134: Jacqueline Freedman: Former leader at Grammarly and WeWork on how to become a trusted Martech advisor
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What’s up everyone, today we have the pleasure of sitting down with Jacqueline Freedman, CEO and Founder at Monarch Advisory Partners. Summary: Jacqueline straps on her jetpack and invites us to soar through the martech skies, teaching us how to navigate the journey of becoming an independent martech advisor. From hands-on execution tasks strategy and advisory projects and assembling a futuristic composable martech stack, we cover a lot of air miles. We navigate the build versus buy decision in martech, the realities of composable CDPs and embracing user-friendly modern marketing automation tools. About Jacqueline Jacqueline started her career in Account and relationship management before joining WeWork where she would eventually settle into a Global Engagement Marketing and Operations Manager role as the fifth marketing hire during the company’s hyper-growth She later joined an email and lifecycle growth agency as the 2nd team member and built out their NYC office where she worked with startups ranging from seed to series CShe then moved over to Grammarly as the founding Marketing Operations hire where she built out the B2B MOPs team and led their marketing technology stack to support their transition to a B2B2C companyAnd recently Jacqueline strapped on her jetpack and went out on her own as a solopreneur founding Monarch Advisory Partners, a full-stack Marketing Ops and Martech consultancyWhy Introspection is the Secret Weapon for Aspiring Entrepreneurs Jacqueline, reflecting on her transition from Grammarly to entrepreneurship, reveals the depth of her decision-making process. With a family history rooted in entrepreneurship, Jacqueline always envisioned herself running her own business. Observing her father and grandfather, she felt like she had a front-row seat to an MBA. This early exposure planted the seed of entrepreneurship, but it wasn’t until she recognized her unique skill set that she felt truly ready to take the plunge. The decision wasn’t impulsive. Jacqueline emphasized the role of introspection and reflection in her journey. She spent a year contemplating the right moment, fueled by her natural tendency to overthink. Through late nights and early mornings, she assessed her career achievements, from scaling WeWork during its prime to steering Grammarly’s shift to B2C. These experiences solidified her belief in her capabilities, leading her to recognize that she was ready for the entrepreneurial leap. Jacqueline’s courage was also bolstered by her practical approach. While at Grammarly, she had already begun advising several founders, driven by her passion for problem-solving rather than monetary gain. These conversations not only honed her skills but also provided a soft landing into entrepreneurship. By the time she officially launched her business, she had a lineup of clients ready, thanks to her reputation and the support of colleagues and partners who championed her abilities. Her journey highlights the importance of strategic preparation and the value of building a strong professional network. Jacqueline’s story is a testament to how a combination of introspection, practical experience, and a supportive community can make a significant career transition smoother and more successful. Key takeaway: Use introspection to identify your unique skills and career achievements. Reflecting on these aspects will not only boost your confidence but also clarify your readiness for major career changes, like transitioning to entrepreneurship. How TV Dramatization Barely Scratches WeWork's Reality When asked about the accuracy of the WeWork TV show "WeCrashed" on Apple TV, Jacqueline offered a candid perspective. Having watched all the content related to WeWork, she noted that "WeCrashed" starring Jared Leto and Anne Hathaway, came closest to capturing the essence of the events. However, she emphasized that the series only scratched the surface of what truly transpired. Jacqueline explained that while
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