In his pre-HBS life, Ross Lerner (MBA 2020) worked alongside Paul Holder at a software company that served some of the largest owners of commercial real estate in the world. While many of these companies were using old-school spreadsheets to manage their assets, tenants, and leasing, the software solutions that Lerner and Holder supported offered the promise of a cutting-edge solution. The implementation process once a customer signed on, however, could be a struggle, with months of back and forth that slowed momentum to a halt. “To me it was crazy,” Lerner says, noting that a successful onboarding experience could translate to long-term results. “This is the time to put your best foot forward, but we were using primitive tools that didn’t allow any of that and caused our customers to become less engaged,” he recalls.

Seeing that the issue was widespread, Lerner and Holder founded OnRamp to help SaaS companies guide their customers through the implementation journey. Lerner refined the concept at HBS (and was a runner-up in the New Venture Competition) and has been working on it full-time ever since. Today, OnRamp offers a two-sided platform: Implementation teams have a consolidated view of the process to make sure everything stays on track, while the end customer gets a simple, personalized experience that guides them through the process so they can get up and running quickly. OnRamp already has customers in every vertical from health care to fintech, edtech, marketing, security, and automotive, and Lerner sees plenty of room to grow. “It’s really the entire B2B market,” he observes.

Lerner and Holder were already working from Boston and Denver, respectively, when the pandemic started, so nothing changed for them when the world went remote. They’ve since hired six employees who are clustered in Boston but working remotely. As the team expands, the founders wonder whether they should build a remote-first company or plan for an in-person structure—whether that means having a consolidated, Boston-based team or perhaps establishing hybrid clusters in a few hub cities.

Beyond the cost-savings of not paying rent, a remote-first approach would allow OnRamp to hire the best talent, wherever they live. That’s significant in a sector where the quality of your software engineers and other top talent can make or break it all. “Plus, in a world where people want to work from home and other companies offer that option, it’s difficult for us to ignore the market and what people want,” Lerner says. On the other hand, the founders have a shared appreciation for the personal relationships and team culture that’s best cultivated in person, as well as the kind of collaboration that’s unlocked when people gather around a whiteboard with their best ideas. Even so, there are continued uncertainties around the pandemic and what the future of the workplace might look like—or when we’ll get there.

Should OnRamp hire locally with the expectation of being able to reap the benefits of an in-person experience at some unknown point in the future? Or should the founders commit to hiring the best people, regardless of their geography, and embrace an all-remote approach?

I worked for Diamond Technology Partners, possibly the OG of remote-first companies, in the 1990s. We came together frequently as a whole company, which allowed for fun interactions and an amazing culture.

As a first step, a detailed, confidential survey of the existing team can help clarify which roles are better served with office space, if any, and how often people would like to be there. If some people want to be remote and others somewhat in-person, consider hiring from concentrated locations, starting with Denver and Boston. By limiting the number of locations, the founders can invest in the best work environment for each person. With junior employees, it’s helpful to build camaraderie by having substantial in-person interaction, and location concentration allows for this. With several locations distributed geographically, OnRamp will be able to find a diverse, more-than-sufficient talent pool.
—Shereen Shermak, HBS Rock Center Entrepreneur-in Residence and CEO of cryptography company Nth Party

Remote-first labor is the greatest boon to software startups since Amazon Web Services. No role in a SaaS startup, from engineering to inside sales, requires physical location. Thus you have the good fortune to go remote-first while startups in hardware or the life sciences cannot. Embrace the opening for increased quantity and quality of candidates.

Your initial cluster of employees should be viewed as an opportunity, not a constraint. Over time, even if remote-first, your employee base will form clusters due to population densities. Enable them to congregate with part-time access to coworking offices. They will self-organize according to project necessity or their own desires for face time.

Remote-first will not be without challenges. Management by walking around is much harder, for example. But if the two greatest challenges of an entrepreneur are finding a massive pain point and hiring enough exceptional talent, remote-first is worth the price as your greatest weapon to address the latter.
—Samuel Clemens (MBA 2004), HBS Rock Center Executive Fellow; founder and CEO, Reprise; venture partner, Accomplice

At Ovia Health, we made the shift to remote work before the pandemic. We invested in communication software and hardware, company-wide remote training, remote-friendly company policies (i.e., video, phone, email, Slack), and regular, in-person company retreats. We also maintain a flexible workplace at our headquarters in Boston, where people can visit or have small team retreats. Our remote culture has allowed us huge flexibility in hiring and logistics. I did not expect that the investments we made for remote work would also make us a stronger company. In an in-person company, it’s easy to hide communication issues that become very obvious when you’re working remotely. I would recommend building for remote work; even if you end up in the office in the future, the investments will pay off.
—Paris Wallace (MBA 2007), HBS Rock Center Entrepreneur-in-Residence and founder and former CEO of Ovia Health

Got a case? To take part in a future “Case Study,” send an outline of your company’s challenge to bulletin@hbs.edu

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