Revolutionizing Sale – Unleashing the Power of Customer Experience Optimization
Sales Management 07.13.2023

Revolutionizing Sale – Unleashing the Power of Customer Experience Optimization

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In this episode of Sunny Side Up, host Brian Hopper interviews Derek Hall, Senior Director of Solutions Engineering at ServiceTitan. They delve into the evolving dynamics between account executives and solutions engineers, highlighting the need for a value-focused approach. Derek explains the significance of adopting the Challenger Sale methodology, emphasizing the importance of teaching, tailoring, and taking control during the sales process. He emphasizes that prospects have limited time and attention, making it crucial to provide value and relevance to engage them effectively. The conversation underscores the balance between meeting customer needs and maintaining control over the sales process to convey the value story successfully. Derek also shares valuable advice he would give to his younger self, stressing the importance of embracing intellectual curiosity and continuous learning. 

About the Guest

Derek Hall is the Sr. Director of Solutions Engineering at ServiceTitan. Over the last 11 years, he’s worked his way from professional football player to entry-level sales development role to Sales Engineer, eventually building out the Sales Engineering org at ServiceTitan. Over the past 7 years, he’s built a diverse team of 26 ICs and managers. He’s also an advisor with Us In Technology, whose mission is to diversify the Tech C-Suite through mentorship and facilitating the hiring of underrepresented talent.

Connect with Derek Hall

Key Takeaways 

  • The relationship between account executives and solutions engineers is evolving towards a focus on value and problem-solving.
  • The Challenger Sale methodology is influential in today’s sales landscape, emphasizing teaching, tailoring, and taking control.
  • Prospects have limited time and attention, so providing value and relevance is crucial during interactions.
  • Tailoring the message and demo content to the prospect’s needs is essential for engagement and interest.
  • Balancing customer needs with maintaining control over the sales process is a challenge but necessary for conveying the value story effectively.
  • The Challenger Sale methodology arose from the changing sales landscape post-2008 crisis, with more stakeholders involved in the buying process.
  • Successful salespeople in the new buying climate challenge prospects and provide valuable insights and tailored solutions.
  • Derek recommends embracing intellectual curiosity and continuously seeking knowledge and personal growth.
  • Taking statistics and science classes seriously early on can shorten the learning curve in a tech career.
  • Maintaining control over the sales process while being receptive to the prospect’s needs ensures a coherent and impactful value story.
  • Embracing a growth mindset and continuously seeking knowledge and personal development can accelerate professional success.
  • Finding inspiration from diverse sources, such as sports, can provide valuable insights into leadership, mindset, and perseverance.


“Prospects have limited time and attention. If you’re not making them feel like they’re getting value out of their time, they’re going to disconnect.” – Derek Hall

Highlights from the Episode

Can you share some of the insights you learned on your career journey and how you’ve managed to build such a large and successful team?

Derek recounted his career progression from a sales development role to a leadership role in sales engineering. He shared the importance of not restricting oneself or others based on paper qualifications or past roles. He transitioned from cold-calling as an SDR to becoming an account executive by seizing the opportunity to become a sales engineer, a role he had never heard of before. This required him to self-study technical concepts and skills relevant to his job. By demonstrating his knowledge, he earned a junior position which eventually led to more advanced roles. He emphasized the importance of assessing potential team members for their hunger, curiosity, and willingness to learn, rather than merely their academic or professional qualifications. By doing this, he was able to build a diverse and high-performing team that he’s very proud of.

Can you tell us a little bit more about why a team-based selling strategy, particularly between the sales engineer and account executive, is so important?

Derek underlined that trust is the foundation of all relationships, including sales. He stated that people are often more receptive to sales engineers because they’re seen as technical experts with credible information about the product. By aligning their messages and reinforcing each other, the sales engineer and the account executive can build trust with the prospect faster, leading to more efficient sales cycles and stronger relationships.

Can you tell us a little bit about how you are enabling your teams to be more consultative in their approach at ServiceTitan to focus on the problems that they’re solving versus just the features that ServiceTitan offers?

Derek emphasized the concept of ‘attention quota’, indicating that a prospect can only retain about 20-25% of the information presented to them, hence every moment of interaction should be intentional and precious. He strongly disapproves of feature tours, seeing them as ineffective and potentially disengaging for prospects. Derek’s approach to training his teams involves a focus on consultative selling. They use a specific scoring rubric for product demonstrations and measure performance transparently. The training encompasses asking prospects not only about the challenges they want to solve but also about what’s going well with their business. This way, they can better demonstrate how their product can enhance the positive aspects of the prospect’s business, in addition to solving their problems.

Can you explain what the Challenger Sale methodology is at a high level and why you’ve adopted this as the approach for your solutions engineering team and how you train them?

Derek explained that the Challenger Sale methodology was a major influence on his sales approach, introduced to him by a sales director. The methodology originated after the 2008 financial crisis when selling became difficult due to increased stakeholders in the sales process. The successful salespeople at that time were those that “challenged” their prospects. The methodology relies on the concept of “teach, tailor, and take control.” It is about providing value and insights, tailoring the product to the prospect’s needs, and maintaining control over the sales process to ensure the right message is delivered and a coherent story is told. Derek believes that this balance is essential to keep the customers engaged and convey the value of the product effectively.

What is one piece of advice you would give to your younger self based on what you know today?

Derek said that if he could advise his younger self, he would recommend taking statistics and computer science classes more seriously. He believes this would have shortened his learning curve in his later career in tech. Additionally, he would have advised himself to read more leadership books and cultivate his intellectual curiosity earlier in life. His thirst for knowledge grew as he found more direction in his career, and he feels he could have capitalized on this earlier.

Is there a book, blog, newsletter, website, or video that you would recommend to our listeners?




Simon Sinek – Founder at The Curve and Simon Sinek, Inc. 

Ross Biestman Chief Revenue Officer at ServiceTitan

Daymond JohnCEO at The Shark Group

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