Video | The #1 Skill for Founders and CEOs

Despite having the CEO title, your job as the head of a company is to be the greatest Salesperson for your company to investors, employees and customers. In our first episode of Manager Playbooks, TK discusses what he thinks might be the most important skill for today’s CEOs, and gives some examples of how that skill played a role in ToutApp’s growth.

Check out the video here:

Any followup questions for TK? Post them below!

Tout Tips: Social Selling Talk with Meghan O’Donnell

What is your definition of Social Selling?

I’d say that Social Selling is about having a professional presence on social media and also having an awareness of what’s going on. You don’t have to be engaging all the time, but having a persistent professional presence on a few social channels to keep in touch with prospects or opportunities is the key to Social Selling.

Which social channels do you use in Social Selling and how do you use them?  

Professionally, I use LinkedIn and Twitter.

On LinkedIn, I connect with every person I have a conversation with or meet in person. Some people are picky about who they connect with, whatever is right for you go for that. And don’t forget to write a personal note, even if it’s simple. Taking the time to personalize your note will go a long way. Over the years, LinkedIn has changed their UI and now they make it effortless to stay updated with people when they get a new job or a work anniversary.

On Twitter, I’ve seen a lot of success and have developed a large number of relationships by RTing, commenting on tweets and thanking people for sharing content. Those activities have turned into great relationships and friendships where we’ll DM (direct message) each other and stay on each other’s radar.

How did you get involved in Social Selling?

I had just started my career in Sales and Koka Sexton came into the ToutApp office and did a training on Social Selling for our small team. At the time, I only had a LinkedIn for my digital resume and barely used Twitter. Koka’s training was inspiring as he told us all about Social Selling, how to stay relevant and told us how he built his social presence.

As an internal ToutApp fun fact, I also started on Social Selling because I wanted to get more followers than Daniel Barber. Between Daniel, myself and two other reps, we had an internal competition of who could get a hundred followers in a day, then a who could break a thousand followers, etc.

As Sales moves towards an Inside Sales model, how do you think Social Selling is bringing back the 1-to-1 communication?

I think in our generation, social media is huge–with Instagram and Facebook, we’ve been conditioned to update those personal networks and engage with other people’s updates as well. Since staying connected is a huge part of our personal lives, bringing that mentality to a professional setting is transferrable. On these professional networks, a new sales rep can learn a lot and gain a lot of valuable insight without having to have 1-on-1 communication.

Social Selling allows you to get to develop relationships that you’re not able to make just by talking business on the phone or right after a demo. When you’re able to go onsite and talk to the team you’re selling to–people are more likely to open up and you can interact them easier, and so Social Selling gives you that 1-to-1 insight and allows you to have outside conversations.

Many people aren’t fans of the term Social Selling, what’s your take on the term?

I don’t mind the term, but for my strategy it’s not about selling. I utilize these platforms to build relationships, understand people’s priorities, and be social. And so, if opportunities come in later or if there’s a way to leverage those relationships, then the selling part comes in.

How do you fit Social Selling into your workflow?

Having the right tools to help you stay updated on the topics you care about is really beneficial to keeping Social Selling part of your workflow. Blocking off time at least once a day to go through your Twitter feed to read, comment and share is a great process. The third thing I do is whenever I get off a phone call with someone, I connect with them on either LinkedIn personalize the message based on our call.

Even before calls, I use LinkedIn to research who I’m about to talk to on the phone and I look at if we have mutual connections or where they went to school, etc. I bring the information that I find on LinkedIn into my calls and sales cycle.

Any final tips for people who want to get started on Social Selling?

For all the social channels that you decide to use professionally, you should have the same handle and picture across all the channels. This goes into building your professional brand and makes it easier for other people to find you.

Lastly, tell me why you’re Meghan “Oops I Close Deals” O’Donnell.

When I was an MDR and I’d always ask if I could close a five-seat deal because they were ready to buy ToutApp as an inbound lead, so TK started calling me Meghan “Oops I Close Deals” O’Donnell. Then we all went to New York in April 2014, and TK spoke at the Sales Hacker conference and we all wanted to live tweet the event–so I created a Twitter handle and landed on @oopsiclosedeals.

Humans of Tout: Meet Nick Feeney and Learn his Sales Journey from MDR to AE

We talk a lot about what it’s like in Sales. I mean, we’re a Sales Acceleration Blog. In this edition of Humans of Tout, we get into the knitty gritty of what life is like on the ToutApp sales floor. Nick Feeney, a Sales Happiness Officer, talked to me about what his day-to-day entails, how he lets off steam, why he gets into the office at 6am and what he eats (at his desk).


