RFP Software Buyer's Guide

When it comes to buying an AI RFP automation tool, the marketing messaging can feel overwhelming.

Every product claims they have the latest, greatest model with the best features.

Every sales demo you watch can feel like the greatest demo you’ve ever seen.

How do you know who to choose or what to evaluate?

We made this RFP software buyer’s guide to help you categorize, evaluate, and rate vendors on a shared set of criteria.

Types of Tools 🛠️

Dealing with RFPs and compliance questionnaires is a pain point that Sales and IT teams face on a regular basis. There are a few routes you can take when trying to modernize this process.

This is by far the most painful approach. In most cases, a dedicated teammate will be assigned to own the questionnaire response process. In larger organizations, this can involve a full team with a complex workflow, and the need to maintain a large library of information. Most companies want to transition away from this costly and inefficient approach – in fact, we recently did a study on how long it takes to manually complete an RFP.

  • Pros: You can maintain control over the workflow from start to finish. Some people prefer this approach over using RFP software…for some reason?
  • Cons: A manual process is slow, expensive, and leads to bottlenecks in responding. This can slow down sales and frustrate teammates. The quality of responses can also vary as humans are left to read, write, and proofread a large amount of text.

These tools are more common among enterprises and larger organizations where the RFP workflow is high-volume and has many movings parts. If you’re looking for a large software suite that can help you ‘project manage’ a high volume of RFPs and questionnaires, this might be the category for you.

The biggest downside is that users report spending more time researching, manually writing responses, and maintaining a large knowledge base due to the lack of answer automation.

  • Pros: Enterprise-ready software with big customer names
  • Cons: Expensive, slow user experience, bloated interface, difficult to use, lacking automation
  • Examples: Responsive, Loopio, and Qvidian

Believe it or not, some revenue teams have tried leveraging traditional knowledge management and enablement tools to improve their RFP response workflows. Unfortunately, this is like fitting a square peg in a round hole. Though the user personas do often overlap, enablement tools do not address the pain points associated with responding to sales and compliance questionnaires.

  • Pros: Established software tools with good reputations among sales teams
  • Cons: High price tag, unable to address the specific pain point
  • Examples: Highspot, Seismic, Guru, Glean

In a similar vein, IT and security teams have tried using compliance software to address the questionnaire problem. While these are great tools for achieving infosec compliance, the technology does not translate well into the specific pain point of responding to complex RFPs and questionnaires. Despite some of these tools having questionnaire assistants, they are limited and still require you to research and manually write responses.

Furthermore, these tools get siloed into the security teams when in fact most RFP and compliance questionnaire activity comes from the sales org. This is why many of our customers use 1up alongside their existing IT compliance software.

  • Pros: High-quality systems trusted by IT and InfoSec teams
  • Cons: Despite their great reputation, these tools do not address RFP/questionnaire automation pain points
  • Examples: Vanta, Thoropass, Drata

This category is widely-considered to be the modern approach to automating RFPs and security questionnaires, and answering sales questions 10x faster. By combining Large Language Models with an automated knowledge base, tools like 1up deliver a user experience that addresses specific pain points.

The result is an automation experience that Sales and IT teams love to use daily at companies of all sizes. Here’s a demo of what that looks like:

Automate RFP Responses in Minutes with AI

Evaluation Checklist ✅

When evaluating questionnaire automation tools, you’re should benchmark them against a few key factors. Don’t just compare lists of features. Consider these strategic qualities in choose the tool that’s right for your team:

  • Answer Auality
    This is the #1, most important factor. Your responses should use accurate sources you trust. Answers should always be truthful with strong protections in place for incorrect responses. All responses should be formatted correctly with transparency on how they’re being generated. A slow, accurate response is better than a fast, dishonest hallucination.

  • Data Security 🔐
    Customer data should never be used to train Large Language Models. As for certifications, SOC2 compliance is table stakes, and should not be considered a differentiator. Instead, consider the vendor’s team composition and background – do they have a dedicated InfoSec function? How have they protected customers from data leakage? For reference, here’s a brief overview of 1up’s approach to data security.

  • Speed ⚡
    Answers should only take a few seconds to generate. Long, complex questions might take longer, but should still be much faster than it would take a human to write. A simple benchmark we use is that a questionnaire tool should be able to deliver at least 100 high-quality answers per hour.

  • Ease of Use 💤
    Your tool should be easy to use out of the box with minimal setup. Newly added users should get familiarized with the dashboard quickly, without the need for setup calls or extensive training. The easier it is to use, the faster you’ll get value out of it.

  • Trusted Knowledge Sources ℹ️
    You should be able to import a variety of file types and data sources, including gated webpages and 3rd party repositories such as Google Drive, Confluence, and more. A powerful knowledge base will automatically refresh itself to ensure your answers are up-to-date and accurate.

