The year is 2010 and Dave Gilboa is hard at work designing Warby Parker’s very first homepage — in PowerPoint. He’s sitting among stacks of inventory in his co-founder Neil Blumenthal’s tiny apartment (the same apartment that would double as the company’s first showroom). That’s the moment Mara Castro walks through the door, starting as Warby’s first official employee just hours after receiving her offer. She jumps in with little more training than, “Ask us if you have any questions.” Just as suddenly, employee experience becomes a top priority.

Eight years later, Gilboa and Blumenthal have learned a lot about what makes a startup successful. Their website is managed by a team of professionals, and the apartment living room’s been replaced by two offices (one in New York City and one in Nashville), an optical lab, and more than 60 retail locations across the US and Canada. One thing remains the same, though: their conviction that creating an extraordinary employee life cycle is just as important as developing a killer product.

“One thing I’ve always found surprising and unfortunate is that as companies get bigger and have more money and more ability to invest in the employee experience, they actually become worse places to work,” says Gilboa. “That terrifies us.”

At First Round’s recent New York Founder Summit, Gilboa dove into five areas where startups need to double down to make sure scale doesn’t ruin all of the things that make them great places to work — to make sure they continue to feel small, compelling, close-knit and rewarding. Read on for the tactics that have made Warby Parker one of the most sought after employers in the world.


Many of the most memorable moments in any employee’s life cycle happen at the very beginning. Everything is new. Everything makes an impact. They either feel supported and excited or lost and bewildered. They feel initiated or left out. In a way, this sets the tone for how they perceive your culture and the rest of their time at the company. “You have to make people feel special and welcome from the very first moment they interact with your organization,” says Gilboa.

Don’t just sweat the details — be original. Warby Parker’s welcome packet includes standard-issue fare like an office map and style guide, but also something unexpected: A copy of Jack Kerouac’s Dharma Bums. “The name Warby Parker came from two early Kerouac characters,” Gilboa says. “We want to make that heritage part of the employee experience from day one. It’s something utterly unique to us that will always stand out.”

Make new employees the most approachable people in the office. Being new can suck. You feel like you have to prove your value right away. Everyone around you has some degree of shared history, inside jokes, and institutional knowledge. To help your new employees break the ice, you want to take pressure off their shoulders and make it easy for your existing team to induct them into the culture and conversation.

Warby Parker does this in a few ways. The first is a quirky variation of something often done at large companies, but seldom at their smaller counterparts. They designed a custom helium balloon that features an illustration of a steak with a pair of glasses on. It says: “Nice to meat you!” These balloons are affixed to every newcomer’s desk for their first couple weeks. Other employees are conditioned to treat the balloons as beacons so they’ll introduce themselves and strike up conversations with newbies.

For similar reasons, new employees are asked to introduce themselves during all hands meetings, so that they can seed commonalities and inside jokes in front of the rest of the company. As part of this intro, they’re asked to share ‘a fun fact’ about themselves. “They’ve ranged from someone who held Michael Jackson’s baby to a 5’ tall woman who announced she had the colon of a 6’ tall man,” says Gilboa.

By asking folks to share something memorable (and occasionally bizarre), you can help them become more recognizable to their colleagues and equip everyone with a hook to get to know each other better and strike up conversation around the office. People don’t do this for themselves as proactively as you think they will. You need to build it into their first days on the job to make them as approachable as they’d like to be — without putting the onus on them to forge a bunch of connections on their own.

Make training an executive priority. Way too many companies delegate new employee onboarding and training to junior staff or the human resources team. Some even outsource it. But Gilboa says that good leaders don’t even dream of relinquishing this crucial task. “We think it’s vital for the most senior people at the company to be involved in this process, including me and my co-founder,” he says.

The presentations might seem repetitive after a while, or below the C-suite’s pay grade, but having them drive onboarding sends a strong message that new employees are extremely valuable to the company. Beyond that, a startup’s leadership team tends to have all the important institutional knowledge at their fingertips — from the origin story to governance structure. Also, when company values are articulated, explained in detail and reinforced (ideally with examples) by a founder, they carry far more weight than they might when simply written on a piece of paper or a poster on the wall.


Meet weekly. Warby Parker still has weekly all hands meetings. A lot of companies assume that cadence only works for very small startups, but that’s not the case in Gilboa’s experience. It’s kept all employees at Warby feeling connected, informed and engaged for years. They aren’t planning to ditch it anytime soon, and recommend it as a tool for all companies.

“It’s ironic that as companies get bigger they tend to communicate across their organizations less frequently rather than more,” he says. “That’s headed in the wrong direction to me, and we’ve seen how valuable it is to do the opposite.”

Warby’s standing meeting is every Wednesday at 8:30 a.m. EST, and it’s a can’t-miss affair. Led by both Gilboa and Blumenthal, it features appearances by department leaders from across the org. “We talk about new developments, themes we want top of mind for the team, company-wide priorities, strategic milestones, etc.” The proceedings are also recorded and posted so that those who can’t be there can watch after the fact.

Find ways to say the same thing many different ways. As the company launches new stores and labs, employees are constantly moving around and might not be able to watch a full all hands. So the founders invented a new communication vehicle to get them the information they need while on the go: The Weekly Briefing.

“Neil or I record something roughly three to five minutes long — basically a highlight reel of what was shared during the all hands meeting, but just the need-to-know content,” says Gilboa. “It’s a way for us to convey the key messages to everyone in the company on a weekly basis — it’s really easy and quick to consume — and it really does serve to make us feel like a smaller, tightly-knit community.”

His advice for founders: Think through your employees’ schedules. Who might be missing out on key communication touchpoints and why? Are they constantly traveling? Do they not have a lot of time? Are they working remotely? Create new communications products that fit their particular habits and needs. Get them the information they need how they need it.

And get it to them through multiple channels. In addition to weekly all hands meetings and The Weekly Briefing, the leadership also circulates Warby Weekly, an internal email newsletter featuring a calendar of events, news about launches, details of new features, and more — yet another opportunity to repeat themselves and make sure employees are internalizing where the company is headed and how.

Make this a two way street by giving employees ample opportunity to celebrate company-wide milestones. You want to create as many common experiences for people as you can to keep them feeling cohesive even as your headcount expands into the hundreds. “When we turned five, we threw ourselves a half-decade parade,” says Gilboa. “We found the shortest street in New York and even hired a marching band. The whole team was involved, and it was a ton of fun.” When they reached 1,000 employees, Warby Parker unfurled a banner in its headquarters that included every employee’s name, in the order they were hired.