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Writer's pictureEsther Ayorinde-Iyamu
Sep 253 min read

5 Key Factors for Successfully Leading an Overlay Sales Team: Insights from Garrett Claridge

Ever wondered what it’s like to be or lead a team of Product Sales Specialists? Ever been on a sales team and suddenly find yourself promoted to lead the very people who were once peers? How do you acquire a team who used to be peers?


In an episode of the Dear Future CRO Podcast, we had the pleasure of speaking with Garrett Claridge, Regional Sales Manager of Webex at Cisco. Garrett shared invaluable insights on what it takes to lead an overlay sales team effectively, a team of former peers at that. Here's a summary of the top five key factors that are critical for success:


1. Building Personal Connections and Trust:

Garrett emphasized that understanding your team on a personal level is crucial. Knowing their motivations, whether it’s family obligations or personal aspirations, helps in fostering a strong team dynamic. According to Garrett, "You should be able to say, Jane is married for ten years. She's got three kids. One's about to go to college. You can paint a picture in your mind of why she's doing what she's doing." This helps in aligning your leadership style to suit individual team members.


2. Establishing Credibility Early:

As a new leader, demonstrating your capability to manage not just sales but also complex customer relationships is essential. Garrett noted, "What they were really interested in is, how's this guy going to be as a leader? Could I put him in front of an upset customer executive? And could he not only stand the pressure but maybe get the emotion removed from the situation and get the relationship back on track?”


3. Influencing Through Accountability:

Garrett stressed the importance of using influence rather than authority to drive performance. He shared, "My goal was never to be micromanaging every single aspect of that business but rather empowering and influencing them to go and leverage their strengths." Clear accountability and empowering team members to use their strengths lead to better outcomes.


4. Openness to Change:

Adaptability is a recurring theme in Garrett's advice. He encouraged aspiring leaders to be open to change, stating, "Be open to change. The more open you are, the better you’ll feel personally, and your personal brand will shine if you're willing to take on new, challenging roles that others may shy away from."


5. Leveraging Technical Expertise and Collaboration:

In the complex environment of tech sales, understanding and leveraging the technical capabilities of your team can significantly impact success. Garrett recalled his time working with Amazon, "That time actually took me deeper into the walls of Cisco in terms of leveraging the people that build our products and determine those product roadmaps. Bringing them in front of the customer built deeper trusted relationships and collaboration between companies."


Final Thoughts:

Garrett’s journey from a specialist role to leading a specialist sales team highlights the multifaceted nature of sales leadership. For anyone aspiring to grow into a technical specialist sales role, his advice centers around curiosity, networking, and embracing change while maintaining a strong, personable connection with your team.


Tune in to the full episode to dive deeper into Garrett’s experiences and gain more actionable insights here:




GrowthQ is an AI-Powered Career Navigation platform that puts the talent in the drivers seat, allowing employers to apply to you. If you’re a job seeker looking for a role in tech sales as a product sales specialist, match to your next dream job at www.GrowthQ.co.




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