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Selecting a contract management solution and partner is a major decision for your company. One that involves a financial investment and most crucially your precious time.

Centralising data, working with the new partner, building workflows, ensuring user-adoption, training, documentation - they all take time.

Just look how long it has taken you to get to this stage.

The last thing you going to want to do is have to complete this all over again.

Yet this is what we see at Gatekeeper time and time again. A company comes to us either fresh from another implementation or within a year or so of investing in a competitor solution.

Whilst it is tempting to select a simple solution to meet the immediate contract management pains of a company, there are no short-cuts. Centralising and cleaning your data takes time. So does engaging with the new partner team and embedding the new solution within your user base.

Outgrowing, running into major limitations or simply finding the cost prohibitive as you grow in your chosen solution can actually set your business backwards as you find yourself a year or more down the line, with money and time committed, but with nothing functional to show for your efforts.

Here at Gatekeeper, we understand it is very hard for you as the buyer. Contract Management is not a ‘compare apples with apples’ marketplace.

Today, with ever more solutions to choose from, it is easy to select a solution that stands out as the cheapest or apparently the simplest to use and miss some important aspects that are not clear at the time but become a reason you need to move on.

This is why we have created a simple list of questions that you can send to any potential provider and decide for yourself if they can support you in the long term:

Pricing & Growth

  1. If we scale quickly and double the number of users what is the cost implication?
  2. Does this additional cost cover your licenses and e-signature licenses? If not, how much for both?
  3. Whilst our primary focus is on the Legal Team’s requirements, how does Procurement, IT, Finance, Compliance also use this system?
  4. What are the cost implications of allowing access across the business?
  5. What features do you have for them so the data does not become siloed in our department?
  6. Is your pricing transparent and listed on your website?
  7. If not, how do I know you will not double your pricing on renewal like a lot of fast-growing startups?

Look and Feel

  1. Can I brand the solution to make it feel more 'built for us'?

Data Control

  1. Do you have import processes in the UI we can use to add data?
  2. Does this support any custom data we have added?
  3. Do you have export processes in the UI?
  4. Can we also update/merge existing data in this way?

Data Security & Sovereignty

  1. Data security is very important to us. Are you (not just your hosting provider) ISO 27001 accredited?
  2. If so can you provide your certificate?
  3. If not, why not?
  4. Data sovereignty is very important to us. What options can you provide for data hosting locations?
  5. Are you independently audited for security?
  6. If so can you provide the latest reports?
  7. If not, why not?

Regulatory Audits

  1. Does the system record all changes to all records?
  2. If so can you show me this report based on our last demo?
  3. If not how can I support any audit or regulatory review?


  1. Can you show me how reporting works within the system?
  2. Can I export these reports in CSV for processing?
  3. Can I export these reports in PDF so I can share them internally? These should be branded and clearly show the name of the report and date.
  4. Can I report on custom data added to the solution?
  5. Can I view data by department with associated reporting?
  6. Can I view data by internal entity with associated reporting?
  7. Can I view data by category with associated reporting?


  1. Does the solution have a published API?
  2. Is this updated when custom data is added?

Product Roadmap

  1. Can you share your product roadmap?
  2. Can you send me the link to the last 3 product releases?

Reference Customers

  1. Can you provide 3 reference customers we can contact at the final stage in the process of a similar size in terms of users and deal size?


  1. Can your contract management solution integrate seamlessly with our existing tech-stack, for example, NetSuite and Salesforce.  

To make comparing suppliers easy for you, we've put these questions into a simple spreadsheet that you can download below. No details to enter, simply click to download immediately.

Download Free Questionnaire Template >>

Whatever company you select for your contract management needs we wish you all the best on your journey and hope you find a partner for the long-term. Good luck!

Patrick O'Connor
Patrick O'Connor

Patrick is CEO of Gatekeeper, with over two decades of contract and commercial negotiation expertise, predominantly in IT and Technology.


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