  • Workflow Flexibility 💪
    Users should be able to control their answer generation, sources, and knowledge base structure. A flexible system should allow users to influence answers based on pre-selected sources. Users should also be able to set statuses, monitor usage, and ensure that questionnaires are streamlined from start to finish.

  • Document Compatibility 📄
    You should be able to automate answers to documents in any format. Microsoft Excel, Word, PDF, and even web-based questionnaires should be supported out-of-the-box. When it comes to web-based question sheets, a good approach is to use an RFP questionnaire browser extension.

Finally, assess if the tool is actually saving you time.
Does the tool require you to continue living in Excel or Word Documents? If the whole point of looking for an automation tool is to get away from living in spreadsheets, then make sure that’s what you’re getting. You should be able to hand off a document to an AI, step away, and come back to a completed project ready for your review. Anything less is proof of extra steps.

Proof Points To Look For 👀

Ask for a specific customer story that lines up with your company size or industry.

If you’re a small or medium business, a case study explaining how a large enterprise adopted AI might not be relevant to you. Conversely, a tool that focuses on small, nimble teams won’t necessarily translate well to a large complex organization.

For example, 1up has been deployed across companies ranging in size from 10 to 10,000 employees. Here’s an RFP automation customer story for Tellennium, a leader in enterprise expense management. Here’s another for FusionAuth, a leader in the Identity Access Management space who use 1up to automatically generate thousands of RFP responses.

To dig deeper, ask for a reference of someone who has renewed their contract. The key to telling great customer stories isn’t sales, it’s adoption. Are they still using the tool? Why did they stick around? Why not?

Ask the hard questions and you’ll be surprised how many customers churn when it comes to RFP management software.

We’ve spent a lot of time reviewing the AI/Automation space. Every week you see a new jaw-dropping demo. What really matters is how these tools actually get adopted.

Matt Sacks, Lightbank

Finally, don’t just settle for online reviews.

I know, G2 Reviews can be a great signal, but remember that many companies trade Starbucks gift cards for a positive review. Yes, most of these are paid for, unfortunately.

Anytime a vendor flashes their G2 review badge at you, ask them to speak with a customer. There’s no better way to validate a review than by speaking with a reference.

Bloated RFP Software

Questions To Ask Vendors ❓

You want to cut through the sales speak and marketing noise? Here’s a list of direct questions you should ask the vendors you’re reviewing.

  • Are the answers provided a ‘cut and paste’ of previous responses, or are they tuned to new questions?
  • Does your tool automatically identify questions, or do users need to manually map out rows, columns, and questions?
  • Do users need to continue living in Excel or Word documents?
  • How fast can the system generate 100 answers to a questionnaire?
  • Does the tool connect to living document sources such as like Google Drive and Confluence?
  • Can the tool use gated websites and support portals to generate answers?
  • How does the tool support web-based questionnaires?
  • Can the system handle unstructured free-form RFPs?
  • When they say their tool has AI features, do they mean that new and unique answers are generated for questionnaires? Or does it mean it uses AI to ‘search’ for past answers?
  • How easy is it to maintain a knowledge base? Do users need to maintain a list of hundreds of Q&A pairs?
  • How long of a contract do users need to subscribe to? Is there a free trial period, and what are the limitations?
  • Does the tool actually reduce the amount of time or people it currently takes to complete a questionnaire? If so, by how much?
  • If the answer returned by the system needs tweaking or reworking, what tools does the system provide to help you accomplish this?
  • Can you ask the system one-off questions to get information you need to help with this?
  • Are support costs extra?

When It’s Time for Procurement 💳

Once you’ve selected your preferred tool, it’s time to pick a pricing plan and inform your finance team.

At 1up, our pricing plans vary based on questionnaire volume. All pricing tiers include unlimited single answer generation and free integrations such as Slack, Microsoft Teams, and Single Sign-On login.

At this stage, you may also be required to get approval from your IT/Security team. Depending on company policies, you might have to share a vendor risk questionnaire with your preferred vendor (how ironic).

Here are some considerations when procuring a tool like 1up:

  • Your legal team might have compliance requirements for deploying Generative AI tools. At 1up, our ToS already covers most requirements, but consider the possibility of an additional Data Processing Agreement to ensure all parties are comfortable.
  • Your IT team might ask that you complete a security review or to provide the vendor’s SOC2 report. This is a great opportunity to see if the vendor eats their own dog food. Ask them if they automated the questionnaire through their own product.
  • On rare occasions, you might ask the vendor to complete an MNDA. Confidentiality is most likely covered by their Terms of Service, but feel free to include it if necessary. After all, you are dealing with sensitive data.

Finally, make sure you can get a free trial. Don’t just settle for a demo. You want to be able to test multiple questionnaire types, formats, and answer modes. This is how you can ensure that your team picks the right tool for the job.