Questions to Ask Before Accepting a Sales Job
Questions to ask about a sales job in the stretch between the offer and your signature, when you can still ask anything and they still want a yes. They run from quota and on-target earnings through the commission rules, territory and leads, the product and its deals, and the manager and team, to the paperwork. All of them are worded the way one rep would ask another, so soften them where the room calls for it.
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The questions
Each question, and why to ask it
Quota and OTE
What are the on-target earnings, and how do they split between base and variable?
Why ask it
The split tells you what kind of job it is. A high base with a small variable is closer to account management. A thin base with most of the money at risk means a slow ramp comes out of your savings, so check that the base alone covers your bills.
What is the quota, and how was that number set?
Why ask it
Listen for whether it comes from what the territory has produced before or from a company target divided by headcount. A number set the second way may have no connection to what anyone in the seat has ever sold.
Can I read the full comp plan document before I sign anything?
Why ask it
The offer letter states the target and the plan states the rules: accelerators, caps, clawbacks and payment timing. A company that will not show it until day one is asking you to accept terms unseen.
When does the quota clock start, and what does the ramp look like?
Why ask it
The details to pin down are which months carry a reduced quota and whether commission is topped up while you build pipeline. A long sales cycle with a short ramp means you carry a full target before any deal you sourced yourself could close.
What percentage of the team hit quota last year?
Why ask it
A percentage means little without the headcount behind it: six reps out of eight and sixty out of eighty are different kinds of evidence. If fewer than half got there, the on-target earnings in your offer describe a year most people in the role did not have.
Does the quota attainment figure include reps who left or joined during the year?
Why ask it
Attainment measured only across the reps who lasted the year leaves out everyone managed out at month seven, and that is the outcome you are trying to judge. A manager who can give you both versions of the number has looked at it honestly.
What did a middle-of-the-pack rep take home last year, all in?
Why ask it
Ask for the median, since one rep with a huge account drags an average far above what a normal year pays. If the only figure anyone can produce is the top earner's, you still do not know what an ordinary year is worth.
What did your best rep earn last year, and what was different about their patch?
Why ask it
The top figure shows whether the ceiling is real. The second half matters more: if the answer is an inherited list of named accounts, you are hearing about a territory, not a method you could copy.
Is quota measured monthly, quarterly or annually, and does a shortfall carry over?
Why ask it
Monthly targets punish one slow month even inside a strong year, while annual ones let a late deal rescue you. A deficit that rolls forward can put you behind before the next period has opened, so find out which system this is.
How has the quota for this seat moved over the last few years?
Why ask it
A number that climbs every January whatever the results means a good year is rewarded with a harder one. The telling detail is what happened to the target of a rep who blew past it.
Commission
Is there a draw, and is it recoverable?
Why ask it
A recoverable draw is an advance against future commission, so after a slow start you can spend months of deals paying it back. A non-recoverable draw is yours to keep. Ask what happens to an unrecovered balance if you leave, because plans and local law differ on it.
Is commission capped, and are there accelerators above target?
Why ask it
A cap means the plan stops paying at the point you are selling most. Ask what the rate is at 120 percent and at 200 percent of quota, and whether anyone was paid at those levels last year.
What is the commission rate, and does it change by product, contract length or discount?
Why ask it
A flat rate is easy to check against a statement. Rates that drop on discounted or short deals are the plan telling you which business the company prizes, and that is easier to learn in this conversation than from your first payment.
At what point is a deal credited to me: signature, first payment, or revenue recognition?
Why ask it
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.
How often is commission paid, and how long after a close does it reach my account?
Why ask it
Monthly payment a few weeks in arrears is easy to budget around. Quarterly payment with a lag can leave a January deal unpaid until late spring, which bites hardest in the first year when savings are covering the ramp.
If a customer cancels early or never pays, do you take the commission back?
Why ask it
The clawback window in months is the first detail, and the second is whether it covers non-payment only or cancellation as well. A twelve month clawback on an annual contract means you are carrying the company's collections and retention risk.
Do I earn anything on renewals, upsells and expansions, or only on new customers?
Why ask it
If the account passes to a customer success team at signature, your income starts again from zero each year. Where reps keep a share of the growth, a good book compounds and the job gets easier with tenure.
How is credit split when an SDR, an overlay rep or a partner is on the deal?
Why ask it
Find out whether credit is duplicated or divided. Divided credit on a product that is always team-sold makes your real quota larger than the one on paper, and arguments over who sourced a deal are settled by whoever wrote the rules.
Are there house accounts or deal types that pay a reduced rate or nothing?
Why ask it
Some plans exclude the largest customers, channel deals or anything a founder brought in. You want those exclusions named before you spend a quarter on an account that turns out to sit outside the plan.
Can the plan or the territory change mid-year, and has that happened recently?
Why ask it
Plans often reserve the company's right to change them, so the useful part is what has actually been done. A territory split after a strong quarter, or a quota raised in July, is history you want to hear now and not after it has cost you.
