134: Jacqueline Freedman: Former leader at Grammarly and WeWork on how to become a trusted Martech advisor

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 C
• She 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 company
• And 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 consultancy

Why 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 the series contained a kernel of truth, the actual events at WeWork were far more intense. Everything depicted in the show was amplified tenfold in reality. This amplification was very much in line with WeWork's brand, known for its high-energy and sometimes chaotic environment. She described her experience of watching the dramatization as somewhat PTSD-inducing due to its accuracy in portraying the underlying ethos of WeWork.

Despite the dramatization, Jacqueline found it fascinating and somewhat validating to see the story unfold on screen. The series succeeded in conveying the core truth of WeWork's journey, even if it couldn't fully encapsulate the extremities of the real-life scenarios. For Jacqueline, revisiting those memories through the show was a mixed experience, balancing between validation and the resurfacing of intense memories.

Her insights underscore the dramatic nature of WeWork’s history and how media adaptations, while engaging, often have to simplify or condense reality. For viewers, it’s a reminder that behind the scenes, the stories of such companies are often more complex and multifaceted than any series can fully capture.

Key takeaway: Jacqueline noted that while "WeCrashed" captured the essence of WeWork, it only scratched the surface of the true events, which were far more intense. The dramatization, though somewhat accurate and PTSD-inducing, validated the chaotic environment of WeWork. However, she emphasized that media adaptations often simplify the complexities of real-life scenarios.

How to Become a Martech Advisor

Balancing Hands On Execution Projects vs Strategic Advice

Jacqueline addresses the nuanced demands of clients in marketing operations (MOPs). While she shares a passion for every facet of MOPs, she acknowledges a point in her career where hands-on tasks like copywriting and sending emails no longer align with her long-term vision. This shift towards focusing on advisement and strategy is something she enjoys, and it's about setting clear expectations from the start with clients.

Each client’s needs vary, which Jacqueline finds exciting. However, it necessitates clear communication about what she offers. When clients require extensive lifecycle or demand generation email execution, Jacqueline is upfront about her role. If it's a short-term need, she might handle it, but for long-term commitments, she refers them to trusted partners. She mentions firms like Modular Marketing and Ragnarok, highlighting her strong relationships with these agencies. This symbiotic partnership ensures clients get top-notch service while allowing Jacqueline to concentrate on strategic advisement.

By focusing on strategy, Jacqueline can provide high-level insights and direction that impact her clients' overall marketing operations. She values the ability to step back from the minutiae and look at the bigger picture, helping businesses navigate their marketing landscapes more effectively. This approach not only suits her professional growth but also ensures her clients receive specialized, high-quality execution from her partners.

Jacqueline’s journey exemplifies the importance of evolving in one’s career and recognizing when to delegate tasks that no longer fit one’s vision. It’s about leveraging strengths and building a network of reliable partners to deliver comprehensive solutions. Her ability to set expectations and offer strategic guidance is a testament to her experience and foresight in the marketing operations field.

Key takeaway: When transitioning to a more strategic consulting role, clearly communicate your focus and delegate hands-on tasks to trusted partners. This allows you to leverage your strengths, provi...