What made you choose sales?

The challenge and the fast-paced change is why I chose to work in sales. No two days are the same. Sales provides a thrill for victory and passion. I’m not only competing with myself to be successful, but I’m truly surrounded by some of the best in the business that push me to strive for excellence. My peers and prospects not only elevate my sales career and integrity each day but also bring me back to reality around how to make a positive difference.

Every interaction I have with a potential customer contributes to developing a trustworthy relationship by not only being a trusted advisor but being genuine in my approach. The root of it is, I’m truly excited about what my accounts are doing, which is constantly looking for the next best thing to elevate their team and work to solve their challenges.

There is no defined timeline for building relationships. Too often, sales folks are impatient in exercising patience. One of my mentors always told me that you may not win much business in your first encounters, though you can certainly lose a lot!


What brought you to ToutApp and what’s it like to work here?

In my previous sales roles, I felt extremely stagnant with minimal room for growth. There wasn’t a constant challenge to improve my sales tactics and methodologies. I had a mid-twenties crisis and I knew I had to get out. What drew me to ToutApp was the people and the culture. Before joining ToutApp, I was ignorant about the tech space and how a startup like ToutApp, with a mere 10 employees, could be such a powerhouse. I wanted to be an influential part in a company’s growth and vision. I was and still am passionate about growing alongside ToutApp as a sales professional. I’ve been here for a quick year and I’m a completely different salesperson than I was twelve months ago.

A job at ToutApp is as rewarding as you want it to be. Like any other job, the amount of effort that you put in is what you’re going to get out of it. The reason I get out of bed (at the crack of dawn) is because my peers, management and overall team drives my passion for success.  I’ve been fortunate enough to call some of my co-workers my best friends. It’s the culture, it’s the atmosphere, it’s the excitement – it’s what makes you want to crush it.


Nick at our Dreamforce 2014 booth. 


How would you describe your job?

I’m a Sales Happiness Officer and I’m actively building relationships with new people. It’s like convincing someone to trust me with their newborns because with sales management, their reps act as their kids Monday-Friday.

My goal is to be that trusted advisor for that “family” so they can grow and solve their needs with what we’re offering. Building the value by providing a genuine  partnership rather than just a tool.


We’re growing really quickly at ToutApp – how does that change your day-to-day?

The growth has been non stop craziness, but extremely exciting. I see a lot of myself in the new reps that have hopped on board the ToutApp train, as I started as a Market Development rep myself back in June of 2014.  Like any other startup, when I first joined we were constantly changing our process, with a minimal idea of how to streamline success. Since then our company has grown tenfold and are continuing to propel our business daily. Those starting today are more armed to be successful based on our previous shortcomings and success that we’ve built out. It’s exciting to see the company grow because you never know with startups, it could be gone tomorrow. The beauty with ToutApp is we all have the same vision and believe in the same end goal.


How has ToutApp changed your selling process?

I’ve always been detailed oriented and on top of my work, though I came in to a rude awakening and a radically different workflow from what I was used to when I joined the company. ToutApp has forced me to think more strategically, not to assume and truly understand a persons needs before addressing mine. I’ve learned to listen to an answer, digest it before regurgitating and thoughtfully clarify, adjoin, funnel and elevate my response.


What are some of your proudest accomplishments?

Proud accomplishments are tough for me to relay. I think my proudest accomplishment, which I’m continuing to build is my portfolio of incredible teams I’ve been fortunate enough to partner with. It’s exciting for me to make an impact on not only a rep but at an executive level. The product I sell allows for me to have confidence. Confidence in not only my abilities to be a successful sales professional, but confidence in how this platform can positively change careers and level up performance.


You get up early, what’s it like being an extreme morning person working in the sales startup space?

If I could sleep until 3pm, I’d order in every meal and call it a day. In all seriousness, I check my email at 4:30am and I pray to the holy sales gods that I have a DocuSign waiting in my inbox or a fresh Starbucks breakfast sandwich on my bedside — usually neither of those magically appear. Instead, the MUNI suffices to schlep me into the office around 6am to get things done.

I need to get in here early to manage my day. I’m a walking stress case, so if I feel that work is overpowering me and has control over my day-to-day – I can’t be successful or productive.

My goal is to simply stay diligent, limit distraction, blast country music and do better than I did yesterday.


What would you tell yourself eleven months ago when you first started?

