Summary

How do you get your first customers when you have no sales experience and no reputation?

Target people who have not committed to a competitor yet. Define a tight ideal customer profile, qualify fast on one disqualifying question, use AI to build your prospect list, and call early in the morning when owner-operators are still reachable. Price your offer low enough to remove friction. Every conversation is a rep. Build the pipeline one call at a time.

How do you sell when you have no customers, no reputation, and no sales experience?

Robert Cekay from Nashville, Tennessee, called into Ask Jeb with this exact problem. He spent ten years as a software developer building a CRM specifically for home service businesses—small painting crews, junk removal companies, power washers. He built the product. Now he had to sell it.

You Cannot Win By Trying to Steal Customers From Established Competitors

The first thing I asked Robert was about his competition. Jobber and ServiceTitan are both mature platforms in the home services space. He was trying to figure out how to position against them.

My answer: stop trying to.

“How hard would it be for them to unwind and move all their data to you?”

The honest answer is very hard. Switching costs are real. Data migration is painful. Workflows are embedded. The people already using those platforms are not your prospects. The moment a potential customer tells you they are on Jobber or Titan, disqualify and move on.

Your market has to be people who have not bought from anyone yet. New businesses. Owner-operators still running on spreadsheets and instinct who have not committed to a platform. That is the only place you can win when you are starting from zero.

Twenty years ago, when I started Sales Gravy, I could not walk into a company that was already buying sales training from one of my big competitors and take that deal. There was no way. I had no reputation. I had no track record. I had to start by selling companies that had never worked with a sales training organization at all. Those were the only people who were going to take a bet on me.

Same principle. Same playbook.

Define Your ICP and Qualify on One Question

Once the target is clear, the qualification process gets simple.

Robert’s ideal customer profile: a home services business that is relatively new, has an owner who is actively growing it, and does not currently have a CRM.

One question tells you everything:

“Do you currently use a CRM?”

If the answer is no, they are your prospect. If yes, ask which one. If they name a competitor with significant switching costs, move on. No pitch. No convincing. Just move on.

That kind of discipline at the top of the funnel saves enormous time and keeps your energy focused on people who can actually say yes.

Use AI to Build Your List Fast

Robert had been going to networking events and manually scrolling Facebook. But that takes too much time.

Pull up Google Gemini and ask it to generate a list of every plumber, painter, or junk removal company in your target area, formatted as a table with the owner’s name, phone number, website, and physical address.

It is not a perfect list, but it gets you started fast. From there, you are calling, asking one qualifying question, logging the answers, and building your pipeline.

For Robert, I suggested starting with Nashville, Chattanooga, Knoxville, and Bowling Green. Work in a tight geography. Get known in it. Build a reputation before you expand.

Call Early. These Are Owner-Operators.

If you call a plumber at noon, he is under a house. If you call a painter midday, she is on a ladder.

The window is early morning. Six-thirty to eight-thirty is when they are still at home or driving to the job, and they will answer an unknown number because they think you might be a customer. That is your prospecting window.

Text messaging works better than email for this group. Do not count on them opening an inbox. And if you can show up in person, even better. You are at lunch and you see someone in a uniform or a branded t-shirt? Ask them about their business. How do they dispatch? How do they track jobs? Every conversation is a chance to qualify and connect.

Plan for Multiple Conversations

Entrepreneurs who are just getting started are running on low margins and low bandwidth. They are tired. Their brain is full. Asking them to make a software decision is asking them to add something to an already overloaded plate.

You are not going to close in one call. Plan for multiple conversations. 

Log every contact. Track where every prospect is. The pipeline does not build itself, and if you are not maintaining it, leads fall through the cracks.

Get Some Stakes in the Ground

Robert had one beta tester and one committed early user. That is a starting point, not a foundation.

The strategy: get enough people using the product to generate proof.

Do not give it away free. Free means they will not take it seriously. But price it low enough that the decision is easy. A nominal monthly rate that creates skin in the game without creating financial friction.

When I started Sales Gravy, my first job board customers paid very little. Fifteen years later, some of them were still on those original rates. I never raised them. Those customers were among my most loyal.

The payoff is not the early revenue. The payoff is the testimonials, the social proof, the ability to say: here are fifty businesses that have grown since they started using this. That is what closes the next prospect.

When people are paying a small amount, they will not come after you nearly as hard if something breaks as they would if they were paying a premium price. You are going to hit bugs. You are going to learn things about your product you could not have anticipated. A forgiving early customer base is worth a lot.

This Is a Two-Year Uphill Grind

I am not going to sugarcoat the timeline.

Twenty years ago, I was literally crashing job fairs because I could not afford a booth. I had a software product, no customers, and no reputation. It took me two years to land my first big client. I did it one conversation at a time.

My partner at Zoominfo, Will Fratini, calls it chewing glass. It is hard. It is uncomfortable. It is slow. But every call you make, even the ones that do not close, is a rep. You are learning the market, getting sharper on the pitch, figuring out the real objections.

Ask for referrals on every call. Make it a habit. “Who else should I be talking to?” Write down every name. Follow up on every one.

Show up at the chamber of commerce. Find the home shows and trade events where your buyers are looking for customers. Be in the room.

Once you hit a tipping point, your next problem is going to be capacity. You will be the founder, the salesperson, and the customer service department all at once. That is a good problem. You cannot get there until you build the base.

The Bottom Line

When you are brand new and competing in an established market, you do not win by trying to pull people off platforms they are already embedded in. You win by finding the people who have not committed to anyone yet.

Define the ICP. Qualify hard on one question. Use AI to build your list. Call early. Have multiple conversations. Get stakes in the ground with a compelling introductory offer. Log everything.

Show up every day and make one more call.

Pick up 90 Days to Level Up Your Sales Skills and start putting in the reps today. This hands-on, no-BS roadmap to sales success is perfect for anyone who’s new to sales, stepping into a sales leadership role for the first time, and seasoned salespeople seeking to enhance their selling techniques. Get your copy now!

Frequently Asked Questions