Jeremie Cabling on Combatting the Struggles of Selling

Sale (/sāl/): the exchange of a commodity for money; the action of selling something (Part III)

If you can believe it, we have come to the last part of Jeremie’s three-part sales series! Through these past two weeks, we have learned what it takes to be a good salesperson, how to confidently write a cold email, how to persuade and pre-suade, and so much more. This week it’s all about combatting the struggles of selling, Jeremie giving some expert advice on how to navigate a few of the challenges that come along with sales- yes we saved the best for last. I hope you have enjoyed this series as much as I have and get to use some of these tactics in the real world. Just make sure not to use them on Jeremie, I have a feeling he’ll see right through them.

What are some of the ways you combat rejection during a sale?

Jeremie says, if your prospect rejects your proposition, it’s because you led them to that objection. Don’t push prospects to objections.

People have the primal urge to feel safe, secure, and in control. A pushy ask like “Do you have time to chat this week?” puts a person’s guard up and stops a sale dead in its tracks. An ask like “Is it a bad time to chat about X” gives the recipient a feeling of agency and power. It asks the same thing as the former question, but it asks in a way that empowers the recipient to respond.

Ask questions that uncover your customers’ wants. Then, dive deeper to understand how they want to feel. Only then you can pull them in by showing how your product/service is the way there.

If an objection does come up, the only 3 responses I use are:

  1. You’re right in feeling that way, [my prospect very similar to you] felt that too, what they found is [benefit]…
  2. That’s right, but [benefit]…
  3. I don’t know, but let’s regroup and I can get back to you on that…

How do you not get discouraged during the sales process?

“I do get discouraged,” says Jeremie (phew I thought it was just us). “If I’m not performing, I can only blame myself or my process. Discouragement is the natural reminder to step back, analyze and correct myself (my attitude) or my process.”

Sales is fun, Jeremie reminds us, but success in sales is almost essential for fulfillment in it. Discouragement is the cue that something needs to change to get better.

Jeremie, what is the best piece of advice you have received in terms of selling and sales?

Most mentors helped me with the technical parts of selling… best times to sell, how many times to follow up with a lead, etc.

Here are my 5 favorite tools of persuasion in relation to sales

1) Reciprocity: people feel compelled to return favors.

Take the initiative to treat others well -> get treated back exceptionally.

2) Cognitive Dissonance: people feel compelled to act in a way consistent with the image they want to project. Show their actions/inactions don’t project that desired image, but your solution is a way how.

3) Signaling: “We can’t help but assume the importance of a message is proportional to the cost of delivering it.”

-Rory Sutherland.

An email < a text < a tweet < a call < a handwritten letter < a personalized gift.

Make your customer feel like they matter by signaling that you put in effort to reach them.

4) Social Proof: Going back to the need to feel safe… People will go along with people that are similar to them.

5) Liking: All else equal people buy from who they like.

What is the biggest challenge you face in sales?

Time management is critical. Your job is entirely dependent on the interaction with other people — largely strangers. You have to balance your daily tasks to keep your sales pipeline full (prospecting, nurturing old leads, etc.) with calls that go longer than scheduled, people flaking your meeting, having to do miscellaneous work for your company, etc.

Some days you’ll feel like there’s not enough going on. Some days you’ll feel overwhelmed. You have to be comfortable with a level of uncertainty.


Jeremie Cabling on A Good Salesperson

Sale (/sāl/): the exchange of a commodity for money; the action of selling something (Part II)

If you thought you were ready for last week’s sales expertise, you are definitely not ready for this week’s write up on what makes a good salesperson. What makes Jeremie Cabling such an incredible salesperson to me is, not only his ability to sell, but his adept ability at explaining what good selling is and what it looks like. If you want to read more about sales, make sure to tune in next week for Part III of Jeremie’s series, where he explains one of the most critical hurdles that every good sales person must overcome, how to combat the struggles of selling.

What are some characteristics that make a good sales person?

When hiring another sales representative Jeremie is looking for:

Effective Speech: His test is to ask candidates to explain a concept they know well to a 5 year old. If they can explain something to a 5 year old, they can communicate clearly — critical in persuasion.

Good Listener: In a sales conversation you should be doing 80% of the listening and 20% of the talking. People love buying, but hate being sold to. They have to convince themselves that they led themselves to the decision to buy or not. You must know what to listen for. Your job is to ask questions that lead the customer to that decision.

High Integrity: Someone who sees deals as the way to help the customer and their team is someone who will do well in the role. Sales is competitive internally, but you’ll want someone who will help sharpen their coworkers.

What is a good sales opener?

The best sales opener is an introduction from a friend or authority figure. People buy from who they like and respect.

If you can’t get a warm intro, this formula is the most effective I’ve used to start a completely cold conversation over email (21% reply rate vs the ~1% industry average).

Accusation audit + A question that triggers cognitive dissonance + Personalized offer + Call to Value

In English:

Accusation Audit: Label someone with something that you are certain that they identify with. When you acknowledge someone’s emotions, it validates those feelings.

A question that triggers cognitive dissonance: Ask a question that implies that their action/inaction is the contrary to the identity that you just labeled them.

Personalized offer: An offer that shows you didn’t just email them out of the blue. Give them a reason why you reached out, even if it doesn’t make sense. People care about they why.

