Why you should consider a career in Sales

Last week I had a particularly exciting moment. I had to write two 5-figure commission checks for two of our top sales reps, and surprisingly a commission check for our MDR who had extra time after qualifying inbound leads and so she started closing deals. We call her Meghan “Oops I Closed a Deal” O’Donnell.

What’s the big deal? Aside from the fact that we offer a 20% uncapped rip on every $1 you bring into the company here at ToutApp, the big deal here is that two of my top reps were never in Sales before. In fact, one of them explicitly told me “I don’t want to do Sales. I don’t want to do Sales” at her job interview, and the other started as a Marketing Intern at ToutApp and I convinced her to “help out and call some customers” when we were overflowing with leads.

Duh. Sales is changing.

On one hand, I feel incredibly happy to be paying forward the value that my team delivers. In fact, it is my hope that every single person in the company earns some form of commission for value delivered to the customer, even Engineers. On the other hand, as someone that thinks deeply about where Sales and Marketing is headed (see my article on Wired for more on this), I couldn’t help stop and think about what this all means for what it means to be a “salesperson.”

The experts have been preaching on and on and on about how “sales is changing” — yes we get it, it’s all changing. The experts have also been going on and on and on about “social selling.”  I had to have Jill Rowley explain to me what “social selling” was because to me, and to most of us that haven’t sold before LinkedIn, Google, or ToutApp existed, before “Inside Sales” became a “thing” and before we had to specifically define “Consultative Selling” — quite frankly, we, us amateurs in Sales, just call all of this stuff: SELLING.

The Un-Salesperson

Anyway, I digress. The point here is that it is old news that “Sales is changing.” In fact, Sales has changed. That’s old news. It’s done. What’s new and more pressing today is that the definition of a successful salesperson is changing. I’ve been bugging Jen, one of our top sales reps, who also frequently blogs, and helps make marketing videos, to finish writing her blog post on “Sales Pros vs. Sales Bros” because I think it perfectly articulates what it actually takes these days to be successful in Sales.

Sales is definitely not this guy anymore:

And, Sales is no longer this slick clean shaven well dressed bro either:

Sales today looks more like this, normal human beings:

Salespeople today are no longer defined under a stereotype. 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 belives in delivering value, in solving problems, in being the best that you can be. YOU can be a salesperson.

Everybody is selling something

Truth is, at some point in our industry, salespeople started to get a really bad rep. And so with the onslaught of incredible access to information via Google, with companies like Dropbox, like Atlassian, and to a certain extent, a huge part of the valley decided “To hell with Salespeople.” Maybe it was the slick Oracle salespeople, maybe it was the used car salespeople, maybe it was both, but we all decided, we don’t want to be lied to anymore.

And yet, it looks like the pendulum swung back in the other direction. With the biggest SaaS companies showing incredible growths, their glimpse into their balance sheets show how a majority of their spend always goes toward “Sales and Marketing.” But this time around, as the pendulum swung back, Salespeople came back with a vengenance.

And the reason salespeople made a come back is because we as human beings realized that even with Google feeding us all the information we need, with all the white papers, and automated nurture campaigns, we still just wanted to talk to another human being. And when a human being talks to another, that, my friends, is when selling happens.

Whether you’re the founder of a company, or you’re a teacher at a parent teacher conference, or you’re a PR person pitching your story to a reporter, you’re selling, and you’re in sales, and you’re doing it with pride, prestige, and honor.

Your Career In Sales

And so with this new definition of a salesperson, if you’re feeling stuck in your career, or are unsure about where you fit, or are looking to take your own development, the amount of money you make, and the amount of value you deliver to the next level, YOU should consider a career in sales. Because sales has changed, and it wants you, the person that emodies the human spirit of being social, of connecting, of helping others and of thriving and building wealth for yourself and your customers. We’re hiring by the way.

If you’re interested in a career in sales, we’re building a massive army of salespeople:
Learn more about becoming a Sales Happiness Officer

How Dyn Uses ToutApp’s Email Tracking and Analytics to Delight Customers

You’d never thought DNS and email delivery could get this exciting. Dyn are the coolest kids on the block making the internet work. They’ve delighted us with their Most Reputable Sender in the World campaign and their nontraditional take on classic internet memes.

