Future of Work Speaker - Jessica D. Winder

Empowering Inclusive, Resilient, High-Performance Organizations

Is your organization preparing for the future? Are you looking for someone who can speak to your team or at your event about the future of work?

Meet Jessica D. Winder, an HR strategist, speaker, executive, and founder of Hidden Gem Career Coaching. She’s helped all kinds of companies future-proof their workplaces through inclusive leadership, reliable systems, and resilient team design.

Get in touch with Jessica to speak at your event today.

Book Jessica For Your Next Event

Why Engaging a Future of Work Speaker Matters Now

Work is being redefined in real time. It's important to build cultures and prep people for what’s next. From automation to hybrid flexibility, the businesses that thrive will be those that treat these changes as a strategic advantage. 

The Workplace Has Changed, Have You?

The way we work has changed fast. The office isn’t dead, but it’s not necessarily the center of work anymore.

Most workers don’t want to sit in an office five days a week anymore. A 2024 report shows 54% of people want to work fully remote. Another 41% want a hybrid work setting. Only 5% say they want to be on-site full time.

For U.S. employees with remote-capable jobs, Gallup reports that 52% now work hybrid, 27% are fully remote, and only 21% are fully on-site. But workers want even more flexibility.

This shift is about more than where people work. It’s about how they feel, and many don't feel great about work.

  • Bain & Company reported that 58% of workers say COVID made them rethink work-life balance. This means their values. Modern workers want flexibility, purpose, and real inclusion.

  • Global employee engagement dropped to 21% in 2024, according to Gallup. Managers took the biggest hit. It was only the second time in 12 years that engagement fell.

Companies that don’t evolve to meet these challenges are seeing higher turnover, lower morale, and weaker performance.

What's more is that the data is not even clear as to whether remote work boosts or hurts productivity. 

With such disparate outcomes, there's definitely more to the story. Perhaps how you manage remote workers and the policies you have for them make a big difference. Leading a remote or hybrid team today takes new thinking. What used to work won’t anymore.

Navigating AI-Related Changes

We’re in the middle of a tech shift that will change a lot about work. There will be winners, and there will be companies that fall behind.

Here’s what’s coming: 42% of tasks could be automated by 2027. That’s up from 34% today. Back in 2020, it was 33%. So the rise is real. At the same time, 23% of jobs may change. That includes 69 million new roles and 83 million jobs that may go away.

Workers feel it. A recent study shows 80% of U.S. employees could see at least 10% of their tasks impacted by AI. Nearly 1 in 5 might have 50% of their work changed. But it’s not all bad. AI can help too. Tools that handle admin work could save each worker 122 hours a year.

Jessica’s talks focus on the people behind the numbers. She helps leaders understand how to use AI to build stronger and more sustainable teams, not just faster ones. 

Her message is clear: this is a leadership test, not just a tech trend.

The ROI of Future-Ready Culture

Jessica doesn’t just give a great talk; she helps teams build systems that work. Her approach is practical. She helps leaders take real steps that make culture stronger and more ready for change.

And change is coming. Fast.

There’s a lot to prepare for. Nearly half of all workers, 44%, will need to learn new skills by 2027. Most companies aren’t ready. 

Add to that a shift in the age of the workforce, by 2030, 150 million jobs will be held by workers 55 and older. That means more training, more support, and smarter leadership.

Companies that invest in people now will win later. They’ll attract better talent, keep it longer, and stay strong through change.

Author of The Hidden Gem Within

Jessica’s book, The Hidden Gem Within, guides readers through how to spot and grow their natural strengths, even in work cultures that often overlook them. It’s written for anyone who’s felt undervalued, underrepresented, or stuck in roles that don’t reflect their worth.

The book has been praised for being honest, practical, and deeply human. It’s less about quick wins and more about building a career that actually fits who you are.

Featured Speaker at Top Events

Jessica has spoken at Transform three years in a row now. People appreciate her honest takes on what really happens at work.

Broad Industry Experience

Jessica has consulted and worked across a range of sectors, including:


  • Tech and Software

  • Retail

  • Biohazard Cleaning

  • Construction

  • Startups

  • Human resources

  • Legal

  • Healthcare

Meet Jessica D. Winder - Your Guide to the Future of Work

Let’s cover Jessica’s background and why she is the HR speaker who can help you solve problems.

Jessica’s Background in HR and DE&I Leadership

Jessica D. Winder has spent her career helping fast-growing companies scale while maintaining a people-first culture. She’s held executive HR roles in startups and mission-driven orgs where inclusion, impact, and business results had to work together, not compete.

She’s designed HR systems that support DE&I goals, sustainable work practices, and long-term company health. Leaders turn to her when they need someone who can balance performance with compassion and build structures that last.

Jessica’s initiatives have cut turnover by up to 25% at companies.

Founder of Hidden Gem Career Coaching

Jessica runs her own consultancy, Hidden Gem Career Coaching. She works with individuals to help them achieve their career dreams and with companies to make sure growth is possible.

She brings a two-sided lens: coaching and HR. This helps her speak to both sides of the table. Her talks reflect that.

Book Jessica For Your Next Event

Keynote Topics That Guide Organizations Forward

Now let's review some topics Jessica can discuss during a Future of Work Speech or event. Keep in mind that you can customize her talk based on the challenges you are facing.

