How to Message a SaaS Seller: What to Ask Before Discussing Price

The first message to a SaaS seller matters more than I expected. Not because it needs to be brilliant. It just needs to prove that you are a real buyer and not another random person sending, “Is this still available?” like the business is a used couch on Facebook Marketplace. When I first started talking to sellers, I thought I needed to sound extremely professional. I wanted every message to show that I understood revenue, churn, valuation, technical risk, customer concentration, and probably international monetary policy too. That instinct was wrong. Most sellers do not want a giant essay from a stranger on the internet. They want to know three things:

A short, thoughtful message usually works better than trying to sound like a private equity firm with $11 in assets under management.

A strong first message does not need to cover the entire diligence process. Its job is to start the conversation. That means showing genuine interest, referencing something specific about the business, and asking for a few key details. For example, when I reviewed an established storyboard software company, I did not immediately send the seller a 37-question diligence spreadsheet. I first tried to understand the basics:

Those questions gave me enough information to decide whether the deal deserved more attention. That is the goal of the first exchange. You are not trying to complete diligence in one message. You are trying to earn the next conversation.

A message like this works because it is short and specific: “Hi, I’m interested in X, and the details are a strong fit for what I’m looking for. Before discussing an offer, could you share the monthly revenue and MRR history for the last 24 months? I’d also like to understand the tech stack, support workload, and whether there are any known technical issues or dependencies.” That is serious enough to show intent without making the seller feel like they just received a 20-page thesis.

It is tempting to jump straight into valuation. You see a business listed at $30,000, decide it is worth $17,842 after eleven minutes of research, and want to announce your findings immediately. Usually, that is too early. Price makes more sense after you understand what you are actually buying. A business may look expensive based on the listing headline but become reasonable once you see stable retention, low expenses, and minimal owner involvement. The opposite also happens. A business may look cheap until you discover that:

That is why I prefer asking about revenue history, customers, churn, expenses, and workload before making an offer. In one AI development tool evaluation, the seller explained that the business had strong organic traffic and high margins, but also high churn and meaningful technical risk. That information mattered far more than the asking price by itself. Once I understood those details, I could think about valuation more clearly. Without them, any offer would have been based on a headline and a feeling. Feelings are useful for relationships and choosing pizza toppings. They are less useful for acquisitions.

Marketplace listings often show a few major figures:

Those numbers are helpful, but they are only the beginning. You want to know how the numbers were created. For revenue, ask for monthly history rather than one annual total. A business that earned $12,000 evenly across the year is different from one that earned $9,000 in January and slowly limped through the next eleven months.

You may not ask for all of this in the first message, but these are the questions the conversation should eventually answer:

A Stripe screenshot is useful. It is better than receiving a number typed into a message with no evidence. But a screenshot does not tell you everything. I ran into this while evaluating a payments-related SaaS add-on. The seller shared dashboard figures, but the number of plan subscriptions did not seem to match the number of active subscribers. One report showed 185 plans. Stripe showed 127 active subscribers. That difference needed an explanation.

There were reasonable possibilities. A customer could have multiple plans. Some accounts could be canceled, delinquent, paused, on free trials, or using full discounts. But the screenshot alone did not explain which answer was correct. That is the problem with dashboard screenshots. They show a result without always showing the machinery behind it. A screenshot may not reveal:

Use screenshots as a starting point, not a finish line. Later in diligence, you may want exports, monthly reports, invoices, or read-only access. You do not need to demand admin access in your first message like you are executing a search warrant. Trust and access should increase as the deal becomes more serious.

Good seller conversations are usually gradual. You ask a few questions. The seller answers. You review the answers and ask the next logical questions. This works better than dropping 25 questions at once. A long diligence list may be necessary later, but early in the process it creates friction. The seller may delay responding, answer only half the questions, or ignore the message completely.

It is easier to ask in stages:

Each step should help you decide whether the next step is worth taking. That is important because not every deal deserves full diligence. Sometimes one answer is enough to move on. That is not failure. That is efficient buying.

One of the biggest lessons I learned is that seller conversations become easier when you stop trying to impress the seller. Your job is not to prove that you know every SaaS term. Your job is to understand the business. That means asking simple questions when something does not make sense:

Simple questions often expose the most important risks. A buyer who asks clear questions will usually learn more than one who hides behind complicated language. You are allowed to say, “I may be misunderstanding this, but could you explain the difference between these two numbers?” That does not make you look inexperienced. Pretending the numbers make sense when they do not is much worse.

Seller conversations can feel intimidating at first. You may worry about saying the wrong thing, asking a basic question, or sounding too inexperienced. But the goal is not to perform. You are not auditioning for Shark Tank. You are trying to understand whether the business is worth buying.

A good seller conversation should help you answer:

You do not need to answer everything in one message. You only need to keep moving toward a clearer picture. The first message matters because it sets the tone. Keep it short. Show that you paid attention. Ask for the numbers that matter. Do not negotiate against yourself before you understand the business. And remember: you are not trying to sound like a private equity firm. You are trying to avoid buying a stressful job with a Stripe dashboard.