Lisa Haynes

Chief Reinvention Wingwoman at Haynes Executive Solutions, LLC

Member since July 2024

Leadership

Education: Bentley University - Boston University
Tampa, FL, USA

Biography

Lisa J. Haynes is a speaker, board member, and dual-certified executive and retirement coach who helps high-achieving professionals—especially senior leaders and executives—navigate reinvention.

She brings more than 35 years of executive leadership experience across organizations including Fannie Mae, John Hancock, and the Mortgage Bankers Association, where she served as Chief Financial Officer and Chief Diversity & Inclusion Officer. A CPA and Qualified Financial Expert, Lisa has led through complex financial and regulatory environments, including the $6.3 billion financial restatement at Fannie Mae and SEC reporting at John Hancock following demutualization.

Today, Lisa focuses on what most people miss—the non-financial side of reinvention. While many professionals prepare financially for transition, few are prepared for the identity shift, loss of structure, and quiet uncertainty that often follow a successful career.

Known as the Chief Reinvention Wingwoman, Lisa helps individuals and organizations move forward with clarity, confidence, and purpose. Her work is grounded in her KILLIN’ IT and GOT THIS frameworks, which provide practical, real-world guidance for navigating change and stepping fully into what’s next.

An engaging, down-to-earth speaker, Lisa blends humor, vulnerability, and practical insight to connect with audiences. She speaks on reinvention, late-career transitions, and leadership beyond traditional roles.

Lisa serves on the Advisory Board of Porte Management Agency and as a board director for The Bridge Solution, bringing financial expertise, governance insight, and executive leadership experience.

Passion

At the core of Lisa’s work is a deep passion for helping people reach their full potential—in their careers, finances, and personal lives. She believes leadership isn’t about titles, but about influence, empathy, and showing up with authenticity. Whether she’s coaching emerging leaders, guiding professionals through retirement, or advising on strategic transitions, Lisa is most energized when she sees someone step into their power and lead with clarity and confidence.

She’s especially passionate about supporting people through life’s big transitions—stepping into a new role, reimagining life after retirement, or designing a fulfilling second act. These crossroads can feel overwhelming, but Lisa sees them as powerful moments for reinvention. She’s driven by the belief that everyone—especially women and underrepresented voices—deserves the tools, support, and space to lead on their own terms.

Best Story

I want to share a story about being teachable and coachable—and the power of a strong support circle.

It was a board meeting to review the preliminary budget, always a high-stakes moment. As CFO, I was responsible for presenting the draft budget to the board. Even though it was meant for feedback, the questions started rolling in—fast and pointed. For 45 minutes, I fielded a steady stream of inquiries, and one board member in particular came at me hard. It turned into a tense, back-and-forth exchange that had the whole room on edge.

Then, in the middle of it all, a board member and mentor sitting beside me leaned over and quietly whispered, “Don’t get defensive.” That simple phrase snapped me out of the spiral. I took a breath. I shifted my tone. And just like that, the energy in the room changed.

Here’s what I learned: Being teachable means staying open—even in the heat of the moment. That one whisper reminded me that growth often comes from the uncomfortable moments, and that real-time feedback is a gift, not a threat. But maybe the bigger lesson was this—having a circle of support matters. Sometimes, the quietest voice beside you is what helps you rise with grace under pressure.

Origin Story

My story begins long before boardrooms and balance sheets — it starts on a yellow school bus. As a child, I participated in a voluntary busing program, commuting over an hour each day between two very different worlds: the neighborhood where I lived and the community where I went to school. That early experience taught me resilience, adaptability, and how to navigate spaces where I often stood out — not by blending in, but by being exceptionally prepared and relentlessly focused. It’s also where I began finding my voice — learning to speak up, advocate for myself, and bridge cultural divides with clarity and confidence.

That mindset carried me into the finance and accounting industry, where I built a 30+ year career grounded in leadership, performance, and purpose. From analyst roles to the C-suite, I led with intention, shaped teams, and left a legacy that was about more than numbers — it was about impact. Along the way, I learned some powerful truths:

- People matter most
- Leaders must be accountable and act as the shield for their teams
- True success means bringing others along with you

Life transitions will come, but it’s how we navigate them that defines our growth

That early voice only grew stronger. Whether presenting in the boardroom or mentoring behind the scenes, I became known for communicating with both clarity and conviction. Speaking became a natural extension of my leadership.

