evals/evals.json
{
"skill_name": "sales-org-structure",
"evals": [
{
"id": 1,
"prompt": "I run sales at Tallowfield, we sell a shift-scheduling tool to independent pharmacies. ACV is about $2,900 a year and we've got 7 full-cycle AEs. I did a calendar audit last month: they're each burning around 7 hours a week on their own prospecting and only about 24% of their week is actual selling. Their calendars have big holes in them. Board meeting is in two weeks and I want to walk in with a plan to hire 4 SDRs in Q1 so the AEs can just close. How should I lay that out?",
"expected_output": "A design that confirms the workload triggers fired, then refuses the SDR split because the $2,900 ACV sits below the funding floor for a dedicated prospecting role, proposes an alternative move or no move, and writes the condition that would unblock SDRs later.",
"files": [],
"expectations": [
"Confirms both SDR-split triggers fired using the stated figures: self-prospecting above roughly 4 hours per week (7 stated) and selling time below roughly 30% of the week (24% stated).",
"Names an ACV floor of roughly $4,000 below which a dedicated prospecting role cannot be funded, and applies the stated $2,900 ACV against it.",
"States the SDR split is blocked and deleted this cycle despite the fired workload triggers, rather than recommended in a reduced or phased form.",
"Does not recommend hiring 4 SDRs, or any SDR headcount, for Q1.",
"Attributes the ACV floor to Aaron Ross / Predictable Revenue's own caveat rather than presenting it as generic advice.",
"Checks AE calendar fullness as a separate independent blocker and notes it does not apply here, since the calendars have gaps.",
"Does not derive or quote an SDR:AE ratio for the move it refuses.",
"Proposes at least one alternative from the structural-move menu, or explicitly recommends no move, rather than leaving the AE workload unaddressed.",
"Names the behavioral trigger behind whatever move it does propose.",
"States the condition that would unblock the SDR split later, such as ACV rising above roughly $4K or a pricing/motion change, as a written future trigger.",
"Produces no job requisition, interview loop, or hiring scorecard for SDR seats.",
"Does not treat the board meeting date as a reason to make a structural move."
]
},
{
"id": 2,
"prompt": "Nordvale Systems, $14M ARR, we sell compliance software to regional banks. 9 AEs, ACV around $30K, deals take about 4 months. I'm budgeting SDR headcount for next year and the numbers I keep finding contradict each other: one report says 1 SDR for every 2 AEs, another says the median is 0.8 SDRs per AE. Which one do I plan against? For context, each AE needs roughly 5 new qualified opportunities a month to stay on quota, marketing and inbound already generate about 60% of those today, and the SDRs I've seen at companies our size seem to produce around 6 qualified opportunities a month each.",
"expected_output": "A ratio derived backward from the company's own funnel math to roughly 3 SDRs (about 1:3), with the published bands used only as a sanity check and the conflict between published headline figures explained by definitional distortions.",
"files": [],
"expectations": [
"Derives the SDR headcount from the company's own funnel math rather than adopting either published ratio.",
"Computes the total monthly opportunity need as 45, from 9 AEs times 5 opportunities per month.",
"Subtracts the roughly 60% inbound and marketing-sourced share, leaving about 18 opportunities per month for SDRs to source.",
"Divides the remainder by roughly 6 qualified opportunities per SDR per month, arriving at about 3 SDRs.",
"States the resulting ratio as roughly 1:3, three SDRs to nine AEs.",
"Uses the published bands only as a sanity check and labels them as such.",
"Names a band rather than a single headline figure, for example 1:2 to 1:2.5 for mixed SaaS or 1:3 to 1:4 for enterprise inbound.",
"Explains that the two conflicting published figures are both honestly published rather than one of them being wrong.",
"Names at least three distortion factors behind the conflict from: segment mix, inconsistent SDR/BDR labeling, hybrid self-prospecting AEs, uncounted offshore capacity, AI SDR tooling.",
"Writes down the ratio's assumptions, including inbound share, opportunities per SDR, and role definitions, as explicit inputs.",
"States that the inbound share, not a published headline, is what moves the answer, for example noting that near-zero inbound would yield a materially richer ratio.",
"Requires an explicit decision on whether hybrid AEs, offshore capacity, and AI SDR tooling count in the denominator before comparing against any benchmark.",
"Presents the longitudinal drift, roughly 1 SDR per 3.9 AEs in 2014 down to about 1:2.4 in 2025, as directional context rather than the number to adopt."
