7 Ways to Sell like a Human

An Enterprise Sales Executive, a Strategic Sales Rep, an SDR, AE, MDR, BDR, ZBR, AMR, VP, Happiness Officer, I could be all things.. but really, I’m just Jen.

One of the most important things I’ve learned recently, is that it doesn’t matter what you have as your Linkedin headline, or what your email signature says. At the end of the day, you are essentially just you, and no title can really change that. At the end of the day, we are all only human.

What do I mean by this? Being genuine (and more importantly, sounding genuine) is key to being a successful seller. I think the following quote sums this up perfectly:

“In sales, you are never selling an object or something tangible. What you are really selling at the end of the day is: Opportunity. Confidence, Conviction and Charisma just allow you to take that opportunity and turn it into art.” –Gurbaksh Chahal

So how do we get there?

I’m certainly no pro, but over the past couple years I’ve learned the most important part of selling today is being real with people. I’ve found that conviction will persevere, and your charisma will allow you to take that opportunity and truly turn it into an art.

“The most successful salespeople today are not the Type-A ‘meat eaters’, they’re not the ones that can ‘sell anything, close anything, don’t give a damn.’ Salespeople today could quite frankly be you, the person that hasn’t sold a day in your life, but you are a real person, an intelligent person, a humble person, a self-reflective person, a person that can communicate, a person that believes in delivering value, in solving problems, in being the best that you can be. YOU can be a salesperson.”  -Tawheed Kader

Sell like a Human. Here’s how:

1. Sell with confidence.

You need to sell with conviction. IT IS KEY.  It helps when you believe in what you are selling. Even better, eat the dogfood and practice what you preach. Focus on what you know and support it. Focus on more than communicating, focus on them. Be assertive.

2. Sell with humor.

Dude, you gotta have a sense of humor in sales; without it… all is lost. I’m a huge believer in making people crack a smile or laugh. Sales is high stress, and fast pace, so when you throw humor into the mix at the right time, it can calm that tension. Humor can bring ease into the conversation and help potential customers open up and share insights around their wants, needs, and company. Don’t be afraid to be funny!

3. Selling is solving problems.

“The best salespeople are professional problem solvers.” Stephan Schiffman.

The true beauty of sales is overcoming those massive challenges. I’ll never forget the first deal I ever lost– I was devastated. It wasn’t until TK our CEO told me “Jen, this is not a failure. It’s a learning experience. In the end, it’s only a deal. Not the end of the world. Reflect on the good, the bad, and move on.”

4. Selling is showing you genuinely care.

“Honestly, what’s more human than actually giving a damn about their life, their career, their company. Better yet, stop calling them prospects and start calling them “customer advocates.” — Great insight from the unstoppable Jill Rowley.

5. Selling is being a social.

Hear and communicate effectively with all customers and potential customers (aka customer advocates) on ALL social channels. Make sure you’re leveraging different tools in the proces like (these are my must-haves):

  • Salesforce
  • Gagin
  • Twitter
  • Linkedin
  • ToutApp
  • DocuSign

Always be learning. Attend sales meet ups, webinars, and listen in to sales podcasts.

Follow sales leaders, here is a place to start: John Barrows, Koka Sexton, Jill Rowley, Matt Heinz and Scott Britton.

6. Educate and inspire.

Selling is educating and inspiring your customers. Make sure you’re doing the 5 E’s of Social Business.

  • Educate with content
  • Enchant by being relevant
  • Engage with authenticity
  • Embrace them by starting an open dialogue
  • Empower by giving them the right tools

7. Celebrate the small wins.

In sales, you have to celebrate the small gains. GET EXCITED about that one meeting you’ve been working on for over a month, that one awesome email, that deal you closed, that shout out from your boss, and most importantly celebrate the success of your teammates.

Key takeway.

In the end, we are all human beings. Sell with integrity, sell with conviction, sell as if you are key stakeholder for their success.

If you are a genuine person, an intelligent person, a open person, a self-reflective person, a person that can communicate, a person that believes in delivering value to your customer, in solving problems, in being the best that you can be – you are meant to be in sales.

Above all be you. Because you’re friggin awesome.


7 Essential Shortcuts Every Salesperson Should Know

“Not enough time in the day” – said every salesperson, ever.

More than just copy-pasting, this post is for people who are ready to take their productivity to the next level. Are you constantly clicking through tabs, applications and search?  Of course you are – here’s how to get stuff done faster. Here are 7 simple ways that will help you be more efficient. Seriously, this is how you add more time to your day.

