by Brian DeChesare Comments (18)

From Insurance Sales to Investment Banking: How to Make Up for an Unknown School, a Low GPA, and No Relevant Internships

Sales to Investment Banking

What background makes it toughest to break into finance?



The back office?

Being a male escort in Tokyo?

Each of those careers presents different challenges.

But there’s one particular background that bankers do not like: insurance, and specifically insurance sales.

If you attend a university where “everyone” does it, though, you could easily end up doing it as well.

Our reader today had it even worse:

  • He went to a school that was completely off the radar of large banks.
  • He had a low GPA (3.4) below the minimum that most banks required.
  • He had a total of 0 relevant internships.
  • And he only made a serious effort after junior-year recruiting had finished up.

Despite all that, he recently won a full-time offer at a boutique bank.

And he has a few ideas on how to overcome all these challenges if you’re in a similar position:

Falling Into Insurance Sales

Q: Can you give us an overview of your story?

A: I grew up in the Chicago area and had a few family members involved in the banking industry, so I was interested in finance even before university. Unfortunately, I wasn’t thinking far enough ahead to attend a top school.

So I won admission to a few “good” undergraduate business programs in my area, but nothing that would help with IB.

At my school, one insurance company attempted to recruit almost everyone.

So I interned at that insurance firm and eventually rose to a management role in sales over three years, but that experience turned out to be a huge negative in interviews.

I liked sales, but over time I realized I wanted to work with large companies rather than individuals.

Unfortunately, I was so clueless and so far behind that I missed junior-year IB recruiting season (I applied to a few banks, but it was very late and I never heard back).

I did some networking, but got almost no responses.

So I took a different approach and attended a summer finance program offered at a top business school in the area, and spent three intensive weeks there learning financial accounting, corporate finance, and some financial modeling.

I then used that program, plus a brief stint as an “equity research analyst” for our school’s investment fund, to network more aggressively and cold email banks in the fall of my senior year.

I still didn’t gain much traction after months of effort, but then I changed up my approach heading into December / January.

That led me to win multiple job offers within the span of a few weeks, including one that I accepted at a boutique investment bank.

Q: OK, so a couple questions there…

First off, why do bankers hate insurance firms so much?

A: Insurance salespeople are always calling bankers, pitching products, and annoying them.

Finance professionals also tend to view insurance sales as “below” their work.

I improved my interpersonal and presentation skills through the job, but otherwise it was a big hurdle to overcome.

Q: But you just said that your insurance firm was calling bankers all the time.

You must have had a few clients in the finance industry – why didn’t you network with them?

A: Yeah, that was an overlooked opportunity: I was an inexperienced student, and I didn’t know that networking with the firm’s clients was “allowed.”

Many clients told me to look into investment banking as a career (just as a random comment in passing)!

I did apply to 5-6 large banks in my junior year, but I completely ignored middle-market and boutique firms until much later.

Intensive Summer Finance Camp 101

Q: So you applied for internships too late, you didn’t have any real options, and as a result you ended up doing this “summer finance camp” instead.

What were the benefits?

A: For me, there were three distinct benefits:

  1. Better Brand Name – I could “hide” my lesser-known undergraduate institution by saying I was a “[Top Business School Name] Grad” instead.
  2. Network – The school had a built-in network, and I met a lot of professors and professionals during the program who were willing to help me.
  3. Academic Rigor – I partially made up for my 3.4 GPA by earning perfect grades in the program and pointing to the difficulty of the classes. This school had a reputation for being difficult, so that also helped my case.

Q: Yeah, agreed on all those points.

Can you explain how you networked after completing this intensive summer program?

A: I went to the LinkedIn page of the business school, found alumni and investment bankers who were in the group, and started messaging 10-20 contacts per day.

In total, I contacted ~500 bankers via LinkedIn.

I also looked up banks in my area each week and sent emails to everyone I could find.

Over the first four months, I got a fair number of responses, but nothing that led me to final round interviews at any firm.

A lot of people said they would “pass my name along,” but then never did anything.

Q: Why do you think this strategy didn’t work well?

A: It was a combination of factors:

  1. My GPA and academics were lackluster;
  2. I didn’t have relevant internships; and
  3. My email template was generic and poorly worded when I first started.