When I first started my sales career, it was easy to follow a method of untrustworthiness. Just lie through your teeth until you can close the deal. At ToutApp, we’re selling to salespeople and that method doesn’t work.

Previously, I was in Fitness sales, selling memberships in a face-to-face, transactional way. I was selling to every consumer, from a teenager with a dollar in his bank account to a nurse who was training for her Cabo trip.  Now, I’m fortunate to sell to executives that I aspire to be like. I’ve learned to be transparent and ask the tough questions.


An anonymous admirer sent Nick M&Ms for Valentine’s Day this year. 


What do you do to let off steam?

I work out everyday at 4pm. I have to block off my calendar and get out of the office. I’m sure we can all relate that after sitting at our desks for 10+ hours, we begin to translate our sales pitch in pure gibberish. Letting off steam and sweating out your frustrations in the best way to clear your head. Truth is, I’m also a violent cookie eater, and nobody wants to see what I’d look like if I didn’t work out.


Nick Feeney is an Account Executive or Sales Happiness Officer at ToutApp. Follow Nick on Twitter @Mr_NickFeeney and connect with him on LinkedIn.

How ToutApp Helps Me Help Others

At ToutApp, the Happiness Team is working hard to create an unparalleled customer experience. After a team decides to adopt ToutApp, we as Customer Success Managers are looped in to make sure they are successful. As CSMs, our goal is to help sales teams optimize, create more efficiency, inspire creativity and boost connection in their day to day. We want every customer to get more out of our platform, and more out of themselves. Here’s how we do it:

5 ToutApp Hacks I Take for Granted

Calendar Sync

CSM’s here at ToutApp are responsible for the success of every team that joins. From offering trainings and on-site visits, to hopping on calls to discuss renewals, our calendars can get crazy.

Often, I am juggling 80+ accounts and it can be hard to gain control of the my calendar.

Customer: Do you have time next Wednesday to teach me the 5X5 method?

Me: Let me see…

When trying to find a time that will work for a training call or even an internal sync, the calendar feature in Tout keeps me from goofing up.

  • Calendar sync functionality allows me to pull in times I am free for trainings, support calls, quarterly reviews and even internal brainstorms with just a few clicks. Calendar sync helps by cutting back on all the back and forth and preventing me from double booking myself saving me minutes off every email.

Email Templates

A big part of being a CSM at ToutApp is knowing how our customers are doing with adoption and ensuring each team is getting the most out of the platform. Instead of simply looking at the % of actively users, we go above and beyond by truly understanding how our customers are selling and where we can help. I’d much rather spend my time talking to teams and learning about their company goals than getting stuck doing anything monotonous. Templates help me focus on what’s important.

Just today I used a template to send resources after a training call, for a reply to direct someone to utilize our knowledge base and I even used one to close an upsell.

  • Templates are an amazing way to pull in baseline messaging so that I can spend my energy in more productive ways, like learning more about my team’s specific sales cycles, workflows, and needs. All I have to add is the personalization. Templates for NPS surveys, templates for training resources, templates for renewal notices, templates for check-ins – I can’t imagine starting every email from scratch anymore.

Group Emailing

Now, the only thing we love more than meeting our customers face to face, is meeting our customers face to face at a HAPPY HOUR. And while they are always a blast, they don’t happen without some coordination and planning.

How do I invite my team’s to celebrate with us without spending hours writing emails? How do I reach out and notify all of my account in a personalized friendly way? Group Emails. Drop mic.

  • Sending group emails through ToutApp allows me to send personalized message to individuals in my key accounts in a matter of minutes. Whether I am sending a follow-up after a training call or sending a personal invite to one of our infamous happy hours, group emails save me hours of time.


There is a lot to do post-sales to keep the magic alive. From making sure teams are setup properly, trained, to the eventual renewal, it can be difficult to stay organized. As most CSMs will probably say, being proactive with accounts makes all the difference.

Staying five steps ahead can be tough but guess what, ToutApp helps me here too.

  • Reminders help me ensure nothing falls through the cracks. Setting myself reminders post training to follow up with teams in a week or two has been been invaluable. Reminders to reach out to renewals a couple months in advance and reminders to send ToutApp swag and “I Close Deals” shirts to our kickass customers help me level up my CSM game. Plus, nothing is more satisfying then checking that little box and seeing my productivity soar.

Live Feed

The Live Feed is not just for sales. CSMs at ToutApp benefit from knowing when someone has engaged with our emails for many of the same reasons as sales reps do. We’re just as hooked as our fellow colleagues.

