Sales Practitioner’s Edge: Bridging the Experiential Divide: Orientation to the Newsletter
With over 100 subscribers in about a week, I wrote this newsletter orientation for anyone who might find it beneficial.
This brief post will orient the subscriber to this newsletter and the ultimate outcomes you can expect as a subscriber.
The Inception of the Newsletter
I have been fortunate to sell in the global enterprise market segment for almost 15 years with both large and small companies. My commitment to professional development and education is intrinsic to my natural born curiosity.
I am humbled by how often the simple fact that success in field selling roles is grounded in our capacity to develop meaningful trust relationships.
Putting empathy aside, practical sales skills are extremely important. Their presence complements our ability to develop deeper relationships, and their absence has the power to stunt them.
That is the inception of this blog.
In B2B sales, success isn’t built solely on theoretical frameworks or mastering sales methodologies. The most valuable skills I’ve developed aren’t rooted in sales training. While knowledge of processes like SPIN Selling, MEDDPPIC, or Challenger Sales is important, practical skills drive results. Too often, we face a gap between theoretical knowledge and real-world execution. This gap—what I call the “Experiential Divide”—represents the disconnect between what’s taught in sales training (methodology) and the experientially acquired skills that impact the complex, unpredictable reality encountered in the field. When I attend training, and someone asks me how it was, I always think about it in the context of how practical my takeaways were. Do I clearly understand how to apply what I learned in the classroom to what I do in the field?
This blog is my effort to help bridge that divide by focusing on practical, actionable sales skills that directly impact our ability to connect with people—both externally with customers and internally with colleagues. The newsletter will focus on experiential skills and real-world insights that help create a tangible impact in the field and offer context for navigating dynamic, unpredictable situations.
For many salespeople, frustration arises from the training-to-skill gap, the disconnect between learning methodologies and effectively applying them in the field. While training provides a strong foundation, true mastery emerges from practical experience—often through trial and error. I aim to provide subscribers with tools to close this gap and cultivate the skills that set top performers apart in competitive markets.
Whether you’re a seasoned professional, early in your career, or somewhere in between, this blog is a space to explore our challenges and dive into the practical skills I’ve found most effective. I intend to share what I’ve learned in the field, much originating from people more experienced than myself, and some things I’ve discovered and tested on my own, to help equip the seller in the field to deliver exceptional outcomes for our customers and our organizations.
Outcomes For the Subscriber
Customer expectations have evolved dramatically over the past decade, reflecting a shift toward personalization, transparency, collaboration, and value-driven interactions. Sales reps who can align their skills to these expectations by demonstrating empathy and technical competency as they deliver tailored solutions are best positioned to succeed in today’s competitive and complex sales environment.
This Newsletter will focus on practical skills and topics that align with the following 11 critical skill sets, which are key to success in today’s B2B selling environment.
The ability to go beyond basic product knowledge and offer unique perspectives that add value by synthesizing insights and presenting solutions proactively.
The ability to provide fast, efficient, and personalized interactions.
The ability to deliberately shift away from burdening customers with a need to be "bottle-feed" information and toward a more independent, resourceful approach.
The ability to demonstrate empathy, ask insightful questions, and deliver personalized recommendations.
The ability to demonstrate fluency in financial outcomes and illustrate how our service or solution directly impacts the customer’s bottom line.
The ability to navigate organizational and political dynamics, build consensus, and align our engagement to the priorities of multiple stakeholders.
The ability to be transparent and authentic to earn trust, be forthright about limitations, and position ourselves as long-term partners rather than short-term sellers.
The ability to leverage analytics, industry insights, and non-vendor-produced real-world data to validate our claims and build credibility.
The ability to adapt our communication style, consider diverse perspectives, and show a genuine understanding of the customer’s context.
The ability to build long-term relationships, maintain regular check-ins, and align closely with customer success teams to ensure continued satisfaction and retention.
We must demonstrate the ability to act as advocates for our customers internally, ensuring we deliver on promises, resolve issues efficiently, and tailor solutions to customer objectives.
2 Personal Perspectives
Customer Experience
We should be mindful that customer experience is lived experience. It is inherently subjective, deeply personal, and shaped by individual perceptions and emotions. In B2B relationships, it is not easy to quantify because, unlike tangible metrics, it includes intangible elements like empathy, trust, and satisfaction, which vary significantly from person to person. Consequently, understanding the customer’s lived experience necessitates a thoughtful blend of intuitive perception and behavioral observation in context to respond effectively. As we pick up on these fluctuations and changes, we must thoughtfully translate them to our organizations to ensure we are properly addressing them.
Sales Methodology & Training
A strong understanding of sales methodologies and processes provides a strong foundation for success. But, practical skills are developed through hands-on application, trial and error, and the experience of handling real-world complexities. Bridging this gap requires experiential learning, thoughtful reflection, and ongoing skills development to ensure that theoretical knowledge translates into real-world effectiveness. This newsletter supplements formal sales training, it is not a replacement for them. Ideally, I can provide insights into skills and topics that allow us to accelerate our ability to align how we show up with customers to how they expect to be engaged with.
My Professional Experience
From the beginning of my career, I was fortunate to benefit from exceptional training, mentorship, and guidance from seasoned sales professionals. My formal sales journey began at the Cisco Sales Academy in Raleigh, North Carolina, an immersive two-year program designed for recent college graduates. This highly sought-after and competitive program emphasized developing business acumen and technical expertise, providing me with a robust foundation for success in the field. It was an extraordinary introduction to managing my professional growth and effectiveness as a sales representative.
Following my time at Cisco, I spent two years with Comstor and nearly five with Dimension Data, where I had the privilege of working under outstanding leaders who were instrumental in shaping my career. Marco Cantamessi, a deliberate and visionary sales leader, played a pivotal role in maximizing my potential by strategically assigning me to impactful opportunities. Under his guidance, I collaborated with global client directors Gary Paxton and Liam Rutherford, whose stewardship enabled me to contribute meaningfully to critical global accounts. This experience culminated in my promotion to a Global Account Management role, overseeing relationships with four major pharmaceutical companies.
During this time, I also worked alongside incredibly talented colleagues like Woody Lockhart and Leigh Juul, and I was honored to participate in a corporate-sponsored MBA program at the IE Business School in Madrid, Spain. This milestone further enriched my professional and personal development, providing me with a global perspective on business and leadership.
My tenure at Dimension Data was transformative, teaching me foundational lessons about enterprise software and services sales. These experiences continue to shape my approach today, grounding me in a deep understanding of customer-centricity, strategic account management, and the importance of thoughtful mentorship in professional growth.
My transition to Splunk marked a deeper dive into data analytics and operational intelligence. As a Regional Sales Manager, I conceptualize and execute strategies that expand Splunk’s product portfolio adoption within complex enterprise accounts in the communications, media, and technology verticals.
All my best, and Happy New Year!
Chris