After decades of success in corporate leadership, I chose to retire on a high note and redefine what the next chapter could look like. Today, I coach, speak, and create tools to help others build lives of purpose and possibility. Retirement isn’t the end of the story — for me, it’s the beginning of a bold second act and a continued commitment to leaving a legacy and making an impact.

Your updated story now weaves in how you found your voice early and how that evolved into your speaking journey. Let me know if you'd like to shape this further into a speaker one-sheet or a pitch for an event.

Example Talks

You’ve Got This! Reinvention with Intention

Summary

Reinvention doesn’t require starting over — it requires starting where you are. In this uplifting and practical talk, Lisa helps audiences navigate change with clarity, confidence, and intention. Whether transitioning into retirement, pivoting careers, or entering a new season of life, participants gain reassurance and perspective that they are more prepared for what’s next than they think.

Ideal Audience

  • Individuals navigating career or life transitions

  • Professionals approaching retirement or exploring what’s next

  • Women and men experiencing identity or purpose shifts

  • Employees facing role changes, burnout, or uncertainty

  • Organizations and community groups focused on resilience and personal growth

Participants will learn how to:

Learning Objectives

  • Understand why change feels uncomfortable — even when it’s desired

  • Release limiting beliefs tied to past roles or identities

  • Approach reinvention with confidence instead of fear

  • Take intentional, manageable steps forward during uncertain times

Key Takeaways

  • Reassurance that reinvention is normal and achievable

  • Tools for navigating uncertainty with greater confidence

  • A mindset shift from “What now?” to “I’ve got this”

  • Practical strategies for moving forward without needing all the answers

RETIRED AND KILLIN’ IT: Designing a Fulfilling Next Chapter

Summary

Retirement isn’t the end of the story — it’s the beginning of a new chapter. This talk challenges outdated ideas about retirement and invites audiences to intentionally design what comes next. With practical insight and real-life perspective, participants rethink success beyond work and explore how to create a next chapter that feels meaningful, connected, and deeply fulfilling.

Ideal Audience

  • Individuals approaching or recently in retirement

  • Professionals exploring life beyond full-time work

  • Late-career employees preparing for transition

  • Associations, alumni groups, and community organizations

  • Conferences focused on retirement, reinvention, or life planning

Participants will learn how to:

Learning Objectives

  • Reframe retirement as a meaningful life transition, not an ending

  • Identify what fulfillment and success look like beyond work

  • Recognize common challenges that arise after leaving the workforce

  • Approach retirement with intention rather than uncertainty

Key Takeaways

  • A fresh perspective on life after work

  • Greater clarity around purpose and fulfillment in retirement

  • Encouragement to intentionally design the next chapter

  • Confidence that retirement can be meaningful and rewarding

THE HIDDEN WORKFORCE RISK: Why Late-Career Employees Stay Longer Than Planned

Summary

Many organizations face delayed retirements, stalled succession planning, and workforce bottlenecks without fully understanding why. While financial readiness is often addressed, the non-financial side of retirement is largely overlooked. This session explores how identity, purpose, and emotional readiness influence when employees choose to exit — and how organizations can better support purposeful, timely transitions that benefit both employees and the business.

Ideal Audience

  • HR leaders and people managers

  • Talent management and workforce planning teams

  • Succession planning and employee experience leaders

  • Benefits and total rewards professionals

  • Organizations with a large late-career or retirement-eligible workforce

Participants will learn how to:

Learning Objectives

  • Understand why late-career employees delay retirement beyond financial readiness

  • Identify non-financial factors influencing retirement timing

  • Recognize how delayed transitions impact workforce planning and engagement

  • Reframe retirement readiness as a human-centered workforce strategy

Key Takeaways

  • Insight into the hidden drivers behind delayed retirement

  • A clearer lens on late-career workforce dynamics

  • Practical considerations for supporting purposeful transitions

  • Greater confidence in addressing retirement transitions strategically

Life Gets Gooder: Designing a Joyful Next Chapter

Life after work doesn’t have to feel smaller — it can feel richer, lighter, and more joyful. In this inspiring keynote, Lisa explores how to design a next chapter that reflects who you are today, not who you used to be. Through storytelling, reflection, and practical insight, she helps audiences reconnect with joy, purpose, and possibility, reminding them that the best chapters of life are often the ones we intentionally create.

