How to Level up from $100/month SaaS Deals to $1M Enterprise Sales

Memoirs written by people in their mid-thirties tend to involve tales of hard living, steamy scandals, and other salacious subject matter, but Grant Miller’s story is one of a misspent youth struggling with…enterprise software product requirements. “Struggle” may be the wrong word, as he and his co-founder, Marc Campbell, managed to make themselves millionaires nine months after founding their first company together, but along with this new venture, Replicated (#ProudInvestor), Miller hopes to help founders enjoy a smoother path to success.

The 11 Principles of Becoming “Enterprise Ready.”

His autobiography takes the form of EnterpriseReady.io, a collection of resources that help SaaS founders understand the complex product requirements that come with selling to established businesses. He’s identified 11 features an application must have to be adopted broadly by large clients:

1. Product Assortment: Different versions of a product to meet differing needs
2. Single Sign On: Enable enterprises to manage users from a single, central directory
3. Audit Logs: Provide admins with a detailed trail of account activity
4. Role Based Access Control: Allow for the separation of privileges by user role
5. Change Management: Empower admins with tools to roll out features/product changes
6. Product Security: Demonstrable application security through best practices
7. Deployment Options: Data security + application overhead + flexible deployment
8. Team Management: Centrally managed collaboration with coworkers is a must
9. Integrations: Enable data portability by allowing data in and out of your app
10. Reporting & Analytics: Allow admins to demonstrate value gained from your app
11. SLA and Support: Big businesses are less forgiving than beta customers

At EnterpriseReady.io readers will find how-to guides and case studies that demonstrate successful deployments for each of these items. But beyond this laundry list, Grant has identified a few broad mindsets that founders can benefit from, even those who might be years away from pursuing enterprise sales.

Big Companies Aren’t Dumb

The most pernicious problem Miller sees is a belief among elite technical founders that big companies are dumb, or at least seriously behind the times. “The funny thing is that many founders don’t want huge potential customers like ‘stodgy banks’ using their apps, only cool, hip companies,” says Miller—though these founders may change their tunes when they need to live up to the ambitious valuations they accepted while fundraising.

These beliefs, by and large, are rooted in some truth. Behemoth corporations don’t adopt modern frameworks or design patterns rapidly. New UI paradigms take years to trickle into their products if they ever do. But these complaints miss the bigger picture. Massive conglomerates earned their size because they have built many successful lines of business that are in the market, producing revenue, and likely…profits. By default, these companies are more risk averse and more interested in protecting the status quo. On the other hand, startups are actively trying to exploit change to disrupt the status quo to create the market opportunity they need to thrive. For startups to be successful working with large enterprise customers, they have to recognize these inherent differences in perspective.

Photo Courtesy: Amplify LA

Miller adds that it isn’t just about risk aversion, “Founders often don’t appreciate the large differences in priority that comes with massive scale,” says Miller. “When a company has 100,000 employees, they can’t be managed the same way they would be at a 10-person or even a 100-person startup.” He points to Team Management, Single Sign-On and Role Based Access Control as examples of how enterprises need applications to be administered differently. A two person team might be happy to share usernames & passwords to access 10–20 applications (even then it’s a bad idea). But, for enterprises trying to engage tens or hundreds of users with an application, they can’t even think about managing each of their users in each of the proprietary user management systems for each application, there are just too many to manage manually.

Large corporations aren’t stupid; they just have a different set of constraints that many startup teams won’t truly appreciate unless they’ve run a large enterprise IT department (or struggled with meeting the requirements of these companies for years).

In the Enterprise You Sell “Through,” Not “To”

As iterated above, enterprises are not just large SMBs. Founders are often surprised by how much of the sales process is done through a champion inside of the enterprise organization versus a more direct process to a decision maker inside of a small business. Simultaneously selling to many stakeholders inside of a large organization — end users, corporate IT, finance, just to name a few — creates challenges compared to speaking directly with a person who will use your product and holds the credit card.

As a result, SaaS companies looking to move up market into the enterprise have to enable the people inside of large enterprises to spread the product horizontally and sell it up through their organization. It isn’t just about satisfying a single type of user’s direct business needs (though that is the first step) but the next step is to be able to meet the needs of all of the adjacent parties. For example, features like product security to pacify the CISO and audit logs to appease the compliance officer can go a long way in communicating that a startup “gets it”.

Beyond just building these features, SaaS companies should document how these features work in the form of marketing collateral that can be shared within an organization. Founders need to get comfortable allowing 3rd parties to push their product. Instead of wordsmithing every bit of copy, entrepreneurs need to orient their marketing to the multiple different audiences inside of a large organization, this means developing a wide variety of collateral in the form of PDFs and PowerPoint decks. These resources allow an internal champion to communicate effectively with other parts of their organization about the areas that each is concerned.

Once the deal is closed, and the customer is onboarding, Miller advises that SaaS companies think about how they can accelerate the career of their champion within these enterprises. Often these advocates have risked their hard earned relationship capital within their organization to support new technologies. One key he suggests is to embrace and provide air cover back to the champion by providing advanced reporting functionality to prove the business case & ROI that has been unlocked by the adoption of the product.

Listen for Common Requests

One warning: listen to and learn from these sherpas, but don’t let them design your software. You will hear dozens of feature requests from customers, but it’s the job of a great product person to sift through those ideas and to build generalizable tools that can be sold across multiple enterprises. EnterpriseReady can help give product leaders distinct buckets in which they can group feature requests to understand if they are common requests or just the personal preference of a specific customer. Often the biggest challenge is just being on the same page with the various parties within an organization as to what their requirements are. Find a common vernacular and specific example that you can reference when taking feature requests.

The Humble Art of Helping Corporations

Selling to the enterprise can be equal parts frustrating and lucrative. As easy as it is to poke fun at boring old behemoths, entrepreneurs should empathize with them — after all, the goal is to become one.