Your company has been wildly successful in targeting the SMB space, and maybe even the low end of mid-market. So maybe you say, “It’s time, lets go down the path of blockbuster companies like Salesforce.” Salesforce made its way from early beginnings selling to small businesses to multi-million dollar deals with very large enterprise customers.

What do you need to think about as you embark on this journey? I was at Salesforce for eight years, early in the evolution to large Enterprise deals, and so much had to change over time. Ten things to consider:  

• Does your product meet the more complex requirements of Enterprise? For example, security features, remote device management, permissions for limiting access by role, to name a few. And can you still support the simplicity needed for SMB customers, while building in the more sophisticated offerings for Enterprise? One could say that Salesforce has long sought to try and figure out this balance, not entirely successfully, hence the rise of other competitors in SMB such as Zendesk.
• Does your Sales team have the broad cast of characters needed to make a successful foray into the Enterprise? Most companies need a strong field sales team of experienced Account Executives able to make in-person visits and build relationships. And typically your Enterprise AEs need the support of Sales Engineers (2 AEs: 1 SE), as well as prospecting support from Business Development Reps (3 AEs:1 BDR). 
• Do you need overlay sales teams if you have multiple products that are significantly different? The overlay teams can help with more complex sales of different products to an Enterprise account. You will likely need to implement a double comp structure to ensure no protective behavior among “primary” AEs owning an account. Will your primary AE act as the quarterback for the account to ensure the relationship is maintained, and call in overlay AEs as needed? 
• Have you built the other support resources you need to close the deal? Other teams which need to be expanded include a deal desk for pricing, more legal support due to complex legal contracts and purchasing requirements to close the deal, etc. The Github CEO mentioned a few years ago that Disney came to them proactively looking for an Enterprise deal to aggregate all the individual Disney developers who had bought Github, and Github was shocked by the “sucking up of resources” that ensued to work through the contract.
• Have you changed your sales business model and approach to include the longer sales cycles, often 6-12 months, and the 10-15 stakeholders that can have a voice in the deal, and hence need to be educated and influenced? Have you considered all the personas and roles from whom you need buy-in? For example, while your product may be targeted at the CMO or the CRO, what are the pain points and risks from the viewpoint of the CIO? How about the CFO? 
• Do you have credible use-cases, customer stories and ROI calculations, ideally by industry, that speak the language of the customer’s business? Be as relevant as possible. For example, remember that “health care” is not an industry; you need to build use-cases and ROI for big pharma, for hospitals, for biotech, for medical device companies…each is different. 
• Are you showing up in the right places? Are you at the right events and conferences where the buyers and influencers are? Have you considered targeted custom marketing, e.g. ABM, to Enterprise prospects? Marketing moves more to the role of awareness & credibility building and nurture versus lead generation when playing in the Enterprise space. 
• How will you price your deals for Enterprise? You may consider pricing your first few deals with banner-name customers as loss-leaders. The first few big customers at Salesforce were priced at jaw-dropping discounts, as the credibility that came with having these customers onboard was priceless. Large customers will expect discounted pricing based on volume and on multi-year deals. And of course sales people will do what it takes to close the deal…to address this issue, you need a tiered pricing discount matrix, which mandates how much discount is allowed to what level of sales (AE to SVP), for what volume of deal.   
• How do you ensure successful implementation? Enterprise customers often require some degree of customization and professional services assistance. Have you developed the ecosystem to support your move to Enterprise? Do you have enough professional services personnel in-house to be able to implement what you sell? Have you figured out how to excite third party developers to implement and customize your product? And have you figured out how to train and certify them, to protect your brand and ensure smooth implementation of your product as demand increases?
• How will you drive retention, cross-sell and upsell? In SMB, of necessity this tends to be more mass-market and automated. In Enterprise, with the “land and expand” strategy dominating, you need to ensure you have post-sales teams, i.e. Customer Success Managers and technical support, to ensure the customer is successful in being onboarded and in using your product, understands the value delivered, and is likely to renew. And you will need to make your sales team accountable for ongoing cross-sell and upsell…some companies even make retention a part of the Enterprise AE compensation, as the primary relationship should belong to sales.

What are the key priorities, the “must haves”? In the early years of making advances into the Enterprise market, clearly it is not possible to do everything. There is no doubt that there needs to be an upfront investment that will only pay off after there is traction, which takes time. 

So how to prioritize? You need to use the same logic as the “minimum viable product” approach for your Go-To-Market strategy in Enterprise. Specifically, get something out there and see what sticks, iterate until something works and then do more of it. For example, you may find that your products are not as complex, and can be sold by the same AE, without much/any overlay support. You may find that specific industries are responding better, in which case you may go an industry-specific route to Enterprise. You may start with fewer prospecting resources, or fewer sales engineers, and see where the ROI on resources is highest. You get the picture. It’s all about tradeoffs.

Note that your profitability on a margin basis can be lower for Enterprise than it is for mid-market given all the additional resources and time typically required, but the profits and revenues on an absolute basis is what the game is about. And if you can manage to continue the focus on SMB and mid-market to generate the steady flow of business while embarking on your quest for Enterprise magic, it can be the best of both worlds. 

Nothing ventured, nothing gained.

Originally published on LinkedIn