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Reference file

Planning calendar checklist

planning-calendar-checklist.md

Planning Calendar Checklist and Template

Master Template: 12-Week Planning Cycle

This template is for a calendar-year business (plan approved November, finalized December, in-market January). Adjust dates and phases for your fiscal year.

Phase 1: Data and Retrospective (Weeks 1-2)

Timing: First two weeks of August

Deliverables:

  • Prior-year close-out data compiled (actual revenue by segment, customer, rep)
  • Current-year variance analysis (forecast vs actual, by month through Month 7)
  • Customer retention and churn data (GRR, NRR, cohort-level churn)
  • Pipeline analysis from current state (coverage, velocity, stage distribution)
  • Market/competitive intelligence summary (new competitors, pricing changes, product launches)
  • Sales team feedback collected (top 3 challenges, top 3 opportunities)
  • Historical productivity data (quota attainment %, ramp curves, deal sizes by segment)

Owners: Finance (prior-year data), RevOps (pipeline and current-year variance), VP Sales (team feedback)

Gate: By end of Week 2, these datasets are shared in a central folder. No analysis needed yet; just data collection.

Phase 2: Bottoms-Up Build (Weeks 3-5)

Timing: Mid-August through early September

Week 3: Account Planning

  • New Business segment: Current booked opportunity pipeline reviewed; known deals for next 12 months marked
  • Expansion segment: Current expansion ARR baselined; customer cohorts assessed for expansion potential
  • Renewal segment: Current renewal contracts reviewed; at-risk renewals identified (NPS low, usage declining, budget cuts)
  • Each segment owner documents: "Here is what I see in my book of business. Here is what I expect to close next year."

Deliverables:

  • Account-level pipeline view (CRM export or strategic accounts list)
  • Named deals for next 12 months (with probabilities)
  • At-risk renewal list with mitigation plans
  • Expansion opportunities by customer cohort

Owner: VP Sales (New Business), VP CS (Expansion/Renewal)

Week 4: Capacity Model

  • Headcount plan locked: Current FTE + planned hires (with start dates)
  • Ramp curves applied: Each new hire's contribution modeled by month
  • Quota assignments verified: Is each rep's quota realistic based on prior productivity?
  • Productivity assumptions documented: Deal size, conversion rate, sales cycle, quota attainment %, utilization %
  • Capacity model calculated: FTE × Ramp factor × Quota = Base capacity

Deliverables:

  • Capacity model spreadsheet (or calculator)
  • Headcount plan with start dates
  • Ramp schedule per role
  • Quota assumptions by role and segment

Owner: RevOps (builds model), VP Sales (validates assumptions)

Week 5: Segment Totals and Bottoms-Up Rollup

  • New Business segment: Capacity model + pipeline overlay = forecast
  • Expansion segment: Current ARR × (GRR + growth) = forecast
  • Renewal segment: Current ARR × GRR - at-risk adjustments = forecast
  • Services/other segments: Capacity or historical run-rate = forecast
  • Total bottoms-up revenue plan = sum of segments
  • Confidence levels assigned per segment (HIGH / MEDIUM / LOW)
  • Key assumptions documented (retention %, expansion %, close rate %, ACV assumptions)

Deliverables:

  • Bottoms-Up Revenue Plan (summary table and detail)
  • Assumptions documentation (see planning-assumptions-template.md)
  • Segment-by-segment narrative (why each forecast is what it is)
  • Confidence scoring (HIGH segments: 90%+ confidence; MEDIUM: 70-90%; LOW: <70%)

Owner: VP Sales + VP CS (build), RevOps (consolidate), CFO (validate)

Gate: End of Week 5, bottoms-up plan is locked and shared with Finance.

