How startup leaders are navigating the new normal of remote and hybrid work

Remote work may be here to stay, but that doesn’t mean startup leaders have figured it all out.

One session at the 2025 Technical.ly Builders Conference tackled the question of how startups can balance the flexibility of remote work with the need for culture-building and engagement.

Titled “Remote vs. Hybrid for Startups: Recruiting & Ecosystem Engagement,” the session featured Raymond Magee of BloomCatch, Jake Stein of Common Paper and Dan Winston of BalancedWork, with Tally Wolff of Arlington Economic Development moderating.

With a mix of fully remote, hybrid and in-person experiences among them, the panelists offered candid insights about what’s working — and what isn’t — in this evolving era of work.

“There are things we got for free in person that we didn’t appreciate until they were gone,” Stein said. “Bumping into each other, building rapport so you give someone the benefit of the doubt on an ambiguous Slack.” 

One key theme was how founders engage with their local startup ecosystems.

Magee pointed to the conference itself as a powerful example: In-person gatherings offer value that remote work can’t replicate, but the fact that sessions are recorded makes them more accessible to founders who can’t make the trip.

“If you can’t physically drive … three hours to get this knowledge firsthand and in person, the ability to watch the recording is key,” Magee said. “Hybrid and remote work have changed how we engage in conferences and with the local community.”

Winston’s company, BalancedWork, helps organizations make data-informed decisions about when to meet in person or remotely using calendar data to analyze meetings. The tech then recommends which setup is best suited for the situation. 

He also noted that local innovation groups like incubators have become less about daily coworking and more about regular, intentional meetups.

“The day-to-day ‘we’re just sitting next to each other’ isn’t happening as much,” Winston said. “Something is different — maybe lost. Whether that matters varies case by case.”

Designing new norms, not chasing old ones

Though the founders praised the benefits of flexibility, including being able to hire specialized talent from across the country, they were candid about the downsides of distributed teams. But Stein from Common Paper is finding ways to remotely recreate experiences that often take place in person.  

“Junior folks learn by eavesdropping; remote loses that,” Stein said. To fill that gap, Common Paper has implemented recurring “scheduled unscheduled” Zoom calls — intentionally agenda-less spaces where employees can talk about anything from dogs to deal flows.

Magee said he regularly meets with his junior team members, often daily, for their first few months and starts every meeting with 5 to 10 minutes of personal small talk because it deepens relationships. 

“Once they see you invest in them on their terms,” he said, “they’ll work hard for you.”

Leadership behavior sets the tone, Winston noted, and actions matter more than words. “People sense how a leader feels,” he explained. 

Ultimately, each panelist stressed that remote and hybrid work can be effective — but only with intention.

“Remote work is a privilege, not a right,” Magee said. “It’s on both the employer and the employee to make it work.”

Asked whether they would recommend a remote job to a recent college graduate, the panelists agreed that in-person experience offers value early in a career. 

“Take an in‐person one,” Winston said. “We humans absorb more than screens can show.”