In this episode of the Drop In CEO podcast Ashish Gupta, founder and CEO of ScaleUpExec, shares his journey from co-founding a wireless technology company acquired by Qualcomm, to working at Apple, and eventually starting his own firm focused on fractional leadership for small and medium-sized businesses. They discuss the importance of understanding the needs of both the business and its team, the challenges and strategies involved in transforming distressed businesses, and the benefits of having a versatile COO. Ashish emphasizes the value of introspection for entrepreneurs to clearly define their business goals and align their teams accordingly.

Episode Highlights:

02:28 Ashish Gupta's Journey: From Wireless Tech to Apple

03:44 Entrepreneurial Challenges and Successes

05:52 Transforming a Distressed Business

08:55 Insights on Leadership and Team Building

17:29 The Role and Impact of Fractional COOs

Ashish has had a long journey in business and tech - selling 2 businesses where he was founder-level, managing a $2B/year budget at Apple, and now running a fractional COO firm that has turned around over 20 businesses. He is an expert at helping leaders and businesses reach their potential.

Connect with Ashish Gupta:

LinkedIn: https://www.linkedin.com/in/ashish-gup/

Company Website: https://scaleupexec.com/

For more information about my services or if you just want to connect and have a chat, reach out at: https://dropinceo.com/contact/

See omnystudio.com/listener for privacy information.

In this episode of the Drop In CEO podcast Noel Massie shares his journey from starting as a part-time supervisor to becoming Vice President of UPS’s US Delivery Operations. He emphasizes the importance of intentional leadership, focusing on the development of team members, and shares his insights on effectively communicating and influencing without coercion. Noel discusses his book, 'Congrats You've Been Promoted,' which offers practical advice for new and seasoned leaders alike. Additionally, he talks about his extensive involvement in community service and the impact of projects like second grade literacy initiatives.

Episode Highlights:

09:13 The Importance of Investing in People

20:55 The Importance of Communication Skills

21:31 Directional Communication: A Key Leadership Skill

22:37 The Tactical Side of Leadership

Noel Massie began working for UPS part time during college and rose through the ranks to
become vice president for UPS’s US Delivery Operations. Before his retirement in 2019, he
oversaw 200,000 employees who were led by 12,000 supervisors. In this role, Noel supported
and guided the package delivery and logistic services in the United States. He continues to
mentor young leaders and supervisors.

Connect with Noel Massie:

LinkedIn: https://www.linkedin.com/in/noel-massie-8b7511a/

Company Website: https://noelmassie.com/

Masterclass: https://noelmassie.com/choose-your-bonus-package/#masterclass

For more information about my services or if you just want to connect and have a chat, reach out at: https://dropinceo.com/contact/

See omnystudio.com/listener for privacy information.

In this episode of the Drop In CEO podcast Michelle Drolet, Founder and CEO of Towerwall, to discuss the complexities of cybersecurity and her journey as a leader in the tech industry. Michelle shares her personal and professional background, detailing her rise to CEO, overcoming significant challenges, and her strategies for building robust cyber defense programs for clients. The conversation highlights her resilience through personal adversities, the significance of trustworthy relationships, and the importance of giving back to the community through initiatives like the Towerwall Cyber Summit. Michelle emphasizes the need for organizations to be proactive and vigilant in their cybersecurity efforts, offering insights into how Towerwall partners with clients to secure their digital infrastructure. The episode concludes with inspiring words on leadership, resilience, and the importance of community impact.

Episode Highlights:

02:15 Michelle's Journey in Cybersecurity

07:05 Challenges and Resilience in Leadership

14:40 The Importance of Cybersecurity

27:08 Family and Business: A Personal Insight

Michelle Drolet is the Founder and CEO of Towerwall, a leading cybersecurity firm serving clients like BOSE, Smith & Wesson, Brown University, and UMass Memorial Health. Recognized as one of CTO Magazine’s "Top Women in Cybersecurity" and named to Forbes’ "50 Over 50," Michelle brings decades of experience helping organizations protect what matters most. With a client roster that spans industries and borders—including the Insurance Board of the Bahamas—Michelle is a sought-after thought leader and speaker. She’d be honored to join The Drop in CEO podcast to share actionable insights from the front lines of cybersecurity leadership and strategy.

Connect with Michelle Drolet:

LinkedIn: https://www.linkedin.com/in/michelle-drolet-a926b79/

Company Website: Towerwall.com

For more information about my services or if you just want to connect and have a chat, reach out at: https://dropinceo.com/contact/

See omnystudio.com/listener for privacy information.