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Dynamic Strategist | Influential Leader | Experienced Business Consultant

Rachel Winkelman

Rachel Winkelman is a Dynamic Strategist and Influential Leader with 20 years of experience in building meaningful connections across a variety of industries. Informed by an accomplished background in strategic consulting and her Master’s Degree in Business Administration, Winkelman is an agile leader committed to transparency and reliability in driving organizational growth.

At Pinterest, a global social media powerhouse that revolutionized the way brands and consumers communicate, Winkelman serves as the Sales Manager for the Consumer Packaged Goods (CPG) industry. Her leadership guides a consultative sales team to connect Fortune 500 companies and emerging industry-leaders with Pinterest’s near 500 million users. Utilizing strategic communication and data-driven storytelling, Winkleman bridges connections that inspire, engage, and motivate stakeholders.

Previously at The Cambridge Group, Winkleman ascended to the role of Director, Assistant Principal over a 6-year tenure. She led efforts to propel companies toward profitable growth, formulating customer-centric strategies that encompassed segmentation, innovation, and demand creation, while differentiating them from their global industry peers.

Early in her career, Winkleman enriched her strategic acumen at Tribune Interactive and Sears Holdings. Here, she leveraged her operational skills to optimize business development processes and inventory management through planning and analysis. These experiences further honed her proficiency in identifying opportunities for growth and innovation, elements she later brought to her leadership roles.

Winkelman’s educational foundation has been instrumental in shaping her approach toward strategic leadership. She holds an MBA from the University of Chicago’s Booth School of Business and graduated Cum Laude with a Bachelor’s degree in Urban Studies from the University of Pennsylvania. 

Motivated by a desire to remove intrinsic and extrinsic barriers for others, Winkelman is in the process of becoming a Volunteer Doula with Chicago Volunteer Doula, a birth justice organization focusing on vulnerable communities. These roles reflect Winkelman’s dedication to driving change both professionally and within her local community.

Winkelman is a bold advocate for transparency and meaningful connections, breaking down barriers to create an environment where everyone can thrive. By combining passion with purpose, she is dedicated to creating value and driving positive results in the workplace and across her broader community. Her story is a testament to the power of persistence, transparency, and the unwavering belief in breaking down barriers for the betterment of all.

Championing transparency in connections, community, & value-creation.

Leading Expertise:

  • How to strengthen relationships with relational, agile leadership

  • How to craft personalized connections for every interaction

  • Why cultural transparency drives peak performance

  • The intrinsic & extrinsic barriers we must break in & out of the workplace

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