Madeline Masterson: A Trailblazer in Leadership and Business Success

Madeline Masterson is a visionary leader who has made her mark in the industry through a journey of continuous growth and creating positive impacts. Her career began at Amazon, where she realized her passion for making a difference for sellers from an external perspective. This drive led her to join an Amazon agency, but her desire for more autonomy pushed her to change companies once again. It was during this transition that The Master Agency (TMA) was born, driven by Madeline’s determination to create a better environment for account managers. Her personal evolution mirrors her professional growth, characterized by a constant quest to improve and make a meaningful impact.

For Madeline, leadership encompasses two vital aspects. Firstly, it involves having a clear vision and the ability to forge a path even when one doesn’t exist. True leaders are creators who fearlessly navigate uncharted territories. Secondly, leadership entails trusting and empowering the people one works with, setting them up for success and fostering a culture of innovation. By nurturing a sense of ownership and allowing others to tap into their creative potential, leaders can inspire their team members to become creators themselves, fostering a virtuous cycle of growth and accomplishment.

As a woman in a leadership position, Madeline has encountered various challenges throughout her journey. During her time at Amazon, she noticed a bias towards male colleagues for special projects and advancements. Rather than passively waiting for recognition, she took proactive steps by joining meetings uninvited and eventually began leading them, thus proving her capabilities. Madeline also emphasizes the importance of letting one’s work speak for itself, allowing achievements to outweigh any gender-based biases or stereotypes.

Balancing the demands of work and personal life is a priority for Madeline and was one of the driving forces behind establishing TMA. Recognizing the lack of true work-life balance in many male-dominated companies, TMA takes a different approach. By carefully aligning account managers with accounts and encouraging time away from work for family and personal hobbies, TMA ensures its team members do not experience burnout. This approach has resulted in a low attrition rate, strong client relationships, and a healthier work-life integration for all.

Difficult decisions are an inevitable part of leadership, and Madeline has had to make some challenging choices. One particularly difficult decision involves team members who do not uphold the company’s values of honesty, transparency, and integrity. Despite the difficulty, she remains steadfast in her commitment to maintaining a cohesive and values-driven team, leading to the necessary but difficult choice of letting go of individuals who no longer align with the company’s core values.

Creating a culture of diversity and inclusion is fundamental to TMA’s identity. As a women-, minority-, and veteran-owned agency, diversity is ingrained in their DNA. Rather than actively cultivating diversity, TMA’s inclusive culture naturally attracts diverse talent, enabling them to leverage the strength of different perspectives and backgrounds.

To stay at the forefront of the industry, Madeline and her team prioritize staying up-to-date with industry trends and innovations. They maintain close relationships with partners involved in cutting-edge tool development and actively participate in Amazon’s pilot and beta programs. By seeking out new opportunities and boldly leading brands to the digital frontier, TMA remains at the forefront of their field.

Handling conflict within the team is approached with transparency and a “listen first” attitude at TMA. Honest conversations are encouraged, providing everyone with the opportunity to express their views. This approach fosters patience, reflection, and collaborative problem-solving, ensuring that the team remains focused on their shared goals and celebrates collective successes.

Madeline takes great pride in a long-standing partnership with a brand that TMA has worked with for several years. Through effective collaboration, diligent goal setting, and a commitment to transparency, TMA has helped this brand achieve remarkable growth, with annual revenue increasing from less than $500k to nearly $2M. The strong bond built on trust and shared successes has made this partnership a source of immense pride for Madeline and her team.

For women aspiring to leadership positions in business, Madeline offers valuable advice: always bet on yourself. Rather than conforming to preconceived notions of what it means to be a “girl boss” or a “woman in business,” she advises women to focus on doing their job in a way that aligns with their values and brings personal fulfillment. By following their intuition, listening to their gut, and betting on themselves, women can forge their own paths and be amazed by the progress they make and the impact they create.

As a leader, Madeline embraces risk-taking by betting on herself and always having contingency plans. She believes in the importance of being prepared for different outcomes and not becoming overly attached to specific approaches. By maintaining flexibility and adaptability, leaders can make informed decisions and navigate uncertainties effectively. Madeline also emphasizes that the slow road is often the right road, cautioning against over-leveraging oneself for short-term gains.

Building and maintaining strong relationships with clients and customers is a priority for TMA. They approach client interactions as true partnerships, taking ownership of their work and ensuring they deliver outstanding results. Effective communication plays a crucial role in these relationships, with TMA providing regular updates, transparently sharing strategies, celebrating wins, and proactively addressing any challenges that arise.

TMA is actively involved in supporting gender equality and empowering women through their partnership with the Live Like Billy Foundation. This foundation, named after a dear friend and mentor, aims to help women find their confidence in the workplace and embrace challenges and opportunities. By paying forward the mentorship and support Madeline received, TMA contributes to a more inclusive and empowering work environment.

While revenue goals and individual achievements are important, TMA primarily measures success through lasting partnerships and relationships. The fact that almost 30% of their clients have remained with TMA for several years speaks volumes about the agency’s ability to drive results and maintain strong connections. This focus on cultivating enduring relationships and delivering tangible value underscores TMA’s mission and guides their progress.

Looking ahead, Madeline sees the biggest challenges and opportunities for women leaders in business revolving around taking the leap. Despite being one of the few female Amazon agency owners, she believes that there is an abundance of talented women experts in the field who have the potential to succeed as leaders. Encouraging more women to bet on themselves and seize leadership opportunities will be crucial in shaping a more inclusive and diverse business landscape.

Madeline Masterson’s inspiring journey as a leader and her commitment to empowering others serve as a beacon of hope for aspiring women leaders. Her unwavering determination, emphasis on personal fulfillment, and dedication to creating a balanced and inclusive work environment make her a true role model in the industry. Through her visionary leadership and the success of The Master Agency, Madeline paves the way for a more equitable and prosperous future in business.