Please note: If you’re cursed with a windows computer, substitute ctrl for ⌘

Transitioning Shortcuts:

1. Switch between applications
⌘ + Tab

*Pro Tip: keep your thumb on ⌘ and tap Tab to switch between all of your open applications

2. Switch between different windows in the same application

 ⌘ + ~

Shortcuts with Chrome:

3. Open the last tab you (accidentally) closed
⌘ + shift + T

4. Opens link in a new tab
⌘ + click link

5. Switch between open tabs

    (or 2, 3… 9)

*Pro Tip: ⌘ + 9 will always open the last tab in the window

6. Put your cursor in the URL bar
⌘ + L

7. Open up window in incognito mode
⌘ + shift + N

*Pro Tip: 3 uses for incognito mode that prove it’s not just for NSFW material


As you start your journey for less mechanical mouse clicking, consider checking “warn before quitting” under the Chrome menu.  This will help your tab surfing not accidentally close all of the hard work you’ve done.

*Blog written by Dan Smith–aspiring productivity guru. Follow him on Twitter!


How To Build Trust Like an FBI Agent

I attended a conference last week (CMX Summit) that answered the question, how DO YOU engage people?

My favorite person that spoke was Robin Dreeke, former head of the FBI’s Behavioral Analysis Program.

Sales is about connecting people. It’s about standing out in a crowd, getting into someone’s email inbox, or setting up a meeting. You may pride yourself on being charismatic, and you probably know how to close deals.

But, do you want to know how to do it faster? And more often?

Dreeke shared some psychological life hacks that will help you build trust and form relationships faster. They are easily applicable to your sales process since sales, in essence, is all about human interaction. Dreeke argues that people do not form loyalty with organizations, they form loyalty with people. Here are 5 things you should remember when understanding your leads or prospects. The more you’re able to connect with a person, the faster the relationship can be built.

1. Learn about their priorities, goals, and objectives.

The first step to understanding anyone is taking the time to learn about them. In sales, you should immediately gauge a deeper understanding of what is top of mind for your potential customers. How do you do this?

My absolute favorite line that Dreeke said was,

“If you don’t know what to ask, ask them what their challenges are.”

This question can apply to almost every life scenario. To build the bond and trust with any relationship (even your friends), you’ll want to establish understanding for their headspace. When you ask this question, the challenge they list is their number one priority they are dealing with at that moment. They’re telling you their gut reaction and thoughts! Use that to your advantage to sell.

2. Ego suspension. Get rid of it!

Even though this seems apparent, I think this is an amazing reminder for every salesperson. Sales is inherently competitive, so there has probably been cases when your confidence has helped you close deals. The fact of the matter is, your prospect on the other end of the email or call doesn’t care if you’ve closed the most deals on your team, or your boss thinks you’re the bees knees. At the end of the day, when you let go of your ego, you’ll become a better seller.

This quote really got me thinking. “Don’t be collateral damage in someone else’s insecurities.” In sales (and life in general), it’s easy and natural to take things personally. Say you have an angry person on the other line that won’t stop yapping. The minute you realize that their anger is simply that, their anger and not yours…it’s easier to not be so affected by the situation. Dreeke says,

“People very rarely go at you for personal reasons; it’s their own insecurities.”

Keep calm, and let go of your ego when selling.

3. Allow them to talk.

You might have heard this before, but now an FBI agent is absolutely confirming it. Finding the pain points on a sales call is one of the most important first steps you can take as a salesperson. Your main goal is to figure out how your product will fit in their company’s workflow.

In Sales, the best way to get to know someone and understand them is to LISTEN. Ask discovery questions, but always make sure they are talking more than you are. They can research your product online, but this is your chance to research them.

“Validation is nothing more than asking questions and find the context”

4. Place them ahead of you

Forget about your quota, and first think about how you can help them. The minute you start caring more about them, and they can tell that you do, the better seller you’ll be.

“HELP them understand what they are trying to do and achieve it.”

5. Seek their thoughts and opinions.

A good mentality to have is to seek your leads as resources too! Get excited that with every call or email, you get an opportunity to learn more about the space you’re selling to. Try asking their advice on a specific question. It’s different from your old-school sales strategy, but it will help you build a real relationship vs. being “salesy.”

Final takeaway…

When you build trust with a person, you’re able to feel like you’re some sort of team. Having a “partner” in the sales process will help both sides achieve their goals and build champions. Robin’s 5 pieces of advice might seem simple, but if you apply them on a daily basis, I believe you’ll become a better and faster seller.

After all, if you can build trust the way an FBI officer does, it’s likely you can build trust on your sales call.

