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


20 things you can do to shake up your workday

Since it’s Wednesday we figured you need a break. Hump Daaay!

Here are 20 things you can do to take a break from email:

1. Buy and train a puppy

Image Courtesy of @pugsofinstagram

2. Start happy hour an hour earlier

Image Courtesy of Movie Fan Central

3. Take a nap

4. Close more deals than Chuck Norris (Let’s face it…not possible but give it a try)

5. Have time to wait in the Starbucks line at 8am

Image Courtesy of The Dark Room

6. Get in shape, take up a new sport, or try prancercise

7. Take a two hour lunch break… and just not come back

8. Call the people that actually care– like your grandma (just kidding.. people on your Live Feed)

9. Rent a tiger (yes this is a real thing)

10. Spend more time prospecting at bars

11. Join a skeeball league

12. Watch Game of Thrones. Challenge yourself. 1 whole season in only 1 day.

Image Courtesy of UPROXX

13. Re-read Harry Potter

Image Courtesy of The Huffington Post

14. Get a confidence boost. Check out the “who’s viewed my profile on LinkedIn.”

15. Learn to code. Thank you Atlassian for the spooning tips

16. Take the muni to work.. not Uber, Lyft or Sidecar

17. What the heck – Get on the wrong line bus line. (hop on the Google bus and try to use your muni card)

Image Courtesy of SFGate

18. Rent a scooter or if you live on the wild side… splurge on a segway

19. Take a break from email.. send a fax

Image Courtesy of

20. Watch this Hump Day video! 

Now get to it. ToutApp actually saves you time on email.

Don’t believe us? Check it out here


7 Ways to Get out of your Sales Slump

I had a bad sales month last month.  After a handful of losses on a Wednesday evening, I cried. What a wimp, I know. After a brief moment of utter disbelief and hurt I wiped the tears away and took a step back to reflect. What did I do wrong, what did I do differently from the previous month? For those who have lost a big deal or are just in a sales slump here is the breakdown that may assist in your sales ventures.

Step One: Stop Crying Ya Baby



Me Circa 1994

It’s only a deal not the end of the world. Pick yourself up, dust yourself off and try again. Take each loss with a grain of salt. Start with each step of the sales process – critically think about the conversations you had and the process of each sale. Start over and try new approaches on your next sale.

Step Two: Care about your prospects

Did you take at least 5-10 minutes to research that individual or that company? Do it now. Jump on Linkedin and get after it. Improve your cold emails with a touch of personalization, insight and value.

I absolutely loved John Barrows article “News Flash – your prospect doesn’t care how awesome you are.”

When prospecting, do some research and find something interesting to reference about a client before calling them and use that as an intro.  When meeting with clients, ask open ended insightful questions that put them in the position to be an expert. — John Barrows

Beyond the research, how are those emails performing? Are you monitoring analytics around the types of messaging that resonates to each customer?

Best Practice: Use Tout to get more insight around how successful your day to day emails are. Check out the engagement on this puppy…



Benchmark your templates to get above industry standard.

Rough average: 20% open rate & 5% click rate

Step Three: Be Smarter about your Follow-Up

It sounds so simple. So easy and it is. Just follow up. Following up can be the most underrated piece of the sales process. You have more than enough leads you can handle how do you balance follow up and remember all the customer specifics? Be smarter about your follow up, time follow up and make sure you are consistently hitting them up every 3 – 4 days. I’d recommend leveraging auto follow ups with Tout. Best Practice: I got this one from Doug Landis @ the Sales Hackers conference. Track everything. Track the messaging you are using and track the responses you get through email and over the phone. Track and learn what is working and what needs to be refined.

Step Four: Be Human

Above all… Be human. Ask about their day or weekend. Care.

Humans don’t buy from companies, humans buy from humans.

This is what we live by at ToutApp, our mantra. We solve real life problems for salespeople. We teach first and then we sell.

Step Five: Zip it and Listen

Want to get off the phone with a prospect and have them think “Wow, what a great call”? You must LISTEN. I will be the first to admit, I love to talk. Who doesn’t want to talk about themselves. But the more you listen, the more you learn, the more you can critically think about how you are going to solve the customers issues they have articulated on the that call. Take notes. You want your prospects to adore you, trust you and respect you… shut up and listen.

