Cain Brothers Interview Questions

21 total interview insight submissions
Interview Experience (75%)

The Interview Experience is a score from 1 star (very negative) to 5 stars (very positive) generated based on the Interview Insights at this company.

The number you see in the middle of the doughnut pie chart is the simple average of these scores. If you hover over the various sections of the donut, you will see the % breakdown of each score given.

The percentile score in the title is calculated across the entire Company Database and uses an adjusted score based on Bayesian Estimates (to account for companies that have few interview insights). Simply put, as a company gets more reviews, the confidence of a "true score" increases so it is pulled closer to its simple average and away from the average of the entire dataset.

3.3
  • Very Negative
  • Negative
  • Neutral
  • Positive
  • Very Positive
Interview Difficulty (68%)

The Interview Difficulty is a score ranging from very difficult (red) to very easy (green) generated based on the Interview Insights at this company.

The number you see in the middle of the doughnut pie chart is the simple average of these scores. The higher the number, the more difficult the interviews on average. If you hover over the various sections of the doughnut, you will see the % breakdown of each score given.

The percentile score in the title is calculated across the entire Company Database and uses an adjusted score based on Bayesian Estimates (to account for companies that have few interview insights). Simply put, as a company gets more insights, the confidence of a "true score" increases so it is pulled closer to its simple average and away from the average of the entire data set.

2.2
  • Very Easy
  • Easy
  • Average
  • Difficult
  • Very Difficult
% Interns - FT Offers (100%)

The % of Interns Getting a Full Time Offer chart is meant to provide a realistic estimate of the hiring practices of the company based on the reviews at this company.

The number you see in the middle of the doughnut pie chart is the simple average of these scores. If you hover over the various sections of the doughnut, you will see the % breakdown of each score given.

The percentile score in the title is calculated across the entire Company Database and uses an adjusted score based on Bayesian Estimates (to account for companies that have few reviews). Simply put, as a company gets more reviews, the confidence of a "true score" increases so it is pulled closer to the simple company average and away from the average of the entire data set.

93%
  • 0%
  • 10%
  • 20%
  • 30%
  • 40%
  • 50%
  • 60%
  • 70%
  • 80%
  • 90%
  • 100%

Interviews at Cain Brothers

Filter by:
Year
Job Title
Group/Division
Location
Experience
Difficulty
Intern
Year 2026
Job Title Intern
Group/Division Investment Banking
Location New York
Experience
Very Positive
Difficulty
Average
1st Year Analyst
Year 2025
Job Title 1st Year Analyst
Group/Division Healthcare
Location San Francisco
Experience
Negative
Difficulty
Average
Student / Prospective Monkey
Year 2025
Job Title Student / Prospective Monkey
Group/Division Generalist
Location New York
Experience
Positive
Difficulty
Average
Student / Prospective Monkey
Year 2024
Job Title Student / Prospective Monkey
Group/Division Investment Banking
Location New York
Experience
Very Positive
Difficulty
Easy
Student / Prospective Monkey
Year 2023
Job Title Student / Prospective Monkey
Group/Division Investment Banking
Location New York
Experience
Positive
Difficulty
Easy
2nd Year Analyst
Year 2022
Job Title 2nd Year Analyst
Group/Division Real Estate
Location New York
Experience
Positive
Difficulty
Average
Student / Prospective Monkey
Year 2022
Job Title Student / Prospective Monkey
Group/Division Investment Banking
Location New York
Experience
Positive
Difficulty
Easy
Intern
Year 2021
Job Title Intern
Group/Division Healthcare
Location New York
Experience
Positive
Difficulty
Very Easy
Intern
Year 2021
Job Title Intern
Group/Division Investment Banking
Location New York
Experience
Negative
Difficulty
Easy
Student / Prospective Monkey
Year 2021
Job Title Student / Prospective Monkey
Group/Division Healthcare
Location San Francisco
Experience
Neutral
Difficulty
Easy

Interview Questions & Answers - Cain Brothers Examples

Internship Interview - Investment Banking

Anonymous employee in New York
Interviewed: February 2026
Outcome
Accepted Offer
Interview Source
Employee Referral
Length of Process
Less than 1 month
Application
1 on 1 Interview
Interview
2 Rounds, one on one with HR for screening and then superday with 3 anaylsts. Pretty standard interviews with 15 minutes behaviorals and 15 minutes technical.
Interview Questions
Asked a hard conceptual question about LBO.

Analyst Interview - Healthcare

Anonymous interview candidate in San Francisco
Interviewed: August 2025
Outcome
No Offer
Interview Source
College / University / On Campus Recruiting
Length of Process
Less than 1 month
Application
Phone Interview
1 on 1 Interview
Background Check
Interview
Did OCR. The process moved quick. It was essentially a 1 on 1 with an associate, and then after that, it was a superday with 3 associates in the SF office. After that, a final call with HR (fit check). Ended up not progressing. The superday was 20 min each (3x), with one technical, one behavioral, and one market related.
Interview Questions
How did the OBBB affect Healthcare as a sector?

