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A NEW CAREER ISN’T JUST POSSIBLE
IT’S WAITING FOR YOU
ATTEND LIVE FOR A CHANCE TO WIN
1:1 COACHING + CAREER RESOURCES
HEAR WHAT TEACHERS HAD TO SAY ABOUT LAST YEAR’S SUMMIT

INSPIRING SPEAKERS TO GUIDE YOUR CAREER JOURNEY
Lisa Harding
Certified Career Coach
Former Edtech CEO
Teacher Career Transition Academy CEO
Rachel Dunbar
Transitioning Educator
Samara Birkey
Renee Jackson
Denise Treadway
Gina Arnello
Nate Ditterline
Chelsea Aviret
HEAR WHAT TEACHERS HAD TO SAY ABOUT THE SUMMIT
EVENT SCHEDULE
One day. Four sessions. Tons of clarity.
Here’s a sneak peek at what your day will look like. Expect a mix of inspiration, real-world advice, and actionable strategies — all designed to help you confidently transition into a new career.
Schedule is tentative. Check back often for updates and final speaker announcements!
All times listed in Eastern Time, USA.
🚀 9:45 AM – Morning Kickoff
Prizes, Prep, and What to Expect
Welcome Session with Prizes, Prep, and What to Expect.
🕙 10:00 AM – Session 1: Keynote
This Changes Everything: A New Way to Think About Leaving the Classroom
with Lisa Harding
If you’ve been stuck in career confusion—applying for
jobs you’re not even sure you want, second-guessing your skills, or wondering
if you’ll ever feel confident again—you are not alone.
In this keynote session, Lisa Harding, co-founder of the
Teacher Career Transition Academy, shares what she’s learned from working with
thousands of teachers navigating life beyond the classroom. You’ll get a
powerful, honest look at what it really takes to change careers—and why
so many teachers stall out along the way.
More than inspiration, this session offers clarity: a new
way to understand where you are, what’s holding you back, and how to move
forward with purpose.
This session sets the tone for the entire day—and will help you get the most
out of every panel, conversation, and opportunity that follows.
💡 Key Takeaways:
• A clear breakdown of what career change actually looks like for teachers (and why it’s not your fault if it feels hard)
• The hidden stages of a successful transition—and how to recognize where you are right now
• What’s keeping so many teachers stuck (hint: it’s not just your resume)
• How to finally build momentum—without going back to school, starting over, or guessing your way forward
🕚 11:00 AM – Session 2: Panel Discussion
From Classroom to Career: How Real Teachers Made the Transition
Featuring: Denise Treadway, Gina Arnello & Nate Ditterline
You’ve set up your LinkedIn profile… now what?
If you’re feeling stuck about what to post—or nervous about showing up publicly while you’re still in the classroom—this session is for you.
Join us to learn exactly how to use LinkedIn as a visibility tool without needing to announce you’re leaving teaching. You’ll discover how to engage intentionally, share content that builds your credibility, and get noticed by recruiters and career changers alike—even if you don’t know your next step yet.
In this session, you'll learn:
• What types of posts are safe and effective while career exploring
• How to comment with purpose to boost your visibility
• Why engagement matters—and how it gets you seen by the right people
• Easy post ideas (even if you're nervous or stuck!)
• Common LinkedIn posting mistakes to avoid as a career changer
Whether you’re actively job searching or just starting to explore your options, this session will give you the confidence and clarity to start showing up on LinkedIn with intention.
🕚 12:00 PM – Session 3: Hiring Manager
Hiring Trends and Jobs You Can Apply to Right Now
with Chelsea Aviret from Skip's Job Board
Ever wonder how former teachers actually land jobs outside the classroom—and what hiring managers are really looking for?
In this
behind-the-scenes panel, four former teachers turned corporate leaders pull
back the curtain on the hiring process—and what makes a former educator stand out.
You’ll hear from:
· Steven Anderson, engineering solutions for schools at PowerSchool
· Timothy Gwynn, now leading global learning at Krispy Kreme
· Nicholas Provenzano, managing training and content at SchoolAI
Together, they’ll
share the lessons they’ve learned from both sides of the career transition—how
they navigated the leap, what helped them succeed, and what they now look for
when hiring former teachers.
If you’ve ever
thought, “Could I really make a move like that?”—this session will show
you the answer is yes.
💡 Key Takeaways:
- What hiring managers look for in former teachers
- How to confidently position your teaching experience on a resume or in an interview
- The biggest mistakes teachers make when applying—and how to avoid them
- Encouragement and advice from educators who have successfully made the leap—and now help others do the same
🕦 1:00pm – Session 4: Panel Discussion
The Messy Middle: How Real Teacher are Gaining Traction and Moving Forward
Featuring: Rachel Dunbar, Samara Birkey & Renee Jackson
What does it really look like to leave teaching and start over?
