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Bot Conversion Strategies

Learnings from 3 months of conversions to premium

Hi there — we are the makers of the JIRA Slack bot that connects Slack to JIRA via an always listening bot implementation. This post shares some insights into what we have learned over the past 3 months since we offered a freemium model to our users. Hope this helps someone!

1. People will pay — if you make them happy!

Is this real? Can you make a bot that provides value and people will get out their credit cards and pay for it? Our experience says “yes”.

Getting people to pay is certainly not easy. They already pay for JIRA and likely for Slack + millions of other services. To make people convert the money spent has to be less than the value provided. If we could prove to teams that having us and paying a small amount saves money then we could claim we provided real value with our service. The question was if the bot area had developed enough that organizations would sign up for an additional service and do so via a 3rd party website. We have long believed (and still hope) that Slack should offer payments directly via the Slack app store but currently that’s not available — maybe coming soon??

Our journey to the premium bot started with a beta version which we offered for free. We used all the usual places to promote our beta solution and found early on that teams were definitely interested in the solution. Being that it used to be completely free, some of our customers were used to our service and had not been asked to pay for it so we knew that would be a potential challenge.

We decided to offer our new features with a 30-day trial with no credit card required. This made it easy for teams to try us out, see the value and hopefully decide to keep the premium features.

We found out early on that some teams did see the value and didn’t feel the need to wait the full 30 days to sign up for ongoing service. This felt like a good sign. Today we see an average of 26 days for teams that convert from trial to premium.

The chart below shows our subscription growth over time starting with the first teams on the new solution in February of 2017.

Subscription growth over time

As the chart above shows the MRR started within a few days and has been growing ever since. We have also seen an increase in sign-ups after a major competitor entered our space — more on that below.

2. Price it Right

When thinking about the value we provide we worked through a number of different pricing models and now we admit — we didn’t get it right the first time.

Our initial premium model was the following: $1 per user / per month

This model seemed clear and easy for us to use. It also provided a simple metric with the number of paid users exactly equal to monthly recurring revenue.

We found out pretty quickly from our beta customers that this was not viewed as fair. Here is a real email we received from one of our high usage & large customers.

“I love this add-on but your pricing is insane. $402/mo? No thanks! Would be willing to pay for this add-on but that cost is way too high and nowhere near what I would call value for money”

Oops, did we really think people were going to pay thousands of dollars a month for our service? Our model actually pushed larger teams away from us — not a good idea!

After a short meeting we decided to revise our model.

The updated model is $0.50 per user / per month and free for teams < 10 users.

The new pricing felt fair and set a low bar for large teams to join in and lucky for us they have decided to come onboard.

3. Offer Annual Plans

We originally launched with only a monthly option to keep things simple from our side. It was of course clear that annual + discount for annual is a common offering but we didn’t want to handle accounting complexities, refunds, proration, etc when just starting.

The first customers who asked about the lack of an annual plan brought up a good point. Users don’t want to create expense reports every month for a service. Many teams would prefer to just pay one time per year to lower the paperwork on their side. Not to mention the monthly invoice emails adding to already cluttered inboxes.

The chart below shows annual plan growth over the past few months. It started slow out of the gate but has picked up in the past month.

Annual Plan Growth

4. Don’t fear competition

Being the bot that connects JIRA to Slack we knew that eventually Atlassian JIRA could come out with their own solution.

One thing we could never understand was the lack of love from Slack in the app store. It had been strange how Slack had never featured our bot despite our growing popularity. We could tell from looking at all options in the “bot” category sorted by popularity that we were getting noticed by users but for some reason we couldn’t get the ear of Slack. We emailed, created support tickets, applied for funding (we didn’t want) and couldn’t get any real response.

Then on March 28th Slack and Atlassian posted an article together — An easier way to use JIRA with Slack

The announcement came with a decent amount of hype, a dedicated page from Atlassian and some focused marketing. It was clear both Slack and JIRA knew this was a needed solution and had been working for some time on this release.

At first we thought “O well, this one is over. Time to work on our next idea” our biggest potential competition had just entered the market. We anxiously awaited a churn cycle or signup slow down but it never came.

We later found out didn’t have as much to fear as we thought. The “official” version only supports JIRA Cloud instances and doesn’t provide the functionality we offer. It appears now that the additional marketing/awareness made lots of organizations realize that connecting Slack to JIRA is a good idea and those companies then started to look for better options and found us.

The chart below shows how larger competition increased our demand and usage.

5. Be user centric

From the start we knew that our business would be built on many teams each paying a small amount for the service. Each one of these teams needed to have a voice and we have to be listening. To us happy users = a strong business.

Here are some ideas:

  1. Create a Slack team for our users to interact with us and each other — Join Ours
  2. Survey your users and measure feedback with a metric like NPS
  3. Personally reply to every email, send messages just asking how its going and don’t send automated emails
  4. Keep users informed via twitter, bot based messages and more
  5. Listen to feedback and alter your solution based user input

One metric that won’t lie is usage. Therefore daily and monthly active users are being tracked closely.

Here are some charts for daily and monthly actives:

Monthly Active Users
Daily Active Users


After 3 months of a business build on Slack with a bot and freemium model we have learned a lot along the way and believe this can be a real business.

Moving forward Nextup will be increasing public relations and paid advertising to continue to ensure teams know about the best solution to connect Slack to JIRA. There is a possibility that Nextup will be extended to Microsoft teams or other chat solutions and certainly other ticketing / project management platforms could be a next step — it all depends on what the users want.

Please feel free to share comments below, find us on twitter or reach out at to share your feedback.

Thanks for reading!