Spotting a Good Pitch: 3 Questions to Ask Yourself When Choosing a Vendor

Alex Lawrence
Pollinator: the Bloom Works blog
4 min readJul 7, 2021
A person is undecided between “Vendor 1” in one hand, and “Vendor 2” on the other.

As Bloom’s Growth & Operations lead, I spend a lot of time developing partnerships with governments and nonprofits to find equitable and human-centered solutions to their digital problems. But for many years, I was on the other side of the procurement process.

I was previously the chief of staff for the City of Boston’s Department of Innovation and Technology where I supported the day-to-day operations of the 200+ employees and contractors who provide core IT, digital, and analytics services across the city. I worked with countless vendors to co-develop products for the city or implement technology. For every vendor we worked with, I read or heard ten times as many pitches.

Which means — I’ve seen a LOT of pitches, from the good to the bad to the downright disingenuous.

When you’re working in government, time and resources are tight. You often find yourself wearing multiple hats to get the work done, with limited time to focus on procurement decisions. You need to cut through a lot of information — and you need to do it fast.

Over the years, I had to learn how to spot a good pitch quickly, and time again, I found myself asking the same 3 questions:

  1. Does the vendor understand my organization and the problem we’re trying to solve?
  2. Is this pitch clear and easy to follow?
  3. Is this pitch realistic?

If the answer is yes to all three questions, you know you have a good pitch.

Here’s why:

Does the vendor get my organization?

A good vendor will show empathy for your organization. It should be clear that they have taken the time to understand where you are coming from and that they are trying to meet you where you are.

I once had a vendor tell me that their software could allow our employees to select whatever laptop they needed out of a vending machine. If they had just looked around, they would have seen that every desk featured an outdated desktop. The example they used was about a decade ahead of where my organization was, and that disconnect was a big clue that they wouldn’t be a good match.

I’ve also seen a lot of people try to show empathy by pandering to stereotypes. If I had a nickel for every time someone who was selling to the City of Boston told me they thought Tom Brady was the GOAT or that they took two creams in their Dunkin’ Donuts, I would be wicked rich, kid. But I wouldn’t have the right vendor.

However, if a vendor took the time to use the brand guidelines on our website to seamlessly illustrate that they understood what we were trying to do, they got my attention.

Is this pitch easy to understand?

Here at Bloom, I’ve been lucky to be around people who’ve taught me the magic of simple communication and plain language. Whether we’re speaking to clients, stakeholders, or the general public, we lean on casual, approachable language.

It’s so tempting to say things in a fancy way to sound sophisticated, but language that’s accessible resonates the most. This is especially true for vendor pitches. I want to understand what products or services a vendor is offering, not how smart they are. Hiding behind big words or meaningless jargon isn’t going to get my attention. Clearly communicating the value they’re going to bring will.

Is this pitch realistic?

If something sounds too good to be true, it usually is. That goes for vendor pitches, too. If a vendor tries to convince you that they can solve all your problems, consider that a huge red flag.

In my experience, a product that supposedly solves everything probably won’t solve anything particularly well.

Similarly, if you hear that everything you want is “on a road map,” it might initially sound like the vendor is willing to bend over backwards to accommodate your wishes and needs. Over time, I learned that a trustworthy vendor is one who’s able to set a firm boundary with clear expectations.

What else to look for

Of course, when you’re looking for the right vendor, there’s a host of other things you need to consider. Do they have the skills to match your needs? Can they demonstrate past performance of having successfully done similar work? Do they have a pricing model that will work for your budget? There are many things you might be looking for in a partner.

And, of course, you should adhere to whatever procurement process and grading regulations your agency has put in place to comply with a fair, legal process.

But don’t overlook the more subtle clues. Make sure that the vendor understands the nuances of your organization and is trying to meet you where you are — and never underestimate the power of a straightforward and realistic pitch!

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Alex Lawrence
Pollinator: the Bloom Works blog

Growth & Operations at Bloom Works. Formerly Chief of Staff at City of Bostons Department of Innovation and Tech. Big fan of local government.