automate tasks. Alan says that AI can enhance lead generation but can't replace human interaction in complex B2B sales. Salespeople are still needed for personalized engagement and guidance. They also emphasize that investing in employee development reduces turnover and ensures better retention, urging companies to focus on retaining and upskilling existing talent rather than constantly hiring new staff.