Not only do I see my reminders in one place but I am notified when my own team rings the gong and updated in real time when someone closes a deal. Let the fireworks ignite!

  • Having insight into which resource emails my recipients have opened and which guides they have clicked through tells me who is engaged and who needs some extra nudging. In addition, when trying to get a renewal signed off persistence can be key. The Live Feed helps me time my follow ups to get the right person at just the right time.

I could keep going with these ToutApp pro-tips but I don’t want to give all my secrets away. After all, in my opinion, closing deals requires some science, some art, a dash of magic and a Happiness Officer waiting on the other side. But don’t fret, this is not the end.

If you want to learn more you can check out our Knowledge Base and level up your own Tout game. If you want to know how your CSM team can use ToutApp, talk to one of our Account Executives and if you have any questions, were just a click away! Write in and we’ll respond, it might even be me!

And as always, Happy Touting.


If you love ToutApp and want to work with a kickass team, we’re hiring! More on how to join the fun here!

A Shout-out to You from ToutApp!

It’s that time of year again and we’re kicking off the holiday season a bit early this year, and wanted to give a huge shout-out to you. Yes, you—our amazing customer community.

Next week is Thanksgiving and the official start of the holiday season. Across the country, friends and family will gather around a table to share memorable moments from the year, have a good ‘ole time and say thanks to the people that mean the most to us. We here at ToutApp are no exception.

It’s no secret that that entire team at ToutApp loves our customers. We’ve even made a page on our shiny new website dedicated to you–that cutting edge sales team. As a Tout customer, you become a card carrying member of the Tout nation and a true voice in our company mission, product features and every day #toutlife. We’ve hosted customer dinners, happy hours, workshops and networking events all for you. Because you’re simply the best.

Welcome to The Closers Club, it’s for those who close deals.

One of those inaugural members of The Closers Club is the entire sales team at Kareo, an electronic health records company that streamlines everything from billing to collections for thousands of doctors’ practices nationwide. Headquartered out of Irvine, California–this team of closers are truly exceptional.

When Rick Palmer, the Sales Operations Manager at Kareo was continually faced with productivity and messaging roadblocks for his sales team — he found ToutApp to be his solution. Read more about the Kareo sales team and their story on how they supercharge productivity here or click the image below.


So, in short, here’s to you. We hope you have a great start to your holiday season and bring on home those deals well into the new year, because we’re all closers here.

The Best Sales Training I Never Knew I Needed

In preparation for this year’s Dreamforce conference, Sales Happiness Officer, Jess Green shares her reflections and lessons learned at last year’s Dreamforce. It also happened to be her very first day at ToutApp.

There are so many different sales training methods and strategies on how to ramp a new rep. I now believe I’ve experienced the best training a sales person can have Week One on the job — manning a booth at Dreamforce, or better yet, TWO booths!

Talk about jumping out of your comfort zone to allow yourself to truly grow. I experienced this first hand! I left a fantastic company that I had been very comfortable with over the past 5 ½ years. As I’m sure every person does when they start to consider a career move, I weighed my options of being “comfortable” and successful at my current company against taking a risk that could lead to even greater financial and personal success. I made the leap. And when I did, I didn’t realize how much I would enjoy not only getting my feet wet the first week but diving in headfirst and not looking back.

My first day at ToutApp was on Friday, November 15, 2013. I figured with the presence and buzz ToutApp had for the upcoming Dreamforce conference, I knew I couldn’t pass up the experience to be a part of the team as they launched into the week.

Here are the 3 best training tips I have for your 1st week, whether it’s in an office or at this year’s Dreamforce.

1. Listen, Do, Reflect, Iterate

Take in as much as you can when listening to the team around you. This really applies to everyone, everyday. You never know when you are going to hear in an interaction that changes your perspective or is an “Ah-Ha!” moment of understanding. It could become the secret sauce of your sales process!

2. You don’t have to know everything

You JUST started, put your best foot forward, be confident, and when you don’t know an answer give yourself a break. Take note of the question, promise a follow up and here’s the big one…actually follow up!

3. Build relationships

In the end isn’t that what sales is all about? If you don’t know everything about the product get to know the people you chat with and what their challenges, goals, and focus is day to day. Once you finish ramping up you can apply your new knowledge to the conversation you had previously and I’m going to bet that relationship goes a lot farther than it would have if you just spewed feature after feature at them.

All I can say is, what a week! Remember these are not only key tips for week one but remind yourself throughout your career. Good luck to all of those who are currently in transition mode, I hope this helped :)

How did team ToutApp achieve a 72.2 SSI score in Social Selling?

