The Career Confidence Collective Coaching Program

Break Through, take action, and fulfill your potential.

You’re talented, you’re experienced, and you know you are made for more. But despite your ambition, you don’t know how to get ahead in your career. What’s holding you back?

Save your spot on the waitlist today!

Save your spot on the waitlist today!

Take charge of your success.

The Career Confidence Collective will give you the tools and support you need to gain clarity, build confidence and take charge of your success. It’s the solution for ambitious women who want to abolish self-doubt, overcome imposter syndrome and achieve their full potential.

When you join the Career Confidence Collective, you’ll find strength in a group of like-minded women who can help you shift your mindset, overcome obstacles and work toward what you really want from your career.

If you’re feeling frustrated and unfulfilled, this program will give you the skills and self-empowerment to navigate your path to advancement.

Stop feeling stuck. Start taking charge.


What are the benefits of The Career Confidence Collective Program?

Here's what you will learn over the course
of the group program:

A 5-month group coaching experience, the Career Confidence Collective gives you tools, techniques, and actionable plans to improve your professional confidence to achieve your career goals.

  • Build your vision. Build a vision for your career and identify what you want next for greater personal and professional fulfillment.
  • Get clarity. Uncover your strengths and values to be clear about exactly what you bring to the table at work.
  • Grow your confidence. Learn techniques to manage self-doubt and the negative voice inside your head and increase your self-confidence.
  • Gain key skills. Discover the importance of personal brand and executive presence and the steps to build skills in these critical areas.
  • Advocate for yourself. Understand how to advocate for yourself in high-stakes situations, including negotiations, managing up, dealing with difficult team members and more.
  • Unwavering community support. Gain accountability and build lifelong relationships to support you on your career confidence journey.

The Career Confidence Collective Program

The Career Confidence Collective allows you to connect with an expert coach and a cohort of like-minded women who will help you gain clarity, confidence and self-empowerment in your career.

When you enroll in the Career Confidence Collective, you get access to:

  • Personalized Coaching. Take part in 2 live coaching calls per month, plus join 1 office-hours call each month for individual questions between group sessions.
  • Confidence-building tools and techniques. Build your confidence and achieve your goals with tools and resources that encourage you to make a plan and take action.
  • Flexibility. Each session is recorded and available on-demand, giving you lifetime access to all coaching materials.
  • Strengths and values assessments. StrengthsFinder and Values assessments deepen your self-awareness and help you navigate your path to success.
  • A safe, small group setting. Benefit from a safe, confidential space where you can share your challenges and gain the collective wisdom and insights of others who will lift you up.
  • Accountability partners. A Confidence Accountability Partner will encourage and support you throughout your career confidence journey—and beyond!  

Enroll now and you’ll have the opportunity to become a member of the Career Confidence Collective BETA Round that will help shape the future of the program for other brave women like you.

5-Month Payment Plan

$ 347 Monthly for Five Months
  • Lifetime Access to all program Q&As and materials

Pay in Full Plan

$ 1497 One-Time
  • Lifetime Access to all program Q&As and materials
Save $238!

What's covered?

Month 1: Getting a Baseline

  • Identify your values and learn how to find your ‘why.’
  • Figure out your saboteurs, how they show up for you and how to harness positive intelligence to manage them.
  • Determine how you want to show up to align with your values and meet your personal and professional goals.

Month 2: Reframe & Rebuild

  • Learn the Confidence Building Model to gain self-awareness and increase your self-belief.
  • Complete a CliftonStrengths Assessment for insight into your professional identity, strengths and preferences.
  • Learn how to identify and silence limiting beliefs, overcome mental hurdles, manage your mindset and regain your confidence.

Month 3: Communicating with Power

  • Uncover different communication and listening styles and learn how to excel with both verbal and non-verbal communication.
  • Explore negotiation techniques, tactics for dealing with difficult people and steps for navigating crucial conversations.
  • Tap into your executive presence and learn how to own the room.

Month 4: Taking Brave Action

  • Build and use communication scripts to navigate discussions with confidence and clarity.
  • Engage in role-play of real-life situations to practice stating your position and overcoming objections.
  • Build action plans for scenarios ranging from job interviews and performance reviews to presentations and negotiations.

Month 5: Putting it All Together

  • Discover the importance of self-care when you’re building career confidence.
  • Explore effective techniques for stress management and coping.
  • Learn how to build a strong community and work with an accountability partner to maintain your momentum.

This program will be an intimate experience of only 8-10 women. 

Program Start Date: Fall 2024

"Jen didn’t need to help me but she did, which I’ll always be grateful for. I needed her career, and more so confidence, coaching during the time she came into my life. She was able to provide a great sounding board, give deep insights, and allow me to truly feel heard. I would recommend her to anyone who is in a career pivot because she validates and challenges you."
Jenna Janssen, Brave Women at Work Coaching Alum
Jenna Janssen
"The biggest thing that I have gained from coaching with Jen is the ability to believe in myself to move forward with the next chapter in my career journey. Knowing Jen was by my side every step of the way finding a new job was invaluable. Once in my new job, I loved how Jen reminded me “it’s not your fault” and gave me permission to feel. I also appreciated the coaching session summaries Jen created and extra resources to enforce points we discussed. Most of all, Jen held me accountable to next steps."
Philly Winterowd, Brave Women at Work Coaching Alum
Philly Winderowd

About Jen

Jen Pestikas is an executive with over 20 years of experience in the financial services industry. She is currently the Senior Vice President of Business Development of a Chicagoland financial institution. Jen understands the necessary skills to make significant leaps in your career, including mindset, asking for what you want, interviewing skills, the ability to negotiate, professional presence and more.

In addition to her corporate work, Jen is leveraging her experience with her personal company, Brave Women at Work. At Brave Women at Work, Jen offers individual and group career and leadership coaching for women. She helps her clients better identify their strengths, what they want, what is holding them back and how to remove these barriers so they can take bolder and braver action in their careers.

Jen has a Bachelors in French and Spanish from Indiana University and an M.B.A. from Lake Forest Graduate School of Management. She is also a Certified Professional Coach and an Energy Leadership Index (ELI) Master Practitioner from the Institute for Professional Excellence in Coaching (IPEC).

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