When Paul English’s Lola launched, it aimed to bring the traditional travel agent into the mobile-only space with a compelling personalized chat experience for travelers. English’s pre-launch vision called for 100 agents, empowered by Lola’s proprietary tools that would allow them to use global distribution systems like they were cyborgs.

“We’re trying to create superhuman travel consultants who are AI-powered and can handle more trips per hour than a regular travel agent can,” English told Skift in May 2016 when the Lola app launched with the company employing only 15 agents. “They can make dramatically better recommendations than normal travel agents.”

A partnership with luxury travel agency Virtuoso followed along with the acquisition of metasearch technology from Room 77.

A year after launch, though, Lola pivoted to business travel and abandoned leisure travel altogether with fresh branding. It seemed to English that frequent business travelers would have more of a need for Lola than infrequent leisure travelers, and it turned out the service resonated the most with business travelers during focus groups.

This week, however, nearly a year after announcing its focus on business travel, Lola named a new CEO to take over for English. Mike Volpe, one of the early employees and former chief marketing officer at tech giant Hubspot, became CEO with English moving into a president and chief technology officer role. A few days later, they announced a new set of capabilities appealing to executive assistants and administrators at small companies, pushing deeper into travel management for small teams, a direction very far from Lola’s original play as a leisure travel booking service.

This looks like yet another pivot from a company that identified a problem in that travel ecosystem that it was unable to fix. Maybe there was never really a problem to fix at all. Or perhaps travelers weren’t ready to trust an app to personalize a trip for them, and a connection with agents through chat didn’t move the needle either.

Lola’s saga is yet another example of a well-funded and well-connected travel booking startup that has failed to catch on with travelers. Its back-of-the-house technology solution for agents, as well, has not been embraced by the agency community.

Despite raising $44.7 million, and having the brains of Kayak co-founder Paul English at the helm, the company faces a hard road forward as other well-capitalized startups have worked over the last few years to attract large, growing customer bases that drive revenue in the corporate travel sector whether by fees or commissions. These competitors include TripActions, TravelBank, and Travelperk

The next step for Lola is a more comprehensive play to develop a solution for tracking travelers, managing costs, and dealing with expenses. Lola on Thursday announced the launch of a desktop version of its app, along with more robust group management and payment tools. Despite English’s numerous claims that mobile-first is the future of travel, managing travel happens to be much easier on an actual computer.

“[We now have tools for] everything from expense quoting to guidelines, budgets, all that kind of stuff,” said English. “It’s all the ugly management that’s done manually in really small companies, but once we have 20 or 50 people or more, you need a system for it… we’re building a very lightweight version of Concur.”

Finding Customers

Acquiring new customers is where Volpe comes in, with his e-commerce bona fides and deep connections to the Boston tech community. He was fired from Hubspot in 2015 in the wake of Dan Lyons’ book on the company’s toxic workplace culture, and most recently served as chief marketing officer of Cybereason, a cybersecurity company.

Volpe signed on with Lola after a conversation with English, who was looking for a new chief operating officer to join the company. English said he quickly realized that Volpe would function better as a CEO overseeing the whole company, even though he himself was CEO, and brought it to the Lola board for approval.

Lola’s original chief marketing officer, Robert Birge, who held the role at Kayak for six years, left Lola in mid-2017. The role was not filled after his departure.

“The immediate plan is we have about seven or eight people [dedicated] to marketing, and we’re going to immediately double that,” said Volpe. “And then from there, I think we need to see what the pace of growth will look like. I would expect that next year would be a year where we’re going to make some very heavy investments.”

He’s also an experienced venture capitalist, if Lola wants to raise a Series C funding round. His connections could also help in finding a buyer for the company, although English’s deep travel sector connections would help as well.

English will focus more on building out technology tools for travelers, the impulse that initially led him to start Lola. He’s satisfied with the Lola user experience, even if they are entering a new sector.

“We do look at competitors a little bit, although I’m guilty of not looking at that too much because when I’m doing design, I don’t want to be influenced by others’ thinking,” said English. “I want to try to innovate, like we did at Kayak. So I don’t really look at competitors sites too much but we sometimes talk to our customers about competitors and about other products that they’re using. And when we design each new version of Lola it’s really important that it meets the problem the way the customer articulates it, and that it’s really simple and easy to understand.”

Photo Credit: Lola CEO Mike Volpe, left, with Lola co-founder and now CTO Paul English. Lola is diving deeper into travel management, a far cry from its original goal of becoming a leisure travel booking innovator. Lola