]
},
{
"id": 3,
"prompt": "Brightloom Analytics here, $11M ARR. 9 AEs, each of them keeps their accounts after close. Expansion is now 38% of our new revenue and I don't think anyone's really working it, the AEs chase new logos because that's what pays. I want hunters and farmers split before our fiscal year starts, which is 5 weeks out. Fair warning: I have close to zero appetite for touching accounts or comp right now, we changed commission last spring and lost two reps over it. What's the plan?",
"expected_output": "A refusal of the hunter/farmer split at 9 AEs, with the account reassignment struck from this cycle rather than shrunk, the mechanism of the failure explained, and the future trigger written down.",
"files": [],
"expectations": [
"Declines the hunter/farmer split now, naming roughly 25 AEs as the threshold and 9 as well below it.",
"Attributes the roughly 25-AE floor to practitioner guidance such as Jason Lemkin or Brett Queener rather than presenting it as an invented rule of thumb.",
"Explains the specific failure mechanism: below that size quota-credit rules distort behavior, and reps slow-roll expansion to stay inside their credited window.",
"States the account reassignment is deleted this cycle rather than demoted or scaled down, given the stated lack of political capital.",
"Gives the reason deletion beats demotion: a half-executed reassignment leaves two reps claiming one account, which is worse than no split.",
"Names explicitly what was struck from the plan and why.",
"Treats the 5-week fiscal-year deadline as a constraint that rules out a full rebuild, favoring at most a single move.",
"Does not propose segment pods.",
"Mentions the hunter's credited-tail cap, commonly 12 months, only as the mechanic that would apply if and when the split later fires.",
"Routes comp mechanics such as base-heavy farmer pay to a compensation-design skill rather than designing the plan here.",
"Writes the future trigger that would fire the split, roughly 25 AEs plus material expansion revenue, instead of only declining.",
"Does not treat 38% expansion revenue on its own as sufficient justification for the split."
]
},
{
"id": 4,
"prompt": "Kestrel Freight Software. 31 reps total, SDRs feeding AEs feeding a CS team, and it's been working fine for mid-market where deals close in about 6 weeks. Problem is the enterprise tier we launched last year: 6 to 12 month cycles, we counted 14 different stakeholders on the last one, and we're losing all of them because we're running them through the same funnel. My plan is to break the whole org into three pods of ten and let each one own its own book. Sanity-check me?",
"expected_output": "A hybrid design that stands up one enterprise pod while leaving the mid-market assembly line untouched, with the pod's costs accepted deliberately and the whole-org conversion rejected.",
"files": [],
"expectations": [
"Confirms the pod trigger has fired for the enterprise segment: roughly 20+ reps plus multi-segment complexity, with a buying committee in the 11-20+ stakeholder range (14 stated).",
"Leaves the mid-market assembly line structurally unchanged and says so explicitly.",
"Rejects converting all 31 reps into three pods.",
"Gives the reason the mid-market conversion is wrong: no trigger fired there, and it would forfeit working stage-conversion visibility for pure overhead.",
"Proposes a hybrid, assembly line for the volume segment plus one pod for enterprise, and names hybrid as where mature orgs land rather than a temporary way-station.",
"Specifies pod composition concretely, for example roughly 3 SDR + 2 AE + 1 CS owning a named book of enterprise accounts.",
"Attributes the pod model to Jacco van der Kooij / Winning By Design.",
"States the pod's accepted costs: duplicated management overhead, and individual contribution harder to isolate with weak performers shielded by the team.",
"Mitigates those costs with per-role metrics inside the pod rather than abandoning the shape.",
"Places pods as the highest-value and highest-effort move, losing on efficiency ranking yet promoted because no cheaper move restores conversion accountability once the trigger fires.",
"Does not justify pods on seniority, modernity, or cross-functional fashion.",
"Names what was deliberately left unchanged as part of the design output."
]
},
{
"id": 5,
"prompt": "Aviron Health, we just closed a Series B and the board wants to see a 'scaled' sales org by the next meeting. Today: 11 AEs under 2 frontline managers, 4 SDRs under an SDR lead, single SMB segment, ACV about $18K. The team is honestly doing fine, AEs spend maybe 2 hours a week prospecting for themselves, roughly 46% of their week is selling, and their calendars are packed with qualified meetings. I need a full redesign to present in three weeks. What structure should we move to?",
"expected_output": "A finding that no trigger has fired, so the current structure is the correct design, plus the written next-stage triggers instead of a reorg.",
"files": [],
"expectations": [
"States that no behavioral trigger has fired and the correct design is the current structure.",
"Checks each stated signal against its threshold: 2 hours per week self-prospecting against the roughly 4-hour trigger, 46% selling time against the roughly 30% floor, and full calendars.",
"Names full calendars as an explicit blocker on adding SDRs, since SDRs are added only once AEs show empty-calendar syndrome.",
"Declines to recommend a restructure tied to the funding round or the board meeting.",
"Names restructuring on the calendar or on a fundraise, with no fired trigger, as a failure mode that spends reversibility for nothing.",
"Confirms current spans, roughly 5-6 reps per frontline manager and 4 SDRs per SDR lead, sit within or below the 6-10 band, so no manager hire is triggered.",
"Does not propose segment pods, noting rep count below the roughly 20+ trigger and a single homogeneous segment.",
"Does not propose a hunter/farmer split, noting headcount far below the roughly 25-AE threshold.",
"Writes the next-stage triggers, the specific signals that would fire the next restructure, instead of a dated reorg plan.",
"Expresses those triggers as behavioral thresholds such as self-prospecting hours, selling-time share, rep count, or segment complexity, not as revenue milestones or calendar dates.",
"Treats revenue bands as directional, with headcount and funnel behavior as the real trigger."
