Segmentation Reset Workshop
Identify high-value employer segments to enhance payroll product sales during Selling Season.
Workshop Objective
To help you identify the types of employers most likely to get maximum value from your payroll product and close quickly during Selling Season—so you can direct your sales and marketing focus toward your highest-yield customer segments.
🔄 Step 1: Review the Five Employer Segments
Use Check’s segmentation framework to classify your current and target clients:
Segment | Employee Count | Typical Payroll Setup | Key Messaging | Sales Motion |
Micro SMB | 0–1 | Owner-only, paying self or contractors | S-corp vs. draw education; automate 1099s | Product-led, 1x 15-min call |
Very Small Business | 1–10 | Likely on QuickBooks, accountant involved | QuickBooks integration, local tax support, cost & time savings | Product-led, 1x 15-min call |
Small Business | 10–50 | 50/50 QuickBooks vs. Paychex/ADP/Gusto | Hidden fees, support pain, growing needs | Product-led → 30-min demo |
Midsize | 50–150 | Using legacy providers, more systems involved | Attracting talent, simplifying stack, employee UX | 3 persona demo, bundled pitch |
Mid-Market | 150–500 | Finance + HR + Exec involved | Compliance, budgeting, scalable infrastructure | Consultative sale with multi-persona alignment |
🔍 Step 2: Analyze Your Current Wins by Segment
Exercise: Pull a report of your last 12 months of payroll wins.
Attribute | Ask Yourself |
Company Size | What’s the average employee count of my wins? Any clusters? |
Product Fit | Did the client add any secondary services (e.g., workers comp, retirement)? |
Decision Timeline | Which segments closed fastest? Slowest? |
Value Gained | Where do I hear the most feedback on ROI (time saved, cost saved)? |
Support Load | Which segment is easiest to support post-sale? |
💡 Tip: For newer partners without much closed-won data, analyze your best demo conversations or top-of-funnel activity to approximate fit.
🧠 Step 3: Define Your Best-Fit Client Segment
Based on your analysis:
- Choose 1–2 segments from the Check framework that are most aligned with your product’s capabilities and value.
- Write out your “Ideal Customer Snapshot” for Selling Season:
Our best-fit client is typically a [company size] employer in [industry or pain point] who is currently using [legacy provider or QuickBooks]. They value [support, speed, integrations] and are looking to [improve payroll compliance / simplify systems / save time].
📋 Step 4: Audit Your CRM for Segmentation Alignment
✅ Key Questions:
- Are we capturing:
- Employee count range?
- Industry or NAICS code?
- Current payroll provider?
- Use of benefits, workers comp, or 401(k)?
- Decision-maker persona(s)?
- If yes:
- Build a Rolling Report showing all active and new leads that match your Best-Fit Snapshot.
- Share this with sales and marketing weekly.
- If no:
- Use the guide below to begin collecting this info.
🛠️ Step 5: Fix Gaps in Data Collection
If You’re Not Capturing These Fields:
Info to Capture | How to Start |
Employee count | Add to intake form or ask in every discovery call |
Industry | Use dropdown in CRM or manually tag by NAICS |
Current provider | Add as a field in CRM or discovery notes |
Support pain points | Ask “What’s been your biggest payroll headache?” |
Secondary services | Add checklist to demo form: workers comp, 401k, health, etc. |
📈 Step 6: Activate Segmentation in Selling Season
- Filter outbound and campaign targeting to Best-Fit segments
- Refine demo decks with messaging for your top 1–2 segments
- Use Rolling Reports to focus follow-ups and prioritize pipeline
- Train reps on persona-specific objections for your chosen segment(s)
🧩 Bonus: Team Brainstorm Prompts
Use these questions in a team session to validate assumptions:
- “If you could clone one client, who would it be?”
- “Where do we lose least often?”
- “What kinds of companies light up when we show them the platform?”
Last updated on September 23, 2025