Sales AI Skill

Deal Health Risk Scoring

Identify at-risk deals before they slip using deal health scores and risk alerts. Use when monitoring pipeline health, identifying deals at risk of stalling or losing, creating deal risk dashboards, or setting up automated deal health alerts. Triggers on ph...

Deal Health Scoring & Risk Alerts

Proactively identify at-risk deals before they slip through automated health scoring, risk factor analysis, and early warning alerts.

Workflow

  1. Define deal health factors and their weights (engagement, multi-threading, champion strength, timeline, competition).
  2. Calculate real-time health score for every open opportunity.
  3. Flag deals with declining health scores or scores below threshold.
  4. Alert sales rep and manager with specific risk factors and suggested remediation.
  5. Track remediation actions and measure impact on health score recovery.
  6. Generate weekly pipeline health reports and risk trend analysis.

Deal Health Scoring Model

DEAL HEALTH SCORING FRAMEWORK
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Health Factor 1 — Engagement Level (Weight: 25%):
  Scoring Criteria:
    → Activity frequency (touches in last 7 days):
        3+ touches/week: +25 points (high engagement)
        1–2 touches/week: +15 points (moderate engagement)
        < 1 touch/week: +5 points (low engagement)
    → Activity quality:
        Meetings held (discovery, demo, exec alignment): +5 per meeting
        Emails exchanged (bidirectional): +3 per meaningful exchange
        Calls made (10+ minutes): +3 per call
        Content engagement (downloads, views): +2 per engagement
    → Response time (prospect to rep):
        < 24 hours: +10 points (highly responsive)
        1–3 days: +5 points (moderately responsive)
        3–7 days: +2 points (slowly responsive)
        > 7 days: -5 points (disengaging)
    → Last touch recency:
        Within 3 days: +10 points
        4–7 days: +5 points
        8–14 days: +2 points
        > 14 days: -10 points (significant risk)
  Maximum Score: 25 points

Health Factor 2 — Multi-Threading (Weight: 20%):
  Scoring Criteria:
    → Number of engaged stakeholders:
        4+ stakeholders engaged: +20 points (excellent multi-threading)
        3 stakeholders: +15 points (good)
        2 stakeholders: +10 points (adequate)
        1 stakeholder: +5 points (single-threaded — high risk)
    → Stakeholder seniority spread:
        Economic buyer + technical buyer + champion: +5 bonus
        VP+ engagement confirmed: +5 bonus
        End-user engagement confirmed: +3 bonus
    → Stakeholder engagement quality:
        All stakeholders responded in last 14 days: +5 bonus
        Champion actively advocating internally: +5 bonus
  Maximum Score: 20 points

Health Factor 3 — Champion Strength (Weight: 20%):
  Scoring Criteria:
    → Champion identification:
        Champion confirmed (self-identified or validated): +15 points
        Champion suspected (based on engagement): +8 points
        No champion identified: +0 points (critical risk)
    → Champion influence level:
        Direct decision-maker (economic buyer): +10 points
        Strong influence (can drive decision process): +7 points
        Moderate influence (can provide input): +4 points
        Weak influence (information gatherer only): +1 point
    → Champion access to decision-maker:
        Direct access (reports to or peers with economic buyer): +10 points
        Indirect access (can arrange meetings): +5 points
        Limited access (information only): +2 points
    → Champion risk factors:
        Champion recent hire (< 3 months): -5 points (may leave)
        Champion negative sentiment detected: -10 points
        Champion engagement declining: -5 points
  Maximum Score: 20 points

Health Factor 4 — Timeline & Urgency (Weight: 20%):
  Scoring Criteria:
    → Timeline specificity:
        Specific close date (day/month): +15 points
        Quarter-specific: +10 points
        Vague timeline ("sometime this year"): +5 points
        No timeline identified: +0 points (critical risk)
    → Timeline urgency:
        Close within 30 days: +10 points (high urgency)
        Close within 30–60 days: +7 points
        Close within 60–90 days: +5 points
        Close > 90 days: +2 points
    → Timeline credibility:
        Budget approved: +10 points
        Budget in process: +5 points
        Budget not identified: +0 points
    → Timeline slippage:
        Close date moved 0 times: +5 bonus
        Close date moved 1–2 times: +0 bonus
        Close date moved 3+ times: -10 points (pattern of delay)
  Maximum Score: 20 points

