Queries · q183 · Head of B2B Commerce · week 1, night 4
“Does a bigger deal size correlate with a better or worse chance of closing, and does it drag out the cycle time?”
Fictional people at a fictional company, each played by a language-model agent. Who they are and what they are told
Week 1; shared with Samuel Whitcombe, Head of Merchant Success
B2B merchants say their sales teams struggle. How do their pipelines convert from lead to won deal, how long does it take, and what predicts winning or losing?
The manager, at the start of week 1
Note to Daniel Kim — B2B pipeline health
Daniel,
Samuel and I need to give the B2B wholesale merchants (and our own leadership) a clear-eyed view of why their sales teams are struggling to close business. This feeds a joint recommendation Samuel and I are making next week on where to invest — better pipeline coaching/tooling for merchants vs. changes to how we structure stages, quotes and terms in the product. So I want the picture to be accurate more than exhaustive — pick your battles across the nights you have.
Here's what I actually want to know, in plain terms:
Priority order is 1, 2, 3 first — those directly shape the recommendation. 4 and 5 are valuable but can slip if you run out of slots this week.
Keep each report to one clean question — I'd rather have four sharp answers than one crowded one. Flag anything that looks like a data quality issue rather than a real trend.
Thanks — looking forward to the Friday memo.
Patrick
Subject: A few questions from the Merchant Success side
Hi Daniel,
Good to see this getting attention this week. A few things I'd love your analysis to help answer, from the merchant-health angle:
Happy to compare notes before you finalize anything for Patrick.
Best, Samuel
The analyst · week 1, night 4, request 3 of 3
Night 3 take: two of three reports came back broken/empty, and I need my last night to fix the essential one and still land priority 5. The merchant-level report (Report 1) worked but had a clear bug: avg_amount_eur was NULL for 4 of 5 merchants (all the EUR ones) — almost certainly a failed EUR-to-EUR identity lookup in exchange_rates rather than a real data gap. The rep-level report (Report 2) came back with 0 rows because the engineer used an exact-match tenant filter (industry IN (...)) instead of the pattern that's worked all week, so it silently matched nothing — this is still an open, important gap (Patrick's Q4) and needs a clean re-run. The open-pipeline-age report (Report 3) also returned 0 rows, but I'm treating that as a real, confirmed finding rather than a bug: night 1's stage report already showed zero open opportunities at every New-business stage for every wholesale tenant, so there is genuinely no live open new-business pipeline in the warehouse right now — worth flagging to Patrick/Samuel as 'we can't assess forward-looking staleness risk because there's no open pipeline to look at; the only staleness signal we have is backward-looking (lost deals average ~35 days open vs ~9 for won).' Spending tonight's three slots on: (1) the corrected rep-level report with an explicit, unambiguous tenant-name filter, (2) a corrected merchant-level report with an explicit EUR-conversion fix, and (3) a deal-size-band breakdown to chase the odd avg-vs-median flip in the won/lost amount comparison, which gives a real answer to Patrick's optional #5 on deal size vs win rate. Payment terms (also part of #5) aren't captured anywhere in the B2B CRM/deals schema for the wholesaler's own customers, so I'm leaving that out of the memo as 'not measurable from current data' rather than forcing a weak proxy.
The engineer · 1 dry run on the empty schema, then the submission
WITH pipelines_filtered AS ( SELECT p.id AS pipeline_id, p.tenant_id FROM pipelines p JOIN tenants t ON t.id = p.tenant_id WHERE t.name IN ('Ballycorran Industrial Supply','Castell Fasteners','Hanse Industriebedarf','Midland Safety Wear','Polder Packaging') AND p.name = 'New business' ), opp AS ( SELECT o.id, o.is_won, o.created_at, o.closed_at, CASE WHEN o.currency_code = 'EUR' THEN o.amount ELSE o.amount / ( SELECT er.rate FROM exchange_rates er WHERE er.base_code = 'EUR' AND er.quote_code = o.currency_code AND er.as_of <= o.closed_at::date ORDER BY er.as_of DESC LIMIT 1 ) END AS amount_eur FROM opportunities o JOIN pipelines_filtered pf ON pf.pipeline_id = o.pipeline_id AND pf.tenant_id = o.tenant_id WHERE o.is_closed = true ), banded AS ( SELECT CASE WHEN amount_eur < 3000 THEN '<3000' WHEN amount_eur < 6000 THEN '3000-5999' WHEN amount_eur < 9000 THEN '6000-8999' WHEN amount_eur < 12000 THEN '9000-11999' ELSE '12000+' END AS amount_band_eur, CASE WHEN amount_eur < 3000 THEN 1 WHEN amount_eur < 6000 THEN 2 WHEN amount_eur < 9000 THEN 3 WHEN amount_eur < 12000 THEN 4 ELSE 5 END AS band_sort, is_won, closed_at, created_at FROM opp ) SELECT amount_band_eur, COUNT(*) AS opportunities_closed, COUNT(*) FILTER (WHERE is_won) AS closed_won, COUNT(*) FILTER (WHERE NOT is_won) AS closed_lost, ROUND(100.0 * COUNT(*) FILTER (WHERE is_won) / COUNT(*), 1) AS win_rate_pct, ROUND(AVG(EXTRACT(EPOCH FROM (closed_at - created_at)) / 86400.0)::numeric, 1) AS avg_days_open FROM banded GROUP BY amount_band_eur, band_sort ORDER BY band_sort
“Query compiles and returns the expected columns. Submitting.”
