Gaining the Technology Leadership Edge, Episode #67

Breaking the Negative Stereotypes of Sales with Sean Sheppard

Show Notes

About the Guest(s):

Sean Sheppard is a seasoned Silicon Valley veteran with over 30 years of experience in the tech industry. A serial tech entrepreneur, Sean has achieved three exits and has valuable experience in venture funds, particularly in B2B seed-stage investing. He is also known for founding a school dedicated to training individuals for the startup community. Currently, Sean is a major stakeholder in Uplus, a corporate venture building firm, and is involved in the development of an AI platform designed to enhance ideation, market research, and innovation for large enterprises.

Episode Summary:

Ever wondered what makes top sales influencers stand out? In this episode of “Gaining the Technology Leadership Edge,” Mike interviews Sean Shepard, a Silicon Valley veteran celebrated in the world of sales and marketing. Sean shares his journey of transforming sales into a true profession and overcoming societal stereotypes. He delves into the crucial aspects of sales training and how emotional intelligence, critical thinking, and focus are pivotal for successful sales strategies.

The conversation also explores Sean’s venture-building experience, particularly through Uplus, where they help large enterprises by commercializing intellectual property and building digital businesses. He underscores the importance of stakeholder support and having a balanced team with diverse skill sets. The episode wraps up with discussions on overcoming challenges in leadership and the importance of focusing on people over products.

Key Takeaways:

  • Sales as a True Profession: Sean stresses the need to professionalize sales akin to law or medicine, understanding its pivotal role in business success.
  • Human Element in Sales: Incorporating emotional intelligence, effective communication, and personal development into sales strategies.
  • Importance of Training: How proper training can significantly improve sales outcomes and customer experiences.
  • People Over Products: Why valuing people and their skills is crucial in leadership and venture building.
  • Balancing Teams: The necessity of having diverse skill sets within a team to successfully scale startups.

Notable Quotes:

  1. “I think if you develop a person, you develop a professional.” – Sean Sheppard
  2. “Sales is a true profession, like being a lawyer or being a doctor or being an accountant.” – Sean Sheppard
  3. “Fall in love with the people, not the product.” – Sean Sheppard
  4. “Just because we all speak English doesn’t mean we speak the same language.” – Sean Sheppard
  5. “Nothing happens until someone sells something.” – Sean Sheppard

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Episode Details

Transforming Sales and Leadership: Insights from Sean Sheppard

Key Takeaways:

  • Sales should be viewed as a true profession, requiring as much skill and dedication as any other.
  • Embracing personal growth and emotional intelligence is crucial for successful sales and leadership.
  • Aligning with the right people and teams significantly de-risks innovation and business ventures.

Elevating Sales: The True Profession

In a world where sales often carry a negative connotation, Sean Sheppard is on a mission to change that perception. With 30 years of experience in Silicon Valley, Sean argues that sales should be recognized as a genuine profession, akin to being a lawyer, doctor, or accountant. He points out that societal norms unfairly undervalue the importance of sales.

“Nobody grows up saying, I want to be in sales. Yet without sales, nothing happens,” Sean explains. “They’re as important a part of any business, successful business, as any other part of that business.”

Sean’s passion for professionalizing sales shines through in his effort to counter the stereotypes perpetuated by media and society. Many people associate sales with pushy retail or car sales experiences, causing high turnover rates in the industry. Sean believes that fundamental changes are needed to prepare individuals better and foster a respect for the profession from a young age.

His method involves studying numerous sales methodologies, focusing on human behavior, and integrating tools that improve both personal and professional development. He emphasizes the need to develop skills such as business acumen, communication, emotional intelligence, and critical thinking.

“Your job is to help others get what they want, and you’ll be successful if they are successful,” says Sean. “It’s not about you; it’s about them.”

The Crucial Role of Training and Human Elements in Sales

Mike shares a personal experience that highlights a common issue in sales: poor training. He recounts how a salesperson failed to recognize his completed transaction due to an oversight with automated systems. This experience underscores how critical proper training is in forming positive customer relations.

Sean acknowledges this and elaborates on the broader implications within corporations. He emphasizes that beyond technical skills, human elements like effective communication and emotional intelligence play pivotal roles in sales success.

“Just because we all speak English doesn’t mean we speak the same language,” Sean notes, stressing the importance of understanding interpersonal dynamics and overcoming the non-human component that often accompanies tech-centric roles.

Improving these ‘soft’ skills, often mislabeled as such despite their complexity, can bridge gaps between the technical and human aspects of sales and leadership. This is especially important as technology advances and intends to scale and better human performance.

Aligning with the Right People: A Pillar for Successful Ventures

When it comes to building successful ventures, partnerships, or startups, Sean insists that the key lies with the people behind the ideas. His experience highlights the importance of aligning with individuals who share similar values and demonstrate reliability, particularly when challenges arise.

“To me, it’s all about focusing on the people behind the product of the technology. Do they have the right values that I care about? Can I trust them? Do I believe in them?” Sean emphasizes.

He points out that understanding one’s own limitations and seeking complementary skills is vital for the growth of any business. For instance, tech founders often have different skill sets than what is required to manage people and drive sales. Recognizing this helps in onboarding the right teams and de-risking ventures.

Sean illustrates this with his investment thesis, acknowledging the necessity for tech founders to possess a growth mindset, be coachable, and recognize the need to involve professionals who can handle areas outside their expertise. This mindset not only ensures a balanced team but also promotes sustainable growth through collaboration.


In efforts to revolutionize sales, Sean Shepard champions a holistic approach that integrates professional skill development, effective training, and the value of human elements. His insights reveal that true success in sales and leadership lies in professionalism, emotional intelligence, and aligning with people who share your values and goals. Sean’s philosophy underscores the necessity of involving the right individuals, fostering human connections, and consistently striving for personal growth.

This approach not only redefines the sales profession but also sets a blueprint for aspiring leaders to follow, ensuring that innovation, collaboration, and human-centric practices lead the way in transforming businesses and society.

Contact Information for Sean Sheppard

Timestamp Summary
0:00 Professionalizing Sales: Transforming Perceptions and Practices
9:19 The Impact of Poor Training on Business Experiences
10:37 Lessons in Innovation, Leadership, and Entrepreneurship
15:24 Balancing Tech Expertise with Leadership and Communication Skills
20:50 The Importance of Saying No to Unfit Opportunities
23:59 Connecting with Sean Sheppard on LinkedIn and Twitter