Updated: Mar 18, 2019
If you are a B2B/B2B2C founder or work for a B2B startup, what do you think when you hear the word “sales”? Honestly. Do you have variations of “build it and they will come” beliefs? Are you imagining semi-aggressive guys trying to push others into buying what they don’t need? Or do you imagine people with incredible persuasion skills and “charisma”, those who are able to sell “ice to Eskimos”?
All of the above is not what modern sales is about. If these images pop up, you need to upgrade your knowledge on sales and the strategic role it plays in your business. Of course, you will learn from trial and error, you will learn from own failures and successes. But what I am offering here is to try to prevent some of the common mistakes by learning from the experts.
Over the past couple of years, I worked with B2B companies exclusively. I’ve seen hundreds of organizations both successful and struggling, and I was looking for patterns. I've seen that companies across industries, stages and continents make the same mistakes over and over again.
In this post, I would like to share the books and resources that will help you understand sales from both strategic and practical angles. Unfortunately, there is no single book that has all the answers. Here I've collected the best books and resources from the VCs, software companies, authors, sales practitioners, and consultants.
Resources from reputable VCs
All things sales, 16 mini-lessons for startup founders, a MOC course by Peter Levine from A16z
This is a series of videos with high level but high quality content. Peter talks about the basics of Go-to-Market, Building Sales Org, and Managing Sales org in a structured and no BS way. Based on my experience working on 30+ B2B engagements across industries and company life cycles, I agree with 95% of what he says and generally “preach” the same. If you are new to thinking about building your sales organization or just don’t know much about the area, this is the best investment of your time. Note that devil is in the details, though. Implementation of all this great advice is where the rubber hits the road.
Resources from Matrix partners
Another high-quality content from another top tier VC with many B2B investments. David Skok, a general partner at Matrix Partners, is generally considered to be a SaaS economics expert and has produced very useful materials. I find these ones to be the most useful to founders:
Matrix Growth Academy – Zero to 100 Videos – high-quality course on B2B sales that covers all major topics on the way to “Repeatable, Scalable & Profitable Growth”
SaaS Metrics 2.0 – A Guide to Measuring and Improving what Matters is a detailed blog about SaaS metrics. It talks about bookings, new MRR, expansion MRR, revenue and a number of other metrics. No SaaS company can avoid measuring it and getting into these quant details. There is also an example of dashboard that companies can directly implement. Of course, the implementation challenge is to translate your data and your situation into these templates and make sure that these are measured, reported, and acted upon at all levels in the company.
Resources from sales and marketing automation companies
Now every SaaS company that sells into sales and marketing departments is doing content marketing. Not all of it is informative, useful, or unbiased. There are some examples that I consider good and I’ve seen the results work in practice:
The definitive Guide to Lead Generation, by Marketo
Insights on incentive compensation and sales planning (think territory design) by Xactly; these are more advanced topics for larger companies (from an older-school company), but familiarizing yourself with the possibilities is useful
Now, let’s talk about books. First of all, I have to say that high-quality books on sales are extremely rare. More rare than in other areas, like behavioral science. That’s why I hand picked a differentiated portfolio of the best assets. None of the books is enough to bring you all the returns on its own, but together they can help you build a solid base.
Strategic books on sales and how sales fits in the bigger scheme of things (B2B)
Influence: The Psychology of Persuasion by Robert B. Cialdini
(Note: for your convenience, all book images are links to Amazon)
This is the classic book on influence, yet it’s still very relevant. It does talk a lot about old school sales people, but in a way that you learn useful insights. The author talks about the 6 fundamental influence principles: reciprocity, commitment and consistency, social proof, authority, liking, scarcity. More recently, the same author wrote Pre-sustion (thus adding the 7th principle), which sort of reflects the changing times. You have to pre-suade people before you have a right to influence them. I would still recommend starting with the original book.
