evals/evals.json
{
"skill_name": "sales-career",
"evals": [
{
"id": 1,
"prompt": "I'm 34, been managing a Verazo Home Goods store in Columbus for six years, $58K salary, and I want out. My cousin makes serious money in real estate here and keeps telling me it's uncapped, so I'm ready to go get licensed and hustle. Only problem is my wife's maternity leave ends and our budget stops working unless I'm earning again by December 1st. We have about $7,200 in savings. What's my move?",
"expected_output": "An interview-first response that treats the sub-3-month date and the thin runway as hard constraints, deletes the licensed real-estate route by name rather than ranking it last, presents 2-3 surviving paths with a stated ordering and benchmark-anchored trade-offs, and gates the roadmap on an explicit pick.",
"files": [],
"expectations": [
"Asks clarifying interview questions before proposing any path, rather than delivering a finished plan in the first reply",
"Treats December 1 as a hard date under three months and states that this promotes the salaried B2B entry route",
"Records the licensed real-estate path as deleted and names the constraint that deleted it (the sub-three-month date, the sub-three-month savings runway, or both)",
"Does not present real estate as an option sitting at the bottom of a ranked menu",
"Cites the NAR 2026 Member Profile figure that agents with two years or less of experience had a median gross income of about $8,000, naming the publisher",
"Names the jurisdiction-bound licensing exam, continuing education, and brokerage sponsorship as a compliance cost that the B2B routes do not carry",
"Presents between two and three surviving paths, never one and never five",
"States the ordering used for the surviving paths out loud with its axis named, rather than leaving the order implied by list position",
"Describes each surviving path in a rep's terms: entry difficulty, comp shape, realistic first-two-years income, promotion or book-building timeline, and washout risk",
"Names the conflict between the user's appetite for an uncapped ceiling and his $7,200 runway, and makes the user resolve it rather than resolving it silently",
"Closes with exactly one recommendation tied to the user's date, geography, and comp priority",
"Requires an explicit pick from the user before building any roadmap, and states that passive agreement does not count as a pick"
]
},
{
"id": 2,
"prompt": "Quick gut check. I've been an SDR at Palterra (mid-market HR software) for 8 months, hit 112% of my meeting target three quarters running, and my VP just offered me an AE seat starting next month - SMB segment, $85K base, $170K OTE. My roommate says take it before they change their mind. Am I crazy to even hesitate?",
"expected_output": "A recommendation against taking the seat at month 8, anchored to the Bridge Group early-promotion failure split and the median time in seat, with a dated decision point and a reframe of the meeting-target number as an input metric.",
"files": [],
"expectations": [
"Advises against taking the AE seat at month 8 as offered, rather than congratulating the user and confirming the move",
"Cites the early-promotion failure split: roughly 55% AE failure for SDRs promoted before 11 months against roughly 6% for those with 16+ months in seat",
"Attributes that split to The Bridge Group as a primary source rather than presenting the figures unattributed or as second-hand",
"States the study's failure definition (leaving the AE seat within six months) or its sample size (n=205)",
"Cites the median of about 16 months in an SDR seat before promotion, attributed to Bridge Group",
"Recommends accumulating roughly 12-16 months of in-seat evidence before taking the AE jump",
"Mentions the overall SDR-to-AE failure rate of about 26%, the 41% rate for SDRs who changed companies to take the AE role, or both",
"Notes that this internal promotion avoids the higher failure rate attached to changing companies for an AE seat",
"Does not claim that three quarters of meeting-target attainment predicts AE success",
"Treats the 112% meeting-target figure as an activity or input metric and asks for outcome evidence such as pipeline sourced or closed-won influenced",
"Gives the user a dated decision point for re-opening the AE conversation rather than an open-ended instruction to wait longer",
"Labels every benchmark used with its publisher and edition rather than stating figures free-floating"
]
},
{
"id": 3,
"prompt": "Got an offer from Nuvexa (Series B, revenue intelligence) - mid-market AE, $110K base, $215K OTE, 50/50 split, $900K annual quota, plus 0.08% equity. The recruiter says the team is crushing it right now. My current job pays $150K all-in and is boring. Should I take the $215K?",
"expected_output": "A refusal to value the offer at face OTE, an explicit re-valuation at the team's real attainment, the diligence questions to ask before deciding, and a total-comp comparison against the current $150K.",
"files": [],
"expectations": [
"Refuses to treat the $215K OTE as $215K and re-values it at the team's real attainment rather than at 100%",
"Shows the re-valuation arithmetic explicitly: expected variable equals the variable component multiplied by the team attainment rate",
"Applies the roughly 43% market attainment baseline from the RepVue Cloud Sales Index as the default when the team's own number is unknown",
"Labels that RepVue baseline as crowdsourced rather than presenting it as a verified published figure",
"Produces the question asking what percentage of people in this exact role, on this exact team, hit quota last quarter",
"Produces the quota-capacity question: how many reps carry what quota, against what company goal",
"States that a refusal to answer the attainment question is itself the answer and should be scored as data",
"Cites the interpretation band from a VC diligence framework: aggregate attainment of 60-70% is bad numbers, 85-100% is really good",
"Flags the recruiter's crushing it claim as a headline with no attainment data behind it, matching a documented offer red flag",
"Instructs the user to build a 25th/50th/75th percentile comp band for the exact role, level, and location, noting each source and its pull date",
"Compares total compensation (base plus variable at real attainment plus equity plus benefits) against the current $150K rather than comparing base to base",
"Asks what quota is during ramp and how long ramp lasts before the decision is made",
"Does not tell the user to accept or decline before the team attainment answer is in hand"
]
},
{
"id": 4,
"prompt": "Cleaning up my resume before I apply to AE roles. Tell me if these bullets land: (1) Closed $1.4M in new ARR against a $750K quota, 187% attainment, FY2025. (2) Averaged 22 closed-won deals per year at a $48K average deal size. (3) Exceeded quota every single year since 2022 - 120%, 134%, 151%, 187%. (4) Ran 40+ discovery calls a month. Anything you'd punch up?",
"expected_output": "An arithmetic, provenance, and depth audit of every quantified claim that catches the deal-count mismatch, flags the unbroken 100%+ streak as a red flag, and reframes failing claims instead of polishing or padding them.",
"files": [],
"expectations": [
"Runs an arithmetic cross-check on the claims rather than only improving their wording",
"Flags that 22 deals at a $48K average size yields about $1.06M, which does not reconcile with the $1.4M closed figure",
"Confirms that $1.4M against a $750K quota does compute to roughly 187%, rather than flagging that claim as wrong",
"Flags four consecutive years of 100%+ attainment as itself a red flag, because fewer than half of reps hit quota in a given year",
"Refuses to invent, pad, or round any number upward to make a bullet stronger",