Will I get a statement showing how each commission payment was worked out?
Why ask it
A deal-by-deal statement lets you spot a missing deal or a wrong rate in minutes. Where payment arrives as one unexplained figure, reps keep their own spreadsheets and argue from memory. Ask who rules on a dispute.
Are there spiffs, contests or a club trip on top of commission, and how many reps qualified last year?
Why ask it
Contests show what leadership is pushing this quarter, and they can vanish by the next one. Leave them out of your sums. If the trip went to the same two people three years running, the best accounts may sit in very few hands.
Territory and leads
What territory or book would I take over, and why is the seat open?
Why ask it
Inheriting a worked-out patch from someone who just left is very different from opening a new region. Find out what the last rep produced, why they are gone, and whether any of their accounts are being carved out before you arrive.
How much of my pipeline comes from marketing, and how much do I build myself?
Why ask it
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.
How many accounts are in the patch, and how many were pitched or sold to in the past two years?
Why ask it
A long list of names proves little. You need to know how many are untouched, how many said no recently and how many are already customers, because a patch that has been worked twice starts slower than its size suggests.
How are inbound leads handed out: round robin, by territory, or to whoever is closing most?
Why ask it
Routing by performance feeds the reps who are already ahead and starves the newest one, which would be you. Round robin or strict territory rules give a new hire the same shot from the first week.
Will I inherit open opportunities, and do they pay full commission if I close them?
Why ask it
An inherited pipeline can carry your first two quarters or be a graveyard nobody tidied up. Ask to see it with last-activity dates, and confirm that a deal someone else opened still pays you in full.
Are more reps being hired into this region this year?
Why ask it
Headcount plans decide how thin your patch gets. Several hires into one geography often end in a carve-up, so ask whether quotas came down the last time territories were split.
Which CRM do you use, and how complete are the records on the accounts I would get?
Why ask it
Good notes show who was called, what they said and why the last deal stalled. Blank records mean your first months go on rediscovering what the previous rep already knew. Asking to see one account on screen is a reasonable request at offer stage.
Product and deals
Can you walk me through a deal the team won last quarter: how long it took, what it was worth and who signed?
Why ask it
Hold out for a real one, not the ideal customer profile. Vagueness here, or an example from two years ago, suggests the recent deals do not look like the story the company tells about itself.
How big is a typical deal, and how long does it take from first meeting to signature?
Why ask it
A quota is easier to judge as a count of deals than as a sum of money. Work out how many typical wins it takes, then ask whether a rep starting from an empty pipeline could sign that many once the cycle length and the ramp are taken off the year.
What share of qualified opportunities turn into wins, and how much pipeline does a rep need to cover quota?
Why ask it
A team that closes one deal in five needs five times quota in pipeline, and somebody has to build it. If nobody can state the win rate, forecasting here is done by feel and your target was probably set the same way.
What does the product not do, and which deals do you consistently lose?
Why ask it
You will need this in your first week, and it is seldom volunteered. An interviewer who can name the competitor that beats them and the kind of customer to walk away from is describing a company that lets its salespeople be honest.
What share of customers renew, and what do the ones who leave say on the way out?
Why ask it
You would be selling the product's reputation along with the product. Weak retention reaches a rep as thin references, commission taken back and prospects who have already heard the complaints.
How far can I discount on my own, and who signs off beyond that?
Why ask it
With no authority at all you wait days in every negotiation. With plenty, check whether discounted deals pay a lower rate. Either way, find out how long sign-off takes at quarter end, when every rep is in the queue.
What support would I have around me: an SDR, a solutions engineer, a deal desk, legal?
Why ask it
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.
Manager and team
Who would I report to, how long have they been here, and how many reps do they manage?
Why ask it
A manager three months into the job has little standing yet to defend your quota or your deals internally. One with twelve direct reports has very little time to coach any of them, and coaching matters most in your first two quarters.
How does my manager spend time with reps: joint calls, deal reviews, forecast meetings?
Why ask it
A manager who sits in on calls and works deals alongside you is coaching. One whose only contact is the weekly forecast grilling is inspecting, and you would be learning the job from peers.
How many reps have left this team in the past year, and why?
Why ask it
Get the count before the explanation. Heavy turnover on a sales team usually traces back to the quota, the product or the manager, and whether the interviewer will say which one is informative in itself.
What do the first thirty days look like: training, shadowing, a certification?
Why ask it
A set program with a date for your first live call means someone owns new-hire ramp. Learning by sitting next to whoever is free suits a veteran who knows the market, and it leaves a career changer guessing at the product for months.
What activity is measured weekly, and what happens if the numbers are low but the pipeline is fine?
Why ask it
This shows the management style more reliably than any question about culture. Some teams look only at pipeline and closed business, and some count calls every day, and those are very different places to spend a slow month.
Is the job remote, in the office or out in the field, and how much travel should I expect?
