How Insurance Companies Create Effective Flexible Work Environments

The insurance industry isn’t typically known for blazing trails in the future of work. Traditionally steeped in brick-and-mortar operations, it has often lagged behind more agile sectors when it comes to embracing distributed work models. But The Penn Mutual Life Insurance Company is proving to be a progressive company gaining great benefits from outcompeting its rivals. In a wide-ranging conversation with Liz Heitner, Chief Human Resources Officer at Penn Mutual, it became clear that a thoughtfully designed flexible work strategy can not only succeed in insurance—it can thrive.

Anchoring Culture in Flexibility 

Penn Mutual didn’t stumble into remote work—it leaned into it with conviction. As Heitner explains, the company became a fully flexible, remote-first organization during the pandemic and has never looked back. Unlike many peers who made tentative forays into hybrid setups only to call employees back to headquarters, Penn Mutual committed fully to remote work across the lower 48 states.

This wasn’t just a reactive decision—it was a cultural affirmation. The organization prioritized employee well-being and trusted its workforce to deliver, rather than insisting on proximity. “We saw a huge improvement in productivity,” Heitner noted, attributing it to earlier tech investments and a collaborative spirit that seamlessly carried over to virtual settings.

The results are compelling. Employee engagement remained high, with the company making a genuine effort to gather feedback through a close partnership with  Great Place to Work. Most strikingly, Penn Mutual has managed to sidestep two of the biggest HR headaches of recent years: the Great Resignation and the pressure to escalate compensation in a fiercely competitive labor market. By offering a flexible environment and clear cultural expectations, they’ve attracted and retained top-tier talent from across the nation.

Managing the Emotional Undercurrents of Change 

Transitioning to a fully remote structure isn’t without emotional weight—something many companies overlook. Penn Mutual recently decommissioned its former headquarters, a building filled with professional memories. Heitner spoke candidly about the grief some employees felt as the company moved on from its physical legacy.

Rather than brushing these feelings aside, the company made space for conversation. Leaders acknowledged the grief and helped employees focus on what truly defines Penn Mutual: relationships, not real estate. This level of emotional intelligence underscores the company’s approach to change—not just managing logistics, but guiding people through transformation.

Redefining Leadership for a Distributed Workforce 

One of the most common reasons companies cite for reversing remote policies is that their managers struggle with it. Penn Mutual took a radically different approach: it invested deeply in leadership development tailored to remote work.

The company launched a targeted initiative called “Lead Stronger,” which equipped leaders with frameworks for effective communication, intentionality, and team engagement. Managers learned to structure meetings thoughtfully, listen more, and guide their teams with clarity and purpose. This wasn’t training for training’s sake—it was tied to concrete metrics and followed up with coaching and feedback loops. Leaders were expected not only to drive performance but also to cultivate a sense of connectedness across teams.

Heitner emphasized that Penn Mutual’s success is rooted in the quality of its leadership culture. Their leaders genuinely care about their people, and that ethos has enabled them to adapt, evolve, and ultimately excel in a virtual-first world.

Onboarding as a Team Sport 

While many companies flounder when it comes to integrating new hires into remote settings, Penn Mutual has turned onboarding into an area of competitive strength. With retention rates for new hires remaining high, Heitner attributes this to a team-based approach to welcoming employees. The process is tailored, intentional, and monitored closely.

From day one, new hires are introduced to Penn Mutual’s culture, business priorities, and performance expectations. Workday implementation has streamlined the administrative side, but the real differentiator is the human element. Managers and teams work together to ensure each new hire feels welcomed, supported, and seen. Milestone celebrations at 30, 60, and 90 days bring fun into the experience while reinforcing cultural integration.

Continuous feedback from new hires drives improvements. This adaptive mindset ensures that onboarding evolves in real time, not just annually during reviews. In an industry known for long learning curves, this kind of onboarding support is more than a nice-to-have—it’s a strategic asset.

The Future of Flexible Work in Insurance 

While many companies are tightening their grip on office mandates, Penn Mutual remains resolute in its vision. Heitner is clear: remote work isn’t right for every company, but for those with the right conditions—strong leadership, collaborative culture, and strategic tech investment—it can be a game-changer.

Penn Mutual is also looking ahead to emerging disruptors, especially Gen AI and asynchronous collaboration tools. Their recent implementation of Microsoft 365 is just one step in a broader journey of tech adoption designed to keep the company competitive and agile. “Organizations that don’t embrace these tools will fall behind,” Heitner warned, adding that a growth mindset and willingness to experiment will define the next wave of winners in the distributed work economy.

As the insurance industry navigates this turning point, Penn Mutual stands as a compelling example of what’s possible when flexible work is approached not as a contingency plan, but as a long-term, people-centered strategy. The company’s ability to maintain high performance, deepen employee engagement, and recruit top talent across the country offers a template not just for insurers, but for any organization reconsidering its future of work.

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