WINK x Jess Iandiorio

Breaking Barriers & Building Teams: Insights from Jess Iandiorio, CMO of StarTree

In this inspiring episode of WINK, we had the pleasure of sitting down with Jess Iandiorio, the Chief Marketing Officer (CMO) of StarTree—a company that's making waves in the world of real-time analytic cloud solutions. Jess is a dynamic force in the tech industry, and during our conversation, she shared not only her career journey but also her insights on leadership, mentorship, and navigating the complex landscape of being a female executive in tech. Her perspective on authenticity, empathy, and being a hands-on leader is as refreshing as it is empowering.

From Market Research to CMO: Jess's Career Journey

Jess’s path to the top wasn’t linear, but it was built on passion, curiosity, and a commitment to learning. She started her career in market research at Forrester Research, using her background in organizational communication to dive deep into understanding the business trends and needs of various industries. But Jess didn’t stop there—her curiosity led her into the tech world, where she joined Endeca, a company specializing in enterprise site search. She quickly embraced product marketing, and through hard work and determination, she climbed the ranks to become CMO at StarTree.

But beyond her professional achievements, Jess is also a mother of three boys—ages 7, 9, and 11. Managing a demanding career while raising young children has given her a unique perspective on balance, time management, and the importance of asking for help when you need it. As she shared her story, it was clear that Jess isn’t just a tech leader—she’s a real-life example of how to juggle multiple roles while still showing up authentically.

Tackling Bias: A Call for Women to Embrace Their Strengths

As a passionate advocate for women in the workplace, Jess has had firsthand experience navigating gender bias, particularly in the tech industry. In one of her most impactful articles, The Real Reason Women Aren’t Getting Ahead in Tech: “She’s Not Strategic”, Jess shines a light on the frustrating stereotype that women who excel in operational roles are somehow not as “strategic” as their male counterparts. She’s seen how this bias can limit women’s upward mobility, even when they are making significant contributions to their teams.

Her advice to women in the workplace? Take on projects beyond your usual remit and nurture a strategic mindset. Jess encourages women to step outside of their comfort zones, even if it’s not immediately in their job description. She emphasizes that women’s strength in execution should be viewed as a strategic asset—not a limitation. For leaders, Jess advocates for looking beyond the labels and truly understanding the breadth of your team’s contributions.

Confidence, Public Speaking, and Leading with Empathy

Jess is also a role model for leadership in action. We were especially struck by her openness about how she built her confidence in public speaking and leadership, particularly when dealing with imposter syndrome. Known for asking insightful questions in meetings, Jess admitted that it took time for her to realize that this quality set her apart. In her early career, she was often nervous about speaking up in large meetings—but over time, she learned to “just send it.” She embraced asking questions, sharing her perspective, and owning her voice.

But what truly sets Jess apart as a leader is her emphasis on empathy. She believes it’s crucial to create a safe space for mistakes—not just for her team but for herself as well. As a leader, Jess owns up to her errors and encourages her team to do the same. This open approach to failure fosters a culture of continuous learning and growth, allowing everyone to move forward stronger and more resilient.

High Care, High Performance: Jess's Unique Leadership Style

One of the most striking aspects of Jess’s leadership style is her ability to balance high performance with high care. Sometimes, she’s been told she’s “too caring” for a corporate environment. But instead of viewing this as a weakness, Jess redefines what it means to care in the workplace. She believes that when people feel valued and supported, they’re more motivated to reach ambitious goals. Jess’s leadership is about psychological safety—creating an environment where people feel appreciated, understood, and inspired to perform at their best.

Staying close to her team’s daily operations is one of her secret weapons. Jess believes being hands-on helps her understand her team’s challenges, advocate for them effectively, and build trust with upper management. It’s this high care, high performance approach that has allowed her to lead successfully at StarTree.

The Executive Challenge: Mentorship, Trust, and Vulnerability

As a seasoned executive, Jess knows that leadership is about more than just running a department. It’s about influencing culture, making high-stakes decisions, and holding yourself accountable for the health and direction of the entire business. One of the most valuable lessons Jess has learned is the importance of mentorship. Early in her career, her former CMO, Tom Wentworth, provided the guidance and exposure she needed to gain confidence and navigate high-level strategy. Mentorship, Jess believes, isn’t just about learning the ropes—it’s about gaining the confidence to step into executive leadership and trust your instincts.

Trust is another critical element of high-performing teams, especially at the executive level. Jess reflected on how essential it is to build trust within leadership teams, particularly when navigating difficult decisions like layoffs or budget cuts. She emphasized the importance of addressing trust gaps and how doing so can be the difference between a company’s success or failure.

Vulnerability as Strength: Embracing Feedback and Building Team Connection

Throughout her career, Jess has learned to embrace vulnerability, especially when it comes to feedback. She encourages her team to view feedback as a gift—something that can be used to improve and grow. In fact, one of her most memorable team-building activities was a “Significant Emotional Experience” (SEE) around a campfire, where team members shared personal stories. This activity strengthened trust and reinforced the power of authentic, human connections in leadership.

At the heart of Jess’s leadership philosophy is the belief that being genuine and approachable can foster collaboration, build resilience, and ultimately drive success. By embracing her true self—both as a leader and as a person—Jess has cultivated an environment where her team can thrive, learn, and grow.

Final Thoughts

Jess Iandiorio’s journey is a powerful reminder that leadership is about much more than titles. It’s about creating the right environment for your team to succeed, making strategic decisions with empathy, and always striving to do better. Jess’s insights on mentorship, feedback, and leadership resonate far beyond the tech industry—they apply to anyone looking to lead with authenticity and compassion.

So, if you’re looking for a little inspiration or practical advice on building a strong, resilient team, this episode of WINK is a must-listen. Jess’s story proves that with confidence, compassion, and a willingness to embrace your true self, you can achieve incredible things.