Phase 3: Top-Down and Reconciliation (Weeks 6-8)

Timing: Mid-September through late September

Week 6: Finance Top-Down Model

  • Strategic revenue target determined (from board guidance, fundraising narrative, or company strategy)
  • Top-down drivers documented (market growth %, product launches, new GTM motions, churn assumptions)
  • Financial modeling of top-down target (headcount required, expense budget implications, cash impact)
  • Sensitivity analysis completed (what if growth is 15% vs 20%? What if product launch slips?)
  • Top-down plan shared with Revenue team for initial reaction

Deliverables:

  • Top-Down Revenue Plan (strategic target and drivers)
  • Financial implications model (headcount, expense, working capital)
  • Sensitivity analysis (3+ scenarios: downside / base / upside)
  • Comparison table: Bottoms-Up vs Top-Down (gap analysis)

Owner: CFO/Finance (builds model)

Week 7: Gap Analysis and Reconciliation Meetings

  • Gap quantified: "Bottoms-up is $7.8M. Top-down is $8.5M. Gap is $0.7M."
  • Scenario brainstorming: What specific actions close the gap? (Hiring, CS investment, ABM, pricing, churn reduction, etc.)
  • Scenario owners assigned: Each scenario has an explicit owner and assumptions
  • Scenarios ranked: Which are most likely? Which are required to hit plan? Which are aspirational?
  • Reconciliation meeting held (see reconciliation-playbook.md for detailed structure)
  • Outcomes documented: Plan of Record, scenario assignments, reforecast triggers

Deliverables:

  • Scenario matrix (scenario, owner, assumptions, upside, cost, timeline)
  • Reconciliation meeting notes
  • Draft Plan of Record (before final approval)
  • Stretch assignment document (who owns each stretch scenario?)

Owner: CFO + VP Sales + VP CS (joint meeting), RevOps (documents)

Week 8: Finalization and Executive Alignment

  • Plan of Record drafted and circulated to CFO and VP Sales
  • Any last-minute assumption challenges resolved
  • Board presentation narrative drafted (how do we explain the plan to board?)
  • Executive team alignment meeting (CEO, CFO, VP Sales sign-off)
  • Assumption sensitivity analysis completed (if top 3 assumptions miss, what is downside case?)

Deliverables:

  • Finalized Plan of Record (locked, ready for board)
  • Board presentation materials (1-2 slides: plan + drivers)
  • Executive alignment sign-off (email confirmation)
  • Risk / downside case documented (what could go wrong?)

Owner: CFO (leads finalization), CEO (alignment), RevOps (documents)

Gate: End of Week 8, Plan of Record is locked and ready for board approval.

Phase 4: Validation and Finalization (Weeks 9-10)

Timing: Early October

Week 9: Executive Alignment

  • SPICED assumptions validated: Does our ICP pipeline in CRM support the plan assumptions?
  • Scenario feasibility checked: If we commit to hiring 2 AEs, is recruiting plan solid? If we commit to ABM, is marketing team resourced?
  • Pipeline math validated: (Revenue target / pipeline coverage ratio) = required pipeline. Do we have it?
  • Financial impact modeled: What is cash impact of the plan? Working capital? Headcount investment?

Deliverables:

  • SPICED pipeline analysis (is pipeline qualified to support plan?)
  • Hiring plan confirmation (are we locked to hire dates?)
  • Investment plan (if plan requires new spend, is it approved?)
  • Cash flow impact (what is the P&L and balance-sheet impact?)

Owner: VP Sales (pipeline), VP People/HR (hiring), CFO (cash/P&L)

Week 10: Board Preparation

  • Board presentation slides completed (plan, drivers, risks, Q&A scenarios)
  • Board pre-calls held (CFO pre-briefs board members on any tricky topics)
  • FAQ document prepared (what questions will board ask? What are our answers?)
  • Downside scenarios documented (if we miss this assumption, here is the backup plan)

Deliverables:

  • Board presentation (slides and narrative)
  • Board pre-call talking points
  • FAQ with answers
  • Downside / contingency scenario (plan B if plan A does not work)

Owner: CEO (presents), CFO (materials prep), VP Sales (sales-specific narratives)

Gate: End of Week 10, board presentation is polished and ready.

