What makes a company a true role model for women in leadership? For Sigal Gillmore, chief human resources officer at Check Point Software Technologies, the answer begins at the top. “It starts from the top,” she said in a conversation with Anna Ahronheim during the recent Jerusalem Post Women Leaders Summit 2026, pointing to a legacy of female leadership embedded “from the very early days.”
Today, that legacy is reflected in women holding 25% of executive roles and nearly half of board seats, figures that prompt a deeper question: how do organizations turn values into sustained outcomes? Part of the answer lies in long-term investment. Check Point’s women-in-technology leadership program, now over a decade old, focuses on development, exposure and mentorship. Its success raises broader questions: can structured programs truly shift leadership pipelines? And what happens when former participants return to mentor the next generation?
The conversation then turned to a more immediate reality: leading through war and how companies stay connected to employees under constant stress. “Communication, communication, communication,” Gillmore stressed, describing daily check-ins that begin not with business, but with people. “We look at the person first, then the family, and then the business.”
Yet this approach raises a critical tension: how do organizations balance empathy with continuity? For Gillmore, resilience lies in holding both. Supporting employees through mental health services, flexibility, and community, while ensuring the business remains strong and stable. That balance becomes even more complex in the age of AI. “AI is basically a machine trained by people,” she noted. At Check Point, she explains, the goal is to harness AI responsibly: improving efficiency while maintaining fairness and security. But as AI reshapes roles, another question looms: will it replace jobs? Gillmore’s answer is pragmatic. Some roles will change, others will emerge, but “we’re always going to have a mix of human and machine.” This shift requires organizations to continuously adapt skills and rethink how work is structured. The future, she suggests, will depend not just on technology but on the human judgment that guides it.
Written in collaboration with Check Point