Member since January 2024
Jessica Cumming is an executive leadership coach, keynote speaker, success strategist, trainer, and podcast host with nearly two decades of leadership, training, and team transformation experience at Dell Technologies. She helps professionals and leaders navigate career and life transitions with clarity, confidence, and intentional action.
Throughout her corporate career, Jessica trained hundreds of customer care, project management, and order processing professionals while supporting global team transitions across eight countries. Her work has always centered on helping people adapt to change, communicate effectively, make better decisions, and move forward with purpose.
As the founder of JC New Beginnings and host of We Are Women, Unapologetically, Jessica speaks on leadership communication, career reinvention, resilience, decision-making, AI and the future of work, and leading through change. Her approach is practical, honest, and rooted in real-world experience.
Speaking topics include:
-The Unapologetic Leader: Communicating with clarity, authority, and self-trust when the stakes are high
-The Human Advantage in the Age of AI: Staying relevant as technology changes the way we work
-Future-Proof Your Career: Navigating reinvention, role change, and what comes next
-Decision-Making Under Pressure: Making better decisions faster when the stakes are high
-Leading Through Change Without Losing Trust: Keeping people engaged during uncertainty
-Caregiving, Career, and Leadership: Navigating responsibility without losing yourself
Passion
Jessica is passionate about equipping people to navigate change with more clarity, confidence, and support.
Whether someone is stepping into leadership, rethinking their career, adapting to new technology, caregiving, or making decisions under pressure, Jessica believes people need space to think clearly, tools they can actually use, and guidance they can trust.
Through her speaking, coaching, training, and podcast, Jessica prepares professionals and leaders to trust their voice, make intentional decisions, and take ownership of what comes next.
One of the stories Jessica shares is from a time when she stepped into a role and asked her leader for guidance because she was not clear on what was expected. The response she received was, “You have friends who are project managers. Go figure it out.”
That moment stayed with her.
Jessica did figure it out, but the experience taught her an important leadership lesson: people can be capable and still need direction. They can be resourceful and still need support. And when leaders fail to provide clarity, they risk creating confusion, frustration, and silence instead of confidence and ownership.
Jessica uses this story to talk about self-trust, confidence, resilience, and leadership responsibility. It shaped the way she trains, coaches, and speaks today: equipping people with the tools, clarity, and support they need to make better decisions and move forward with confidence.
Origin Story
Jessica’s love for training and speaking started early.
At eight years old, she was already showing her mother’s employees how to use the cash register and answer the phone at her two gift shops. By age ten, she knew she wanted to travel the world and train people.
At sixteen, Jessica had the opportunity to meet Zig Ziglar in person and tell him she wanted to do what he did when she grew up. That moment stayed with her because it confirmed what she had already started to believe: she was meant to use her voice to teach, encourage, and equip others.
That early vision still guides her work today.
In today’s workplace, career reinvention is no longer optional. Roles change, industries shift, technology moves fast, and professionals have to be ready to adapt before they are forced to.
In this talk, Jessica Cumming guides professionals through the real questions that come with reinvention: What do I want next? What strengths do I need to trust? What am I carrying that no longer belongs in this next chapter? And how do I move forward without waiting for everything to feel certain?
Drawing from her experience in leadership, training, transition, and reinvention, Jessica equips audiences to rethink career growth with more honesty and intention. This talk is for professionals who are navigating role changes, leadership shifts, burnout, uncertainty, or the feeling that something needs to change but they are not sure where to begin.
Audience takeaways:
-Understand the difference between making a job move and navigating true career reinvention
-Recognize the signs that it may be time to reassess your direction
-Identify strengths, values, and experiences that can support your next chapter
-Learn how to make career decisions without waiting for perfect certainty
-Walk away with practical steps to move forward with more self-trust and intention
AI is changing how we work, lead, communicate, and make decisions. For many professionals, the pressure is not just learning new technology. It is figuring out how to stay valuable, visible, and prepared while the workplace keeps shifting.
In this talk, Jessica Cumming brings a practical, people-centered approach to the future of work. Drawing from nearly two decades in technology, training, and global team transitions, she helps audiences understand that staying relevant is not only about the tools they learn. It is also about how they think, communicate, adapt, and lead through change.
This talk equips professionals and leaders to look at AI with less fear and more intention, while strengthening the human skills that continue to matter in every workplace.
Audience takeaways:
-Understand how AI is changing work without getting stuck in fear or overwhelm
-Identify the human skills that remain essential as technology evolves
-Learn how adaptability, communication, and critical thinking support long-term relevance
-Recognize where resistance to change may be limiting growth or opportunity
-Walk away with practical ways to stay prepared, confident, and valuable in a changing workplace
Too many professionals wait to feel confident before they speak, lead, ask, challenge, or make a decision. But leadership does not wait for perfect confidence. It requires self-trust, intentional communication, and the ability to move forward when the pressure is real.
