Chief Change Officer Episode #345: Sienna Jackson – From Hollywood to Hard Metrics (Part Two)
Release Date: May 5, 2025

Introduction

In episode #345 of Chief Change Officer, host Vince Chan engages in a compelling two-part conversation with Sienna Jackson, a two-time founder and systems thinker. This episode delves deep into Sienna's transition from the entertainment industry to the realm of social impact, exploring her journey, methodologies, and the challenges she has encountered along the way. The discussion provides invaluable insights for growth progressives, visionaries, and changemakers aiming to outgrow themselves and effect meaningful change in the world.

Sienna’s Career Transition: From Entertainment to Social Impact

Sienna Jackson's career trajectory is nothing short of inspiring. Starting college at 14 and interning at the Weinstein Company by 17, Sienna quickly made her mark in the entertainment industry, leading music and content at Spine Glass Media. However, her passion for social good and storytelling eventually led her to pivot towards impact consulting.

At [05:10], Sienna explains, “I wanted to be a citizen of the world and use storytelling through the lens of reporting for good.” Disillusioned by the state of journalism and recognizing the shifting landscape of entertainment with the rise of streaming, she decided to chart a new path. By early 2020, Sienna had established her consultancy, Notera, a B2B software company that leverages AI to help large enterprises manage employment litigation risks and automate HR compliance.

Approach to Measuring and Creating Impact

Sienna emphasizes a structured approach to impact, defining it as “the net positive change rendered as a direct and material result of your actions” ([05:10]). She critiques the prevalent use of "impact" as mere marketing jargon, advocating instead for measurable and predictable outcomes. Her focus lies in Impact Management and Measurement (IMM), utilizing tools like Social Return on Investment (SROI) analysis to create tangible, data-driven impact models.

She elaborates, “If you get an input, an action, you should get a specific reaction or outcome that you can measure, that you can quantify, that you can predict” ([05:10]). This rigorous methodology ensures that impact initiatives are not only well-intentioned but also effective and scalable.

Current Projects and Initiatives

Sienna is currently channeling her expertise into some of the most significant projects in her career. Notably, she is executive producing the Great Rift Valley Innovation Summit in Ethiopia, a collaborative effort with the United Nations Development Program (UNDP). This initiative aims to provide non-dilutive funding to Ethiopian entrepreneurs excelling in healthcare, education, and agriculture ([10:45]).

Her role involves bridging diverse stakeholders across public and private sectors to foster innovation and economic development in Africa. Sienna’s ability to “speak to people in their own language and draw them together” is highlighted as her key strength in building effective coalitions ([22:02]).

Challenges in Impact Work

Throughout her journey, Sienna has encountered several barriers, primarily revolving around the lack of a professional peer community and effective networking within the impact sector. At [15:56], she states, “the big thing that I noticed right out the gate was a lack of professional, peer community and network.”

She identifies silos as a significant obstacle, where different sectors (nonprofits, private sector, etc.) fail to communicate effectively. To address this, Sienna is actively working on creating industry surveys and building a more structured community for impact practitioners through her role at Social Value International ([18:15]).

Final Thoughts and Advice

Closing the episode, Sienna offers a powerful message to aspiring changemakers: “Every single person has their own unique way of doing good in the world. You have something unique to offer that's entirely yours” ([23:01]). She encourages individuals to identify their unique skills and collaborate with existing helpers to maximize their impact.

Vince echoes this sentiment, emphasizing the importance of execution, data collection, and strategic decision-making in scaling impact initiatives ([24:21]). Sienna’s concluding remarks reinforce the idea that impactful change stems from clarity, curiosity, and the courage to take the first step.

Conclusion

This episode of Chief Change Officer showcases Sienna Jackson’s remarkable journey from Hollywood to the forefront of social impact. Her blend of creative storytelling and rigorous impact measurement provides a blueprint for others seeking to drive meaningful change. Sienna’s insights into overcoming industry barriers and her dedication to fostering global collaborations underscore the essence of true leadership in the transformation space.

If you’re inspired by Sienna’s story and eager to embark on your own path of outgrowing yourself, tune into Chief Change Officer on LinkedIn, Apple, Spotify, and YouTube @chiefchangeofficer. Join the community of over 130,000 followers dedicated to ambitious human transformation.

Notable Quotes

• “If you get an input, an action, you should get a specific reaction or outcome that you can measure, that you can quantify, that you can predict.” – Sienna Jackson ([05:10])
• “You can't silo yourself.” – Sienna Jackson ([18:15])
• “Every single person has their own unique way of doing good in the world.” – Sienna Jackson ([23:01])