Q: Did you try anything else when you didn’t get great results via email?

A: I did some cold calling as well, but I felt more comfortable with email and received more responses via email.

I also attended other schools’ career fairs, but that didn’t work too well for me.

I went to four other fairs, but bankers lost interest once they found out I wasn’t a student at the school.

Also, the banks at those career fairs were all quite large – the smallest one was Lazard – and they had even less interest in me as a result.

In my opinion, email is the way to go for undergrads who are new to networking.

Bankers are in their inboxes all day, and if you send out enough messages you’re bound to get at least a few responses.

Q: But you weren’t getting helpful responses at first.

Why and how did you change your approach?

A: The low point came in early December of my senior year. I had just found the email address of the Chairman at a well-known boutique, and I emailed him with a variation of my usual template (also attaching my resume).

He responded with a personalized rejection email, writing:

“Thanks for your interest in [Bank Name]. Unfortunately, your email didn’t reflect much effort or initiative to tailor your efforts to [Bank Name][More explanation about how poor my email was]. Also, we require at least a 3.8 GPA.”

That harsh, but brutally honest, response convinced me to change my approach.

Effective Emails 101

Q: So what did you do?

A: I made three main changes:

  1. I customized my emails for each bank, even though this made my initial messages longer.
  2. I focused on firms where I knew someone or could spin some type of shared connection.
  3. I also stopped contacting large banks altogether and focused on smaller banks. But I also broadened my search and emailed commercial banks, different types of lending firms, and any company offering “financial analyst” jobs.

Q: To make this more concrete, can you give a “Before” and “After” email to show us what worked and what didn’t work?

A: Sure. Here’s an example of an email that did not work well:

“Greetings [Banker Name],

My name is [Name] and I am currently a student at [University Name] excited to get into investment banking. I am reaching out because I have searched for many investment banks, came across your website, and hope to hear back from you guys. Additionally, I saw you went to [Business School Name], and I recently finished [Summer Program at Business School].

I am willing to work in any group within the investment banking division, but I prefer to work in the middle market industry at this time. I have applied to many banks, interviewed at a few, and have not heard back from most.

I have some experience in I-banking from working with my colleagues at [Business School Summer Program], and I am a diligent, hard-working individual. I believe this would be a great opportunity if I am given the chance to interview, or if you could pass my resume along to anyone within your firm.

My resume is attached, and I hope to speak with you soon.

Best regards,


Q: Wow.

That’s not the worst email I’ve ever seen, but I’m still surprised you got any responses.

How did you modify this email to get a better response rate?

A: Here’s an example of an email that yielded a better response rate:

“Dear Mr. / Ms. [Banker Name],

I hope this email finds you well. I am currently a student at [University Name], and I completed the [Business School Summer Program Name] this past summer, with a focus on corporate finance, financial modeling, and investment banking. I have previous experience in insurance and equity research as well.

I am set to graduate in [Month Year], and I am very interested in your firm because of your focus on [Industry Name]. One of my contacts, [Name and Explain Who the Person is], also focuses on [Industry Name] at [Bank Name], and has discussed recent deals such as [Name 1-2 Examples] with me.

If you have any availability next week, I would greatly appreciate the chance to speak with you and learn more about your firm. I understand you are extremely busy, but even a few minutes would be helpful to my recruiting efforts.

Best regards,


So even if I didn’t know someone at the firm, I name-dropped someone else who worked in a similar group elsewhere.

It takes time to research deals in a specific industry, but I got a much better response rate when I mentioned that information.

Q: The name-dropping strategy helped, but there were also many problems with your first email.

How well did this new outreach effort work?

A: I saw better results within 1-2 months of using it – there was one week in February where I had five phone interviews, all via contacts I had emailed 2-3 weeks earlier.

A lot of smaller finance firms still had open positions, so the timing worked out.

Interviews: What’s Your Greatest Weakness?

Q: So tell us what happened in these interviews – what were your top three biggest challenges?

A: Most interviewers asked similar types of questions:

  1. Do you know what investment banking hours are like / what this job entails / what different groups do?
  2. Can you link the three financial statements and explain how changes to one line item impact everything else?
  3. Can you analyze a company’s Cash Flow Statement and draw conclusions about its business from that?

