We started as a job matching platform for employers but revenue model was weak and built a scheduling system which will increase employer stickiness - hence we can charge a monthly subscription fee. A small portion of the employers will need scheduling but may not see the value of our platform yet or that they already have an existing older system. Our system basically allows employers to schedule workers shifts and shifts are turned into job post so that employers can easily manage and hire their hourly workers. Now that we need to convert the users, we are afraid that after the 7 day trial, employers will decide to quit. We will then not have enough job posts and will face the risk of loosing jobseekers. An argument to this is that if employers who post jobs are only free riders and not going to use scheduling/ pay for our monthly subscription fee anyways. It is better to grow with only our product lovers and ditch other employer.
"...may not see the value of our platform yet or that they already have an existing older system."
This is where you want to focus your energies.
Why don't they see the value of what you're offering? What roadblocks exist here and how can you remove them? Have you spoken with existing clients to see how they are using your service and what they feel is missing? What was their feedback and have you implemented it into your system? What is it about their old system that they feel is better than yours / or that yours fails to overcome a certain shortcoming and is not worth the hassle of migration?
I think some digging into your clients is in order. A better picture needs to be painted about their needs and how they perceive that value that you offer.
Customer's digital footprint should give you some directions.
a) Find out how much customer account's on an average spend in a day
b) Find out how many average time users from that customer account spend time.
c) Figure out those that are spending above average time on your website.
d) figure out the pages they are spending the time most.
e) reach out to them and ask for feedback as to what can improve their experience and reduce their hiring time.
f) Once you have validated that the features you have built are things active customers value, then its provides immense confidence to price.
Instead of monthly subscription, help them with a lower threshold subscription for them to try.
7 day free trial may not really work.
First of all, you need to understand their business relationship with you. This is the most vital thing. You can't just upgrade and tell them to pay or else they'd just go somewhere else.
When it comes to the expense of generating new business vs retaining, the latter one is cheaper. So, it's either you give them 2 or 3 months free for their annual subscriptions or provide them VIP access (considering you have tiers on your service) for added value.
You need to understand that they are the early adopters of your business model and this should not entirely be about the "immediate profit" but the long-term relationship.
If you need help in creating an organized onboarding for your previous customers, you can book a call with me here at Clarity.