I'm Bridget Harris, Co-founder of YouCanBook.me - Bootstrapping SaaS with a remote team. AMA!

Hi Krish - thanks for those questions, I really enjoyed my chat with Jane - often the ‘philosophy of free’ gets somewhat over looked as an obvious thing but as you say, there is a lot to under pin it.

Much more to say on this but I’ll give you an overview of where we are with these particular issues:

1. Customer feedback loops and product ownership

As I said in my interview with Jane, it looks us a while to realise we were actually giving ourselves a double whammy of problems giving too much away on the free tool, and at the same time having to support those features because actually they were really complicated to use and set up! We could see that people who regularly sign up free tools (of which I am one) aren’t necessarily interested in getting involved in support or the community - more they just want something to ‘work’.

So conversations with these uses wasn’t necessarily the most productive, which was one reason why we reduced access to support at the same time making the tool much more simple to use. But there are also different to people who are genuinely trialling the tool.

Separating out our signups based on these kind of intentions has been invaluable for us to target conversations with the right people - generally it’s much larger teams who are interested in our product roadmap and want to have active feedback on it. Others just want to know if we are getting a fix out for some niggling UI. Equally, we do conduct UX research across a broad range of users who we’ve invited to speak to us specifically who do not have any immediate concerns.

Having said that, we do have lots of ways to interact with everyone who uses YCBM - we have a community forum, we will set up question / survey tools which pop up after events that are particularly interesting to our UX researcher, and we will be in touch via email when appropriate. Anyone can email it, it’s just if they are on the free plan we don’t give them access to our support in our chat beacon.

The update on this is we’ve now switched to 100% free trial - so everyone has access to our support for 2 weeks, and can then track our conversations / conversions within these cohorts before they drop into the free plan.

We have a very tight feedback loop between Customer-Product-Engineering and then back again for fixes and bugs. The ownership of the product is very much led by our Head of Product - but we are small enough to make sure customers and what they tell us are at the heart of our roadmap.
To that end, out head of Customer Success runs a ‘customer spotlight’ session each month, where each member of her team contribute to a 1 hour summary of what is happening in the works of our customers that everyone in the company has to watch.

2.traditional freemium funnel

No we don’t forgoe it - we have actually just overhauled our design UI to include lots of upgrade prompts, as well as more prominent branding on YCBM pages if you are using the free version - we do over 1 million bookings a month, so it’s very important to us that all those bookings carry our branding and help promote our tool.

Here is our feature page where you can toggle between free / paid and we add prompts for popular things to do on the paid plan. But at the same time, our target market are teams and larger groups who need scheduling - who would have to pay as that involved multiple calendars (we charge per calendar links). Consequently, we don’t need to do a massive ‘Big Sell’ to the free users, as they already help us by managing their bookings on our platform,

Metrics that matter to us is activation - how soon as someone taken a booking, and activity - how many bookings does someone take. This tells us how likely it is they are going to be to carry on using our tool and also whether they are likely to want to upgrade (someone taking 1 booking a month isn’t going to feel like paying $10 for that) which makes sense.

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