She's been "ruining the workplace" since 1997 — and she has zero regrets. Lori Lalonde spent nearly three decades in corporate tech, including senior leadership roles at Microsoft and Manulife, before walking away to build her own executive coaching practice for women.In this episode, Lori and Jessica dig into the moment a CEO told Lori to choose between her job and her kids, the town hall confrontation that got her called into a boardroom for an "apology," the cupcake incident that ended her office baking career forever, and the specific, practical boundaries — like refusing to answer messages immediately — that changed how she operates as a leader. They also unpack why so many women in corporate are burning out, why "office politics" isn't a dirty word, and what it actually takes to navigate power inside an organization built by people who don't look like you.

Lori Lalonde is the CEO and founder of Her Executive Ascent, an executive leadership advisory practice for senior women in high-stakes organizations, and host of the podcast Leadership Recalibrated.

Connect with Lori:

Website: www.herexecutiveascent.com

LinkedIn: Lori Lalondehttps://www.linkedin.com/in/lorilalonde/

Podcast: Leadership Recalibrated (Spotify & Apple Podcasts)https://podcasts.apple.com/us/podcast...

Follow Connecting the Dots with Jessica Caresse for more conversations on leadership, entrepreneurship, and building a career (and life) on your own terms.

What does it actually take to build an AI platform from the ground up — for the people everyone else is ignoring?In this episode of Connecting the Dots, Jessica sits down with the full leadership team of Indrasy — CEO Kyle, CTO Rose, and CRO Athena — three first-generation Americans building an AI operating system designed specifically for small businesses.They get into how they met, what makes their platform different from ChatGPT and Claude, why South Florida's tech community is so fragmented, the real reason small businesses fail (hint: it's not the service), and what it actually means to build something that adds value instead of just extracting it.Whether you're a small business owner, aspiring entrepreneur, or just curious about where AI is really headed — this one's for you.🔗 Find Indrasy: https://indrasy.com💬 If this episode resonated with you, like, subscribe, and share it with someone building something.

Scaling a company is chaotic, but it shouldn't be a constant fire drill. In this episode, Gaby Enriquez (Founder of HRbp Inc.) breaks down how to build a people and compliance infrastructure that bridges the gap between profit and purpose. Whether you are navigating M&A, expanding into LATAM or APAC, or auditing for cost efficiency, this is your guide to turnkey growth and sustainable scaling.Gaby Enriquez is a global People Operations leader with 20+ years of experience helping organizations scale with integrity. As the founder of HRbp Inc., she bridges the silos between Finance, Sales, and HR to ensure every department speaks the language of business. Known as the "not-so-HR company," her team focuses on P&L, labor law, and organizational psychology to make businesses more human and humans more capable of driving profit.Connect with Gaby:Instagram: @hrbp.inc | @thegabriela.enriquezLinkedIn: Gaby Enriquez

The conversation delves into the emotional journey of recognizing business challenges and the transformative power of investing in solutions. The speaker shares personal experiences of pain and joy associated with financial decisions that lead to business clarity and success. They encourage others to explore their business aspirations and seek help, emphasizing that solutions may be more accessible than they appear.Takeaways• The most painful part was realizing I had a problem.• Writing a big check to get out of a contract was painful.• Paying for a service that works is joyful.• Investing in solutions can lead to business clarity.• It's important to have conversations about business aspirations.• Your business dreams might not be as far off as you think.• Seeking help can make challenges seem less difficult.• Personal growth often involves financial investment.• Understanding how you want your business to run is crucial.• Don't hesitate to explore your business ideas with others.00:00 Introduction04:14 Career Beginnings06:20 Entrepreneurial Challenges14:51 Initial Software Setup25:19 Software Transition Pain32:03 Thoughts on Technology40:45 Working with Richard46:24 Vision for AI58:50 Avoiding Shiny Objects1:10:38 Elder Law Practice

In this episode of Connecting the Dots, host Jessica Caresse speaks with Kaila Sachse, founder of Yumari Digital, about her journey from a junior graphic designer to a successful entrepreneur. They discuss the importance of networking, the challenges of transitioning from employee to business owner, and the significance of maintaining high standards in business. Kaila shares her experiences with mentorship, the value of diversifying income streams, and the journey of recognizing one's self-worth. The conversation emphasizes the importance of encouragement and resilience in the face of challenges.• Kaila never thought she would become a business owner.• She aimed to keep as many doors open for herself as possible.• Designing her life to fit her needs was crucial.• Networking played a significant role in her success.• Under promising and over delivering is essential in business.• Self-worth is a continuous journey for entrepreneurs.• Mentorship can provide invaluable guidance and support.• Maintaining high standards is key to client satisfaction.• Flexibility in work is important for personal well-being.• Encouragement and resilience are vital in entrepreneurship.

In this enlightening conversation, Jessica Caresse and Lorena Anderson explore the transformative power of energy shifting and personal growth. Lorena shares her journey from overcoming personal struggles to becoming a successful life and energy coach. The discussion delves into the importance of self-awareness, breathwork, and the role of unconditional love in fostering personal transformation. Listeners are encouraged to recognize their own energy fields, embrace their authentic selves, and take actionable steps towards empowerment and self-love.Takeaways• Lorena emphasizes the importance of sharing insights to help others find peace.• Personal transformation requires consistent effort and self-acknowledgment.• Understanding one's energy field is crucial for personal growth.• Breathwork can help access and enhance inner energy.• Self-awareness is key to recognizing and trusting one's intuition.• Unconditional love for oneself is essential for healing and growth.• Negative energy can be transformed through conscious practices.• Empowerment comes from recognizing and honoring one's own gifts.• Finding one's voice is a significant step in personal authenticity.• Practical steps and guidance can accelerate personal transformation.

In this engaging conversation, Jessica Caresse and Barbara Alexander explore the fascinating intersection of business astrology and soul-led leadership. Barbara shares her journey from corporate success to coaching, emphasizing the importance of authenticity, personal growth, and understanding one's astrological influences. The discussion delves into collective consciousness shifts, the role of relationships in personal evolution, and the significance of finding alignment in both business and personal life. Listeners are encouraged to embrace their unique paths and seek guidance in their journeys of self-discovery.Takeaways• Barbara Alexander specializes in business astrology and soul-led leadership.• Astrology can help leaders navigate personal and professional growth.• Collective consciousness is shifting towards self-empowerment and authenticity.• Understanding one's astrological chart can provide insights into personal challenges.• Relationships often evolve as individuals undergo personal growth.• Barbara's journey from corporate success to coaching illustrates the power of transformation.• Astrology can inform leadership styles and decision-making processes.• Finding alignment in business requires understanding one's unique energy.• Deconditioning is essential for discovering one's true self.• Self-discovery often involves seeking guidance from mentors or coaches.