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Sign On The Dotted Line: How To Keep Deals Alive

Has your SmallCo’s deal ever been stuck in what feels like “Contract Hell”? I bet it has, especially if you do business with BigCos.

Here’s how it goes: after numerous demos and follow-ups, you hear from your BigCo contact they’d like to pull the trigger. Great! If it’s your first time up to bat, you’re eager to sign on the dotted line and begin your implementation.

But wait… you’ve forgotten the consensus building, multiple approvals, vendor review, security audit, compliance checks…

And so on, and so on.

Often, in the midst of all this chaos, you wonder if the deal will ever move forward. Your customer’s priorities may change, or your contact may move to a new role, or enough time may pass that they have second thoughts…  Yikes!

While BigCos are process machines and there’s only so much you can expedite, here are some tips to make more of your “yeses” convert into signed contracts.

Keep In Touch

Certainly don’t spam your BigCo contact on a daily basis, but don’t be a stranger either.

Once the internal contact has stated that they are ready to move forward, set up a 15-30 minute meeting, to discuss and document next steps.  Be sure to capture the flow of what is required (sourcing, legal, security, etc.) ask for contacts in those departments, and to set your own expectations, ask how long the reviews in each of these areas typically take.  Another good question to your contact is, whether these steps must be completed in a serial set of steps and which once’s can be completed in parallel.

Close the meeting asking what the next step action is, and offer to take that action if able.  For example:

You:  “John, thank you for this information.  Sounds like we have some work to do here, before we can start getting you using our product.  Of the items you listed, what is the best next step to get things finalized?”

John:  “Well the first thing we need to do is get you connected with Carol in Sourcing.”

You:  “Sounds good, do you mind if I go ahead and send Carol  a note, with you on copy, introducing myself and getting a time set to start the process?”

Where possible try to ease the burden of your buyer, and this helps you maintain some level of control in the process also.

Now, with this process information captured, create a processing checklist, with the approximate timing of each task.  (You may be surprised at just how long closing the contract may take. Be sure to factor this in as you communicate expectations back to your investors and Board if these exist.)

Remain in contact with your buyer as appropriate in the process, but if a week or so passes due to a long process step, be sure to upset the opportunity to send a status of where you are at in the process, and include some engaging information relevant to your product  to help keep your customers excited. A well-timed email might even be the prod they need to expedite that review.

Just because contracts take a while to close doesn’t mean your business stops.  Keep your future customers informed of new features and developments that’ll make them even more excited to get your solution in play.

Documentation Is King

At some point, they’re going to want to see documentation. Before you even start the sales cycle, create detailed, thorough documentation that answers all the questions you can anticipate. Different customers often prioritize entirely different details (access and security over product uptime, etc.), so be comprehensive and amend your documentation over time.

Technical Resources

In addition to documentation, ensure you have sufficient technical resources on your team to explain how your solution works and what configuration is possible. It’s fine if you’re a non-technical founder, but someone needs to be able to explain the product. Many deals run into a dead end due to the lack of a solid technical resource on the team.

Audit Preparation

Don’t be surprised when the vendor audit begins. As your customers are higher on the Fortune 500 list, their processes will be longer and more thorough. This is especially true for highly regulated industries like banking.

Be prepared. Have your technical specs, financials, information security policies, and so on ready to go so you don’t add time to the deal cycle preparing audit materials.

If not already established, be sure you have a company EIN and DUNS number.  Don’t be surprised if the customer requires Errors and Omissions insurance, and cyber liability insurance at fairly high values.  Understanding these requirements with sourcing early in the process, can help you from getting stalled later.

Anticipate Obstacles

You can probably anticipate some of the obstacles you’ll encounter before you even start the sales cycle. Be armed with reassuring answers and all the appropriate documentation so you can navigate around the roadblocks rather than watching the deal get stopped in its tracks.


Getting the “yes” is only half (maybe even less) of the battle. Your ability to keep deals alive and navigate the closing process is critical to your BigCo implementations.

We specialize in preparing your solutions for enterprise implementations. Reach out to learn how we could help you!

Thomas Martin