When they’re not busy powering the internet, Dyn’s business development and marketing teams use Tout to improve their emails.

Tout is great for “reaching out to existing customers… Since there are wayyyyyyy more customers than there are BDRs, it helps us keep in contact with them all and inform them of other offerings Dyn has.” – AJ Garron, Business Development Rep

As a very customer-centric company (we’ve written about Dyn’s credo and how they put the customer first here), the Dyn team use ToutApp to stay in touch with more customers while keeping the conversation personal. Our templates save the team time re-writing the same communications, and email tracking kicks in to make sure that Dyn’s reps are engaging with the most interested customers.

“Our team loves using ToutApp. Efficiency and 'working smart' are some of our credos here at Dyn, and ToutApp is a major tool to help promote both of them. It's a great connection tool that we use every day.' – John Zahr, Business Development Manager

“ToutApp is a great tool to not only learn how effective you are at first impressions, but also increase the number of first impressions you can achieve in a work day. It makes your emails more about the customers, rather than yourself using its customized templates. If there is one tool in your marketing and sales teams’ hands that is fist pump worthy…this is it.” –Ryan O'Hara, Event Marketing

Tout’s offerings not only help Dyn send out a larger quantity of emails, they also improve the quality of them. Template analytics keep the team on top of their game by letting them know how effective each email is. Not only does Tout help Dyn succeed as a business, it lets them give their customers more of the information they want.

In fact, if you’re a Tout customer looking for your own email servers to send from, we definitely recommend that you check Dyn out. Existing Tout users can set up SMTP with them here.

You can learn more about why Dyn loves us by signing up for a ToutApp account today.

How We Made our Customer Support Kickass

A customer-centered company

Here at ToutApp, we’re really dedicated to making our customers happy. My job title as “Happiness Officer” is a fairly excellent example of thisA month or so ago, though, as we amped up our marketing efforts, we started to experience some growing pains – especially in customer service. We’d been having trouble listening to our customers, responding as quickly as we used to, and making necessary improvements within the app – all while staying friendly, accessible, and helpful. It felt like a compromise to some of our ideals. To that effect, we decided to make some important changes to our support structure that I’ll talk about below.

Though none of this is directly sales-related, I hope that at the very least it’ll spark a discussion about how to best communicate with customers, as well as how to structure customer service at a growing company.

Here are some important changes and realizations we made where it comes to support:

1) “Customer service” is NOT a happy term.

Before doing any real restructuring of our support system, we meditated on our methodology and language for working with customers. “Customer service” is reminiscent of being put on hold and transferred, having to answer the same question over and over, or getting a nine digit case number to reference. Not the sort of experience we wanted to provide to ToutApp customers.

Since we’ve never been fans of doing things the old fashioned way, we’re throwing these terms out internally. If you want to get in touch with us, you can contact the happiness team to ask a question, report a problem, or talk to our enterprise sales team. No fuss.

2) Support tools can actually hurt productivity.

One of the biggest challenges I personally have been up against is the juggling of many different platforms in my daily workflow. At one point, I sat down, mapped out what I was using each service for (it looked something like this [right]), and decided things needed to change.

Here's all the tools I was using for support....

Now I’ve got Hipchat, Pivotal Tracker, Salesforce, Google Docs, Salesforce, and our internal database all hooked up to Zendesk and everything is finally in one place. I know when new cases come in through Hipchat, I can log bug reports easily, record user requests in a spreadsheet, and, most importantly, easily reference our customers’ data while chatting with them. Even if it takes some effort to build a custom setup like this, I can guarantee that the final result is worth it. Your customer support, service, or happiness team – whatever you call it – is not one size fits all. And your internal chaos will likely reflect itself when dealing with a customer. Your zen is their zen.

2) Your feedback mechanisms should be customized.

After a ton of research, we decided to migrate from Desk to Zendesk as our help desk platform.

Ask a Question

Zendesk provided some standard forms for submitting tickets. However, after looking over them we realized these were too generic for our business. So we decided to design our own forms.

