Thriving Through Open Enrollment: Lessons from bswift’s Chief People Officer

Your caffeine intake triples. Your inbox triples. Your patience? Well, it’s probably not tripling.
It’s open enrollment season — HR’s annual enrollment Super Bowl, where strategy meets sheer endurance. 

For HR pros, those two words can make your eye twitch a little. It’s the flurry of questions, sometimes late nights, and too many spreadsheets that somehow still break. But what if open enrollment didn’t have to be a grind? 

What if it was less about survival and more about strategy — a moment to strengthen culture instead of just pushing through? 

We recently sat down with Natalie Atwood, Chief People Officer at bswift, on the bswift Beacon podcast. With a career that bridges operations and people leadership, she’s seen benefits from every angle. Her take: open enrollment doesn’t have to break you. In fact, it can build you. 

Build resilience: How does HR prepare for open enrollment? 

“Fix your roof when the sun is shining,” Natalie said. It’s her blueprint for leading her team, and thriving through the busiest season in HR. 

“For me, leadership is relationship and investing time in understanding and knowing the team that you’re working with — really understanding, knowing them as a person outside of just the workplace,” she explained. “What are their families like? What are their passions? What do they do when they’re not working?” 

The mad dash of open enrollment is sometimes just a symptom of deeper, year-round gaps. That’s why nurturing strong, trusting relationships throughout the year is so important. It builds a foundation of resilience that HR teams can rely on when “Super Bowl season” hits.  

That relationship capital is what carries you through. When people know you’re in it with them, they’ll give grace, collaborate faster, and take ownership instead of waiting for direction. 

Your Move: Don’t wait for the storm. The best time to plan for next year’s open enrollment is the week this one ends. Debrief while everything’s fresh — what worked, what didn’t, and where you can make it easier next time. Then, before the next season starts, invest real time in reconnecting with your team. That’s the most strategic prep you can do. 

HR communication strategies to strengthen company culture 

For Natalie, communication isn’t a soft skill — it’s a lever in the system that is your organization’s culture. And when you use that lever, it can help you transform your culture. 

Her approach comes down to three repeatable steps: 

1. Ask for feedback. “Trust me, if you ask people, ‘What’s broken?’ they will tell you,” she says. And be ready for the answers, too. Use surveys, focus groups, one-on-one check-ins — whatever opens the door to honest input. 

1. Actively listen and act. Listening is about taking in the feedback — the different ideas and directions employees propose — and creating a plan that moves forward and shows visible signs of progress employees can see. You don’t have to fix everything, but you do have to move the ball forward where it counts. 

1. Iterate and improve. Culture isn’t a one-time initiative. It’s a continuous loop of feedback, action, and follow-up. Each cycle builds more trust and engagement. “It is a process, it does take time, and we continue to level up and we continue to ask ourselves, ‘How can we make this better?’,” Natalie said. 

And when employees see their feedback leads to real change, they stop feeling like passive observers — passengers who are just along for the ride — and start feeling like owners who can drive progress for the organization. 

Leverage the right benefits tools to lighten the load 

When Natalie joined bswift, she discovered open enrollment was just two months away. Cue utter panic. 

Because bswift is a benefits administration services and solutions provider, the benefits plan year has always run in the off season — June to May instead of January to December — leaving her only a few weeks to prep for open enrollment.  

“I literally wanted to fall off my chair,” she admits. “My experience with benefits preparation and benefits, putting a company through annual enrollment was months and months and months of testing, building APIs, ensuring that all the connections were working, writing volumes of benefit books, testing, looking at it, wanting to make sure it looked good. And that is something that we did for six months out of the year.” 

But instead of chaos, she got calm. Her past experiences with all-in-one HRIS systems had conditioned her to expect a long, painful setup. But this time was different. 

“The bswift team stepped in, supported us with the system,” she recalls. “It was seamless. I was very much in awe — like, wait, what? It’s really this easy?” 

That moment drove home a truth every HR leader knows but rarely gets to live: your tools matter. When technology actually works for you, it gives you back time to do the real work — leading, listening, and connecting. You stop wrestling with data and start shaping culture. 

Lead with empathy during open enrollment 

Open enrollment will always be demanding. But Natalie believes how you show up during it defines your team’s experience. 

She leads from the trenches. If her team is working late, she’s right there with them. She ends every meeting with the same question: “Is there something I can do to support you better?” 

That kind of leadership doesn’t just get the job done — it builds trust that lasts long after the season ends. It also creates space for honesty: to say when things are hard, when something’s not working, or when someone needs a break. 

That kind of leadership doesn’t make the stress disappear, but building those solid relationships make the stress a shared challenge instead of a solo one. 

How HR shapes company culture through open enrollment 

At the end of the day, Natalie sees HR as the architects of company culture. Through that lens, open enrollment isn’t just a logistical hurdle, it’s an expression of organizational values. Through strategic leadership, relationship-building, and smart technology, HR can transform open enrollment into one of the clearest reflections of what’s going on in that culture. 

When people see that their benefits are handled smoothly, that communication is clear, that leadership shows up — it says a lot about what’s going on under the surface, and the kind of company this is. 

With the right mix of human connection and smart technology, open enrollment can shift from being a yearly headache to a strategic advantage — a moment where HR earns trust, deepens engagement, and demonstrates what great culture looks like in action. 

So, as you head into the thick of it, take a breath. You don’t have to white-knuckle your way through open enrollment. Because when your people trust you — and your technology actually works for you — you stop playing defense and start leading again. 

So, if the roof’s already creaking and the clouds are rolling in, take a note from Natalie: step back, listen to your team, and let a system built for HR actually carry some of the load. That way, you can focus on what matters most: your people. 

Because that’s the way benefits are meant to be. 

Takeaways for HR leaders 

Here are key takeaways from Natalie Atwood, bswift’s Chief People Officer, on how HR leaders can thrive during open enrollment and strengthen company culture. 

• Build strong relationships year-round to create “relationship capital.” 

• Use communication as a lever: ask, listen, act, iterate. 

• Lean on technology to free time for strategy and culture-building. 

• Lead with empathy to create trust and shared responsibility. 

• When your people trust you and your technology actually takes work off your plate, you can start leading again. 

Listen to the full conversation with Natalie Atwood on the bswift Beacon podcast for more HR strategy insights and open enrollment tips.