Hindsight understands every opportunity, learns from comparable wins and losses, and proactively guides reps on what to do next.
Enterprise GTM playbook
Validation Stage
Based on 38 won deals in 2026
Turn patterns across wins and losses into guidance on who to target, how to position, and which questions to ask.
Build from deal experience
Winnable: Northstar Health $180K
Technical validation has stalled. The implementation owner hasn’t joined the evaluation.
Play: Invite the IT owner to a migration-planning session and share the rollout plan before the proposal.
Use live deal signals to deliver guidance when an opportunity stalls, a competitor appears, or a key stakeholder is missing.
Activate the right Play# product-insightsEvery MondayWeekly Product Win-Loss
Native integration gaps are blocking strong-fit deals.
$420K ARR across 3 lost deals
“We need a native connector before we can commit.”
Example opportunities · Closed lost
Deliver recurring insights on win-loss drivers, competitive trends, product gaps, and pipeline risks—with deal evidence your team can act on.
Get recurring insightsCRM fields tell part of the story. Calls, emails, and buyer feedback fill in the rest—and sometimes disagree.
Hindsight’s win-loss analysis turns scattered information into a single view of why you won, why you lost, and what to do differently.
Explore win-loss analysisNorthstar Health
Closed lostEnterprise platform · $180K ARR
Deal Review
The multi-site buyer matched our ICP, but a missing NetSuite connector blocked finance approval. Sales never brought IT into the migration plan.
Multi-site healthcare team with an active finance sponsor.
1: Outside target profile · 3: Partial fit · 5: Target segment, buyer, and use case all align.
IT owner wasn’t engaged; migration concerns stayed unresolved.
1: Key buying steps missed · 3: Some gaps · 5: Stakeholders aligned, risks addressed, and next steps agreed.
Core workflows fit; the required NetSuite connector was missing.
1: Core needs unmet · 3: Core fit with material gaps · 5: All critical requirements supported.
Key decision drivers
Integration gapCritical
Finance required a native NetSuite connector in three calls.
Migration riskMedium
IT’s historical-data migration concerns had no agreed rollout plan.
Playbooks
Hindsight turns your deal history into a complete GTM playbook—from who to target to how to win—with evidence behind every claim.
Review suggested updates as new deals unfold. Put approved guidance to work through Plays, Markdown, or MCP.
Explore PlaybooksWho we win with
Why they buy
Discovery
Positioning
Objection handling
Implementation
Have the buyer describe one hero workflow and its business impact in their own words. Build the demo around that workflow.
Evidence
Reached demo
85% with a buyer-defined workflow + business impact (51/60)
45% without (18/40)
+40-point lift in demo progression
Example dataset · 100 enterprise deals entering discovery, Jan–Jun 2026. Demo progression measured within 90 days.
Suggested update for your team to review
Add “Walk me through one workflow you’d change. What would that mean for your business?” to discovery.
Hindsight combines live pipeline signals, your published playbook, and experience from comparable deals to deliver specific guidance where reps work.
Build a call plan from the buyer’s priorities and similar wins.
TRIGGER
2 hours before a demoWinnable: Northstar Health $180K
Demo is in two hours. Security and implementation are the buyer’s open questions.
Play: Lead with the managed rollout plan and bring the security lead into the call.
Enterprise GTM playbook
Demos
Win rateGive the rep the positioning and proof that worked in comparable deals.
TRIGGER
Competitor tagged in dealWinnable: Vantage Labs $128K
The incumbent surfaced during technical validation.
Play: Use the migration proof point that won 4 similar evaluations. Send it before renewal review.
Enterprise GTM playbook
Competitive positioning
Competitive positioning scoreIdentify the missing action or stakeholder based on deals that recovered.
TRIGGER
Stalled dealWinnable: Meridian Health $240K
No activity for 12 days. Comparable wins involved IT earlier.
Play: Invite the IT owner to a migration-planning session this week.
Stalled-deal recovery deck
Deals reach proposalInsights
Focus on the product, segment, team, or deals that matter to you. Hindsight delivers recurring reports on your schedule, straight to the Slack channel where your team works.
Explore dashboards or ask Hindsight’s AI agent follow-up questions whenever you need to go deeper.
Explore Insights# product-insightsEvery MondayWeekly Product Win-Loss
Native integration gaps are blocking strong-fit deals.
$420K ARR across 3 lost deals
Buyers needed a native accounting connector before moving forward. Integration confidence outweighed otherwise strong product fit.
“We need a native connector before we can commit.”
Example opportunities · Closed lost
Get a weekly digest of the features driving wins and gaps costing deals for your product, with buyer quotes and feedback ranked by revenue impact.
Get a monthly win-loss report for your segment or product line, with win rates, competitive outcomes, and the reasons buyers choose you or walk away.
Get recurring deep dives for your team or individual reps, highlighting stalled deals, pipeline risks, and coaching opportunities to guide team reviews.
You can hear it in their voice on calls. They’re more confident talking about competitors.
+10points
New-business win rate
Simpro reported a 10-percentage-point increase in Q4 compared with the prior nine months.
Bring together CRM activity, calls, emails, documents, and buyer feedback. Deliver insights and guidance through Hindsight, Slack, and your connected workflows.
Use Hindsight end to end, or bring its deal understanding and published playbooks into your own agents through API and MCP.
View integrationsYour deal evidence
Reliable deal understanding
Insights · Playbooks · Plays
API + MCPWhere your team works
Explore how Hindsight turns deal evidence into a useful report, an actionable playbook, and guidance for a live opportunity.