Phase 5: Board Approval and Communication (Weeks 11-12)

Timing: Mid to late October

Week 11: Board Presentation

  • Board presentation delivered
  • Board approves Plan of Record
  • Board confirms any required investments (hiring, marketing spend, etc.)
  • Board confirms headcount / compensation approach for next year

Deliverables:

  • Board meeting notes
  • Board approval (formal sign-off on plan)
  • Any board conditions or follow-ups documented

Owner: CEO (presents), CFO (materials)

Week 12: Internal Communication and Implementation

  • Plan of Record communicated to all revenue teams
  • Segment-level targets shared (every rep/manager knows their target)
  • Scenario communication: What are we stretching on? (so teams understand and can execute)
  • Reforecast trigger communication: When will the plan change? (sets expectations)
  • Quarterly OKR planning begins (tie individual/team goals to the plan)
  • Compensation structures finalized (quotas locked for the year)
  • Operating cadence established (weekly forecast calls, monthly reviews, quarterly reforecasts)

Deliverables:

  • Internal plan communication (email + all-hands or team meetings)
  • Segment-level target cards (one per segment, one-pager explaining the target)
  • Scenario summary (what are we stretching on, and what it means for the team)
  • Reforecast trigger summary (when the plan might change)
  • Operating cadence calendar (lock forecast calls, reforecast windows, board reporting dates)

Owner: VP Sales (communication to sales teams), VP CS (communication to CS teams), RevOps (coordination)

Buffer: Post-Approval Implementation (Weeks 13+)

Weeks 13-16 (late October through early November):

  • Quarterly planning: First-quarter goals and OKRs set (aligned to annual plan)
  • Territory planning: Sales territories designed (if not already done)
  • Quota finalization: Individual rep quotas set (aligned to segment and territory targets)
  • Compensation communications: Reps understand how they are paid against the plan
  • Manager enablement: Sales managers trained on forecast discipline (how to run forecast calls, how to inspect deals)
  • Dashboard setup: Revenue dashboards built (tracking actual vs plan)
  • Forecast call training: Team trained on forecast categories (Commit, Best Case, Upside) and entry discipline

Fiscal Year Customization Guide

Use this guide to adjust the calendar for your specific fiscal year-end and board approval date.

Step 1: Lock Board Approval Date

Example: Fiscal Year April 1 start

  • Board approves plan: January (typically)
  • Plan effective date: April 1
  • Working backwards: Planning should conclude by end of February

Example: Fiscal Year July 1 start

  • Board approves plan: May (typically)
  • Plan effective date: July 1
  • Working backwards: Planning should conclude by end of April

Step 2: Build Backwards Timeline

From board approval date, work backwards:

Board approval (locked date):          January 15
Plan of Record finalization:           January 10 (5 days buffer)
Executive alignment:                   January 3 (1 week for alignment)
Reconciliation meeting:                December 15 (2 weeks for gap closure)
Finance top-down share:                December 8 (1 week for review)
Bottoms-up completion:                 December 1 (allow 1 week overlap)
Capacity model completion:             November 17 (2-3 weeks for capacity work)
Data gathering:                        October 20 (1 month for data)
Planning kickoff:                      October 13

Step 3: Set Phase Guardrails Per Your Calendar

Adjust phase lengths based on your business complexity:

Simple business ($5-15M ARR, 1 GTM motion, 1 product):

  • Phase 1 (Data): 1 week (not 2)
  • Phase 2 (Bottoms-Up): 2 weeks (not 3)
  • Phase 3 (Reconciliation): 2 weeks (not 3)
  • Phase 4 (Validation): 1 week
  • Phase 5 (Board): 1 week
  • Total: 7-8 weeks (compress the 12-week template)

Complex business ($50M+ ARR, multiple motions, multiple products, multiple verticals):

  • Phase 1 (Data): 3 weeks (complex data gathering)
  • Phase 2 (Bottoms-Up): 4 weeks (segment complexity)
  • Phase 3 (Reconciliation): 3 weeks (more scenarios, more debate)
  • Phase 4 (Validation): 2 weeks (detailed financial modeling)
  • Phase 5 (Board): 2 weeks (complex story to tell)
  • Total: 14-16 weeks (extend the template)

Phase Gate Checklist

Use this checklist to verify each phase is complete before moving to the next.