Crossing the Chasm: Marketing and Selling High-Tech Products to Mainstream Customers by Geoffey Moore
Another must-read classic. We all know the terms “early adopters”, "late majority", etc, but that superficial knowledge may deceive you into thinking that your products go through the adoption cycle automatically. In fact, there is a huge "chasm" between selling to early adopters (technical enthusiasts and visionaries) and selling to mainstream customers. And the later customers do not care much about your success with the former. The book talks about how to cross this the charm. It is useful for technical founders and executives who believe in “built it and they will come” (no, unless you count on what Naval Ravikant calls "blind luck"), self-adoption, and that “inbound is the new outbound” (not in B2B beyond a certain price point and share-of-wallet). It is also a mist read for founders who have found success in the early markets and need to learn to grow with the company.
Hard Things about Hard Things by Ben Horowitz
A great and honest (although still extremely opinionated) book about how to be a CEO by Ben Horowitz (in Andreesen Horowitz, if I have to explain). This is not a book about sales, but he does talk a bit about sales from the CEO perspective. In his own words sales is one of the two most important functions in a B2B business. The reason I included it hear is because his way of thinking is very relevant for B2B startup founders, CROs and sales executives. Step back and get a perspective on things that matter the most for your business, your development, and sanity.
Books from sales practitioners
The main strength of books written by practitioners is obviously the fact that the authors have seen things work in practice. The main weakness of these books is that the authors extrapolate individual (sometimes idiosyncratic) experiences that are specific to few companies, certain moments in time, etc. The authors may have bias “if it worked for me at the time, it would work for you”. That's why I strongly recommend supplementing these books with other sources on the list.
The Sales Acceleration Formula: Using Data, Technology, and Inbound Selling to go from $0 to $100 Million by Mark Roberge
The best practitioner book I know is from Mark Roberge, the former SVP of Worldwide Sales and Services at Hubspot. Mark preaches sales as a science. He talks about inbound sales, hiring people, building sales processes around customer journeys, a bit about sales compensation and other fundamentals. Perhaps the part that is closest to my heart is about hiring people. What he is suggesting is basically a structured interview process that has been proven to be a much better predictor of performance than unstructured (gut-feel conversation) interviews. In my view, Mark overemphasizes inbound sales, which is understandable given the Hubspot’s business. Your take aways should be about the way of thinking and approaching sales rather than repetition of his exact decisions.
Predictable Revenue: Turn Your Business Into a Sales Machine with the $100 Million Best Practices of Salesforce.com by Aaron Ross and Marylou Tyler
As I mentioned Mark Roberge focuses on inbound sales. To balance this out, I strongly recommend educating yourself on outbound sales. Aaron built an SDR (Sales Development Representative) team at Salesforce.com, and many companies used a similar approach since then. Ross is saying that cold calling is dead and is suggesting a new way to approach people in a “cold” way. His method is basically about creating a high-quality list of potential ideal customers and proactively reaching out to them at scale and in an authentic way. The book is not very well structured, but there is a ton of practical and useful ideas. Think about it as a “playbook” or “practical notes” from the field.
The Sales Development Playbook: Build Repeatable Pipeline and Accelerate Growth with Inside Sales by Trish Bertuzzi
If you read Repeatable Revenue, and would like to know more about outbound inside sales, read this one. I have a feeling that Aaron focused too much on an individual case of Salesforce.com, which was great, but you can think about many other factors that helped Salesforce grow at that time and place. Trish gives a bit more varied perspective and adds more company examples.
Hacking Sales: The Playbook for Building a High-Velocity Sales Machine by Max Altschuler
One of the developments that made sales as a science possible was the rise of sales automation tools. There are hundreds of sales automation tools for every step of the sales funnel and Hacking Sales is all about these them. From lead generation, to lead nurturing, to CRM, to dozens of very specialized tools. Don’t get overwhelmed by the amount of tools he is talking about. In my experience, rare companies need to use them all. If you discover two or three new tools from this book and implement them, your sales effectiveness will definitely increase. Again, stylistically I would call this book “practical notes” rather than a “book”.