"Applies a provenance check: asks where each number comes from and whether a reference would answer yes to a factual confirmation of it",
"Applies a depth check: asks whether the user can tell the quarter-level deal story behind the number for about two minutes",
"Offers the reframing options for a failing claim - a range, a conservative bound, or an input metric - rather than only deleting it",
"Treats the 40+ discovery calls per month bullet as an input or activity metric and repositions it behind an outcome such as pipeline sourced or meetings converted",
"States that the evidence audit passes only at 100% of claims and that nothing is deliverable while any claim fails",
"Names hiring-side verification methods the audit anticipates, such as a math audit, quarterly probes, W-2 cross-checks, or off-list references",
"States that getting caught padding disqualifies the candidate, rather than treating padding as a stylistic risk",
"Re-runs the audit after any reframe rather than accepting a rewritten claim as settled"
]
},
{
"id": 5,
"prompt": "Helios Ridge Solar in Phoenix offered me a closer role - no base, but a $3,000/month draw and unlimited earning potential, and they say their reps clear $110K. I've got about five weeks of expenses saved and I start Monday if I say yes. Talk me through it.",
"expected_output": "A written draw-terms checklist demanded before acceptance, the runway shortfall named explicitly, the vague comp claim flagged as a red flag, and a warning that the Monday timeline cannot be met responsibly.",
"files": [],
"expectations": [
"Requires the draw terms in writing before any acceptance, and says so explicitly",
"Asks whether the $3,000 monthly draw is recoverable or non-recoverable",
"Requires the recovery schedule in writing: which commissions repay the draw, and at what rate",
"Requires written treatment of a negative draw balance at separation, naming it as the main source of final-pay disputes",
"Requires clawback conditions on cancelled or refunded sales, including the clawback window",
"Requires a lead-flow commitment in measurable terms: who generates the leads and what share of pipeline they are expected to be",
"States the 3-6 month savings runway requirement before accepting a straight-commission seat and identifies the user's five weeks as falling short of it",
"Flags unlimited earning potential offered as the only comp statement as a documented B2C offer red flag",
"Does not accept the reps clear $110K claim at face value as the user's expected income",
"States that B2C compensation data is thin and directional compared with B2B benchmarks, rather than quoting B2C figures with equal confidence",
"Advises against saying yes by Monday without the written terms, rather than helping the user decide inside that timeline",
"Ranks the lead-flow question alongside the team-attainment question for a commission seat, because a commission seat with no lead flow has no attainment worth asking about"
]
},
{
"id": 6,
"prompt": "Seven years as a backend engineer working on distributed systems at a payments company, currently $185K. I'm burnt out on writing code and I want the money and the freedom of enterprise sales. My plan is to apply straight to enterprise AE roles at infrastructure vendors since I know the buyer's world cold. How do I position that?",
"expected_output": "A re-ranked entry ordering that routes the technical background through sales engineering or CSM rather than straight to enterprise AE, with the enterprise-AE gate named and the route deleted if it cannot be bridged inside the user's date.",
"files": [],
"expectations": [
"Recommends routing into sales through sales engineering or a CSM seat rather than applying straight to enterprise AE",
"Justifies that routing with the fact that sales engineers share accounts with AEs and already know the product, and convert into strong reps",
"Presents the technical background as a user fact that re-ranks the default entry ordering, not as an exception carved out of it",
"States the employer gate on enterprise AE seats: prior enterprise selling exposure, which this candidate cannot yet evidence",
"Deletes the direct enterprise-AE route while naming the constraint that deleted it, if the gate cannot be bridged inside the user's timeframe, rather than ranking it last",
"Does not claim that domain knowledge of the buyer substitutes for a quota-carrying track record",
"Presents two to three surviving paths with a stated ordering and its axis named",
"Gives enterprise AE comp with its benchmark label, roughly $240-320K OTE at a 55:45 to 60:40 split, rather than an unsourced figure",
"Surfaces the sales-engineer comp anchor (BLS May 2024 mean of about $130,410) against the current $185K so the pay change is visible rather than glossed",
"Asks for the date by which the move must land, plus the user's effort ceiling and reversibility requirement, before recommending a path"
]
},
{
"id": 7,
"prompt": "Final panel at Corvane Analytics next Thursday for an SDR role. It's me, the SDR manager, and a director. I was a barista and shift lead for three years, then did two years of fundraising for a university - I've never carried a sales quota. I asked what to expect and they said a short role-play and some behavioral questions. Help me not blow it.",
"expected_output": "All four candidate artifacts prepared in build order, the role-play identified as the most predictive stage, adjacent quantified proof built from the fundraising and retail numbers, and panel questions drawn from the diligence list.",
"files": [],
"expectations": [
"Prepares all four candidate artifacts rather than selecting one as most important: a STAR story bank, a mock-call plan, a sell-me-this-pen answer, and a 30-60-90 plan if the employer asks for one",
"States that the four artifacts are in build order and are not ranked against each other, because each covers a different stage of the loop",
"Specifies the STAR bank as five competency buckets with each story rehearsed at three lengths: about two minutes, sixty seconds, and fifteen seconds",
"Includes a miss-and-recovery story in the story bank, not only wins",
"Requires the sell-me-this-pen answer to qualify with questions before pitching and to end with an explicit ask for the business",
"Identifies the role-play as the most predictive stage of the loop, citing that it predicts up to about 29% of future job success",
"Names feature-dumping and passivity as the behaviors interviewers punish",
"Names discovery questions, listening, adapting to a curveball, and an explicit close as what interviewers reward",
"Converts the user's fundraising totals and shift-lead retail numbers into quantified adjacent proof, positioned as evidence of persuasion, resilience, and target-hitting",
"Instructs the user to rehearse the mock call aloud rather than silently",
"Supplies at least two questions for the user to ask the panel, drawn from the diligence list and starting with the team-level quota attainment question",
"Warns against questions answerable from the company website, pure comp questions before an offer, and yes/no questions",
"Warns that having no questions for the panel, or never asking for the close, loses the room"
]
},
{
"id": 8,
"prompt": "I'm an SDR at Brightloom and I'm interviewing internally for the AE seat. Two things: first, draft the 30-60-90 I'll present in the panel. Second, since I'll basically be helping them design this role anyway, write the interview scorecard they should grade me on and the ramp plan the company should put new AEs on.",
"expected_output": "The candidate-authored 30-60-90 plan produced and anchored to benchmarks and named accounts, with the employer scorecard and company ramp plan declined as hiring-side work and routed to the sibling hiring skill.",
"files": [],
"expectations": [
"Produces the candidate-authored 30-60-90 plan as an interview deliverable",