Health Factor 5 — Competitive Position (Weight: 15%):
  Scoring Criteria:
    → Competitor involvement:
        No competitors: +15 points (sole source)
        1 competitor, we're preferred: +10 points
        1 competitor, equal positioning: +7 points
        1 competitor, they're preferred: +3 points
        2+ competitors: +5 points (complex competitive landscape)
        Incumbent competitor (replacement deal): +0 points (high risk)
    → Differentiation clarity:
        Clear competitive advantage articulated: +10 bonus
        Moderate differentiation: +5 bonus
        Weak differentiation (commoditized): -5 points
    → Battle card alignment:
        Battle card reviewed and applied: +5 bonus
        Competitive strategy documented: +5 bonus
  Maximum Score: 15 points

Health Factor 6 — Deal Complexity (Weight: 10%):
  Scoring Criteria:
    → Deal size vs. average:
        < 2x average deal size: +10 points (standard deal)
        2–5x average: +7 points (larger deal, moderate complexity)
        5–10x average: +5 points (large deal, high complexity)
        > 10x average: +2 points (enterprise deal, very complex)
    → Customization required:
        Standard product offering: +10 points
        Minor customization needed: +7 points
        Significant customization needed: +3 points
    → Implementation complexity:
        Simple implementation (< 2 weeks): +10 points
        Moderate implementation (2–6 weeks): +7 points
        Complex implementation (6–12 weeks): +3 points
  Maximum Score: 10 points

TOTAL HEALTH SCORE: 0–100 points (sum of all weighted factors)

Risk Classification and Alerts

DEAL RISK CLASSIFICATION
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Risk Level 1 — HEALTHY (Score: 75–100):
  Status: Deal progressing well; no immediate action needed
  Alert: None (standard monitoring)
  Check-in: Weekly pipeline review
  Expected close probability: 60–85%
  Action: Continue standard selling process

Risk Level 2 — WATCH (Score: 55–74):
  Status: Deal showing some risk factors; needs attention
  Alert: Email notification to rep within 24 hours of score drop
  Alert Content:
    "⚠️ Deal [Account] health score dropped to [Score]/100
     Risk factors: [Specific factors — e.g., 'Engagement declining',
     'Close date moved 2x', 'No economic buyer engaged']
     Suggested actions: [Personalized remediation steps]
     [Link to deal record] | [Link to remediation guide]"
  Check-in: Bi-weekly pipeline review
  Expected close probability: 30–60%
  Action: Address specific risk factors within 5 business days

Risk Level 3 — AT RISK (Score: 35–54):
  Status: Deal at significant risk of stalling or losing
  Alert: Email + Slack notification to rep AND manager within 2 hours
  Alert Content:
    "🚨 Deal [Account] flagged as AT RISK — Score: [Score]/100
     Top 3 risk factors:
     1. [Risk factor] — Impact: [High/Medium/Low]
     2. [Risk factor] — Impact: [High/Medium/Low]
     3. [Risk factor] — Impact: [High/Medium/Low]
     Required actions: [Specific remediation steps with deadlines]
     Manager review required within 48 hours.
     [Link to deal record] | [Link to risk remediation playbook]"
  Check-in: Weekly 1:1 with manager (dedicated pipeline discussion)
  Expected close probability: 15–30%
  Action: Manager involvement required; remediation plan within 3 days

Risk Level 4 — CRITICAL (Score: < 35):
  Status: Deal highly likely to stall or be lost; immediate action required
  Alert: Slack + Email + Phone notification to rep, manager, AND VP Sales
  Alert Content:
    "🔴 CRITICAL: Deal [Account] score [Score]/100 — Immediate attention
     This deal is at high risk of being lost. Key issues:
     [Detailed risk assessment with specific factors]
     Required: Emergency deal review within 24 hours
     Decision: Salvage plan or close lost
     [Link to deal record] | [Link to escalation process]"
  Check-in: Daily check-in until score recovers or deal closes
  Expected close probability: < 15%
  Action: Emergency deal review; executive intervention if strategic;
         close lost if salvage not feasible

AUTOMATIC ESCALATION RULES:
  → Score drops > 20 points in 7 days: Immediate alert regardless of absolute score
  → Score drops below 50 for first time: Alert + suggested remediation
  → Score below 35 for 14+ days: Auto-escalate to VP Sales
  → Score below 25 for 21+ days: Recommend close lost + re-engagement plan
  → Champion leaves company: Immediate Critical alert
  → Economic buyer indicates switching to competitor: Immediate Critical alert

