EPISODE · May 31, 2026 · 34 MIN
Strive, Be Visible, Protect Your Peace: Jackie Chambers de Freitas, Salesforce VP AI, Transformation
from Island Woman Podcast · host Dianne N Squires
Caribbean women pursuing their professional goals on the global stage carry both the distinction and the burden of representation, coming from cultures where excellence is the standard. While striving to be exceptional is vital, protecting your peace and mental health is paramount for sustainable success. Jackie Chambers de Freitas, a 20-year tech executive and current Salesforce VP of AI Delivery and Transformation, breaks down the cost and benefit of corporate leadership with Dianne Squires, founder of Dianne N Squires Consulting (DNSC), on this episode of the Island Woman podcast.---------------------Jackie Chambers de Freitas is deliberate about using her voice and visibility as a tech leader to encourage other women to aspire to higher levels of achievement in the space. And she does so while acknowledging that the cost of leadership can be high and attention to mental health must be intentional. I soaked up her wisdom and straightforward approach in our conversation on this week’s episode. She was transparent about being mindful of her own mental health, having seen it affect members of her family. We also explored how she's applied her agile methodology philosophy to her personal life and how women over 45 can embrace inevitable shifts in their careers and the power of AI. Timestamps00:00 - Shaping corporate identity: Your internal Compass over External Expectations00:08 - Introducing Jackie Chambers de Freitas 00:52 - Island Woman Podcast Intro 02:08 - 3 Survival Tips for Women Navigating the Global Corporate C-Suite 03:16 - Caribbean Heritage: Jackie’s Roots 04:54 - The Importance of Visibility as a “Unicorn” leader 07:59 - Prioritising Mental Health for Caribbean Women Striving for Excellence 08:49 - Setting Boundaries, Protecting Your Peace: Balancing the Importance and the Cost of Visibility 10:23 - Agile Philosophy and AI Transformation: Iterative Change at Speed 14:22 - Applying Agile Philosophy to Personal Life Goals 17:03 - Experiencing Joy as a Woman in STEM (Science, Technology, Engineering and Maths) 20:08 - The “Boon and Burden” of being a Unicorn 22:19 - The Strength of a Caribbean Value System for Playing Big as a Unicorn24:20 - Jackie rates herself on the Ambition/Wellbeing Scale 28:58 - Navigating Inevitable Career Shifts in the World of AI: Leaning into Personal Brand Development for Women Over 45 31:27 - Embracing AI Skills, Broadening Career Horizons for Women Over 45 Get In Touch Follow our curated WhatsApp channel.📲 https://whatsapp.com/channel/0029Vb7lcdnEFeXrxlKuY31L---------------Connect with DianneLinkedIn: @Dianne N Squires linkedin.com/in/dianne-n-squires-a2389132Email: [email protected] with Jackie Chambers de FreitasLinkedIn: @Jackie Chambers de Freitashttps://www.linkedin.com/in/jackie-defreitas/----------------------Dianne N. Squires is a Strategic Communications leader, Founder of Dianne N Squires Consulting (DNSC), and host of the Island Woman Podcast. Through DNSC, her work centres on elevating voice, visibility and impact for Caribbean changemakers.
What this episode covers
Caribbean women pursuing their professional goals on the global stage carry both the distinction and the burden of representation, coming from cultures where excellence is the standard. While striving to be exceptional is vital, protecting your peace and mental health is paramount for sustainable success. Jackie Chambers de Freitas, a 20-year tech executive and current Salesforce VP of AI Delivery and Transformation, breaks down the cost and benefit of corporate leadership with Dianne Squires, founder of Dianne N Squires Consulting (DNSC), on this episode of the Island Woman podcast.---------------------Jackie Chambers de Freitas is deliberate about using her voice and visibility as a tech leader to encourage other women to aspire to higher levels of achievement in the space. And she does so while acknowledging that the cost of leadership can be high and attention to mental health must be intentional. I soaked up her wisdom and straightforward approach in our conversation on this week’s episode. She was transparent about being mindful of her own mental health, having seen it affect members of her family. We also explored how she's applied her agile methodology philosophy to her personal life and how women over 45 can embrace inevitable shifts in their careers and the power of AI. Timestamps00:00 - Shaping corporate identity: Your internal Compass over External Expectations00:08 - Introducing Jackie Chambers de Freitas 00:52 - Island Woman Podcast Intro 02:08 - 3 Survival Tips for Women Navigating the Global Corporate C-Suite 03:16 - Caribbean Heritage: Jackie’s Roots 04:54 - The Importance of Visibility as a “Unicorn” leader 07:59 - Prioritising Mental Health for Caribbean Women Striving for Excellence 08:49 - Setting Boundaries, Protecting Your Peace: Balancing the Importance and the Cost of Visibility 10:23 - Agile Philosophy and AI Transformation: Iterative Change at Speed 14:22 - Applying Agile Philosophy to Personal Life Goals 17:03 - Experiencing Joy as a Woman in STEM (Science, Technology, Engineering and Maths) 20:08 - The “Boon and Burden” of being a Unicorn 22:19 - The Strength of a Caribbean Value System for Playing Big as a Unicorn24:20 - Jackie rates herself on the Ambition/Wellbeing Scale 28:58 - Navigating Inevitable Career Shifts in the World of AI: Leaning into Personal Brand Development for Women Over 45 31:27 - Embracing AI Skills, Broadening Career Horizons for Women Over 45 Get In Touch Follow our curated WhatsApp channel.📲 https://whatsapp.com/channel/0029Vb7lcdnEFeXrxlKuY31L---------------Connect with DianneLinkedIn: @Dianne N Squires linkedin.com/in/dianne-n-squires-a2389132Email: [email protected] with Jackie Chambers de FreitasLinkedIn: @Jackie Chambers de Freitashttps://www.linkedin.com/in/jackie-defreitas/----------------------Dianne N. Squires is a Strategic Communications leader, Founder of Dianne N Squires Consulting (DNSC), and host of the Island Woman Podcast. Through DNSC, her work centres on elevating voice, visibility and impact for Caribbean changemakers.
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Strive, Be Visible, Protect Your Peace: Jackie Chambers de Freitas, Salesforce VP AI, Transformation
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