Those questions are not hard if you’ve done a lot of preparation.

But my preparation was only mediocre, so my three biggest challenges were:

1) My Insurance Sales Background – Most banks saw this as a huge negative, and they ripped apart my resume once they saw it.

To respond, I agreed with them on some of the negatives, but I also pointed out that I gained sales and interpersonal skills that I could leverage in other roles.

This experience also helped answer the “Where do you want to be in 3-5 years?” question.

Many other candidates saw banking solely as a path to PE or other exit opportunities, but I could tell a more credible story by saying, “I’ve already done sales, I like sales, and now I want to work my way up to a sales role in another industry by working with higher-end clients.”

2) My Low GPA – The Managing Directors were far more skeptical of my GPA than anyone else.

Analysts, Associates, VPs, and Directors were supportive once they saw my interview performance, but the MDs were very traditional and kept saying a 3.4 was too low.

I countered this objection by pointing to the intensive “mini-MBA” I had done at the business school, and I showed them how I had earned perfect grades in classes that were directly relevant to banking.

I also pointed out that I worked part-time while taking classes full-time for three years, and had done quite well in my finance classes.

3) My Lack of Accounting Knowledge – Looking back on it, I should have double majored in finance and accounting, or at least done a minor in accounting.

My economics classes weren’t helpful because the field is too theoretical and has nothing to do with financial statement analysis.

I relied on your interview guide and several others, which definitely helped, but my accounting knowledge was still spotty in initial interviews.

Q: But your approach must have worked since you won multiple offers.

A: A lot of places were still skeptical, but I ended up with several offers, including one at a distressed M&A-focused boutique bank, which I accepted.

It made sense to join that firm because they had the most interesting work; also, I had been interested in distressed M&A ever since the summer program I completed.

I also asked a few bulge bracket bankers for advice, and they all said I would gain more client interaction at a boutique bank.

The drawback is that my firm has no real training program or formalized instruction, but they did send me some materials to review and I’m sure I can pick up more on my own.

Q: Yeah, accepting that offer was the best move. I’m still amazed at your results, given how late you began recruiting.

Thanks for sharing your story with us!

A: My pleasure.

M&I - Brian

About the Author

Brian DeChesare is the Founder of Mergers & Inquisitions and Breaking Into Wall Street. In his spare time, he enjoys memorizing obscure Excel functions, editing resumes, obsessing over TV shows, traveling like a drug dealer, and defeating Sauron.

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  1. Thanks Brian. Quick questiom for you (and not sure if you already have an article on this) how hard is it to transcend from commercial banking to the capital markets and by capital markets I mean IB? I have seen many people on linkedin start in commercial then go ino capital. I cant seem to get into IB as I recently graduated and my school had little to none recruiting exposure. I know a smaller bank around me has a commercial development program and they also have a capital markets group. I have seen on linkedin that many people have done this program and essentially moved into their capital markets group. Do you think this is a wise idea? Thanks

    1. Avatar
      M&I - Nicole

      Yes, if you’ve seen people moving from that program to capital markets group at that bank I’d give it a shot.

  2. My question is how can you say you are a graduate from a top school when all you did was simply complete a summer program at a well known school its not as if you can say that you had an undergrad degree from there..?

    1. It’s called “stretching the truth to get a better response rate” and then justifying it if someone asks.

      Technically, he was a graduate from the better-known school since he completed a summer program there and graduated from that program. If someone asked for further clarification, he could say that he completed the summer program there.

      He was not an undergraduate at that school, but that’s not what he said.

  3. Hey,

    I want to first say that no amount of thank yous is enough to show how much I appreciate your website and resources. They’ve been helpful in a lot of ways for me over the years.

    2nd I could use some advice. I am 29, graduated in econ in 2008 from a top 10 school, worked as a paralegal for 4 years then decided to get a MSF at a no name school nationally but well recognized in the Chicago area to transition into finance, had a 6 month internship at a boutique ibank that focuses on esop valuation and advisory but they didn’t have any openings by graduation. I was told I did pretty well in the internship but I needed a job so I got a back office operations position at a large reputable mid market bank in the city that I’ve been in for a little over a year now. I am still incredibly interested in getting into a banking/valuations role. What advise or strategy could you give outside of networking within my current bank in chicago and keeping up with the people at the boutique I interned at? What are my chances at this age with this much experience if I’m very open to moving out of country or out of chicago. If you’ve answered this in a previous post, please feel free to direct me there.