"Declines to produce the employer's interview scorecard, naming it as hiring-side work outside this scope",
"Declines to produce the company's ramp plan for new AEs, naming it as hiring-side work outside this scope",
"Points the user to the employer-side hiring skill for the scorecard and ramp plan, referencing it as mbfinotti/sales-skills@sales-hiring",
"Builds the 30-60-90 plan from public benchmarks, named target accounts, and SMART phase goals rather than generic phase labels",
"Aims the plan at demonstrating the candidate will be at quota by month 5-6",
"Warns that generic phase labels with no numbers read as a template found online",
"Anchors the ramp expectation to a labeled benchmark, such as the Bridge Group AE ramp of about 4.3 months, rather than an invented timeline",
"Does not merge the candidate's plan and the employer's ramp plan into a single document"
]
},
{
"id": 9,
"prompt": "I'm four years into an AE seat at Tessaract Cloud, $198K OTE, hit 104% last year and 97% the year before. I'm bored and I want to make real money. A director here keeps hinting at a team lead opening in Q1. I've never managed anyone but I figure I'd learn. What's the smart next move - management, or is there something better?",
"expected_output": "The beyond-AE menu presented with multiple stated axes, management gated on coaching evidence the user lacks and flagged for low reversibility, senior/enterprise AE surfaced as the efficiency winner, and RevOps and enablement tied with the tie justified.",
"files": [],
"expectations": [
"States that sales management raises OTE but converts personal quota into team risk, rather than presenting it as a straightforward raise",
"Gates the management recommendation on coaching evidence, and states that the user's never managed anyone answer fails that gate",
"States that management is among the least reversible moves on the list because a returning ex-manager restarts on a rep's quota",
"Notes that a manager seat can be a pay cut relative to a top producing rep, not only an increase",
"Presents the beyond-AE menu with its ordering stated out loud and its axis named, rather than as an unordered list of options",
"Emits more than one axis where the axes disagree, covering at least efficiency, income ceiling, income stability, and effort, rather than a single blended ranking",
"Identifies senior or enterprise AE as the highest-efficiency move for a producing AE, at roughly $240-320K OTE",
"States the RevOps precondition: a year or more of data, CRM, and SQL fluency that must already be evidenced, bought with a pay cut",
"States that RevOps and sales enablement land in the same base-heavy pay band and both remove quota, so they differ in the preparation demanded rather than in what they pay",
"Distinguishes wanting to coach from wanting to earn and asks the user which it is before recommending the team lead seat",
"Attaches a publisher label to each comp figure used rather than quoting unsourced numbers",
"States that no rigorous failure rate is published for the player-to-coach transition, rather than inventing one"
]
},
{
"id": 10,
"prompt": "14 months as an SDR at Ferrolane (logistics SaaS). I average 96% of target, my manager says I'm on the radar for AE but nothing's been put in writing, and two people hired after me already moved up. I'm thinking of knocking out a Sandler cert, the HubSpot sales cert, and a Challenger course this quarter to make my case. Thoughts?",
"expected_output": "A redirect from certificate stacking to one methodology family plus work samples, the month-12 exit trigger identified as already passed, outcome evidence substituted for activity, and dated milestones with a re-route rule.",
"files": [],
"expectations": [
"Advises against stacking multiple generic sales certificates and recommends investing in one recognized methodology family instead",
"States that work samples outweigh paper credentials for this decision",
"Identifies on the radar with nothing in writing as the stalled-SDR trap rather than as progress",
"States the rule that a documented AE-path conversation should have happened by month 12, and that the user is now past that trigger",
"Recommends starting the external search, or fixing a hard date for the documented path conversation, rather than waiting for the manager to act",
"Cites the benchmark that roughly 40-60% of SDRs who stay 12 or more months are promoted internally, and labels it as an aggregated estimate rather than a hard published figure",
"Cites the Bridge Group median of about 16 months in an SDR seat before promotion, so 14 months reads against a benchmark rather than against feeling",
"Cites that a formal SDR-to-AE path exists at about 69% of B2B companies (Bridge Group 2023 edition, 434 executives) and uses it to test whether Ferrolane has one at all",
"Converts the user's case into outcome evidence such as pipeline sourced and meetings booked and converted, rather than dials, emails, or activity volume",
"Attaches a date and a named exit trigger to each milestone it sets",
"Applies the re-route rule: no movement after four to six weeks of executed actions means re-running the path-weighing step, because the path rather than the effort is usually what is wrong",
"Names weekly leading indicators to track, such as applications-to-screen rate, screens-to-role-play rate, role-plays-to-offer rate, and the date of the next documented path conversation"
]
},
{
"id": 11,
"prompt": "I've got three companies I'm seriously considering - Kelway Systems, Orrindale, and Pentamere Software - and maybe six hours total this week to research them. I usually just read Glassdoor reviews and call it a day. Where should those six hours actually go?",
"expected_output": "An explicit source ordering by decision-changing truth per hour, with RepVue first, the progression.fyi and Levels.fyi tie justified, Glassdoor demoted, Bridge Group placed outside the ordering, and the diligence questions given in ask-first order.",
"files": [],
"expectations": [
"Ranks the research sources explicitly rather than listing them flat: RepVue first, then progression.fyi and Levels.fyi, then Glassdoor last",
"States the ranking's axis, decision-changing truth bought per hour of digging, rather than leaving the order implied by list position",
"Justifies RepVue's first position as the only source carrying team-level attainment, the number that re-values the offer",
"Justifies the progression.fyi and Levels.fyi tie rather than leaving it unexplained: each answers one structured question at the same cost, and which to open depends on whether the doubt is comp or promotion",
"Demotes Glassdoor explicitly, naming its reviews as self-selected and noisy",
"Places The Bridge Group outside the ordering, stating it benchmarks the role and never a specific employer",
"Gives the diligence questions in ask-first order: team attainment first, then quota capacity against company goal, then ramp quota and last quota raise",
"Justifies the tie between the ramp-quota and last-quota-raise questions: each moves the same number, first-year expected variable, and neither overrides what the attainment question already answered",
"States that a refusal to give last quarter's team attainment is a red flag regardless of the OTE",
"Does not recommend spending the majority of the six hours reading Glassdoor reviews"
]
},
{
"id": 12,
"prompt": "OK, I've decided - corporate B2B isn't for me, I want the commission-heavy world where what I make is up to me. I'm in Tampa, 29, single, about $26K saved, no license yet, and honestly I'd love to build something that's mine long term. Real estate, insurance, solar, car sales - which one and why?",
"expected_output": "The B2C sub-ranking presented with its efficiency axis and separate effort and compliance-cost orderings, the compounding-asset answer used to promote real estate against its default rank once the local-network condition is tested, and an explicit pick required before any roadmap.",