Recently at the LinkedIn Sales Connect conference, we were rated as the #1 Social Seller in the SMB space with an SSI score of 72.2.

Naturally, ToutApp’s name was buzzing, and we kept getting asked “How do you do it?” Well… to be honest, our first natural answer was — well — we don’t know. So we took some time to reflect.

Isn’t selling, by nature, social? Well, yes. All selling is social. That’s just how things are and how they’ll always be.

Before Twitter, LinkedIn, Facebook, and the dawn of the Internet age–people were selling socially. Believe it or not, people talked to one another, often face-to-face and sold things to one another.

Goodbye to the days of selling magazines door-to-door and hello to a world where if you’re game isn’t social selling–you’ll be left behind. We, as a society, cannot buy or sell without being social. It’s just not possible. Customers, either happy ones or disgruntled ones, seem to be much more vocal over the Internet. In our super-connected world, it’s easier than ever to start social selling. Do it now.

#0 – Embrace Social

As we reflect on things, the first thing we realized was that the majority of the company was on social media. Social is part of our culture. At ToutApp, we believe in the power of social selling and it’s one of our key selling strategies. Meet Taylor Miller (@taylortsm), Nicolette Mullenix (@NicoletteToutIt), and Meghan O’Donnell (@oopsiclosedeals)–three stars of ToutApp’s social selling strategy as they give us pointers on how to socially sell.

#1 – Post Real Content, Not Fluff

Early on, decide who’s your target audience and zero-in on their needs and pain points. People are smarter than they’ve ever been. That also means that they’re more aware of their time and the only way to reach them is to provide clear, resonating value and content for them via social channels.

#2 – The Huge Power of 160 Characters

We all know that Twitter has 140 characters, but did you know that your Twitter bio is limited to 160 characters? You only get 160 characters to tell people how awesome you are–that’s not a lot of room. So, be economical yet authentic with your micro-bio.

Your Twitter bio should be compelling and outlines your goals, values, and transparently showcase what you’re selling–whether it’s a service, product or coffee. Like your Tweets and blog posts, your bio should target a specific audience that you’d like to converse with via Twitter.

#3 – Showcase the Professional-Personal You

Twitter is a superb platform for social selling. It’s also a great place to rant about your city’s public transportation system. It’s your job to know where to draw the line. Instead, create a Twitter account that carefully balances professional content (company blog posts, industry practices, etc) with a healthy dose of personal content.

Got a fun office vibe? Tweet about it. Did you go to a meetup for tech salespeople? Tweet about that too. But, don’t just tweet willy-nilly. Remember to use proper netiquette and always contribute value.

#4 – Highlight uncommon commonalities

If you’re sending a cold @mention Tweet or email, it’s hard to get the conversation going. Make a stronger connection with prospects and emphasize something uncommon that you two have common.

Do less “we’re both in sales” and more of “we’re both avid swing dancers.” Whoever you’re reaching out to is more likely to respond to that quirky, personal connection rather than the general shared profession connection. I know I would.

#5 – Team Collaboration for More Thoughtful Leaders

At Tout, we use HipChat to talk, share ideas, and work together. By virtually sitting in one chat room together–we get a lot done. HipChat makes it easier for us to share and gather information on customers and share news about prospects.

Beyond a chat room, we also social sell across our entire team. Everyone has the responsibility to be a voice in our social selling strategy. We work as a whole team to share company blog posts and Tweets across our own professional networks; which leaves impressions on a wider reach. Every person at ToutApp is a thought leader and together we’ll make a larger impact.

#6 – Tools for Social Selling

Ok, now you’ve got the how-to, here’s the know-how. Keep TweetDeck open on your desktop to track @mentions, #hashtags, and your Twitter Feed.

Create Google Alerts to monitor the entire Internet for interesting and sales relevant content.

Buffer is a great application that’ll queue your tweets and posts. Just line them up in advanced and you won’t have to worry about them later.

There are so many sales opportunities through social media. Be sure to use them all to your advantage.

Want More?

Social selling is huge. Some of it is a fad, and some of it is here to stay. We’ll be digging in more into the topic and sharing more tactical advice in the coming weeks. So, stay tuned!

If in case you want to learn more and just can’t wait, be sure to check out our post about the time Koka Sexton came to ToutApp and dropped a knowledge bomb on social selling.

What’s better than a cup of coffee to start the day?

