Enterprise Software Sales and the Role of the Startup CTO

Enterprise software sales

Selling major Enterprise software is very different to selling “off the shelf” products.  Beyond the technical challenges, the startup CTO can make a major difference in winning these critical accounts.

From the startup CTO’s perspective, Enterprise software sales are really about 3 things…

Enterprise Software Scale

Enterprise software tends to have a much larger footprint than other types of software once deployed.  This has to do both with the size of the deployment itself, as well as the number of other systems it touches.  A deep understanding of both market trends and specific customer challenges when it comes to integrating infrastructure are key to ensuring successful engagements.  What you learn about customer architecture should also influence future technology strategy. This is different than features and functions, it’s more about usage patterns and trends.  Think about what problems the architecture is solving, at ultimate deployment scale, rather than the immediate integration challenges themselves.  If you are the CTO/chief architect of a startup, you are best suited to understand and articulate this.


Building and maintaining relationships when selling Enterprise software is vital.  Startup CTOs should aim to establish 2 key relationships: the technical decision maker, and the technical influencer.  When engaging enterprise accounts, your sales team and/or fellow executives (depending on how you are working the account) should be able to make warm introductions to these individuals.  A relationship with the business decision maker is also valuable if you can have it, but be prepared to focus mostly on ROI with this person.

Naturally you want to meet and make yourself available to as many members of the customer team as you can, but the technical decision maker (e.g. the CIO, VP of IT, etc.) and the technical influencer (e.g. IT Manager, etc.) are key to maintain a strong cadence with.  In general, enterprise customers buy 2 main things: time-to-value, and peace of mind.  Your role is to convince the technical influencer that purchasing your technology will save them time and effort versus building it themselves or buying from your competition.  As for the technical decision maker, you have to convince this person that your company is technically competent and it’s safe to do business with you in the long run. In effect, your job is to win “hearts and minds”.

There is another very important dimension to relationships besides convincing the individuals themselves.  By Developing trust and rapport helps overcome the customer’s company politics.  Unfortunately, politics play a huge role in most organizations.  The key thing to remember is that no one wants to be on “the wrong side of history”, so they will either support you or they will do everything they can to stop you.  Most of the times it’s passive aggression that you have to watch out for.  If you can convince both the technical decision maker and the technical influencer that they’ll be on “the right side of history” by choosing your technology, they should be able to corral their internal politics.  If they can’t, either you are dealing with the wrong individuals, or the deal is not properly qualified. My advice there: “fail fast”, or risk sinking tremendous effort into something that like won’t bear fruit.


Enterprise software is about longevity and predictability.  It’s a major, ongoing investment in both time and money.  No customer will commit a large amount of resource without understanding your vision for their needs specifically, but also for the market in general.  Because your company is neither Microsoft nor Google, who spend big money to do it publicly, chances are you’ll be the first person to brief them on your vision.  An enterprise software deal is like a partnership, so it’s very important that the customer understands and buys into your long term vision.

Vision is not about features and functions nor “pie in the sky” ideas and missions.  It’s really about 2 things: How your technology strategy can improve your customer’s operations both now and in the future, and how­­ you anticipate market trends that matter to your customer.  If you can convince the customer that you understand their pain points, and your long term technology strategy will alleviate these while freeing them to do better things, you’ve won half the battle.  If you can convince them that you understand what’s coming (and relevant to them) in the next 5-10 years, and how you’ll help ease their adoption of these technologies and processes, you’ve won the other half of the battle.  In short, your vision “future proofs” the deal for the customer.  It’s as big a part of peace of mind as whether or not you’ll be in business in the next 5 years.  In fact, a strong vision that is both market and customer relevant is a good indication that you’ll make it.  While no guarantee, it should be enough to convince the customer you’ll be a worthy technology partner for them.  Remember, when articulating your vision, keep it focused on the customer’s interests, and avoid boring them with detailed feature roadmaps.  Let’s face it, whatever features you see on a slide today are likely to change tomorrow.  What really matters is your technology strategy – where are you headed with all this?  Once that’s clear, the features tend to sort themselves out, and customers know this.

In summary, the CTO is one of the most effective Enterprise software selling tools a startup has.  Be sure to plug in from the beginning on important accounts.  Since building and monetizing product are the only 2 things a startup should be focused on, you as the CTO must be heavily involved in both.

About Leo Reiter

Gen-X tech entrepreneur with over two decades in diverse fields of the software industry, and a passion for expressing myself to anyone who likes to listen
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