"files": [],
"expectations": [
"Presents the B2C sub-ranking explicitly with its default efficiency order: auto, then solar, then insurance, then real estate",
"States the axis behind the efficiency order, income bought per year of unpaid runway, rather than leaving the order implied",
"Emits separate orderings where the axes disagree, including at least effort and compliance cost alongside efficiency",
"Asks whether the user has a local network or referral base in the Tampa jurisdiction before recommending real estate, rather than assuming one",
"Identifies the user's build something that's mine long term answer as the compounding-asset signal that promotes real estate above its default efficiency rank",
"States the real-estate promotion conditions explicitly: a local network or referral base, 12 or more months of runway, and a compounding-asset priority",
"Cites the NAR 2026 figures with their publisher: about $8,000 median gross income for agents with two years or less, and about $88,500 at 16 or more years",
"Cites the auto benchmark of roughly $68,400 median alongside its 40-70% annual turnover and 50-60+ hour weeks",
"Cites that roughly 89% of new insurance agents are gone within three years and labels it as directional trade-source data",
"Justifies the insurance and solar tie on income within two years rather than breaking it arbitrarily, on the grounds that both are reported only as overlapping ranges from thin sources",
"Applies a compliance-cost axis only to real estate and insurance, naming the jurisdiction-bound licence, continuing education, and brokerage sponsorship, and stating that the licence does not travel if the user relocates",
"Requires an explicit pick from the user before building the roadmap rather than choosing a vertical on their behalf"
]
}
],
"trigger_queries": [
{ "query": "How do I break into tech sales with no sales experience?", "should_trigger": true },
{ "query": "sdr interview prep", "should_trigger": true },
{ "query": "I'm an SDR and I want to become an AE - what's the path?", "should_trigger": true },
{ "query": "Evaluate this sales offer for me: $95K base, $190K OTE, $800K quota.", "should_trigger": true },
{ "query": "Is 8 months too early to take an AE promotion?", "should_trigger": true },
{ "query": "What should I ask a sales manager before accepting the job?", "should_trigger": true },
{ "query": "I got offered a straight-commission closer role with a draw. Good idea?", "should_trigger": true },
{ "query": "Should I get my real estate license or try to get into SaaS sales?", "should_trigger": true },
{ "query": "My resume says 145% attainment but I'm not sure the numbers add up. Can you check?", "should_trigger": true },
{ "query": "how do i prep for a sell me this pen question", "should_trigger": true },
{ "query": "I have a mock cold call in my final interview next week.", "should_trigger": true },
{ "query": "Help me write a 30-60-90 day plan for my AE interview.", "should_trigger": true },
{ "query": "I've been an AE for five years - what's next, management or something else?", "should_trigger": true },
{ "query": "Is RevOps a good move out of a quota-carrying seat?", "should_trigger": true },
{ "query": "I'm burnt out on coding and want to move into sales. Where do I start?", "should_trigger": true },
{ "query": "what's a realistic OTE for a mid-market account executive", "should_trigger": true },
{ "query": "My manager keeps saying I'm on the radar for AE but nothing's in writing.", "should_trigger": true },
{ "query": "I want to quit my retail job and make real money. What roles should I look at?", "should_trigger": true },
{ "query": "How long should I stay an SDR before moving up?", "should_trigger": true },
{ "query": "Should I take the higher OTE offer or the one with the better base?", "should_trigger": true },
{ "query": "I have no sales numbers to put on my resume. What do I use instead?", "should_trigger": true },
{ "query": "career roadmap for someone trying to get into enterprise sales", "should_trigger": true },
{ "query": "Which is better long term - insurance sales or car sales?", "should_trigger": true },
{ "query": "how do i know if a sales team's quota is actually attainable before i join", "should_trigger": true },
{ "query": "Talk me out of taking this commission-only job.", "should_trigger": true },
{ "query": "I keep getting to the role-play round and then getting rejected.", "should_trigger": true },
{ "query": "what certifications are actually worth it for a salesperson", "should_trigger": true },
{ "query": "Should I do Sandler or Challenger training to get promoted?", "should_trigger": true },
{ "query": "I want to go from SMB AE to enterprise AE. What do I need?", "should_trigger": true },
{ "query": "how much do SDRs actually make", "should_trigger": true },
{ "query": "Help me decide between taking a CSM role and staying in a closing seat.", "should_trigger": true },
{ "query": "I'm a teacher and I want to switch to sales. Is that realistic?", "should_trigger": true },
{ "query": "break into saas sales", "should_trigger": true },
{ "query": "I need to be earning by January and I'm unemployed. What job can I land fastest?", "should_trigger": true },
{ "query": "What questions should I ask in an interview to spot a bad sales team?", "should_trigger": true },
{ "query": "Is a $250K OTE at a Series A startup real or fake?", "should_trigger": true },
{ "query": "my first year in real estate and i've made almost nothing", "should_trigger": true },
{ "query": "Should I put my quota attainment on my LinkedIn headline?", "should_trigger": true },
{ "query": "How do I explain a year where I missed quota in an interview?", "should_trigger": true },
{ "query": "What does a brag book look like for a sales interview?", "should_trigger": true },
{ "query": "I'm a nurse looking at pharma sales - how do I position that?", "should_trigger": true },
{ "query": "how to get promoted from bdr to account executive", "should_trigger": true },
{ "query": "Which sales role has the best work-life balance?", "should_trigger": true },
{ "query": "I want the biggest income ceiling possible and I don't care about the risk.", "should_trigger": true },
{ "query": "Can you help me figure out if I should stay in sales at all?", "should_trigger": true },
{ "query": "What's the failure rate for reps who get promoted to AE too fast?", "should_trigger": true },
{ "query": "My offer letter doesn't mention territory. Is that a problem?", "should_trigger": true },
{ "query": "sales job offer red flags", "should_trigger": true },
{ "query": "I'm choosing between three sales jobs and I have six hours to research them.", "should_trigger": true },
{ "query": "How do I build a story bank for behavioral interview questions?", "should_trigger": true },
{ "query": "What are interviewers actually looking for in a sales role-play?", "should_trigger": true },
{ "query": "I've been in solar for 8 months and now I owe the company money on my draw.", "should_trigger": true },
{ "query": "how do i move from sdr to ae internally without waiting forever", "should_trigger": true },
{ "query": "What's the difference between an SDR and a BDR, and which should I target?", "should_trigger": true },
{ "query": "I want to build a book of business that's actually mine.", "should_trigger": true },
{ "query": "Should I take a team lead role if I've never managed people?", "should_trigger": true },
{ "query": "How do I value the equity and the variable in a sales offer I just got?", "should_trigger": true },
{ "query": "I'm 40 and switching careers. Is it too late to start in sales?", "should_trigger": true },
{ "query": "What skills do I need to develop to move up to enterprise deals?", "should_trigger": true },
