Coaching, Workshops, And Retreats

Career Coaching & Outplacement Services

We specialize in coaching leaders who seek greater self-compassion, clarity, and conviction to take meaningful action on their goals. Organizations often engage us to deliver high-quality, personalized career coaching and outplacement services.

Our clients turn to us for support in areas such as:

  • Rediscovering strengths to lead with more impact

  • Navigating big career or life transitions

  • Re-entering the job market and mastering the modern job search

  • Building a personal brand for more financial freedom

  • Moving from idea to action

  • - Managing Director, Leadership Development

  • -Senior Managing Director

  • -Psychiatrist, MD

Coaching FAQs

  • All values-driven leaders across different sectors (tech, corporate, education, non-profits, to name of a few). Many clients identify as BIPOC, women and/or gender expressive, immigrants, children of immigrants, and/or neurodivergent.

  • Coaching is a collaborative, deeply personal process that aims to help you find clarity in who you are, what you want, where you are trying to go, and what is getting in the way of forward movement. Each coaching relationship is different, and we customize our coaching based on the needs of the client. 

    3 or 6 month commitment for coaching packages

    Clifton Strengths Leader Report and Personalized Report

    First session is a 90-minute session; the rest of the sessions are 60 minutes

    Creative exercises, homework, and recommended tools between sessions to extend your learning 

    Limited voice memo and email support between sessions

    Personalized google drive folder with all the recordings and resources from your sessions 

    Virtual or in-person in the East Bay Area

  • Clients have found the services to be creative and strategic coach. We draw upon various modalities, such as CliftonStrengths, creative exercises, somatic techniques, and a toolkit of curated resource.

Retreats & Cohort-Based Leadership Programs

We partner with organizations to create reflective containers that provide restoration, creative reflection, and renewed commitment to their work. We are often hired by organizations to create a psychologically safe container (retreats, cohort-based programs, etc.) to support underrepresented leaders, leaders of color, caregivers/parents, and women of color and non-binary femmes. We are proud to have an average NPS score of 98/100 on cohort-based programs.

Areas of Expertise:

  • Restorative Retreats and Offsites

  • Cohort-Based Leadership Development Programs

  • Employee Resource Group & Affinity Spaces

  • WOC and Non-Binary Femmes Leadership Programs

Career Coaching Testimonials

  • I began my coaching with Rupa as I transitioned out of a previous role. I felt overwhelmed and anxious. I needed help shifting my mindset and creating a new plan based on where I want to be in the future. Rupa provided a safe space while offering practical guidance that helped me get excited and reinspired about what lies ahead!

    Rachel Femi Adeyemo, Director of Special Projects, New Schools Venture Fund

  • "Rupa was so helpful as I began thinking about a new role. She was able to ask me powerful questions during our session and really push my own thinking. Rupa used my strengths from StrengthsFinder to help me reflect on my own career journey and helped me see ways I can use them during the interview process. Can't wait to keep learning from you Rupa!"

    Aditi Bhattacharyya, Managing Director, Teach For America - Bay Area

  • “Rupa supported our employees during a reduction is force. Our employees found the support from Rupa to be highly impactful and supportive during an otherwise difficult time. I would recommend Rupa to any organization looking for coaching support for their employees.”

    Heather McManus, Chief Learning Officer, New Schools Venture Fund

Workshops, Retreats, and Cohort Programs Testimonials

“Thank you so much for hosting a dynamic space. I appreciate your facilitation and how you adapt to the room.”

— J.T, Teacher

“Rupa is an incredible facilitator who quickly builds community and thoughtfully designs with each participant in mind. I found her methods both unique and holistic. The activities and suggestions were easy to integrate into existing routines and to share with colleagues. They have had an immediate impact on my leadership and self care. — D.S, CEO

“This program has provided me with a newfound community of superstar women/non-binary femmes. We learned so much from each other through the topics that were explored. We were able to be vulnerable in a safe, warm, and affirming space. So grateful!
— A.V, Coach

I really felt blessed & enriched to share space with such a phenomenal and diverse group of amazing folks. Our facilitator and team created a thoughtful set of curricula and activities for us to grow.

— L.K, Entrepreneur

  • "I just wanted to say a huge thank you to you for your coaching and support. The resources you gave me were so incredibly helpful! I revamped my resume multiple times, going through all that you provided. And all of the questions you asked me and things you left me to think about helped me feel confident, optimistic, and ready to take on everything! I got both jobs I did interviews for!"

    -Operations and Matriculation Managing Director

  • "Rupa, you are a true gem. Thank you for creating this Oasis for us bi-weekly to come as we are and share in each other experiences. To find solace and comfort among those with similar lived experiences and also be willing to challenge our assumptions and beliefs is a rare gift. This was my favorite present of all in 2022."

    -Executive Director

  • "Rupa's knowledge and insight into CliftonStrengths coupled with her real life experience made her presentation engaging and rewarding. She has a welcoming and reassuring style that made even a virtual audience feel like we were all getting to know each other in a fireside chat. I recommend Rupa to guide teams, families, and other groups who are looking to strengthen and grow together."

    -Human Resources Director

  • "Lulu and Georgia had the pleasure of working with Rupa as a CliftonStrengths facilitator recently. Rupa’s infectious energy and passion for the learning and development space was evident instantly. Rupa shared so many nuggets of wisdom and introduced CliftonStrengths in a very tangible and self-paced way. I so value Rupa’s partnership and expertise in this space."

    - Talent Director

  • "I had the gift of being part of this incredible Strengths and Style group program. As a mid-level working mom of young kids, I often feel overwhelmed by the day to day and also stuck in thinking & dreaming about my career and my life outside of being a parent. Rupa's content and supportive, warm approach was like the cheerleader / career coaching I never knew I needed. I came away from the program feeling so known, so connected, so empowered, and most of all so excited and open for future possibilities. This program is a MUST!"

    -Strategy Team Leader

  • "Rupa has been an exceptional thought-partner and coach, guiding and empowering me through every step of my career transition journey with invaluable insights and unwavering support."

    -Alumni Leadership Programs and Experiences Managing Director