“Submitted. The report bands closed New-business opportunities (for the 5 named B2B tenants) by EUR-converted amount, showing opportunities closed, won/lost counts, win rate %, and average days-open per band — directly testing whether larger deals correlate with better or worse win rates and longer cycle times.”
As Daniel Kim saw it, from the small dataset the agents worked on
amount_band_eur | opportunities_closed | closed_won | closed_lost | win_rate_pct | avg_days_open ----------------+----------------------+------------+-------------+--------------+-------------- <3000 | 49 | 40 | 9 | 81.6 | 13.9 3000-5999 | 80 | 68 | 12 | 85.0 | 13.5 6000-8999 | 24 | 19 | 5 | 79.2 | 14.7 9000-11999 | 16 | 14 | 2 | 87.5 | 12.5 12000+ | 16 | 14 | 2 | 87.5 | 9.8 (5 rows)
The memo and the queries that followed; links found by title, so inferred
It builds on:
Changed only where the benchmark needs the same result on every system
WITH pipelines_filtered AS ( SELECT p.id AS pipeline_id, p.tenant_id SELECT p.id AS pipeline_id, p.tenant_id AS tenant_id FROM pipelines p JOIN tenants t ON t.id = p.tenant_id WHERE t.name IN ('Ballycorran Industrial Supply','Castell Fasteners','Hanse Industriebedarf','Midland Safety Wear','Polder Packaging') AND p.name = 'New business'),opp AS ( SELECT o.id, o.is_won, o.created_at, o.closed_at, o.id AS id, o.is_won AS is_won, o.created_at AS created_at, o.closed_at AS closed_at, CASE WHEN o.currency_code = 'EUR' THEN o.amount ELSE o.amount / ( SELECT er.rate FROM exchange_rates er WHERE er.base_code = 'EUR' AND er.quote_code = o.currency_code AND er.as_of <= o.closed_at::date ORDER BY er.as_of DESC LIMIT 1 AND er.as_of <= CAST(o.closed_at AS date) ORDER BY er.as_of DESC NULLS FIRST {{fetch_first(1)}} ) END AS amount_eur FROM opportunities o JOIN pipelines_filtered pf ON pf.pipeline_id = o.pipeline_id AND pf.tenant_id = o.tenant_id WHERE o.is_closed = true),banded AS ( SELECT CASE WHEN amount_eur < 3000 THEN '<3000' WHEN amount_eur < 6000 THEN '3000-5999' WHEN amount_eur < 9000 THEN '6000-8999' WHEN amount_eur < 12000 THEN '9000-11999' ELSE '12000+' END AS amount_band_eur, CASE WHEN amount_eur < 3000 THEN 1 WHEN amount_eur < 6000 THEN 2 WHEN amount_eur < 9000 THEN 3 WHEN amount_eur < 12000 THEN 4 ELSE 5 END AS band_sort, is_won, closed_at, created_at FROM opp)SELECT amount_band_eur, COUNT(*) AS opportunities_closed, COUNT(*) FILTER (WHERE is_won) AS closed_won, COUNT(*) FILTER (WHERE NOT is_won) AS closed_lost, ROUND(100.0 * COUNT(*) FILTER (WHERE is_won) / COUNT(*), 1) AS win_rate_pct, ROUND(AVG(EXTRACT(EPOCH FROM (closed_at - created_at)) / 86400.0)::numeric, 1) AS avg_days_open 100.0 * COUNT(*) FILTER (WHERE is_won) / COUNT(*) AS win_rate_pct, AVG({{seconds_between(created_at, closed_at)}} / 86400.0) AS avg_days_openFROM bandedGROUP BY amount_band_eur, band_sortORDER BY band_sortORDER BY band_sort NULLS LAST
