Modernizing RFIs — The Opportunity for Prescriptive Templates for Fortune 500 Tech Purchases

Jonathan Lehr
Oct 22, 2020 · 5 min read

Earlier this year, my colleague Priyanka Somrah published a well-researched landscape on IT Compliance and Security Automation. There’s a lot of innovation occurring in various slices of this market as modern GRC tools increase their adoption in the enterprise. (Stay tuned for an exciting announcement from us in the coming months about an investment we made in this space).

A related space that we’ve been exploring is modernizing the vendor evaluation process from a Fortune 500 buyer’s perspective. As is typical with many ‘aha moments’ that lead to startup opportunities, the current process involves numerous stakeholders across different teams, massive Excel sheets, endless conversations about capabilities and associated weightings of importance, and lots and lots of email. I’ve previously written about the opportunity that orchestration can play in enterprise efficiency, and this workflow fits the bill to a tee.

When you combine this clunky evaluation process with the macro trends that more startups are being created than ever before and the pace of technology is changing too quickly for corporate IT buyers to keep up, the timing seems well suited for a new approach.


One common complaint we hear from our Fortune 500 network is how to evaluate and implement new technology solutions from startups. I felt this pain first hand during my time at Morgan Stanley IT, where my team supported these cross-functional evaluations, and I remember one of my last projects was a Business Intelligence RFI and RFP process.

We used Qlikview, Business Objects, and TIBCO Spotfire across various parts of the firm, and in true enterprise form, we were wondering if we could centralize to a single vendor (hint: in the BI space, you’ll never accomplish this) and if there was any modern solution that could bring new capabilities to our teams. This led to hearing the latest updates from our existing vendors and meeting the newer entrant Tableau.

It took many calls (and a lot of chasing stakeholders) to get consensus around requirements, but ultimately we ended up with a long list in Excel. While that was confidential, I found an example from the Project Management Institute that gives a good sense of what these Excels typically look like.

There’s a lot of room for improvement in this process, and below are some areas ripe for improvement by modern solutions:

1. Requirements Templates

What are key criteria that you should be thinking about if you’re looking for a new BI tool? Or modern identity stack that extends beyond on-prem to various cloud environments? Or if you want endpoint security software?

From personal experience and conversations with numerous Fortune 500 IT executives, it appears that 80%+ of requirements will be similar across companies, and then the remaining 20% will be somewhat unique to an existing IT environment. As more organizations and their workloads make their way onto the cloud, this gap will decrease.

This is where marketplaces like G2 lack. While it’s nice to look up vendors and get a Yelp-like review on them, this only represents a piece of the pain. There is a significant opportunity to be more prescriptive into what you should be looking for, before even considering the who.

We’re seeing increased collaboration between companies in new problem spaces, with a recent example being the Open Network User Group (ONUG)’s Automated Cloud Governance white paper which featured significant input from IT executives from FedEx, Cigna, Raytheon, JPMorgan Chase, and Pfizer, along with participation from my Work-Bench colleague Kelley Mak.

Nailing requirements templates down will be tough, and while over time there can certainly be a community component to getting wide coverage, I’m curious what approaches startups would take to building up the initial repository.

2. Workflow

Before a project begins, there needs to be a clear Owner who will lead the process, and a Project Manager who will do the necessary internal chasing.

The software should handle the process and people component, and be able to assign whose input is needed and by when. With so many Fortune 500 companies on Slack or Microsoft Teams these days, plugging in things like automated nudges would help get the data needed in a timely manner. And enabling a quick sync with a few people on a specific question can resolve an issue quickly versus scheduling 10 days out when people’s calendars finally align or getting sucked into an email vortex.

We’ve seen the benefits that workflow improvements married to chat ops tools can have first-hand through our experience with our portfolio company FireHydrant. They bring tremendous efficiency to organizations when remediating incidents and reducing downtime during outages.

3. Integrations

RFIs are a piece of a broader purchasing puzzle, and as decisions are being evaluated, being able to combine this information with vendor risk management data-like security due diligence and financial health scores are critical for full context when deciding on vendor replies and scoring.

4. Knowledge Base

As refresh cycles occur in the future, you can revisit everything from requirements to their weightings to the actual performance of vendors evaluated, and make any tweaks necessary in future evaluations. This information is typically lost in inboxes after reviews are done, but the ability to revisit assumptions could be helpful for your company, and possibly become a part of a feedback loop for the broader platform to constantly refine the template requirement docs.

While these are just some of the capabilities that we’d look for in a modern solution, there’s of course more to be done in terms of how these questionnaires are shipped to vendors, how their responses are catalogued, and even how the pitches should occur.

Let’s Talk!

If you’re a startup working on a solution in this space, or a Fortune 500 executive who wants to improve your internal RFI processes, please reach out! I’d love to chat.

Additionally, if you’re a Fortune 500 executive looking for more answers on how to approach buying from startups during COVID-19, check out our Enterprise Playbook on the topic.


Work-Bench is an enterprise technology VC fund in NYC.


Work-Bench is an enterprise technology VC fund in NYC. We support early go-to-market enterprise startups with community, workspace, and corporate engagement. Sign up to get our digest of top content & industry news weekly:

Jonathan Lehr

Written by

All enterprise tech, all the time || VC @Work_Bench, Founder of @NYETM, and @KauffmanFellows Class 19 || I also tweet (a lot) about the @MiamiHEAT


Work-Bench is an enterprise technology VC fund in NYC. We support early go-to-market enterprise startups with community, workspace, and corporate engagement. Sign up to get our digest of top content & industry news weekly: