Selling to the Enterprise #2: Avoid Saying No

Sorry Dave Nobody likes being told “No”

To sell your product to enterprise buyers, minimize the times when you need to say “No” during the sales cycle.

Enterprise software purchasing is a complex process with potentially innumerable stakeholders and procedural hurdles to cross. Even if you have a badass product that will perfectly fit your customer’s needs, you still need to wade through a complex buying process.

The decision to buy a product like Netflix is simple: I want to watch a once-in-a-generation classic like “Selling Sunset,” so I pay for Netflix to stream it into my greedy eyeballs. As an individual, I make the purchasing decision and enjoy the rewards alone (thankfully).

Selling Sunset I actually think that most of the characters on this show would be absolutely lethal at selling enterprise software

Contrast this to a buyer like the US Air Force deciding to use Slack – even just calculating the number of users that they’ll have is a non-trivial task, and that’s for a relatively straightforward, consumer-friendly SaaS product. Transformational changes – say, moving to the cloud – can be exponentially more complex. The number of stakeholder approvals and compliance hurdles that must be vanquished on the way to this sort of purchase boggles the mind, but this is exactly where you make your bones as an enterprise SaaS business.

Detractors Want You to Say “No”

Innumerable potential blockers can arise during a sales cycle: you’ll have to say “No” to a particular use-case provided by the product that you’ll be replacing, or explain why you lack a feature that a buyer was expecting from a previous job. In most cases these gaps are unimportant… but these blockers can really throw a wrench into the sales process.

Adversaries who oppose a new software vendor will latch onto any time when you don’t say “Yes” like a lamprey – poking holes in the case to buy your product. Blocking stakeholders are typically incentivized to either preserve the status quo or explicitly harm your case, and include:

  • Teams who are incentivized to minimize risk, such as Compliance, Legal, IT, and (in some cases) Security.
  • Teams who are frequently blamed if a poor buying decision is made, such as Procurement. Some companies also just have risk-averse, blame-heavy cultures in general.
  • Champions of incumbent solutions – for example, an executive who originally purchased the product that you’re replacing.
  • People who don’t want to do the work of changing to a new vendor.
  • Competitors.
  • (Rarely, but occasionally) people who are just nihilistic or obstructionist jerks.

One of the biggest enemies when selling to a complex organization is time. Buyers get discouraged if it’s taking too long to sign a new vendor, and there’s often a small window when a company is ready for change and the stars have aligned for them to drop some serious coin for it. Detractors will latch onto any “Nos” that they hear and use it to delay or kill a sales cycle. This is especially common when replacing a strong incumbent – you had better believe that Oracle knows every trick in the book to make it seem that your product is untrustworthy or incomplete.

In order to overcome this, allow your sales team to say “Yes” as often as possible. The client is worried about some niche use-case? We have a partner who will make it happen. The client wants a particular security feature? We can make sure that the particular risk the Security team flagged will be handled. The client needs to format their data just right for board meetings? With a little bit of elbow grease on the customer’s part, we can support it.

Ways to say Yes more:

  1. Make your product as flexible as possible - eg make everything programmable via API or expose webhook callbacks for all major business actions. This helps customers, consultants, or your implementation teams extend your product’s capabilities for use-cases that are unique to them, which you’ll never directly build yourself.
  2. Identify major gaps that will be a pain to build for, and find quality partners who can fill in these capabilities. Similar to the above, this allows you to cover niche functionality that only a few customers will need.
  3. Make it easy to transfer raw data into or out of your platform. For example, virtually every enterprise product requires some amount of internal executive level reporting, which is typically both critical and highly team-specific. By furnishing raw data exports you can check the box of helping to provide these reports. Being able to ingest or output large volumes of data also helps check the box of whether it’ll be easy to migrate to your product.
  4. Building common no-regrets enterprise features. For example, the areas of governance (SAML, RBAC), security (password controls, 2FA, internal endpoint protection), compliance (SOC 2, HIPAA), and audit logs are all areas where it’s easy to have a gap that will scare the shit out of a conservative buyer. By building for lots of use-cases in this area, you can ensure that you won’t get ruled out for missing features that are peripheral to your core value proposition.
  5. Find the right customers. If you’re constantly finding yourself saying No during the sales cycle, you’re probably selling to the wrong folks. This is common for early-stage startups or when your sales & marketing teams aren’t generating enough pipeline (forcing you to sell to weak leads). Having a very strong perspective on why your product is special, and who it’s special for, can help you to avoid this trap. So can having discipline – you’re often better off doubling down on making your core customer deliriously happy than stretching for a flashy new logo.

Note that the strongest form of #1 and #2 is turning yourself into a platform that others can build on top of.

Case Study: Salesforce

Salesforce has a decent product. It’s by far the dominant player in the CRM industry, but it’s hardly a loveable product like (say) Zoom, Uber, Datadog, the iPhone, or even Excel. However, Salesforce has used this product to become the #1 in their industry, in part because their team can sell the hell out of it.

If you look at Salesforce, you’ll see that they use all of the techniques described above to ensure that they always have a story for how they can deliver, even if it requires extra integration work. Combined with their ferocious marketing, it’s little surprise that they’re approaching a $200B market cap as of this writing:

  • They’re well instrumented with open APIs, and use ampscript to build custom functionality.
  • They have an app marketplace built on these APIs that’s filled with niche solutions, creating a platform ecosystem, and will also acquire companies to fill product holes.
  • They have a robust set of reporting and data import/export functionality, allowing complex organizations to onboard rapidly with services (if necessary).
  • Salesforce has a metric ton of enterprise features, and also aggressively moves to support new platform expansions that enterprises might want, such as migrating to Microsoft Azure for their hosting.
  • Salesforce’s target customer is well-defined and obvious – it’s literally in the name.

Case Study: Slack

Slack got its start by selling to smaller organizations and startups, but has since extended their reach into the enterprise. As time has gone on and they’ve begun to see real competitors, they’ve used all of the this post’s enterprise sales tactics to continue to move up-market:

  • They have a web of Slash /commands, webhooks, and APIs that allow for easy integration.
  • They used these tools to build a successful app marketplace, completing the platform strategy.
  • They once made it dead simple to migrate from their once-largest competitor, Hipchat (they’ve since killed Hipchat in their sleep like Washington crossing the Delaware). They still provide this for Microsoft Teams.
  • Slack is now packed with enterprise-grade security and compliance features.
  • As a horizontal SaaS product, Slack is a good fit for many organizations and relatively unlikely to find a particularly bad-fit customer.


Saying Yes often (or saying No infrequently) is important in enterprise sales cycles. To find more ways to say Yes:

  • Build a flexible product with programmable hooks.
  • Fill niche functionality with partners, turning yourself into a platform.
  • Make it easy to import and export data in bulk.
  • Build no-regrets enterprise features.
  • Sell to the right customers.