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Great Sales People are Built not Born

Over the last 4 years I’ve been part of promoting 24+ folks from the sales (business) development rep (SDR/BDR) role. Most of these SDRs have gone from college to their first closing role as an AE at an enterprise SaaS company within 18-24 months.

It’s awesome to watch young, talented, and hungry junior sales people have the chance to accelerate their careers. It’s also given me perspective on what it takes to succeed in B2B enterprise SaaS sales. And what it takes is a lot.

The failure rate of a first time AE is substantial. It’s not just not easy to move from setting appointments to closing five or six figure deals. So congratulations on moving up. Time to get serious.

What’s below?

This post identifies gaps in the training of most junior sales people and points those junior sales reps to valuable resources they can learn from.

I do this by identifying six parts of sales that are often overlooked in the formal professional development you are likely to get. Within each of these areas I give you a list of resources that you can use teach yourself.

The six areas of knowledge I’m going to cover are:

  • Gap 1: Understanding the role of sales within the whole company (so you don’t look stupid)
  • Gap 2: Knowing the things your boss cares about
  • Gap 3: The Landscape of Sales Methodologies
  • Gap 4: There’s no Sale Without a Lead (Sales and Demand Gen)
  • Gap 5: Psychology, Stories, and the Art of the Sale
  • Gap 6: Internalizing that it’s actually all on you

While both my list and the list of resources are necessarily incomplete, it’s a curated set of reference material you can’t go wrong with, and I’m confident it will give you a leg up.

Gap 1: Understanding how sales fits within the whole company (so you don’t look stupid)

As an SDR you come into the working world, usually straight from school or via an unrelated career, and get thrown into the deep end without much fanfare.

Within a couple of weeks you’ve learned a script, gotten a basic grasp of your company’s buyer and all of a sudden you’re on the phone, emailing dozens, perhaps hundreds of prospects. You learn that sales is tough. You start dreaming about your quota number. You also build a bond with the other sales reps grinding next to you. Camaraderie is inevitably built one rejection at a time.

Gradually you get more sophisticated. You learn a bit about what works and you get more comfortable in understanding what you need to do (inputs) in order to hit to meet your number. With the basics down, great reps will start spending more and more of their time on (1) the ins-and-outs of their product and (2) their customer’s needs, pain points, corporate structures etc.

But rarely in this process does anyone take a step back and talk to you about how sales fits into and interacts with the rest of the company.

This is a problem and here’s why.

The truth is that sales occupies a unique and often tension filled niche within a company.

At least some people at your company think that: (1) sales is easy or even unnecessary, (2) you’re overpaid, (3) your team is loud and obnoxious, (4) you sell deals that are bad for the company, (5) your team is full of bros and has a sh*tty culture that’s nothing like the rest of the company.

These are stereotypes. And right or wrong, true or not, you are part of the sales team and you must be aware of these biases in order to avoid coming across as ignorant, or worse, unintentionally insulting.

Once you understand the role of sales and understand how it fits within your company’s specific stage of growth you can deliberately build relationships with other teams that shatter their preconceived notions. Trust me, this understanding plus a basic grasp of how a company scales will put you miles ahead reputation-wise relative to other sales reps at your company.

How do you gain this perspective?

In my opinion the best place to learn these lessons comes from the resources that VCs and certain “been-there-done-that” sales leaders have put together for teaching technical start-up founders about sales.

Resources on Sales and Scaling a Company:

  • Product Market Fit – You can’t be in tech sales without knowing the concept of product-market fit
  • 16 mini-lesson guide on Sales for technical founders – A series of mini video lectures from Andreesen Horowitz, one of the premier VC firms in the world
  • Why SaaS Products Don’t Sell Themselves – A clean, concise blog post explaining the role of sales AND the sales process all in one. By Mark Cranney, a sales guru you should know. This is one of the best posts on sales I’ve ever seen
  • Scaling Sales & Common Sales Traps – The first 20 minutes of this lesson in Y Combinator’s famous “how to start a startup” class at Stanford is crucial knowledge about how companies get to their first $1M+ in sales. It’ll also give you a strong foundation in the sales funnel
  • Zero to One – Peter Thiel’s book on building a successful company. Chapters 3-5 in particular will give you a lot of context on understanding markets. This thinking on how to understand your competitive landscape will give you a lot of insight into what strategies may or may not work in your space against your competitors
  • Building and Operating a High Growth Company –A 40 minute video by Keith Rabois (Paypal, Square, LinkedIn) which serves as a crash course for the different stages of a rapid growth tech company
  • The Hard Thing About Hard Things – Ben Horowitz’s version of running a successful company, with a heavy emphasis on selling in competitive environments. This is wildly entertaining if less relevant than the rest. The chapter “Take care of the people, the products, and the profits: in that order” is probably the most relevant

Gap 2: Understanding what Sales Leadership cares about

Remember that boss of yours? A sneak peek at your boss(es) and what they and what they care about is just common sense. This includes: (1) what they look for, (2) what they’re judged on, (3) what they do day-to-day, and (4) how they’re paid.