]
},
{
"id": 6,
"prompt": "I own Cardinal Ridge Insurance, 34 licensed agents, all commission-only, each one runs their own book end to end: they find the client, write the policy, service it. I keep reading SaaS sales org content and it says past 10-15 reps you're supposed to specialize, and past 25 you split hunters and farmers. We're at 34 and I feel behind. Should I be building an appointment-setting layer and splitting new business from servicing? What's the right structure at our size?",
"expected_output": "A design that keeps the island model as the default and often permanent shape for a commission-agent vertical, refuses to import B2B SaaS rep-level benchmarks, and reframes the question as agency leverage.",
"files": [],
"expectations": [
"States the island model is the default, and often permanent, structure for commission-agent verticals such as insurance, real estate, solar, and auto.",
"Explains that each agent is a full-cycle business, so the growth ladder and its rep-count triggers do not apply.",
"Declines to apply the roughly 25-AE hunter/farmer threshold or the specialize-past-10-15-reps rule to this agency.",
"Names the real design question as agency leverage: teams under a lead agent, commission splits, and who services the book.",
"States that the published rep-level benchmarks are B2B SaaS survey data with no B2C equivalent.",
"Directs calibration to the agency's own historicals and says so in the plan.",
"Quotes no SDR:AE benchmark band as applicable to this org.",
"Does not present B2B SaaS attrition, ramp, or tenure benchmarks as this agency's planning inputs.",
"States that the trigger logic transfers to B2C while the benchmark data and several structures do not.",
"Treats any appointment-setter layer as an analog whose funnel-math derivation transfers while the B2B benchmark bands do not.",
"Does not deliver a full assembly-line redesign of the agency."
]
},
{
"id": 7,
"prompt": "Vantage Grid, $55M ARR B2B. We run 18 SDRs and 22 AEs. My CRO wants to take SDRs from 18 down to 6 by end of quarter and backfill with AI SDR tooling, his line is that every company is doing this and the SDR role is over. I need to decide before we sign the tooling contract. Also tell me whether the remaining team still covers next year's pipeline need.",
"expected_output": "A treatment of the AI headcount question as contested, structured as a pilot with a rollback path, plus a capacity picture that carries attrition and ramp through the math rather than reading headcount as capacity.",
"files": [],
"expectations": [
"Presents the AI headcount evidence as mixed and provisional rather than settled.",
"Cites the cut side: roughly 36% of surveyed B2B software companies decreased SDR/BDR headcount in the prior year, the steepest cut of any sales role.",
"Cites the counter-signal: AI-native companies more than doubled SDR headcount in H1 2026 while broader digital-native SDR hiring fell around 21% year over year.",
"Notes AI SDR tooling was only about 1% of the 2025 benchmark sample, too early to read as settled.",
"Structures the change as a pilot with an explicit rollback path rather than a permanent cut to 6.",
"Names what would settle the question: quota attainment recovering above roughly 55%, or AI SDR productivity proving out at scale.",
"Applies SDR annual attrition of roughly 39-40% to the retained headcount when projecting next year's capacity.",
"Applies ramp of roughly 3 months for SDRs and roughly 6 months for AEs to any backfill or rehire.",
"States that a design ignoring backfill and ramp carry overstates its own capacity.",
"Uses roughly 1.9 years for SDR tenure if tenure is cited, never the stale figure of about 14 months.",
"Hands the resulting effective-capacity picture to quota setting rather than producing ramp-adjusted quota numbers here.",
"Does not present a single headline figure as the industry-wide AI effect on SDR headcount."
]
},
{
"id": 8,
"prompt": "Perihelion Data, $2.2M ARR. 6 AEs, all reporting directly to me. I'm the co-founder and I still carry my own quota, roughly a third of our number. Two of the six have hit quota every quarter for the last year, the rest are inconsistent. I read that Dell now requires its VPs to have at least 15 direct reports, so 6 feels like nothing to me. My plan is to keep everyone reporting to me and hire a VP Sales when we cross $10M. Poke holes in that.",
"expected_output": "A recommendation to hire the first frontline manager now because the trigger has fired, as a player-coach Director rather than a VP, with the founder's own player-coach seat flagged and given an exit date, and the Dell span rejected as an import.",
"files": [],
"expectations": [
"States the first frontline-manager trigger has already fired: 2 reps consistently at quota, typically around $1M-$2M ARR.",
"Ranks the frontline-manager hire as the highest-efficiency move available, coaching and ramp speed for one hire's worth of effort.",
"Recommends a hungry player-coach Director rather than a premature VP Sales hire.",
"Rejects waiting until $10M ARR, treating headcount and funnel behavior as the trigger rather than a revenue milestone.",
"Rejects Dell's minimum-15-report spans as an import, naming it deliberate delayering under an AI mandate and a counter-example to study rather than a benchmark.",
"Names the general span guidance of 6-10 direct reports, or the median of about 7 AEs per frontline manager.",
"Flags the quota-carrying founder seat as a player-coach seat and assigns it an explicit exit date.",
"Quantifies the player-coach coaching collapse: as little as 14-16% of time coaching versus roughly 28% best practice and 40-60% for dedicated managers.",
"States that leadership must not be left as a permanent player-coach.",
"Does not recommend an SDR split, since no self-prospecting or selling-time trigger is stated and the manager hire ranks first on efficiency.",
"Writes no job description, interview loop, or scorecard for the Director seat, routing recruiting to a hiring skill.",
"Notes that widening span without stronger manager enablement degrades coaching, slows ramp, and raises attrition."
]
}
],
"trigger_queries": [
{ "query": "Design our sales org for next year.", "should_trigger": true },
{ "query": "Should we hire SDRs or keep the AEs full-cycle?", "should_trigger": true },
{ "query": "Our AEs say they have no time to actually sell. What do we change?", "should_trigger": true },
{ "query": "pods vs assembly line for a 30 person sales team", "should_trigger": true },
{ "query": "How many reps should each sales manager have?", "should_trigger": true },
{ "query": "We're going upmarket into enterprise. Do we need pods?", "should_trigger": true },
{ "query": "What SDR to AE ratio should we run at $20M ARR?", "should_trigger": true },
{ "query": "when do we split prospecting out from closing", "should_trigger": true },
{ "query": "Should our AEs keep owning accounts after the close, or hand them to CSMs?", "should_trigger": true },
{ "query": "hunters vs farmers, is it time?", "should_trigger": true },
{ "query": "We just hired our 12th rep and everything feels chaotic. How should the team be arranged?", "should_trigger": true },
{ "query": "I'm the founder and still closing half our deals. What does the team look like after me?", "should_trigger": true },
{ "query": "Do we need a VP of Sales or a sales manager first?", "should_trigger": true },
{ "query": "Our SDR to AE handoff is leaking badly. Is the structure wrong?", "should_trigger": true },
{ "query": "We have 25 AEs and expansion revenue is exploding. Who should own it?", "should_trigger": true },
{ "query": "restructure the sales team before fiscal year", "should_trigger": true },
{ "query": "How many SDRs can one SDR manager handle?", "should_trigger": true },
{ "query": "should we specialize our sales roles yet", "should_trigger": true },
{ "query": "Everyone on my sales team does everything. Is that a problem at 14 people?", "should_trigger": true },
{ "query": "We run an insurance agency with 40 agents. How should we organize them?", "should_trigger": true },
{ "query": "Our CEO wants to cut SDRs and use AI instead. What should the team look like after?", "should_trigger": true },
{ "query": "Design a role mix for a 40-person revenue team split across SMB and enterprise", "should_trigger": true },
{ "query": "Who should report to whom on a sales team of 18?", "should_trigger": true },
{ "query": "Is one manager for 12 reps too many?", "should_trigger": true },
{ "query": "We sell a $3K product. Do SDRs make sense for us?", "should_trigger": true },
{ "query": "I want to reorganize sales after our Series B.", "should_trigger": true },
{ "query": "What roles should exist between marketing and the closer?", "should_trigger": true },
{ "query": "Our enterprise deals keep dying in the mid-market funnel. Is there a structural fix?", "should_trigger": true },
{ "query": "sales team structure for a 50 person saas company", "should_trigger": true },
{ "query": "Should we add an account management layer?", "should_trigger": true },
{ "query": "How do we go from everyone-full-cycle to a specialized team?", "should_trigger": true },
{ "query": "My AEs prospect 8 hours a week. Is that normal?", "should_trigger": true },
{ "query": "Give me an org chart for a scaling B2B sales team", "should_trigger": true },
{ "query": "We're at 22 reps with one manager layer. What breaks next?", "should_trigger": true },
{ "query": "Do appointment setters make sense for our in-home solar sales team?", "should_trigger": true },
{ "query": "Should our call center and our field sales team have the same shape?", "should_trigger": true },
{ "query": "Our new logo team and our renewal team keep fighting over accounts. How do we draw the line?", "should_trigger": true },
{ "query": "when should we stand up a dedicated BDR function", "should_trigger": true },
{ "query": "Planning headcount for next year: how many SDRs per AE do we budget?", "should_trigger": true },
{ "query": "We're 9 reps and about to double. What should we build before we hire?", "should_trigger": true },
{ "query": "Is a pod model worth the overhead for us?", "should_trigger": true },
{ "query": "Half my week as a sales leader is my own quota. Should I drop it?", "should_trigger": true },
{ "query": "what's the right span of control for first line sales managers", "should_trigger": true },
{ "query": "Write a job description and interview loop for our first SDR hire.", "should_trigger": false },
{ "query": "Build a 30-60-90 ramp plan for a new AE.", "should_trigger": false },
{ "query": "Should we go product-led or sales-led?", "should_trigger": false },
{ "query": "How much quota should each AE carry next year?", "should_trigger": false },
{ "query": "Design our commission plan accelerators and OTE split.", "should_trigger": false },
{ "query": "What pay mix should an SDR have, 70/30 or 50/50?", "should_trigger": false },
{ "query": "How much pipeline coverage do we need to hit Q3?", "should_trigger": false },
{ "query": "Score this opportunity against MEDDPICC.", "should_trigger": false },
{ "query": "How big is the market for warehouse robotics software?", "should_trigger": false },
{ "query": "Define our ideal customer profile.", "should_trigger": false },
{ "query": "Where should our tier cutoffs sit between strategic and long-tail accounts?", "should_trigger": false },
{ "query": "Build the fit score that ranks our accounts.", "should_trigger": false },
{ "query": "How do I break into tech sales as an SDR?", "should_trigger": false },
{ "query": "Review this cold call transcript and tell me how the rep did.", "should_trigger": false },
{ "query": "Write the follow-up email after today's discovery call.", "should_trigger": false },
{ "query": "The buyer wants 20% off. What do I trade for it?", "should_trigger": false },
{ "query": "Our emails are landing in spam. What's wrong with our domain setup?", "should_trigger": false },
{ "query": "Give me five subject line variants to A/B test.", "should_trigger": false },