WITH pipelines_filtered AS ( SELECT p.id AS pipeline_id, p.tenant_id AS tenant_id FROM pipelines p JOIN tenants t ON t.id = p.tenant_id WHERE t.name IN ('Ballycorran Industrial Supply','Castell Fasteners','Hanse Industriebedarf','Midland Safety Wear','Polder Packaging') AND p.name = 'New business' ), opp AS ( SELECT o.id AS id, o.is_won AS is_won, o.created_at AS created_at, o.closed_at AS closed_at, CASE WHEN o.currency_code = 'EUR' THEN o.amount ELSE o.amount / ( SELECT er.rate FROM exchange_rates er WHERE er.base_code = 'EUR' AND er.quote_code = o.currency_code AND er.as_of <= CAST(o.closed_at AS date) ORDER BY er.as_of DESC NULLS FIRST FETCH FIRST 1 ROWS ONLY ) END AS amount_eur FROM opportunities o JOIN pipelines_filtered pf ON pf.pipeline_id = o.pipeline_id AND pf.tenant_id = o.tenant_id WHERE o.is_closed = true ), banded AS ( SELECT CASE WHEN amount_eur < 3000 THEN '<3000' WHEN amount_eur < 6000 THEN '3000-5999' WHEN amount_eur < 9000 THEN '6000-8999' WHEN amount_eur < 12000 THEN '9000-11999' ELSE '12000+' END AS amount_band_eur, CASE WHEN amount_eur < 3000 THEN 1 WHEN amount_eur < 6000 THEN 2 WHEN amount_eur < 9000 THEN 3 WHEN amount_eur < 12000 THEN 4 ELSE 5 END AS band_sort, is_won, closed_at, created_at FROM opp ) SELECT amount_band_eur, COUNT(*) AS opportunities_closed, COUNT(*) FILTER (WHERE is_won) AS closed_won, COUNT(*) FILTER (WHERE NOT is_won) AS closed_lost, 100.0 * COUNT(*) FILTER (WHERE is_won) / COUNT(*) AS win_rate_pct, AVG(CAST(EXTRACT(EPOCH FROM (closed_at - created_at)) AS NUMERIC(18,6)) / 86400.0) AS avg_days_open FROM banded GROUP BY amount_band_eur, band_sort ORDER BY band_sort NULLS LAST
WITH pipelines_filtered AS ( SELECT p.id AS pipeline_id, p.tenant_id AS tenant_id FROM pipelines p JOIN tenants t ON t.id = p.tenant_id WHERE t.name IN ('Ballycorran Industrial Supply','Castell Fasteners','Hanse Industriebedarf','Midland Safety Wear','Polder Packaging') AND p.name = 'New business' ), opp AS ( SELECT o.id AS id, o.is_won AS is_won, o.created_at AS created_at, o.closed_at AS closed_at, CASE WHEN o.currency_code = 'EUR' THEN o.amount ELSE o.amount / ( SELECT er.rate FROM exchange_rates er WHERE er.base_code = 'EUR' AND er.quote_code = o.currency_code AND er.as_of <= CAST(o.closed_at AS date) ORDER BY er.as_of DESC NULLS FIRST LIMIT 1 ) END AS amount_eur FROM opportunities o JOIN pipelines_filtered pf ON pf.pipeline_id = o.pipeline_id AND pf.tenant_id = o.tenant_id WHERE o.is_closed = true ), banded AS ( SELECT CASE WHEN amount_eur < 3000 THEN '<3000' WHEN amount_eur < 6000 THEN '3000-5999' WHEN amount_eur < 9000 THEN '6000-8999' WHEN amount_eur < 12000 THEN '9000-11999' ELSE '12000+' END AS amount_band_eur, CASE WHEN amount_eur < 3000 THEN 1 WHEN amount_eur < 6000 THEN 2 WHEN amount_eur < 9000 THEN 3 WHEN amount_eur < 12000 THEN 4 ELSE 5 END AS band_sort, is_won, closed_at, created_at FROM opp ) SELECT amount_band_eur, COUNT(*) AS opportunities_closed, COUNT(*) FILTER (WHERE is_won) AS closed_won, COUNT(*) FILTER (WHERE NOT is_won) AS closed_lost, 100.0 * COUNT(*) FILTER (WHERE is_won) / COUNT(*) AS win_rate_pct, AVG(CAST(EXTRACT(EPOCH FROM (closed_at - created_at)) AS NUMERIC(18,6)) / 86400.0) AS avg_days_open FROM banded GROUP BY amount_band_eur, band_sort ORDER BY band_sort NULLS LAST
