Employee Retention Speaker - Jessica D. Winder

Helping Organizations Keep Top Talent Through Inclusive, Caring Leadership

When teams struggle to keep great people, it costs time, money, and momentum. That’s where Jessica D. Winder steps in to teach the skills you need to cut those costs.

As a workplace culture professional, Jessica helps organizations hold onto their best talent through talks that connect, inspire, and create lasting change.

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Why Hire an Employee Retention Speaker?

Let’s review how a speaker who leads an exciting discussion about how to improve employee retention can be helpful to your company or event.

The Cost of Turnover and Low Engagement

Employee turnover isn’t just a pain. It’s a drain on resources; a slow, steady, and costly one.

The numbers behind employee turnover are blunt:

But the money isn’t even the hardest part. When a good employee quits, you also lose:

  • Experience

  • Time

  • Energy

  • And maybe the trust of the people who stay behind.


So what’s really going wrong? If you ask around the organization, you’ll hear it:

  • “I don’t feel heard.”

  • “My work doesn’t matter.”

  • “My manager’s checked out.”

  • “We do so much unnecessary work and no one cares.”

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Retention Starts With Leadership, Culture, and Listening

Employee retention doesn’t necessarily begin with salary or perks; it often starts with company culture. Leaders who know how to listen, support, and connect with their teams build loyalty that lasts.

Jessica can help you tackle the root causes of attrition. She helps companies recognize that employees don’t always leave companies; they often leave managers. Her approach is people-first, helping leaders develop emotional intelligence, humility, and trust-building skills.

The Business Case: Engagement = Retention = Results

Jessica often walks clients through a simple yet powerful equation:

Engaged Employees → Higher Performance → Greater Retention → ROI

When companies invest in employee experience, the results follow. 

  • According to PressGaney, Hospitals with the highest nurse engagement levels see 5.6% better performance. They also save roughly $313,000 in annual turnover costs for every 100 nurses who stay.

  • A Harvard Business Review and Quantum Workplace study revealed that 81% of business leaders believe highly engaged employees perform better. Only 37% prioritize engagement in their own organizations, though.

An outside speaker like Jessica helps teams and leaders adopt change faster. Her credibility and clarity can lead to quick buy-in, even from skeptical executives.

Meet Jessica D. Winder - Employee Retention Speaker

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

Who Is Jessica

Jessica D. Winder is the Senior Vice President of People at CoLab Software and the founder of Hidden Gem Career Coaching. 

She has spent her career helping high-growth startups and mission-driven companies scale their people systems without losing their soul. Jessica’s talks go beyond buzzwords. She focuses on what leadership, inclusion, and engagement actually look like in daily practice. 

Her goal is simple: help workplaces run better and feel better. 

Jessica has spoken at Transform for three consecutive years, where she’s known for cutting through the noise and being honest about work.

Jessica’s Track Record in Employee Retention

Jessica brings a tested playbook to retention challenges. 

  • She built and led a leadership development initiative that resulted in a 40% increase in internal promotions, improving morale and closing advancement gaps. 

  • Jessica also implemented a compensation floor, which cut turnover by 25% and signaled a stronger investment in people. 


Her strategies blend fairness with impact. Jessica can help guide your organization to get results like these too!

Broad Industry Experience

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

  • Tech and Software

  • Startups

  • Human resources

  • Legal

  • Healthcare

  • Retail

  • Biohazard Cleaning

  • Construction

She bridges HR systems with culture strategy, often partnering with DEI officers, people operations leaders, and executive coaches. Whether designing a leadership summit or launching a new Employee Resource Group (ERG), she brings clarity and compassion to the process.

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Keynote Topics That Improve Retention

Let’s review a sample of topics Jessica can cover during her speeches. This is by no means a complete list. If you have other specifics you want her to cover, then get in touch and let her know!

Leading With Care: How Inclusive Leaders Inspire Loyalty

Leadership often matters more than perks. People usually stay for leaders who treat them like people.

Jessica shows that caring leadership comes down to:

  • Empathy: leading with listening

  • Boundaries: protecting time and energy

  • Visibility: being seen and seeing others

These traits make teams feel safe. That safety turns into trust, and trust keeps people on board. On this topic, Jessica can share:

  • What genuine empathy looks like in daily leadership

  • How to respect limits without losing impact

  • Why visible leadership builds deep, lasting loyalty

It’s not just inspiring. It’s actionable. Teams leave with a new model, and leaders leave ready to use it.

