Terri Stephan, a driven leader with a career spanning over two decades, embodies resilience, innovation, and a relentless pursuit of excellence. From entrepreneurship to executive leadership, she has driven organizational growth and recognized revenue growth of 742% over five years. As she transitions from her recent exit to Microsoft and seeks her next professional endeavor, Terri reflects on her journey, passions, and insights that have shaped her remarkable career.
From Fashion Design to Strategic Leadership:
Growing up, Terri harbored dreams of becoming a fashion designer, fueled by her innate creativity and passion for design. While her journey initially led her to pursue a fashion design program, practicality steered her towards a business major. Inspired by her parents’ entrepreneurial spirit and work ethic, Terri embraced the world of business.
“My entrepreneur DNA came from my parents. As a child and well into my adult years, I witnessed them grow a business of their own. They learned new industries and products, formed the right relationships, and prioritized the needs of their buyers and partners. Along the way, they did it with grit and determination. To this day, they have an unparalleled work ethic and entrepreneurial spirit.” – Terri Stephan, 3x Founder and CEO, WECAN President
Unveiling the Woman Behind the Leader:
Beyond the boardroom, Terri finds solace and joy in her passions outside of work. An avid golfer and pickleball rookie, she balances her professional pursuits with moments of creativity and fun. As a devoted mother to two exceptional adult children and a precocious Maltipoo named Cooper, Terri cherishes the moments of connection and joy that enrich her life.
A Day in the Life of Terri Stephan:
Terri’s day begins with a tranquil walk with Cooper, setting the tone for a day of reflection and purpose. Grounding herself through quiet time and devotional practice, she prepares to tackle the challenges and opportunities that lie ahead. From advancing initiatives at WECAN to navigating the tech space with determination and resilience, Terri’s day is a testament to her unwavering commitment to excellence.
“If you treat the people in your channel well, make their work-life more enjoyable and doing business with you easier, and create an outstanding experience for them (and for yourself), you will grow your business and increase your revenue while you maximize profitability.” – Terri Stephan, 3x Founder and CEO, WECAN President
Inspiration Between the Pages:
Currently delving into “Worthy” @jane boulware it’s only one of many titles that Terri finds inspiration and solace in the pages of captivating literature. Books serve as a source of reflection, insight, and rejuvenation amidst the demands of her professional journey.
Empowering Women Leaders:
Terri’s leadership philosophy centers on resilience, empathy, and empowerment. Embracing diversity of thought and perspective, she believes in paving the way for the next generation of women leaders. Terri emphasizes the importance of leading by example, amplifying diverse voices, and fostering a culture of inclusivity and empowerment.
“I’ve witnessed the incredible transition that executives go through when they truly understand who they are, and can speak to their core values, motivations, and experiences – it can be career-transforming.” – Terri
Lessons Learned and Words of Wisdom:
“From my mother, a true business visionary, I learned a profound redefinition of being a CEO: ‘Creating Endless Opportunity,’ ‘Counteracting Each Obstacle,’ and acting as a ‘Catalyst for Empowering Others.’ She instilled in me that leadership is far more than strategy—it’s about weaving resilience and innovation into the very fabric of our approach, urging us to look beyond the immediate. ‘True leadership,’ she would say with unwavering conviction, ‘is about building a legacy of empowerment and enduring impact, not just for ourselves but for those we lead. The real measure of success lies in the opportunities we forge, the obstacles we overcome, and the lasting empowerment we instill in others.’ Her legacy, a beacon of purpose and vision, guides me to lead with heart and make a meaningful difference.”
Navigating Challenges and Building Networks:
In the ever-changing world of technology, women leaders face unique challenges and biases that demand resilience and perseverance. Terri advocates for leveraging networks, sharing experiences, and championing inclusivity to overcome obstacles and drive meaningful change.
“When you’re an entrepreneur, you don’t just wear the CEO hat, you wear every hat. I’ve been CFO, CMO, CRO, you name it. I now want to use my hard-earned CxO portfolio to help other businesses scale.” – Terri
Joining Forces with WECAN:
As a driving force behind WECAN’s transformative initiatives, Terri brings her expertise in strategy, leadership, and empowerment to uplift women in technology. Through the Career AcceleratHER program, she champions skill development, mentorship, and diversity initiatives that shape the future of tech leadership.
“In particular, I want to help women directors scale their career. I know how hard it is to break into the right networks (especially in male-dominated industries like tech). I know the challenges of holding everything on your shoulders – and juggling caregiving, family, parenthood, fundraising, hiring, etc. in parallel.” – Terri
The WECAN Career AcceleratHER program gives director-level women access to senior leaders to propel their careers forward. You can learn more about joining the program at https://wecanleadtech.org/career-accelerather/