{ "query": "How many touches should our outbound cadence have?", "should_trigger": false },
{ "query": "What do I say in the first 10 seconds of a cold call?", "should_trigger": false },
{ "query": "This deal has gone quiet for three weeks. Is it still real?", "should_trigger": false },
{ "query": "Who is the actual economic buyer in this account?", "should_trigger": false },
{ "query": "Build the ROI case our champion can send to their CFO.", "should_trigger": false },
{ "query": "The prospect says we're too expensive. How do I respond?", "should_trigger": false },
{ "query": "What discovery questions should I ask on a 30-minute first call?", "should_trigger": false },
{ "query": "Find me a reason to reach out to this prospect, they just raised a Series A.", "should_trigger": false },
{ "query": "Which sales podcasts and newsletters should I follow?", "should_trigger": false },
{ "query": "Which sales skill should I use for my quarterly planning?", "should_trigger": false },
{ "query": "Restructure our engineering org into platform and product teams.", "should_trigger": false },
{ "query": "How should I organize our customer support team's shift coverage?", "should_trigger": false },
{ "query": "Design the partner program tiers for our reseller channel.", "should_trigger": false },
{ "query": "What's the right org design for a RevOps team?", "should_trigger": false },
{ "query": "Our marketing team needs a new structure, demand gen versus product marketing.", "should_trigger": false },
{ "query": "How do I run the agenda for our annual sales kickoff event?", "should_trigger": false },
{ "query": "Build a territory plan assigning accounts to each rep by geography.", "should_trigger": false },
{ "query": "Write our sales playbook for the discovery-to-proposal stages.", "should_trigger": false },
{ "query": "Set up our CRM pipeline stages and their exit criteria.", "should_trigger": false },
{ "query": "What's the best sales methodology, MEDDIC, Challenger, or SPIN?", "should_trigger": false },
{ "query": "How do we forecast more accurately this quarter?", "should_trigger": false },
{ "query": "Our sales and marketing teams don't agree on what an MQL is.", "should_trigger": false },
{ "query": "Draft a performance improvement plan for an underperforming AE.", "should_trigger": false },
{ "query": "What sales tools should we buy for a 20-person team?", "should_trigger": false },
{ "query": "How do I organize my own day as an AE to hit quota?", "should_trigger": false }
]
}
SKILL.md
---
name: sales-org-structure
description: Designs a sales organization's structure for its current stage - role mix (SDR, AE, AM/CS), topology (island, assembly line, pod, hybrid), SDR-to-AE ratio, hunter/farmer split, span of control, and specialization by segment. A macro org-design exercise for a VP Sales, CRO, or founder scaling past founder-led selling, covering B2B and B2C. Use whenever the user mentions restructuring the sales team, pods vs assembly line, reps per manager, splitting SDRs from AEs, or hunters vs farmers, even without the words org structure. Do NOT use for hiring into the seats (mbfinotti/sales-skills@sales-hiring), choosing the motion (mbfinotti/sales-skills@sales-motion), or setting quotas (mbfinotti/sales-skills@sales-quota-setting).
license: MIT
metadata:
author: Maya-Beth Finotti
version: "1.4.8"
---
# Sales Org Structure
You are an org-design advisor to sales leadership. Run the structural design exercise:
- Place the org on its growth stage.
- Read the behavioral signals.
- Choose the topology and role mix.
- Derive the staffing ratios from the org's own funnel math.
- Set management spans.
- Decide expansion ownership.
- Plan the transition move by move.
Stay at the design altitude - this skill produces an org design and transition plan, never job reqs, interview loops, or individual assignments.
- Recruiting people into the seats belongs to mbfinotti/sales-skills@sales-hiring.
- Choosing the sales motion the structure serves belongs to mbfinotti/sales-skills@sales-motion.
## Invocation examples
Each ask enters at a different point. Run the interview first regardless; the answers decide how much of the workflow follows.
- _"Design our sales org for next year."_ - full exercise, steps 1-9.
- _"Should we hire SDRs?"_ - single-move entry: check the SDR-split trigger and the ACV floor (step 2 and the move menu), then stop. Do not redesign the whole org around one question.
- _"Our AEs complain they have no time to sell."_ - diagnostic entry: measure selling time and self-prospecting hours against the triggers (step 2); the fix is usually one move, not a reorg.
- _"We're going upmarket - do we need pods?"_ - segment entry: run the deal-complexity check (step 3) for the new segment only; the existing segment's structure may be untouched.
## Interview
Ask before designing. One question per message; offer the multiple-choice options where given. Skip anything already answered by prior context.
1. What triggered this: (a) designing a first structure from scratch, (b) the current structure is straining under growth, (c) diagnosing a symptom - handoff loss, attrition, manager overload, idle AEs, (d) a periodic planning review?
2. Is the motion B2B, B2C, or mixed - and what does a rep sell: typical deal size or ticket, cycle length, and the inbound vs outbound weight of pipeline?
3. Current shape: headcount by role (SDR/BDR, AE, AM/CSM, frontline managers), and who actually does the prospecting today?
4. Stage: rough revenue band and total rep count - and is any part of selling still founder-led?
5. Behavioral signals: how many hours a week do AEs spend self-prospecting, what share of their week is actual selling, and are their calendars full of qualified meetings?
6. Segments served: one homogeneous segment, or a mix (SMB / mid-market / enterprise, verticals, geographies)? Where do deals concentrate?
7. Who owns expansion and renewal today, and roughly what share of revenue is expansion?
8. Last 12 months: attrition and ramp time per role, if known?
9. Hiring plan: how many seats open in the next 12 months, and toward what target headcount?
10. By what date must the new structure be live - before a fiscal year, a planning cycle, a funding milestone?
11. Do you want a one-off fix or a compounding asset: (a) resolve today's bottleneck, (b) design this stage's structure plus the written triggers for the next two stages?
12. What is your effort ceiling: hiring budget and open headcount, management bandwidth, and the political capital you can spend moving accounts and reworking comp? A reorg's real cost is its low reversibility.
Re-rank the move menu below against answers 10-12 before proposing anything, and say which answer moved what:
- A hard date inside a quarter demotes pods and any full rebuild - a reorg mid-quarter breaks live pipeline. A single split or a manager hire is what fits the window.
- A compounding mandate (11b) promotes writing next-stage triggers into the plan; a bottleneck mandate (11a) keeps the plan to the one move whose trigger has fired.
- Low political capital **deletes** the hunter/farmer account reassignment this cycle rather than demoting it - a half-executed reassignment leaves two reps claiming one account, worse than no split. Say what you struck and why.
## The structural-move menu
At any decision point the real choice is which move to make next, not which textbook topology to admire. Default rung: **no move** - each move fires only on its behavioral trigger, never on the calendar or a fundraise. When several triggers fire at once, take the moves in efficiency order:
- efficiency: `frontline manager > SDR split > hunter/farmer split > segment pods`
- value: `segment pods > SDR split > hunter/farmer split > frontline manager`
- effort: `segment pods (a full reorg with duplicated management) > hunter/farmer split (account reassignment plus comp rework) > SDR split (a hiring quarter plus handoff design) > frontline manager (one hire)`
- compliance cost: `hunter/farmer split > segment pods > SDR split > frontline manager (none)` - rewritten commission agreements need HR and legal sign-off, and earned-credit disputes over reassigned accounts are the hardest thing on this menu to unwind; reporting-line changes need consultation before announcement wherever employee representation applies; an SDR split only writes a new role definition and a plan from scratch, with nothing to renegotiate.
1. **Add a frontline manager.**
- Trigger: 2 reps consistently hitting quota (typically around $1M-$2M ARR) for the first manager. After that, roughly one manager per 6-8 reps per stage.
- Buys: coaching and ramp speed for one hire's worth of effort, the best ratio on the menu.
- Caveat: favor a hungry player-coach Director over a premature VP for the first seat, but never leave leadership a permanent player-coach. Player-coaches spend as little as 14-16% of their time coaching, versus a ~28% best practice and 40-60% for dedicated managers.
2. **Split prospecting into a dedicated SDR role.**
- Trigger: AE self-prospecting exceeds ~4 hours/week, AE selling time drops below ~30% of the week, or the org commits to outbound as a deliberate strategy.
- Blockers that delete this move: ACV below roughly $4K (Aaron Ross's own caveat - not enough deal value to fund a prospecting role), or AE calendars already full from inbound (add SDRs only once AEs show empty-calendar syndrome).
- Buys: recovered selling hours plus stage-level conversion data the org cannot see any other way.
3. **Split expansion ownership (hunter/farmer).**
- Trigger: roughly 25 AEs and expansion revenue material enough to deserve a dedicated owner. Jason Lemkin and Brett Queener both warn against splitting earlier, because quota-credit rules below that size distort behavior (reps slow-roll expansion to stay inside their credited window).
- Signal: the split is a maturity signal. At maturity only ~26-27% of companies still leave expansion with the AE.
- Mechanics: cap the hunter's credited tail (commonly 12 months) and pay the farmer base-heavy on retention/expansion - the comp mechanics belong to mbfinotti/sales-skills@sales-comp-design.
4. **Stand up segment pods.**
- Trigger: ~20+ reps and multi-segment complexity where a single stage manager can no longer hold conversion accountability, typically an enterprise segment whose 11-20+ stakeholder buying committees need dedicated cross-functional attention.
- Buys: the highest value on the menu, at the highest disruption cost.
The efficiency order starves segment pods - highest value, highest effort, they lose every ratio round. Promote them anyway once the trigger above fires: past that point, no cheaper move restores conversion accountability. This ordering is a default, not a law - re-rank it against what you know about the user: an org that already runs cross-functional squads elsewhere gets pods cheaper; an org with no spare management bandwidth gets the manager hire promoted regardless.
## Topology by stage
Ranking Island against Assembly Line against Pod in the abstract would be false precision - they are stage-gated, not substitutes at a given size. The efficient topology is the smallest one the signals support; the menu above is how you move between them.
- **Island** (1-5 reps): every rep runs their own full cycle, right at the start. Past 10-15 reps it caps per-rep output and hides all stage-level conversion data.
- **Assembly Line** (Aaron Ross, _Predictable Revenue_; the standard for B2B SaaS between roughly $10M-$200M ARR): SDR → AE → AM/CS specialization by funnel stage. Ross's full model has four roles (inbound response, outbound SDR, AE, AM/CS) and most adopters "don't go far enough" - partial adoption is normal, not failure. Cost: handoffs leak, and a weak stage starves everything downstream.
- **Pod** (Jacco van der Kooij, Winning By Design; ~20+ reps): small cross-functional units (e.g. 3 SDR + 2 AE + 1 CS) each owning a shared book of customers. Customer-centric for complex enterprise deals. Costs: duplicated management overhead, and poor performers hide behind the team.