Why ask it
Office days, nights away and whether drive time between customers counts as work all belong in the answer. A territory that looks compact on a map can mean four hours in the car for two meetings, which limits how many accounts you can really cover.
At what point does a rep who is behind go on a performance plan?
Why ask it
Every sales team has a line, and it is better to hear where it sits than to find it. Follow up with how many people came through a plan and stayed, since a plan nobody survives is a notice period under another name.
Where do reps go from this seat, and how long did the most recent promotion take?
Why ask it
Worth asking if you want larger accounts or a team of your own later. Push for a name and a timeline, because talk of room to grow with no example behind it means nobody has made the move yet.
Could I speak with a rep who joined about a year ago?
Why ask it
Someone a year in has ramped, lived through a full comp cycle and is not yet a company spokesperson. Ask them what surprised them about the plan. If the company will not arrange the call, weigh that alongside everything management told you.
Before you sign
What benefits come with the job, and are they worked out on base pay or on total earnings?
Why ask it
Health insurance, a retirement match and paid leave matter in any job. The wrinkle in sales is that some of them may be calculated on base pay alone, which is worth less to a rep on a low base. It depends on the employer and the country, so ask for this plan's rule.
Is quota adjusted for vacation, parental leave or time off sick?
Why ask it
Generous time off means little if the target stays put while you are away. Ask what happened to the number for the last rep who took leave, and who was paid on their accounts in the meantime.
Am I an employee or an independent contractor?
Why ask it
Contractor status generally shifts taxes, insurance and expenses onto you and can remove protections employees have. The rules differ by country and state, so confirm which this is and look up what it means where you live.
Would I have to pay for anything to get started, such as a license, training or leads?
Why ask it
Some fields require a license to sell at all, and who pays for the course and the exam varies by employer. Buying your own leads, a starter kit or a training package is a different matter: find out the cost, whether any of it is refunded, and how long new reps take to earn it back.
Which running costs are mine: car, fuel, phone, travel, client meals?
Why ask it
A field role can cost real money every month, and reimbursement rules differ by employer and by place. Ask about a car allowance or mileage rate, and how long an expense claim takes to be repaid.
If I resign or am let go, what happens to commission on deals I have already closed?
Why ask it
Some plans pay only if you are still employed on the payment date, which can turn a notice period into a pay cut. The law on earned commission differs by state and country, so ask how this plan handles it and check the wording in the document.
Is there a non-compete or non-solicit clause, and can I read it before I accept?
Why ask it
These clauses can limit where you work next and which customers you may call afterwards. Whether they hold up depends heavily on where you live, so read the exact wording and take local advice if it worries you.
Did the company hit its own revenue target last year?
Why ask it
A company that missed tends to make it up with higher quotas, fewer reps or a new plan in the second half. How plainly they answer is also a fair preview of how bad news will reach you once you work there.
If the base is fixed, is there room on the ramp terms, a sign-on bonus or the start date?
Why ask it
A hiring manager may have more freedom on one-off terms than on base pay, which is often tied to a band. Naming three options makes it easy to say yes to one, and the response shows how the company negotiates when the customer is you.
Will the ramp terms, the territory and anything else we agreed go into the offer letter?
Why ask it
A verbal promise from a sales manager lasts as long as that manager does. Once the ramp pay and the account list are in the letter or an email, a reshuffle six months in is much harder to apply to you quietly.
Reading a sales offer
Practical guidance for the conversation itself
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. Between them these four can move your actual income as much as the percentage rate does.
Run the quota through the calendar
Quota divided by the typical deal gives the wins you need, and wins divided by the win rate gives the opportunities. Lay those against the cycle length and the ramp. If the sums ask for more deals than the months allow, the problem is the target, and no amount of effort from you will fix it.
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 ramp, not just the base
A fixed commission payment for the ramp months, or a non-recoverable draw, can be easier for a company to approve than a higher base. It also protects exactly the months when a new rep is most exposed.
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.
- Compare the title with the work. An account executive who books every meeting alone and an account manager who carries a new-business number are both doing two jobs, and the plan should pay for the one that takes the hours.
- 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.
- Ask whether the named accounts you are promised will be written into the offer or can be reassigned whenever territories are redrawn.
- With two offers in hand, compare the base, the share of reps at quota and the ramp terms. Two on-target figures side by side tell you little, because each is built on a different quota.
Who to ask, and when
- You do not need every question here. Pick the ones whose answers would change your decision, and ask for the comp plan document first, since it settles many of the Commission questions on its own.
- Pay questions go to the hiring manager or whoever owns the plan, after the offer and before you resign anywhere. A recruiter often has the headline figure and not the rules behind it.
- Save attainment, lead quality and how the manager behaves in a bad quarter for the rep you are introduced to, then compare the answers with what management told you.
- Put anything from Before you sign in an email, so the reply arrives in writing and can be attached to the offer.
- Ask with curiosity and not as a cross-examination. A good sales manager hears careful questions about quota and territory as proof that you qualify a deal the same way.
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.