Introducing TimeKeeper V2.0

Chronicling the journey of TimeKeeper's initial design decisions as we launch V2.0....
Sean QuinnPosted on Friday, October 20th 2023

Back in January 2018, the first code was written on what is now TimeKeeper.

Before we introduce TimeKeeper V2.0, I think it is interesting to have a retrospective on how the initial version of TimeKeeper came to be and the context that shaped V1.0.

During those early days of building a product, the goal was to test if the seedling of an idea is in fact feasible, this is known as the "validation phase".

There are essentially two paths for most startups at this point:

Two Paths, Bootstrapping or Raising Capital

Path One: Raise Capital

The most common path at the time was to spend a few months seeking external investment from angel investors, venture capital firms or friends and family. This is so you have capital for 'Go to Market', that is so you can invest in resources such as design, engineering and sales.

During this time you typically spend more time working on a pitch deck than the product and will ultimately result, if successful, in exchanging a minority stake of equity in the business for the investment. The major upside being that this temporary period can in fact accelerate your business several years by having capital to deploy.

Path Two: Bootstrapping

The path less trodden then, although more popular now (also the common route taken by small non-technology businesses) is to 'bootstrap' the business with your own funds until reaching a point where there is enough capital coming in to reach break-even or 'default alive' - the expenses of the business match its income.

The upside is that you retain 100% control of the business, however the downside being that you can't invest properly in areas of the business until further down the line, which means growth is usually much slower.

TimeKeeper's Path

I decided to go down the bootstrapping path (I'll leave the specifics for another post) as this would be a quicker feedback cycle on whether the product solved a pain for customers. At the time, TimeKeeper had received a £15,000 grant from Ignite/Invest NI Pre-Accelerator - the only cash injection into the business - and it was critical.

This grant was stretched to cover 12 months of personal and business expenses, so we could get TimeKeeper V1.0 (TimeKeepr back then) out the door and a handful of customers bringing in some revenue as well. More on that origin story here.

Why am I bringing this up? Given the business went down the bootstrapping path, the business didn't have resources to invest in design at that time. Investing in design at that time would have cut the initial business runway in half. Instead I decided to rely on my barely existent design skills along with early customer direction to shape the first version of the product.

V1.0 Design

I always appreciated good user experience and was aware of what I did and didn't like in certain products.

That didn't translate to me being able to craft a user experience that I or our customers loved, though. In fact, I would say TimeKeeper V1.0 had a very simple, functional, yet brutalist look.

Early version of the TimeKeeper Application on the left

The professional design was put on the back burner and left as a task that we would get around to when we had time and capital.

Revisiting Design 5 Years Later

At the start of 2023, it was decided that this would be the year to get our redesign done. Why in 2023? Well, we left it too long for a start. We made tweaks to the design along the way making it slightly better, but a rebuild from the ground up had to be done in a consistent, coherent manner.

No way did I think we would still be using the base of our original design in 2023 but that's startups for you. They are chaotic and there are a million things that get done and fall by the wayside.

Secondly, our hypothesis is that our design was hurting our conversion rate of trials to paying customers. User experience is hard to quantify as it is quite subjective, however conversion metrics is a useful indicator to track impact of the new design.

New Design

One of the goals of the redesign was to 'freshen up' the application. That meant a change in our colour scheme, moving away from our traditional dark background to a fresher off-white colour scheme. This small change gives the application a completely different feel when using. I'm sure there are some colour theory experts that could explain why this is, but for me, the new application just feels lighter.

Our typography has transitioned from Gilroy to TT Interfaces. While Gilroy was effective, we opted for a change to provide the application with a fresh feel.

Here's a quick peek of some of the changes between V1.0 and V2.0 below:

Introducing TimeKeeper V2.0

Challenges of the Redesign

There were a also number of challenges in re-designing a live application with customers who rely on it.

TimeKeeper has a range of users of differing ages with varying technical skills. Ultimately the product is a utility, where people want to clock in, book time off or check their timesheet. This meant drastic changes to how certain screens looked and behaved was off-limits. Mainly to prevent 'shock factor' but also to allow users to be able to perform their everyday functions without significant re-training. The goal is for the application to feel familiar but slicker.

Another challenge was that TimeKeeper has evolved massively over the last 5 years. Our original design didn't cater for a growing feature base, resulting in long screens of content with no real rhyme or structure. Our design partner gave us a number of options here to break content more naturally.

V2.0 has a fresher look with an off-white background


The initial design process took 5 weeks (Q1 2023) and the rebuild of the application took around 12 weeks from start to finish (Q2 - Q3 2023). The new experience is cleaner, more professional and open to extension as we build more and more features on the platform.

Expectations on Launch

So what do we expect on launch? I personally expect a degree of hesitancy at first. People are naturally resistant to change but I'm certain the new design will be a hit with our customer base, and will help elevate the experience for everyone.

Revisiting that Initial Decision

I've been asking myself the question: If I was to do it again, should I have raised capital to prioritise a professional design from the start?

Given our situation at the time, I still think I made the right call. The capital would have resulted in a better looking experience for our early customers however there were just too many unknowns. Would the product work? Did customers care to pay for it? Will we pivot the product in another direction? Can we afford to lose half our runway?

I didn't know at that point what the platform needed to be, likely resulting in a lot of design work that would eventually be scrapped.

I also feel that users are typically in the application simply to complete a function and exit. They don't sit in the application all day, so compromises could be made on the initial design as the contact time is limited.

Looking Forward

We've definitely lost customers along the way due to our V1.0 look and I feel we could have prioritised this work sooner, especially building out a design component library.

The team is delighted to release our new look and personally I'm very proud of where the platform is today. There's more work to do but we'll do it as we always have, in time.

If you are TimeKeeper user, the updated version is now available on the Apple App Store and Google Play Store. Please do check it out and if you love it, or hate it, we'd love to get your feedback here.

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