If your deals keep stalling because “someone forgot to follow up,” you’re not alone. Chasing prospects is tedious, and nobody wants to spend their day buried in reminders. But if you’re using Oppwiser, you’ve actually got a decent toolkit for automating follow up tasks—without having to duct-tape together a bunch of tools. This guide is for sales folks, founders, or anyone tired of deals going cold because the ball got dropped.
Let’s break down exactly how to set up automatic follow ups in Oppwiser, what’s worth automating (and what isn’t), and a few honest warnings about where automation can backfire.
Why Automate Follow Ups? (And When Not To)
You already know following up is critical—most deals don’t close on the first call. But relying on memory or sticky notes isn’t a system; it’s a recipe for missed revenue. Automation in Oppwiser can:
- Save you hours on repetitive admin work
- Prevent prospects from slipping through the cracks
- Make your pipeline less chaotic and more predictable
But, a word of caution: Not every follow up should be a robot. If you’re chasing a big deal, or the next step requires finesse (like negotiating terms), keep it manual. Oppwiser’s automation is best for routine nudges, reminders, or scheduling—not delicate conversations.
Step 1: Audit Your Current Follow Up Process
Before you automate anything, get clear on what’s actually happening in your sales workflow. Otherwise, you’ll just automate chaos.
- List your touchpoints: Where do you follow up? (After a demo, post-proposal, when a prospect ghosts you…)
- Identify bottlenecks: Where are deals stalling? Is it because someone forgot to check in, or is there another reason?
- Decide what’s repeatable: Only automate tasks that happen the same way each time (e.g., “Send a reminder 3 days after proposal”).
Pro tip: Don’t try to automate everything at once. Start with the most common, boring follow-up task you do every week.
Step 2: Get Familiar with Oppwiser’s Automation Tools
Oppwiser offers a few ways to automate follow ups. Here’s what’s available as of mid-2024:
- Task automation: Automatically creates follow up tasks based on pipeline stage or triggers.
- Email templates: Lets you send semi-personalized emails on autopilot.
- Sequences: String together a series of emails, tasks, or reminders over time.
The UI is pretty straightforward, but don’t expect the polish of Salesforce or HubSpot. What matters: it gets the job done, and you don’t need an IT degree to set it up.
Step 3: Map Your Follow Up Triggers
This is where most people get it wrong—they automate random stuff and wonder why nothing moves. Instead, figure out exactly when you want a follow up to trigger.
Typical triggers worth automating:
- Stage change: When a deal moves from “Demo Completed” to “Proposal Sent,” create a follow up task for 2 days later.
- No response: If a prospect hasn’t replied in X days, send a gentle nudge.
- Task completion: When you finish a call, automatically set a “send recap” task for later that day.
Avoid triggers like “any time a new lead comes in”—that’s just noise.
Step 4: Build a Simple Automation in Oppwiser
Let’s walk through a bread-and-butter example: automatically creating a follow up task after sending a proposal.
- Go to your pipeline settings: In Oppwiser, find the pipeline you want to automate (usually under Settings > Pipelines).
- Select the relevant stage: For example, “Proposal Sent.”
- Add an automation rule: Look for “Add Automation” or similar. Choose the trigger “when deal enters this stage.”
- Set the action: “Create follow up task.” You can usually set the due date (e.g., 3 days after entry).
- Write the task description: Keep it actionable, e.g., “Check in on proposal status with [contact first name].”
- Save and test: Move a dummy deal into this stage and make sure the task pops up.
What to watch out for:
- Oppwiser’s automations are basic. If you want multi-step, branching logic, you’ll hit a wall.
- Some integrations (like with Gmail or Outlook) can be glitchy. Always test with your actual workflow.
Step 5: Automate “No Response” Nudges (Without Being Annoying)
Automating a polite follow up when someone goes dark is where Oppwiser can shine—if you don’t overdo it.
- Set up a “no activity” trigger: In the automation settings, look for something like “If no reply in [X] days.”
- Choose your action:
- Create a follow up task (recommended—you get to personalize).
- Or, send a templated follow up email (riskier—see below).
- Write your template or task: Keep it short and human, not robotic. For emails, resist the urge to send “just checking in” messages—add value or context.
- Limit the frequency: Don’t set up more than 2-3 nudges per deal, or you’ll get flagged as spam (or just ignored).
Honest take:
Auto-emails can save time but can also tank your reputation if they sound canned or keep pestering prospects. A task that reminds you to check in (so you can personalize) is usually safer.
Step 6: Use Sequences for Long, Repetitive Drip Campaigns
If your sales cycle is long and involves multiple touchpoints (like you’re nurturing cold leads), Oppwiser’s sequences can help.
- Build your sequence: Combine emails and tasks, spaced out over days or weeks.
- Keep it tight: 3-4 steps is usually plenty. Don’t build a 12-step sequence—nobody has the patience for that.
- Monitor response rates: If engagement drops off after the second step, trim your sequence.
- Pause for replies: Make sure Oppwiser stops the sequence if someone responds—nothing kills a deal like an auto-email after a real conversation.
Step 7: Review, Adjust, and Don’t Set-and-Forget
Automation isn’t “fire and forget.” Check in every couple of weeks:
- Are follow ups happening when they should?
- Are deals moving forward, or are you just generating more tasks?
- Are prospects actually replying, or are they tuning you out?
Be honest with yourself—if something feels spammy, it probably is. Tweak your automations, adjust timing, or pull back if needed.
What’s Not Worth Automating (Yet)
Some things are still better handled by humans:
- Custom proposals or high-stakes negotiations: Templates won’t cut it.
- Personal, relationship-building emails: If you’re building trust, automation isn’t your friend.
- Complex deal handoffs: If more than one team is involved, automation can drop the ball.
Oppwiser is great for the routine stuff, but you can’t (and shouldn’t) automate your way to every closed deal.
Pro Tips and Pitfalls
- Keep your automations visible: Document what you’ve set up. Otherwise, you’ll forget what’s running and create a mess.
- Start small: Automate one task, see if it helps, then add more.
- Don’t copy-paste generic templates: Everyone can tell, and it makes you look lazy.
- Watch for system updates: Oppwiser’s features change—sometimes automations break after an update. Check after every big release.
TL;DR: Keep It Simple, Rinse, Repeat
Automating follow ups in Oppwiser isn’t rocket science. Start with your most boring, repeatable tasks. Test, tweak, and don’t be afraid to turn things off if they aren’t helping. The goal isn’t to replace yourself—it’s to free up your brain for the conversations that actually close deals.
Iterate, pay attention, and keep your automations simple. That’s how you keep deals moving—without losing your sanity.