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Navigating the Unseen: Jess Vassallo’s Journey of Resilience and Advocacy
In the world of business, success is often measured by numbers—revenue, growth, expansion. But for Jess Vassallo, CEO and Founder of Evocative Media, the most significant numbers in her life have been ones that don’t appear on a balance sheet. The number of times she’s faced loss, the number of days spent hoping, and the countless moments of quiet resilience that have defined her journey with infertility and recurrent miscarriage.
Jess Vassallo is a woman who has built her life and career on the foundation of hard work and determination. She is someone who, by her own admission, has achieved much of what she set out to do—except for one thing. For six years, Jess has endured the heartache of trying to conceive—a journey defined by several rounds of failed IVF, multiple surgeries, countless doctor visits, and the devastating loss of four pregnancies, most of which occurred in just the past two years.
“Hard work has always been my way of navigating life’s challenges, but this... this is a journey where, regardless of how hard you work at it, it doesn’t dictate the outcome,” Jess reflects.
It’s a sentiment that echoes the experiences of many women, yet it’s rarely discussed openly, especially in the workplace. Jess’s journey is one of the estimated 1%—the women who have experienced recurrent miscarriage. But it’s also a journey that many more can relate to, even if they’ve never spoken of it.
In her role as a leader, Jess has always championed the importance of prioritising health, family, and personal life. “I’ve always believed in supporting my team through life’s challenges, but when I faced my own, I realised how unprepared I was to extend that same support to myself,” Jess admits.
In August 2023, Jess experienced her third miscarriage—a loss that came on a Thursday. By Monday, she was back at work, leading her team and pushing forward.
“It was the first time I felt resentment toward the business I had built. Not for the work itself, but because I hadn’t allowed myself the space to heal, to grieve. That moment forced me to rethink everything.”
But change is not linear, and neither is the journey to motherhood. After just a few months, Jess found herself pregnant again. During her fourth pregnancy last year, she heard a healthy heartbeat, and for a moment, hope returned. “When I heard that heartbeat, it gave me so much hope—I felt such joy in that moment,” she shares. But weeks later, that hope was shattered by another miscarriage. The pain was immense, both physically and emotionally, and Jess found herself once again throwing herself into work as a way to cope. “The grief was profound, but if this experience has taught me anything, it’s that it’s okay to not be okay. I’ve learned that healing isn’t about forgetting the pain, but finding the strength to walk through it.”
Throughout Jess's journey, and because of her position as a Founder & CEO, she was able to take leave whenever needed—whether it was for an appointment, rest after IVF, or other necessary breaks. “Last year alone, I had more than 70 acupuncture sessions. I was going to those appointments daily for months as part of a treatment plan, which meant I was often late into the office every day or ducking out for long appointments,” Jess reflects. “Thinking back to when I worked in a corporate job, I can’t imagine asking for that much time off...”
However, she began to reflect on what this meant for her team if they were to experience the same thing. This insight led her to reassess how her company supports employees facing similar challenges, recognising the importance of providing the necessary time and space to heal.
Jess’s journey has been one of shared resilience. Her husband, Kain, who is also deeply involved in the business, was profoundly affected by the losses they endured. Yet, like Jess, he continued to show up and push through work, demonstrating a quiet strength that often goes unnoticed in the face of personal tragedy.
As the newest Ambassador for Pink Elephants, Jess is channelling her experiences into advocacy and action. She understands that pregnancy loss at any stage is not just a medical event; it’s a deeply personal and often isolating experience that affects every aspect of a woman’s life. With one Australian woman experiencing a miscarriage every five minutes, the need for support has never been greater. Jess is determined to break the silence that surrounds miscarriage and infertility, to create environments—both in the workplace and beyond—where women can share their stories, receive support, and know that they are not alone.
“Two days of paid leave doesn’t even begin to address the profound impact of miscarriage. The physical recovery is just the beginning—the emotional and mental toll extends far beyond that. Grief has a way of resurfacing on due dates, anniversaries, or when you least expect it. Flexibility in how and when leave can be taken isn’t just compassionate; it’s necessary.”
Jess advocates for changes that would allow for more comprehensive and flexible leave policies, recognising that as a CEO, she has the autonomy to take the time she needs, but her employees may not. “We need to create environments where taking the necessary time to heal is a right, not a privilege,” she asserts.
“Through programs like Pink Elephants’ workplace initiatives, companies have the opportunity to lead the way in creating supportive environments that acknowledge the full scope of what their employees might be going through. This isn’t just about policy; it’s about changing the culture, making it one where empathy and understanding are at the forefront.”
The challenges Jess has faced have deepened her commitment to leading with empathy, a quality she has always prioritised in her leadership style. “Leadership, to me, has always been about more than just steering the ship towards financial success. It’s about creating a culture where people feel seen, heard, and supported—especially when life doesn’t go as planned.”
At Evocative Media, Jess has implemented a policy of 10 days of paid leave specifically for those dealing with miscarriage, early pregnancy loss, fertility challenges, and family planning, with the option to extend this paid leave if needed. “The standard two days of leave simply doesn’t address the full impact of these experiences,” Jess explains. “We’ve designed this policy to give our team the flexibility to take the time they need, whether it’s right after a loss or during the ongoing process of healing.” Additionally, Jess has introduced a policy allowing flexibility for family planning appointments, recognising that using up paid leave for these critical moments isn’t fair.
“A person’s desire to have a family shouldn’t require them to deplete their paid annual leave. No one should have to sacrifice their earned time off simply because they’re taking necessary steps to build a family.”
Pink Elephants is proud to welcome Jess Vassallo as an Ambassador, knowing that her voice, experience, and passion will drive meaningful change. Jess’s commitment to bringing Pink Elephants’ workplace program into full view reflects her deep understanding of the need for compassionate and comprehensive support systems. Through her advocacy, Jess aims to create workplaces where every woman feels seen, supported, and empowered, particularly during the most challenging times. Her leadership and determination are not just inspiring—they are a call to action for companies everywhere to rethink how they support their employees, ensuring that empathy and understanding become cornerstones of corporate culture.
We Are Here. No Matter Where You Are.
For those currently struggling with the pain of miscarriage or early pregnancy loss, Pink Elephants offers a range of support online and over the phone.
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