Founders of WeWorked — John Holmes II and Will Roberts III

Timesheet software for small businesses

John Holmes II
Dec 10, 2017 · 3 min read

WeWorked is easy-to-use timesheet software the integrates invoicing, leave tracking, expense tracking and more. WeWorked is designed specifically for small businesses in any part of the world. Most business software is designed for large enterprise customers, which results in high prices, unwanted features, slow enhancement rate, and terrible customer service for small businesses. WeWorked focuses on the time tracking needs for small businesses by integrating leave tracking, invoices, expense tracking and reports into an online application at an affordable price point.

Our team of five is mostly in the DC Metro area. However, we like to travel and can work anywhere so we like to say our team is pretty global. You can find one of us working in DC, Miami, San Francisco, and even Dubai.

What moment or experience inspired you to start your own company?

Will and I started WeWorked after working for several small businesses that struggled with tracking staff time. Most of the small businesses simply could not afford the timesheet offerings available, or the software was so bloated it required weeks of training and expensive customization to get started. We set out to fill the void.

Quick Meeting in Will’s Office

What was the greatest challenge you faced when starting out and how did you overcome it?

A big challenge was getting past the first few releases. You work so hard on a product that it becomes your baby. You think you have built the greatest thing in the world and have thought of all the necessary features, only to hear from a customer that they wanted something slightly different. You have to realize that you are building software for a target audience and you need to have thick skin to handle all types of feedback. Listen to the feedback and make adjustments accordingly. The sooner you realize the feedback is not personal, the better your product will become.

With a small team, we also had to learn to optimize the limited developer time we had. That’s where Stripe came in. Stripe made it possible for us to streamline our entire payment and subscription processes. We started out with PayPal, which left a lot of manual processes. Our business model is hinged on efficiency and minimal manual involvement. We had to manually adjust subscriptions when customers changed their subscriptions or wanted refunds. It was tedious and sucked up a lot of valuable time. Stripe allowed us to automate nearly everything we were doing manually. We no longer had to draft and send emails related to account changes. Now everything is automatic. When charges fail, customers are automatically notified. Charges that were failing before because of an expired card now go through thanks to Stripe algorithm and awareness. Time is money. The less time we spend on administrative tasks, the more effort we can put back into enhancing WeWorked. We also noticed that our upgrades have increased 25% since switching to Stripe. Stripe is just what we needed.

What does “success” look like for your company five years from now?

In the future we see WeWorked expanding into additional back-office services. Nearly everything in a business is tied to time tracking in some way. We want to focus on the most beneficial and heavily used integrations that would make our customers more successful. Success for us looks like constant growth, a larger international presence, and no outside funding. We pride ourselves on being bootstrapped and profitable.

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Built on Stripe

Hundreds of thousands of founders around the world have used Stripe to start and grow their businesses. We've collected some of their stories.

John Holmes II

Written by

Founder of WeWorked. Yes, bootstrapped and profitable. I love to create things. Don’t listen — They all just scared! @johnholmesii

Built on Stripe

Hundreds of thousands of founders around the world have used Stripe to start and grow their businesses. We've collected some of their stories.

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