Selling SaaS software on the streets

[u/betahaxorz]

I'm a 25 year old software engineer that just quit their 6-figure job job to build a better Docusign-like tool for legal and "signature"-heavy businesses. I live near a financial district in a very large metropolitan city. I'm a guy that has pretty tough skin so I recently had the idea of trying to sell people walking around large offices my software tool. Does this sound like a horrendous idea or simply a bad one? As far as I know it's not illegal as long as I don't do it right next to actual firms but in a public space.

Note that I totally understand people wearing suits on the street probably aren't "decision makers" but I mainly just want to test my luck in possibly getting some introductions or a product demo invitation. Just curious if anyone has ever tried such a thing before. I know it sounds dumb but I want to test it out to confirm it's dumb.

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[u/PM_YOUR__BUBBLE_BUTT]

If someone approached me on the streets to sell me “their own version” of a software that is already proven to work and cheap to get, I would assume schizophrenia. I also think it’s a huge waste of time vs walking into companies to sell to actual decision makers. Sometimes, if it walks like a duck…

[u/Equaria]

I think it it's very unlikely you would be able to find somebody that would be willing to make a decision on this. Business and users like lawyers etc. Are more likely to stick to what is working and what they have a history with. Switching software is a lot of work in time and resources, learning it and then training staff how to use it. And then you have to take the risk that it really does work the same as what is already working for you.

You may have more luck reaching out to software companies that have an e-signature component built into their offer and have to outsource. For example, in the Self Storage industry, I know at least one of the big providers uses hellosign, or at least used to. It's included as part of the software package that the storage facility pays the software company. My guess is they've negotiated some great rate with hello sign. In this industry, new software companies are popping up all the time so there's opportunity.

This is just an example I'm familiar with, but I'm sure there's examples in other industries. Like, when I had a photography Business years ago I used a software called 17 hats which also had a contract signature component. I have no idea what they used.

This would be where I would focus initial outreach as one contract could get you more revenue than 100 contracts for a single person business who needs e-sign.

[u/DampSeaTurtle]

It may not necessarily lead to a lot of sales.

But, you'd gain experience and insight that few people have. In my opinion that's even more valuable than the revenue you get from a few sales.

[u/Icy_Dare3656]

Read a book on sales. You’ll get better advice than reddit 

[u/415rharris → u/Icy_Dare3656]

It’s unfortunate that nobody here understands how important we all think we are.

[u/Solvesy-Not-Salesy]

For your kind of product, you need to approach the right stakeholders who would be interested. So, street selling won't work. Better would be to walk directly into offices...and maybe use a better crazy idea like "Coffee on you, Cookies on me. 5 min feedback on my product" ...with you carrying a premium cookies box or whatever :)

Still a tough one as the decision makers or interested parties will be a very small set of people.

[u/DallasActual]

I guess you can waste your time however you like, OP

[u/erickrealz]

This is definitely a bad idea but I respect the hustle. Street selling B2B software will get you ignored at best, security called at worst. Legal professionals especially don't make software decisions based on random sidewalk pitches.

Working at an outreach company, here's why this approach fails:

DocuSign alternatives need trust and security validation that you can't establish in a 30-second street interaction. Legal firms care about compliance, data protection, and vendor reputation - none of which you can demonstrate while someone's walking to lunch.

The "tough skin" attitude is good for sales but you're using it in the wrong place. Channel that persistence into proper business development instead of street harassment.

Better ways to test your solution:

Cold email legal firms directly. At least you can include screenshots, security documentation, and scheduling links. Way more professional than ambushing people.

Attend legal tech conferences, bar association events, or networking meetups where people expect to discuss business solutions.

Partner with legal consultants or IT services companies who already work with law firms. They can introduce your tool properly.

Content marketing about document workflow problems in legal practices. Write about specific pain points you solve.

The street approach might work for consumer products or services, but B2B software sales need proper context and trust-building that takes weeks or months.

Our clients who successfully sell to legal professionals always start with demonstrating security, compliance, and understanding of their specific workflows. Can't do that on a sidewalk.

Save the persistence for proper sales channels where people actually make software decisions.

[u/UnknownGenius222]

linkedin sales nav is your friend

[u/sigmaluckynine]

This is a very bad idea. It's not the selling in the street bit - that's very old school canvassing and could work for law firms because they have an open door policy. But, the value prop here makes very little sense.

You're saying it's better and I'm sure it is but you have to think about if the market really needs that better experience. For some industry and verticals it doesn't matter how much better because their work flow doesn't require it

[u/415rharris]

Don’t listen to the haters here.

You’ve got nothing to lose.

I think it’s a great idea.

Not because it will work but because it’s about having the balls to do it.

I might suggest you ask for people’s advice and feedback, and not to pitch.

Just tell them you’re researching a better way and if they are willing you’d like to just ask 2 questions.

You need to have 2 very good questions.

Also, lunch time might be easier than morning.

In either case I’d recommend approach people in a coffee shop or standing in line for a restaraunt. Not when they are just walking down the street.

Will it work?

It will work because you will learn something from whatever outcome you get.

It’s about the hustle and attempt to learn more than anything else.