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Book Jessica Cumming To Speak

Bold. Transformational. Unapologetically Impactful.

Transforming How Leaders Navigate Change & Challenge

My Approach

I believe that in today's rapidly evolving workplace, leaders need more than motivation—they need actionable frameworks for navigating change, building confidence, and creating sustainable success.

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As someone who's led global teams and navigated significant career transitions myself, I bring real-world experience combined with evidence-based strategies to every keynote and workshop I deliver.

 

My mission is to bridge the gap between inspirational content and practical application, creating learning experiences that drive lasting results for professionals at all levels.

Signature Keynotes:

SHATTER THE GLASS CEILING WITHIN: Conquering Imposter Syndrome and Building Resilience

 

The truth is: Your qualifications don't hold you back—your doubts do.

I've seen firsthand how imposter syndrome affects approximately 70% of professionals at some point in their careers, with women and underrepresented groups experiencing it more intensely. In this keynote, I help participants identify self-limiting patterns and replace them with confidence-building strategies that create tangible results.

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You'll walk away with:

  • A practical framework for recognizing and redirecting self-sabotaging thoughts

  • The Resilience Roadmap I've developed for turning setbacks into growth opportunities

  • Specific techniques for owning your expertise and communicating with authority

 

Instead of just telling us to 'be confident,' she provided actual tools we could implement immediately." —Senior Manager, Technology Firm

 

Ideal for: Women's leadership initiatives, professional development programs, diversity and inclusion efforts

TURNING VISION INTO ACTION: Where Strategy Meets Execution

 The challenge: Most organizations are better at setting goals than achieving them.  In this session, I break down the science of achievement into a systematic approach that helps professionals close the gap between aspiration and accomplishment. Drawing from my experience coaching high-performing teams, I share the exact strategies that move people from intention to impact.

 

You'll walk away with:

  • A structured method for translating big-picture goals into actionable steps

  • Practical strategies for maintaining momentum when facing obstacles

  • Tools for aligning daily habits with long-term objectives

 

Ideal for: Leadership retreats, annual planning sessions, professional development conferences

THE POWER OF CHANGE: Navigating Transitions with Confidence

The reality: Change is inevitable; growth is optional.

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Having guided countless professionals through pivotal transitions, I've developed a powerful approach to help people not just survive change, but thrive through it. This keynote equips participants with the mindset and tools to maintain performance and wellbeing during periods of uncertainty.

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You'll walk away with:

  • Strategies I've personally used to maintain performance during major transitions

  • My framework for making confident decisions with incomplete information

  • Techniques for leading others through change with empathy and clarity

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Ideal for: Organizations navigating change, industry conferences, leadership development programs

Interactive Workshops

CONFIDENCE & EXECUTIVE PRESENCE: Communicating with Impact

In this immersive workshop, I help professionals develop an authentic leadership presence that commands attention and builds influence.

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Together, we'll focus on:

  • Developing confident communication patterns in high-stakes situations

  • Techniques I've taught executives for managing nerves and projecting authority

  • Strategies for ensuring your ideas are heard and valued

THE TRANSITION TOOLKIT: Strategic Career Navigation

This practical session equips you with my structured approach to navigating career changes with intention and confidence.

 

Together, we'll focus on:

  • Identifying when it's time for a professional pivot

  • Strategic approaches to networking and opportunity development

  • Creating a practical transition plan with clear milestones

FROM BURNOUT TO BOUNDARIES: Sustainable Success Strategies

I created this workshop after experiencing burnout firsthand and discovering what truly works to create sustainable success without sacrificing wellbeing.

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Together, we'll focus on:

  • Recognizing early warning signs of burnout

  • Implementing effective boundaries in various professional contexts

  • Designing a personalized sustainability plan for long-term success

Why I Connects with Audiences

I bring more than just theory to my presentations. Before becoming a speaker, I led global teams at Dell Technologies and navigated significant career transitions myself. I understand the challenges your team is facing because I've been there—from leading cross-functional initiatives to pivoting through career shifts, I’ve worked in high-stakes environments where results matter.

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As a Master Certified Professional Coach and Trainer, I’ve designed and facilitated training programs that transformed businesses and empowered leaders. I’ve worked with professionals across the globe, helping them build high-performing teams, improve operational efficiency, and navigate complex organizational changes. Whether it’s reducing onboarding time by 30% or enhancing customer satisfaction by 41%, I’ve been at the forefront of driving measurable improvements, and I bring that results-driven approach to every presentation.

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My focus is always on practical value over fluff—participants leave with strategies they can implement immediately, not just inspiration. I don’t just talk about leadership and transformation; I show how to apply these principles to create lasting change. With my experience in organizational development, change management, and process improvement, I deliver solutions that directly impact business outcomes.

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I believe in creating authentic connections with my audience by bringing my genuine insights and approachable style into every interaction. I’m not here to just fill the room with buzzwords; I’m here to empower attendees with the tools they need to succeed.

Most importantly, I customize every presentation to address the specific challenges and objectives of your organization or event. No cookie-cutter content—just tailored solutions that meet your unique needs. Whether it’s leadership development, navigating organizational change, or improving team performance, I ensure my content directly speaks to where your team is and where they want to go.

Let's Create Something Amazing Together

I'm passionate about creating learning experiences that transform how people approach their work and lives. Whether you're planning a corporate training event, leadership retreat, or industry conference, I'll work closely with you to design a session that meets your specific objectives and exceeds audience expectations.

Book Me for Your Event

I'M AVAILABLE FOR:

  • Corporate Leadership Events & Professional Development Programs

  • Industry & Professional Conferences

  • Women's Leadership Initiatives & Employee Resource Groups

  • Executive Team Sessions & Leadership Retreats​

Because navigating change is challenging—but you don't have to figure it out alone.

Current Availability: I accept a limited number of speaking engagements to ensure each receives my full attention. Contact me today to discuss your event needs and check availability.

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