Ideal Audience

  • Individuals approaching or already in retirement

  • Professionals exploring life beyond full-time work

  • Women’s conferences and community groups

  • Faith-based and purpose-driven organizations

  • Audiences seeking inspiration, clarity, and renewed optimism

Learning Objectives

Participants will learn how to:

  • Shift their mindset from loss to possibility in retirement

  • Identify what brings joy and meaning in their next chapter

  • Release outdated definitions of success

  • Design a life that feels intentional, balanced, and fulfilling

Key Takeaways

  • A fresh, hopeful perspective on life after work

  • Permission to prioritize joy, purpose, and well-being

  • Inspiration to intentionally design the next chapter

  • A renewed belief that life really does get gooder

Topics/Keywords

diversity in the workplace women in finance womens leadership team leadership authentic self finding your voice mentoring culture women in the workplace women and leadership people of color moving beyond your comfort zone chief financial officer finance dei financial education executive coaching retirement retirement planning retirement transition authentic leadership managing transitions next chapters leadership executive coacing retirement coaching leadership coaching finance leaders cfo advisor personal finance networking for introverts introverted leadership accounting accounting and finance minority and african american women black women women human resources networking career transition empowering women transition leadership development career transitions workplace engagement workplace reinvention aging senior healthcare professional development baby boomers workforce hr retirement services retirement plan financial advisor

Featured Video

I am willing to travel more than 100 miles
Yes
Everything is negotiable

Best Story

I want to share a story about being teachable and coachable—and the power of a strong support circle.

It was a board meeting to review the preliminary budget, always a high-stakes moment. As CFO, I was responsible for presenting the draft budget to the board. Even though it was meant for feedback, the questions started rolling in—fast and pointed. For 45 minutes, I fielded a steady stream of inquiries, and one board member in particular came at me hard. It turned into a tense, back-and-forth exchange that had the whole room on edge.

Then, in the middle of it all, a board member and mentor sitting beside me leaned over and quietly whispered, “Don’t get defensive.” That simple phrase snapped me out of the spiral. I took a breath. I shifted my tone. And just like that, the energy in the room changed.

Here’s what I learned: Being teachable means staying open—even in the heat of the moment. That one whisper reminded me that growth often comes from the uncomfortable moments, and that real-time feedback is a gift, not a threat. But maybe the bigger lesson was this—having a circle of support matters. Sometimes, the quietest voice beside you is what helps you rise with grace under pressure.

Origin Story

My story begins long before boardrooms and balance sheets — it starts on a yellow school bus. As a child, I participated in a voluntary busing program, commuting over an hour each day between two very different worlds: the neighborhood where I lived and the community where I went to school. That early experience taught me resilience, adaptability, and how to navigate spaces where I often stood out — not by blending in, but by being exceptionally prepared and relentlessly focused. It’s also where I began finding my voice — learning to speak up, advocate for myself, and bridge cultural divides with clarity and confidence.

That mindset carried me into the finance and accounting industry, where I built a 30+ year career grounded in leadership, performance, and purpose. From analyst roles to the C-suite, I led with intention, shaped teams, and left a legacy that was about more than numbers — it was about impact. Along the way, I learned some powerful truths:

- People matter most
- Leaders must be accountable and act as the shield for their teams
- True success means bringing others along with you

Life transitions will come, but it’s how we navigate them that defines our growth

That early voice only grew stronger. Whether presenting in the boardroom or mentoring behind the scenes, I became known for communicating with both clarity and conviction. Speaking became a natural extension of my leadership.

After decades of success in corporate leadership, I chose to retire on a high note and redefine what the next chapter could look like. Today, I coach, speak, and create tools to help others build lives of purpose and possibility. Retirement isn’t the end of the story — for me, it’s the beginning of a bold second act and a continued commitment to leaving a legacy and making an impact.

Your updated story now weaves in how you found your voice early and how that evolved into your speaking journey. Let me know if you'd like to shape this further into a speaker one-sheet or a pitch for an event.

I am willing to travel more than 100 miles
Yes
Everything is negotiable

Example Talks

You’ve Got This! Reinvention with Intention

Summary

Reinvention doesn’t require starting over — it requires starting where you are. In this uplifting and practical talk, Lisa helps audiences navigate change with clarity, confidence, and intention. Whether transitioning into retirement, pivoting careers, or entering a new season of life, participants gain reassurance and perspective that they are more prepared for what’s next than they think.

