Great question, Ashit! Automation for follow-ups can be a game-changer, but keeping it human is the trick. For pdftopdf.ai, I’ve found success using tools like HubSpot and Customer.io. They allow you to set up email sequences that feel personalized by using dynamic fields (like names or specific actions users have taken), so the messages don’t come off as robotic.
The key is mapping out your follow-up flow. For example, if a trial user uploads their first document but doesn’t convert, I send a helpful tip or highlight a feature they haven’t explored. If they haven’t engaged at all, I might follow up with a “Hey, did you get stuck?” email—simple and conversational.
Also, spacing follow-ups is critical. Too frequent, and it feels pushy; too sparse, and they might forget about you. A little humor or storytelling in your copy can go a long way in keeping things human.
What tools are you using currently, and what’s the biggest challenge you’re facing? Maybe we can brainstorm something together!