Coaches

Make an appointment with one of our coaches or other career experts.

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Gary Ainsworth headshot.

Gary Ainsworth

Becca Carnahan

Gayle Draper headshot.

Gayle Draper

Heather Wilkerson

Heather Wilkerson

Gary Ainsworth is a certified Career Management and Executive Coach.   Having 25 years of executive experience in startups and midcaps, and over 30 years in engineering and operations management, Gary currently works with executive clients on organization transformation.

Before joining PathWise, Gary’s coaching efforts were an integral part of his management consulting business, helping his clients understand that leadership and growth are not just based on dollars and cents.  Often working with highly specialized technical executives, he emphasizes leadership initiatives reinforcing vision, purpose, and communication. 

His mission is to help startup and midcaps executives develop leadership tools to execute their company’s vision.

Becca Carnahan is a career coach, author, and mom from Massachusetts. She is the founder of Becca Carnahan Career Coaching & Communications, where she specializes in helping mid-career professionals find more joy and fulfillment in their work. She also writes and manages the working mom blog, With Love Becca, which helps women manage motherhood, manage careers, and manage to laugh through it all. 

Becca gained her expertise in the career development field over a 13-year career at Harvard Business School, where she still works as a career coach, and while earning her Masters’ Degree in Education from the Harvard Graduate School of Education. 

In addition to her career coaching work, Becca is also the author of Belinda Baloney Changes Her Mind, a fun and inspiring “when I grow up” children’s book and When Mommy Grows Up: A Guide to Parenting Yourself to a More Fulfilling Career.

Gayle is an inspiring career coach with 25+ years in the careers industry. Clients see her role as that of the North Star, guiding their journey to define and facilitate their career goals. She is the founder of Intentional Careers HR specializing in career coaching and career marketing for evolving leaders, senior management, and executive levels.

Her motto is simple: “Never be in a kayak but build your dragon boat (network) of colleagues and friends with a coach at the helm, to give you the momentum to move onto the next successful chapter in your work life”.

Coaching has always been a part of Gayle’s life—first as a Level III National Coach in gymnastics and now as a Certified TypeCoach-Master Coach. She is known for her energizing, authentic, and empathetic approach, as she helps clients bring their vision to fruition.

Gayle proudly served the SEAL Future Foundation as a Career Transition Coach to US Navy Seals, is a published member of the Forbes Coaching Council, and a national leader in the careers industry winning two Awards of Excellence, as a Community Outreach Specialist.

She is a recognized speaker and facilitator offering insights and practical content that can be easily implemented. Gayle is a natural at building forward momentum as she coaches people through employment transitions, leadership growth, and to greater workplace success.

Heather holds a Master’s in Counseling, received coaching training and certification through the Co-Active Training Institute (CTI), and is credentialed as a Professional Certified Coach (PCC) by the International Coaching Federation (ICF).  Heather is currently a Senior Career Consultant for Right Management Consulting, coaches IT career changers for Flatiron and is the founder of Heather Wilkerson Coaching where she provides professional, personal and career coaching focusing on transitions, managing roadblocks and handling life-changing events. She focuses on professionals experiencing burnout, personal change, and supporting clients to create meaningful careers at any stage.   

Heather began her career in Human Resources and Employee Assistance Programs.  Over 20 years ago, she moved to career coaching and helping clients manage change.  Since then, she has built three different comprehensive Career Development programs, created online career suites, and written and presented numerous training and development programs, including a 3-day career transition workshop, plus an award-winning Career Change and Growth webinar series. Recently, she led Leadership and Career Programs for Brown University Alumni and served as Director of Career Services for the Brown University Master’s in Public Affairs (MPA) program.  She has over 20 years of coaching experience working in Higher Ed, Fortune 100 companies, the Federal Government and healthcare organizations.  

She approaches career coaching with the belief that everyone has great skills and strengths waiting to be uncovered.  She has experience helping clients tell their story, craft career plans and generally consult on the self-marketing process.  She partners with clients to clarify and connect with their inner strengths and resources to live their best life and reach their goals with ease.    

Heather Lives in Rhode Island with her husband and has 4 children at various stages of launch! She enjoys running, yoga, all types of boating and hiking.  She is an aspiring cook and musician.

Specialty Filter

Specialty Filter
Gary Ainsworth headshot.

Gary Ainsworth

Gary Ainsworth is a certified Career Management and Executive Coach.   Having 25 years of executive experience in startups and midcaps, and over 30 years in engineering and operations management, Gary currently works with executive clients on organization transformation.

Before joining PathWise, Gary’s coaching efforts were an integral part of his management consulting business, helping his clients understand that leadership and growth are not just based on dollars and cents.  Often working with highly specialized technical executives, he emphasizes leadership initiatives reinforcing vision, purpose, and communication. 

His mission is to help startup and midcaps executives develop leadership tools to execute their company’s vision.

Gayle Draper headshot.

