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Selling to Enterprise: Why Your “Easy,” Developer-Friendly Offerings are HURTING Your Chances

Great SaaS products and platforms attract developers and inspire them with the “art of the possible.” This entails education, evangelism, hackathons, API’s, sand-boxed developer environments, and a “quick and easy…try it yourself” type of mindset. Their customer is a developer, and their product is perfectly tuned for her.

Great platform companies align their processes to attract great developers, hiring people who come from these communities and who are comfortable in the environment. And this is precisely why they have a very, very hard time penetrating an enterprise.

Let me share a true story with you.

I was visiting a very successful platform company and was asked to sit in on a sales call. The company had interest from a large corporation that had signed up for a free developer account and had some questions before they could move to a larger commitment.

On the client side, there were no fewer than eight people on the GoToMeeting session, led by a senior architect, flanked by various security, infrastructure, and developer resources.

On the SaaS/platform side, there was a newly hired account executive and a dev-evangelist / pre-sales engineer type. The conversation started off this way:

Corporate IT guy: We signed up for the free account and are interested in exploring how this solution could be leveraged across our entire company.

Platform fellow: Awesome. How can we help?

Corporate IT guy: Well, we have a list of 32 questions, which comprise our diligence checklist for new tech vendors. Also, we wanted to see how your solution could be used to tackle “XYZ.”

Platform fellow: We love doing XYZ! It’s SOOOOOO easy. Let me show you how. I am sharing my screen now. Okay, so I’m logging in with my credentials. Can you see it? Good. Okay, now I go over here and click on this, and then I get this API key and go over here, and then I paste it over here.

And then I go to this page, scroll down, and… Do you see this??? Well, this is where I would insert the blah blah blah command, and then I go over here and switch to this mode, and then I enter this in the field. Voila! As you can see, this little program I created did that perfectly.

Corporate IT guy: [SILENCE]

Platform account exec: Hey guys? Did that answer your question?

Corporate IT guy: I think so. Perhaps we can move on to pricing.

Platform fellow: Here, I can show you pricing. It’s free to start! How awesome is that! It’s right here. On our pricing page. See? You just click on “pricing” and it shows you how we price our platform/API. It’s right here. See? You start paying only after you switch to Pro-mode. Awesome, right?

Corporate IT guy: Uummm. Okay, I guess. Perhaps we can go to documentation now.

Platform fellow: Well, that’s right here, too! Just click on Developer Quick Start and you can see, right here, all the documentation for our API. There are some cool examples that we wrote all our stuff for, so it works perfectly with ALL platforms / languages / protocols, like AWS / Ruby on Rails / Node.js / Hadoop / JSON…

Corporate IT guy: Okay, can you guys give us a proposal?

Platform fellow: It’s right here. You go and create an account, which you have, and then you enter your credit card when you need to buy more of our stuff, and then you use it. It’s right here. So is our pricing. That’s right here. And our documentation is right over here.

Corporate IT guy: Okay, let us go over what you shared and we’ll get back to you. Thank you.

Platform account exec: Great! We are looking forward to working with you. Thanks. Bye!

It was a train wreck. It was well intentioned, but disastrous, nonetheless. The entire experience made the corporate team feel stupid, and even useless. You see, corporate IT is about structure, waterfall processes, procurement, and customization. The corporate IT guy is rarely the economic or business buyer, but rather one step in a lengthy, twisted cycle called the RFP.

An RFP, or request for proposal, is the most common method for corporations to select and procure services/products from new vendors, or to address new requirements. Once entrenched, you will likely have a Master Services Agreement and Site License that will govern ongoing product sales or service delivery.

But to start, you will likely need to tackle the request for information (RFI) or RFP. The RFI is a lighter-weight version of the RFP, and trust me: these things are gamed from the very beginning.

Pro-tip: If you must respond to an RFI/RFP, change the requirements, insert new ones, or get them to change the rules for you. If you don’t, you will lose. Why? Your competitor, the big, slow, incumbent, helped write the RFI/RFP.

Let’s examine two key messages most platform/API companies use when communicating with prospective users of their service (“free” and “easy”), and how they impact a corporate IT person.

“Free” assumes that your customer sees the price of the product as the key friction point in trying your product. While this works when dealing with individual developers, it actually backfires in corporate settings. Corporate procurement and accounting processes literally require that they pay some amount of money when trying or buying a solution and that they allocate said expenditure against someone’s budget.

Corporate IT will charge the same person for their time against the project, and it sucks when the labor/service piece, even if it is internal, is much bigger than the product cost. So when you are “giving it away for FREE!” you actually are devaluing the time / expertise / organization of the person you are trying to recruit as a new customer.

“Easy” to them means they may lose their job. It means you don’t value the specific nuances of their company, products, culture, or processes. It means they won’t need weeks of training and certification, something many corporate IT people covet, as a badge of achievement and progress.

Incidentally, most of the corporate IT personnel I have encountered are hard working, smart, well-intentioned people. They are deeply committed to their companies, and most of them truly believe in their internal processes and their purpose.

So how do you fix it?

7 Steps for Wooing Enterprise

1. Create a different product category; call it “BLANK for Enterprise.” This tells them you want to serve them and have thought through the requirements of dealing with an enterprise company. The actual product differentiation doesn’t need to be large/significant. It’s about packaging and delivery.