Books from consultants
There are many consultants out there who help B2B companies build their sales organizations (including System2Labs). The main advantage of the books written by consultants is a more fact-based approach (you'll see numbers not only opinions) and the fact that they've seen patterns beyond individual companies. VCs see patterns too, but unlike consultants, they don't have enough time to work with the company day-to-day and implement things. Just like with SaaS companies though, keep in mind what consultants are ultimately selling. If a company is selling a specific sales methodology or sales training, for example, they will not always tell you if their methodology does not fit your purpose or will be able to explain how it fits the bigger picture.
"Traditional" consulting companies (McKinsey, Bain, BCG, and boutique firms) regularly publish on sales and marketing topics, but with all due respect to my previous industry, I think most of these articles are so generic that they have limited use to startup founders.
The Challenger Sale: Taking Control of the Customer Conversation by Matthew Dixon and Brent Adamson
This is probably the most well-known book among the sales leaders who I met over the years. And it is also one of the most misunderstood. I suspect the misunderstanding often comes from hearing about the book but not actually reading it.
Challenger sale is about a sales methodology: what you actually say and do in a sales pitch (hint: proactively offer customer insights rather than trying to “discover” the needs she may not be aware of yet). If you’ve read some of the books above, you’ll know that sales methodology is just one small aspect of improving the sales engine. I’ve seen way more than one company conducting massive Challenger sales trainings to “teach” all of their sales force to “challenge the customer” without investing nearly as much (if anything at all) into building organizational and sales management capabilities around the Challenger sales. If you read the book, you’ll realize that the authors talk about a much wider change that needs to happen in the organization, beyond just sales trainings.
Another very important caveat that I’d like to highlight. In my experience, Challenger Sales is not universally applicable. It suits complex enterprise sales processes and many specialist or more experienced sales roles (e.g., sales engineers). Sales people require quite some skill, specialized knowledge and practice to pull it off. Don’t try it at home if you are in transactional, low ticket item sale with junior sales people, and if you don’t yet have great insights to challenge the customer.
Having said this, the book is very well and professionally written, it is a pure pleasure to read. You may not agree with everything, but it will make you think. Definitely a must read.
Sales Growth: Five Proven Strategies from the World's Sales Leaders by McKinsey & Company
This book talks about quite advanced sales concepts and activities for more established companies that operate in mature markets and have already fixed most sales basics. These are the companies who need to go an extra mile in the pursuit of often single-digit growth. Yet I would still recommend this book to startup founders because it is a professionally written, researched, and thought through book, which is rare in the sales-related literature. The book is not extremely practical, but it gives you strategic structural way to think about advanced sales management.
(Since we are talking about McKinsey, I would also recommend McKinsey’s Value: The Four Cornerstones of Corporate Finance from the same series to look at the sales growth from an even more strategic viewpoint. That is particularly important for founders to read in the day and age of downplaying the importance of profitability vs growth).
Now, I know this list may look overwhelming but as I’ve said there is no single book that gives founders and sales executives all the crucial knowledge that they need. Founders take a lot of pride in learning from failures, but I do have a very strong belief that learning by doing should be supplemented by learning from the professionals who have seen and analysed patterns. As a founder you may think that your situation is unique but from the outside, I see most B2B companies repeating the same mistakes over and over. Reading high quality books, forming informed hypotheses, testing them in practice, and scaling what works will put you in the top decile of B2B companies.
Enjoy the reading! And don't forget to take action.
At System2Labs, we’ve read all of these books and created own knowledge capital, frameworks, and tools. More importantly we’ve seen what works in practice and helped dozens of companies build or improve their sales organizations.
System2Labs is a full-stack growth consulting firm for B2B startups. We take a holistic approach to growth: from high-level growth strategy, to going deep on any specific sales and marketing topic. We help getting things done: the result of our work is a working sales engine, not a tool or PowerPoint deck. If you have any questions about choosing or implementing your sales ideas and would like to avoid common mistakes, get in touch!
Founder and CEO, System2Labs