In this honest and inspiring panel, former educators share the behind-the-scenes stories of how they made the leap—from self-doubt and identity shifts to confidence, clarity, and new careers they love.
You’ll hear from:
· Katie Fielding, Content Manager at Book Creator
· Amy Donato, Instructional Coaching and Professional Learning at Elevate K12
· Holly Owens, Instructional Designer
You’ll hear their real stories of how they navigated uncertainty, overcame imposter syndrome, explored new possibilities, and found their footing outside of education. Each panelist brings a unique path, industry, and perspective—but all share one powerful message: it’s possible, and you’re not alone.
Whether you're just beginning to explore new paths or in the thick of your job search, this session will remind you that reinvention is within reach.
💡 Key Takeaways:
· Candid stories from teachers who’ve successfully changed careers
· Insights into new and different career paths
· Confidence-building insights and mindset shifts that helped them move forward
· Real talk on the emotional side of career change—and how to navigate it
· Encouragement and practical advice from people who’ve been exactly where you are
🕦 1:45pm – Summit Send Off
Prizes, Surprises, and Next Steps
Wrap up your day with this high-energy closing session! We’ll celebrate your progress, give away some exciting prizes, and share practical tips to help you keep moving forward in your career transition. If you’ve been wondering how to build on everything you learned today—this is the session you don’t want to miss.
FREQUENTLY ASKED QUESTIONS
Q: Who
is this summit for?
Q: What
if I can’t attend live?
Q: How
do I join the Event once I register?
Q:
Do I have to be a member of the Teacher Career Transition Academy to attend?
Q: What will I walk away with if I attend?

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EdTech Executive | CEO of LearnWorld
Lisa Harding is a former EdTech Executive with over 15 years of experience driving growth and innovation in the EdTech market. Most recently, Lisa served as President of SimpleK12, an online professional development company for K-12 educators. Prior to serving as the company President, Lisa held roles in product/content marketing and development, eCommerce, and sales. Lisa has dedicated her career to providing award-winning training and development to classroom teachers. She has also interviewed and hired many career changers – specifically teachers! Throughout her career in the EdTech industry, Lisa has demonstrated strong leadership, a passion for educators, and a deep commitment to providing best-in-class online courseware. Lisa now serves as Co-Founder and CEO of LearnWorld.
This Session Is No Longer Available — But Don’t Worry!
But check out our current FREE Teacher Transition Career Event!

SAVE MY SPOT!
Former Educator
Chelsea Maude Avirett is a former educator and the founder of Skip’s Job Board, a curated platform designed to help educators find roles that align with their skills and experience. After experiencing firsthand how time-consuming and overwhelming the job search process can be, she launched the platform in 2021 to streamline access to relevant opportunities.
Since then, Chelsea has curated over 20,000 education-adjacent roles, helping job seekers identify positions across both major companies and smaller organizations. She also has extensive experience interviewing candidates across a range of roles and regularly shares insights on hiring trends in EdTech and Learning & Development through podcasts and professional speaking engagements.
Former Educator
Nate Ditterline is a former educator with over 15 years of instructional experience and now serves as a Supervisor for Expanse Trainers, supporting technical training for a new software rollout. After transitioning out of the classroom, Nate has focused on training development, onboarding, and leadership support—helping teams successfully adopt new systems and processes.
Throughout his career, he has trained over 400 leaders, co-developed and facilitated leadership programs, and led large-scale training initiatives. Nate brings a practical, collaborative, and people-centered approach to training, along with a strong background in curriculum implementation and professional development.
management.
Former Educator
Gina Arnello made the decision to pursue a new path that aligned with her passion for accessibility, communication, and problem-solving after 20 years as a special education teacher. With support from the Teacher Career Transition Academy, she successfully transitioned into her current role as an Assistive Technology Specialist.
In her role, Gina works with individuals with disabilities, families, and support teams to expand communication access and implement tools such as AAC and other assistive technologies. She is passionate about helping others find practical, individualized solutions and is excited to share her journey with educators exploring what’s next.
Former Educator
Denise Treadway spent 29 years as an elementary classroom teacher before retiring from education in 2025 and beginning a new chapter in her career. She now works as an Estimator for Texas Site Services, a locally owned pavement striping and sweeping company.