    Thanks a ton Brian

    1. Avatar
      M&I - Nicole

      Other than networking, attending industry events, and applying directly to back office roles I am not sure what other advice I can give you since I have not met you in person. I’d also get in touch with alumni if you haven’t already done so.

  4. Hey Brian, let me tell you man, you are a serious help to any undergraduate trying to get into IB. Unfortunately the 4-hour work week didn’t influence me to not be an excel monkey, in fact, id like nothing more… I know you see these all the time, but I just want to know if I’m being realistic. Im going to be a junior this year at a large state university. Not target by any means, but there seems to be a lot of alumni in IB. I was a recent chem engineering student, physics was really tough on my GPA(3.4). I switched over to an econ degree and I’m currently interning at a small accounting/consulting office. I mostly just build financial statements and work in excel on various things. Im also in 2 finance related groups at my school. Im going to buy your networking toolkit in a couple days and treat it as a bible when I start networking for next summer in a couple days. Is my experience interning at an accounting office going to hurt my chances? if I network like a champ will I have a shot at Boutique IB internship next summer? the help is appreciated.

    1. Accounting experience should help you, though it’s always better to do something more closely related to finance. Yes, you can potentially get a boutique banking internship if you network aggressively and have some internship/work experience to prove yourself.

  5. Avatar
    False Perceptions

    I really dislike the perception that grades are an indication of past performance/track record. I graduated with a 3.5 and when I was interviewing for FT a lot of senior bankers acted as if I wasnt even worth there time, even though they’re cool with accepting kids FT who know nothing about finance but have high GPA’s+Ivy . I managed to land a FT at a MM bank and now its all about proving you can handle what’s thrown at you. The worst was the delusional kids from my school who told me I was screwed for recruiting because of my grades and yet they don’t do anything remotely related to FO. The most important thing is to be passionate about you’re getting into and to really be able to sell yourself and the value you will add to the group.

    1. Thanks for adding that. Yes, it is quite stupid how much bankers focus on GPA and academic credentials when, in my opinion, they indicate almost nothing about your ability to do the job. I’m actually tempted to write an article about why they’re not useful indicators… might do it in the future.

      It would be great if you could wave goodbye to all that nonsense once you start working, but unfortunately it is a prestige-driven industry (although I think GPA starts mattering far less once you actually have full-time work experience).

  6. Fantastic read. Congratulations to the interviewee – an excellent success story.

    It’s also very comforting to see that you ask the questions that I (and I assume the majority of other people reading these interviews) am thinking of as I read the interviewee’s story – definitely extracting the most value from your interviewee for the benefit of your audience. Thumbs up.

    1. Thanks for reading!

      Yes, I definitely attempt to press interviewees on the tough questions, at least when it’s a phone conversation. It’s harder to do that over email, though sometimes email interviews result in more organized thoughts…

  7. Brian,

    What would be a few examples of Investment Banking “groups”? And how can I learn about different deals bankers have played a part in? I’m fairly new to this site and investment banking.

    Thanks for your help

    1. You can start with the list of groups and related articles here:

      For learning about different deals, check out DealBook ( or, if you can get access, look up deals on Capital IQ and read about what happened there.

  8. Way to go kid! Love these success stories

    1. Thanks for reading!

  9. Hi Brian,

    First of all, thanks so much for M&I; this website and your advice has been instrumental to my understanding of the industry and how to break into IB.

    My questions: (1) How valuable is doing a summer school/study abroad program during recruiting season? and (2) I’m currently a rising junior (target school, mediocre GPA) completing an internship with a VC in Asia. How valuable is this in terms of IB recruiting next year, and what is the best way to spin VC experience into something meaningful during interviews?

    1. 1) It helps a bit, but it’s far less valuable than internship experience. If you can, try to do it during the school year instead or do an internship while abroad.

      2) It will help a bit, but candidates with IB internships this summer will still be favored because they know VC internships rarely involve substantial work. You can spin it into sounding more relevant using these tips (there’s one example for a VC internship):

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