If you have any sales tips/tricks you want to learn about, tell me here!



The Secret Call to Action You’re Not Using in Your Sales Email

Writing a good sales email is hard. No wonder we wrote a whole guide to teach you how to write kickass emails.

You probably know how to write a good email, but I bet you’re missing out on precious opportunities by not using two simple letters “P” and “S”.

I’m talking about “P.S.”

How it lands meetings.

P.S. is a classic copywriting technique that can make your sales email more effective.

Look at this email below:

This could just be another sales email to demo a product, but its the last line that makes it incredibly effective.

Adding the P.S. gives you a chance to add a small nudge or call to action.

So why does it work? It’s a part of the basic human psychology called the Serial Position Effect. Simply put, people remember the things that are in the end of a list.

If you write an email, there’s a good chance that the reader will read and remember the last thing you wrote.

Who’s using it?

Don’t take my word for it. Even Jill Konrath, the popular sales influencer, uses it in her emails:

As you can see, Jill used the “P.S.” as one last chance to sell.

How it subtly sells.

The P.S. can also act as a nudge to sell something in a subtle way. Take a look at the email below:

The email is to thank a blogger for his quality content AND creatively uses a P.S. to tell him about a product and get him to sign up.

Now that you’ve seen some examples, start using P.S. and closing more deals!

P.S. Comment and let us know if p.s. has helped you make your emails more effective.


Feature of the Week: Track Your Content

What’s cooler than tracking links?


Did you know that with ToutApp, you can track your presentations, documents, pictures, etc.? See when a prospect or lead clicks on your pricing sheet or e-book. Some examples where you’d use this:

  • Tracking to see if your prospects have opened your pricing sheet
  • See when your presentation is opened
  • Did they look at your case study?

In case you’ve forgotten, here’s how to track your content (in Gmail and Outlook):

1. In Gmail, it’s right in your email next to your other favorite features.


**You can choose to upload a new file, or quickly go to the documents you regularly send out in emails. It’s a quick sales trick to grab the presenation or doc you’re always using.

2. In, it’s in a similar spot above the body of your email.

3. In Outlook, it’s located on the right.

**Have an idea for Feature of the Week? Tell us about it! 


5 Sales Hacks That Will Change Your Business

Secret Sauce:

I’ve tried to write this without giving away too many secrets. My best hacks I keep to myself because if they became overused, they’d be obsolete. I won’t bore you with Rapportive hacks or any of the 101 stuff either. I hope you enjoy these and put them to good use.

Sales Hack #1 –  Frienemies

Salespeople are almost always taught to connect with their prospects on Linkedin. What they aren’t taught are how to configure their privacy settings. Therefore, if you are connected to someone and they haven’t fixed their settings, you can see when they have a new connection.

Now why am I telling you this? Well first go out and connect with reps at your competitor’s companies. Most of them probably haven’t played around with their settings and won’t think anything of it when you asked to connect. Once you’re connected, just wait to see who they connect with. When they connect with a prospect, you’ll be notified via news feed and you can send a very well timed email. Just don’t mention how you knew to send them an email at the perfect time.

Sales Hack #2 – Cold Emailing

There are plenty of articles out there on writing cold emails but people maybe don’t realize, or maybe don’t mention how situational it is. I believe that writing a cold email to the VP of Marketing at Verizon is very different than writing to Marketing at ToutApp. Smaller organizations give more people decision making power and need more info upfront but for bigger orgs, less is more.  I like to aim high in their org with a simple “introduction Request” email that usually gets forwarded downstream to the person you’re supposed to be talking to.

This works for a few reasons:

  1.  It gives you a chance to not say anything that will make them shy away from you. If you give too much info you may end up over selling or trying to hit the wrong pain point with the wrong value  prop. Get on the phone and get some info before you pitch them.
  2. You get forwarded or intro’d down stream, so their boss is literally telling them to talk to you.
  3. It’s easy for them to get it off of their plate. They can respond with nothing other than the right person being Cc’d on the email.

This can work really well for reaching out to high level employees at big companies. Just don’t think cold emails in sales will work in every occasion.

*Side note – I haven’t shared this anywhere else but it seems to be getting written about plenty these days but in different contexts. Soon people will wisen up and it will stop working. Until then, try it out and see if it works for you.

Sales Hack #3 – Messaging

Too often I see people asking for favors in a manner that presents them, well…asking for favors.  When I left Udemy I wrote my personal network asking for people to introduce me to companies that needed a business development rep. I knew I wanted to stay at a small startup but I wanted to hear out all of my options and I didn’t want to start hearing offers while I was still with the company.

