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August 2, 2026 · Louie Bernstein
Most founders interview a VP of Sales the same way they go on a first date.
fractional sales
Most founders interview a VP of Sales the same way they go on a first date.
They want to like the person. They ask broad questions. They leave the room feeling good about someone they have known for forty-five minutes.
Six months and $150,000 later, nothing has changed. Revenue flat. Pipeline still a mess. Team still winging it. And a VP who is very busy, just not doing the things that move the needle.
Here is what I have learned after fifty years on both sides of this conversation.
The interview is the cheapest due diligence you will ever do on a $250K+ hire. Every question you fail to ask costs you real money. Not hypothetical money.
Before you ask anything, know what you are actually hiring for.
There are two kinds of sales leaders. Builders and Drivers.
A Builder creates the machine from scratch. They write the first playbook, configure the CRM from zero, train the first reps. They're comfortable with chaos because they've lived in it.
A Driver optimizes a machine that already exists. They're excellent at scaling what someone else built. Their career has been at companies where the infrastructure was already in place when they arrived.
At $1M–$10M ARR, with no documented process and a founder still closing most deals, you need a Builder. Almost every time.
The problem is that most founders get seduced by the Driver. The polished resume from Salesforce or Oracle, the confident answers, the impressive LinkedIn profile. They hire the logo, not the capability.
Here are the five questions that separate the two, fast.
"Describe the last time you built a sales process completely from scratch: no playbook, no functional CRM, no system."
If they talk about optimizing an existing process, you have your answer.
"Walk me through exactly what you will do in your first 30 days."
A Builder gives you a specific, sequenced plan. A Driver gives you a strategy.
"Have you ever worked at a company under $10M ARR?"
If the answer is no, proceed with real caution. The skills do not transfer the way they think they will.
"Show me a Sales Playbook you personally wrote."
Not contributed to. Wrote. Their reaction to this request will tell you as much as the document itself.
"What do you need from me to succeed and what will you do if you are not getting it?"
A great VP of Sales will ask you to get out of the day-to-day close. They will tell you they will have a hard conversation with you before things go sideways. Anyone who says "just support and buy-in from leadership" does not know what the job actually requires.
One more thing. After the final interview, give the finalist an assignment. Ask them to spend one week interviewing your sales team and come back with a written report. Pay them. No much, just a sign of good faith.
What you see in that report is what your sales team will see every day for the next twelve months.
They want to like the person. They ask broad questions. They leave the room feeling good about someone they have known for forty-five minutes.
Six months and $150,000 later, nothing has changed. Revenue flat. Pipeline still a mess. Team still winging it. And a VP who is very busy, just not doing the things that move the needle.
Here is what I have learned after fifty years on both sides of this conversation.
The interview is the cheapest due diligence you will ever do on a $250K+ hire. Every question you fail to ask costs you real money. Not hypothetical money.
Before you ask anything, know what you are actually hiring for.
There are two kinds of sales leaders. Builders and Drivers.
A Builder creates the machine from scratch. They write the first playbook, configure the CRM from zero, train the first reps. They're comfortable with chaos because they've lived in it.
A Driver optimizes a machine that already exists. They're excellent at scaling what someone else built. Their career has been at companies where the infrastructure was already in place when they arrived.
At $1M–$10M ARR, with no documented process and a founder still closing most deals, you need a Builder. Almost every time.
The problem is that most founders get seduced by the Driver. The polished resume from Salesforce or Oracle, the confident answers, the impressive LinkedIn profile. They hire the logo, not the capability.
Here are the five questions that separate the two, fast.
"Describe the last time you built a sales process completely from scratch: no playbook, no functional CRM, no system."
If they talk about optimizing an existing process, you have your answer.
"Walk me through exactly what you will do in your first 30 days."
A Builder gives you a specific, sequenced plan. A Driver gives you a strategy.
"Have you ever worked at a company under $10M ARR?"
If the answer is no, proceed with real caution. The skills do not transfer the way they think they will.
"Show me a Sales Playbook you personally wrote."
Not contributed to. Wrote. Their reaction to this request will tell you as much as the document itself.
"What do you need from me to succeed and what will you do if you are not getting it?"
A great VP of Sales will ask you to get out of the day-to-day close. They will tell you they will have a hard conversation with you before things go sideways. Anyone who says "just support and buy-in from leadership" does not know what the job actually requires.
One more thing. After the final interview, give the finalist an assignment. Ask them to spend one week interviewing your sales team and come back with a written report. Pay them. No much, just a sign of good faith.
What you see in that report is what your sales team will see every day for the next twelve months.