Dave Wynne is an experienced finance and operations executive with broad industry knowledge, especially in the technology, e-commerce, and manufacturing space. He currently leads the finance team at Boxed across strategy, accounting, business operations, and payroll. In our Q&A, he shares his best practices for closer collaboration between HR and finance teams and additional helpful insights.  

Can you tell us more about Boxed? 

Boxed is a mobile-first technology and e-commerce company that sells grocery and home goods to individuals and families across the country. We typically sell in bulk to enable us to provide incredible value, and we deliver a unique, dynamically personalized user experience to make sure customers never run out of the things they need for home, work, and life.

What’s the most rewarding part about your job?

I wake up excited to help our customers thrive — to make life less stressful, to deliver incredible value, and to make things as easy and convenient as possible.

In my role, it’s extremely rewarding to provide financial and strategic leadership, business analysis support, and executional expertise to every department so we succeed. One pillar of that work entails the partnership of the finance and people teams, and how we together support the health and wellness of our employees. 

What's the most misunderstood part about your job? 

There are a lot of stereotypes about “finance” in companies of all types. The basic message I share with colleagues is that working at a company means working with humans, regardless of department. We all seek compassion and support; we're all activated when engaged intellectually; and we all operate in our roles with good intent.

The most misunderstood nuance about finance is that we're not gatekeepers. We're actually gate builders who seek to create order out of the chaos, navigating a thousand different decisions about where and how to invest in growth, people, and opportunities.

You work in a unique position of overseeing finance at Boxed, but also having co-led your company’s benefits renewal strategy. How have those roles informed each other?

I spent nearly five years at The Riverside Company, a private equity firm with $7 billion under management that owns 75 companies around the world. For nearly three years, I had a unique internal strategy role with a mandate to make Riverside better at both investing in and working with companies.

Part of my efforts included advising and supporting HR executives across the U.S. on benefits and wellness. Together, we navigated the impact of plan designs and moved away from “cadillac” plans to put education into the hands of employees; introduced high deductible health plans (HDHPs) and health savings accounts (HSAs); delivered wellness programs to improve “whole health;” and took a strategic approach in leveraging healthcare as a component of the employee experience.

My years spent with HR executives enabled me to be a better investing professional, and later helped me become a powerful ally to people team leaders. At Boxed, this has translated into a collaborative way for us to evaluate decisions about annual renewals and enabled a powerful partnership between the finance and people teams as we map out the next two to four years to deliver more support to employees.

We already have unlimited vacation, unlimited maternity and paternity leave, and benefits for employees who get married and who are parents with college-aged children. Delivering new value to everyone in a direct way to support their whole health has been an important strategy as we continue to build a portfolio of support for our employees.

What are your recommended best practices to have HR and finance teams work more closely together?

Basic advice is that the best time to talk about benefits is right after a renewal and not right before a renewal. The ideal scenario is for the people and finance teams to develop a three to five year plan and then work to execute on that plan together. Unfortunately, it’s much more common for the first real meeting to be “we need to make a decision soon or now.” 

“The ideal scenario is for the people and finance teams to develop a three to five year plan and then work to execute on that plan together.”

David Wynne
Boxed

On that note, I encourage everyone to consider the following:

• For people teams: your finance team counterparts can help you think about the “portfolio” of tools and services to offer and can assemble analyses to determine the cost and benefit of any combination of benefits. Finance has a very broad perspective given that they have continuous dialogues with all team members and can provide strong long-term planning competency.
• For finance teams: consider that your people team counterparts are deeply connected with the employees. Employees come to them with their hopes and worries, and they rely on them for expectations to be set and met . 

It’s exciting to hear that Boxed just introduced a HDHP with an HSA for the first time! Can you share more about this transition? 

We're very excited to offer an HDHP to our employees. We have a diverse population of employees, and it’s challenging to serve up plans that make sense for everyone! The main reasons we introduced the option are because:

• Having an HSA is a powerful tax-advantaged way for employees to accumulate savings that can be used any any stage of their life, whether it's at Boxed or when they're retired!

• An HDHP generally has lower premiums and can be more affordable for both employers and employees. It can also be a powerful fit for healthy people who need the protection “just in case” and allow families to do real financial planning.

• We've found that employees with HDHPs generally are more active participants in their healthcare experience and become more knowledgeable as a result. An engaged population is consistently better for all parties.

For a smooth transition, we conducted “all hands” sessions explaining what’s the same and what’s new. We’ve also made ourselves available for any and all questions. We’ve seen record enrollments with this open enrollment and are very excited that over 25% of employees adopted the new high deductible option!

Everything considered, it’s hard to deliver a smooth experience. We don’t live and breathe this everyday, so we plan to investigate new opportunities in advance of our next renewal. Amino is high on the list of potential partners that can empower our company to best serve our employees and to provide them with more data, insights, and services to really have the confidence to make the right decisions for their health, life, and bank accounts.