Intern Interview - Generalist

Anonymous interview candidate in New York
Interviewed: February 2025
Outcome
No Offer
Interview Source
College / University / On Campus Recruiting
Length of Process
1-2 months
Application
Phone Interview
1 on 1 Interview
Interview
The hiring process at this firm was well-structured, professional, and seamless. It began with an initial phone screening, which functioned as a first-round interview. This call primarily focused on my background, motivation for the role, and a few behavioral and technical questions.

The following week, I had three separate 30-minute virtual interviews via Microsoft Teams. These interviews were scheduled on different days rather than being back-to-back, which allowed for better preparation and reflection between each round.

Each interview followed a consistent structure:

Tell Me About Yourself (TMAY) – A chance to introduce my background and interest in the firm.
Behavioral & Resume-Based Questions – Focused on past experiences, problem-solving abilities, and teamwork.
Technical Questions – Covered valuation methods, accounting concepts, and financial modeling.
Open Conversation (Last 10-15 Minutes) – A more casual discussion where I could ask questions and build rapport with the interviewer.
Overall, the process was well-organized and the interviewers were engaging, professional, and welcoming. They created a comfortable environment, which made it easier to have meaningful conversations rather than feeling like a rigid Q&A session.
Interview Questions
Walk me through an LBO

Summer Analyst Interview - Investment Banking

Anonymous employee in New York
Interviewed: February 2024
Outcome
Accepted Offer
Interview Source
College / University / On Campus Recruiting
Length of Process
Less than 1 month
Application
1 on 1 Interview
Group Interview
Skills Test
Personality Test
Interview
The hiring process was very quick. After visiting their firm and speaking with a few people on campus, I was referred up to speak with their full time analysts and associates. From there, everything moved very quickly, resulting in a 1st round screen before a Superday.
Interview Questions
The most difficult questions included asking how you would value a private company, with limited access to financials and only a few key stats.

Investment Banking Summer Analyst Interview - Investment Banking

Anonymous interview candidate in New York
Interviewed: March 2023
Outcome
Declined Offer
Interview Source
College / University / On Campus Recruiting
Length of Process
1-2 months
Application
Phone Interview
1 on 1 Interview
Interview
Started off on phone call with analyst, then they came for OCR, where I had several one-on-ones. Then spoke with HR administrator for 15 mins (I think it was first official interview and general screening). Then had superday interviews on zoom over a few days. Mostly behavioral, technicals weren't that bad. Just know the 400 questions and healthcare specific info.
Interview Questions
What is the difference between a revolver and a term loan
What are some common multiples
What is beta?
Walk me through rev → free cash flow (clarify that it’s unlevered FCF)
How would $100 increase in cash affect Enterprise Value (it doesn’t)

Analyst Interview - Real Estate

Anonymous interview candidate in New York
Interviewed: March 2022
Outcome
No Offer
Interview Source
Recruiter
Length of Process
Less than 1 month
Application
Phone Interview
1 on 1 Interview
Interview
First round was with two members on the deal team. Questions were mainly behavioral with some deal specifics. Final round is live case study with head of the group.
Interview Questions
Nothing out of the ordinary.

Summer Analyst Interview - Investment Banking

Anonymous employee in New York
Interviewed: April 2022
Outcome
Accepted Offer
Interview Source
College / University / On Campus Recruiting
Length of Process
Less than 1 month
Application
1 on 1 Interview
Interview
Very networking oriented. The interview process only involved one 30 minute interview with 2 current employees. I networked with 6 or 7 current analysts/associates and feel that is the reason I got the offer.
Interview Questions
Recent Cain Brothers Deal
, What makes a good middle market analyst?

Intern Interview - Healthcare

Anonymous employee in New York
Interviewed: May 2021
Outcome
Accepted Offer
Interview Source
College / University / On Campus Recruiting
Length of Process
Less than 1 month
Application
Phone Interview
1 on 1 Interview
Group Interview
Interview
Network with bankers + lead recruiter -> Email resume drop -> first round with VP and associate -> 1-1 technical calls with associates -> offer
Interview Questions
Ranking valuation of DCF vs. trading comps

Summer Analyst Interview - Investment Banking

Anonymous interview candidate in New York
Interviewed: April 2021
Outcome
No Offer
Interview Source
College / University / On Campus Recruiting
Length of Process
Less than 1 month
Application
1 on 1 Interview
Interview
Applied via Handshake at a target and had a first round with their recruiter. They never sent me the interview link, and it ended up being delayed because of that. I was ghosted after the first round and know someone else who was too.
Interview Questions
Difference between financial and strategic buyers

Summer Analyst Interview - Healthcare

Anonymous interview candidate in San Francisco
Interviewed: April 2021
Outcome
No Offer
Interview Source
College / University / On Campus Recruiting
Length of Process
Less than 1 month
Application
Group Interview
Interview
OCR resume drop into a zoom interview with an associate and vice president. Chill initial interview process
Interview Questions
Not really in order of difficulty just what I can remember :

3 methods of valuation walkthrough
DCF walkthrough
Gordon Growth Walkthrough/Use case
video
Break into Cain Brothers
WSO Academy helps place students in Elite Firms around the world
$50m+
Est Annual Revenue
$300m-$499m
AUM

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