Call to value: Clear benefit to the customer of continuing the conversation

Here is an example:

Hi {first name} — You stood out as a thought leader in SaaS sales on LinkedIn.

Have you considered sending your best customers gifts? You and 11 other sales leaders in New York City have access to the pilot of my service for sending personalized gifts, automatically. Is it a bad time to try it for free on {company’s best customer]?

Cognitive dissonance is Jeremie’s second most powerful persuasive weapon in sales. This email is meant to make this person question a gap in their sales process, while keeping them in control of the conversation. They should feel safe, but curious. They can trust you to an extent because it seems like you emailed them with a purpose. It’s strictly emotional.

What advice do you have for someone interested in getting into sales?

To get into sales, don’t apply to sales jobs, Jeremie says. Look at companies that you like and start-ups that interest you.

  1. Even email or call your would-be manager, sharing some form of value.
  2. Write a unique cold email that you would use if you worked there and share it… Share a lead with them… Share a relevant article or book summary… Offer to do lead generation free…etc
  3. Put yourself in a position that attracts job offers. While selling my company’s software, I received 6 competing offers by my prospects’ companies because they liked the way I shared value with them. No resume. No interview. Just value shared.

You can’t sell something effectively if you don’t like it. Don’t waste your time, your could-be employers’, and their customers’.


Jeremie Cabling on Intro Master Sales Tactics

Sale (/sāl/): the exchange of a commodity for money; the action of selling something

Sales is a unique occupation, one in which outsiders can’t exactly articulate. We know when good sales are done and when bad sales are done, but don’t know what makes them good or bad sales. This makes sales an art form, one that my friend Jeremie Cabling is a master of. Jeremie and I both graduated from Babson College and participated in the BRIC program together. Throughout my time knowing Jeremie, I have always been amazed by his tactics of friendliness, charisma, and, most of all, persuasion. Whether it be in his personal or professional life, Jeremie is the embodiment of incredible sales, which is why I have asked him to share some of his artful tactics and incredible insights in a three part series on the blog! Stay tuned for next week where Jeremie discusses what it means to be a good sales person.

Jeremie has always been an introverted guy, so why sales?Screen Shot 2020-10-27 at 12.28.18 PM

In elementary school, Jeremie was fascinated by the entrepreneurship presented in the cartoon characters Ed, Edd n Eddy, where the characters started hundreds of businesses over the course of the show. In high school, Jeremie learned more about business by cold emailing entrepreneurs and lawyers for mentorship and building my own little projects. What Jeremie believes landed him a spot at Babson was a pitch he made to his admissions counselor on a business idea of his about college admissions. “To start any venture you need to build and sell,” Jeremie mentions, “I didn’t like building or coding, but learning about sales energized me.” So, in college and post-graduation Jeremie focused his efforts in landing a career in sales. Currently, he is the only salesperson at Showcase, a Techstars backed start-up which helps companies hire faster and more equitably using video interviews. 

Some of Jeremie’s best sales practices?

1. Learn how to persuade

The science of persuasion is hardwired into our brains and what influences us will never change. So, learn how to use words to influence. In asynchronous conversation (emails/voicemails/texts), this requires exceptional copywriting and understanding of what motivates your customer. In synchronous conversation (face-to-face/phone/live video) this requires exceptional listening and persuasive questions.

2. Learn how to pre-suade

Pre-suade by framing those words in the most effective and relevant package for your customer. If you’re selling a product where speeding up a process is the benefit and Silicon Valley execs are your customers… Get on Twitter where those execs consume their content. Engage with their content, focusing your profile, and brand on speed.

Jeremie’s most proud sales moment?

Jeremie’s first internship had a set sales process:

Send 900 emails a month -> book 20 sales calls -> demo 10 leads -> negotiate 3 contracts -> make 1 sale

But, in my first month he sent 1000 emails and booked 1 sales call. That 1 sales call turned out to be a call with an old, confused man, not the COO of a huge casino like he thought. The other 6 sales reps hit 120% of their goals and he hit 0%.

Next month, Jeremie asked his manager if he could try his own process. Jeremie changed how he searched for prospects and wrote his own email copy. That month Jeremie almost doubled the all-time company record for sales calls, while doing half of the usual work. He hit 410% of my goal and led the company to its best sales month in its 7 year history. The VP of Sales valued his deals at $1.2 million. That put Jeremie in the position to build the sales process at his current start-up from scratch.

How does Jeremie best prepare for a sales call?

Sales calls give most early salespersons anxiety.


“The best weapon against any social anxiety is not courage, but empathy.”

A lot of sales reps will try to dig deep to find the courage and risk rejection when picking up the phone. That courage will fade. Confidence won’t. Confidence comes from an empathetic perspective. Any given conversation, even at its worst, can’t be the end of the world. But a good one could do wonders for your career.

What makes selling worth it to Jeremie and exciting?

Jeremie is excited by the hyper accountability- you earn a fraction of the value you bring into a company. Bezos may be worth ~$200 billion, but it’s because he created trillions of dollars in value. “It’s fulfilling to see the value you bring and rewarding to capture what you see is a fair share of it,” he says. It’s the most applicable social skill, he mentions. Use it at the bar to talk to a girl, at school to get better grades, at home to get out of doing dishes. You get paid to practice a superpower everyday. Jeremie also sees selling as a step to start his own business when he is ready and the opportunity is there.