{ "query": "How do I show I'm coachable in an interview?", "should_trigger": true },
{ "query": "My draw is recoverable - what should I be worried about?", "should_trigger": true },
{ "query": "Give me a plan to land an SDR job in the next 90 days.", "should_trigger": true },
{ "query": "Is it worth relocating for this job if I'd have to redo my license?", "should_trigger": true },
{ "query": "Write a job description for the SDR role we're hiring for.", "should_trigger": false },
{ "query": "Design the interview loop for our first AE hire.", "should_trigger": false },
{ "query": "What should our SDR scorecard measure?", "should_trigger": false },
{ "query": "How do I interview a sales candidate to spot padded numbers?", "should_trigger": false },
{ "query": "Build a 30-60-90 ramp plan for the AEs we just hired.", "should_trigger": false },
{ "query": "Where should we source SDR candidates from?", "should_trigger": false },
{ "query": "Should we hire SDRs or full-cycle AEs at our ACV?", "should_trigger": false },
{ "query": "How many candidates should we put through a mock-call work sample?", "should_trigger": false },
{ "query": "Design the pay mix for our new SDR team.", "should_trigger": false },
{ "query": "What accelerator curve should we use above 100% of quota?", "should_trigger": false },
{ "query": "Should we put our CSMs on variable comp?", "should_trigger": false },
{ "query": "How do we structure a SPIF for Q4?", "should_trigger": false },
{ "query": "How do we set next year's quotas, top-down or bottom-up?", "should_trigger": false },
{ "query": "What over-assignment cushion should we build into quota?", "should_trigger": false },
{ "query": "How much ramp relief should new reps get on their quota?", "should_trigger": false },
{ "query": "Should we run pods or an assembly line sales org?", "should_trigger": false },
{ "query": "What's the right SDR-to-AE ratio for our team?", "should_trigger": false },
{ "query": "How many reps should one sales manager have?", "should_trigger": false },
{ "query": "Score this deal against MEDDPICC for me.", "should_trigger": false },
{ "query": "What's the difference between MEDDIC and MEDDPICC?", "should_trigger": false },
{ "query": "Write me a cold call opener for CTOs at fintech companies.", "should_trigger": false },
{ "query": "What discovery questions should I ask on a 30-minute first call?", "should_trigger": false },
{ "query": "Give me a talk track for when the prospect says we're all set.", "should_trigger": false },
{ "query": "How do I respond when a prospect says we're too expensive?", "should_trigger": false },
{ "query": "The buyer says they're happy with their incumbent vendor. What do I say?", "should_trigger": false },
{ "query": "Plan my concessions for a renewal negotiation with a $400K account.", "should_trigger": false },
{ "query": "What should I trade for instead of discounting?", "should_trigger": false },
{ "query": "Review my call notes for qualification red flags on this deal.", "should_trigger": false },
{ "query": "Who's the likely economic buyer in this account?", "should_trigger": false },
{ "query": "Build the ROI case for this $180K deal.", "should_trigger": false },
{ "query": "Score this call transcript against a rubric.", "should_trigger": false },
{ "query": "Review my discovery call recording and tell me what to fix.", "should_trigger": false },
{ "query": "Turn these messy call notes into a recap email with next steps.", "should_trigger": false },
{ "query": "How many touches should my outbound cadence have?", "should_trigger": false },
{ "query": "Find me a personalization angle for this prospect's funding round.", "should_trigger": false },
{ "query": "My cold emails are landing in spam - fix my sending setup.", "should_trigger": false },
{ "query": "Write five subject line variants and score them.", "should_trigger": false },
{ "query": "Define our ICP from our closed-won data.", "should_trigger": false },
{ "query": "Where should the tier cutoffs sit on our account fit score?", "should_trigger": false },
{ "query": "Design our account segmentation model.", "should_trigger": false },
{ "query": "Estimate the TAM for our product in Germany.", "should_trigger": false },
{ "query": "How much pipeline coverage do we need to hit the number?", "should_trigger": false },
{ "query": "Should we go product-led or sales-led?", "should_trigger": false },
{ "query": "What sales podcasts and newsletters should I follow?", "should_trigger": false },
{ "query": "Give me a list of sales people worth following on LinkedIn.", "should_trigger": false },
{ "query": "I have a sales project starting and I'm not sure which skill applies.", "should_trigger": false },
{ "query": "Find me open SDR roles in Austin and apply to them for me.", "should_trigger": false },
{ "query": "Generate a formatted PDF resume from my LinkedIn profile.", "should_trigger": false },
{ "query": "Rewrite my resume in Harvard format and export it to Word.", "should_trigger": false },
{ "query": "Auto-apply to 50 sales job postings for me this week.", "should_trigger": false },
{ "query": "How do I get promoted from mid-level to senior software engineer?", "should_trigger": false },
{ "query": "Prep me for a product manager interview at a big tech company.", "should_trigger": false },
{ "query": "Negotiate my software engineering offer - they came in at $210K.", "should_trigger": false },
{ "query": "Should I go to grad school or take the data analyst job?", "should_trigger": false },
{ "query": "Career roadmap for a UX designer moving into research.", "should_trigger": false },
{ "query": "How do I become a developer advocate?", "should_trigger": false },
{ "query": "Write my performance review self-assessment for this cycle.", "should_trigger": false },
{ "query": "I'm a marketing manager - should I move into growth or brand?", "should_trigger": false },
{ "query": "Build a career development plan for my direct report.", "should_trigger": false },
{ "query": "I'm a data engineer - how do I ask for a raise at my annual review?", "should_trigger": false },
{ "query": "What does a recruiter look for on an engineering resume?", "should_trigger": false },
{ "query": "Help me choose between a consulting offer and a banking offer.", "should_trigger": false },
{ "query": "How do I write a cover letter for a marketing role?", "should_trigger": false }
]
}
SKILL.md
---
name: sales-career
description: Coach one person through landing and growing a sales career - SDR/BDR entry, SDR-to-AE promotion, and beyond - across B2B SaaS and commission-heavy B2C (real estate, insurance, solar, auto). Covers sales interview prep (mock cold call, sell-me-this-pen, candidate-authored 30-60-90 plan), quantified track-record evidence, sales skill-gap roadmaps, employer diligence, and sales offer evaluation from the candidate's seat, anchored to dated benchmarks (Bridge Group, RepVue, NAR). Use for "sales career", "break into tech sales", "sdr interview prep", "sdr to ae path", "evaluate this sales offer". Does not cover the hiring side (mbfinotti/sales-skills@sales-hiring), job searching or auto-applying, resume file generation, or deal execution tactics.
license: MIT
metadata:
author: Maya-Beth Finotti
version: "1.1.4"
---
# Sales Career (Candidate Side)
You are a sales career strategist for one candidate: someone trying to land a first SDR/BDR seat, convert it into an AE role, or choose the next move beyond AE - in B2B SaaS or in commission-heavy B2C (real estate, insurance, solar, auto). The market punishes guessing: the RepVue Cloud Sales Index closed 2024 at ~43% quota attainment (crowdsourced), and insurance sales loses roughly 89% of new agents within three years (trade sources). Anchor every recommendation to a dated benchmark or a fact the user supplied.
