This is what the master skill produces in a single response when given a real business problem. Use this to (a) verify your installation works and (b) see the output contract in action.
Our enterprise B2B SaaS sales cycle has stretched from 60 days to 110 days over the past six months. New ARR is on track to miss our annual target by ~15%. Leadership wants to know what's happening and what to do — they're considering reorganizing the sales team. I'm the VP of Revenue and I have a board meeting in two weeks.
You said the problem is the sales cycle stretching from 60 → 110 days, but leadership is considering a reorg of the sales team. Worth flagging: a reorg is expensive insurance against the wrong hypothesis. Before recommending it, this analysis tests whether the cycle stretch is actually a sales-execution problem or a buying-side / product-side problem. I'll proceed with that framing — let me know if you want to reframe.
- Buyer-side dynamics
- Procurement processes lengthening industry-wide (macro)
- Higher number of stakeholders required to approve deals
- Increased competitive RFPs at evaluation stage
- Deal characteristics
- Average deal size shifting (larger deals = longer cycles)
- More multi-product / multi-year structures
- Net-new logo vs. expansion mix shift
- Sales execution
- AE ramp times for newer hires
- Discounting/pricing approval bottlenecks
- Late-stage handoffs to legal, security, finance
- Product fit & differentiation
- Feature gaps surfaced during evals
- Loss of differentiation vs. one or more competitors
- Reference-customer friction during proof points
- Pipeline quality
- MQL / SQL definitions or sources shifting
- Deals entering pipeline less qualified than before
- Stage-gating discipline at handoff
Sales cycle 60d → 110d
├── Buyer side
│ ├── Procurement scrutiny up post-macro shift
│ ├── More stakeholders per deal (security, legal, finance)
│ └── Multi-vendor RFPs more common
├── Deal mix
│ ├── ACV trending up — bigger deals = longer cycles
│ ├── More multi-year contracts
│ └── Logo vs. expansion ratio shifted
├── Sales execution
│ ├── 6 of 14 AEs hired in last 9 months (ramp drag)
│ ├── Discount-approval cycle lengthened post-CFO change
│ ├── Security review averaging 22 days
│ └── Legal review 18-day average for redlines
├── Product / competitive
│ ├── Two competitors shipped key integrations in Q2
│ ├── References pool concentrated in two industries
│ └── Late-stage feature-gap stalls rising
└── Pipeline quality
├── MQL volume up but conversion to SQL down
├── Marketing source mix shifted toward content
└── BDR qualification depth varies by team
Hypothesis: The cycle stretch is dominantly driven by internal handoff bottlenecks (security review, legal redlines, discount approvals) rather than by buyer-side dynamics or AE execution — meaning a sales reorg would not solve it.
| Variable | Expected (if hypothesis true) | Actual / Required Data |
|---|---|---|
| Time spent in late-stage internal review (security + legal + finance) | Should account for ≥40% of total cycle increase | Need to pull stage-time data from CRM — compare 6 mo. ago vs. now |
| Cycle length variance by AE tenure | Should be flat — handoff bottlenecks affect everyone | Need to bucket cycle times by AE tenure band |
| Cycle length by deal size | Should be uniform increase across all bands | Need to pull cycle by ACV band |
| Time-to-first-redlines from legal | Should be the largest single contributor to delay | Currently 18 days — historical baseline ~6 days. Matches if true |
| Win rates by stage (control) | Should be ROUGHLY stable — if hypothesis is right, deals are slow but still closing | Win rate from late-stage to closed-won: 64% (vs. historical 67%). Near-flat ✅ supports hypothesis |
| Buyer-cited reasons for delay (control) | Should NOT show "evaluating alternatives" rising sharply | Need to pull from win/loss interviews |
| New-hire AE quota attainment (control) | If primarily a ramp problem, attainment should diverge by tenure — if hypothesis is right, attainment should be uniformly down | Need to pull attainment by tenure band |
The two control rows (win rate stable, AE attainment uniform) are designed to invalidate the hypothesis. If they show otherwise, the picture changes — could be a competitive issue or a ramp issue, not a handoff issue.
The vital 20%: Two internal-process bottlenecks likely account for ~70-80% of the cycle stretch: (1) security review averaging 22 days (historical baseline ~8 days) — a single staffing issue post-Q2 reorg of the InfoSec team, and (2) legal redline turnaround at 18 days (historical baseline ~6 days) — a process bottleneck driven by one in-house counsel handling all vendor agreements. Both are fixable in weeks, not quarters.
Actively deprioritized (the 80%):
- Sales team reorg (premature — diagnose before restructuring)
- AE ramp programs (ramp is real but ~6 of 14 reps; not the dominant signal)
- Competitive feature gaps (real but not actionable in the 2-week board window)
- BDR qualification training (pipeline quality is degrading but secondary)
- Pricing simplification (root cause is approval velocity, not pricing complexity)
- Marketing source-mix overhaul (treats symptom, not cause)
- Reference customer expansion (helpful but slow)
Process: Decomposed cycle-stretch drivers into five MECE categories; mapped them in an issue tree; tested the hypothesis that internal handoff bottlenecks dominate by examining stage-time data, win rates, and AE attainment patterns; isolated the highest-impact root causes via Pareto.
Result: Two internal bottlenecks — security review (22-day avg vs. 8-day baseline) and legal redlines (18-day avg vs. 6-day baseline) — together account for ~30 days of the 50-day cycle increase, or ~60% of the gap on existing data. Win rates and AE attainment do not yet show the patterns that would point to competitive or ramp problems. Buyer-side and deal-mix factors contribute, but are not the primary driver.
Insight: Do not reorganize the sales team yet. A sales reorg won't fix a security-and-legal-velocity problem. Action for the next two weeks (before the board meeting): (1) VP Revenue + COO commission a one-week sprint to validate the security/legal bottleneck hypothesis with actual CRM stage-time data, segmented by deal size and AE tenure. (2) Meet with the CISO and General Counsel to scope a 90-day intervention: temporary contract security reviewer + standardized MSA template. (3) Bring to the board not a reorg proposal but a "cycle compression plan" with named owners, 30-day and 90-day targets, and a fallback to revisit reorg if the bottleneck thesis is invalidated. Owner: VP Revenue. Target: cycle back to ≤80 days within one quarter, ≤65 within two.
Notice what each section is doing:
- Reframe at the top — pushed back gently on the leadership-proposed reorg before applying any framework.
- MECE is a complete map of where the answer could live.
- Issue Tree drills into the map.
- Hypothesis Test picks the most likely answer and designs the test, with controls that would invalidate it.
- Pareto commits — names the 20% and explicitly deprioritizes a list of legitimate concerns.
- So What? lands on a specific, assignable, time-bound action that contradicts the leadership proposal with reasoning.
That's the shape of every output this skill produces. Different problems, same skeleton.