2. Charge 5 times more for it. Charge for professional services. Create a training and on-boarding offering, delivered onsite for the client, and sell it as part of every deal.

3. Give them a proposal, which includes a Statement of Work (SOW) for the services portion of your engagement, along with a custom pricing schedule. I know your pricing is published on your site, but trust me: they want to see something that was tailor-made for their requirements.

Speaking of requirements, make sure you start the proposal with a section playing back their requirements, what you understood from them, and how your customized your offering / product / services to address them.

4. Make sure you visit them in person (if/when qualified), and dress as they do (ask them what the dress code is). I get that you enjoy flip-flops and taking Skype calls from your apartment, but that’s not how corporate deals are won.

Apart from the sales impact, getting out of the building is good for you. Nothing informs your thinking like building empathy, and the best way to do that is to put yourself in your customer’s shoes, and see the world from their vantage point.

5. Tell them you work with partners (even though they can “do it themselves”). Partnerships, especially with services firms, signal size and viability to many corporations.

Besides, the company you are targeting is probably already working with IBM, Accenture, or some other large systems integrator. They can play a role in determining your success, or could even be sitting across from you when you are pitching the company. If you’re serious about the F500, start building those partnerships NOW.

6. Create a different sales process for them. Don’t have them fill out lots of forms or enter their credit cards to get started. Get them on the phone, as quickly and easily as possible. Having a persistent, visible phone number can improve your chances of converting a prospective enterprise buyer, and in some cases is a requirement for your company even being considered.

Don’t “show up and throw up.” Let them talk as much as they need to. Let them tell you about their work, their company, their project. Make sure you don’t start the first meeting with a product demo! You are not going to “close the sale” for a large dollar amount with a big company in one meeting, so calibrate all other steps accordingly.

Your goal should be to “qualify” and make sure you are, in fact, a good fit for them. Don’t make them feel stupid or slow or not as cool as all of the other great customers you have.

Pro-tip: These guys don’t do hackathons. They do NDA’s. That would be a non-disclosure agreement. They take secrecy seriously, and they don’t share their plans with the public. You want to make them feel at home? Send them a bilateral or mutual NDA.

Double Pro-tip: They won’t sign your NDA. They will send you their version. But they will love the fact that you even knew to include it in the process.

7. Do business with people. I get that everything you built is set up for self-service, including your awesome FAQ and sign-up flow. But at some point in the process, make sure to include your CTO/COO/CEO and have them engage with the prospect.

Power respects power. People do business with people. So try to get them to introduce you to their management. (You could say “Our CTO took personal interest in this opportunity and would like to join us on the next call…he would love to say hello to your CIO and make sure to answer any questions she has directly.”)

There is nothing like looking someone in the eye or a handshake to signal trust, confidence, and parity. Doing business with large companies (and even small ones!) is about connecting with people (many, at different levels), in an authentic manner, on their terms. If they prefer to call for support, give them that option. If they prefer to meet in person, do it.

Now go out there and make it happen.


About the Author: Talieh is the cofounder/CEO of Drumbi, a tech startup based in Southern California focused on improving inbound phone conversion rates for businesses and improving the customer experience. Previously, he was a Partner at Accenture, leading the Products Operating Group in Los Angeles. He loves Quora and Twitter. Here he is on LinkedIn.

  1. Great tips.
    I have always enforced the “Easy to use and easier to buy” aspect of all eLearning products my company developed. And while this is really cool for individuals (in this case, teachers and/or consultants), we always had trouble when trying to sell to enterprises.


  2. Spot on Michael. Startups tend to undervalue their product offering, especially when positioned in front of large companies.

  3. Krista Bunskoek Nov 29, 2013 at 10:57 am

    Great tips Shervin.
    You’ve summarized the corporate/ SaaS sales relationship to a ‘tee’. We tend to focus on the “free” and “easy to use” when selling to the small business user of our online marketing tools.
    Corporations have the structures you outline, and to sell them you need to speak their language.
    Thanks for sharing.

  4. Sean Sherwood Nov 29, 2013 at 1:26 pm

    This absolutely describes our first enterprise engagement. Really appreciate the insight into the enterprise mind, it really is a different beast.

    Thank you.

  5. Many Thanks for this article. We plan to do an enterprise offering. And this article is a good advice how to deal with the enterprise world.

  6. Bookmarked. Great insights. Enterprise customers are sophisticated and need special attention.

    Thanks for sharing!

  7. Michelle Wetzler Dec 03, 2013 at 11:50 am

    Former Accenture manager and systems integrator, now running a platform analytics company. You hit the nail on the head. Thanks for sharing.

  8. I’m quite blown away by the lack of comments about the absolutely clueless sales rep behavior. He (or she) is obviously not listening, not following the line of questioning nor aligning with the client and has completely ignored the role of the sales engineer.

  9. Wow, thanks for throwing a curveball into my usual reading lineup. It’s not often that I get a paradigm shift into the corporate world being the untraditionally educated fool that I am. Some really good points were made that would have probably taken me several failures to learn the hard way when being contacted by corporate/enterprise level prospects.

  10. What an excellent article. Great advice and tips. Enterprises are totally different story.


  11. Some really great tips here as well as confirmation of changes we’ve made to our processes. These are precisely the issues we’re grappling with.


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