Lola

I cofounded Lola in 2015 with Bill O'Donnell and Paul Schwenk, guys I've worked with for decades.

The original vision for Lola was to be a mobile app to allow travelers to message a concierge 24x7 to make travel plans on their behalf.

We learned during our first year that to our surprise, 80% of our users were business travelers. This led to our first pivot, where we started to focus on business travelers exclusively.

We interviewed dozens of business travelers to learn what was different about business vs. leisure, noting that a few of us built Kayak so we already knew consumer travel. We learned many things in these interviews, for example, business users choose flights based on (a) their favorite airlines (b) the schedule, and lastly (c) the price. This led to a design which looked a bit different than consumer sites and apps.

Krista Pappas and I developed a five year exclusive partnership with American Express Global Business Travel (GBT) to provide travel service to their small and mid-size customers. This was an important partnership for us, not just from a validation and revenue standpoint, but also from a learning standpoint, as GBT is the #1 best solution for larger company travel.

In 2018, we hired Mike Volpe to join as CEO, and then I became CTO. This was a fanastic move for Lola, as Mike is a much stronger executive leader than me, and it allowed me to focus on the things I like the most -- people ops (with Stacey Scott), product strategy (with a team of product managers) and design (with Lincoln Jackson and other designers). Dennis Doughty led architecture, and Chris Stasonis led growing and managing the engineering teams and processes.

Over time, Lola started paying attention to other roles in business travel - the executive assistant, and the finance leader.

We learned that power business travelers already have formed "shorthands" with their executive assistants which made booking travel as simple as sending a text message or email, and then trusting that the assistant already knew all your preferences and your calendar, and that s/he would just book the right thing for you. Based on this learning, we built a "book on behalf" feature that let any Lola user book travel for any of their colleagues, without having to enter all of that person's info each time.

For finance leaders, Lola focused on travel policies and financial reporting, given that travel and entertainment is often the biggest discretionary expense a company has.

2019 was a fantastic year for Lola -- we figured out product market fit, and we were growing rapidly.

When the Covid-19 pandemic hit, business travel stopped, and our revenue went to zero. In March 2020, we began an aggressive pivot from SMB travel management to SMB travel and spend management. Instead of going to CFOs and saying they should buy Lola to reduce the cost and complexity of travel planning, we then went to CFOs and said we could reduce the cost and complexities of all employee spend.

Lola developed its own corporate Visa card with real-time authorizations tied to actual budgets. This allowed finance and other executives to always have a real-time view of budgets, and forced spend to always stay within budget. Our software allowed users to set up budgets and sub-budgets with delegation for budget ownership. We also built a simple-to-use invoice / accounts payable solution.

In October 2021, Lola was sold to Capital One. This has been a fantastic next step on our journey, and the Lola team is now focused on spend and payment innovation for millions of businesses, where we will be bringing new products to market based on Lola tech and Capital One tech.

I am proud of what we designed and built at Lola, but more importantly than that, I'm proud of us developing a strong team of people who worked exceptionally well together, and who took care of each other in every sense of the word.

Lola was also lucky to have a gifted board, but the one person I want to call out explicitly is our Chair, Gail Goodman. She has been an incredible guide for me over the years. And finally, I could not have done Lola without Eliza Bladon, and I'm grateful to all other Lola employees -- past and present -- for building this company together.

paulenglish.com 13-Oct-2021