WITH pipelines_filtered AS ( SELECT p.id AS pipeline_id, p.tenant_id AS tenant_id FROM pipelines p JOIN tenants t ON t.id = p.tenant_id WHERE t.name IN ('Ballycorran Industrial Supply','Castell Fasteners','Hanse Industriebedarf','Midland Safety Wear','Polder Packaging') AND p.name = 'New business' ), opp AS ( SELECT o.id AS id, o.is_won AS is_won, o.created_at AS created_at, o.closed_at AS closed_at, CASE WHEN o.currency_code = 'EUR' THEN o.amount ELSE o.amount / ( SELECT er.rate FROM exchange_rates er WHERE er.base_code = 'EUR' AND er.quote_code = o.currency_code AND er.as_of <= CAST(o.closed_at AS date) ORDER BY er.as_of DESC NULLS FIRST FETCH FIRST 1 ROWS ONLY ) END AS amount_eur FROM opportunities o JOIN pipelines_filtered pf ON pf.pipeline_id = o.pipeline_id AND pf.tenant_id = o.tenant_id WHERE o.is_closed = true ), banded AS ( SELECT CASE WHEN amount_eur < 3000 THEN '<3000' WHEN amount_eur < 6000 THEN '3000-5999' WHEN amount_eur < 9000 THEN '6000-8999' WHEN amount_eur < 12000 THEN '9000-11999' ELSE '12000+' END AS amount_band_eur, CASE WHEN amount_eur < 3000 THEN 1 WHEN amount_eur < 6000 THEN 2 WHEN amount_eur < 9000 THEN 3 WHEN amount_eur < 12000 THEN 4 ELSE 5 END AS band_sort, is_won, closed_at, created_at FROM opp ) SELECT amount_band_eur, COUNT(*) AS opportunities_closed, COUNT(*) FILTER (WHERE is_won) AS closed_won, COUNT(*) FILTER (WHERE NOT is_won) AS closed_lost, 100.0 * COUNT(*) FILTER (WHERE is_won) / COUNT(*) AS win_rate_pct, AVG(CAST(divideDecimal(toDecimal128(dateDiff('microsecond', created_at, closed_at), 0), toDecimal128(1000000, 0), 6) AS Nullable(Decimal(18, 6))) / 86400.0) AS avg_days_open FROM banded GROUP BY amount_band_eur, band_sort ORDER BY band_sort NULLS LAST
The agents' own records, as the role play wrote them; only the personal data of the person who ran it is redacted
Report request from Daniel Kim (analyst for the Head of B2B Commerce):
Title: B2B Wholesale: Win Rate and Cycle Time by Deal-Size Band (New Business)
Question: Does a bigger deal size correlate with a better or worse chance of closing, and does it drag out the cycle time?
Grain: one row per deal-size band (based on EUR-converted opportunity amount)
Columns:
- amount_band_eur
- opportunities_closed
- closed_won
- closed_lost
- win_rate_pct
- avg_days_open
Details: Prompted by an odd pattern in an earlier won-vs-lost comparison: lost New-business opportunities had a LOWER average amount (5628.59 EUR) than won ones (7097.90 EUR), but a HIGHER median amount (6520.14 vs 5880.52 EUR) — suggesting the amount distribution isn't simply 'bigger deals win more' and deserves a direct bucket breakdown rather than just an average. Filter: tenants.name IN ('Ballycorran Industrial Supply','Castell Fasteners','Hanse Industriebedarf','Midland Safety Wear','Polder Packaging'), pipeline_id = each tenant's 'New business' pipeline, is_closed = true. Convert amount to EUR per opportunity: if currency_code = 'EUR', amount_eur = amount; otherwise amount_eur = amount / rate from exchange_rates (base_code='EUR', quote_code=currency_code, as_of nearest date on or before closed_at). Bucket amount_eur into: '<3000', '3000-5999', '6000-8999', '9000-11999', '12000+'. For each band: count of opportunities closed, closed won, closed lost, win_rate_pct, and avg_days_open (avg of closed_at - created_at in days). Order by band ascending (by lower bound).