Three months ago, I started a new sales job at a disruptive software company. As with most young startups, the workday typically extends beyond the standard 9 a.m. to 5 p.m. In my current role, I usually get into the office by 7:00 AM and sometimes find myself there until later in the evening. With my past employers, I was usually able to dedicate my evenings to exercise. However, in my new position I found that I was making countless excuses to skip the gym after a long day at the office.

A lot of us struggle with a work/life balance, especially in the startup world where every ounce of output is valuable. Exercise had always comprised a central tenant of my life, but it seemed as though there was no way I would be able to incorporate it into my daily routine. However, there was a solution out there that I was originally hesitant to consider: exercising before work. I was committed to maximizing my health, happiness and productivity – so I took the plunge with a 30-day challenge.

The Challenge #earlydaysfor30days

My challenge is “Early Days for 30 Days” committing to a 4:30am rise Monday-Friday and hitting the gym.

The Preparation

Although it took me two weeks to lay off the 4:30am alarm, I finally started my challenge last Sunday by preparing everything for the next day; such as laying out my exercise clothes and having my clothes and toiletries already packed. When my alarm went off at 4:30am on Monday, I put my workout clothes on, laced up my shoes, and hit the gym!

The Results

Turns out Isaac Newton was right! Objects in motion really do stay in motion. A week into my challenge this is what I’ve found:


Fitness Endurance and Agility
As long as I prepare the night before, I have minimal excuses to skip the gym in the morning. My endurance is increasing and I’m pushing myself to my limits. After one week, I’m already seeing physical results by adding 2-3 extra days at the gym per week.
Boost in Productivity
When I get into the office at 6:30am-7:00am, I’m already stimulated from my workout and am ready to start work as soon as I sit down. Rather than waiting for that first cup of coffee to kick in, I have at least 30 minutes back in my day when I arrive at the office.
Encourages a healthier diet
Typically, after exercise you reach for the banana and yogurt rather than a Starbucks Caramel Macchiato and breakfast sandwich with cheese and bacon. Morning exercise sets the tone for the day and encourages healthy eating throughout the day. Skip the Snickers bar and go for a handful of almonds!
Better Organization
Personally, I’m more alert and sharp in the mornings. Getting my endorphins going in the morning allows me to create and complete more to-do lists. I start planning my day out in my head while I’m running so my day feels organized by the time I arrive in the office. I’m a big proponent for checklists, and exercising in the morning has lead to faster completion of those lists. Always a rewarding feeling!
It’s contagious!
When I started the challenge, I mentioned my early morning challenge to some coworkers. Within a few days, there were at least three others who had started exercising before coming to the office. Just yesterday, eight of us completed the J.P. Morgan 5k Corporate Challenge and we’re ready to enter another race. I encourage you to challenge yourself whether it be a fitness challenge or another types of challenge and see if it helps your work/life balance.

Follow me along my #earlydaysfor30days @NicoletteToutIt

How to Build a Team of Sales Superheroes

Dear Brittany ToutApp

Dear Brittany,

Our start-up is really getting some traction – yee ha! Now we need to bring a sales superhero on board, and I’m not sure how to separate the wheat from the chafe? I’ve made bad sales hires in the past where they show and tell me how amazing they are, and then they don’t close a single deal…sigh!

What should I be looking for? Is there a way to “test” them to see what real skills they’ve got? Any other tips hiring for this kind of role?

Many thanks,
From Start-up taking off!

Dear Start-up taking off,

I sat down with our VP of Sales, Eileen Wiens, and our Director of Sales Operations, Daniel Barber. Both have years of Sales interviewing experience; and have managed multiple teams.  In fact, both interview candidates on a daily basis at ToutApp– they’re perfect for helping answer your question.

First and foremost, they both agree you should know how to sell to your uber driver. In other words, before you bring on a salesperson, make sure you can sell the product yourself. You’ll know what type of language you’re looking for in the interview, and will be able to define your product. So here’s your answer for how to hire an amazing salesperson…

Where do you start?

Know exactly what you’re hiring for. Eileen says, “Are you looking for hunters or farmers?” In other words, do you need someone qualifying or finding leads, or do you need “closers” or reps that can work on Enterprise accounts. It’s important to first understand each role and your sales cycle (transactional one-call close vs. complex 6-9 month cycle), and only then, will you know what your perfect candidate looks like. “You need to find the type of person that fits the type of sale that you have, it may evolve from SMB to Enterprise, but know what you need.”

Types of questions to ask.