Recently, I was on an important call with our Chief Happiness Officer, TK. He, taught me something so incredibly powerful that the average company may lose sight of. He said, “Let’s forget about Tout, let’s talk about what you need to make your customer/team successful – what can we do to help them?” Or even ask your potential client the simple question, “What’s important for you right now?” You should never sell first. You teach, you listen and you build trust so your potential customer will want to partner with you. You are there to solve a real person’s issue at that moment.

Step Six: Promote Success and Happiness Above All

Sure – you are in sales, you should be selling. But what is selling without creating some type of success and happiness for the buyer? Customer success and happiness is key to your success. If your existing customers are not happy – you are doing it all wrong my friend. Keep in touch, check in, send a birthday card or company t-shirt.



Keep an honest relationship with your customer. Happy customers will bring you a long term partnership and potentially add-on sales. If your customer is successful then you are successful.

Step Seven: Don’t Give Up

Everyone has a bad day, bad week, bad month. Move on… get over it. Don’t give up.

Failure is just your judgement on an experience, because there are no failures, just learning opportunities. — Aaron Ross

The most successful salespeople learn from their mistakes and improve year after year. Learn from your bad days. Always try to be better, be the best of what you do whether you are selling carpet or an email solution.. give it all you got.

Questions, tips or tricks? Feel free to reach out anytime:


Happiness is not just for clowns. What it’s like joining Ronald McDonald as a “Happiness Officer”

When I think of McDonalds a few things come to mind. Big Macs and Ronald. While Big Macs make people incredibly happy– Ronald McDonald is actually coined as the company's “Chief Happiness Officer” over the burger.

Why do I love my job?  I get to make people happy. Here’s a roundup of my week so far patrolling Tout and San Francisco for happiness.

I get asked a few times a day “Are you serious? You’re a Happiness Officer!” Yes, that’s my real title here at ToutApp. I’ll even show you my business card or you should check out my LinkedIn. You can even apply to be a Happiness Officer with me. Often I conceptualize my title in a number of ways including customer success, sales, taking away the pain of email, helping sales teams leverage an awesome tool, the more common known Account Executive and so on…

Today I decided to keep simple and take on the literal role of a Happiness Officer. The decision sparked after recently signing up for Gretchen Rubin’s “Moment of Happiness”, where she sends me a quote everyday to deliver a dose of happiness. (I admit.. I am one of those folks that actually gets a kick out of motivational videos, quotes, posters and books)

Here’s a freebie for you
The true secret of happiness lies in the taking a genuine interest in all the details of daily life. –William Morris

As a Happiness Officer I’ve been taking mental notes of all the little acts of kindness I’ve observed right in the heart of San Francisco. It is my job after all to patrol Happiness. Here are just a few I’ve jotted down.

My Top 5 Little Moments of Happiness

1. PostMates ( a great delivery service) just came into the Tout office. “I have a delivery for Ali.” She opened up the bag to find that Joey The Cat sent her a get well soon package. She mentioned she wasn’t feeling well as an afterthought to him this morning.

2. I typically go to the same few places downtown for lunch. I ran out for a late lunch this week to one of my goto spots– Mixt Greens. (It was one of those days– a rough day is the best way to describe it. Those days when a silly sequence of events happens like missing the bus twice or a call doesn’t go as well as you hoped) Right after I paid, one of my favorite employees reached over to hand me a lemonade. It was such a simple gesture, but seriously made my day.

3. Coffee and a date. Jen made her daily trip to Starbucks only to double her order one morning. Instead of her usual iced coffee she brought a homeless man in need a cup of joe. His response— will you be my girlfriend?

4. This one goes way back. During my first day riding the bus after I moved to San Francisco I didn’t have all the pieces put together. I probably should have Googled “How much does the bus cost in SF?” Instead I got on the bus and realized I didn’t have the $2 fare. I was scrambling for change as the bus was moving and a guy who was waiting with me at the bus stop just a few minutes earlier reached out and put $2 in the machine.

5. Going through my inbox and finding an introduction from a Tout customer connecting me to one of their friends or coworkers. Thanks guys! I really do love referrals and appreciate you spreading the good word. 

Hope this brightened up your day. If not, happy hour is only a few hours away!