Check your query with the warehouse's dry_run tool, then hand it in with submit.dry_runWITH pipelines_filtered AS ( SELECT p.id AS pipeline_id, p.tenant_id FROM pipelines p JOIN tenants t ON t.id = p.tenant_id WHERE t.name IN ('Ballycorran Industrial Supply','Castell Fasteners','Hanse Industriebedarf','Midland Safety Wear','Polder Packaging') AND p.name = 'New business' ), opp AS ( SELECT o.id, o.is_won, o.created_at, o.closed_at, CASE WHEN o.currency_code = 'EUR' THEN o.amount ELSE o.amount / ( SELECT er.rate FROM exchange_rates er WHERE er.base_code = 'EUR' AND er.quote_code = o.currency_code AND er.as_of <= o.closed_at::date ORDER BY er.as_of DESC LIMIT 1 ) END AS amount_eur FROM opportunities o JOIN pipelines_filtered pf ON pf.pipeline_id = o.pipeline_id AND pf.tenant_id = o.tenant_id WHERE o.is_closed = true ), banded AS ( SELECT CASE WHEN amount_eur < 3000 THEN '<3000' WHEN amount_eur < 6000 THEN '3000-5999' WHEN amount_eur < 9000 THEN '6000-8999' WHEN amount_eur < 12000 THEN '9000-11999' ELSE '12000+' END AS amount_band_eur, CASE WHEN amount_eur < 3000 THEN 1 WHEN amount_eur < 6000 THEN 2 WHEN amount_eur < 9000 THEN 3 WHEN amount_eur < 12000 THEN 4 ELSE 5 END AS band_sort, is_won, closed_at, created_at FROM opp ) SELECT amount_band_eur, COUNT(*) AS opportunities_closed, COUNT(*) FILTER (WHERE is_won) AS closed_won, COUNT(*) FILTER (WHERE NOT is_won) AS closed_lost, ROUND(100.0 * COUNT(*) FILTER (WHERE is_won) / COUNT(*), 1) AS win_rate_pct, ROUND(AVG(EXTRACT(EPOCH FROM (closed_at - created_at)) / 86400.0)::numeric, 1) AS avg_days_open FROM banded GROUP BY amount_band_eur, band_sort ORDER BY band_sort
STATUS: COMPILES (dry run on the empty schema, no data read) COLUMNS: amount_band_eur, opportunities_closed, closed_won, closed_lost, win_rate_pct, avg_days_open
submitWITH pipelines_filtered AS ( SELECT p.id AS pipeline_id, p.tenant_id FROM pipelines p JOIN tenants t ON t.id = p.tenant_id WHERE t.name IN ('Ballycorran Industrial Supply','Castell Fasteners','Hanse Industriebedarf','Midland Safety Wear','Polder Packaging') AND p.name = 'New business' ), opp AS ( SELECT o.id, o.is_won, o.created_at, o.closed_at, CASE WHEN o.currency_code = 'EUR' THEN o.amount ELSE o.amount / ( SELECT er.rate FROM exchange_rates er WHERE er.base_code = 'EUR' AND er.quote_code = o.currency_code AND er.as_of <= o.closed_at::date ORDER BY er.as_of DESC LIMIT 1 ) END AS amount_eur FROM opportunities o JOIN pipelines_filtered pf ON pf.pipeline_id = o.pipeline_id AND pf.tenant_id = o.tenant_id WHERE o.is_closed = true ), banded AS ( SELECT CASE WHEN amount_eur < 3000 THEN '<3000' WHEN amount_eur < 6000 THEN '3000-5999' WHEN amount_eur < 9000 THEN '6000-8999' WHEN amount_eur < 12000 THEN '9000-11999' ELSE '12000+' END AS amount_band_eur, CASE WHEN amount_eur < 3000 THEN 1 WHEN amount_eur < 6000 THEN 2 WHEN amount_eur < 9000 THEN 3 WHEN amount_eur < 12000 THEN 4 ELSE 5 END AS band_sort, is_won, closed_at, created_at FROM opp ) SELECT amount_band_eur, COUNT(*) AS opportunities_closed, COUNT(*) FILTER (WHERE is_won) AS closed_won, COUNT(*) FILTER (WHERE NOT is_won) AS closed_lost, ROUND(100.0 * COUNT(*) FILTER (WHERE is_won) / COUNT(*), 1) AS win_rate_pct, ROUND(AVG(EXTRACT(EPOCH FROM (closed_at - created_at)) / 86400.0)::numeric, 1) AS avg_days_open FROM banded GROUP BY amount_band_eur, band_sort ORDER BY band_sort
Submitted to tonight's batch. Your work on this request is done.