One thing to know and never forget. It’s not what you ask, it’s how you ask it. Instead of saying. “I just left my company. Do you know anyone who is hiring?” you say, “I just left my company. If you know anyone looking for a killer BD rep, do them a favor and introduce them to me.” It completely flips the script. That’s my favorite example but keep this in mind when trying to sell something. Whether is written or verbal communication, a lot can be done just by how you phrase things.

Sales Hack #4 – Web Scraping

One of the main points of the Sales Hacker Conference is to get salespeople to embrace all the new technologies that have rapidly evolved over the last 2-3 years. Web scraping is now easy to do for non-technical salespeople. This can open so many doors in the outbound lead gen space.

One tool I like to use is In the event space, I can scrape lists of companies that have sponsored similar events, raised a certain amount of funding, are located near my next conference, etc. If you’re customers are restaurants you can easily scrape sites like yelp. If they’re lawyers you can scrape Avvo. You need zero technical ability to use for basic web scraping and list building. Oh, and it’s free to use!

Two other great tools for list building are LittleBird or FollowerWonk. Both allow you to scrape twitter bios. At Udemy, if I needed to onboard someone that taught PHP, a PHP expert will usually have PHP in their twitter bio. Same thing works if I want to find people in sales in the Los Angeles area.

After I’ve scraped lists I like to get emails using Salesloft or Toofr and fire away emails using ToutApp, of course.

Sales Hack #5 – Outsourcing & Automation

I’m an automating machine. I automate as much as I possibly can. The entire process of list building and outreach can be taught entirely to a Virtual Assistant in the Philippines at $3 an hour (which is a nice wage there so don’t feel bad).

The web scraping in Sales Hack #4 can be taught to anyone. Once they have company names they can find the proper title, first name, and last name of anyone at almost any company solely using linkedin and the company’s About/Team page.  Once that have that they can use Salesloft or Toofr to pull emails. Then upload them as a group of multiple groups into ToutApp. Create a template or a few, and have them send as frequently as you’d like. You just automated the entire outbound sales process up until you receive a response.  I can even instruct my VA’s to set up a call if the incoming email takes me longer than 30 seconds to read.

This process allows you to build massive, targeted, and fresh lists for very little money. Go ahead and try it for yourself!

*Bonus Hack*

I use ToutApp to send the bulk of my emails. When I’m emailing a group of less than 20 people, sometimes I like to add a personal note as the first sentence.  I’ll usually add a column to the spreadsheet I’m uploading with the group I’m about to email called Personal. In the cell for each person I can write my custom personal line for each email. When I upload the sheet, I map it to a custom field {personal} and then dynamically add it into my template. This is the best way to send personalized emails to an entire group.

Max Altschuler is the Founder of the Sales Hacker Conference, Previously the VP of Business Development at AttorneyFee (which sold to Legalzoom), and the first sales hire at Udemy. If you want to see more Sales Hacks like these, sign up for the Sales Hacker Conference on April 24th in NYC or subscribe there for updates on future events and livestreams.

Follow Max at @maxalts


User of the Week: Grouper + ToutApp = Dating perfection?

User of the Week: Cindy Blass

Company: Grouper

1. What’s your company/role?

Grouper is a social club that sets up drinks between 2 groups of friends. We work with the most interesting people and places in your city.

As the Sales Manager at Grouper I spend my days searching for and partnering with the best venues in the US, Canada, & the UK to host Groupers.

2. Why do you love ToutApp? How do you use it for your job?

ToutApp has been a breath of fresh air for our sales team. It helps us to be more efficient (templates), more organized (Salesforce integration), and most importantly helps us to keep in touch with our venues (schedule send & reminders).

3. Why Tout vs. other sales tools in the market?

As soon as we started out Tout trial we knew it was the one! Aside from all of the amazing features (sales gong!!), the customer service is second to none (shout-out to Happiness Officers Jen & Natalie!)

4. What was your journey into sales?

Being the youngest in a family of seven you learn pretty quickly how to stand out from the rest. You either develop some sales skills or you’re stuck watching everyone else’s favorite TV show and eating everyone else’s (gross) cereal.

5. What’s one of your favorite sales tricks?

I’ve found understanding the needs of the customer and building a relationship with them to be the most important things any person in sales can do. And always ask for referrals!

6. Favorite email you’ve ever received?

Any e-mail our Director of Sales (Zach) sends – he’s hilarious! :-)


**Congrats to Cindy + Grouper for winning this week! We couldn’t be happier to have you on board with ToutApp. If you’re interested in being the next featured superstar, please apply here. **