If you're in B2B sales, you know follow-up isn’t optional—it’s the whole game. But keeping track of who needs a nudge, when to check in, and what needs to happen next? That’s where things get messy and deals go to die. If you’re tired of dropping the ball (or letting your team do it), automating follow-up tasks with Pickleai can actually help. But let’s cut through the hype: automation won’t magically make you a sales superstar. It will keep your process tight and stop you from forgetting the basics.
This guide is for sales managers, reps, and anyone who’s got a pipeline full of “let’s circle back” and “touching base” emails. Here’s how to set up Pickleai to do the boring stuff, so you can focus on actually closing.
Step 1: Map Out Your Real Follow-Up Process
Before you even open Pickleai, get clear on your follow-up flow. Automation is only as smart as what you tell it to do. Don’t just copy a generic sequence.
Ask yourself: - After an intro call, what’s your next step? (Send info, book demo, etc.) - Who needs reminders—just you, or the whole team? - How often do you check in before calling a deal dead? - What “triggers” actually matter? (Lead replies, no response in 5 days, contract sent, etc.)
Pro tip: Write this out, step by step, on a notepad or whiteboard before touching Pickleai. Otherwise, you’ll end up automating chaos.
Step 2: Set Up Pickleai and Connect Your Tools
Pickleai only works if it’s plugged into the rest of your stack. Here’s what to do:
- Sign up and log in: Obvious, but worth saying.
- Connect your CRM: Pickleai integrates with most popular CRMs (Salesforce, HubSpot, etc.). Don’t skip this, or you’ll be copy-pasting data forever.
- Email/calendar access: Link your work email and calendar. Otherwise, Pickleai can’t scan for replies or meetings.
- Import current deals: Make sure your open opportunities are showing up in Pickleai, or you’re automating nothing.
What to ignore:
Don’t get lost setting up integrations you don’t use. Stick to the basics—CRM, email, and calendar. If Pickleai promises “AI-powered enrichment” but can’t even see your pipeline, you’re wasting your time.
Step 3: Build Follow-Up Task Templates
Now for the core of automation: telling Pickleai exactly what follow-ups to create, and when.
How to do it:
- Go to “Automations” or “Workflows” in Pickleai.
- Create a new workflow: Name it something you’ll recognize, like “Demo Follow-Up Sequence.”
- Add triggers: These are the events that start the follow-up sequence. Pick what matters (e.g., “Deal moved to Proposal Sent” or “No response after 3 days”).
- Define tasks: For each trigger, spell out the tasks you want created. Example:
- Task 1: “Send follow-up email with proposal summary.”
- Task 2: “Call prospect if no reply in 2 days.”
- Task 3: “Loop in manager for stalled deals after 7 days.”
- Assign owners: Decide who gets each task (yourself or teammates).
Honest take:
Don’t try to automate every tiny step. Focus on the follow-ups that actually move deals forward. If you create a 10-step process for every lead, you’ll drown in reminders and start ignoring them.
Step 4: Personalize Your Follow-Ups (Don’t Sound Like a Robot)
Pickleai can send emails and reminders for you, but canned messages are obvious and easy to ignore. Instead:
- Use Pickleai’s dynamic fields to personalize (e.g., {{First Name}}, {{Company}}).
- Write templates that sound like you—don’t lean on generic “Just checking in!” lines.
- Set reminders to review messages before they go out, at least for high-value deals.
Skip this? Only if you’re fine with being tuned out. Automation saves you time, but it can also make you sound like a spam bot if you’re lazy.
Step 5: Set Up Smart Triggers and Conditions
This is where Pickleai actually earns its keep (if you set it up right).
Examples of smart triggers: - “If no reply to proposal in 48 hours, create a ‘Nudge’ task and draft a follow-up email.” - “If lead opens your email but doesn’t reply, schedule a call task for tomorrow.” - “If deal size is over $50k, loop in sales manager automatically.”
What works:
- Use time-based triggers for follow-up (24, 48, 72 hours).
- Use activity-based triggers (email opens, link clicks) to prioritize hot leads.
- Use deal stage changes (e.g., “Moved to Negotiation”) to kick off new tasks.
What doesn’t:
- Overly complex logic—if you need a flowchart to explain it, it’ll break.
- Triggers based on data you don’t have (“If prospect’s budget is X…” when you never collect that info).
Tip: Start simple. You can always add more triggers—just make sure they actually help you move deals, not just fill your to-do list.
Step 6: Test Your Automation (Don’t Let It Go Rogue)
The fastest way to cause chaos is launching an untested automation. Here’s how to avoid that:
- Test on fake deals: Create dummy leads and run them through your workflow.
- Check your inbox: Make sure reminders and emails land where you expect.
- Review tasks created: Are they assigned to the right people? Are due dates reasonable?
- Ask a teammate to try it: Fresh eyes catch what you miss.
Ignore:
Pickleai’s “test mode” is helpful, but don’t trust it blindly. Always do a manual walkthrough with real or fake data.
Step 7: Monitor, Adjust, and Don’t Set It and Forget It
No automation is perfect out of the box. Every sales cycle is different, and things change.
- Review your open tasks weekly: Are deals moving faster? Any bottlenecks?
- Tweak your workflows: Drop steps nobody uses. Add new ones if a stage is always getting stuck.
- Ask your team for feedback: If reminders are just noise, they’ll get ignored. Fix that fast.
What works:
- Keeping workflows lean—2-4 steps per follow-up is usually enough.
- Regular review. Set a recurring calendar reminder to check Pickleai’s effectiveness.
What doesn’t:
- Letting automations run for months without checking. You’ll end up with a swamp of overdue tasks and annoyed reps.
Pro Tips for Real-World Success
- Automate the “boring,” not the relationship: Use Pickleai to remember dates, send reminders, and push nudges—but real conversations close deals.
- Don’t overcomplicate: The more steps you add, the more likely something breaks or gets ignored.
- Audit your messages: Once a month, read what Pickleai is sending. If you’d delete it on sight, rewrite.
- Use “pause” buttons: For deals that go dark or prospects on vacation, make sure you can pause automations so you don’t look tone-deaf.
Keep It Simple, Iterate, and Actually Close More Deals
Automating your follow-ups in Pickleai isn’t magic. But if you map your real process, connect your tools, and keep things simple, you’ll stop things slipping through the cracks. Start with the basics, see what actually works in your pipeline, and tweak as you go. Sales is already hard enough—let your tools do the grunt work, so you can focus on what actually matters: talking to people and closing deals.