You’ll want to be able to separate the great interviewers from the people that can actually execute. Eileen likes using layering questions, and pulling away the layers for each answer. An example might be:
Q: Describe to me your sales process.
A: After a lead, I do a demo.
Q: How do you get demos? Are they inbound leads?
A: No, I have to prospect
Q: Tell me how you prospect? How do you pick who to call or email…

By asking open ended questions, you’ll get to see a candidate’s strategy, clock-speed, and thought process. How deep can they go? They should have learned a lot about their product and know how to explain it to you in layman’s terms.

With beginning roles, you’ll want to focus on personality characteristics like grit and persistence. For experienced reps (5+years), it’s really about knowing how complicated of a sales process they’re capable of managing. Eileen tells me, “If there are Stakeholders across 3+ departments before we even get a trial off the ground; it’s about knowing how to navigate and piece together org structures and understanding all of the groups with keeping the sale in mind.”

More Sample Questions, and what you’ll learn.

-Aptitude: Sell me your last companies product.
-Passion: Lately, What are you doing to develop your sales profession…books, blogs?
-Ownership: Tell me about an early time where you had to demonstrate responsibility.
-Experience (for seasoned sellers): How did you manage your sales cycle?
-Consistent Persistence: How many times do you think it’s worth following-up with someone? Hint: Most people drop after 5, be that sixth! :)
-Critical Thinking: How is selling door-to-door similar to this role? Have them tell you how they would get someone to open the door for you (over the 200 other people ringing the doorbell). Hint: the inbox is the modern day doorstep.

Interview Style.

You’re going to be shocked to hear this. You’re doing it all wrong. Daniel, our Director of Sales Ops is going old-school…he doesn’t do phone screens! He asks me, “How much time does a phone screen take?” I answer 15-30 minutes. He asks, “How much time would that take in real life?” I answer 30 minutes. Because your allotted time is relatively the same (for first-round sales interviews), why wouldn’t you want to meet them in person? He goes on to say, “What you get from an in-person is attention to detail. It saves a whole round of interviewing.”  Instead of having a phone screen, and then asking similar questions on the first round in-person, you get the same information in one. “It’s a win-win because you save time on your calendar, and they get a shot at presenting themselves in their best possible light.”

What else does this do? It creates a stronger networking bond. By meeting with someone in person, you can create mini advocates for your brand; even if you don’t end up hiring them. You’ll never know if you will in the future, or if they’ll be needing your product. An in-person handshake and 30 minute meeting goes a lot farther than a 30 minute blind phone call. And, If you’re still hesitant, follow Eileen and at least do video screens via skype.

Also, have them do a writing exercise. Daniel asks our candidates to write a sample email to a person at a very large company; a real person with a title they would be actually contacting. “It’s an example of their first day-to-day task that they’ll be doing.” Look for what kind of information they include like 10k reports, details, connections, etc.

Lastly, it’s the old adage: hire slow fire fast. You should spend far more time on the interview research process and have a pipeline of candidates. Daniel uses the 100 Rule from Greylock Partners (a VC firm that instructs hiring at Facebook and LinkedIn). The rule is: With 100 resumes or Linked profiles, from those you meet 15 in-person, and from those 15, you’ll find your candidate.”

*Shoutout to Andrew Riesenfeld, Daniel attributes a lot of his recruiting knowledge to him.

3 Musts.

For Daniel, there are three attributes in salespeople that are good indicators for success:

1. Attention to detail. If you’re a SDR sending a message to 50 salespeople, and you get a name wrong or have a grammatical error on the first line; there isn’t a conversation anymore. This is a big must-have.
2. Work ethic. Sales teams are in the office very early; usually the first. Closing deals essentially means running your own business. If you don’t grasp that concept, how are you going to be successful? Your territory is your own business, so make sure they have this!
3. Critical thinking. Have them walk you through contacting the VP of Sales at Adobe. Find out their play by play and their drive to succeed. How a salesperson thinks through selling is vital to the deals they’ll get.

Lastly, you have to just plain like ‘em.

Culture can mean more than their experience as a salesperson. Making sure a person meshes well and embodies your company’s values will directly impact the happiness of the team. In a lot of cases, sales skills can be taught, but values can not. Know what’s important to you in terms of culture.

That’s everything I’ve got. Good luck hiring a kick-ass salesperson!

What else would you like to know about Sales? Ask me here or tweet at me!

ToutApp’s New VP of Sales: C’mon Eileen, tell us everything!

