As Chief People and Business Officer of Outreach, Leslie Pendergrast sees everyone as a leader, regardless of job title. That idea now informs hiring, training, development, and performance management across the company. Pendergrast has also prioritized a more holistic approach to diversity, equity, and inclusion, treating it not as a side initiative but as a fundamental layer of all people operations. “Practices have to authentically match the culture,” she notes, “because they drive how people behave.”
Pendergrast grew up in Florida and earned a bachelor’s degree in communication from Florida Atlantic University, followed by an MBA in business from Nova Southeastern University. Her career in HR began at Citrix Systems, where she served as Vice President of Human Resources. She went on to lead HR teams at Sourcefire, Datalogix, Vibrant Organizations, and Code42 before joining Outreach in 2020. In her current role, she oversees global HR, talent development, leadership frameworks, and employee experience.
She’s especially attuned to the evolving demands of remote and hybrid work. Rather than enforce rigid policies, Pendergrast emphasizes psychological safety, flexibility, and continuous listening. She has rolled out new wellness tools, coordinated time-off programs, and pulse surveys to better support employees across time zones and job functions. For her, creating a strong workplace culture means designing systems that assume good intent, offer autonomy, and support people as whole individuals. “You don’t always know what’s going on at home for your employees,” she says—so trust and flexibility aren’t perks, they’re essentials.