I applied online. The process took 4 weeks. I interviewed at Common Wealth Retirement (Toronto, ON) in Dec 2025
Interview
I had a call with the head of Product, met the team, presented my portfolio, and talked about my previous work experiences. The role was to fill a vacancy, and at the time there was one Product Designer in the company. This meant showcasing ownership and how my previous experiences would align with their specific needs.
I applied through an employee referral. The process took 5 weeks. I interviewed at Common Wealth Retirement (Toronto, ON) in June 2023
Interview
It's difficult to be seen as objective after not receiving the role, but here are the facts of my end-to-end interview process.
I had 6 official interviews, with added touch points.
1 – Screener call with Director of People Ops (30 min)
2 – Interview with Director of Sales and Partnerships (hiring manager) + Dir of People Ops (75 min)
3 – Assignment presentation with Dir of S&P + CSM + AE (60 min)
3.5 – Check-in call with Dir of S&P to prep me for next step of interview process (15 min)
4 – Interview with CCO (30 min)
5 – Interview with Co-CEO (30 min)
6 – Interview with CCO + CSM (60 min)
At the end of interview #6, I was told there may be interview #7 which was an aptitude test because the Co-CEO likes to test candidate skills.
I was told by Dir. of People Ops that interview #4 was going to the final interview, with the Co-CEO, but a scheduling conflict led them to swap out who I'd be meeting with next, turning one interview into two.
The Co-CEO was 15 min late to my interview and ended the call 5 min early; I had requested to reschedule the call because of the limited time but I didn't receive a reply.
After interview #5 with Co-CEO, the Dir of People Ops told me I'd be receiving a decision (yes or no) by end of that same week – instead I received a call from Dir of S&P to schedule interview #6.
The Common Wealth careers page outlines a 4-stage interview process.
The Customer Success Manager job posting as of 8/14/23 is not as advertised. It listed "End-to-end onboarding" and "Add value to customers post-onboarding" as responsibilities, however the CSM role was verbally described to me by the CCO and current CSM as administrative – following up with customers for documentation to get onboarded – while the operations team handles everything after that.
This would be the second CSM hire ever for the company.
---
My take is that Common Wealth doesn't fully know how to define the customer success organization currently. They need someone to chase customers for documentation, but training and education lives with Operations, while renewal, expansion and demoing of the product lives with Sales.
Interview questions [1]
Question 1
Describe each role you held before the first one on your resume. We want to understand what led you to Customer Success to begin with (paraphrased).
I applied through an employee referral. The process took 3 weeks. I interviewed at Common Wealth Retirement (Toronto, ON) in May 2021
Interview
Three step interview. One with HR, one with product and engineering, one with founder. There was a simple take home design project that involved reviewing an enrolment flow for their product.
Interview questions [1]
Question 1
They asked about my approach to design and asked me to walk through an example of a project that I had worked on.