What I learned from Some of the Tech Industry’s Smartest Sales Pros

Date Updated: Monday, May 20, 2019

When people ask me about my role at Microsoft for Startups, they are often trying to understand the nature of our business and what exactly we do for startups. It’s easy to summarize with our slogan “You’re here to do great things. We’re here to help.” And indeed that is what we’re trying to do.

Of course, it goes beyond that and our level of support runs much deeper. We aim to provide a host of resources, from technology to marketing support, and everything in between. At its core, Microsoft for Startups exists to alleviate the specific challenges and pain points that startups face.

One of those critical pain points, especially for B2B startups, is building a sales team and strategy. A lot of founders and entrepreneurs, especially in the technology space, understand how to build an amazing product. That doesn’t mean, however, that they have experience building a sales structure that is capable of selling their product to other businesses, especially large enterprises that operate at massive scale.

sales playbook new

We heard again and again from founders that "sales" is at the top of their list of things they need help with. So, I set out to build an in-depth strategy guide that can help founders build a team, create a sales strategy, and implement that strategy in short order.

That's how we created The Sales Operations Playbook, a 90 plus page primer that can help startups, or any professional, learn how to build and operate a sales organization.

So now that you’re interested in reading the sales playbook let me make a confession - I’m not a sales professional. That is a bit of an odd confession to make in a post introducing a Sales Playbook. However, throughout my work helping startups scale their businesses I have had the opportunity to meet some of the most talented sales professionals in the industry. So that is who I tapped to help create this guide.

We gathered the insights of 15 senior sales professionals with deep firsthand experience building effective sales teams and strategies. These leaders have diverse backgrounds and come from startups in a number of sectors including: data analytics, AI, and fraud prevention.

A sample of some of the chapters demonstrates the kinds of insights they shared

· Building your sales model

· Managing a sales team

· Entering new markets

· Negotiating the best deal

The Playbook is of course too long to summarize here, but I wanted to share with you some of the insights that we gathered when we created it. I asked just two of the amazing professionals who contributed to the Playbook to share a key insight into their sales philosophy. I think they both demonstrate the kind of thinking that you can find in the full document:

Three Golden Rules of Sales - Stefan Groschupf, Automation Hero

“Number one, you want a person who can build your sales team who is more process and data driven. Often companies hire sales professionals based on their personality -someone who is an extrovert – but often overlook whether that person is process and data oriented.

“Rule number two, you want to be very data driven, you want to A/B test – everything. Your messages, your landing pages, your pictures, who you’re reaching out to. You want to consistently measure and improve three key metric: volume, how much is going into the funnel; conversion rate; and the last is time because time is money and most startups run out of money because their sales motion is too long.

“Number three, work on your messaging. You want to talk about your product as a pain killer, not as a vitamin pill. Everybody would be happy to take a vitamin pill every morning, but if you forget it’s no big deal. But if you pinch a nerve, you rush to take a pain killer. Bringing it back to sales, you want to very concretely communicate the business value your product will bring, and not just suggest that it’s a “nice-to-have” solution.”

Founders Should Close the First Deals - Dr. Jens Hutzschenreuter, Digital Business Group

“It’s crucial that the founder have experienced the pain of selling the product themselves. They need to be super close to their customers and they should be the one’s getting the first 10 contracts.

“Once they figure that out, it’s a great moment to hire more people and to start to delegate these things out to the teams. Why? I have seen a couple of teams before where the founders stepped away really fast and kind of lost the grip on the sales function. New people come in and they don’t know the product as well as the founders themselves. As a founder, you want to be able to say to your new sales reps, “I sold it myself, so here is a template for you to sell it on your own.”

Whatever your business, and whatever the current stage of your startup, if you are going to succeed, you will need to be able to sell your product. I hope this Playbook can help you streamline the process of building your sales team, but more importantly, I hope it will help your startup become a success.

You can download the playbook here.

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