Our main reason for this was the need for two very different forms: one that allowed customers to get simple questions answered (e.g. What’s included with your free plan?), and another for more in-depth problems with our product (e.g. Why won’t my templates load?). We’re a fairly complex platform that has a lot of different integrations, so we built up a really comprehensive “Report a Problem” form that asks as many questions as it can so that we can minimize back-and-forth exchanges by grabbing a ton of information up front.

Check them out:

3) Showing is telling.

Our new FAQs!

Throughout this support facelift, it had become fairly apparent recently that we’d outgrown our 

homemade help/FAQ pages, so I completely redid these. Our two worst problems with these FAQs were a lack of up-to-date information and too much text. Rather than spend the necessary time updating these FAQs, I typically ended up communicating one-off with customers to show them a feature or walk them through a necessary process.

I’m cringing a bit as I write this, because we all know that’s not a sustainable process. Investing the time to make your help pages great and create good articles and video content goes a huge way in making any support organization successful. After just a week on our new FAQ pages (using Zendesk’s framework – thanks!), I can already notice a lot more customers educating themselves about the product, which makes everyone’s lives happier.

4) Our customers’ priorities are our priorities.

We previously asked customers “How are you feeling?” in our customer forms. This was a suggestion that Wufoo made at Userconf (a conference that was really helpful in us defining our support priorities!).

In the end, though, we made a basic realization: customers who have to fill out a “Report a Problem” form usually tend to be annoyed – who wouldn’t be?

We wanted to have a more meaningful way of humanizing communication with our customers, so we took a tip from Zendesk and added in a “Priority” field instead. Is this a low urgency issue? Or is it highly impactful? Now we can determine if something needs to be solved right away or in the near future.

In conclusion….

We realized we weren’t scaling something well, so we fixed it. It was this realization that allowed us to create an even better experience for our customers. ToutApp customers can now get help more easily and quickly – with a friendlier face.

I’m sure we’ll continue to have challenges as we continue to scale, but now our revamped infrastructure will better scale with them. If your company is experiencing anything similar, I’d love to talk about ideas, techniques, and tools. If you’re a user, I hope you notice the improvements. We’re here for you guys!

Team of the Week: Ambassador always has their Live Feed running

Our featured Team of the Week entry comes from Derek from Ambassador, writing this on behalf of his sales team. Every week or so, we'll profile a different person who uses our app to improve their email productivity. If you would like to be featured in the future, you can apply here.

At Ambassador, we help companies track and manage customer referrals. We'll let you reward your customers (or affiliates) for referring their friends, family, community, or users to you. Once you've tracked referrals, you can issue cash rewards using our integrations with Paypal and Dwolla. We're a hustling Techstars NYC startup in the one and only Detroit, Michigan. I'm managing our sales and customer service communications.

We LOVE ToutApp because we can see how effective our emails are at educating new customers about our product and its features.

ToutApp also lets us see which attachments are opened, when people reference them, and when they go back to review them. Tout also lets us know that a follow-up email has been read or clicked, letting us know that it was compelling to the recipient. Really useful – I always have my Live Feed running!

User of the Week: David Robinson’s Torrid Affair with ToutApp

I run musician services for a music-ed, tech-startup called Chromatik. I oversee outreach and customer service for the company and am constantly emailing people, telling them about our product and getting them on board. We have been building Chromatik for over a year and have had a tremendous response, including getting the American Idol band, Bruno Mars and tons of schools and institutions to use our product already! 

From an outsiders perspective, one might think we have a seriously unhealthy love affair with ToutApp at Chromatik. And to be honest, the outsider might be right. 

We thoroughly love ToutApp and use it daily in our office for reaching out to potential new users. I blame this torrid affair on ToutApp's email tracking and analytics, especially the Live Feed… not to mention the total integration with my browsers! Emailing has never been easier. We are able to A/B test emails and subject lines that are all tracked and neatly organized – and in return, it effectively helps us grow our company. We're looking forward to using ToutApp for a long time.

Every other week, we'll profile a different person who uses our app to improve their email productivity. If you would like to be featured in the future, you can apply here.