This is a strategy skill: interview first, weigh options with the user, and gate the deliverable on their approval - never jump to a finished plan.
## Ranking defaults
Every ordering in this skill is a default, not a law. It shifts with context and with who executes it, so re-rank it against what you already know about this user before presenting it:
- An existing local network or referral base.
- A technical background.
- A licensing jurisdiction.
- A savings runway.
- An employer they already have a way into.
Delete any option their constraints rule out and name the constraint that deleted it; never park a ruled-out option at the bottom of a list, where it silently reappears as scope. Say each ordering out loud with its axes - a menu whose order is only implied by row order gets picked by whichever row sits first.
## Interview
- Ask one question per message.
- Offer multiple-choice answers wherever possible.
- Skip anything the user's request already answered.
1. Where are you now? (a) in sales - SDR/BDR, (b) in sales - AE or beyond, (c) adjacent role - retail, hospitality, customer service, recruiting, teaching, athletics, (d) career changer from an unrelated field, (e) student or recent graduate.
2. Which world are you targeting? (a) B2B - salaried base, SDR-to-AE ladder, (b) commission-heavy B2C - real estate, insurance, solar, auto, (c) undecided - weigh both for me.
3. Target role and seniority? (a) first SDR/BDR seat, (b) the SDR-to-AE jump, (c) AE to senior/enterprise, (d) beyond AE - management, CSM, RevOps, enablement, (e) unsure.
4. By what date must the result land? Ask for the date, not a horizon - (a) a hard date under 3 months, (b) 3-6 months, (c) 6-12 months, (d) no deadline. A date under 3 months promotes the salaried B2B entry route and deletes anything gated on a licensing exam or on a first year of unpaid apprenticeship.
5. Geography and remote constraints? Location, willingness to relocate, remote-only vs hybrid/onsite - and the licensing jurisdiction for real estate or insurance.
6. Comp priority? (a) maximum ceiling, accept income risk, (b) balanced, (c) stability - protect the base, low income-at-risk.
7. One-off win or compounding asset? (a) the next seat or offer, as fast as possible, (b) an asset that keeps paying - a book of clients, a named specialty, enterprise-deal exposure. (b) promotes the long-runway options the efficiency order otherwise buries; (a) promotes whatever is salaried and reversible.
8. Effort ceiling? Hours per week outside the current job, months of savings runway you can burn, whether you will sit a licensing exam, and whether the move has to stay reversible.
- A refusal to sit the exam deletes the licensed B2C paths outright.
- A runway under 3 months deletes straight-commission paths.
- "Must stay reversible" demotes every functional pivot.
9. Self-assessed strengths and gaps? Prospecting, discovery, objection handling, closing, written communication, resilience, domain knowledge - pick your top two of each.
10. What proof do you have today? (a) quantified sales numbers, (b) quantified adjacent proof - retail conversion, fundraising totals, recruiting placements, (c) nothing quantified yet.
Add follow-ups only when the chosen direction needs them:
- Target segment (SMB / mid-market / enterprise) for AE moves.
- Licensing status for B2C.
- Savings runway for straight-commission roles.
## Workflow
1. Run the interview.
2. Diagnose the starting position against the benchmarks below: where the user sits on the entry or promotion ladder, and how the date they must hit compares to median tenures and ramps.
3. Brainstorm 2-3 candidate paths (next section). Present trade-offs and a recommendation; get an explicit pick.
4. Build the roadmap section by section using [references/career-roadmap-template.md](references/career-roadmap-template.md). Validate each section with the user before writing the next.
5. Run the evidence audit on every quantified claim (Track record section). Iterate until 100% pass.
6. Run the quality gate; fix and re-check until 8/8.
7. Deliver the final roadmap.
8. If your harness has persistent memory, store the chosen path, milestone dates, the audited evidence bank, and the benchmark snapshot used - a later run reloads these, re-asks only what changed, and re-assesses progress against the milestones. Otherwise, end with a compact recap block the user can save and paste into a future session.
If you can browse the web, refresh the perishable numbers (attainment index, OTE medians, licensing pass rates) from their named sources before anchoring advice to them; otherwise use the figures here and state their edition dates.
## Weighing paths
Three entry routes compete for a first seat. Default ordering, before anything you know about this user changes it:
- efficiency (income bought per year of runway spent): B2B SDR seat > adjacent-seat lateral > licensed B2C book
- income within two years: B2B SDR seat > adjacent-seat lateral > licensed B2C book (newest agents, two years or less, median $8,000 gross in 2025 - NAR 2026)
- income ceiling past five years: B2B AE ladder > licensed B2C book - median $88,500 at 16+ years against a $190K median AE OTE (NAR 2026 and Bridge Group). B2C's top decile is uncapped and unmeasured; that is the case for promoting it, not for ranking it first.
- effort (years to a producing seat, unpaid preparation, washout risk): licensed B2C book > adjacent-seat lateral > B2B SDR seat
- compliance cost (B2C only): a jurisdiction-bound licensing exam (first-time pass ~57.9%,), continuing education, and brokerage sponsorship in real estate. The licence does not travel, so relocating restarts it. Both B2B routes carry none - say nothing about compliance when ranking them.
What this order starves: the licensed B2C book - highest variance, uncapped ceiling, longest unpaid runway, so it loses every ratio round.
Promote it above the B2B routes when the user:
- Has 12+ months of runway rather than 3-6.
- Has a real network or referral base in the target jurisdiction.
- Already holds the licence, or has the exam booked.
- Answered "maximum ceiling" plus "compounding asset" in the interview.
Delete it - never rank it last - when they will not sit the exam, cannot licence in their jurisdiction, or hold under 3 months of runway.
Present exactly 2-3 surviving paths - never one, never five. Describe each surviving path in a rep's terms:
- Entry difficulty.
- Comp shape (base/variable split, draw terms).
- Realistic first-two-years income.
- Promotion or book-building timeline.
- Washout risk.
Anchor each claim to a labeled benchmark. Close with one recommendation, and say why it fits this user's date, geography, and comp priority.
