Hello Andy, welcome to HRTech Cube! Can you please share your professional journey and what inspired you to co-found When?
I am a serial entrepreneur, having previously co-founded two technology startups that were later acquired by public companies. The latter company, ApartmentJet was acquired by Expedia Group. During the Covid pandemic, I experienced a layoff firsthand and it motivated me to create a better offboarding solution, When.
The idea for When was conceived by my co-founder and next-door neighbor, Dan Wertheimer, after he lost his job while pursuing his MBA at Chicago Booth. His health insurance premiums jumped from $50 to $800 a month! Dan quickly realized he wasn’t alone in being shocked by this unexpected increase in monthly expenses. This experience led him to develop a business thesis on creating a new employee benefit to help cover health insurance costs during job loss. Dan submitted the thesis to the New Venture Challenge, one of the largest business case competitions in the world, run by the University of Chicago. While the idea received great feedback, Dan didn’t have a team in place to bring it to life. Fast forward 10 years, when I was laid off from Expedia Group, and for the first time, I understood the pain of being laid off and having my monthly insurance bills jump dramatically when I switched to COBRA. That’s when Dan and I decided to start When.
How do you see AI revolutionizing the employee experience, particularly in streamlining benefits, compliance, and HR processes?
AI is poised to drastically improve the employee experience by injecting efficiency, personalization, and scalability to benefits, compliance, and HR processes. AI has the ability to personalize and tailor benefits packages that align with employees’ individual needs, providing 24/7 always-on assistance, and simplifying benefits enrollment by guiding employees step-by-step through the process. AI platforms can foster greater compliance through tools like real-time monitoring, corporate policy updates and audit automation. And, we’re seeing greater use of AI to automate HR processes from onboarding, performance reviews, payroll processing and offboarding. I expect to see AI continue to transform HR by creating employee experiences that are more proactive, data-driven and employee-centric. By taking the administrative burdens off of HR professionals, they can focus on driving more strategic initiatives to enhance workplace culture and the employee experience.
What role does AI play in enhancing employee engagement and satisfaction in today’s workplace?
AI is more than a tool, it’s a catalyst for creating a workplace where employees feel heard, valued, and supported. AI plays a transformative role in enhancing employee engagement and satisfaction by enabling personalization, improving communication, and streamlining workplace processes. By leveraging AI, organizations can build stronger connections and feedback loops with their employees throughout various stages of their careers. AI can help employees feel heard, valued, and supported throughout all stages of their employment lifecycle, from onboarding to performance reviews and offboarding.
Why is providing accessible health insurance options becoming more critical in the current regulatory and economic climate?
The cost of healthcare is increasing across the board and companies are faced with absorbing not only the higher costs, but increasing compliance requirements. Inflation and financial pressures make affordable health coverage essential for employees, while employers must balance competitive benefits with budget constraints. Additionally, workforce expectations have shifted, with employees valuing benefits like portable health insurance during job transitions or layoffs. Accessible options not only help employers attract and retain talent but also ensure that employees have the support they need in a dynamic job market, reinforcing trust and stability in the workplace.
How should companies adapt their healthcare strategies in response to evolving regulations?
Employer-sponsored healthcare is a cornerstone of the U.S. insurance system, with roughly 50% of people relying on employer-provided healthcare as their primary source of insurance. Adapting healthcare strategies to align with evolving regulations requires companies to be proactive, flexible, and employee-centric. Employers should work with HR consultants and benefits providers to interpret new regulations and implement compliant strategies. Tailored benefits, telemedicine, and wellness programs are growing trends as companies strive to meet employee needs while managing costs amidst evolving regulations.
What are some cost-effective strategies companies can use to manage offboarding while maintaining a positive relationship with employees?
Providing comprehensive transition resources and personalized guidance, including AI-powered assistance for healthcare plan options, career support, and severance, can save millions of dollars for companies. For one of our clients, the company’s leadership observed shortcomings in traditional offboarding practices and recognized the need for more individualized support for departing employees. Their empathetic values demanded an innovative solution that balanced cost management with compassionate offboarding. Partnering with When saved this company a projected $1.4M from exits that occurred within a 3-month period, while also setting a new standard for employee care during transitions. The client is saving about $5,624 per exiting employee and $23,947 per employee who converted away from COBRA. This proves it is possible for companies to approach offboarding in a way that is cost-effective, compassionate and a net positive for the employers’ reputation.
How can businesses balance economic constraints with the need to support employee retention during workforce transitions?
Companies need to start considering the real impact of turnover, both from a human and a cost perspective. Layoffs don’t just impact exiting employees; studies show that remaining employees experience declines in job satisfaction, organizational commitment and job performance. Much of this is attributed to witnessing how their former team members are treated on their way out. To combat this, employers should invest in a comprehensive solution for offboarding that provides information, support, and tools to help everyone successfully navigate their job transition and protect the company’s brand. By utilizing a modern severance and retirement solution, employers benefit from cost savings by incentivizing alternatives to COBRA, providing flexible reimbursement amounts to align with severance packages, and providing early retirement health insurance solutions for pre-Medicare retirees.
What personal strategies do you rely on to navigate the challenges of leading a company in today’s complex business environment?
I focus on fostering a transparent and fast-paced work culture. From personal experience, I’ve seen how a lack of transparency can demotivate employees when they’re kept in the dark about the state of the business. That’s why I prioritize ensuring that everyone has a clear understanding of both our progress and challenges. This approach not only builds a sense of ownership but also alleviates the anxiety that comes from uncertainty.
On the fast-paced front, I strive to minimize bureaucracy and avoid over-engineering solutions. As an entrepreneur, I value output over lengthy discussions and over-analysis. Creating a culture that emphasizes action and results helps maintain momentum and keeps the team focused on driving meaningful outcomes.
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What advice would you give to HR leaders looking to leverage technology to improve both employee experience and organizational efficiency?
My biggest piece of advice for HR leaders is to invest in the employee offboarding experience in the same way you would invest in onboarding. While technology is becoming more commonplace as a tool to enhance the employee experience, it is not being leveraged consistently across the entire employee lifecycle. Time and time again, I hear stories of unsupportive exit experiences, to the point that it has become clear that offboarding is simply not a priority for many employers. This is a mistake that can have significant repercussions for organizations. The modern workforce is far more likely to take to platforms like LinkedIn and social media to voice their experiences with former employers. Companies should understand the potential for reputational harm and how that impacts their employer brand. The saying, “‘last impressions are lasting impressions” has never been more true.
What are your final thoughts on the future of HR, particularly in leveraging AI and other innovations to create more resilient organizations?
AI is poised to create a sea change in the HR profession – as it is in many areas of business. I see AI having most impact by personalizing employee experiences, enhancing decision-making, and streamlining administrative tasks. AI empowers HR teams to predict workforce trends, improve talent management, and support employees through transitions with data-driven insights. As workforces become more dynamic, tools that integrate AI will enable companies to adapt quickly, foster engagement, and deliver meaningful support at every stage of the employee journey. Embracing these technologies will not only strengthen organizational resilience but also create a more empathetic and effective approach to workforce management.
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