Redirecting.work

But despite shifting from the structure of a large consulting organization back into entrepreneurship, she does not experience her journey as a dramatic reinvention. Instead, she sees it as a continuation of a worldview she has been developing for decades. “I feel like the world is catching up to a direction I’ve been going for 23 years,” she said. Let’s hope so, as her implicit vision is stunning.

​

What She Pivoted From

Mercer acquired Leapgen in 2023, the digital transformation consultancy she helped build alongside longtime collaborator Jason Averbook. The acquisition made strategic sense. She believes Mercer gained exactly what it sought: a strong digital transformation capability and a new way of thinking about work. She has now left Mercer after giving it what they promised.

​

She thinks the AI moment accelerated faster than traditional consulting structures can comfortably move. “The bigger you are, the more structured and hierarchical,” she said. “Nobody can move fast enough for this moment.”

​

After fulfilling her commitments, Jess and Jason launched Now to Next, a new advisory firm focused on helping organizations navigate AI-driven transformation. For Jess, the move is not about escaping corporate life as much as it is now having the freedom to respond more directly and creatively to a historic shift in how work is being redefined.

​

Underneath the career move is a deep through-line. Over years of working at the intersection of people, technology, and transformation, Jess developed a growing belief that many systems of work were built around extraction rather than human flourishing.

​

“We don’t know how to value the whole person,” she says.

​

The Transition Process

Jess describes her transition process as one of “building out loud.” Rather than waiting until everything was polished or certain, she is experimenting publicly, writing constantly, and sharing proof of work as permission and an on-ramp for others. Using AI as a thinking partner didn't help her discover new values; it reinforced ones she'd been carrying so long they'd stopped feeling like a choice. 

​

While teaching Claude to “think like her,” she finds herself clarifying her own beliefs and priorities. The exercise is revealing how deeply purpose-driven she is and how committed she remains to elevating women and redesigning work around more human values.

​

“I realized I would literally do anything to elevate women and girls and to change work so that it’s not an extraction,” she said.

Relationships played an important role. Jess has long relied on what she calls a “personal board of directors,” a diverse group of trusted advisors who help her evaluate opportunities, risks, and decisions. Jason Averbook is one of her longest-standing collaborators, but she also intentionally seeks perspectives outside her own industry and worldview.

​

Current Direction

Today, Jess’s work centers on helping organizations redesign work from the starting point of AI. Through Now to Next, she and Jason Averbook guide companies through transformation processes that address not only technology adoption, but also identity, culture, leadership, and human participation.

​

She believes traditional transformation models are no longer enough for this moment. AI is not simply another technology rollout. It’s forcing organizations and individuals alike to rethink value, contribution, productivity, and what it means to work.

​

The Now to Next framework includes “heartset, mindset, skillset, and toolset.” She argues that organizations must address emotional resistance, ethical concerns, and questions of identity if transformation is going to succeed.

​

Her worldview is shaped by deeply personal influences. Jess reflects on her grandmother, who raised nine children, never held a formal paying job, or a driver’s license for that matter, and yet “was just the boss.” She credits her grandmother with teaching her not to wait for permission or external validation.

​

That philosophy informs Jess’s broader vision for redesigning work. Through concepts like reciprocity, caregiving, and what she calls “maternal systems thinking,” she wants organizations to rethink how humans participate in systems of work. “I would absolutely beg us to redesign systems with more women’s voices,” she says. Jess is not simply critiquing existing systems. She is helping build alternatives.

​

At the center of her thinking is a manuscript she began writing over Thanksgiving weekend called Work Like a Mother. The title isn’t about motherhood in a narrow sense. It’s about bringing more caregiving, reciprocity, development, and human-centered thinking into systems that were largely designed through industrial and transactional models.

​

Jess doesn’t frame this as anti-male. Instead, she sees it as introducing more maternal and reciprocal ways of thinking into organizations and leadership systems that often prioritize extraction, speed, and hierarchy over humanity.

​

Her goal isn’t simply to critique what’s broken. It’s to help build something better. “If AI is going to transform work,” she said, “then we have to redefine how humans participate in that system.”

​

Advice to Others

Be imaginative: Jess encourages people to approach this AI moment with curiosity rather than fear. “This is an imagination moment.” 

​

Be opportunistic: She believes individuals should think opportunistically about how technology can expand the “surface area” of their value and contribution rather than assuming they’re becoming obsolete. 

​

Be more analog: Look at young people. “Go see live music. Put your feet in the grass.”

​

Build your own voice: Don’t wait for permission. This future belongs to storytellers. Become one for yourself.

​

Be more human: At the same time as you use technology, remain deeply human and intentional.

​

Her hope is that AI eventually gives people something many modern workplaces have steadily taken away: time. “The most radical thing AI can do,” she says, “is give people time back to just be.”