Early in my time at beehiiv, I realized we needed to join a Professional Employer Organization (PEO) to secure better insurance rates. Despite being in the early stages, we had a more mature staff, and that, combined with NY community pricing, led to high premiums. Rightfully so, no one was a fan.

As we approached our enrollment period, we were in a precarious position as we transitioned from marketplace rates to PEO-support premiums. I was excited about the promise of potentially bringing employees better rates, and possibly sooner than the enrollment period. As I mentioned, we were overlapping in timing, and so we had the option to pull forward these newer rates. However, there were many considerations, especially for those who had already met the deductible. We kept running analyses of how we should approach this. In theory, this sounded great for employees, right?

Transparency has always been integral to how we run the company, and given that we were still making assumptions about usage, I thought this might be a perfect opportunity to try something different. We were small enough to still meet in small groups, and so, I figured we could clarify the details and present the company with two options to reach a general consensus. Yeah, I was wrong. Very wrong.

No consensus was made, and I felt like I had egg on my face.

Despite the embarrassment, a few coworkers reached out directly to thank me for trying something different. They mentioned they had never seen People Ops attempt what we did and appreciated the thoughtfulness, even if the outcome was disappointing (to me).

I’m not kidding when I say that it slightly brought me to tears, just because of how stupid and defeated I felt. Despite that, someone noticed I was trying, and that really mattered to me. Thanks, Tony 🙂

So, we scrapped the initial idea and just defaulted to the original timelines 🤷‍♀

We didn’t try this again, but I’m glad we did. This also gave me the courage to keep trying different things and to figure out what worked best for our company, rather than just doing what had been done before because “that’s just what we did.”

When we talk about culture and engagement, it can feel a bit formulaic, even cold. We’re fortunate to have maintained that small-company energy, especially as we scale. While this was a boo-boo, it could’ve been worse.

As professionals, we often make assumptions about how people will react or interpret our intentions, especially when our decisions have an impact. Maybe I’m an idealist, but top-down or bottom-up, we have to remember that we’re all trying to connect the dots, build something cool, and have some fun.

So, to recap:

The AI for Business & Finance Certificate Program from Columbia Business School Exec Ed and Wall Street Prep draws on real-world examples inspired by how firms like BlackRock, Citi, and Morgan Stanley approach AI enablement for their teams.

You’ll go beyond theory to understand what’s being implemented, why it works, and how to apply it in your own role.

Save $300 with code SAVE300 + $200 with early enrollment by Feb. 17.

Enroll Today

It’s okay if you’re sad or going through SAD.