“This book is packed with Next Gen strategies and tactics I was able to take back to my team and implement right away. Hearing not only from the Outreach team, but also their customers, was a terrific way of learning more about the value of Sales Engagement. As someone who trains hundreds of reps per year at a growth-oriented company, I highly recommend this book to sales reps, managers, and leaders looking to build the most efficient and effective sales processes.”
—Jake Reni, Enterprise Sales Manager and Head
of Adobe Sales Academy at Adobe Inc.
“There are a lot of things I could say positively about the future of Sales Engagement. Prospecting into enterprise companies can be challenging, specifically reaching the decision-maker. With our Sales Engagement Platform underpinning our strategy, we have found that our connection rates are incredibly high—we talk to the decision-makers on average 12% of the time, with an overall connection rate of 22%. We are referred 5% of the time by those decision-makers when emailed. The Outreach team knows Sales Engagement better than anyone else in sales today.”
—Jennifer Brandenburg, Vice President of Worldwide
Inside Sales at GE Digital
“Ask anyone about what matters to me: they would agree that I care immensely about personalizing our business interactions for richer client engagement. Outreach is the only scalable solution I've found that allows companies of any size to initiate meaningful discussions without sacrificing the personal, more human touch. Beyond this, our teams are able to easily measure the effectiveness of their campaigns. Outreach allows us to hone in on best practices and winning sequences that improve opportunity creation, pipeline building and ultimately, sales bookings. So who better to write the book on Sales Engagement than them!? I consider this a must read for any sales leader, period.”
—Amy Slater, Vice President of Corporate
Sales at Palo Alto Networks
“A problematic divide has developed in the world of modern buying and selling. On one hand, 80% of customers say the buying experience a company provides is as important as its products and services. In fact, the importance of personalization in the buying process has now eclipsed solution fit when it comes to winning your customer's business. On the other hand, sellers are busier than ever, spending only 1/3 of their time actually selling with the remainder spent on research, meetings, and administrative tasks. Having led large sales teams where personalization at scale and sales rep efficiency were so critical for converting prospects into customers, Sales Engagement platforms like Outreach need to be part of every modern sales team's technology stack. This book will give you the blueprint for success.”
—David Priemer, Former VP of Sales at Salesforce and
Current Chief Sales Scientist at Cerebral Selling
“This book is a must-read for anyone who is trying to build a high-performance sales organization. Outreach has been walking the walk with their product for years and has finally put together the book detailing their most cutting edge strategies. There is no one better than Manny, Max, and Mark to write a book on Sales Engagement. Finally, we are able to allow our top reps to get 2X as much done per day, while our entry-level sales reps can learn from their team at lightning speed. Thank you, Outreach! Sales wouldn't be the same without you.”
—Tito Bohrt, CEO of AltiSales
“Today's sales leaders overwhelmingly name Sales Engagement as their top priority. They are focused on the quality and volume of sales reps' engagement with buyers as they look to drive higher conversion rates and larger average deal sizes. Sales Engagement is such a high priority that 90% of sales leaders plan to invest in technologies and methodologies to help their sellers engage effectively with prospects and customers. As the leader, Outreach is well positioned to write the definitive book on sales engagement.”
—Craig Rosenberg, Chief Analyst at TOPO Inc.
“On average, sales reps dedicate 15% of their time to manual activities like prospecting, which have a lower yield than other selling activities. Sales Engagement tools are emerging as a critical element for increasing prospecting efficiency and effectiveness.”
—Steve Silver, Senior Research Director at SiriusDecisions
“In modern sales, sellers need to rethink the way they interact and communicate with buyers and ensure that they have the modern sales tools needed to create an engaging relationship. Sales Engagement is one of the hottest new categories on G2 Crowd and is becoming a must-have in every sales technology stack.”
—Michael Fauscette, Chief Research Officer at G2 Crowd
Cover Design: Blake Brysha
Cover Image: © tai111/Adobe St
Copyright © 2019 by John Wiley & Sons, Inc. All rights reserved.
Published by John Wiley & Sons, Inc., Hoboken, New Jersey.
Published simultaneously in Canada.
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ISBN 9781119584346 (Hardcover)
ISBN 9781119584308 (ePDF)
ISBN 9781119584360 (ePub)
Sales is an art. Yet salespeople get a bad rap. This unfair discrepancy is the reason we started our company, Outreach.
I genuinely love salespeople. Hell, salespeople make the world go ’round.
Without salespeople, society as we know it would crumble. The word salesy is derogatory, yet the entire edifice of capitalism is built on the brunt of their hard work. Ideas, visions, and dreams have to be sold before they become real and start bringing in revenue. In fact, just about everything we enjoy or depend on (food, gadgets, films, sports, wine, health care, apps, music, art, travel, etc.) begins with a sale. Our economy quite literally depends on salespeople’s ability to endure an entire day of rejection and still get up the next morning and do it all over again.
And there’s plenty of rejection to go around. In sales, you are always on blast. Show me another profession where your performance is so cut and dried for everyone to see. You may think of professional sports or reality shows, but that’s exactly my point. Those professions receive fame and glory (or at least infamy), whereas sales gets a negative rap. In sales, you get the ruthlessness without the chance of a red carpet. You either make the number and get to play another round—or you don’t and are shown the door. It’s the only job where the score gets cleared every quarter and you’re only as good as your last deal.
When you think about it, sales should be the ultimate profession to draw inspiration from. After all, the best salespeople embody so many of the core values we hold dear in any other context: tenacity, determination, positivity, hope. Salespeople are required to go out on a limb. They must overcome their insecurities. They must roll with the punches, which come from all sides: their back-breaking schedules, their old-school leaders, and a harsh world that views them unkindly. These are all qualities people consider admirable in any other setting. Why is sales the cruel exception?
The plot thickens when we get into tools and technology. As it turns out, it’s not just the court of public opinion that keeps salespeople down. The entire deck is stacked against salespeople. Theirs is the mantle of “despite.” They sell despite pointless forecast calls that eat up their precious selling time. They sell despite arcane tools like Customer Relationship Managers (CRMs) that have them logging details instead of closing deals. They sell despite the noise, the distractions, and the pressure. We’ve all heard the stat that salespeople spend less than 36% of their time selling. Yet they’re expected to hit blockbuster goals in this bare minimum amount of time.
When you define the problem this way, it becomes a moral imperative to help salespeople.
Moral imperative is a term coined by the philosopher Immanuel Kant,1 and it often denotes the compelling need to fix something you cannot ethically tolerate. I love salespeople, and I just can’t sit idly by while they struggle using outdated solutions and selling resources—knowing that my team has already built and tested the technologies to make a material difference. I simply cannot ethically tolerate a world where the very people who help make it work for the rest of humanity continue to endure needless pain without the tools that will make their unenviable jobs easier.
Hell, sales is tough enough as it is.
I love salespeople because I’ve been a salesperson. I was the first Sales Development Rep (SDR) at Outreach when we were too broke to afford anyone with actual selling skills. Yet I managed to sell the company’s first 60 customers personally. And I did it by hand. It was hard, often thankless, exhausting work. During those lean days, it was the love stories that kept me going.
My sales experience taught me a lot of things. First, euphoria doesn’t come from closing deals. It’s from learning from excited customers that your product phenomenally works and that it drives transformation not only in their numbers and workflows but also in their mindsets and cultures.
I tried selling to many segments and discovered that tech startups tend to adopt faster than most. I sold a few licenses to a technographics firm called Datanyze and worked with Jason Vargas, Managing Director of Outbound Sales.
When Jason shared how Outreach empowered his team to achieve a more than 50% reply rate, I became the most ecstatic SDR on the planet. So I visited Jason’s team and discovered they were mostly ambitious people in their 20s trying to do their best at their first corporate job. They felt great about the experience and appreciated the energy modern Sales Engagement technology and best practices infused into their sales process.
Within just two quarters of implementing Outreach, Jason’s team doubled its revenue.
It was an awesome achievement for them. It was an aha moment for me. It was when the love I felt for salespeople became requited, instead of a one-way romance.
And it wasn’t a fluke. The same success and transformation that happened at Datanyze got replicated elsewhere—at global tech enterprises such as Cloudera and AppDynamics and in local businesses such as the Green Lizard Towing Company in North Carolina.
The emergence of Sales Engagement is changing the calculus for businesses. But more importantly, it is leveling the playing field for motivated salespeople who are trying their best to achieve the impossible for their team, company, career, and customers.
At the end of the day, the world needs salespeople to keep businesses profitable and the economy healthy. But given the lousy cards they are dealt with at the onset, salespeople also need every piece of assistance they can get.
So, yes, I do it for the love of sales. It is my dream and great honor to create a transformative solution that, if I’m very lucky, salespeople will love in return. This is the modern era of Sales Engagement, and it is the future of sales.
Manny Medina
CEO and Founder of Outreach
It was a warm fall September day in San Francisco when I got the phone call that would change everything. I was notified that I got the business development job at an early stage company called Udemy. I would be in charge of building the sales side of the marketplace.
It was a euphoric feeling—I got the job! Soon after, though, reality hit. In this role, I would be expected to build a sales process at a company that had extremely high growth goals and extremely low resources. This meant we had to be unbelievably efficient with our sales process.