Risk Remediation Playbook

REMEDIATION ACTIONS BY RISK FACTOR
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Risk Factor: Declining Engagement
  Symptoms: < 1 touch/week, no response in 7+ days, declining email open rates
  Remediation Actions:
    1. "Check-in" email: "Hi [Name], just checking in — everything going well
       with [project/initiative we discussed]?"
    2. Value-add outreach: Share relevant content (case study, industry insight)
       without asking for anything
    3. Phone call: "Hey [Name], wanted to make sure I'm not being too
       aggressive — also wanted to share [quick insight]..."
    4. Stakeholder pivot: Engage different contact at account
    5. Breakup email: "Should I stay or should I go?" — often triggers response
  Timeline: Execute within 3 business days of alert
  Success Metric: Engagement recovery (≥ 1 touch/week within 7 days)

Risk Factor: Single-Threaded Deal
  Symptoms: Only 1 stakeholder engaged, no economic buyer access
  Remediation Actions:
    1. Ask champion for introductions: "Who else should be involved in this?"
    2. Research buying committee: LinkedIn, org chart, company website
    3. Multi-channel outreach: Email + LinkedIn + phone to identified stakeholders
    4. Warm introduction: Request intro from champion or mutual connection
    5. Executive alignment: Offer executive-to-executive meeting
  Timeline: Identify 2+ additional stakeholders within 5 business days
  Success Metric: 3+ engaged stakeholders within 14 days

Risk Factor: Champion Risk (Weak or Departing)
  Symptoms: Champion disengaging, negative sentiment, recent job change
  Remediation Actions:
    1. Identify backup champion: Engage secondary stakeholder immediately
    2. Strengthen current champion: Executive briefing, exclusive insights,
       personalized value demonstration
    3. Deploy champion's champion: Identify and engage champion's boss
    4. Social proof injection: Reference calls with similar customers
    5. Urgency creation: Time-sensitive offer, limited capacity, pricing change
  Timeline: Backup champion identified within 3 business days
  Success Metric: New champion confirmed or current champion re-engaged

Risk Factor: Timeline Slippage
  Symptoms: Close date moved 2+ times, vague timeline, no budget confirmation
  Remediation Actions:
    1. Direct conversation: "I want to be transparent — what's the real timeline?"
    2. Budget discovery: "Has budget been formally approved? Who controls it?"
    3. Mutual action plan: Create shared timeline with milestones and owners
    4. Executive escalation: Executive-to-executive call to set commitment
    5. Pilot/POC: Start with smaller engagement while full deal progresses
  Timeline: Specific close date and budget status confirmed within 7 days
  Success Metric: Close date confirmed and budget approved within 14 days

Risk Factor: Competitive Threat
  Symptoms: Competitor engaged, competitor preferred, incumbent replacement
  Remediation Actions:
    1. Battle card deployment: Review competitor weaknesses and our differentiation
    2. Competitive discovery: "What do you like about [Competitor]? What's
       your biggest concern?"
    3. Switching incentive: Migration support, pricing guarantee, extended trial
    4. Customer deflection stories: Case studies from customers who switched
    5. Technical differentiation: Side-by-side demo highlighting unique capabilities
  Timeline: Competitive strategy executed within 5 business days
  Success Metric: Competitive positioning confirmed or deal won

Pipeline Health Dashboard

PIPELINE HEALTH DASHBOARD METRICS
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Overall Pipeline Health:
  → Average deal health score: [Target: > 65/100]
  → % deals in Healthy zone: [Target: > 60%]
  → % deals in Watch zone: [Target: < 25%]
  → % deals in At Risk zone: [Target: < 10%]
  → % deals in Critical zone: [Target: < 5%]

Deal Age Analysis:
  → Average days in current stage: [Compare to historical average]
  → Deals > 2× average stage duration: [Count and total value]
  → Deals > 3× average stage duration: [Count and total value — immediate review]
  → Oldest deal in pipeline: [Account, value, age, owner]

Engagement Analysis:
  → Deals with no activity in 14+ days: [Count and value]
  → Deals with no activity in 30+ days: [Count and value — stale]
  → Average touches per deal/week: [Target: > 2]
  → Deals with only 1 stakeholder: [Count and value — multi-threading gap]

Risk Trend Analysis:
  → Health score trend (last 30 days): [Improving/Stable/Declining]
  → New at-risk deals this week: [Count]
  → Deals recovered from at-risk: [Count]
  → Deals lost that were flagged at-risk: [Count — model validation]
  → Deals lost that were NOT flagged at-risk: [Count — model gap analysis]

Manager/Rep Scorecard:
  → Rep name | Avg deal health | % healthy deals | At-risk recovery rate | Lost deals
  → Manager name | Team avg health | Deals requiring intervention | Pipeline coverage

Edge Cases

Integration Points