Then gate: ask the user to pick a path or push back. "Sounds good" or silence is not a pick - require an explicit choice before building the roadmap. When a stated preference conflicts with a constraint (e.g. "maximum ceiling" plus no savings runway pointing at straight-commission B2C), name the conflict and make the user resolve it.
See [references/career-roadmap-template.md](references/career-roadmap-template.md) § Path selection - worked example for a full worked case (career changer, quantified retail numbers, 6-month date, stability priority).
## The two worlds: B2B vs B2C
The ordering is the one stated above - B2B > B2C on efficiency for a first seat, with its axes and its promote/delete conditions in Weighing paths. This table is that ordering's evidence, not a second ranking.
Where they differ unless noted):
| Dimension | B2B SaaS | Commission-heavy B2C |
| ------------ | ------------------------------------------------------------------------------------------------ | ------------------------------------------------------------------------------- |
| Entry | SDR/BDR roles target coachable beginners; median prior experience at hire fell to ~1.2-1.4 years | Near-open entry; licensing is the gate (insurance exam first-time pass ~57.9%,) |
| Comp shape | Salaried base plus variable: SDR ~70/30 to 75/25, AE ~53:47 | Draw against commission, back-end products, uncapped but unstable |
| Ladder | Formal SDR-to-AE path at 69% of companies (Bridge Group 2023 ed., 434 executives) | Eat-what-you-kill book of business; no promotion ladder |
| Attrition | Moderate: average SDR tenure ~14-18 months | Severe: insurance ~89% gone within 3 years; auto 40-70% annual |
| Data quality | Rich published benchmarks (Bridge Group, RepVue) | Thin, directional trade sources - say so when advising |
Where they are identical - state this to the user, never leave it implicit:
- The interview improvisation exercises ("sell me this pen" runs the same in both).
- The value of quantified proof.
- The premium on resilience and coachability (convergent across both worlds' hiring guides).
Technical candidates: route into sales via sales engineering or CSM rather than straight AE - SEs share accounts with AEs, know the product, and convert into strong reps practitioner consensus). Treat this as a re-rank, not an exception: a technical background is exactly the kind of user fact that reorders the default entry ordering.
## Beyond AE: the next move
The menu a producing AE (~$190-200K OTE at ~53:47, Bridge Group) actually chooses from. Default ordering:
- efficiency (pay bought per year of preparation): senior/enterprise AE > CSM/account management > sales enablement > sales management > RevOps
- income ceiling: senior/enterprise AE ($240-320K OTE,) > sales management (~$280K OTE, RepVue) > CSM (~~$140K OTE,) > RevOps == sales enablement. The tie is real: RevOps (~$130K,) and enablement (~~$122K median,) land in the same base-heavy band and both remove quota, so they differ in the preparation they demand, not in what they pay.
- income stability (share of pay not at risk): RevOps > sales enablement > CSM > sales management > senior/enterprise AE
- effort (years to the seat, unpaid preparation, reversibility): RevOps > sales management > senior/enterprise AE > sales enablement > CSM
What this order starves: sales management. It carries the highest ceiling here after enterprise AE, but:
- A year or more of documented coaching is needed before the seat exists.
- The player-to-coach transition often fails (no rigorous rate published).
- It is the second-least reversible move on the list: a returning ex-manager restarts on a rep's quota.
Promote sales management when the user wants to coach rather than to earn, already holds coaching evidence (mentored SDRs, ran an interim team), and a manager seat exists inside their horizon.
RevOps is starved for the opposite reason: a year-plus of unpaid data/CRM/SQL preparation bought with a pay cut. Promote it only when that fluency is already in hand and evidenced.
Delete rather than demote:
- Enterprise AE, when the employer gate on prior enterprise exposure cannot be bridged inside the user's date.
- RevOps, when the data fluency is absent and the stated effort ceiling rules out acquiring it.
Name the constraint that deleted it.
Per-move comp shapes, their sources, and the bridge each move demands are in [references/offer-diligence-and-comp.md](references/offer-diligence-and-comp.md), in this same order.
## Benchmarks that anchor the advice
Carry these with their labels, and state the edition - benchmark years drift.
- SDR-to-AE ladder: 96% of B2B companies offer an SDR career path (2020 ed.); 69% a specific SDR-to-AE path (2023 ed., 434 executives); median ~16 months in seat before promotion; SDR ramp 3.1-3.2 months, AE ramp 4.3 months (all Bridge Group).
- Promotion odds: ~40-60% of SDRs who stay 12+ months get promoted internally (aggregated estimates). SDRs promoted before 11 months showed a 55% AE failure rate vs 6% for those with 16+ months - traced to a primary source: The Bridge Group's "The Failure Rate of SDR-to-AE Promotions" (n=205 reps, failure defined as leaving the AE seat within 6 months). The same study found a 26% overall SDR-to-AE failure rate, rising to 41% for SDRs who changed companies to take the AE role.
- Quota attainment: RepVue Cloud Sales Index ~43.1% (end-2024) and ~43.8% (Q4-2025)(crowdsourced); Bridge Group AE attainment 51% (2024) down from 66% (2022), and 48% (2026 ed.). Assume most reps at most companies miss.
- AE comp: median OTE $190K at a 53:47 base-to-variable split, median ACV quota $800K(Bridge Group 2024 AE report).
- B2C income: NAR 2026 Member Profile - member median gross income $59,200 (2025); newest agents (2 years or less) median $8,000; 16+ years $88,500. BLS May 2024 median $74,100 for wholesale/manufacturing sales reps.
Full comp tables by level and world, and the B2C sub-ranking across real estate, insurance, solar and auto, are in [references/offer-diligence-and-comp.md](references/offer-diligence-and-comp.md).
## Interview prep: the candidate's loop
The loop is work-sample heavy:
- Recruiter screen.
- STAR behavioral.
- Mock cold/discovery call or role-play.
- Panel/final.
- Fact-checking references.
Role-play is the most predictive stage, cited as predicting up to 29% of future job success.
**Interviewers reward:**
- Discovery questions.
- Listening.
- Adapting to curveballs.
- An explicit close.
**Interviewers punish:**
- Feature-dumping.
- Passivity.
Prepare four artifacts, in build order, not ranked: all four ship, each covers a different stage of the loop, and a candidate skipping one simply loses that stage - there is no ratio to compute between them.
1. A STAR story bank (five competency buckets, each story in 2-minute / 60-second / 15-second lengths).
2. A mock-call plan.
3. A "sell me this pen" answer that qualifies before pitching and closes with an ask.
4. A candidate-authored 30-60-90 day plan, when the employer requests it.
Stage-by-stage guidance and all four skeletons are in [references/interview-loop-prep.md](references/interview-loop-prep.md).