Ideal Audience

  • Individuals navigating career or life transitions

  • Professionals approaching retirement or exploring what’s next

  • Women and men experiencing identity or purpose shifts

  • Employees facing role changes, burnout, or uncertainty

  • Organizations and community groups focused on resilience and personal growth

Participants will learn how to:

Learning Objectives

  • Understand why change feels uncomfortable — even when it’s desired

  • Release limiting beliefs tied to past roles or identities

  • Approach reinvention with confidence instead of fear

  • Take intentional, manageable steps forward during uncertain times

Key Takeaways

  • Reassurance that reinvention is normal and achievable

  • Tools for navigating uncertainty with greater confidence

  • A mindset shift from “What now?” to “I’ve got this”

  • Practical strategies for moving forward without needing all the answers

RETIRED AND KILLIN’ IT: Designing a Fulfilling Next Chapter

Summary

Retirement isn’t the end of the story — it’s the beginning of a new chapter. This talk challenges outdated ideas about retirement and invites audiences to intentionally design what comes next. With practical insight and real-life perspective, participants rethink success beyond work and explore how to create a next chapter that feels meaningful, connected, and deeply fulfilling.

Ideal Audience

  • Individuals approaching or recently in retirement

  • Professionals exploring life beyond full-time work

  • Late-career employees preparing for transition

  • Associations, alumni groups, and community organizations

  • Conferences focused on retirement, reinvention, or life planning

Participants will learn how to:

Learning Objectives

  • Reframe retirement as a meaningful life transition, not an ending

  • Identify what fulfillment and success look like beyond work

  • Recognize common challenges that arise after leaving the workforce

  • Approach retirement with intention rather than uncertainty

Key Takeaways

  • A fresh perspective on life after work

  • Greater clarity around purpose and fulfillment in retirement

  • Encouragement to intentionally design the next chapter

  • Confidence that retirement can be meaningful and rewarding

THE HIDDEN WORKFORCE RISK: Why Late-Career Employees Stay Longer Than Planned

Summary

Many organizations face delayed retirements, stalled succession planning, and workforce bottlenecks without fully understanding why. While financial readiness is often addressed, the non-financial side of retirement is largely overlooked. This session explores how identity, purpose, and emotional readiness influence when employees choose to exit — and how organizations can better support purposeful, timely transitions that benefit both employees and the business.

Ideal Audience

  • HR leaders and people managers

  • Talent management and workforce planning teams

  • Succession planning and employee experience leaders

  • Benefits and total rewards professionals

  • Organizations with a large late-career or retirement-eligible workforce

Participants will learn how to:

Learning Objectives

  • Understand why late-career employees delay retirement beyond financial readiness

  • Identify non-financial factors influencing retirement timing

  • Recognize how delayed transitions impact workforce planning and engagement

  • Reframe retirement readiness as a human-centered workforce strategy

Key Takeaways

  • Insight into the hidden drivers behind delayed retirement

  • A clearer lens on late-career workforce dynamics

  • Practical considerations for supporting purposeful transitions

  • Greater confidence in addressing retirement transitions strategically

Life Gets Gooder: Designing a Joyful Next Chapter

Life after work doesn’t have to feel smaller — it can feel richer, lighter, and more joyful. In this inspiring keynote, Lisa explores how to design a next chapter that reflects who you are today, not who you used to be. Through storytelling, reflection, and practical insight, she helps audiences reconnect with joy, purpose, and possibility, reminding them that the best chapters of life are often the ones we intentionally create.

Ideal Audience

  • Individuals approaching or already in retirement

  • Professionals exploring life beyond full-time work

  • Women’s conferences and community groups

  • Faith-based and purpose-driven organizations

  • Audiences seeking inspiration, clarity, and renewed optimism

Learning Objectives

Participants will learn how to:

  • Shift their mindset from loss to possibility in retirement

  • Identify what brings joy and meaning in their next chapter

  • Release outdated definitions of success

  • Design a life that feels intentional, balanced, and fulfilling

Key Takeaways

  • A fresh, hopeful perspective on life after work

  • Permission to prioritize joy, purpose, and well-being

  • Inspiration to intentionally design the next chapter

  • A renewed belief that life really does get gooder

Topics/Keywords

diversity in the workplace women in finance womens leadership team leadership authentic self finding your voice mentoring culture women in the workplace women and leadership people of color moving beyond your comfort zone chief financial officer finance dei financial education executive coaching retirement retirement planning retirement transition authentic leadership managing transitions next chapters leadership executive coacing retirement coaching leadership coaching finance leaders cfo advisor personal finance networking for introverts introverted leadership accounting accounting and finance minority and african american women black women women human resources networking career transition empowering women transition leadership development career transitions workplace engagement workplace reinvention aging senior healthcare professional development baby boomers workforce hr retirement services retirement plan financial advisor