In the autumn of 2010, as an undergrad studying government at Connecticut College, Amy Cheetham had big dreams of one day landing a coveted gig on Wall Street.
But, having grown up in rural Maine with two scientists for parents, Cheetham had few industry connections to pull on. The odds of landing a prestigious Wall Street internship seemed to be against her.
"The way you usually get a role at a bigger bank is through an internship," the now 28-year-old finance industry executive explained in an interview with Business Insider.
Attending a so-called non-target school — one outside the select few Harvards, Yales, and Stanfords of the world, from which Wall Street typically recruits heavily — also seemed like a barrier.
To overcome those challenges, Cheetham hatched a plan to use cold emailing to connect with Wall Street recruiters and executives. Often written off as the place where emails go to die, Cheetham was undeterred by the idea of reaching out to people unprompted.
In fact, after sending about 150 emails, her plan finally worked. She landed a summer internship in sales and trading at JPMorgan in the summer of 2011.
That internship would serve as the foot in the door she needed. After another internship at JPMorgan the following year, she received a job offer to join the firm as an analyst when she graduated college in 2013. After two years at JPMorgan, first in sales and trading and then with the investment bank, she made the jump to private equity.
In 2015, she joined Summit Partners as an investment associate in San Francisco, eventually becoming an investor herself. Last year, she joined Costanoa Ventures, a California-based VC firm that invests largely in enterprise software companies, as vice president.
In June, Cheetham tweeted about her initial experience breaking onto Wall Street in a thread that was widely shared.
—Amy Cheetham (@amyecheetham) June 18, 2020
Cheetham shared more actionable advice with Business Insider about cold emailing and engaging with Wall Street managers you don't know yet. Here's how to start.
Identify your target contacts and "knock-off the low hanging fruit" first
Starting off, your first step should be to identify whom to reach out to, Cheetham said. That requires some initial research.
"Do enough work so that you're not just cold-blasting the Internet," she said.
The goal here is to identify people working in your chosen field with whom you have something in common — like having attended the same high school, or being an undergraduate at the same university they went to.
"Start wherever you can that's easiest," she told Business Insider. Or, as she put it in one of her tweets: "Knock-off the low hanging fruit first."
And be sure to keep it brief. In those first few emails to new contacts, don't ramble.
"Outline your questions in an email and, if you're looking for a job, just say that," Cheetham said.
See more: A CEO and former Googler explains 3 steps for crafting the perfect cold email
The key, she added, is to get to the point: Share the critical information like who you are, why you're reaching out, and what your request is. It might just be a 15-minute or half hour introductory phone call for advice, or a few questions they can answer on email, but don't be vague.
She characterized the tone as polite, but focused: "Here's why, and here's why I think you can help."
Don't expect immediate replies — but be persistent
Prepare to send a lot of emails that will go unanswered.
"I probably got maybe 20 or 25 responses" out of her roughly 150 cold emails, Cheetham said. That's about one response for every seven emails she sent.
"A lot of folks were open to doing a really brief call, which was all I needed," she added.
—Amy Cheetham (@amyecheetham) June 18, 2020
So, the next step is to master the art of the non-irritating follow-up message.
Over a period of a few weeks following your first outreach, gently follow up with people; send no more than two to three follow-up notes before moving on to the next group of contacts on your list.
"There's a fine line between persistency and annoying," she said.
When someone does reach out, don't waste their time
If you've asked for time on the phone with an executive or recruiter, don't squander it. One way to show you appreciate their time is by coming prepared with meaningful questions.
Afterward, send a thank-you note or keep them posted on your progress, especially if they've put you in touch with a valuable industry connection, Cheetham wrote.
—Amy Cheetham (@amyecheetham) June 18, 2020
"Every time you'd meet someone who was even remotely helpful, it felt good," she said. "You get that glimmer of hope that someone's going to be helpful."
Reading books and following industry leaders on social media are two ways to learn more about your target career and start forming connections, Cheetham said.
"People forget that there are a lot of books about finance or industry or tech or whatever business you want to go into that actually have great lessons in them," she said.
And then there's social media: "I really think Twitter is actually a good place to learn a lot of stuff," Cheetham said. "Following people that work in your industry and just trying to learn from them is really valuable."
If you're an established professional who can help others — then, help
And don't forget to pay it forward, Cheetham added.
"I really hope that people in positions in power think really hard about how they got to where they are," she said, "and I would imagine most of them had someone that helped them."
Cheetham encouraged successful Wall Streeters to help young hopefuls when they reach out like she did: "I'd say return the email or take the call."
And for early career professionals aiming to follow her footsteps, Cheetham had an encouraging message for them, too. "Keep being persistent and working at it," she said, "and hopefully, you'll find a way to get there."
Are you a young person working on Wall Street? Contact this reporter via email at rhodkin@bjinnox.com, encrypted messaging app Signal (561-247-5758), or direct message on Twitter @reedalexander.
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