User of the Week: Eric Wu from Bracket Labs

I'm one of the founders of Bracket Labs. We're a Boulder, CO startup building enterprise software apps for the Salesforce AppExchange. Our apps are TaskRay and Campaign Calendar, and together they're helping thousands of sales and marketing people around the world work more productively in Salesforce.

We're a small company, so as a founder I wear a lot of different hats. One of my primary roles is sales, so I spend a lot of time talking to customers who have found our apps through the AppExchange and are looking for more information so they can make a purchase.

I love ToutApp for three big reasons:

1) It helps me do more faster! We have a set of emails we send to new leads to help them understand the apps and determine whether there's a good fit for their team.

ToutApp has allowed me to send (and schedule) my emails in a way that has reduced my time per lead by about 30%.

2) The ability to deliver nicely formatted, trackable follow-up email responses from within the Salesforce Leads tab but sent from my own email address (rather than Salesforce's mailer) is great because I don't always trust the deliverability of the Salesforce mailer.

3) The Live Feed of activity on my sent emails is awesome and gives me new insight on customer engagement with my emails. I can prioritize my follow-ups based on their activity and interest level, timely response to an engaged customer is a big part of showing them you're paying attention and you are ready to help.

Every other week, we'll profile a different person who uses our app to improve their email productivity. If you would like to be featured in the future, you can apply here.

User of the Week: Gavin Pereira from

Hi, I'm Gavin, the director of We specialise in serviced accommodation in London and offer the best selection of Serviced Apartments and Short Stay Apartments for holidays, business trips and relocation. 

We love ToutApp. It's easy to use, and it has significantly helped us increase our email efficiency and effectiveness.

Being able to see how our customers are responding to our emails is extremely useful for our team – and ToutApp makes this possible.

It gives us the tools to improve our email communication and enables us to give a better service to all our customers. We couldn't manage a day without it!

User of the Week: Creighton Green


I co-founded a startup company called Aptivada. We work closely with TV stations, radio stations, and other media outlets to help them quickly grow their social presence. Our apps, tools, and media-specific consulting drives exciting results.


We send a LOT of the same e-mails every day for customer service, sales, and marketing.

ToutApp helps us work smarter, and much faster by providing a suite of tools and features to make sending e-mails better.

We use ToutApp's templates to save time on the daily hours that we were using to write the same type of email over and over again. One of our favorite features is being able to track opens and clicks. This helps us know who we need to follow up with or send another email to. ToutApp is also very simple and easy to implement. Everything ties in easily to Gmail and Outlook. If you're not using ToutApp for your startup or business, you should check them out.

You can get in touch with Creighton through Twitter: @creightongreen

Every other week, we'll profile a different person who uses our app to improve their email productivity. If you would like to be featured in the future, you can apply here.

Should You Send Those Sales Emails on the 4th of July?

First of all, Happy 4th of July. Although we have users using Tout all over the world, we are based in San Francisco, so we decided to take the day off and spend time with our families and friends and appreciate all that this country has to offer.

Nevertheless, for a small upstart like us, there's never enough downtime. So naturally, I woke up this morning and decided to check up on how our systems were performing and how the emails were being delivered.

The first thing I look at is our Tout Happiness Command Center. It aggregates all pertinent details about our business and puts the most important thing up-front — the number of emails being touted over the past 72 hours across our different integrations (which includes Gmail, Outlook, iOS, CRMs and our own web-based app).

Although we saw a bit of a spike early Wednesday morning (our customers outside of the United States ), you'll see that email creation dropped down to near weekend levels as the day progressed.

This got me thinking… 

Is the 4th of July pretty much a dead period of Sales Emails?

So, I decided to dig into the data. Writing emails was one thing, but with ToutApp, you're also able to see and track whether people are engaging with the emails you've sent (we track views and clicks in real time).

The first thing I looked into was the number of “Email Open” events we were detecting across our system and across all of our users. I first looked at Tuesday to see if people started to engage less with your emails when leading into a holiday

As the graph shows, No! People were opening just as many emails the day before 4th of July (by and large) as the past 16 or so Tuesdays before it.