Building a Culture of Listening, Recognition, and Belonging

Listening builds trust, and trust keeps teams together. When leaders stop to listen, people open up. That creates psychological safety, a key part of trust. Teams need to know their thoughts won’t just be heard, but acted on.

Jessica gives leaders tools to:

  • Show they’re really listening

  • Respond with care, not just answers

  • Make listening part of normal check-ins and team meetings

Next comes recognition. And this isn’t one-size-fits-all. Jessica teaches how to:

  • Praise staff in ways that feel real

  • Respect employees with private, thoughtful notes

  • Build habits of regular appreciation

When people feel heard and valued, they stay. It’s that simple, and that powerful.

The Retention Ripple Effect

“Employee voice” is more than a buzzword. It’s a clear signal: people feel safe, valued, and heard.

Jessica explains that when workers believe their ideas matter, they put more effort into their job. It boosts morale, fuels innovation, and lowers the risk of quiet quitting or sudden exits.

Jessica helps leaders:

  • Listen with intent

  • Reflect on feedback without ego

  • Take action, even when it’s hard

She builds systems that make this easy to sustain:

  • She shares proven ways to bring this to life:

  • Use pulse surveys to track and respond to employee needs

  • Involve ERG leaders in shaping events, policy, and training

  • Close the feedback loop by showing what changed and who helped

Letting people speak isn’t enough. Showing you care about what they said? That’s what keeps them.

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What Sets Jessica Apart From Other Retention Speakers

Let’s review why Jessica’s approach makes her the right employee retention speaker for your organization.

Backed by Research, Delivered With Heart

Jessica brings more than research. She brings results. Her approach is grounded in trusted studies that show equity and inclusion improve team performance, reduce turnover, and foster lasting trust.

But what really sets her apart? Her delivery. Jessica brings heart to complex topics. She speaks from experience, with the kind of cultural fluency many leaders lack. Her style is clear, grounded, and real, not corporate fluff.

Where others offer buzzwords, she offers tools. And where others stay safe, she speaks her mind in a way that moves people.

Jessica is a highly engaging speaker and not a corporate robot who will make your team’s eyes glaze over.

Interactive Formats That Leave a Lasting Impact

Jessica’s sessions are built for action, not just applause.

She often includes:

  • Journaling prompts that help leaders internalize new ideas

  • Structured conversation pairs to share stories and apply insights

  • Group dialogues to name what's working and what’s not

This kind of engagement leads to better recall and faster action after the event. Organizers often hear, “We’re still talking about it weeks later.”

She adjusts her approach for groups of all sizes, from tight-knit teams to packed ballrooms. Whether it’s 20 people at a retreat or 1,000 at a company-wide summit, Jessica adapts to fit the room and makes it feel personal.

Media, Books, and Thought Leadership

Here are some places where you can view more of Jessica’s work.

Author of “The Hidden Gem Within”

Jessica is the author of “The Hidden Gem Within: Discovering Your Strengths & Talents for a Fulfilling Career.”

In “The Hidden Gem Within,” Jessica invites readers to rediscover their purpose through the lens of strengths-based growth. Blending storytelling with actionable steps, the book empowers professionals, especially those who feel unseen or undervalued, to build careers rooted in authenticity, joy, and self-defined success.

Podcast and Webinar Guest on Retention, Culture, and Listening

Here are some podcast appearances Jessica has made:

Thought Leadership on LinkedIn

Follow Jessica on LinkedIn, where she regularly posts insights to her 80,000 followers.

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Booking Jessica D. Winder as Your Retention Speaker

Here is some vital information if you're considering booking Jessica for your event!

Event Formats

Jessica’s speaking formats are designed for flexibility and depth. Here are some examples:

  • Keynotes (30–60 mins): Ideal for conferences or kickoff moments

  • Workshops (90 mins): Focused time to dive into tactics

  • Retreat sessions (half-day): Great for leadership or team growth

She offers in-person and virtual talks. Virtual sessions include a comprehensive tech setup, including lighting, audio, and platform testing with your team.

Tailored Messaging

No two events are the same, and Jessica gets that. She custom-prepares each talk and can meet with your team to research your organization in advance.

Availability, Rates, and Contact Info

Jessica’s speaking fees can range depending on what you'd like her to do.

Although each engagement is tailored to the specific audience, goals, and format, special pricing might be available for your organization. 


Interested in bringing Jessica to your event? To get started, get in touch with her by filling out this form.