Questions to Ask Chief Revenue Officer
Questions for a salesperson or sales leader interviewing with the CRO they would report to, covering quota attainment, how commission actually pays out, territory, pipeline and who has left recently.
The questions
Open any question for the note
What proportion of the team hit quota last year?
Why ask it
The first number to ask for and the one that frames everything else. If a third of the team made target, quotas are set for the board rather than for the sellers, and your own plan will be similarly unreachable. A refusal to give the figure is itself a figure.
Who hit it, and what did they have that the others did not?
Why ask it
Follows directly from the first answer. If the same two people succeed every year because they hold the inherited accounts, the model is territory rather than talent, and you need to know which territory you are being offered.
How many people have held this seat in the past two years?
Why ask it
Three predecessors in twenty-four months means the patch does not work, whatever the reason given for each departure. Ask what happened to each of them, and whether their accounts were redistributed or left to go cold.
Can you walk me through the commission plan with real numbers?
Why ask it
Ask for a worked example at target and at seventy per cent, including when it pays. Accelerators, caps, clawbacks and quarterly resets change earnings enormously, and the summary in the offer letter rarely shows the effect of missing by a little.
When does commission actually land, and what can stop it?
Why ask it
Payment on invoice, on collection, or on customer go-live are very different arrangements. Ask what happens if a customer pays late or churns in month four, and whether anyone on the team has had commission reversed.
What is the average deal size and sales cycle, and how do you know?
Why ask it
Ask whether the figures come from closed business or from the pipeline as forecast. Averages skewed by one large deal are common. A CRO who volunteers the median as well as the mean is being straight with you.
Where does pipeline come from, and how much of it do I have to build myself?
Why ask it
The single biggest determinant of whether the job is achievable. Ask for the split between inbound, outbound and partner sourced. Being told marketing supplies leads is worth checking against what the marketing team says it delivers.
What would my territory be, and who had it before?
Why ask it
Ask whether it is new, inherited, or carved out of someone else's. Carved-out patches create resentment and often exclude the accounts that were actually going to close. Ask what is in it today by name and value.
How was quota set for next year?
Why ask it
Built up from territory potential, or handed down from a growth number the board wants. The second is much more common and produces targets nobody can model. Ask whether ramp is built in for someone new, and how long that ramp is.
Why do you lose deals, and who do you lose them to?
Why ask it
Answers about price usually mean the value case is not landing, since price objections tend to be the symptom rather than the cause. A CRO who names a specific competitor and a specific weakness has done win-loss analysis. A vague answer means nobody asks.
What does churn look like, and does it affect my commission?
Why ask it
Selling into a leaky product means the same accounts get resold every year and net growth stalls, which eventually hits quotas and headcount. Ask for the renewal rate, and whether early churn on your deals comes back to you.
How much discounting is normal, and who approves it?
Why ask it
Heavy routine discounting tells you the list price is fictional and the negotiation happens internally. Ask what the average discount was last year and how many approvals a standard deal needs, since that determines how long your quarter-end really takes.
What does your forecast process look like, and how accurate was it?
Why ask it
Ask how last quarter's early forecast compared to what closed. A CRO who knows the variance and can explain it runs a disciplined operation. Where forecasts are set by whatever the board expects, sellers spend their weeks defending numbers instead of selling.
What support would I have: engineers, marketing, anyone doing outbound?
Why ask it
The same quota is a different job with a solutions engineer than without one. Ask about the ratio, and whether those people are shared across regions, which usually means they are unavailable at the moment you need them most.
Which tools would I be expected to use, and how much time does that take?
Why ask it
Sellers commonly lose a day a week to administration and reporting. Ask what is mandatory and what a manager actually inspects. A long list with heavy inspection means less selling time against the same target.
What happens to someone who misses two quarters in a row?
Why ask it
Ask for the process and a recent example. Whether the answer is coaching with a defined plan or a quick exit tells you how much room you have while ramping, and how honest the earlier answers about support were.
How do you and the marketing leader disagree about lead quality?
Why ask it
This argument happens everywhere. What matters is whether there is a shared definition and a forum for it, or whether sellers privately ignore what marketing sends. The second wastes a quarter of the spend on both sides.
What do you personally do in a deal?
Why ask it
Some CROs still take a seat at the table; others manage through a spreadsheet. Neither is wrong, but it determines whether you get real help on a difficult deal or a request for an update. Ask when they last joined a customer call.
What is the least honest thing our sellers are saying to customers?
Why ask it
A direct question and the reaction is informative. A CRO who names a specific overstatement, about a roadmap item or an integration, and says how it is being handled, is running something you can work inside. Denial is worth taking as a warning.
What would make you leave?
Why ask it
Their answer names the conditions under which this becomes a bad job for you as well: a board losing patience, a product not shipping, a target nobody believes. It also tells you how candid they are prepared to be at the end of an interview.
Working out whether the number is achievable
Practical guidance for the conversation itself
Before the conversation
Work out what has to be true
Take the quota, divide by a realistic average deal size, and multiply by a plausible win rate. That gives you the number of qualified opportunities the year requires. Bring that arithmetic and ask where those opportunities are coming from.
Find people who have left
Former sellers from the team are usually findable and often willing to talk. Ask them about attainment, pipeline and whether commission paid as described. This is the most reliable diligence available to you.
Read the funding and product news
A recent raise, a missed release, or a round of layoffs all change what next year's target will be. Ask about a specific item you found rather than in general terms.
Ask for the plan document
Request the actual compensation plan and quota letter before you accept anything. Verbal descriptions of accelerators and clawbacks are consistently more generous than the written terms.
Reading the answers
Encouraging signs
- Gives attainment as a percentage without being pressed for it
- Knows last quarter's forecast variance and why it was off
- Can name why deals are lost, with a competitor attached
- Describes ramp and what happens during it in concrete terms
Worth pressing on
- Attainment described as strong without a figure
- Pipeline promised from marketing with no numbers behind it
- A territory that has had several holders in quick succession
- Commission explained only at target, never at seventy per cent
Mistakes candidates make
Being sold to instead of buying
A CRO interview is conducted by someone who closes for a living, so the enthusiasm in the room is not evidence. Keep returning to the numbers, politely, until you have them.
Negotiating base and ignoring the plan
Ten thousand more on salary matters far less than an accelerator that starts at a hundred per cent rather than eighty, or commission paid on collection rather than on signature. Read the mechanics before arguing about the base.
Not asking what happened to your predecessor
It is an awkward question and one of the most informative. Territories with rapid turnover rarely improve on their own, and the reason given for each exit is usually incomplete.
Taking the pipeline report at face value
Ask how a deal is qualified into the pipeline and who checks. Where anything with a meeting attached counts, the reported pipeline may be several times the real one, and your target was built on it.