Cutting through sales cycle fluff isn’t just for ops nerds—it’s for anyone who’s tired of deals dragging on for no clear reason. If you’re in sales leadership, ops, or just want to help your reps close faster, this guide is for you. We'll get hands-on with Setsail, but the principles apply even if you’re just trying to make sense of deal velocity in general.
Too many teams treat sales cycle analysis like a check-the-box exercise. That’s a mistake. When you actually dig into your cycle lengths and spot the bottlenecks, you stop sweating “activity metrics” and start fixing what matters. Here’s how to do it without getting lost in the weeds—or hoodwinked by pretty dashboards that don’t tell you anything new.
Step 1: Get Clear on Why You’re Measuring Sales Cycle Length
First, don’t analyze just because someone told you to. Cycle length isn’t a vanity metric, but it can become one if you’re not careful.
What matters: - Where do deals stall? You want to find choke points, not just average days. - Are your long cycles actually the problem? Sometimes slow deals are just bigger or more complex—don’t punish what’s normal. - Do you have a baseline? If you don’t know your current cycle, improvement is guesswork.
What doesn’t matter: - Comparing to internet “benchmarks.” Your business, your sales motion. - Obsessing over outliers—one monster deal won’t help you fix the process for everyone else.
Pro tip: Before you open Setsail, write down what you’re actually hoping to change. Faster onboarding? Fewer stuck deals? More accurate forecasts? Your answer shapes how you’ll use the data.
Step 2: Set Up Your Pipeline Data in Setsail
You can’t improve what you can’t see. Setsail is only as good as the data you feed it.
Checklist: - Stages are mapped. Make sure your CRM stages correspond to the steps Setsail tracks. Garbage in, garbage out. - Deal start and end dates are accurate. Setsail calculates cycle length by looking at when opportunities are created and closed—don’t fudge these. - Custom fields? If you use custom milestones, talk to your admin about syncing those with Setsail. Otherwise, you’ll miss the real bottlenecks.
What to ignore: Don’t get sucked into tracking every email or call. Focus on meaningful stage changes—those are what actually move a deal forward.
Heads up: If your team is bad about updating CRM stages, Setsail can only do so much. Fix the process, not just the tool.
Step 3: Break Down Your Sales Cycle By Stage
This is where most teams go wrong—they look at the total cycle, but never ask where time is being lost.
In Setsail: 1. Open the Sales Cycle dashboard. 2. Filter by date range, segments, or product lines as needed. Don’t mix SMB and enterprise if one always takes longer. 3. Look for the stage-by-stage breakdown. Setsail usually shows how long deals spend in each stage (e.g., Discovery, Proposal, Negotiation).
What to look for: - Stages with the biggest time sinks. Is “Legal Review” eating up weeks? Are deals stuck in “Value Prop” because reps are underprepared? - Variability. Are some reps consistently faster in certain stages? Why? - Drop-off points. If deals die in one stage, that’s a different problem from slow-moving but successful deals.
What not to obsess over: Don’t just average everything—look for patterns. If one stage is always slow, that’s your clue.
Step 4: Slice the Data
Broad averages hide the real story. Use Setsail’s filters to break down your sales cycle by:
- Rep. Who’s consistently slow or fast? (But don’t start witch hunts—context matters.)
- Deal size. Big deals should take longer. If your small deals drag, that’s wasted effort.
- Industry or segment. Certain customers will always move slower—no tool can fix that.
- Closed-lost vs. closed-won. Are losing deals always slow, or do they drop out early?
Pro tip: Setsail lets you export most reports. Pull it into a spreadsheet if you want to do your own analysis—sometimes you’ll spot patterns Setsail misses.
Step 5: Spot (and Question) the Bottlenecks
Now comes the real work: figuring out why deals get stuck.
Common bottlenecks: - Internal handoffs. Waiting on approvals or legal. - Customer engagement gaps. Long silences after a demo? Maybe your message isn’t landing. - Proposal stage. Are reps slow to generate quotes, or is the process too manual? - Procurement hell. Some customers just move slow—don’t waste energy trying to “fix” them.
What works: - Talk to reps. The data tells you where; your team can tell you why. - Look for repeat offenders. If it’s always the same stage, the process is broken—not the people.
What doesn’t: - Micromanaging based on small sample sizes. - Chasing every outlier—focus on patterns.
Ignore: Fancy AI-generated “insights” that don’t match the reality on the ground. Setsail can flag trends, but real problem-solving still takes human judgment.
Step 6: Set Realistic Targets for Improvement
You’ve found your bottlenecks. Now, what’s actually fixable?
How to set targets: - Pick one or two stages to improve. Don’t try to fix everything at once. - Set specific, time-bound goals. “Reduce time in Proposal stage from 8 days to 5 days in Q3.” Vague goals go nowhere. - Involve the team. Get buy-in from people actually doing the work. Otherwise, you’ll get “process theater” and nothing will change.
What to avoid: - Arbitrary targets from execs who don’t know the process. - Pushing for faster cycles when the real issue is deal quality or fit.
Step 7: Test, Track, and Iterate
You can’t improve what you don’t revisit. Setsail is great for trend-watching, but you still need to drive the follow-through.
Best practices: - Check your dashboards every week or two—not daily. Trends matter more than daily blips. - Share wins and roadblocks openly. If a new process cuts a stage down by 3 days, celebrate it. If it flops, adjust. - Revisit your baselines. Cycle length won’t fix itself. Keep asking, “Is this still our biggest bottleneck?”
Don’t bother: - Building a monster dashboard no one reads. - Measuring for measurement’s sake. If a report never leads to action, scrap it.
Honest Takes and Common Gotchas
What works: - Focusing on why deals stall, not just how long. - Connecting data to real process fixes—like automating proposal creation or clarifying handoffs. - Using Setsail as a flashlight, not a crystal ball—it shows you where to look, not what to do.
What doesn’t: - Expecting instant results. Process change is slow, and salespeople are (rightly) skeptical. - Getting lost in averages instead of digging into the “why.” - Blindly trusting any tool to diagnose or solve every problem. Tools amplify good process—they don’t replace it.
Keep It Simple and Keep Going
Sales cycle analysis isn’t a one-off project. The key is to keep your approach simple, focus on the stages that matter, and actually act on what you see. Don’t drown in reports—pick a bottleneck, fix it, and check the numbers again in a month. Rinse and repeat.
If you’re using Setsail, great—it’ll save you time. But the real work is asking the right questions and making process tweaks that stick. Don’t let shiny dashboards distract you from what your team already knows: the best way to sell faster is to remove the stuff that slows you down. Keep it practical, and you’ll see results.