Executive Coaching

Say hello to a new Chief membership tier. Now, instead of joining a Core Group, you can opt for goal-based one-on-one guidance from a vetted executive coach — at your own pace and on your own schedule.


Executive Coaching

Why Executive Coaching?

  • Personalized Approach

    Work through a specific leadership challenge or skill over eight one-on-one sessions with a Chief-vetted coach.

  • The Right Coach for You

    We will pair you with a coach who’s aligned with your goals, and you’ll have chemistry fit sessions with up to three different coaches to find your match.

  • Flexible Scheduling

    Meet at a cadence that works best for your personal time and professional demands.

A Few of Our Vetted Coaches

Casey Carpenter

Casey Carpenter has extensive experience (400+ hours) coaching top executives. In addition to her time as an executive coach, she has 20+ years of executive experience across insurance, higher education, government, tech, financial services, transportation, advertising, and senior living industries.

Casey works with clients who are navigating personal and professional change and desire to improve their performance in key leadership areas. They want to conquer imposter syndrome and perfectionism and amplify their voices to elevate their leadership. Her areas of expertise include communication, leadership development, sales, and work-life balance.

In Casey’s own words: “I was born with four strikes against me — shy, introverted, highly sensitive, and scared to speak up. It’s a miracle I’m doing this work. After working two jobs for years, I got the courage to land a job in sales. Struggling with the complex industry concepts, I nearly got fired… until I won a district presentation contest. I stumbled upon a key truth: When you master your content and delivery, you can move rooms of people.”

Hien DeYoung

Hien DeYoung has extensive experience (500+ hours) coaching top executives. In addition to her time as an executive coach, she has 18+ years of executive experience across biotech, medical device, and technology companies.

Hien works with clients who are navigating change — those who are leading business transformations, onboarding into a new role or company, or were once remarkably successful and now need to navigate the new normal. Her areas of expertise include strategic leadership, people leadership, executive navigation, and startup and emerging company CEOs.

In Hien’s own words: “In my previous career, I worked with founders and CEOs to scale up companies. This experience and close-up observation of founders and CEOs built my insights and extensive understanding of leadership development and the outcomes of mindsets and self-beliefs. In my coaching, I use principles of transformational change, emotional and relational intelligence, and brain science.”

Alene Gabriel

Alene Gabriel has extensive experience (400+ hours) coaching top executives. In addition to her time as an executive coach, she has over a decade of executive experience across entertainment, tech, healthcare, CPG, consulting, and banking industries from her first career in research and strategy.

Alene works with clients who know the old systems of working no longer work and are ready to define and create the next evolution of business. Her areas of expertise are navigating the complexities of common (but real!) clichés like having a work-life balance, designing organizational systems consider their inherent humanness an advantage, and creating profound connections.

In Alene’s own words: “I was a disruptor before I knew it was a thing. I questioned why things were the way they were and stubbornly refused to accept ‘because I said so’ as an answer. What I’ve learned is this: Going against the grain invites fear and discouragement from others, but it also opens avenues to do extraordinary things. Being off the beaten path comes with fear, doubt, and disappointment, but it also creates freedom and wild energy. The view from the edge is spectacular.”

2024 Membership Fees (Executive Coaching)

All-Inclusive Pricing

These fees reflect Chief membership that’s inclusive of personal executive coaching and Clubhouse access, along with our curated community and leadership programming.

Interested in an Executive Coaching membership?

Email our team at [email protected] with the subject "I'm Interested in Executive Coaching" to get started.


  • What is the difference between Core and Coaching?

    Core is our peer advisory learning product, where you meet regularly with 8-10 professional peers with a seasoned facilitator. It provides a consistent, structured, and confidential environment for giving and receiving unbiased input. We recommend this option if you want peer advice on a variety of topics.

    Coaching is a one-on-one executive coaching service with a Chief-vetted executive coach. Your coach will work with you to develop an individualized approach, whether you have a specific goal in mind or are simply seeking a thought partner for your difficult leadership questions. Sessions are tailored to your schedule. We recommend this option if you want to tackle a specific leadership challenge with a more flexible schedule.

  • What is included in the Coaching membership?

    The membership includes 8 one-on-one, hourlong coaching sessions, as well as access to the rest of our membership services, such as programming to keep you on top of emerging leadership topics and access to the network and community, both virtually and in-person with access to all of our Clubhouses.

  • What is the price if I'm partway through my Core membership?

    As a courtesy to our current members — for our Executive Coaching launch, you can choose to upgrade to coaching anytime throughout your membership, and the remaining amount for your current membership will be refunded and used towards the balance owed for coaching. You will be charged upon request but your Executive Coaching annual membership term will start on the first day of the upcoming month.

  • How are coaching sessions scheduled?

    You and your coach can schedule (and reschedule) directly with each other based on your availability. This will take place over email with the email address you provided in your onboarding form. The coach may use a scheduling software (like Calendly) to schedule.

  • How long are the sessions?

    Coaching sessions are one hour long.

  • Will sessions take place in any particular cadence?

    No, you will work directly with your guide to schedule based on your availability. If you want to use all 8 sessions within the first 4 months of your membership, that is fine. You are also welcome to spread them out more.

  • How will I be matched with a coach?

    You will be matched with executive coaches who are aligned with your style of working, have experience working with your function, industry, and level of responsibility. If you have specific needs or requests from a coach, we will collect that information up front and try our best to meet your needs in the matching process.

    We’ll introduce you to one coach at a time and schedule a 30-minute “chemistry” session for you to meet with the potential coach before committing to working with them. If the first coach introduced isn’t a fit, we’ll collect that feedback from you, introduce a second option, and schedule a chemistry session. You will be offered up to three chemistry sessions. If after 3 sessions you still haven't found a coach, we’ll work directly with you on next steps.

  • What if I don't like my coach?

    If you don’t like your coach, please reach out to [email protected]. The Chief team will ask for feedback from you on what didn’t work with the current coach and use the information to match you with another who is a better fit. We may ask for a quick phone call to gather more information.

  • Can I meet with a coach before deciding to work with them?

    Yes, you will be offered up to three, 30-minute “chemistry” sessions.

  • Can I request more than eight sessions?

    You can purchase add-on packages of 3- and 6-sessions. The price for three sessions is $3,600 and six sessions is $6,300. You can email the Experience team at [email protected] to purchase add-on packages.

  • What is the attendance policy for Executive Coaching?

    You should reach out to your coach directly if you need to reschedule a session.

    You will not be able to make up a session if you are a no-show to honor our coaches’ commitment.

  • Are there different coaches for VP vs. C-suite?

    We take many factors into consideration when matching you with the right coach, which includes seniority. We ask Guides the amount of hours they have coaching C-suite and VP levels during the onboarding process.

  • What is the expected timeline?

    You will be sent an onboarding form within two weeks of your Coaching membership start date. You can expect to be matched with a coach for your first Chemistry Session within 1 week of completing your onboarding form.