Eileen Wiens defining career moment is happening as I type. Our new VP of Sales started last week, and she has already gotten our team off and running. I’m not joking, our sales reps are having ‘A-ha!’ moments on a daily basis. With a cheery demeanor and a lot of excitement, she tells me, “I think the biggest career move I’ll look back on is now. We’re in such a hot space, have high visibility, and I get the chance to sell to and meet the most influential people.” Right now, she says, “Is a new journey.”

I asked her to expand a little more on why she wanted to join ToutApp.

“C’mon Eileen (obviously a reference to the famous 80’s song), Why ToutApp, and why at this moment?

She gave me three main reasons:

  1. A great career opportunity
  2. The team
  3. The chance to be a part of something at the exciting and early stage.

“The Sales acceleration market is an emerging space, and we’re certainly an early player…and quickly becoming a leader. I’ve also been a customer for the last year (as the Director of Sales at Hoopla), and had such a great selling experience with ToutApp. It had major stickiness with my own sales team, so I knew it was powerful.”

What does she mean by ‘stickiness’? She was sold on our product when her sales team revolted when their trial was coming to an end. “They loved it and many said ‘I’ll just pay for it myself’ if it doesn’t happen. Very few sales reps would take money out of their own pocket. I knew right then; ToutApp was a powerful and game changing tool.”

Eileen’s background

In her exact words, “I got into sales when the earth’s crust cooled.

She’s spent the last 20 years in both inside and outside sales, and most recently, worked for Hoopla as the Director of Sales. Her first ‘sales’ role was working from the ground up– working in Lead Gen and making cold calls. She admits, “I waited till everyone went to lunch to make my first cold call.” Quickly getting over nerves (that lasted a millisecond), she moved up to Lead Gen Manager, and on to strategic alliances and Biz Dev during the .com days. She worked for a few startups, a Fortune 500 company, and emerged early into the SaaS space in 2004.

What drives her?

“For me it’s always been a combination of culture, product, and challenge.” A common theme in her background is building stuff. “For me, building a team, and building a company, is what ultimately drives me.”

What does she want to build? Something simply stated, but extremely powerful:

“A repeatable sales model that exponentially grows the revenue and the value of the company.”

How will you innovate and BUILD ToutApp?

She brings a tremendous amount of passion and ability to motivate salespeople.

She explains, “It’s Two-Fold: One, being able to design the sales strategy, and two, you have to be a good leader to craft a sales mission. She says being a leader means having the ability to get in the trenches with your team. “It’s important to get respect from your team by getting on the phone with them.” I asked what kind of leader she would describe herself as…“ People say that I’m a nurturing coach.”

Building a Sales Team: Her 3 C’s

  • Capacity: I’m always looking for a person’s aptitude and the ability to learn
  • Clock-speed: We’re a fast-growth company, and we want our sales people to reflect that.
  • Captivating: I want my salespeople to be captivating. They are the entire image of the company, and I want the customer experience with ToutApp salespeople to be memorable.

How Sales has changed, from her perspective.

In 20 years, she’s seen sales change tremendously.  “I think the biggest difference is that Sales is now an integral part of companies; companies run their entire business purely on inside salespeople.” This profession is now very much looked at as a respected role, with companies using inside sales as their go-to market sales model.”

Best Sales Win. Shoot!

As a leader, she gave the best answer, “It was actually a team effort for one of the largest social networking sites.” She went on to tell me an amazing story of building champions, hard work, with many hands involved. “It was a Global initiative with very specific engagement rules, and we were late to enter the competition.” Being a competitive bake-off, Eileen and another company were in head-to-head competition for the spot. “My Sales rep spent a significant amount of time of building relationships around the world. With a 90 day sales-cycle, and many stakeholders involved, our team had to continuously build champions, and we did it!” What does this teach us?

Sales is a collaborative effort.

The last important question.

And of-course, I had to circle back with TK, who tirelessly spent the last quarter meeting with over a dozen sales leaders to figure out who would be the right fit for our VP of Sales role. I asked him, “Why Eileen?”

“When it comes to hiring, I look for two crucial elements. I first look for a person that understands our mission and is willing to join up. We already had that in Eilleen because not only was she a loyal customer, she had already sent us a ton of referrals our way. The second thing I look for are people that are not just looking to be great at their jobs, but are looking deeply to advance the very craft they are in — and I saw that in Eileen the very first time I saw her speak at an AA-ISP panel.”

“We’re super excited and super lucky to have Eileen on-board as our VP of Sales. I consider myself to have one job, and that is to build a crack team of bad-asses. And with all the hires we’ve made this year, we’re well on our way to dominate in this space. I couldn’t be more excited.”