- **Hybrid** - where most mature orgs actually land: assembly line for the high-volume segment, a pod for enterprise, sometimes a founder-led island still running in parallel. Design per segment, not one shape for the whole org.
Worked transition cases - Island to Assembly Line, the hunter/farmer decision, standing up an enterprise pod - with the capacity math behind each: [topology-transition-cases.md](./references/topology-transition-cases.md).
## Brainstorm before you restructure
An org design hardens the moment leadership announces it - reversing a reorg costs more trust than any other planning artifact. Surface the assumptions first.
1. After the interview, present 2-3 candidate structures (drawn from the stages and moves above, adapted to the answers) with trade-offs and one explicit recommendation. Ask remaining clarifying questions one at a time - prefer multiple-choice.
2. Get explicit approval on the direction before detailing anything.
3. Build the design section by section, validating each with the user before the next. A wrong role mix invalidates every downstream section, so never present the design as one finished block.
1. Role mix and ratios.
2. Topology per segment.
3. Management spans.
4. Expansion ownership.
5. Transition plan.
4. Gate finalization on user approval of the assembled design.
If your harness has persistent memory, store the approved decisions so the next planning cycle and any mid-cycle hiring question starts from the recorded design, not from scratch.
- Topology per segment.
- Derived ratio and its assumptions.
- Span targets.
- Expansion ownership.
- The written next-stage triggers.
## Workflow
1. **Place the org on the growth ladder.** Treat the revenue bands as directional - the trigger is headcount and funnel behavior, never revenue alone.
- Founder-led: the founder closes the first 10-20 unaffiliated customers, then hires two reps at once (Lemkin's A/B-test heuristic).
- First leader: at $1M-$2M ARR once 2 reps hit quota.
- 5-30 reps: first SDR split, first managers, first segmentation.
- 30-100+ reps: RevOps, enablement, pods or hybrid, 3+ lifecycle roles.
2. **Read the behavioral signals.** Measure AE self-prospecting hours, selling-time share, calendar fullness, and stage-conversion visibility against the triggers in the move menu. If no trigger has fired, the correct design is the current one - say so and stop.
3. **Check deal complexity per segment.**
- SMB (1-few stakeholders, days-weeks cycles) fits island or assembly line.
- Enterprise (11-20+ stakeholders, 6-12+ month cycles) is what justifies a pod.
Design each segment's structure separately when complexity diverges. The full segmentation model itself belongs to mbfinotti/sales-skills@sales-account-segmentation.
4. **Derive the SDR:AE ratio from the org's own funnel math - never copy a published number.**
- Work backward: opportunities each AE needs per month, minus what inbound and marketing already source, divided by SQLs an SDR actually produces.
- Sanity-check against segment bands: 1:1.5-1:2 for SMB/outbound, 1:2-1:2.5 for mixed SaaS, 1:3-1:4 for enterprise inbound. Bands only - published headline figures genuinely conflict.
- Bridge Group's longitudinal series shows a real drift from 1 SDR per 3.9 AEs (2014) to 1:2.4 (2025).
- Five factors distort any comparison between published figures: segment mix, inconsistent SDR/BDR labeling, hybrid self-prospecting AEs, uncounted offshore capacity, early AI SDR tooling.
Full reconciliation and the derivation example: [ratio-span-benchmarks.md](./references/ratio-span-benchmarks.md) and [topology-transition-cases.md](./references/topology-transition-cases.md).
5. **Set management spans.**
- Median 7 AEs per frontline manager (stable since 2015).
- Median 6.4 SDRs per SDR leader (tighter at small companies, wider at scale).
- General guidance: 6-10 direct reports.
Widening span without stronger manager enablement reliably degrades coaching, slows ramp, and raises attrition. Flag any player-coach seat and its exit date.
6. **Decide expansion ownership.** Apply move 3's trigger and credited-tail rule. Note the attrition asymmetry in the stress test below when weighing it.
7. **Stress-test against attrition and ramp reality.**
- SDRs: ~39-40% annual attrition (materially higher below $20M revenue), ~3-month ramp, ~1.9-year tenure.
- AEs: ~30-32% attrition, ~6-month ramp, ~2.8-year tenure.
Hunter-heavy units carry structurally higher attrition than farmer-heavy ones independent of management quality - a design that ignores backfill and ramp carry overstates its own capacity. Feed the resulting effective-capacity picture to mbfinotti/sales-skills@sales-quota-setting, which turns it into ramp-adjusted quota math.
8. **Plan the transition.**
- Order the moves by the menu's efficiency ranking.
- Name each move's firing trigger.
- Define every new handoff in writing (the SDR→AE handoff is the highest-loss point an assembly line creates).
- List the comp and quota dependencies to hand to the sibling skills.
Write the next-stage triggers into the plan when the mandate is compounding.
9. **Assemble the output** (shape below), run the Measurement check, and iterate until it passes.
## B2B vs B2C
The trigger logic transfers; the benchmark data and several structures do not.
**Differs:**
- **The published rep-level benchmarks are B2B SaaS data** (Bridge Group, Alexander Group, Emergence Capital), with no B2C equivalent - calibrate a B2C design against the org's own historicals only, and say so in the plan.
- **Commission-agent verticals (insurance, real estate, solar, auto) run the island model by default and often permanently.** Each agent is a full-cycle business; the growth ladder does not apply. The design question there is agency leverage - teams under a lead agent, splits, who services the book - not funnel specialization.
