If that's your target, then you might possibly be operating under at least a few wrong assumptions.

As they say, you always want to sell to stakeholders. In large orgs, most people you can talk to just earn a salary. If you're selling time, money, or savings for the org, they're rarely interested. What usually holds their attention are magicians that offer to make their problems disappear.

You're trying to sell a DIY kit to companies where, past a certain size, the type of competency required becomes a rare commodity in-house (regardless of how ridiculously simple the solution). So they typically avoid upgrading themselves into new problems. Integrating a SaaS is always a new problem.

In addition to selling the tools to solve their problems, can you also offer to sell the service that makes them go away? Can you be the magician that makes entire problems disappear? What if you told them you'll take them away for a fee, could that get their attention? Try it and see if it at least gets the conversation going. If it does, you can lay out a price table where you charge a premium to hire a few people to work on it with your own tools.

You can monitor socials for individuals complaining about the pain point or about a competitor and reach out when you got a proper "signal".

I also avoid saying things like "free trial". Instead, I offer to give them access to the paid product to try it out.

It sounds less car salesman-y and as a receiver it feels nicer to get access to a paid product rather than a free trial everyone can have. Semantics most of the time, but it helps.

You can write organic content about how to solve those pains (and hope people searching for solutions find it).

When you do get customers you should always include a form that asks _why_ they are unsubscribing. I have learned a lot from it and it also offers a chance to turn customers back around. If someone complains about the price, I can give them a discounted rate. If someone complains about a specific quality issue I can give them free credits to make up for used ones, etc.

Always respond quickly. I have landed many customers simply because I respond quickly to emails. I've had customers tell me they chose my service over "big competitor Y" because I respond to their emails (even though my service is more expensive).

If you have an entire vertical, don't undervalue the small fish. I target ~3 different types of customers and the bulk of my revenue comes from one specific type of customer. I almost got rid of the other two customers, but realized my largest customer ($1XX,XXX/year) started off as a small fish for a year before becoming a big fish.

That may go against some of the traditional advice, as the small fish tend to account for most of the support... but in my case it works out.

A lot of the small customers end up being a channel on their own. A person leaves company A and goes to company B. They introduce your product at company B because they used it at company A.

When I speak with people I always ask how they found out about my product. Nine times out of ten it's a "coworker used your product at a different company".

In my case, I built an app called foundersmail.xyz, which gives users access to founders' official emails and other details. I got the idea after seeing someone else build a similar tool for investors — it worked well for him, but he already had an audience and reputation.

For me, I promoted it across various subreddits and platforms and got around 100 users. I noticed that only 20–30% actually used up their free credits. While debugging this, I discovered most of my users were students cold-emailing founders for summer internships. I thought at least one of them might convert — but unfortunately, none did (still trying to figure that part out).

My two biggest mistakes:

No traffic — not enough eyeballs.

Target audience mismatch — students using it instead of founders or professionals.

Interestingly, there are competitors making money with similar products, so I know there’s potential. I’m still figuring out what’s missing in my approach.

That said, I’m okay with the outcome so far. I haven’t spent a single rupee — free domain, free hosting, and I built it in my spare time and vibe coded. It was an experiment rather than an actual business.

Marketing became much more important than it used to be. I used to be able to rely on organic growth from people finding my SaaS using search engines. But this ended several years ago. Marketing also became much more difficult than it used to be. Generic ads on Google or LinkedIn no longer work, unless you can spend huge amounts of money on testing. I found all paid ads to be a waste of money.

If you have a B2B SaaS, you run into the additional problem of people being busy and not hanging out in forums. With consumers, things are more straightforward. You can generally blast an ad on Reddit, Instagram, and some other sites, and people will see it. Not so with B2B. Many of your customers will be busy working, and they will not pay any attention to work-related ads outside of work.

Content marketing also became more difficult. With search engines, especially Google, going down the drain and the deluge of crappy SEO-gaming and AI-generated content, it's difficult to rise above the noise.

I haven't found the right solution yet.

e.g. if your potential customers are perfectly happy to use spreadsheets to manage their workflows at your price point, it's not going to work out.

Trying not to be an ass, but "Build it and they will come" is not a good strategy (that unfortunately I've done/experienced multiple times).

People only care about "more value" when it solves more problems. So if your competition is killing it, and you are not getting bites on your added value, you need to talk to people to find out what pains they still have even when using your competitor's solution, and then make sure your added value resolves those pains.

Otherwise, you've got the same solution, just a shinier version, and that is all your 1:1 feature comparison will show.

There is a big caveat on this that we have no idea what product or feature set you are talking about, so this is pure speculation. You'd have to share a lot more about your product and marketing to get more substantive answers.

I understand (and in certain context appreciate) hesitancy to blatant self-promotion but this is not the time.

Not seeing your website, websites of who you think your competitors are, links to your promotional efforts etc. makes it impossible to give good advice. The best you can hope for is generic, vague advice.

The devil is in details.

Maybe your website is bad. Maybe your product isn't as great as you think. Maybe your pitch is not good.

Generically I would say most people don't do enough promotion and could improve their "first time use" (onboarding) experience.

For example I make a note-taking application for developers and power users: https://edna.arslexis.io/

Almost all of my users came from Show HN post https://news.ycombinator.com/item?id=40846242

So it's a sobering realization that I got lucky enough that the post was interesting and generated discussion and made people try the app.

At the same time, I know I could be doing more marketing.

I know I could improve onboarding, I could record videos showing how to use more advanced features etc.

Chances are you could do more marketing and you could improve onboarding in your app but to give you specific, actionable advice we would have to know much more about your app, your competitors, your marketing efforts.

Not your description of those things, the actual website, the actual marketing post etc.

Top down means you’re trying to sell managers and above who don’t directly use the tool. Usually they care about seeing case studies, logos of other companies, testimonials from their peers, etc. They want to look good and the way you help them with that is making one of their metrics look good, or giving them more budget to work with. Safe decisions are easier for them to make because they don’t want to get fired by making a risky bet, even if the risky bet offers more for less (“nobody ever got fired for choosing IBM”). Usually the way in with them is through partnerships, relationships, and education. Start with friends who work in that industry to get you a case study and logo or you could try to make friends at a conference if you don’t have any already. Or create some educational material around the problem and sell them consulting, using your tool as a solution. Almost always this starts off as more consultative as a relationship.

If it’s bottom up, you’re selling to the individual contributors who don’t get a say about paying for the tool. That means you have to start with a generous free tier and try to get as many seats filled or usage as possible. It should bring enough value to the ICs and the organization that by the time they hit their usage caps in the free tier, the ICs are begging their managers to put a credit card in or asking to set up a sales call. If you’re not getting any usage at the free tier, then it comes back to finding where the ICs hang out and trying to integrate your tool as part of a workflow to common problems they solve. This is again about educating and making/leaning on friends to help spread the word and convince others to use your tool.

In both cases, relationships matter a lot to get initial traction (existing customers, friends in the industry, partners). They will help you figure out what’s needed to sell into the market you want to sell into, what’s holding you back, and getting you early validation. I didn’t see you mention existing relationships you have, so maybe that’s a good place to start.

With me preaching textbook digital marketing to my team, I feel dirty and like a fraud.