“If you have to throw your VP Sales at every big deal, you don’t have a scalable sales process” — Aaron Ross, author of Predictable Revenue.

“Don’t give out proposals & quotes like 1 of those people standing on the street handing out flyers. Prospects must ‘earn the right’ to a proposal.” — Same guy.

I’m occasionally asked questions like : “What’s your favorite sales book?” and “How can I learn how to cold call?” from friends who are just starting a business, founders looking to hire their first sales rep, or peers who transitioned into a role that does sales/account management who previously have no experience. ‘Predictable Revenue’ is one of my favorite sales books and I recommend it every time. I think anyone should know what sales is all about and how to at least think about some of the more ‘basic skills’. There’s also too much bad stigma associated with it and sales people are often considered to be ‘car salesman’ by engineers and developers. It’s definitely possible and it definitely happens, but that’s minor league sales. The best sales people fit right in with your team.

It’s been said lately that everyone should learn to code and I also think that everyone should learn to sell and understand the basic principles of sales: cold calling, leaving voicemails, knowing your ideal customer, how to pitch, etc.

I’ve been doing this sales thing for about 7 years now (Nordstrom shoe sales, Instructure, Dyn, Parse, Facebook) and while I’m still learning, I’m always excited to find new literature, concepts, or best practices that help me in my daily quest that I can use personally and also share with others. About a year ago I stumbled across a post on Quora about the best sales books, and one of the authors Aaron Ross chimed in about a few things he’d learned scaling out the Salesforce sales team and building a $100 million dollar business. Everything he said resonated with me. I immediately bought the book on Amazon, anxiously closed out my business that day, and spent the next 3-4 hours reading on my Kindle on the floor of my apartment on a cold, rainy day in Oakland. I’m certain that my wife thinks it’s a bit odd that I love sales books. But I do, and if you love sales or want to understand it better, you’ll love this book.

Let’s get started.

1. “You must determine a clear Ideal Customer Profile”

It sounds so outlandishly simple but do you know how to answer the question of ‘Who is your ideal customer?’ How much time have you spent identifying who the exact, perfect customer is that you want to bring in the door? You probably have a market in mind, or maybe some specific companies, but what are the characteristics of the client that you want. This isn’t just “I want the customers that can pay me the most”. It’s much much more than that. The types of customers that may be able to pay you the most are also often the types of customers who are going to make you work the hardest during the negotiation / legal / procurement processes. They also may be the types of customers who are going to hold you the most accountable, be inflexible, and take the most time of your Operations and Support teams. This might be reasonable/OK if you are a team of 100 or 500 (but even still, not good), but when you’re 1, 10, or 20, you want to work with customers that love your product, are willing to consistently spend money every month with you, are flexible when you occasionally have a hiccup with your service, and who can accept your Terms of Service as they are on your website.

2. ‘Cold Calling 2.0.’

When someone talks about ‘cold calling’, they usually talk about it with the highest levels of disdain. This shouldn’t be a surprise to anyone that does sales. Cold calling is hard. You are faced with rejection from the moment you start. You are reaching out to someone you don’t know, asking them if you can spend a few minutes with them, and trying to see if they are open to trying your service/product. Of course you’re going to get rejected.

Aaron talks about ‘Cold Calling 2.0' which I think is fantastically simple. I’ll outline this in very specific terms, because I think this can be incredibly effective in improving the number of warm leads, pitches, and deals you close.

The first thing that you need to do is define your ideal customer profile, as mentioned above. Once you have an idea of who this is, you can start to define the types of companies that might fit into this mold. Let’s say for example you knew that HP’s Cloud Services Division would be an excellent customer for your product (in this case, mine is Parse). I would then find out the highest level VP / Director in that Division, or even better, I would find the CEO / COO / CTO. In this case, Meg Whitman. I would then send that person an incredibly short, simple email asking them who the right person is to talk about ‘app developer services’. It could, quite literally, read like this :

Subject : Could you point me in the right direction?

(firstname),

I’m sorry to trouble you. Would you be so kind as to tell me who is responsible for [insert your biggest pain point here that resonates with your ideal customer; OR insert function like “sales” or “recruiting”] and how I might get in touch with them?

Thank you

Your name/Your signature here

That’s it. It sounds idiotic and overly simple, definitely, but dang this thing can quickly get you to the right person and get you a response. But let’s say you don’t believe me. Let‘s talk about the psychology of a cold email. If a cold email is sent to you from some random guy you’ve never met before, you’re very likely to ignore it, archive it, delete it. You have the choice to do this. When an email hits your inbox from your CEO, your Director, or your manager, you’re going to at least read the email and you’ll most likely respond immediately. You almost don’t have a choice here. Most sales people spend a lot of their time trying to find the ‘right person’. The CEO/email referrer has now helped identify that person, and whether you like it or not, the sales person now knows. The sales person can be reasonable and let you respond, he can cold call you by phone until the end of time, or he can even start following you on Twitter and look for ways of engaging with you more personally to increase your chances of talking with him.

Ultimately, the biggest battle has been won. The sales person knows who the right person is. I can tell you with 100% surety that this system works. Anecdotally, I emailed the CEO of HP and within 10 minutes one of the Directors of their Cloud Services team called me to schedule a meeting. They called me!

3. Automating Cold Calling 2.0.

The last thing I want to cover in this post is automating sales outreach. Automating those outgoing emails from ‘Cold Calling 2.0'.

Most sales reps will come in at the beginning of the day and just start typing away, answering emails, not considering what the most high priority things for the day would be. What they should be thinking about, and I’m over simplifying, is : Moving deals towards close AND finding new business.

Everyday, every single day, sales reps need to find new business. ‘Always Be Finding’. Without it, you fail in X months.

So, taking the Cold Calling 2.0 concept a bit further — let’s ‘automate’ this. Let’s say you found 20 of your most ideal prospective companies and you found 40 contacts (2 per division or 2 per company, whatever). Use any kind of email templating and scheduling program, like Salesforce/Marketo/MS Office, and schedule 40 emails to be sent, with the same template email, to each of those contacts, at 6:30 pm at the end of your day. This does a few things:

• The person receiving your email at 6:30pm is either leaving work, on the train, or just got home. Your email is showing up right as everyone else is quitting and his inbox has slowed to a dribble. He actually has 30 seconds to think and respond to your email. “I’m not the right person, you should talk to Bob (cc’d)”. Bam, you’ve got the right guy.
• You’ve left work at 6pm, are on the way home, and you know that the next morning, you’ll very likely have 2-5 responses letting you know who the right person is or isn’t, and whether they are open to scheduling a discussion. It’s a good evening and you’ll follow up tomorrow. You’ll do this everyday and you’ll be successful. You can track this, A/B test your emails, and gauge improvement.

I’ll end here, otherwise I’ll probably end up covering the entire book — and while Aaron Ross certainly doesn’t need your $10, his words are much clearer and concise than mine. Buy the book. Thanks for reading.