Gayle Draper

Gayle is an inspiring career coach with 25+ years in the careers industry. Clients see her role as that of the North Star, guiding their journey to define and facilitate their career goals. She is the founder of Intentional Careers HR specializing in career coaching and career marketing for evolving leaders, senior management, and executive levels.

Her motto is simple: “Never be in a kayak but build your dragon boat (network) of colleagues and friends with a coach at the helm, to give you the momentum to move onto the next successful chapter in your work life”.

Coaching has always been a part of Gayle’s life—first as a Level III National Coach in gymnastics and now as a Certified TypeCoach-Master Coach. She is known for her energizing, authentic, and empathetic approach, as she helps clients bring their vision to fruition.

Gayle proudly served the SEAL Future Foundation as a Career Transition Coach to US Navy Seals, is a published member of the Forbes Coaching Council, and a national leader in the careers industry winning two Awards of Excellence, as a Community Outreach Specialist.

She is a recognized speaker and facilitator offering insights and practical content that can be easily implemented. Gayle is a natural at building forward momentum as she coaches people through employment transitions, leadership growth, and to greater workplace success.

Becca Carnahan

Becca Carnahan is a career coach, author, and mom from Massachusetts. She is the founder of Becca Carnahan Career Coaching & Communications, where she specializes in helping mid-career professionals find more joy and fulfillment in their work. She also writes and manages the working mom blog, With Love Becca, which helps women manage motherhood, manage careers, and manage to laugh through it all. 

Becca gained her expertise in the career development field over a 13-year career at Harvard Business School, where she still works as a career coach, and while earning her Masters’ Degree in Education from the Harvard Graduate School of Education. 

In addition to her career coaching work, Becca is also the author of Belinda Baloney Changes Her Mind, a fun and inspiring “when I grow up” children’s book and When Mommy Grows Up: A Guide to Parenting Yourself to a More Fulfilling Career.

Heather Wilkerson

Heather Wilkerson

Heather holds a Master’s in Counseling, received coaching training and certification through the Co-Active Training Institute (CTI), and is credentialed as a Professional Certified Coach (PCC) by the International Coaching Federation (ICF).  Heather is currently a Senior Career Consultant for Right Management Consulting, coaches IT career changers for Flatiron and is the founder of Heather Wilkerson Coaching where she provides professional, personal and career coaching focusing on transitions, managing roadblocks and handling life-changing events. She focuses on professionals experiencing burnout, personal change, and supporting clients to create meaningful careers at any stage.   

Heather began her career in Human Resources and Employee Assistance Programs.  Over 20 years ago, she moved to career coaching and helping clients manage change.  Since then, she has built three different comprehensive Career Development programs, created online career suites, and written and presented numerous training and development programs, including a 3-day career transition workshop, plus an award-winning Career Change and Growth webinar series. Recently, she led Leadership and Career Programs for Brown University Alumni and served as Director of Career Services for the Brown University Master’s in Public Affairs (MPA) program.  She has over 20 years of coaching experience working in Higher Ed, Fortune 100 companies, the Federal Government and healthcare organizations.  

She approaches career coaching with the belief that everyone has great skills and strengths waiting to be uncovered.  She has experience helping clients tell their story, craft career plans and generally consult on the self-marketing process.  She partners with clients to clarify and connect with their inner strengths and resources to live their best life and reach their goals with ease.    

Heather Lives in Rhode Island with her husband and has 4 children at various stages of launch! She enjoys running, yoga, all types of boating and hiking.  She is an aspiring cook and musician.

Coaching Services

Business people climbing up arrows toward growth and success

Moving Up

Moving Up is for those of you aiming to advance in your current organization. We'll work with you to assess your strengths and development needs, evaluate your current job situation and advancement options, plan a strategy that fits your situation and identity, and begin implementing an action plan.


Cost is $597 and includes 4 one-hour 1x1 sessions with one of our career coaches
Businesswoman standing on the crossroads with three arrows and directions

Moving On

Moving On is for those of you who are looking to change jobs or even change careers. We'll help you identify what's important to you in your professional life, consider relevant options, prepare a job search or career change strategy, and launch execution.


Cost is $597 and includes 4 one-hour 1x1 sessions with one of our career coaches
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Introductory Coaching 3-Pack

If none of our coaching and career services packages feels like they quite fit your situation, that’s ok! Our team helps clients on a wide variety of career and leadership topics. Get the help you need with an Introductory Coaching 3-Pack.


Cost is $497 and includes 3 one-hour 1x1 sessions with one of our career coaches.
Successful business teamwork concept. Vector flat cartoon graphic.

Follow-On Coaching 3-Pack

Want to continue to work with our coaches after completing your initial package? We’d love that! Follow-on coaching packages are available for just this purpose. Note that this package may not be used until you’ve purchased an introductory package.


Cost is $447 and includes 3 one-hour 1x1 sessions with one of our career coaches.
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