Insights | Sales

4 Lessons From Selling Enterprise Software

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Michael Brown

March 26, 2018

Selling enterprise software is no easy task. Your startup is less than a few years old. You are selling products that are over $300K ARR. The sales cycles are long and deep. You feel like you never have enough pipeline to hit your numbers. In no particular order, here are a few things that we’ve learned that are foundational to the way we think about helping founders and their sales teams in the enterprise environment.

1. Talk To Everyone. As many early sales reps know, your product and your team is a puzzle that is hard to put together in the first months on the job. Get out there and talk to as many people as you can as quickly as you can. For prospects – no matter how much you study your product or your pitch, you will learn less than half as much studying and practicing as you do in a prospect meeting. Get as many touches as you can. For customers – they can easily be overlooked because you have to get new business, but your current customers are the ones who use your product and give you feedback. Listen intently to these people. For internal people – sit down with as many people as you can and get to know what they do for the company and what they’re working on. The list goes on and on. Talking to everyone is one of the best learnings from selling enterprise software that our team constantly imparts to our founders.

2. Set Up Infrastructure That Forces Internal Communication. Salespeople usually have a ton of pride, and they hold a lot of their cards pretty close to their chest. When it comes to sharing information and learnings across a team, unless something is set up to force everyone to share these ideas, it probably will not happen. This ultimately lowers the caliber of the team overall, even if the individual members of the team are very talented in their own right. Communication is the currency, and people learning from each other’s deals could immediately be applied as soon as that afternoon or the next day. Set up a recurring meeting about current deals in the pipeline. Pick a few deals and talk about what went well and what went sideways, and how to move the deals forward. It will help everyone. A big key to this as well is to have the head of sales, CEO, or other leaders depending on how big the company is. Everyone will show up and will try to add value in some way.

3. When You Think It Is A Deal…It Usually Is Not A Deal. One of the biggest things that we see lacking in early stage companies is effective sales qualification frameworks. Founders are generally trying to maintain some sales velocity and feel that they should talk to as many people as possible. They don’t want to lose that big logo and feel that they can solution sell their way to a deal happening. This never works. You’ll get told that a prospect is close and they just need you to talk to one more person. They’ll force “reloads” on you constantly. They will lob in some busy work to buy time and keep you warm. If you ever find yourself using qualitative terms and saying things like “I think this is a deal” know that the deal is probably not happening. Selling enterprise software requires a strict and formulaic criteria so you can eliminate time wasters. Make sure you implement a qualification framework and be OK with the fact that your pipeline may be thin for a long time.

4. The Proof Of Concept Is Generally Your Most Effective Tool. We’ve talked a bunch on the Bowery Capital blog about proof of concepts. The reality is, they work well for these type of sales environments and are one of the biggest learnings when selling enterprise software. Create a lighthouse program and invite some of your late stage opportunities into it (watch your conversion go up!). Introduce the concept early and often into conversations. Build pricing and legal stop-gaps by using this strategy. The more you can do to make the ICP get excited or approachable from a purchasing standpoint the better off you are going to be. Use proof of concepts as much as you can to start getting quick wins.

If you liked “4 Lessons From Selling Enterprise Software” and want to read more content from the Bowery Capital Team, check out other relevant posts from the Bowery Capital Blog