In this talk, Jessica Cumming introduces The Three Rules of the Unapologetic Mindset, a practical approach to building confidence, using your voice, and leading without abandoning yourself in the process. Through real stories and practical guidance, Jessica equips audiences to communicate with more authority, make stronger decisions, and trust themselves in the moments that matter most.
Audience takeaways:
-Learn how confidence is built through action, not waiting until fear disappears
-Recognize where silence, over-explaining, or self-doubt may be limiting your leadership
-Strengthen your ability to communicate clearly in high-pressure moments
-Understand why self-trust is essential to decision-making and leadership presence
-Walk away with practical ways to use your voice with more confidence and intention
One of the stories Jessica shares is from a time when she stepped into a role and asked her leader for guidance because she was not clear on what was expected. The response she received was, “You have friends who are project managers. Go figure it out.”
That moment stayed with her.
Jessica did figure it out, but the experience taught her an important leadership lesson: people can be capable and still need direction. They can be resourceful and still need support. And when leaders fail to provide clarity, they risk creating confusion, frustration, and silence instead of confidence and ownership.
Jessica uses this story to talk about self-trust, confidence, resilience, and leadership responsibility. It shaped the way she trains, coaches, and speaks today: equipping people with the tools, clarity, and support they need to make better decisions and move forward with confidence.
Origin Story
Jessica’s love for training and speaking started early.
At eight years old, she was already showing her mother’s employees how to use the cash register and answer the phone at her two gift shops. By age ten, she knew she wanted to travel the world and train people.
At sixteen, Jessica had the opportunity to meet Zig Ziglar in person and tell him she wanted to do what he did when she grew up. That moment stayed with her because it confirmed what she had already started to believe: she was meant to use her voice to teach, encourage, and equip others.
That early vision still guides her work today.
In today’s workplace, career reinvention is no longer optional. Roles change, industries shift, technology moves fast, and professionals have to be ready to adapt before they are forced to.
In this talk, Jessica Cumming guides professionals through the real questions that come with reinvention: What do I want next? What strengths do I need to trust? What am I carrying that no longer belongs in this next chapter? And how do I move forward without waiting for everything to feel certain?
Drawing from her experience in leadership, training, transition, and reinvention, Jessica equips audiences to rethink career growth with more honesty and intention. This talk is for professionals who are navigating role changes, leadership shifts, burnout, uncertainty, or the feeling that something needs to change but they are not sure where to begin.
Audience takeaways:
-Understand the difference between making a job move and navigating true career reinvention
-Recognize the signs that it may be time to reassess your direction
-Identify strengths, values, and experiences that can support your next chapter
-Learn how to make career decisions without waiting for perfect certainty
-Walk away with practical steps to move forward with more self-trust and intention
AI is changing how we work, lead, communicate, and make decisions. For many professionals, the pressure is not just learning new technology. It is figuring out how to stay valuable, visible, and prepared while the workplace keeps shifting.
In this talk, Jessica Cumming brings a practical, people-centered approach to the future of work. Drawing from nearly two decades in technology, training, and global team transitions, she helps audiences understand that staying relevant is not only about the tools they learn. It is also about how they think, communicate, adapt, and lead through change.
This talk equips professionals and leaders to look at AI with less fear and more intention, while strengthening the human skills that continue to matter in every workplace.
Audience takeaways:
-Understand how AI is changing work without getting stuck in fear or overwhelm
-Identify the human skills that remain essential as technology evolves
-Learn how adaptability, communication, and critical thinking support long-term relevance
-Recognize where resistance to change may be limiting growth or opportunity
-Walk away with practical ways to stay prepared, confident, and valuable in a changing workplace
Too many professionals wait to feel confident before they speak, lead, ask, challenge, or make a decision. But leadership does not wait for perfect confidence. It requires self-trust, intentional communication, and the ability to move forward when the pressure is real.
In this talk, Jessica Cumming introduces The Three Rules of the Unapologetic Mindset, a practical approach to building confidence, using your voice, and leading without abandoning yourself in the process. Through real stories and practical guidance, Jessica equips audiences to communicate with more authority, make stronger decisions, and trust themselves in the moments that matter most.
Audience takeaways:
-Learn how confidence is built through action, not waiting until fear disappears
-Recognize where silence, over-explaining, or self-doubt may be limiting your leadership
-Strengthen your ability to communicate clearly in high-pressure moments
-Understand why self-trust is essential to decision-making and leadership presence
-Walk away with practical ways to use your voice with more confidence and intention