Future of Work & Human-Centered Leadership

Human-centered leadership puts people first. It means listening, building trust, and leading with care, not just control or fear. Jessica teaches leaders how to shift from top-down rules to team-first results. 

She shares how this approach helps teams work better, feel safer, and stay longer. Her talk blends real DEI strategy with leadership skills that help managers connect during hard shifts.

The Human Edge in the Age of AI

As AI tools take on more tasks, Jessica helps leaders protect what makes people special. She talks about real ways to use AI while keeping teams creative, strong, and ethical. This includes using tech to free up time and using that time to build trust and spark ideas.

Designing Inclusive, Sustainable Hybrid Workplaces

Hybrid work isn’t just about who shows up when; it’s about who feels seen. Jessica helps leaders move past meeting schedules to fix deeper issues like burnout, fairness, and culture gaps. She shares tools like fair meeting design and ways to help remote workers stay visible. Companies that fail to improve hybrid setups risk losing good people.

Pay Equity & Career Sustainability

Jessica talks about pay in a way that feels honest and useful. She helps leaders check their systems for gaps and bias, and build growth paths people trust. Her talk ties pay and career design into DEI, culture, and team health. The message: fairness drives results.

Empowering Teams Through Values-Based Leadership

Jessica teaches how to bring values into real choices, like giving feedback, setting goals, and deciding who gets heard. Values-based leadership means knowing what your team stands for and sticking to it. The focus is on courage and care, so teams know where they’re going and feel safe getting there.

What Sets Jessica Apart from Other Speakers

Now, let’s discuss what makes Jessica different from other HR speakers.

Real-World Solutions from Real Experience

Jessica isn’t just a coach. She’s led HR teams through fast growth, hard times, and full reorgs. She knows what works in practice, not just theory. Most importantly, she knows what works when things get messy. Jessica has sat at the decision table and brings grounded, usable insight to every talk.

Tools You Can Use Immediately - Not Just Inspiration

Jessica’s sessions often come with usable tools: checklists, frameworks, templates, etc. These aren’t ideas for “someday,” they’re action plans for Monday. Her goal is always to help teams act fast and grow smarter.

Honest, Engaging, Story-Driven Style

Forget buzzwords. Jessica shares real-world stories that make people lean in and reflect. Her sessions are designed to feel human, because they are. She speaks with humor, warmth, and honesty that connects with leaders at every level.

At the Intersection of DE&I, Well-Being, and Performance

Where most speakers stick to one area, Jessica helps to connect the dots. She shows how inclusion and well-being drive team results. Her approach helps companies take care of people and meet goals with clarity and confidence.

Real-World Impact: Outcomes You Can Expect

These are some of the real goals Jessica can help you attain.

Improved Retention and Engagement Metrics

Jessica’s work drives results. Her keynotes don’t just sound good; they lead to measurable action and stronger performance. Jessica’s work leads to real numbers: lower turnover, faster ramp-ups, and longer team tenure.

Jessica helps reduce churn and spark momentum. Her tools help teams fix the root issues behind burnout and turnover. Managers walk away with better systems, not just ideas.

Stronger Culture of Belonging and Accountability

She helps build cultures where people feel safe to speak up and are responsible for outcomes. Jessica teaches how to mix empathy with standards, creating teams that trust each other and deliver.

Leadership Buy-In on Future-Focused Initiatives

Jessica helps HR and DEI teams get C-suite support for bold moves. Jessica helps people leaders make the business case for inclusion, well-being, and innovation.

Frameworks for Adaptability, Inclusion, and Innovation

Jessica brings science-backed, field-tested tools that help orgs move fast and stay grounded. From inclusive decisions to innovation sprints, her frameworks work across teams and get results that matter.

She brings tested tools that help teams adapt fast and stay grounded. From value-alignment workshops to equity-centered planning models, her frameworks are ready to plug into real workflows.

Book Jessica For Your Next Event

Media, Thought Leadership & Featured Collaborations

Author: The Hidden Gem Within

As mentioned above, Jessica is the author of The Hidden Gem Within. This book helps overlooked professionals rediscover their strengths and build careers that align with their values. It’s a guide for anyone who’s ever felt underestimated at work and wants to change that.

Featured On: HRchat, Made Leader, FutureSolve & More

Here are some podcast appearances Jessica has made:

80K+ Followers on LinkedIn - Active HR Thought Leader

With more than 80,000 LinkedIn followers, Jessica regularly posts practical, people-first leadership advice.

Book Jessica For Your Next Event

Book Jessica for Your Next Event

Thinking about working with Jessica for your next event? Here's some important info for you.

H3: Customized Keynotes to Match Your Audience

Jessica makes sure her talks feel built just for your team. She never repeats the same speech twice. Before the event, she meets with you to shape the message to your people, your goals, and your culture. She offers flexible formats like 30-, 60-, or 90-minute keynotes (virtual or in-person), and always holds a prep call to align on tone, goals, and team dynamics.

H3: Contact Information and Booking Details

Would you like to bring Jessica to your next event or have her train your team? Reaching out is easy. To get started, get in touch with her by filling out this form.

Contact Us