Tracking deal progress with custom milestones in Recapped for enterprise sales

If you’re managing complex, high-stakes enterprise deals, you already know: spreadsheets, sticky notes, and even traditional CRMs just don’t cut it. Things get lost. Accountability slips. Suddenly, you’re chasing signatures with no idea who’s dropped the ball. This guide is for sales teams who need a clearer way to track deal progress—without buying into yet another overhyped “revenue platform.”

We’re talking about using Recapped and its custom milestones. Here’s how to set it up, what works, what doesn’t, and how to avoid common traps.

Why Custom Milestones? (And When You Actually Need Them)

Let’s get real: most sales tools promise the moon, but deal tracking rarely matches real life. Your sales process probably doesn’t fit the default “Discovery → Demo → Proposal” pipeline. Every enterprise deal has its own quirks—legal reviews, security audits, exec buy-in, and random curveballs.

Custom milestones let you map your actual sales process, not some one-size-fits-all fantasy. You break deals into the steps that matter for your buyers and your team. The result? Less guesswork, fewer dropped balls, and a better shot at closing.

But: If you’re closing quick, transactional deals, don’t bother. The extra setup isn’t worth it. This is for multi-stage, slow-burn deals—think six-figure contracts, multiple stakeholders, complicated sign-offs.

Step 1: Map Your Real Sales Process (Don’t Phone This In)

Before you touch Recapped, grab a whiteboard or a blank doc. Write out how your big deals actually move from cold lead to closed/won. Ask your team:

  • What are the major checkpoints? (Not every tiny task, just the big rocks.)
  • Where do deals get stuck or lost?
  • Who needs to say “yes” at each stage?

Typical enterprise milestones might include:

  • Solution alignment call
  • Technical validation / security review
  • Legal review (always slower than you want)
  • Executive sponsor sign-off
  • Procurement
  • Contract sent
  • Deal closed

Pro tip: Don’t list 15 steps. If you can’t remember them without a cheat sheet, neither will your team.

Step 2: Set Up Custom Milestones in Recapped

Now, jump into Recapped and build your milestones. Here’s the honest take: Recapped makes this pretty straightforward, but don’t expect it to magically fix a broken process. Garbage in, garbage out.

How to create custom milestones:

  1. Log in and open your workspace.
    If you’re not an admin, you’ll need one for full milestone control.

  2. Navigate to your deal pipeline or template section.
    Find the “Milestones” or “Stages” area—depends on your Recapped plan.

  3. Add your custom milestones.

  4. Use clear, simple names (“Legal Review” beats “Due Diligence & Contractual Risk Assessment”).
  5. Add descriptions if your team keeps asking, “What’s this mean?”

  6. Drag and drop to reorder.

  7. Save and set defaults.

  8. Most teams use the same milestones for all enterprise deals. But you can customize per deal or template if needed.

  9. (Optional) Add tasks or owners for each milestone.

  10. This helps if you want to track who’s on the hook at each step.

What to ignore:
Don’t waste time color-coding stages or adding milestones just to “look thorough.” Nobody cares if it’s blue or green. Focus on clarity.

Step 3: Roll It Out Without Losing the Team

Here’s where most rollouts fail: leadership sets up milestones, sends a Slack message, and expects magic. Instead, do this:

  • Walk the team through the milestones.
    Show how a real deal would move through each one. Use a real-world example.
  • Explain what “done” looks like at each stage.
    If “Legal Review” means “contract sent to legal,” say so. If it means “signed off by legal,” be clear.
  • Get feedback.
    Someone will notice a missing step or a stage that’s pointless. Fix it now, not six months in.

Pro tip:
Tie milestones to actual next steps and owners. “Legal Review” isn’t done just because you CC’d legal—track who’s responsible and what’s needed to move forward.

Step 4: Actually Track Deals (And Spot Problems Early)

With milestones live, use Recapped to track every enterprise deal. Don’t let it become shelfware.

How to make it stick:

  • Update milestones as deals move.
    Make this part of your regular pipeline reviews. If a deal’s stuck, the milestone should show where and why.
  • Use Recapped’s reporting (but don’t trust it blindly).
    Most dashboards tell you what should be happening, not what’s actually happening. Check in with reps, especially on deals stuck in the same milestone for too long.
  • Look for patterns.
    Are half your deals dying at “Security Review”? Time to fix that bottleneck, not add more stages.

What doesn’t work:
Don’t try to use milestones as a substitute for real communication. No CRM replaces talking to your team (or your buyers).

Step 5: Adapt As You Learn (And Keep It Simple)

Even the best milestone setup needs tweaking. Over time, you’ll spot steps that are pointless, missing, or need clarifying.

How to iterate:

  • Review every quarter.
    Ask: Are milestones helping, or just extra admin work?
  • Trim the fat.
    If nobody uses “Initial Technical Alignment,” kill it.
  • Add only when necessary.
    New blockers? Add a milestone, but only if it helps you take action.

Avoid these traps:

  • Over-engineering.
    If you need a training manual, you went too far.
  • Ignoring feedback.
    Your reps know where deals really get stuck. Listen to them.

Pro Tips (The Stuff That Actually Helps)

  • Keep milestone names buyer-centric.
    “Executive Signed Off” is clearer than “Internal Stage 4.”
  • Use Recapped’s collaboration features.
    Share milestones with buyers (when appropriate) to set expectations and drive accountability.
  • Track milestone duration.
    If deals keep stalling at one stage, dig into why—don’t just blame the customer.
  • Don’t make milestones a checkbox exercise.
    They’re there to drive action, not to make your pipeline look pretty.

Wrapping Up: Iterate, Don’t Overthink

Tracking enterprise deals with custom milestones in Recapped isn’t about building the world’s fanciest sales process. It’s about making your deals easier to manage and less likely to fall apart in the final mile. Start simple, get feedback, and don’t be afraid to cut steps that don’t help.

Keep iterating, stay skeptical of fancy dashboards, and remember: the best process is the one your team actually uses.