Navigating Sales Success: Meredith Chandler’s Journey

March 20, 2024
Content Marketing | Marketing Strategy | Taking the Lead

Episode Summary

In the latest episode of Taking the Lead, host Christina Brady welcomes guest Meredith Chandler, Head of Sales at, to dive into her unique journey through the sales world and her insights on building successful teams. From teaching English in Spain to navigating the complexities of tech sales in San Francisco, Meredith’s path is a testament to adaptability and resilience. She shares her experiences, from early challenges to achieving leadership roles in high-growth startups, offering listeners a comprehensive view of her career evolution.

Christina and Meredith discuss the pivotal moments that shaped Meredith’s approach to sales and leadership. One notable story Meredith shares involves a significant challenge with commission structures early in her career, highlighting the importance of transparency and fairness in sales incentives. This experience, Meredith explains, taught her valuable lessons about advocating for oneself and the critical role clear communication plays in team dynamics.

The conversation also covers Meredith’s strategies for managing remote teams, a timely topic given the recent shift towards remote work. She emphasizes the importance of creating a culture of trust and accountability, sharing practical tips on fostering engagement and productivity in a virtual setting. Meredith’s success in leading three remote teams underscores her innovative approach to leadership and team building in today’s digital workplace.

Lastly, Christina and Meredith explore the future of sales and leadership. Meredith offers advice to aspiring sales leaders, emphasizing the significance of continuous learning, empathy, and the ability to adapt to change. Her perspective on the evolving sales landscape provides valuable insights for professionals at all stages of their careers.

This episode of Taking the Lead not only showcases Meredith’s remarkable journey but also serves as a resource for listeners seeking to enhance their sales and leadership skills. Christina’s engaging discussion with Meredith offers actionable strategies and a dose of inspiration for navigating the challenges and opportunities of the sales industry.

Featured Guest

Name: Meredith Chandler

What she does: Head of Sales


Noteworthy: Meredith Chandler, with a background in teaching English in Spain, transitioned into tech sales upon returning to San Francisco, excelling at Yelp and overcoming challenges to become Head of Sales at Her journey reflects resilience and adaptability, shaping her into a dynamic sales leader.

Key Insights

Meredith Chandler: Mastering Remote Team Dynamics

Meredith shares her journey of managing three remote teams, emphasizing the joy and productivity that can be achieved despite common misconceptions about remote work. She challenges the notion that virtual environments are barriers to team bonding, highlighting innovative approaches to foster engagement and camaraderie. Meredith’s perspective is a testament to the evolving nature of workspaces, showcasing her ability to adapt and thrive in a remote world. Her strategies underline the importance of creativity and personal connection in overcoming the physical distances between team members.

Commission Clarity: Meredith Chandler’s Advocacy for Transparency

Meredith Chandler discusses the pivotal experience that led her to prioritize commission transparency in her career. After facing challenges with commission discrepancies, she emphasizes the necessity of understanding commission plans from the onset. Meredith’s advocacy for clear and fair compensation structures speaks volumes about her commitment to fairness and accountability in sales roles. Her insight serves as valuable advice for sales professionals at all levels, highlighting the importance of vigilance and open communication about compensation.

Fostering Fun and Productivity: Meredith Chandler’s Innovative Approach

Meredith Chandler dives into the importance of injecting fun into the workplace to boost team morale and productivity. By sharing personal anecdotes and successful initiatives, she illustrates how fun can be a strategic tool for engagement. Chandler’s approach goes beyond conventional team-building activities, suggesting creative solutions like Airbnb Experiences for team events and personal interest discussions to strengthen team bonds. Her methods reflect a deep understanding of the sales environment and the need for balance between work and enjoyment, underscoring her innovative leadership style.

Episode Highlights

Introduction and Background of Meredith Chandler

The episode begins with Christina Brady welcoming Meredith Chandler and briefly discussing the episode’s partners. Meredith then shares her journey from teaching English in Spain to entering the tech and sales industry in San Francisco. She recounts her initial experience at Yelp, emphasizing the rigorous sales training and the challenges of cold calling.

“So I pulled the plug, moved back to San Francisco, and started working at a little company called Yelp. Maybe some of you have heard of it. It’s funny. We used to do cold calling there, obviously.”

The Rigors and Humor of Cold Calling

Meredith discusses the demanding nature of her role at Yelp, where she was required to make 80 cold calls a day and maintain a significant amount of talk time. She shares humorous anecdotes about finding creative ways to meet these metrics, including listening to movie theater times and engaging in quirky conversations with gatekeepers.

“So a lot of times you’re just listening to movie theater times […] We had our fun with it where we could.”

Transition to a New Tech Company and Facing Challenges

Meredith narrates her transition to another tech company where she excelled as a top sales representative. She highlights the dual pressures of meeting new business quotas and ensuring customer retention. Her success story takes a turn when she discusses an unexpected challenge related to commission overpayments.

“I was doing really well at this company. I was a top rep out of hundreds, the money’s coming in. I’m 26 years old… Plot twist! I go in on what must have been just a regular Tuesday, Wednesday morning.”

Commission Overpayment Crisis and Its Aftermath

The discussion takes a serious turn as Meredith shares a significant career challenge. She was informed by HR that she had been overpaid in commissions for two years, amounting to $60,000, and was asked to repay it. This situation led her to seek legal advice and reconsider her position and future in the company.

“They say, Meredith, you’ve done a great job here. However, there’s been a mistake with your commissions and we’ve overpaid you a little bit and we’re going to need that money back.”

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