Master Your Career Transition

2 Weeks


Cohort-based Course

A 2-week course for professional women who want to master a mid to late career transition, cultivate self-worth & design their ideal career.

Course overview

Strategies for Your Career Transition

Are you contemplating a career transition but feeling stuck? Do you want to regain agency in your career choices and design your ideal career?

This workshop will help you gain clarity by helping you to remove obstacles and to create your customized career roadmap using the techniques and tools in the Career Design Playbook ™.

A one size fits all career plan isn't for everyone.

As you mature, owning your career design, driving your next move with intention and making bold changes are essential elements to your success and happiness.

Addressing and eliminating age-related stereotypes is important because, as a mid to late-stage career woman, you possess a wealth of experience, insight, and value that benefits organizational growth. Your wisdom and contributions enrich not only the professional realm but society as a whole.

In this 2 week interactive class, you will learn how to reframe your professional narrative, navigate the current job landscape, use frameworks, practical exercises and group coaching to put in motion a joyful transition.

This course is for you if


you want to change roles or industries and are motivated to reach your full potential in the second half of your career.


you are reentering the workforce and are excited to translate your transferable skills into a new career path.


you have been laid off and are ready to explore where you can continue to make an impact and thrive in your career.

What you'll get from this course

Create your career roadmap, apply concepts from the Career Design Playbook™

Unpack concepts in the Career Design Playbook™ which is a step by step guide for going deeper into the critical areas and skills for your career transition.

Analyze your current career portfolio and create a strategic roadmap that integrates your core values.

Imagine the new you, write your unique professional narrative.

Identify your valuable skills that take years to cultivate and are important contributors to revenue growth and team productivity.

Compose a compelling narrative that serves as the foundation for your resume, LinkedIn profile and thought leadership.

Launch your job search strategy, break down effective search best practices.

Leverage generative AI, professional partnerships, networking techniques and develop your digital presence to navigate today's competitive market

Create your job search plan that makes you stand out as an industry leader.

Ace your interviews, present your business impact.

Crush your interviews with recruiters, hiring leaders and interview panels by confidently aligning your ability to problem solve with your potential new role.

Compose detailed professional highlights that can be used to answer any interview question.

Join the vibrant community, connect with other successful women on similar journeys.

Build relationships with the women in this live cohort based course for support.

Collaborate with amazing leaders who are on parallel paths to grow your already thriving network.

Course Syllabus


Create your career roadmap, apply concepts from the Career Design Playbook™

Tuesday, November 7th, 9:00am-10:30am PST

  • Unpack concepts from the Career Design Playbook™
  • Design your career roadmap while infusing your core values and vision.
  • Learn the essential elements to a successful career transition.


Imagine the new you, write your unique professional narrative

Thursday, November 9th, 9:00am-10:30am PST

  • Write your professional narrative that sets you apart from the crowd.
  • Position your LinkedIn profile to attract hiring managers and recruiters.
  • Leverage ChatGPT to enhance your compelling bio and resume.


Launch your job search strategy, break down effective job search practices

Tuesday, November 14th, 9:00am-10:30am PST

  • Research target companies, assess open roles and build your funnel.
  • Build relationships with hiring leaders, venture capital talent partners, recruiting agencies and internal recruiters.
  • Learn how to increase your chances of getting interviews by leveraging AI tools.


Ace your interviews, present your business impact.

Thursday, November 16th, 9:00am-10:30am PST

  • Create a series of professional highlights that can be used to answer any interview question.
  • Get exclusive information from executive recruiters and hiring leaders on their ideal senior level candidate.
  • Transform an interview into a conversation while noting current trends such as generative AI.


Office Hours

Sign up for 1:1 sessions with Terry to discuss your specific challenges or questions. You can use this time for offer negotiation guidance on any job offers in play.

  • Friday, November 10th, 9:00am-noon PST
  • Wednesday, November 15th, 9:00am-noon PST

Meet Your Instructor

Terry O'Connor

Terry O'Connor

Former Google & Databricks talent acquisition leader, startup founder & investor

For nearly two decades, I've been advising hiring managers at Fortune 500 companies and start ups on winning strategies to hiring top talent. Many senior level tech industry professionals have benefited from my interview coaching resulting in lucrative job offers.

My mission is to create a joyful platform for mid to late career women that offers a holistic approach to career design and managing career transitions. Holistic meaning intentionally structuring your career portfolio that is unique to your core values. The aim is to change the perception that as you age you are less valuable.

The “one size fits all” career path is a thing of the past. I believe that we need to create a new vocabulary for mid to late stage career women. It's important to reject the misconceptions about ageism in the workplace and in society as a whole.

I built the Career Design Playbook™ based on my experiences coaching candidates, advising hiring leaders and navigating my own rewarding career transitions from Wall Street to Real Estate to Silicon Valley.

What people are saying

        Terry is an incredible, mission-driven entrepreneur and instructor. She brings a holistic approach to career transitions and her personal story makes her extremely relatable. Her energy is contagious and she is an empathetic, expert guide for women who want to take agency in designing their career on their own terms.
Veronique Lafargue

Veronique Lafargue

 Founder and CEO, Maison Lafargue
        After years of working as a consultant, I was recently offered a full-time position at a tech start-up and turned to Terry for negotiation advice, which proved to be invaluable. Her depth of knowledge, rooted in lived experience, makes her an indispensable asset to any professional looking to elevate their career.
Sirenetta Leoni

Sirenetta Leoni

Voice and Casting Director at, Voice Coach, Producer and Actor
        In the over 20 years, I've had the privilege of knowing Terry, both as a friend and a professional acquaintance, I've been consistently impressed by her tenacity and strategic acumen. I've watched her masterfully transition across sectors, demonstrating adaptability that's truly rare. She's actively challenging and reshaping the ageism narrative.
Daniela Mielka

Daniela Mielka

Growth focused Board Director, Executive, Advisor
        Terry co-led one of the Google Alumni Women layoff cohorts for women like me who were affected by the 2022 layoffs. She provided valuable job search advice. Given her energy, expertise and EQ, it was a no-brainer for me to take her up on a 1-1 offer. Terry played a part in my success landing a role as the Chief of Staff in a clean tech startup.
Jennifer Vaden Barth

Jennifer Vaden Barth

Chief of Staff, Heliogen
         In my leadership role, I partnered with Terry during Google Fiber's early days. A seasoned leader herself, Terry deeply understands career transitions, having coached many on interviewing & negotiation. Her insights into what hiring managers want is vital for all candidates.
Archana Mishra

Archana Mishra

Global Talent Acquisition Strategist | Ex-Google, Meta (Facebook), PayPal
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Course schedule

4-6 hours per week
  • Create your custom career roadmap

    Tuesday, November 7th, 9am-10:30am PST

  • Imagine the new you, write your unique professional narrative

    Thursday, November 9th, 9am-10:30am PST

  • Launch your job search strategy

    Tuesday, November 14th, 9am-10:30am PST

  • Ace your interviews

    Thursday, November 16th, 9am-10:30am PST

  • Optional 1:1 office hours

    Wednesday and Friday, 9am-noon PST

Learning is better with cohorts

Learning is better with cohorts

Active hands-on learning

This course builds on live workshops and hands-on projects

Interactive and project-based

You’ll be interacting with other learners through breakout rooms

Learn with a cohort of peers

Join a community of like-minded people who want to learn and grow alongside you

Frequently Asked Questions

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Be the first to know about upcoming cohorts

Master Your Career Transition


Bulk purchases