Should B2B software be self-serve or high-touch at first?

When I set direction for lightbreak's build, I was blunt about it:

"lightbreak is not going to be a self-service platform. This is going to be a high-cost, high-touch platform for the foreseeable future, so do not worry about Stripe or any automated onboarding. Just imagine I would do the onboarding for them, at least for the next 5."

At the time I had one client on it and a goal of 20 to 50.

Why go high-touch first?

• The buyer isn't technical. lightbreak's customer is a legacy local media company running several to 20 newsletters. Most are extremely un-tech-savvy, but a lot of them want to move forward.
• The real risks aren't billing. The questions are whether the systems, forms, events and email sending work in a new town. An AI I was working with added that writing quality and local sources are the real risks.
• The price can climb. My plan was to move lightbreak from $100 a month toward $200 to $300 as it went upmarket.

Going upmarket has a catch. The buyer gets further from the person who does the weekly work, so somebody has to actually run production after the contract is signed.

Who is the customer, if solo writers already have AI?

Solo newsletter writers are mostly served by the AI built into their email platform. There isn't a big enough need there. The target is local media companies, especially legacy ones that now run lots of newsletters, usually on Newspack plus Mailchimp or ActiveCampaign.

My idea for them: an editor says "write a new edition" in Slack and a draft shows up in their inbox to approve, without ever logging into my tool. An AI I was working with summed up the pitch well: sell "your Tuesday draft is already waiting," not the API.

How do I get in front of B2B buyers?

Go to them. Most software competitors try to draw people in and wait. Selling to small businesses and associations is a true sales play, and that's an advantage, because nobody else is doing it:

• Cold call.
• Show up at their conferences. You don't even need a booth. Walk up to the booths and ask if they have a newsletter, then hand over your card.
• Offer around 20% commission for referrals.

Getting demos is often the real bottleneck. Software I built for insurance agents took two years to get really good, and it closed at around 60%, which is crazy for a B2B SaaS app. We just weren't doing many demos, because I couldn't get in front of agents.

"I have an insurance SaaS product. I want to sell the insurance agents. I can't get in front of them. So what's the best way to get in front of them? Build something that they would choose to look at, right?"

My answer was a newsletter for that audience. More in local newsletters for insurance agents.

What about a tiny niche with only a few thousand buyers?

The insurance product was that. We charged $100 to $200 a month, the sales were sticky, and we had 15 clients with a goal of 45 or 50. My thinking was that once we reached 30 or 40, the agents would start sharing it with their buddies and inbound would follow.

Getting those first customers was hard. Here's what failed:

• A cold email tool got a 60% open rate, then went to zero within 36 hours. I'm pretty sure the agents' corporate email system flagged and blocked us.
• I paid $800 for a list, but it was all work emails.
• About two weeks of Meta ads brought six leads, and I don't think a single one was an agent.

Should B2B software show its pricing?

It depends on who you're selling to. For $50 to $100 software aimed at random entrepreneurs, put the price up and let them buy. If you're going after bigger organizations, a listed $100 price can make them lose interest.

It also sets a trap. Someone on a call wants the news API, the events and more, and that's actually $400 a month, but they saw $100 on the page. I personally don't like sites with no pricing. The question is whether I'm the ideal client, and I'm not. For bigger deals, the call is where you scope the real price.

When is self-serve worth building?

After the managed version works. I prefer selling a capability as a managed service first and productizing once the interface is solid. When greetform got self-serve plans, the requirements were concrete:

• Google sign-in, no Apple sign-in
• A "prove you're human" check
• A Help button with a message form that takes up to five photos and routes to a shared support inbox
• A polished enterprise inquiry form asking about number of publications, employees, revenue and goals
• Never save or show an empty question in the editor

What's the path from one client to investment?

My stated path for lightbreak: nail the pilot, generate referrals, reach $4,000 to $5,000 in monthly recurring revenue, then approach an AI-native technical partner or a local-media angel for a 10-15% equity stake rather than a straight investor. See lightbreak for what it does today.