Denise’s transition highlights that it’s never too late to make a change. In addition to her current role, she serves on the Board of Education for Shepherd of the Hills Lutheran School and Childcare. She brings a thoughtful, steady perspective to the transition process and is excited to share what it’s looked like to start something new after a long career in education.
Transitioning Educator
Renee Jackson is currently in the “messy middle” of her career transition after more than a decade in education. She teaches English as an Additional Language and brings a diverse professional background that includes experience as a computer programmer, homeschooling parent, and international educator.
After teaching in Costa Rica, Hong Kong, and now in the U.S., Renee recently made the decision to explore new career opportunities. Since joining the Teacher Career Transition Academy, she has been actively applying to roles, gaining traction, and beginning to receive callbacks. Renee brings a real-time, honest perspective on what it looks like to navigate change while still in the classroom.
Special Education Teacher
Rachel Dunbar is a special educator with over eight years of experience supporting diverse learners and leading professional development in K–12 schools. She is currently transitioning into the EdTech space, exploring roles in implementation, onboarding, and professional learning.
Through her journey, Rachel has leaned into the support of the Teacher Career Transition Academy, where coaching, mindset work, and community have helped her build confidence and strengthen her interview skills. She brings a thoughtful, reflective perspective to the transition process, along with a creative edge as a stand-up comedian and show producer.
Transitioning Educator
Samara Birkey is currently balancing roles as a high school civics teacher and office administrator while exploring new career opportunities beyond the classroom. Her passion for culture, history, and technology has shaped her approach to teaching and continues to influence her next steps.
Known for her strong work ethic, adaptability, and problem-solving mindset, Samara is actively building momentum in her transition. She brings a grounded, thoughtful perspective to the “messy middle” and is committed to finding a path that aligns with both her skills and long-term goals.
LinkedIn Strategist
Deiera Bennett is the owner of Career Confidence by Dee. She uses her 6+ years of marketing, writing, and education experience to teach jobseekers how to market themselves for new careers. Deiera currently works for a branding agency as a LinkedIn Strategist & Ghostwriter for CEOs. Whether you’re a teacher or a CEO, her goal is to help you confidently communicate your value to your audience.
Corporate Learning & Development Executive
Charissa Stowers is an experienced senior level Learning and Development Director. Charissa has a proven track record of development and launch of innovative, industry leading programs that help people ENJOY learning. She has experience hiring and managing teams within the L&D space. With over 15 years of career experience in the technology field, she has had many roles at various companies. She’s worked at small tech startups, and at large international companies such as Apple and Pandora/Sirius XM.
Life & Career Coach
Kate Hutson is a Life & Career Coach providing trusted coaching for professional women to show up with confidence and take control of their careers. After a decade of passionate work as a business leader, teacher, and coach, Kate turned her passion for mentoring others into practical knowledge for the real world– skills that women can use in their everyday lives to achieve their long-term career goals and live with more joy, energy, and fulfillment.
Career Exploration Coach & CEO @WOKEN
Rachel Serwetz’ early professional experience was at Goldman Sachs in Operations and at Bridgewater Associates in HR. From there, she was trained as a coach at NYU and became a certified coach through the International Coach Federation. After this, she worked in HR Research at Aon Hewitt and attained her Technology MBA at NYU Stern. Throughout her career, she has helped hundreds of professionals with career exploration and for the past 4.5 years she has been building her company, WOKEN, which is an online career exploration platform to coach professionals through the process of clarifying their ideal job and career path. She is also an Adjunct Professor of Entrepreneurship at Binghamton University and has served as a Career Coach through the Flatiron School/WeWork, Columbia University, and Project Activate. Learn more about WOKEN here: iamwoken.com.
Career Coach
Alyson Garrido is passionate about supporting professionals to advance their careers and find jobs they will enjoy. As a career coach, she partners with her clients to identify their strengths and create a path toward a more fulfilling career. Alyson provides support around interview preparation, performance reviews and salary negotiations, ensuring that her clients present themselves in the best possible light. Learn more or book a session with Alyson by visiting www.alysongarrid.com.
Customer Success Executive/CEO
Annie Dean (she/her) is CEO and Cofounder of RecastSucces; working to diversify the tech industry by helping career transitioners, supporting mentorship, and Fractional Head of Success leadership for SaaS startups. She is also a Udemy for Business and Maven instructor. Previously she was a career transitioner herself. She went on to Customer Success leadership and executive roles at LinkedIn, Coursera, and several startups. She is a wife and mom living in a rural community near Yosemite.
