Confessions Of A Inbound Sales Bootcamper

By Jeremy Eisenberg - December 01, 2017

Did you know, that, according to the 2017 Hubspot State of Inbound Report, most salespeople struggle with getting a response from prospects (38%), closing deals (35%), and identifying/prospecting good leads (30%)? Furthermore, on any challenge today's salespeople face, they feel prospecting is the hardest?

I do not know about you, but that is true for me. Like a lot of my peers, I am not a natural salesperson. I had no prior training before I started five years ago. I only know, I love working with people, learning more about their challenges, and figuring out how to help them. But it was hard. 

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To help me over the hump (or mountain), I recently had the opportunity to enroll and participate in a sales boot camp led by Dan Tyre, one of Hubspot's most experienced salespeople.

The goal was to sharpen and improve my skills, but the course quickly became a highlight and springboard for my week. I looked forward to my weekly Monday class, my coach, my peers, and improving upon my flaws and reinforcing my strengths. Over the course of two months, I talked, listened, learned, and was surprised each time I joined the call.

I recognize that this was a once-in-a-lifetime opportunity and not many people get to do this - so, I would like to share my key takeaways with you and add actionable tips I learned. While there was much, much, more that was covered in the course; these are my highlights:

#1: Organization Is Key

Time is of the essence when you are a salesperson — however, sales reps everywhere are wasting valuable time. For example, 57% of respondents spend up to an hour per day on a data entry! So, organization is the key! I cannot stress this one enough, no matter how good of a salesperson you are, or will become, if you are not organized you will be flushing opportunities down the toilet (figuratively).

How do you stay organized? For starters, a well setup and efficient CRM, but like everything else in life, if you do not put the proper time into it, you will not get what you need out of it.


The HubSpot CRM makes keeping your prospects organized intuitive and straightforward. Call or email your lead right from within the CRM, and it automatically creates a log of your activity. Did you maybe send a LinkedIn message or Tweet instead? Merely record it in the CRM, along with notes, tasks to follow-up, and even schedule meetings. 

Pro Tip: Unless you like using an Excel sheet to keep up with all your prospects and you have less than a hundred contacts, you should invest in a CRM that works for you. By the way, the HubSpot's CRM starts at free (hint!).

#2: Block Off Time

Yes, I know, this one is so obvious, but it is way to easy to overlook!

Unless you are a full-time salesperson, you might get bogged down in the day-to-day of non-sales responsibilities at your company. You need to schedule at least one un-interrupted hour slot of time each day to connect with your prospects. This hour does NOT include researching your opportunities but actually connecting (or trying to) with them. 

Pro Tip: The best time to schedule this hour is after lunch in your prospects' time zone, and Friday afternoons. Avoid early morning when your prospect is catching up on emails, calls, and probably already has meetings booked.

#3: No Distractions — No, Really!

Again, this might seem obvious, but it is harder said than done. It is so easy to grab a quick coffee before picking up the phone, run into a co-worker you have been dying to discuss last night's game with, and easy as that 30 minutes have flown by.

Lock the door to your office, put up a Do-Not-Disturb sign on your back if you are in a co-working space, go to Starbucks and throw on your headset. Do whatever it is that you need to do in order to get one dedicated, uninterrupted hour a day to calling prospects.

Pro Tip: Use incognito mode on your browser and put your cell phone in your pocket. That way you will not be distracted by notifications or emails, which can quickly take you out of your rhythm.

#4: Be A Boy Or Girl Scout

Be prepared. Did you research your prospect? Do you have a good tip to give them? Do you have your notes in front of you, i.e., in your CRM? Is this your first time calling them, or have you already connected briefly? Be ready with the right questions to ask based on where you and your prospect are in the sales funnel.

However, be aware to follow the inbound sales mantra: Always Be Helpful! You do not want to sell them on your product or services in the first call, just as much as you should not start from the beginning in your second call because you are not prepared. Have your call scripts, research, and tips at the ready.

Pro Tip: Being adequately prepared varies from person to person, so if you need to set alarms on your phone, write notes on your screen, or you can just sit in front of your computer at the beginning or end of the day, do it. 

#5: Share Your Boat

If you think you are the only one who is struggling with some aspect of your sales approach, you are dead wrong. Many times when I was roleplaying with a peer, it was almost like looking into a mirror. I had several, "don't do that, oh wait, I do that too" moments. Realizing a mistake I was making myself, as opposed to hearing it as a critique from my partner that day, made me more cognizant of it. It is much easier to dismiss someone else's suggestion, not your own.

Pro Tip: Practice, practice, practice. If you can find a few fellow salespeople in your networking circles to roleplay with, great. However, even if you do not have any peers to roleplay with, call your mother, brother-in-law, or poker buddy and ask for five minutes of their time.  

#6: Don't Stay Silent

There is a Golden Rule of Three" when selling. If you envision the client's problem to be an onion, you will need to peel away three layers of skin by asking questions to get to the bottom of the problem. They might say at first: "I need more sales." Yes, everyone does, but what drives this motivation in this particular case? If you dig deeper, you might discover that the company is planning to expand or wants to raise capital and needs to show a certain number of sales to do so.

However, for many, asking a lot of questions and digging deeper can feel uncomfortable and needs to be practiced. So take the opportunity wherever it presents itself, whether it is fantasy football or a sales group, and speak up. Not asking questions, giving answers, or offering advice is almost the same as skipping the call. Everyone is there to learn, improve, and share. 

Pro Tip: Practice becoming curious. Whether you speak with a co-worker, a friend, your spouse, or your children, try to ask questions and actively listen to their answers. 

#7: Don't Skip The Homework

Probably the biggest lesson for me: Don't skip your homework! You will regret it if you do. While writing the correct version of a misspelled word until your hand hurts was probably a waste of time in school, practicing your greeting until your voice is almost hoarse isn't.  A big part of sales is being comfortable, which the earlier points of being organized and prepared help with. However, that is not enough, read sales blog posts, try a new sales tool, practice calls with your dog, keep yourself motivated. 

Pro Tip: You got organized, you are prepared, you have practiced — now you need to get on the phone and talk to real prospects. While it might be uncomfortable at first, you will get better very fast. Moreover, keep in mind: You are never as bad as you think you are. 


It is important to remember as we enter 2018, that the balance of power and knowledge has shifted so much that prospects can get into a sales call with more info then the salesperson. It is crucial to continue to learn how to talk to today's buyer, be helpful when you can, relax, and smile.

This experience was eye-opening for me. I am spending the next 4-5 weeks going through the rest of my contacts and reach out, delete or, if I must keep them in the database for contractual or other reasons, I will add them to a quiet list. I will create additional sales sequences and sales templates to be better prepared and spend less time rewriting the same emails. By the beginning of 2018, I want to be in a position where I have my sales process organized and streamlined.

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