How to figure out why free users don't convert?

Depending on the type of product, maybe a discord/slack community?

Aside from that, unless I'm super invested in a product, the feedback mechanism needs to be ultra low friction.

This example is probably outdated now, but I remember I used to use Visual Studio's smiley/frowny feedback that was (IIRC) in the title bar: click the frown, type my complaint, click submit.

Sometimes multiple choice works too, BUT: the button should be something like "Submit Feedback Now" not "Next"! If it's a "Next" I assume that means 10-100 more questions, including and my SSN and home address.

^^ just some rando's opinions. Take em or leave em.

It has to provide value above the perceived cost. Many times, I sign up for a service to solve a specific problem. Once that problem is solved, I don’t need yet another subscription every month ticking away at the bank account like a flea. So I cancel. If I need it again, I re-subscribe. Half the time, when I can’t even try something to see if it will work if I pay for it, I just leave the page in search of another solution. Especially smartphone apps that have a landing page and immediate sign up without a trial. No thanks, the dark pattern is strong and I’m out. App deleted, never go back. First impression is everything. Give me enough to know if it will work, and I’ll pay. But I won’t pay beyond its usefulness. I have a very selective amount of things on recurring monthly charges. Things with high value like offsite backup. Or music. Or streaming. But even streaming I cancel and re subscribe every few months and try another one. Bottom line is don’t expect once a customer, forever a customer. Lifetime subscriptions for high but working reach price are interesting. Flighty for me was that. Drop a couple hundred and never deal with subscription again. Over one hour of saved time it pays for itself.

> many more features than competing apps

In a lot of cases polish and quality matter more than the feature count. If it works, but looks half-baked then you will see no coversion, no adoption and next to zero feedback. Unimpressed users just leave.

One thing that surprised me at our company is how many people actually respond to automated lifecycle emails - especially if they seem like they are coming directly from you.

if a user spends an hour in the app or hits some other minor usability metric you can send them something like (obviously you can customize it / expand on it as needed)

Hey John,

This is Thorum the CEO - I've noticed you've been using the app for some time now. Do you have any questions or anything I can do to help you understand the product better? I'd be happy to hop on a zoom call - here is a link to my availability if you have a time in mind

if you can get them on a call or screenshare that is the best possible outcome - there is nothing better than directly talking to your customers about their problems or why your app is not seeming to solve them

Do you have analytics in place? You can self-host PostHog or use them as a service to see what's going on and follow the drop-off. How fast are you getting them to successful usage? There's inertia.

What problem does your product solve? Is it an on-going problem or something that's solved once?

Who has that problem often and to whom does it matter? A meme generator only is useful to me when I want to insert some wit into a conversation but if it were my job to produce memes, it would be a tool of the trade.

Who's buying and why? Who's not buying and why? How many conversations have you had with those who didn't convert? Ask them to hop on a call and ask them about what brought them to the product in the first place, what were they trying to accomplish, and what was their experience. Get some feedback in open conversations.

Pick a set of random users and personally email 10 of them every day for a week, asking them why they choose not to continue.

This is one case of the do something that does not scale, don't automate this.

Have you tried talking to them?

You also have an option to see your website click heatmaps or recordings of user behaviour (Hotjar does a reasonably privacy-respecting effort there), which simply tracks what your users are doing with no extra effort for them.

what does usage during the trial look like? do you track retention? what are the touchpoints during the trial (email, etc.)? do they understand the value prop by the end of the trial?

of all the things people could do during a trial, what usage patterns correlate to trial conversions? using xyz features? completing xyz activities? how do you onboard them after they make an account?

if all that is yes then maybe it's a price issue -- (either too high, or they didn't understand the value enough to think it was worth)

Are you placing the feedback right after key interactions, or is it just a random link in the footer or something like intercom that could get blocked by ad-blockers?

Are you proactively showing users the value your service provides, or just relying on “discoverability” that might never happen?

read about pricing strategies by other founders and startups, maybe your free tier is too generous there isnt much need for them to convert in the first place.

might even get rid of the free tier and really start being cut throat about it.

keep sending emails and see test features users are interested in via clicks or registrations.