This list tackles some of the above:

  • Running a Sales Team – From the perspective of hiring the right VP of Sales. The full video from Jason Lemkin is also 100% worth the 40 minutes it takes to watch
  • Building a Sales Plan and Understanding Sales Stages – Good one stop shop blog post. A 101 of why sales stages exist will help you understand your managers, sales ops, and forecasting all at once
  • Mark Cranney specifically on forecasting – Another short, no-nonsense post that is solid all the way
  • The Psychology of Setting Prices – Not sure it belongs in this section, but here you go. Pricing is make or break on so many dimensions, and this summary post describes it’s importance well (+ links to many more resources)
  • The Lifetime value of a customer – LTV is another basic metric you need to understand as it defines your overall business. This article remains high level and doesn’t dive into the financial side of things but is a good primer and plugs you into the relationship between customer success and sales via retention rates

Gap 3: There’s a lot of ways to sell (Sales Methodologies)

Chances are your company has a sales methodology, either implicitly or explicitly. This might be one of the well-known rubrics out there like Sandler or the Challenger Sale, it might be a mash-up of many, or it’s home grown. Either way, you’ll pick up some strategies/techniques from all of the various models, and you’ll get a better sense of your field that is especially useful when you’re looking for a new job somewhere down the road at the same time.

  • SPIN Selling – Neil Rackham
  • The Challenger Sale: Taking Control of the Customer Conversation – Matthew Dixon
  • A more tactical post on selling enterprises – By one of General Assembly’s more senior sales leaders
  • A checklist of how to get your mind right in sales
  • Getting to Yes: Negotiating Agreement Without Giving In – A really good book to understand the basics and the subtleties of negotiation
  • Getting More: How You can Negotiate to Succeed in Work and Life– Stuart Diamond offers a good basic book on thinking long-term and putting yourself in the other person’s shoes
  • Never Split the Difference: Negotiating As If You’re Life Depended On It – Chris Lerner is a former FBI hostage negotiator. This is a good, perhaps not truly great, read, but it is entertaining
  • Hubspot’s Quick and Dirty Post on 10 Sales Methodologies – BANT, MEDDIC, Sandler etc. This is a great overview post.

Gap 4: There’s no Sale Without a Lead (or the Role of Demand Gen and Marketing)

There’s no sales without a prospect, and prospects come from a strong lead generation effort that involves sales and marketing.

But most sales people don’t spend enough time understanding either (a) demand gen, or (b) marketing as a discipline.

After all when was the last time you thought about a commercial on TV as part of a sales process? The reality is that sales is about solving a problem someone has, and part of that means making them aware of that problem in the first place.

I truly believe that in broadening your understanding of selling, and truthfully, of social psychology you’ll innately become a more aware sales rep.

  • Hacking and Bootstrapping to First Sales – Sales 101 and full range of tactics through the personal story of a startup
  • Invisible Selling Machine – Ryan Deiss
  • The Sales Acceleration Formula: Using Data, Technology, and Inbound Selling to Go From $0 to $100 Million – Mark Roberge talks through his lessons learned doing exactly what the title says at Hubspot
  • Growth IQ – By Tiffani Bova
  • Predictable Revenue – Aaron Ross, the bible establishing the context and the birth of the SDR role. Worth at least reading a summary for context on a modern SaaS organization

Gap 5: Sales is a Discipline of many other Disciplines (or why you’re framework of sales is too narrow)

Some of the below are sort of ‘memoirs’ of successful people in sales and marketing. Sometimes these types of books are great and entertaining. More often, they’re awful. Here are some that I think are great:

  • My Life in Advertising – Claude Hopkins. One of the early successful marketers in America. This is a wildly entertaining and educational book that takes you into another era
  • What They Don’t Teach You at Harvard Business School – Mark McCormack, the founder of IMG about his life. A lot of wisdom here related to doing deals and especially field sales
  • Influence: The Psychology of Persuasion – Robert Cialdini
  • How I raised myself from Failure to Success in Selling – Frank Bettger
  • How to Win Friends and Influence People – Dale Carnegie. An all-time classic that you’ll hear cited over and over. Might as well read it now
  • The Art of the Sale – Philip Delves Broughton

Gap 6: Not Taking Responsibility for Your Own Learning

No matter how innately talented you think you are, succeeding in modern enterprise sales is a learned process. It takes time and effort. That is after all the whole point of this post.

So what should you expect as you take your next step?

When you first move to an AE role you should expect a structured learning program covering sales fundamentals and the specifics of your product and sale. Note: if you’re at a company where the sales is team is >25 people and you don’t have this that is a HUGE red flag.

But even if you get good training, you can’t rely only on company-provided training to give you everything you need to succeed.

A company sales program is designed to teach you to sell one product within the specific context of your company. That means the training is specialized and deep in some areas, but likely to ignore or spend comparatively little time in other, sometimes broader areas of selling. Besides, think about how much knowledge lives outside of your organization vs. within its walls. You owe it to yourself to figure out what you don’t know you don’t know, because truth #1 in sales is, you own your own results.

General Resources on Learning

Note these are the least directly “sales”, feel free to skip ahead)

  • Levels of the Game – John McPhee
  • The Art of Learning: An Inner Journey to Optimal Performance – Anyone who is both a Chessmaster and world martial art champion (in Tai Chi Chuan) is worth listening to. Josh Waitzkin is that person
  • Tools of Titans – Tim Ferris. A collection of interviews of successful people from across disciplines. any of the interviews pertain to your success in sales
  • The Talent Code – Daniel Coyle
  • The Power of Habit – Charles Duhigg
  • Mastery – Robert Greene
  • The Puzzle of Motivation – A classic TED Talk on what motivates people. Hint it’s Mastery, Autonomy, and Learning

In summary

In summary, it’s on you.

You are entering a demanding discipline with high risk and high potential for reward. The “gaps” listed above are meant to help give you another perspective on your journey. are far from comprehensive. I mean, we didn’t even talk about the customer!

Just remember, you are not owed anything and there is always more to learn. Embrace learning more than most about your craft and it will pay off. Oh, and as you come across amazing resources, I’d love to hear about them.

Sales is a craft, and good craftsman are rare. Hopefully the list of resources that follows will help you get there.


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Last modified: February 10, 2019