GCDF, CPRW
Shannon Schwaebler has over eight years of experience in career development and higher education. She has dedicated her career to supporting individuals in navigating their career paths, providing them with the necessary tools and skillset to confidently navigate their career development process. Shannon understands that career paths are not always straightforward and linear. Instead, she believes that success comes from being prepared for the unpredictable and having the ability to adapt to new situations. Her approach to career development is centered around empowering individuals with the skills and knowledge to succeed in their chosen field. Shannon holds a Bachelor’s degree in Chemistry, a Master’s degree in Higher Education, and multiple certifications, including Global Career Development Facilitator, Certified Professional Resume Writer, Certified Program Planner, and AAUW Salary Negotiation trainer.
Director of Growth Marketing
Yellowdig
Former Educator
Holly Owens is a former educator turned edtech and instructional design leader, with over 18 years of experience at the intersection of education, technology, and marketing. As Director of Growth Marketing at Yellowdig, she helps organizations create meaningful, people-first learning experiences.
She also serves as an Adjunct Professor at Touro University, preparing future instructional designers to thrive in today’s digital learning landscape. Holly hosts the EdUp L&D podcast, where she spotlights the voices and innovations shaping the future of learning—with a strong focus on accessibility, inclusion, and impact.
Educational Consultant, Speaker
Former Educator
Reba Gordon Matthews is an Educational Consultant with Houghton-Mifflin-Harcourt and a a Freelance Coach and Instructional Designer creating eLearning and learner experience courses. She has over 20 years of elementary teaching experience and has served as an adjunct instructor for Early Childhood Education courses. She holds a Masters in Educational Technology and a Masters in Instructional Design.
As a way of “Paying It Forward,” Reba is also the co-founder and Executive Director of The Jamal Gordon-Hill Foundation. This small family organization supports at-risk young people with academic tutoring, technology training, and college scholarships.
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Curriculum Designer

Global Career Development Facilitator
Marcia coaches individuals to live their best professional lives. Her expertise lies in the areas of career services, coaching, workshop facilitation, and writing. Her coaching style is both holistic and strategic. It is also rooted in DEI principles and practices. She is a Global Career Development Facilitator and a Certified Career Services Provider through the National Career Development Association. She is also certified through Recovery Innovations International to support people with a recovery mindset. Additionally, she holds a Master of Arts degree in Rhetoric and the Teaching of Writing and is a former English instructor and K-12 teacher.
Amy Donato is a former middle school science teacher turned instructional coach and professional learning facilitator, passionate about helping educators thrive. After years in the brick-and-mortar classroom, she now supports teachers through practical coaching and engaging PD that builds confidence in teachers and improves instruction for students.
Edu. Content manager at Book Creator
Former Educator
Katie Fielding is an educational consultant with 20 years of public school experience. She champions digital accessibility, creativity, and Universal Design for Learning (UDL) in classrooms. Specializing in technology and STEM integration, Katie creates interdisciplinary instructional experiences and shares her expertise through presentations and workshops. Recognized as VSTE Coach of the Year in 2018 and a featured voice at ISTELive 2024, she holds multiple certifications, including UDL Credential 2, ISTE Certification, Google Innovator, and Microsoft Innovative Educator Expert. She is a trainer for the ISTE Certified Educator program, and works for Book Creator as their Educational Content Manager.
Director of Solutions Engineering
Steven W. Anderson is a former educator and nationally recognized voice in educational technology, now serving as Director of Solutions Engineering at PowerSchool. With over a decade of leadership experience supporting schools and districts, Steven helps design strategic solutions that elevate teaching, learning, and digital integration across K–12 systems. At the summit, he’ll share his perspective as former teacher turned hiring manager.
Nicholas Provenzano is a former classroom educator who now leads community and content strategy at SchoolAI, where he trains teachers and develops tools to enhance student learning through AI-powered solutions. With over 20 years of experience as a teacher, consultant, and professional development facilitator, Nicholas is passionate about empowering educators to integrate technology and maker-centered learning in meaningful ways. At the summit, he’ll share his perspective as former teacher making the transition and advice from the “other side” of the hiring table.
Director of Global L&D Krispy Kreme
Timothy Gwynn is a former teacher turned corporate learning strategist, currently serving as the Director of Global Learning & Development at Krispy Kreme. With a background that spans education, instructional design, and enterprise training, he now leads global professional development initiatives that prioritize learner engagement and align closely with business goals.
NOW AVAILABLE!
You Asked.
We Listened.
Limited time Introductory Offer + Member Discount!
Limited spots available -
book before pricing goes up!

NOW AVAILABLE!

You Asked.
We Listened.
Limited time Introductory Offer + Member Discount!
Limited spots available -
book before pricing goes up!