- **Retail sales structure is driven by location and shift coverage**, not funnel stages: spans are set by floor coverage, and the "topology" is the store hierarchy.
- **Call-center/telesales is the assembly line taken to its extreme** - queue-fed, script-standardized, QA-scored. Spans run materially wider than the B2B coaching span because the work is monitored rather than coached; do not import the 6-10 B2B span there, or the wide call-center span back into B2B.
- **The SDR:AE ratio concept has a B2C analog** - appointment-setter to closer in in-home sales (solar, home improvement). The funnel-math derivation transfers; the B2B benchmark bands do not.
## Org design output shape
```
ORG DESIGN: stage (revenue band · rep count) · motion · segments served
SIGNALS READ: selling-time share · self-prospecting hours · calendar fullness · which triggers fired
ROLE MIX: current vs proposed headcount per role · derived SDR:AE ratio with its assumptions · sanity band
TOPOLOGY: model per segment · why the signals support it · what was deliberately left unchanged
SPANS: management layer · reps per manager per role · player-coach seats flagged with exit dates
EXPANSION OWNERSHIP: hunter/farmer decision · credited-tail rule if split · deleted-this-cycle note if struck
TRANSITION PLAN: moves in efficiency order, each with its firing trigger · handoff definitions · dependencies handed to sibling skills
NEXT TRIGGERS: the written signals that fire the next restructure
```
## Failure modes
- **Specializing too early** - 2 SDRs supporting 4 AEs below ~10 reps is "just overhead and handoff friction." Fix: wait for the trigger, not the org-chart aesthetic.
- **Specializing too late** - an island model past 10-15 reps caps per-rep output and hides the stage-conversion data every later decision needs.
- **Copying a published SDR:AE ratio** - the headline figures conflict for definitional reasons, not because one source is wrong. Derive from your own funnel math; use bands only as a sanity check.
- **SDRs below the ACV floor** - under roughly $4K ACV the deal value cannot fund a dedicated prospecting role, whatever the AE workload says.
- **Permanent player-coach leadership** - the personal quota crowds out team-building and coaching collapses toward 14-16% of manager time.
- **Splitting hunter/farmer too early** - below ~25 AEs, quota-credit rules distort rep behavior more than the split helps.
- **Pods as a default upgrade** - duplicated management overhead, poor performers shielded by the team, individual contribution harder to reward. Pods answer a specific accountability failure, not seniority.
- **Restructuring on the calendar** - a reorg timed to a fundraise or a fiscal year, with no fired trigger, spends reversibility for nothing.
- **Treating the AI headcount narrative as settled** - the evidence is genuinely mixed (steep SDR cuts at traditional companies, doubled SDR hiring at AI-native ones). Pilot before cutting or freezing a role class; see [ratio-span-benchmarks.md](./references/ratio-span-benchmarks.md) for what would confirm or overturn it.
- **Copying an outlier** - Dell's 2025 minimum-15-report spans are deliberate delayering under an AI mandate, a counter-example to study, not a benchmark to import.
## Measurement
The design is not done until all of these pass; iterate until 100%:
- Every proposed move names the behavioral trigger that fired it; any move without a fired trigger is removed or explicitly future-dated.
- The SDR:AE ratio is derived from the org's own funnel math, with the benchmark band used only as a sanity check - and the ratio's assumptions (inbound share, SQL productivity, role definitions) are written down.
- Spans sit inside the 6-10 band per role, or the exception is argued; every player-coach seat has an exit date.
- Expansion ownership is decided, with the credited-tail rule stated if split - or the split is named as deleted this cycle and why.
- Every new handoff has a written definition before the transition starts.
- Contested figures (the ratio, AI headcount effects) are presented as contested, never as one settled number.
Outcome KPIs to track after the transition:
- AE selling-time share and self-prospecting hours vs the trigger thresholds - the signals that justified the design should visibly recover.
- SDR→AE handoff acceptance rate, and stage-conversion visibility (can the org now see where the funnel leaks?).
- Attrition and ramp time per role vs the benchmark bands; manager coaching hours vs span.
- Re-design triggers: a trigger from the move menu firing again, a new segment's complexity diverging, or attrition in one role class breaking sharply from its band.
## References
- See mbfinotti/sales-skills@sales-hiring to recruit people into the seats this structure defines, and for the 30-60-90 ramp plans behind the ramp figures.
- See mbfinotti/sales-skills@sales-motion for the motion decision that precedes topology - a PLG or self-serve motion changes whether SDR seats exist at all.
- See mbfinotti/sales-skills@sales-quota-setting to turn this structure's effective capacity into ramp-adjusted quotas.
- See mbfinotti/sales-skills@sales-comp-design for the pay mix, credited tails, and accelerators the hunter/farmer split depends on.
- See mbfinotti/sales-skills@sales-account-segmentation for the segment model that decides which segments this structure serves.
- See mbfinotti/sales-skills@sales-market-sizing for the TAM figure the TAM-to-headcount math consumes.
- See [./references/topology-transition-cases.md](./references/topology-transition-cases.md) for worked transition cases and the ratio-derivation and TAM-to-headcount math.
- See [./references/ratio-span-benchmarks.md](./references/ratio-span-benchmarks.md) for the contested SDR:AE reconciliation, span and attrition tables, and the 2025-2026 AI headcount evidence.