Maxwell Mickey, the Vice President of Sales at E4E Relief, carries a deep-rooted background in sales that he attributes to his family. His father spent his entire career in sales, and his farmer grandfather often said, “If you can sell, then you’ll have a job.”

Maxwell’s career journey is a testament to the adaptability required in the sales field. Starting in the financial sector with aspirations of becoming a trader, he quickly realized the trading world was not for him. He made a bold decision to pivot, stepping back in his career to join a startup in Charlotte, where he took on an SDR (Sales Development Representative) role. This unique journey underscores the importance of being open to new opportunities and roles in the sales profession.

Over the last ten years, Maxwell has thrived in B2B sales, holding various positions from SDR to CRO in different organizations. He experienced both failures and successes, learning and growing from each. He believes that sales are fundamentally about telling a story, crafting a narrative, and solving problems for people.

The conversation surrounding sales automation is increasingly relevant today. With his experience as a VP of Sales, Maxwell joins hosts with extensive consulting backgrounds to examine the topic from an executive perspective.

Maxwell’s journey into sales was not straight. He began at a brokerage firm, obtained federal stockbroker licenses, and later moved into banking. Eventually, he realized that his true passion was in sales, and he has remained committed to it for over a decade.

Sales Automation and Its Challenges

While salespeople often seek automation to maximize their efforts and financial returns, it’s crucial to maintain a balance. Over-automation can lead to a loss of personal touch, which is often the key to effective sales. Finding the right equilibrium between automation and personal engagement is essential for successful sales strategies.

At their core, most salespeople desire efficiency and strive to maximize their potential. This desire pushes them toward adopting tools and strategies that have worked for others. Yet, it’s crucial to remember that what works for one organization might not work for another. There is an overwhelming amount of information available about sales automation today. Salespeople frequently attempt to copy strategies that seem successful elsewhere without considering what truly fits their organization’s needs. 

This can lead to ineffective automation efforts.Sales automation is a powerful multiplier, enabling salespeople to accomplish more with less effort. But again, balance is key. An over-reliance on automation risks losing the personal engagement that makes sales effective.

A compelling question arises: do salespeople genuinely require automation, or are they simply following mandates from leadership? They may be driving demand for automation because they recognize its potential to help them meet their goals.

Today, sales automation is no longer a “nice to have”—it’s essential for staying competitive. However, leaders must think carefully about who will benefit most from automation: the new salesperson or the seasoned veteran.

When evaluating an organization, speaking with senior salespeople is often more beneficial. Their experience allows them to offer valuable insights, while junior salespeople still need to get their hands dirty and learn foundational skills.

Sticking To The Fundamentals

Junior salespeople often misuse automation tools such as automated cadences and AI-powered email writing. Without enough real-world experience, they tend to rely on these tools to produce low-quality output rather than using them strategically.

Senior salespeople, in contrast, know how to leverage automation effectively. They multiply their efforts, learn from available tools, and avoid common mistakes. For example, senior reps might upload transcripts to large language models and query them for deeper insights into customer conversations.

Basic skills like note-taking and asking the right questions remain fundamental to a salesperson’s success. Experience with failure is equally important, as it builds resilience and problem-solving abilities.

Sales automation has evolved from simply automating processes to AI tools that can analyze conversations and provide insights. Senior salespeople use these tools wisely, while junior reps may use them to produce generic, lower-quality content.

The discussion around AI notetakers exemplifies this shift. While automation can replace specific administrative tasks, the underlying skills — like actively listening and note-taking — are still essential for a salesperson’s growth and success.

Ultimately, senior salespeople treat automation tools as learning opportunities and strategic enhancers. Without enough context or understanding, junior reps often use them merely as shortcuts to produce content quickly, which rarely achieves the desired quality.

Effective Use of Sales Automation

Every salesperson has two primary jobs: getting in front of clients and closing deals.

The first role involves finding and attracting potential buyers. The second role consists of developing the skills necessary to close deals effectively. Organizations should use sales automation to perfect one of these roles. Early versions of sales automation primarily focused on the first role: getting in front of more buyers.

Problems arise when organizations attempt to automate everything without identifying specific issues they need to solve. For example, automation should not just be about increasing output; it should address problems like an alarming close rate or insufficient lead volume.

To use automation effectively, organizations must adopt a strategic approach. They should first identify their specific challenges and then deploy automation tools to solve those problems. Simply adding volume without a clear strategy is a recipe for poor results. A strategic approach to sales automation ensures that the tools are used to address specific issues, leading to improved sales performance.

An example of ineffective sales automation is when SDRs send out massive amounts of automated emails — such as 5,000 emails daily. This practice can severely damage a company’s domain health and email reputation. Sales automation needs to be flexible yet controlled. Organizations must prevent misuse, especially among junior staff, who may prioritize quantity over quality. The personal touch in sales must not be sacrificed in the name of automation.

The rise of artificial intelligence (AI) in sales automation demands careful consideration. Organizations must apply AI thoughtfully to solve specific issues rather than unquestioningly increasing volume, especially when transforming customer engagement.

The Rise of Sales Tech and AI

Sales tech has seen explosive growth. Tools now exist for buying signals, data enrichment, and trigger-based selling. Companies like Lavender offer automated email writing services. AI-powered call systems have also emerged alongside large language models.

Determining which aspects of sales should never be automated remains complex. Some automation, such as identifying problems or pulling specific data points, can be beneficial. However, automating outreach often leads to generic email cadences and the notorious “spray and pray” approach.

Experience vs. Automation in Sales

Some sales veterans with over 25 years of experience have found success without heavily relying on automation. They have built lasting careers through relationships, deep business understanding, and strategic thinking. However, the potential of automation to enhance these skills and strategies is an exciting prospect for the future of sales.

This observation suggests that while automation can help, it is not strictly necessary for achieving sales excellence, especially for high-level sellers.  However, replicating the career paths of these seasoned professionals is not scalable. Organizations cannot realistically wait 20 years for a new hire to develop into an elite seller. Consequently, many companies lean heavily on automation to accelerate ramp times, often leading to unrealistic expectations. You can always boost your SDR performance with Expert Ramp-Up tips.

The pressure created by automation demands — creating content, closing deals, and maintaining relationships at warp speed — can be immense. High-level sellers who spent decades honing their craft do not operate at that pace, nor should they.

Organizations often misunderstand this conflict. As a result, many experienced sellers hop between companies without building long-term depth and loyalty from years of work with one employer.

Maxwell and the hosts agree that while automation has a role, it is not a replacement for the nuanced skills and relationship-building capabilities that experienced sellers bring. Organizations must balance deploying technology and respecting the craft of sales.

Scaling Sales Teams and Automation Traps

Many clients lack systematic thinking when scaling their sales teams. Instead of hiring two seasoned professionals, they often hire ten less-experienced reps, hoping that automation will bridge the skill gap. This approach typically leads to large organizations filled with people whose primary job is maintaining systems and managing automation, not selling. 

The dream of a fully automated sales stack—combined with a team that knows how to manage it—sounds appealing, but it usually results in bloated, inefficient sales organizations.

Automating Tasks for Account Executives

When examining the work of account executives, it is crucial to identify which parts of their jobs can and should be automated. Administrative tasks like data entry and note-taking are prime candidates for automation.

However, organizations must proceed carefully. Automating administrative work should free up account executives to focus more on strategic selling activities — not simply flood them with additional low-value tasks.

If you want to watch the whole conversation and hear all these insights directly from Maxwell Mickey and the hosts, you can check out the entire YouTube video here: