I will try and compress all that I know about sales and passing the pen test into the smallest amount of space. It is the wisdom I had to snatch like Robin Hood from countless sources over my sales lifetime.
This it not a lossless compression. Some sales slivers of know how and experience have been neglected, some deliberately not included and others just lost. 
This is for the soldiersThat see the sun at midnightYou dig, let me slow downIt’s so incredible – Free Mason by Rick Ross
I am going to list everything without any priority: Bullet 2 will follow bullet 1 and bullet a. will come before b.
But it doesn’t have to. What is important is that you read them each and then add them all together.
1. The company
(you are judged by the company you keep)
a. If they don’t care about their clients, they don’t care about the instruments that acquired them.
b. If the CEO is an an ego driven jerk the company is a big jerk farm. If the CEO is personable, listens respectfully, is responsive and understands their obligations to the employees and clients, then that too will cascade down. Choose your CEO well.
c. When companies want to improve shareholder return one of the first places they look is in reducing sales payouts.
d. Brute sales force is when the company overhires sales reps as a strategy to divide up the market into the smallest particles. When a company uses this arguable strategy they are divvying up the profit (or anticipated profit and/or revenue) into smaller cuts. Commissions are distribution of profits. If the company is not profitable then the payout is meager.
e. Brute sales force makes the sales rep an anonymous foot patrol and it’s hard to distinguish yourself.
f. Companies that use a brute sales force strategy have a higher than normal attrition. That is often the rumble before an earthquake.
g. Brute sales force is great for the marginal sales rep, they can skate by and nobody cares. They soak up salary, commissions are icing on their cake.
2. The Sale
(there are two types of sales)
a. Transactional. Sales reps don’t make money, period. The company allocates their resources to creating a system that reduces the sales person to a pleasant cash register.
b. The complex sale. In this model you can (hopefully) make a lot of money. Your role can not be turned into a nifty website. The best sales person builds a conveyor belt to make their sale transactional ‘like’ so they can handle more volume without compromising quality.
c. To understand and appreciate the product you have to ask the client why they signed with the company. This is never a conversation about price, its about value.
d. When prospects are selecting a vendor they are jumping out of an airplane, they are not sure if the parachute will open. They will go with the firm and the salesperson who gives them the confidence they are going to land safely.
3. You
a. You are selling the biggest part of your life. Your employer is always checking the current exchange rate, you should be also. Some part of improving the exchange is increasing your sales, but some other parts are the fairness of the compensation and the rewards, company culture and their eagerness to retain clients and their top talent.
b. When you are successful people have their envious assumptions and you shouldn’t encourage it. People will try and shoot you down and with patience they will win, you only have to slip up once, and you will. So be overly nice. Reduces the probability of ‘internal’ failure.
c. Invest. Compensation in sales can be excellent. The dull side of that blade is that you’re paid today with less visibility into your future earnings. Live frugally, invest abundantly. Elder you will be thankful to the younger.
d. The difference between minimum and excellence is all discretionary effort and it happens because you want the recognition from others and from yourself of a job well done. That is not only a financial gain, its an emotional one.
e. Prospects have a lot of anxiety in making their decision. When they have a question that are likely contacting you and the alternative sales reps, whoever answers first and best has an insurmountable advantage.
f. The company sells the product, you sell the ease of on-boarding, being somewhat the client advocate, answering their questions and holding the chains tightly to make it all work. Only say things like ‘ from my experience’ ‘this is the experience of our clients’ ‘our clients prefer’. You have to take yourself out of the product equation. Some big part of this is ego. To be successful you have to set that free, if your ego loves you it will come back when you cash the checks.
g. There is at best only a 50/50 chance that the prospect will personally like you and there is even a lesser chance that they will trust you. So by emphasizing the company brand and emphasizing your ability to get it implemented in their company you are improving the probability of the close.
h. In sales, you are not just holding the prospects hand, you are dragging them across the street like a stubborn basset hound.
i. Never try and make the prospect a friend until the deal closes, you are only making it easier for the prospect to stall, to be vague and excusing their unresponsiveness. Friends are forgiving. Business partners aren’t.
j. Don’t be a nice person. Its okay if they don’t like you, as long as they respect the quality of your job and performance. Then after they become a client you can lighten the mood by simply calling them and saying thank you. Then drop the bomb again and ask for referrals.
k. always ask for referrals. Plant that seed so that when they encounter another prospect they will say to call you.
l. Make everything a template. Prior to the first meeting or call send an email setting the agenda and letting them know in advance what info they will need. Prior to delivering the proposal send an email with an agenda listing the next steps to becoming a client and on boarding. It should all be a template and you just need to swap in names and add or subtract the particulars. 
m. If your pipeline sucks you will fail. If your pipeline is full with quality and quantity, predictability improves and the industry statistical norms will at least be achieved. Also, it makes it a lot easier to end all price negotiations. Clients like hearing no because it is precise. Decision makers always need the most precise information, if they feel they can negotiate then it is an unknown and the unknown is troubling.
n. Never bullshit. If you don’t know tell them you will come back with the answer. Include it in the agenda for the next meeting and the close and post sale. If it is news that may jeopardize the deal, say it and then find workarounds if they are some, if there are not, they are not. Period. But tell them well in advance.
o. Always send an email in advance of the meeting that includes an agenda and the information they will need to provide. In advance of delivering the proposal send an email saying the steps to becoming a client in their proper sequence and setting expectations.
p. If a prospect is not suitable, tell them. Be nice and move on.
q. Don’t let a prospect over complicate the sale. They are often looking to find a lever that lets them say ‘no’. Don’t give it to them. Fight it like thenew prisoner declining a stick of gum.
r, Never permit endless pointless questions, it will force you to overcomplicated the process and you will never recover. You have to move them back onto your sales conveyor belt.
Competition
Never explicitly criticize the competition. To win against them you have to break apart their mythology. Use pricing, technology, service or the judgment of your prospects peers.
Sales Gurus and sales role play
a. Sales books are stuffed with ‘meme like’ pickup lines. They are made for the low sales producer who will read all the books and then quote them in office sales meetings. Then the books will sit on their desk so that the boss will always see it.
b. Sales conference keynoters are there so that the failed sales reps can cheer the loudest and say how transformational the speech was and how as soon as they get back to the office they are going to use those magical memes.
c. Networking in sales conferences is awesome. Spending time with your peers and management (especially for a company with human capital distributed around the country) is equally awesome.
d. Sales conferences usally have an awesome pool. 
e. Sales role playing is awesome for everybody. Discuss complex sales, the market landscape and role play endlessly.
d. Subscriptions to sales gurus. The failed sales reps always want to get a subscription to the sales guru newsletter. They go into their bosses office and plead for the perk, its more suspect proof of their imbibing of the company/sales kool-aid.
e. Sales gurus sell books, subscriptions and conference keynoting.
Misc:
a. VC’s don’t understand sales dynamics. The VC firms can have nice graphs but they only know theory and what has worked in history, rather than the positional play of each company, the complexity of its people, volatility of competition, geographic and industry factors (see Andreeson/Horowitz and Zenefits)
b. Company management techies always think they have designed such a superior product that will sell itself. They live in algebra, sales lives in the intangible.
I cant stand when I hear people say ‘sell me this pen’.
I have never had to endure it.
Its something people who belittle salespeople say to humiliate them in their elitist way.
I suppose if a gun is pointed to my head (I would much rather give them my wallet)
Elitist: “Sell me this pen”
Me: “would like to buy a pen?”
If they answer no you can thankfully stop the humiliation. If they say yes, the humiliation must continue
Me: “What type of pen they would like to buy?””what are its qualities?”What are the features you would like””How much are you looking to spend?””When do you plan on buying this pen?”.
If we have reached some type of a deal, then I slap the pen out of their hand and sell it to them for 20% more then they had expected to pay in our role play. – me
(Legal disclaimer. The author does not condone mugging or pen theft. Please only play ‘sell me this pen’ at your own peril)