The good news: we shipped a real solution, got our first paying customer, and even sent out our first invoice! The bad news: getting our second and third customers has been way harder than we expected.
We're running into what feels like a canal-product fit issue — our product works, and solves real pain, but the people we’re targeting don't check emails, barely pick up their phones, and often aren’t even on LinkedIn. It’s like trying to sell software to 1997.
We’re hustling hard — cold calling, showing up at trade shows, chasing introductions — but it's slow and uncertain.
If you've navigated early traction in a legacy industry, how did you break through the wall after the first win? Would love to hear any advice, strategies, or similar war stories.
Thanks in advance
Of course, they'll want their own slice of the pie, but that's the nature of the business you've gotten into.
You have one customer... assuming that they are happy with your offerings, perhaps you can get them to be your advocate? Offer them a great deal in exchange for being able to use their name in marketing materials, to get them to write up an article about your product in a trade journal, to talk you up at trade shows, etc.
Trade magazines & physical mailers (seriously). Decision-makers in these industries often ignore digital noise but read industry pubs. A well-placed ad or "How Similar Company Cut Costs by 30%" case study can land meetings.
Embed yourself in their language. One client doubled replies by swapping "AI agent" with "24/7 digital foreman" in outreach terms that resonate with their mental models.
Leverage your first customer. Film a 90-second testimonial (phone video is fine) of them saying "I was skeptical, but…"use it as your #1 outreach asset.
If you’d like, I’d be happy to audit your messaging for free. I’ve helped other hardware/AI hybrids reframe their pitch to cut through the skepticism (e.g., one company replaced their ‘dashboard’ with a ‘command center’ and saw a 40% bump in demos). No strings just hate seeing solid tech get stuck in positioning purgatory!
- carry out some deep market research and analysis, work out the best niches, garner insights into buyer behavior
- content marketing still works but if you use AI effectively becomes extremely efficient and powerful. For example, you could build an MCP server that gives you superpowers with keyword research and SERP analysis tools. There's a growing body of knowledge in this area, sometimes called vibe marketing
Hold in there. Sales cycles are long. Figure out conferences where people go to. Go there. Drop into offices and ask for their time. Find out people who know people.
My rule of thumb is a problem presents its own solution. But I’m not sure how it applies to you without knowing more about your product.
Microsoft didn't stop with basic.
Diversify.
There is no rulebook.
Good luck.