Then, I decided to take a look at Wednesday. Since its still about Noon PST over here, I decided to compare to the past 16 or so Wednesdays but only looking at data for the number of hours that has passed into today.

Surprisingly enough, while there has been slightly less views today than previous Wednesdays, its not wildly off. More importantly, the engagement stats don't represent nearly as high of a drop off for the 4th of July holidays that the send stats do.

So, Are Sales People lazy? Are they missing out on an opportunity to get their message across during 4th of July?

Seeing that people were clearly viewing emails, it bugged me that our customers weren't logged into Tout and sending out emails to their prospects. Were our customers missing out on a great opportunity to get up top on the Inbox?

So I decided to take a closer look at the Email Send traffic going through Tout adjusted for user growth to get a relative measure:

Now if you've been paying attention, you'll know why I got confused here. It looked like very few people were logged in, but we were infact sending a ton of emails out! So then, I ran one more query — which made me one incredibly proud Founder:

Turns out, both were correct.There were very few people “actually working on Tout” but a significant number of our customers were smart enough to make sure Tout continued to work for them even though they were out of the office. Tout customers went in and scheduled a number of emails to be sent throughout 4th of July.

So there you have your answer, you should send sales emails during 4th of July — here are the conclusions:

  1. While people may be at barbecues, fireworks, etc at 4th of July, righ talong with posting their Twitter and Facebook updates, they are continually engaging with their Inbox.
  2. 4th of July is still a great time to continue to move your sales process forward. You may not close deals, but you can most certainly make first contact, grow awareness or move forward in the process.
  3. And lastly, you yourself don't have to be stuck in the office to keep things moving forward. Put automation into place, schedule your emails with Tout.

Are you using ToutApp for your sales, business development and business emails yet?

Here’s 4 Reasons Why your Customers Aren’t Replying

For any company, communicating with your customer base is essential. It can also be very frustrating.

I see this daily with some of our users, whether they’re emailing prospects, current customers, or even potential new employers. Someone will write to us claiming that their Tout analytics aren’t working because no one’s opened the emails they sent. I check and, yes, their emails have been sent. It’s just that no one has opened or responded to them.

All too often, this has to do with the email itself, and I get to tell them: Okay, everything on our end seems to be fine. But maybe your messaging isn’t working? 

Here’s 4 common trends I’ve noticed in their communications and also in my own emails:

1) Your tone is too formal.

How would you write an email to your best friend? A sibling? Parent? Got that in your head?

Now think about how you’d write an email to a current customer or prospect.

If these two scenarios are entirely different, I urge you to reconsider your tone. No one wants to be addressed as “Dear Sir or Madam.” In fact, I’d argue that tone makes emails seem grossly automated rather than appropriately deferential. Keep it casual, keep it light, and keep in mind you’re a human talking to other humans.

2) Your email is too long.

No matter what you’re saying to your customers, it should not take two pages of text to say it. So if you find yourself saying the same thing over and over again in an email, stop. Eliminate redundancy. And move on. If you feel yourself getting particularly verbose in your writing, more often than not you’ll likely need to take a step back and assess how to best cut down on your extra words.

3) You’ve got large blocks of text.

I’ve separated this blog entry into different items so that you’re not staring at a huge page of text with no breaks. Try to do something similar by breaking paragraphs often or making lists:

  1. Put yourself in the mind of the customer
  2. Create a process for them to follow
  3. Order this so that you are providing an organized breakdown of a list for them

Also, don’t forget to bold important pieces of content so they don’t get lost.

4) You’ve forgotten a call to action.

What are you trying to get your customer to do? It’s important to make this call to action pretty clear from the start and crystal clear at the end. Signing off on your emails with a “Just wanted to say hi….”, a “give me a call if,” or similar is a weak call to action that requires too much effort to act on.

Instead, ask your customers if 12pm on Tuesday works for a call to talk to them. Send them a link to a relevant article. Offer them a special deal or a walkthrough of your product. Include tracking links (we generate these automatically when you send emails through our service) so you can see how well each of your calls to action work.

I hope this helps! What other tactics have you found to increase engagement through your communications?