If you’re tired of emailing prospects over and over—“Just checking in!”—you’re not alone. Chasing after proposals is the least rewarding part of sales, and it’s easy to let follow-ups slip. This guide is for anyone who wants to stop losing deals just because they forgot to nudge someone. We’ll walk through how to use Proposable to take follow-up off your plate, for good.
No fluff, no magic bullets—just a clear, real-world way to make sure your proposals get the attention they deserve, without you becoming a professional nag.
Why Automate Proposal Follow Ups?
Let’s get this out of the way: most deals don’t close on the first try. People are busy, inboxes are full, and your proposal is probably not the only one sitting there. If you rely on your memory or a pile of sticky notes, you’ll miss opportunities and let deals stall.
Here’s what happens when you automate follow ups:
- You stop worrying about “dropping the ball.”
- Prospects get timely, professional nudges.
- You free up hours for actual selling (or, you know, having a life).
But automation isn’t magic. If your follow-ups sound like spam, you’ll still get ignored. The trick is to set things up so your messages are relevant, polite, and don’t cross over into “annoying robot” territory.
Step 1: Get Your Proposals Into Proposable
Before you can automate anything, you need your proposals running through Proposable.
- Create or import your proposal templates. Proposable lets you build proposals from scratch, or use templates. Don’t overthink it—start with something simple.
- Add your branding and standard sections (pricing, terms, etc.) so you’re not reinventing the wheel every time.
- Send a test proposal to yourself. Make sure everything looks the way you want, and check the client’s view. You don’t want your first real follow-up going out with typos or broken links.
Pro tip: If you’ve got old proposals living in Word or PDF, don’t waste hours copy-pasting every past deal. Just get your current offerings into Proposable. You can always tweak as you go.
Step 2: Set Up Automated Follow Up Sequences
Here’s where the real time-saver comes in. Proposable lets you set up automated reminders that go out to your prospects if they haven’t viewed, responded to, or signed your proposal.
How to Do It
- Go to your proposal settings. When you’re building or editing a proposal, look for the “Reminders” or “Follow Up” tab.
- Choose your triggers:
- Viewed: Send a follow-up if the client viewed but didn’t act.
- Not viewed: Remind if they haven’t opened it at all.
- Not signed/accepted: Nudge if they looked but didn’t sign.
- Set your schedule:
- Pick how many days to wait before each reminder (e.g., 2 days after no view, 5 days after no signature).
- Decide how many reminders to send (don’t overdo it; more on this below).
- Customize your messages:
- Edit the subject and body. Use the prospect’s name and proposal details—Proposable can pull these in automatically.
- Keep it short and human. If you wouldn’t say it to someone’s face, don’t automate it.
Example message:
Hi {{client_name}},
Just wanted to check if you had a chance to review the proposal. Let me know if you have any questions or if there’s anything holding things up.
What Works (and What Doesn’t)
- Works: Two or three reminders, spaced out over a week or two. Clear, polite language.
- Doesn’t work: Daily emails, all-caps subjects, or guilt-tripping (“Why haven’t you signed yet???”).
- Ignore: Anyone telling you to “automate your entire sales process.” Follow ups help, but they won’t close the deal for you.
Step 3: Track Engagement and Know When to Jump In
Automation is great, but it’s not a substitute for actual selling. The good news is, Proposable gives you a lot of visibility into what’s going on with your proposals.
- See who’s opened your proposal, when, and how many times.
- Get notified if someone forwards your proposal internally. (Useful for B2B deals.)
- Track status: viewed, accepted, signed, or ignored.
When to Step In
If your prospect opens your proposal three times in two days, but still hasn’t signed, that’s your cue to call or send a personal note. Automation gets you most of the way, but sometimes deals need a human touch.
Warning: Don’t just set and forget. Check your dashboard every few days. Automated reminders are a safety net—not a replacement for paying attention.
Step 4: Fine-Tune (And Don’t Annoy People)
Not every prospect wants or needs three reminders. If you notice a lot of unsubscribes or get grumpy replies, dial back your follow-ups.
- Start with a conservative schedule: 2-3 reminders max, 2–5 days apart.
- Check response rates: If people are ignoring your emails or saying they didn’t see them, tweak your subject lines and timing.
- Personalize when it matters: For big deals, skip automation entirely for the last nudge and write a quick, personal note.
Pro tip: It’s better to under-remind than to end up in the spam folder. You want to be persistent, not a pest.
Step 5: Keep Your Team on the Same Page
If you’re not a solo act, Proposable’s automation can help your whole team stay organized.
- Assign proposals to team members.
- See who’s responsible for each follow up.
- Share templates and messaging, so everyone’s not inventing their own tone.
But don’t get bogged down in endless approvals or meetings. Set up your templates, agree on a follow-up cadence, and let the tool do its thing.
What to Ignore (and What to Watch Out For)
- Ignore the hype: Automated follow ups won’t magically turn “no” into “yes.” They just make it less likely you’ll lose because you forgot to ask.
- Don’t over-automate: If you automate every single part of the process, your outreach will start to sound robotic. People notice.
- Watch your open and response rates: If you see a drop, revisit your messaging. The market changes, and so should you.
Keep It Simple, Iterate, and Close More Deals
You don’t need fancy workflows or ten-step automations. Start small: automate basic reminders, track the results, and adjust as you go. The goal is to spend less time following up and more time actually talking to customers (or, honestly, doing anything else).
Set up your Proposable automations, keep your messaging human, and don’t let “perfect” get in the way of “good and done.” You’ll close more deals—and you’ll never send another “Just bumping this up in your inbox” email by hand again.