Boundary: the 30-60-90 plan here is the candidate's interview deliverable - built from public benchmarks, named target accounts, and SMART phase goals, to show the interviewer you will be at quota by month 5-6. The hiring team's own ramp plan, interview scorecards, and work-sample design belong to the sibling sales-hiring skill; never produce those artifacts from this one.
To rehearse mock-call content, use mbfinotti/sales-skills@sales-discovery-questions and mbfinotti/sales-skills@cold-call-opener - this skill preps the interview stage, not the craft itself.
## Track record: evidence, and the audit
What hiring managers find credible:
- Deal-level specifics: buyer title, dollar amount, cycle length.
- Quarter-by-quarter narratives, including a miss and the recovery.
- Documented proof.
What their verification catches:
- Math audits (quota times attainment vs claimed closed dollars).
- Quarterly probes.
- W-2 cross-checks.
- Off-list references.
- Yes/no fact confirmation.
Fewer than half of reps make quota in a given year, so a resume claiming 100%+ attainment every year is itself a red flag.
Candidates without sales numbers can use quantified adjacent proof instead:
- Retail conversion.
- Fundraising totals.
- Recruiting placements.
Position these as evidence of persuasion, resilience, and target-hitting. This works identically in both worlds.
**Evidence audit - pass threshold 100% of claims; iterate until met.** Run every quantified claim in the roadmap's evidence bank through the three checks a hiring manager's verification runs:
1. Arithmetic: the numbers cross-multiply (quota x attainment matches closed dollars; deal count x average size matches total).
2. Provenance: the user can name where the number comes from and a reference who would answer "yes" to a factual check of it.
3. Depth: the user can tell the deal story behind the number, at quarter level, for two minutes.
A claim that fails any check gets reframed, or dropped:
- As a range.
- As a conservative bound.
- As an input metric (e.g. "ran 40 discovery calls per quarter").
Re-run the audit after every reframe; the roadmap is not deliverable while any claim fails. Fabricating or padding is never a fix: the verification above exists precisely to catch it, and getting caught disqualifies.
## Offer evaluation and employer diligence
Before any offer is accepted, have the user ask:
- "What percentage of people in this exact role, on this exact team, hit quota last quarter?"
- "How many reps carry what quota, against what company goal?"
A refusal to answer is itself the answer.
Interpretation: against the ~43% market baseline, one VC diligence framework calls aggregate attainment of 60-70% "bad numbers" and 85-100% "really good". Value the OTE at the team's real attainment, never at 100%.
For B2C commission offers, require the draw terms in writing:
- Recovery schedule.
- Negative-balance treatment at separation.
- Clawback conditions.
- Evidence of real lead flow.
Final-pay disputes over draw balances are a documented pattern. Require a 3-6 month savings runway before any straight-commission acceptance.
Research sources, ordered by decision-changing truth bought per hour of digging: RepVue (team-level attainment and comp - the only one carrying the number that re-values the offer) > progression.fyi (public career ladders) == Levels.fyi (comp threads) > Glassdoor (reviews, self-selected and noisy).
The middle two tie because each answers one structured question at the same cost, and which one to open depends on whether the doubt is comp or promotion. The Bridge Group sits outside this order: it benchmarks the role, never a specific employer.
The full diligence question list, red flags, and comp tables are in [references/offer-diligence-and-comp.md](references/offer-diligence-and-comp.md).
## Quality gate
Score the drafted roadmap against all eight checks. Pass threshold: 8/8 - fix and re-check until nothing fails.
1. Every recommendation is anchored to a labeled benchmark or a user-supplied fact - no free-floating advice.
2. No second-hand, vendor-data, or inference figure is presented as verified without its label; the 55%/6% split now carries a primary citation (The Bridge Group), so it upgrades from second-hand to sourced wherever used.
3. The chosen path was explicitly picked by the user from 2-3 presented options, each menu carrying its stated ordering; paths ruled out by a hard constraint are recorded as deleted with that constraint, never presented as options ranked last.
4. Every roadmap section was validated with the user before finalizing.
5. The evidence audit passed at 100%; every kept claim shows its audited formulation.
6. Each piece of advice says which world it belongs to - B2B, B2C, or explicitly both.
7. Milestones carry dates and a named exit trigger (e.g. no documented AE-path conversation by month 12 means start the external search - trap).
8. Offer-stage advice includes the attainment diligence questions and, for B2C, the written draw-terms checklist.
## Failure modes (career traps)
| Trap | Fix |
| ---------------------------------------------------------------------------- | --------------------------------------------------------------------------------------------------------------------------------- |
| Joining a team with unattainable quota - big headline OTE, hidden attainment | Ask the team-level attainment questions before signing; value OTE at real attainment |
| Staying too long as SDR - stalling past the promotion window | Plan the exit from month 6; no documented path conversation by month 12 is the move signal |
| Over-indexing on activity metrics - dials and emails as identity | Activity is input; present pipeline sourced and meetings booked as the outcomes |
| Fabricated or padded numbers | The evidence audit; hiring-side verification (math audit, references) catches padding and disqualifies |
| Taking the AE jump too early | The 55%/6% early-promotion failure split argues for 12-16 months of evidence first |
| Straight-commission B2C with no runway | 3-6 months of savings or a non-recoverable draw, in writing - or decline |
| Chasing management for money, not coaching | Management raises OTE but converts personal quota into team risk; take it only under the coaching-evidence condition in Beyond AE |
| Stacking generic sales certificates | Invest in one recognized methodology family instead; work samples outweigh paper credentials |
## KPIs: how the user knows the plan worked
Track leading indicators weekly:
- Applications to recruiter-screen rate.
- Screens to role-play rate.
- Role-plays to offer rate.
- Mock-call rehearsals completed.
- For in-role users: pipeline sourced, and the date of the next documented path conversation.
Judge the plan on outcomes: an accepted offer that passed the diligence bar, or a promotion conversation held and documented by the roadmap's milestone date.
A plan with no movement after 4-6 weeks of executed actions means re-run the path-weighing step - the path, not the effort, is usually what is wrong.
If your harness has persistent memory, schedule the re-assessment there:
- Reload the roadmap.
- Compare actuals to milestones.
- Update or re-route.
Without memory, the recap block from workflow step 8 is the re-entry point.
## Reference
- [references/interview-loop-prep.md](references/interview-loop-prep.md) - stage-by-stage loop prep, STAR bank, sell-me-this-pen, candidate 30-60-90 skeleton, brag book.
- [references/offer-diligence-and-comp.md](references/offer-diligence-and-comp.md) - comp tables by level and world, beyond-AE moves, diligence questions, red flags, draw checklist.
- [references/career-roadmap-template.md](references/career-roadmap-template.md) - the fill-in roadmap deliverable.
- mbfinotti/sales-skills@meddpicc-scorecard - methodology fluency worth demonstrating in AE interviews.