Phase 1 Gate (Ready for Bottoms-Up?)

  • Prior-year revenue data (actual, by segment and customer) is locked in a shared location
  • Current-year variance (forecast vs actual, by month) is analyzed and documented
  • Customer cohort data (retention, churn, expansion by cohort) is available
  • Current pipeline snapshot (CRM export with coverage ratio, velocity, by stage) is documented
  • Sales team feedback (top challenges, opportunities) is collected from all managers
  • Sign-off: VP Sales and CFO confirm: "Yes, we have what we need to build bottoms-up."

Phase 2 Gate (Ready for Finance Top-Down?)

  • Bottoms-up revenue forecast (by segment, with confidence levels) is locked
  • Capacity model (headcount, ramp, quota) is completed and validated
  • All assumptions are documented in a single source of truth (spreadsheet or shared doc)
  • Segment owners have sign-off on their numbers
  • Sign-off: VP Sales, VP CS, and RevOps confirm: "Bottoms-up is final; it is ready for reconciliation."

Phase 3 Gate (Ready for Board Approval?)

  • Top-down target and drivers are understood by Revenue team
  • Gap between bottoms-up and top-down is quantified
  • Scenarios are identified, owners assigned, and assumptions locked
  • Reconciliation meeting notes document the final plan
  • Plan of Record is drafted with scenarios clearly marked
  • Sign-off: CFO and VP Sales confirm: "Plan of Record is locked and ready for board."

Phase 4 Gate (Ready for Internal Launch?)

  • Board has approved the plan
  • Executive alignment meeting has confirmed feasibility of scenarios
  • Communication plan is drafted (what gets said to each audience)
  • Operating cadence is calendared (forecast calls, reforecast windows, board reporting dates)
  • Sign-off: CEO and CFO confirm: "Plan is approved. We are ready to communicate and execute."

Phase 5 Gate (Ready for Execution?)

  • All revenue teams (sales, CS, services) have received plan communication
  • Individual segment targets and quotas are set
  • Manager training on forecast discipline is complete
  • Revenue dashboards are built and live
  • Forecast processes (categories, entry, escalation) are trained
  • Sign-off: VP Sales, VP CS, and RevOps confirm: "Team is trained and ready to execute."

Common Planning Mistakes and Fixes

Mistake 1: Compressing Phase 2 (Bottoms-Up)

What happens: "We only have 1 week for bottoms-up, so let's just estimate."

  • Result: Bottoms-up is not grounded in reality; it is just a guess

Fix: Allocate 2-3 weeks to Phase 2. The time investment here prevents false precision later.

Mistake 2: Overlapping Phases (No Clear Handoff)

What happens: "Bottoms-up and finance top-down run in parallel; let's reconcile as we go."

  • Result: Confusion about which version is current; rework due to misalignment

Fix: Bottoms-up completes fully (end of Week 5). Finance top-down starts fresh (Week 6). Reconciliation happens once (Week 7).

Mistake 3: Extending Reconciliation Indefinitely

What happens: "We'll just keep tweaking scenarios until we get to the target."

  • Result: Plan is never locked; team does not know which number to execute

Fix: Reconciliation has a hard deadline (end of Week 7). If gap does not close, escalate to CEO for decision (not endless debate).

Mistake 4: Rushing Executive Alignment

What happens: "Plan of Record is locked; let's get board approval next week."

  • Result: Board has questions; plan gets re-opened; team loses confidence

Fix: Allocate 1 full week (Week 9) for executive alignment and sensitivity testing. Address board concerns before the board meeting.

Mistake 5: No Communication of Plan to the Team

What happens: "Plan is board-approved. That is enough."

  • Result: Reps do not know the target; they do not understand what they are accountable to

Fix: Invest 1 full week (Week 12) in segment-level communication. Every manager and rep should understand their target and why.

The 12-week runway is a house default, not a study result.