Questions to Ask Before Accepting a Sales Job
Questions for the stage between a sales offer and a signature, covering the comp plan and where the money really sits, quota attainment across the team, territory and pipeline, when a deal counts, clawbacks, and who you would be reporting to.
20 questions, each with the reason to ask it · includes a conversation guide
The questions
Open any question to see why it works.
- 1
What is the on-target number, and how does it split between base and variable?
The split tells you what kind of job it is. A high base with a small variable is closer to account management, while a thin base with most of the money at risk means the first two quarters are effectively unpaid if the ramp goes badly.
- 2
Can I read the full comp plan document before I sign anything?
The offer letter states the target and the plan states the rules, and the rules are where accelerators, caps, clawbacks and payment timing live. A company that will not show it until day one is asking you to accept terms unseen.
- 3
What percentage of the team hit quota last year?
Ask for the number and how many reps it is out of. Under half is common and tells you the target is aspirational, which means the on-target earnings figure in the offer is a number most people in the role did not earn.
- 4
How many of those reps were in seat for the full year?
This is the follow-up that exposes a flattering statistic. If attainment is measured only across reps who survived, the average quietly excludes everyone who was managed out at month seven, which is the outcome you are trying to assess.
- 5
What is the quota, and how was that number arrived at?
Listen for whether it comes from what the territory has historically produced or from dividing a board target by headcount. The second method is how quotas end up unrelated to what anyone in the seat has ever achieved.
- 6
When does the quota clock start, and what does the ramp look like?
Ask for the ramp in specifics: reduced quota for which months, and guaranteed commission or not. A long sales cycle with a short ramp means you carry a full target before any deal you sourced yourself could possibly close.
- 7
Is there a draw, and is it recoverable?
A recoverable draw is a loan against future commission, so a slow first year can leave you owing money back or working months of deals for nothing. A non-recoverable draw is closer to a guarantee. The difference is everything.
- 8
Is commission capped, and are there accelerators above target?
Caps are the fastest way to demotivate a strong closer, and companies rarely volunteer them. Ask what happens at 120 percent and at 200 percent, and whether anyone has actually been paid at those levels.
- 9
At what point is a deal credited to me: signature, first payment, or revenue recognition?
This decides when you get paid and whether a December close lands in this year's numbers. Payment on cash collected means a slow-paying enterprise customer can push your commission out by a quarter through no fault of yours.
- 10
If a customer churns early or does not pay, does the commission come back?
Ask for the clawback window in months and whether it applies to non-payment only or to cancellation as well. A twelve month clawback on an annual contract means you are underwriting the company's collections and retention risk.
- 11
What territory or book am I taking, and who had it before me?
Inheriting a worked-out patch from someone who just left is very different from a new region. Ask what that person produced, why they are gone, and whether any of their accounts are being carved out before you arrive.
- 12
How much of my pipeline comes from marketing, and how much do I build myself?
Get a percentage rather than an assurance that leads are strong. A role sold as inbound that turns out to be ninety percent cold outreach is a different job, a different skill set, and a much longer ramp than you were told.
- 13
How many people have left this team in the past year, and what happened?
Ask for the count, not the sentiment. Heavy turnover in a sales org usually points at the quota, the product, or the manager, and the interviewer's willingness to name which one is informative on its own.
- 14
Who would I report to, how long have they been here, and how many reps do they carry?
A manager three months into the job cannot yet defend your quota or your deals internally. A manager with twelve direct reports cannot coach any of them, which matters most in your first two quarters.
- 15
Walk me through a deal you won last quarter: cycle length, size, and who signed.
Ask them to describe a real one rather than the ideal customer profile. Vagueness here, or an example from two years ago, usually means the recent deals do not look like the story the company tells about itself.
- 16
What does the product not do, and which deals do you consistently lose?
Every rep needs this on day one and it is rarely offered. An interviewer who can name the competitor that beats them and the use case they should walk away from is describing a company that lets its salespeople be honest.
- 17
What support sits around me: SDR, solutions engineer, deal desk, legal?
The absence of these roles is not automatically bad, but it changes how you spend your week. Without an SDR you prospect; without legal support you negotiate redlines yourself, and both eat the hours you would spend selling.
- 18
What activity is measured weekly, and what happens if the numbers are low but the pipeline is fine?
This exposes the management style more reliably than any question about culture. Some teams look only at pipeline and closed business, and some run daily call counts, and you need to know which one you are joining.
- 19
Can the plan or the territory change mid-year, and has that happened recently?
Most plans allow it, so the useful part is what they have actually done. A territory split after a strong quarter or a mid-year quota raise is a pattern people only discover after it has cost them.
- 20
Could I speak with a rep who joined about a year ago?
Someone a year in has ramped, seen a full comp cycle, and is not yet a company spokesperson. Refusal to arrange this, when you have already met three managers, is the answer to several of the questions above.
Reading a sales offer
Practical guidance for the conversation itself.
Where the money actually is
Where the money actually is
Treat on-target earnings as a hypothesis
It is base plus what you would earn at exactly one hundred percent of quota. If under half the team reaches quota, the typical outcome for the role sits well below the headline, and the base is the only part you can plan your life around.
Read the plan for the four rules that matter
When a deal is credited, when commission is paid, whether it can be taken back, and whether the plan can change mid-year. These four decide your actual income more than the percentage rate does.
Model a slow start honestly
Work out what you take home if you close nothing for two quarters. If that number does not cover your life, the ramp terms and the type of draw are the parts of the offer to negotiate, not the target.
Negotiate the guarantee, not just the base
Guaranteed commission for the ramp period is often easier for a company to approve than a higher base, and it protects exactly the months where a new rep is most exposed.
Judging the seat itself
Judging the seat itself
- Find out whether the role is new headcount or a backfill. A backfill has history you can ask about; new headcount means nobody has ever hit the number you are being given.
- Ask what the last person in this territory produced. If nobody will say, assume it was not good.
- A product that is hard to demo, hard to price, or in the middle of a rebuild will show up in your cycle length long before it shows up in a company update.
- Check whether the accounts you are promised are contractually yours or reassignable at will. Named account lists get reshuffled quietly.
- Ask what happens to your deals if you leave mid-cycle. Plans that pay nothing after your last day change how the final quarter feels.
Signals worth slowing down for
Signals worth slowing down for
- Will not share the comp plan document until after you have resigned elsewhere.
- Cannot or will not state last year's attainment percentage across the whole team.
- Describes the pipeline as strong but cannot say what share is inbound.
- Several people in the same team have left in under a year and it is explained as fit.
- Pressure to sign within forty-eight hours, framed as a sign of how much they want you.
- The hiring manager talks about earnings potential and avoids the base number.