Jessie May’s Bio

Jessie May is a creative alchemist, heart-led coach, and soulful entrepreneur devoted to helping visionaries and leaders rise with purpose, presence, and truth. Known for her signature voice and magnetic presence, she brings a rare blend of emotional intelligence, artistry, and playful embodiment into everything she creates. Through her intuitive approach, Jessie May guides others to remember who they are, reclaim their radiance, and lead from the heart—in life, love, and business.

Born in Montreal, based in Los Angeles, and shaped by a global path of exploration and reinvention, Jessie May has spent over two decades bridging the worlds of creativity, healing, and conscious entrepreneurship. Her work is rooted in presence, powered by truth, and guided by heart.

She is the Founder of HeartRise, a method for emotional intelligence that transforms emotional energy into empowered presence—practiced globally through leadership trainings, community circles, and immersive experiences. HeartRise is at the forefront of shifting culture in corporate spaces and education, bringing heart-powered awareness, connection, and communication to teams, classrooms, and leadership ecosystems. As a heart-first entrepreneur, Jessie May has built and led ventures that fuse creativity with soul, helping others launch from a place of deep inner alignment.

As the Host of Sunny Side Up, a weekly space for heart-powered living—where listeners come to reconnect, refuel, and remember who they are.

Her journey has spanned fashion, media, coaching and wellness. She launched JESSIE MAY, a colorful women’s fashion collection sold in 400+ stores across North America, and led the creative vision for Nicole Richie’s debut fashion line Winter Harlow. She has partnered with pioneering brands and companies including Alo Yoga, VaynerMedia, Free People, Amazon Studios, Soho House and Uber, offering leadership guidance, emotional intelligence training, and creative mentorship.

Known for her signature healing voice and soulful presence, Jessie May creates transformational experiences that awaken truth, unlock creative power, and activate purpose-driven living and collaboration.

Experience & Highlights

• Founder of HeartRise Method—a global emotional intelligence practice transforming leadership, education + culture
• Host of Sunny Side Up—a podcast celebrating soulful themes about human connection + heart-powered living
• Launched JESSIE MAY, a fashion brand sold in 400+ retail locations across North America
• Former lead designer at Phaidon Press in London — worked on celebrated titles including Halston and Fruits, a visual love letter to Japanese street fashion.
• Led creative direction and strategy for Nicole Richie’s first fashion brand Winter Kate
• Coached thousands of creatives, leaders, and entrepreneurs worldwide
• Certified HeartMath Coach, ICF-Accredited, Reiki Master, and trained in Eastern + energetic healing modalities
• Known for her signature healing voice—featured in guided meditations + immersive sound journeys
• Partnered with leading brands including Alo Yoga, VaynerMedia, Free People, Lululemon, Uber and Soho House
• Recognized for bridging creativity, conscious business, and emotional intelligence—cultivating connection and creating transformational impact from the inside out.

Radiance Offerings

☀️ 1:1 COACHING
Personal, Brand + Love Alchemy for creatives, entrepreneurs + emerging leaders

🎤 SPEAKING
Keynotes, workshops & experiences on leadership, creativity + authentic expression

🎙️ PODCAST
Sunny Side Up offers warm reflections + heart wisdom to remember who you are

🧘‍♀️ MEDITATION + VOICE WORK
Custom healing audio journeys + meditations for individuals, brands + communities

Jessie May works with those ready to live from truth, lead with love, and rise with conviction. Her dedicated work is a sacred invitation to step into deeper alignment—where heart meets purpose, and presence becomes power.