I applied online. The process took 2 weeks. I interviewed at HubSpot (Cambridge, MA) in June 2019
Interview
Four interviews. Three over the phone and a series in person. Extremely hypothetical questions such as (I made this up, but just as ludicrous): "If you were a lawnmower, describe a time you had encountered some grass that was against the grain of the way you were mowing and how you overcame that on a Tuesday."
OR
"Tell us about a time where you designed a submarine and the seven stages of accomplishment that was recognized from sub-senior management."
Then they tell you how terrible you did and how you scored poorly because no one has any clue how to answer these questions. They even provide you with study material that says HubSpot does NOT want to hire people who use any sort of instinct. They want people who fit into a preconceived mold. They want robots.
I have a lifetime quota achievement of 140% in SaaS sales and was told I wasn't offered a position because I don't listen to feedback. So either that's BS, or I'm the greatest, most natural salesperson of all time since that means I accomplished this with no coaching whatsoever.
I was warned by friends who left HubSpot not to go. Now I know why.
Interview questions [1]
Question 1
They had an impromptu mock call where I was supposed to sell a product from a previous company from several years ago. I didn't know this was going to happen. It was a sabotage.
Phone Screen with Recruiter (off-camera)
Interview with Manager (mock disco)
Interview with another Manager (mock solution presentation)
Interview with your Sales Director (pretty easy, be human, we talked about fishing)
The two managers you get can make or break you getting in as some are tougher than others.
Multiple meetings and material to review for your interview stages. Be prepared to take 5 hours out of your work day to join the interview prep calls and meetings. Total time dedicated to interviews and preparation time roughly 10 hours.
I applied online. I interviewed at HubSpot (Dallas, TX) in May 2026
Interview
Very thorough and transparent interview process. Make sure you come well-prepared and can confidently speak to your ability to consistently execute 50+ outbound calls per day. I would also recommend highlighting a structured sales system you’ve successfully used and be prepared to walk through it in detail—from territory mapping and prospect research to outbound outreach, meeting generation, pipeline management, and follow-up cadence. The more you can demonstrate a repeatable, process-driven approach to generating results, the stronger your candidacy will be. Additionally, have specific metrics and success stories ready that showcase how your system has translated into meetings, opportunities, and revenue.