Dillon McDermott

Director of Sales | Boston, Massachusetts, United States

Professional Overview

Dillon McDermott is an accomplished sales executive with over a decade of experience driving revenue growth and leading high-performing teams. As the Director of Sales at Help Scout, he is responsible for overseeing the company's global sales strategy, managing a team of top-performing sales professionals, and spearheading initiatives to unlock new market opportunities. With a strong background in the SaaS and customer experience technology industries, Dillon has developed exceptional expertise in enterprise sales, account management, and go-to-market strategy.

Experience Summary

Current Role

As the Director of Sales at Help Scout, Dillon is responsible for leading the company's global sales efforts, setting and achieving ambitious revenue targets, and developing a world-class sales organization. He oversees a team of sales professionals, providing strategic direction, coaching, and support to ensure the successful delivery of the company's customer-centric solutions. Under Dillon's leadership, Help Scout has consistently exceeded its sales goals, expanded its customer base, and solidified its position as a leader in the customer service software market.

Career Progression

Dillon's career trajectory has been marked by progressive leadership roles and a track record of driving revenue growth and operational excellence. Prior to joining Help Scout, he served as the Head of Worldwide Sales at Zowie, where he successfully scaled the company's global sales operations and helped it secure a market-leading position. Before that, Dillon was the Vice President of Sales at Thankful AI (acquired by Gladly), where he played a pivotal role in driving the company's rapid expansion and successful acquisition. Earlier in his career, he held sales leadership positions at SurveyMonkey, GetFeedback, and TechTarget, where he consistently exceeded sales targets and earned a reputation as a strategic, results-oriented sales executive.

Academic Background

Dillon holds a Bachelor of Science degree in Business Administration from the University of Massachusetts Amherst, where he graduated cum laude.

Areas of Expertise

• Enterprise sales and account management

• Go-to-market strategy and market expansion

• Sales team leadership and performance optimization

• Customer experience and customer success

• SaaS and enterprise software sales

Professional Impact

Throughout his career, Dillon has demonstrated a strong commitment to driving innovation and delivering exceptional results. He has a proven track record of launching successful sales initiatives, forging strategic partnerships, and leveraging data-driven insights to optimize sales processes and team performance. Dillon's industry contributions include speaking engagements at leading sales and customer experience conferences, as well as active involvement in professional organizations such as Pavilion, where he serves as an executive member.

Conclusion

Dillon McDermott is a seasoned sales executive with a demonstrated ability to build and lead high-performing teams, drive revenue growth, and deliver exceptional customer experiences. With his strong background in the SaaS and customer experience technology industries, Dillon is well-positioned to continue making a significant impact as the Director of Sales at Help Scout, helping the company achieve its strategic objectives and solidify its position as a market leader.