A challenge like this is sometimes exactly what you need. You look in the mirror and say, “OK. If I had to streamline the entire sales process, with no wasted motions and effort, what would it look like?”
I realized I needed to think differently. I needed a foolproof way to get prospects’ attention. I needed to break through the noise. I needed a way to get in front of the buyer, wherever and however they consumed sales communications. I needed to be able to easily test everything from subject lines to calls to action to call scripts to voicemail intros. A way to scale my sales communications without sacrificing personalization. A way to easily follow up with potential buyers without having to write the email and physically press send each time. A way that leveraged multiple channels so we could meet the buyer where they wanted to meet, whether it was on LinkedIn, via email, over the phone, sending a gift, recording a personalized video, or meeting with them face-to-face at a conference. You guessed it: I needed to create a modern Sales Engagement strategy.
I spent the past five years building a media company called Sales Hacker, which continues to provide educational content to more than 100,000 subscribers on all things sales. Our content contributors are practitioners and leaders at the fastest-growing companies in the world. The industry has evolved at a rapid pace and in an incredible way, and I’ve been lucky to have both a bird’s-eye view and inside track. Sales Engagement is our most sought-after topic.
Through Outreach, I’ve spent the past six months talking to modern sellers and sales leaders, from some of the world’s hottest startups to Fortune 500 stalwarts, about Sales Engagement. These are our prospects and customers who are currently leading the industry or looking to take it to the next level. It is undeniable across the board. A dramatic change in sales is upon us.
This is a new era—a time where there are more options for the buyer than ever before. More information at their fingertips. More companies doing similar things. More salespeople to contact them about it.
Salespeople need to be ready. They need a whole new education and suite of technology. I’m here to tell you that it has arrived.
It’s time to be where the buyer is. It’s time to be testing and optimizing your outreach. It’s time to be relevant. It’s time to be personal. It’s time to embrace the modern era of Sales Engagement.
Companies doing this right are growing revenues at rates never seen before. Read on to learn the secrets to how they’re leveraging modern Sales Engagement.
Max Altschuler
VP of Marketing, Outreach and CEO, Sales Hacker
I was 16 years old, working my first job, standing in the middle of the entrance to the most horribly named shoe store in the world, The Athlete’s Foot. My blue, logoed polo shirt and khaki pants were complemented with some real fresh kicks (yes, my sneaker game is still strong). “So many bad shoes,” I thought as I looked at people’s feet in the mall traffic sauntering by. That’s when it hit me. A revelation. I could just keep standing there waiting for someone to walk in the store, or I could start engaging with people to get them to come into the store. My job wasn’t just to sell shoes; it was to help people understand they needed me to sell them shoes.
You might ask why someone would need me to sell them shoes. Simple answer: because an early sales mentor of mine (thank you, Michelle McGee) taught me how to find the perfect shoe for the person I was serving. I wasn’t selling shoes. I was selling a better morning run. Which meant I was selling a healthier heart and warding off the risk of obesity. Which meant I was selling more time to spend with kids and grandkids and the chance to watch them grow up. I wasn’t selling shoes. I was selling the sharp kicks that would complete the interview outfit. The shoes that would give that final boost of confidence as they walked in the door to that potential new job. I was a great salesperson that knew my product, could diagnose a problem, and cared about the person in front of me.
There was only one hitch: Nobody knew how much I could help them. I was the friend they didn’t know they had. I was a shoe guru hidden in a temple at the mountain’s summit helping only the people willing to climb to the top and visit me.
I needed to change my actions based on these new motivations. Standing in the store and waiting for them to come see me was no longer acceptable, so I decided to stand outside the store to engage people.
Two obvious things happened almost immediately. First, I was rejected more. As a skinny, pimple-faced teenage nerd in the marching band, I had thick skin, so this didn’t bother me. What did affect me, though, was the other thing that happened: My monthly bonus checks started getting much larger. Much, much larger.
I outsold everyone in my store. I outsold everyone in the seven- store franchise. In fewer than 20 hours per week, I outsold the full- time workers. Once I intentionally engaged with people—not to make a sale but to get them to understand how I could help them— I became a shoe-selling superhero.
As time went on and technology evolved, it became necessary to ask the next question: What is the digital equivalent of standing outside the store instead of inside it? How do you stand out in a person’s inbox when it’s so crowded that it makes the line at the Orange Julius in the late ‘90s look tiny?
That’s when I met Manny Medina through a mutual friend. Manny just happened to be trying to figure out if he could sell this new technology to solve this exact challenge. I saw the demo, and I was amazed by what I saw. It’s what I always wanted but didn’t know was possible. That’s when I learned that the digital equivalent I sought had a name: Sales Engagement.
I immediately made the move to buy Outreach’s Sales Engagement Platform for my team. A couple weeks later, as I was doing some trainings for my previous job in the Seattle area, I reached out to Manny to see if he wanted to meet up. He introduced me to Andrew Kinzer, Co-founder of Outreach, and we had coffee underneath the famous Lenin statue in Fremont. Manny and I talked shortly after and geeked out on sales and sales technology. Throughout our ongoing conversations, I became so inspired that I approached Manny about selling Outreach. His response? “We can’t afford you.” I offered to sell on a 100% commission compensation plan and still remember his exact words in response to that offer. Manny said, “We can afford that! Let’s go. I’ll send you leads tonight.”
Sure enough, I got the leads that night, quit my job two days later (with the full blessing of my wife and four kids), and started a five-month trek to selling $1 MM worth of Outreach. I was joined by four other people willing to follow me, one of whom flourished and is still one of our best sales reps, Theron Glenny.
Fast-forward three years, and I still have never regretted this decision. In fact, I love Sales Engagement and Outreach so much that we host 20 Outreachers at our Thanksgiving table every year—now that’s love.
My goal for this book is to share my inspiration with you and show you what’s so great about Sales Engagement so that you can begin your own transformative journey. I did, and I truly hope you will too.
Mark Kosoglow
Vice President of Sales at Outreach
Lastly, we didn’t want this book to be about us three, and it’s certainly not a book about a software company. It’s a book about a movement. An unfair advantage emerging in sales today that will definitely be here for the foreseeable future. That movement is Sales Engagement, and it’s being created by an entire community of forward-thinking sales leaders.
In order to do it justice, we made sure to provide varying perspectives from leaders of that community. These are our savviest Sales Engagement-focused thought leaders, customers, partners, practitioners, and executives from a vast array of companies and industries.
This book isn’t a silver bullet. Nothing in sales is. But it can be your guidebook, your idea sparker, your framework foundation, and much more.
We know it’s a game changer, and we hope you feel it too.
There is only one prerequisite for readers of this book: It’s for anyone interested in leveling up their game and anyone who is inspired by the idea of doing more than they ever thought possible.
For nine out of 10 people, audacious goals are the stuff of overwhelm. This book is for the odd one out—the one in 10 who goes against the flow. The rare soul. The moon landers. The four-minute milers. The person who is inspired—not intimidated—by the idea of breaking records. If you’d rather take action and make moves, then this book is for you. If you find yourself questioning whether long-held limits are absolute or just arbitrary, come along as we take you on a journey on a rocket ship. These pages will ignite your imagination on how to test those very limits and perhaps raise the standards of human achievement in your field.
This book is not meant for people already satisfied with the comforts and familiarity of the way things are. Instead, this book unmasks the most poignant challenges of tomorrow and explores the rich opportunities for individuals and teams who dare to look at mastering the future. This book is for anyone who wants to play full out, wherever they are. It is for the young Sales Development Rep, prospector, or cold caller/e-mailer who dreams of hitting their number for the first time.
It’s for the Account Executive still struggling to hit their number consistently. It’s for the Senior Account Executive who’s mastered the basics and now wants to break a personal record. It’s for the sales leader who dreams of creating a world-class org that will be revered as a shining industry example—the stuff of keynote speeches and case studies. It is for the Sales Operations Specialist who, behind the scenes, is quietly and methodically architecting an epic workflow that will quadruple productivity but who will probably never get a thank you, let alone get invited to President’s Club. It is for the Customer Success Manager who inherits the efforts of all the above and puts on a smile and fulfills the hell out of those grand sales promises, even if it means answering the phone on a holiday or advising on yet another strategy after an endless day of work.
Only people who actively want to make a difference and transcend the inertia of the daily grind can hope to appreciate and apply the nuggets of tactical wisdom that line the chapters of this book. Only professionals who ask the right questions and seek new, better, and smarter solutions to their business problems can hope to glean anything of value from this pioneering work.
This book is for anyone fascinated by the idea of greatness and what it takes to truly achieve it.
If you share this passion or fit this description, then this book is definitely for you. Within its pages are insights, tactical tips, and practical solutions that will address your most urgent pain points and finally move the needle on your personal or team performance.
Although this book focuses on results and sales performance, anyone who wants to shake things up and change things for the better can benefit from reading it:
This book targets people who don’t merely want to win; they want to redefine what it means to win. Sure, they want to make their number—but they also want to make history. They want to leave a legacy. When people ask, “Who’s the best _____ (insert sales function here) you know?” These knowledgeable responders will always say your name.
This book is for the ones who want to play big and win big and bask in the glory when they do. This book is for you.