"The tools just weren't built for this": Aaron Rawcliffe on building Whenn

You've been working in conferences and event strategy for fifteen years, across finance, tech, oil and gas, energy, engineering, and law. How has the coordination side of the job changed in that time?

It's got more complex without the tools getting any better. The number of external stakeholders involved in a typical event has increased — more speakers, more partners, more organisations in the mix — but the way you actually get a group of them onto a call is still fundamentally the same as it was fifteen years ago. You send an email, you wait, you follow up, you work out the overlap yourself, you send the invite. That process hasn't really changed. What's changed is the volume.

What specifically was the frustration that led you to build Whenn?

It was the realisation that the tools just weren't built for what I was actually doing. Most scheduling tools are designed for one person sharing availability with one other person — a booking link, a calendar embed, that kind of thing. That works fine if you're booking a 1:1 call with a client. It doesn't work when you're trying to get five speakers from five different companies onto a planning call before an event.

For external group meetings — meetings across organisations where you don't have visibility into anyone's calendar and you can't control when they respond — the only mechanism most tools offer is a polling grid. Everyone picks their available slots, you look at the results, you pick the time, you send the invite. It's better than nothing but you're still doing most of the work yourself. And you're still chasing the people who haven't filled it in.

The frustration wasn't one specific moment. It was the accumulation of doing the same manual process for years and gradually realising there was no reason it had to work that way.

Where did the initial idea come from?

The earliest version of the idea was quite abstract. I was thinking about what Stripe did for payments — they took something that was technically complex and operationally painful and made it a single integration that just worked. I wanted the same thing for external group meeting scheduling. One action from the organiser, everything else handled.

That framing turned out to be useful because it kept me focused on the right problem. The goal was never to make availability collection slightly more convenient. It was to remove the organiser from the process after the initial setup entirely.

Whenn is specifically for external group meetings — not internal scheduling or one-to-one booking tools. How did you arrive at that scope?

Partly by looking at what already existed and partly by being honest about the problem I actually had. Calendly solves one-to-one external booking. Google Calendar and Outlook handle internal meeting coordination reasonably well. The specific gap — multiple external participants, different organisations, different calendar systems, no shared visibility — didn't have a good solution.

It's also a harder problem. Internal meetings are easier because you have calendar access, organisational context, and some ability to just decide on a time. External group meetings across organisations require all the coordination work to happen upfront because you're working with people you can't instruct, only request. That's where the overhead lives.

You built this alongside a full-time job. What did that constraint force you to get right?

It forced me to be ruthless about scope. When you're building in evenings and weekends, you can't afford to build things you're not sure are needed. Every decision has to earn its place. I think that's made the product more focused than it might have been otherwise.

What did you think the hardest part of the problem would be, and what turned out to actually be hardest?

I thought the availability collection was the hard part — getting participants from different calendar systems to share their free/busy data without requiring them to create accounts or install anything. That turned out to be solvable.

The part I underestimated was the confirmation step. Finding the overlap in everyone's availability is straightforward once you have the data. What's not straightforward is taking that result and automatically confirming the meeting — picking the right slot, accounting for timezones across all participants, generating the video link, writing the confirmation, creating the calendar event, and sending invites that actually land in people's calendars. That whole sequence is what AutoWhenn does, and it took considerably longer to get right than I expected.

I think most scheduling tools stop at "here's your overlap" because the confirmation step is where the complexity lives. It's also where most of the value is.

There was also a layer of compliance and verification work I hadn't fully anticipated. Getting Whenn approved as an OAuth application by both Google and Microsoft — so that participants can connect their calendars through a verified, trusted integration — is a genuinely involved process. The same with Zoom. And building anything that handles calendar data and personal information in the UK means being ICO registered and GDPR compliant throughout. That's the right way to build it. But it adds significant time and process to a project you're running alongside everything else.

What do you know about the problem now that you didn't know when you started?

That the coordination overhead is invisible to most people until you look for it. It doesn't show up on a timesheet. It doesn't have a line in a project plan. It happens in fragments — a quick email here, a follow-up there, five minutes of timezone arithmetic — and it never accumulates into something that feels like a problem worth fixing. But when you total it up across an event cycle, the number is significant. A week of a senior producer's working year, roughly, spent on logistics that produce no content, no relationship, and no programme.

The other thing I know now is that I wasn't alone in feeling this frustration. I assumed it was a specific problem in my corner of the events world. It turns out it's felt much more broadly — anyone who regularly coordinates external meetings across organisations, whether that's a recruiter running panel interviews, a consultant bringing multiple client teams together, or a lawyer coordinating multi-party calls, runs into the same wall. The tools just weren't built for group meetings where the organiser has no visibility into anyone else's calendar.

What would you want someone to know about Whenn before they try it?

That it's built for the specific situation most existing scheduling tools weren't. Not 1:1 booking, not internal team scheduling — external group meetings where you're working with people from different organisations, different calendar systems, and different levels of motivation to respond to your availability request. That's the problem it solves, and that's the problem I built it to solve. I think that's still the most honest thing I can say about it.

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Whenn handles the entire coordination process — automatically.

Add participants by email, they connect their calendar, AutoWhenn finds the best slot and sends everyone an invite.