Setting Up Labeled Investment in Span

Overview

Labeled Investment lets you understand how your engineering effort is distributed across investment categories — such as New Features, Tech Debt, Maintenance, and Bug Fixes — by mapping your Jira issues to those categories using rule-based matching.

Unlike AI-powered Workstreams, Labeled Investment is fully rule-driven: Span reads explicit fields from your Jira issues (labels, epics, components, custom fields) and rolls up effort accordingly. This makes it a great fit for teams that already have consistent Jira tagging practices.

What you get out of it:

• A clear breakdown of engineering investment by category (e.g., 60% Features, 20% Tech Debt, 20% Maintenance)

• FTE Days and cost allocation per category

• Historical trending of investment mix over time

How It Works

1. You define Focus Areas — high-level investment groupings (e.g., "Engineering Investment")

2. Within each Focus Area, you define Categories (e.g., New Feature, Bug Fix, Tech Debt)

3. For each category, you configure Matching Rules based on Jira fields

4. Span evaluates each issue against your rules (first match wins) and assigns it to a category

5. Work linked to those issues (PRs, commits) inherits the category for FTE rollup

Note: Each issue is assigned to exactly one category per Focus Area — no double-counting.

Prerequisites

• Your Jira integration must be connected to Span

• You should have a consistent tagging strategy in Jira (labels, epics, components, or custom fields) that you want to map to investment categories

• Admin or Settings access in Span

Step 1: Navigate to Investment Settings

Go to Settings → Investment Settings → Investment Areas.

You'll see the Investment Area Settings panel, which lists any existing Focus Areas and allows you to create new ones.

Step 2: Create a Focus Area

A Focus Area is the top-level grouping that holds your categories.

1. Click "Create Focus Area"

2. Enter a name for the Focus Area (e.g., Engineering Investment, Work Classification)

3. Proceed to the next step to add categories

Most teams need only one Focus Area. You can create multiple if you want to slice investment differently for different audiences (e.g., one for product, one for infrastructure).

Step 3: Define Your Categories

Categories represent the investment types you want to track. Common examples:

For each category, you'll configure:

• Name — what appears in reports and charts

• Color — for visual differentiation in dashboards

• Matching Rules — which Jira issues belong to this category

Step 4: Configure Matching Rules

This is the core of Labeled Investment setup. For each category, you define one or more rules that Span uses to classify Jira issues.

Supported Jira Fields for Matching

Available Operators

Equals · Contains · Starts With · Ends With · Is / Is Not · In (multiple values)

Rules can be combined with AND / OR logic.

Example Rule Configuration

Category: New Feature

Rule 1: Epic Label EQUALS "roadmap-feature"
   OR
Rule 2: Issue Label CONTAINS "feature"
   OR
Rule 3: Custom Field "Work Type" EQUALS "Feature"

Category: Tech Debt

Rule 1: Issue Label CONTAINS "tech-debt"
   OR
Rule 2: Epic Title CONTAINS "tech debt"
   OR
Rule 3: Custom Field "Work Classification" EQUALS "Tech Debt"

Rule Evaluation Order

Rules are evaluated in priority order — the first matching category wins. Order your categories from most specific to most general to avoid broad rules capturing issues that should fall into more specific categories.

Tip: Put catch-all categories (like "Maintenance") toward the end of the list.

Step 5: Configure the "Other" Category (Optional)

Enable the "Other" category to act as a catch-all for issues that don't match any of your defined rules. This is recommended — it prevents unclassified work from disappearing from your reports entirely.

Issues in "Other" are a good signal that your rules need refinement or that new work patterns have emerged.

Step 6: Save and Activate

1. Review all categories and their rules in the wizard summary

2. Click Save

Your Focus Area is now active. Span will begin categorizing issues immediately (new/updated issues are processed within a day).

Viewing Your Investment Mix

Once configured, navigate to Investment → Investment Mix to see:

• Breakdown by category — FTE Days per investment type

• Trend over time — how your investment mix has shifted

• Cost allocation (if cost estimates are enabled)

• Per-team or org-wide views

To audit which specific issues were classified into each category, go to Investment → Focus Audit.

Key Rules & Constraints

Tips for a Good Setup

1. Audit your Jira tagging first — Check how consistently your team uses labels and custom fields before writing rules. Inconsistent tagging will result in low classification coverage.

2. Start with your most important categories — Define 4–6 core categories before trying to be exhaustive. You can always add more.

3. Use the "Other" category as a feedback loop — A high percentage of work in "Other" means your rules need expanding. Review it monthly.

4. Align category names with how leadership talks about investment — If your VP calls it "customer-facing work," name the category that, not "New Features."

5. Test rules before finalizing — The category setup wizard shows a live preview of which issues match your rules as you build them.

Troubleshooting

Problem: Most issues are landing in "Other"

• Check that the Jira fields you're matching exist and are consistently populated

• Review rule operators — CONTAINS is often safer than EQUALS for labels with variable formatting

• Confirm your Jira integration is syncing the fields you're targeting

Problem: An issue is assigned to the wrong category

• Check the rule priority order — a broad rule higher in the list may be capturing it before the correct rule fires

• Reorder categories so more specific rules appear first

Problem: A category shows zero issues

• Verify the field value you're matching against exactly matches what's in Jira (case sensitivity, spacing)

• Use CONTAINS instead of EQUALS for labels to handle formatting variations

Problem: Changes to rules aren't reflected yet

• Rule changes apply within ~1 day for new/updated issues; historical data may take longer to reprocess

Related Features

Need help designing your category taxonomy or rule structure? Reach out to your Span customer success contact.