Leading With Heart: How Michelle Whittaker Sparks Confidence and Connection

Within InvoiceCloud’s mid-market CSM team, Michelle Whittaker is known as its “heart and soul”—a leader whose influence is felt not just in outcomes, but in the culture she cultivates. For Michelle, that culture begins with relationships. “Creating a strong team culture starts with nurturing genuine connections,” she says. “I lead with transparency, listen to understand—not just to respond—and celebrate others’ successes as if they were my own.” That commitment to making people feel “seen, heard, and valued” is, in her words, “the heartbeat of any great team.”

Yet Michelle is quick to credit the foundation that enables her leadership to flourish. She emphasizes the importance of having a leader who fully supports both her and her management style. “That kind of backing fosters trust, empowerment, and alignment,” she notes. “And I’m grateful to have that support.” It’s a reminder that great leaders often grow in environments where they themselves feel empowered.

A Personalized Approach to Mentorship

This relational approach shapes how Michelle mentors others as well. Whether guiding new employees or experienced team members, she adapts her style to meet people where they are. “Mentorship isn’t one-size-fits-all,” she explains. “New employees often need confidence and clarity, while veteran team members benefit from space to grow and lead.” Over time, she’s learned that empathy and adaptability are essential to helping others succeed—qualities her colleagues frequently recognize in her day-to-day leadership.

Michelle’s ability to tailor her approach has had lasting impact on her team. She recalls one colleague who initially felt intimidated in the workplace. Through steady encouragement and patience, she helped him not just perform, but believe in his own capabilities. “He knows I’m in his corner, no matter what,” she reflects. “That sense of unwavering support empowered him to thrive professionally and personally.”

Balancing Strategy with Service

Balancing her leadership responsibilities with her own customer portfolio is no small task, yet Michelle’s philosophy helps her stay grounded. “To me, customers are the strategic priority—whether they’re in my portfolio or someone else’s,” she says. Staying close to both the team and the clients ensures alignment and responsiveness, even when it requires extra hours. “The balance comes from staying focused and being flexible with my time.”

Making an Impact, One Relationship at a Time

One of Michelle’s most meaningful accomplishments at InvoiceCloud was managing 102 accounts—an intense workload by any standard. But for her, the true achievement was not the number itself; it was the relationships she built along the way. “It wasn’t just about volume—it was about connection,” she says. Watching her team grow, deepen their customer relationships, and gain confidence has been “the most fulfilling part of the journey.”

Creating a Culture of Empowerment

Empowerment is another cornerstone of Michelle’s leadership. She creates space for ideas by listening deeply, asking thoughtful questions, and helping her team understand the “why” and “how” behind decisions. “When people understand the impact of their contributions and feel trusted to own them, they step into leadership naturally,” she explains. “Empowerment is built on trust, clarity, and support.”

Leading With Integrity and Intention

When asked what advice she would give to other leaders, Michelle emphasizes integrity and intentionality. “Respect isn’t demanded—it’s earned through consistency, empathy, and authenticity,” she says. “When you show up for your team with purpose and humility, collaboration becomes second nature.”

Being Seen—and Inspiring Others

Receiving the Women Who SPARK Award holds deep meaning for Michelle—both personally and professionally. “Being seen and appreciated for who I am feels deeply rewarding,” she shares. She hopes that her leadership encourages others to embrace their individuality rather than conform to expectations that don’t reflect who they truly are. “I want people to recognize the unique strengths in their teams and uplift one another with intention and care.”

In every facet of her leadership, Michelle Whittaker exemplifies what it means to lead with heart—proving that when people feel supported and valued, they not only succeed, they soar.