5 Ways to Shorten Your Deal Cycle When Selling to Entrepreneurs & Solo Business Owners


When it comes to selling, the audience will always have a connection to which types of solutions you implement and what resources you can use to effectively close deals. If your primary audience is the entrepreneurial market, it’s a whole different approach for you than for those selling to enterprise organizations and major international corporations. By taking the time to learn the best way to approach your cold leads based on business size, you’ll be able to tailor a campaign that makes everyone feel like you’ve reached out to them personally. Or you can always outsource to a sales outreach team to assist with the work.

The tips below are designed to help you find little ways to shorten your deal cycles when dealing with solo business owners and entrepreneurs. Some of the methods may be similar to selling to SMBs and even enterprise organizations, but some will be much more relevant to the one-on-one connection that you’re creating here. 

There are dozens upon dozens of tips and strategies out there that you can find to help you improve your sales efforts. Depending on what business you’re in and who you’re dealing with, the best answers might be a bit different. When you want to step up your game and improve your sales cycles, you have to take the time to understand your audience. In the solopreneur world, here’s what matters. 

1. Create a connection and build a relationship

You might be able to be a little more formal when you call an enterprise organization, but if you are working with a solopreneur, you have to go straight for the personal connection right away. That doesn’t mean to stop being professional—it just means that you need to know your call list and anticipate their needs in a way that you can create instant connectivity and give them that human touch. This will be the beginning of a great relationship and can get you deals a lot quicker because you develop a relationship built on trust

2. Know exactly who you’re talking to

In any sales encounter, you should try to identify the key decision-maker by name so that you can reach them effectively. This isn’t a situation where you can ask to speak to “the person who handles purchasing,” for example, because that proves you have no idea who you’re calling and gives the person on the other end no incentive to stick around and find out. 

Thanks to LinkedIn and other sites, there’s almost no way that you can actually say you can’t figure out the name of the person you need to reach. Even if you can only get their first or last name, you can find a way to greet them that acknowledges that you knew their name at all. If you don’t know their name, set them aside until you do. We promise it will shorten (and sweeten) the deal cycle. 

3. Eliminate your cold leads (and use them to your advantage)

The quicker you can get rid of cold leads, the better you can reach the warm ones that could become lifelong customers. And if you want to kick things up, consider making as many calls as you can without worrying about whether people are interested. When you call, just casually explain you’re cleaning up your leads list and want to “make sure they’re not interested and cross you off the list so they can make room for prospects that are interested.” Not only does this explain your call, but it offers a tinge of fear of loss for people who might be curious and want to know more. 

4. Make your mission clear and your call brief 

You’re an interruption in the business day—the entrepreneur is busy and doesn’t have time for interruptions that aren’t worthwhile. Make sure that you start out with transparency and a direct admission that you know they’re short on time, and that you’ll only take a moment of it. 

When you provide a clear mission and show through your words and your tone that you’re trying to help them, but not take too much time, you’ll have a much better chance of impressing them and shortening the cycle of the deal. This also increases their likelihood of becoming a long-term client or customer because of the respect offered right upfront. 

5. Have answers ready 

There are going to be objections. People will have questions. Many entrepreneurs are sharks and will be ready to tear your sales call apart, even when you think it’s perfect. Make sure that you study up and have answers ready and waiting for people. Consider the most probable objections, what questions or concerns people might have, and other factors that could require you to deliver a quick answer or rebuttal on the spot. 

If you take the time to plan, you can always have the next move prepared. Sometimes, sales deals are like a chess game. Not only do you have to know your moves, but you have to be able to anticipate the moves of your “opponent” – in this case, your audience. When you have to “get back to them” or stumble through answers, it takes longer and is more likely to scare leads away. 

And if you need assistance, enlist the help of the virtual receptionists at Smith.ai 

When it comes to making deals, you can’t overlook the details. The good news is that you don’t have to do it alone. Whether you want someone to help with all the new scheduling and lead intake, or even earlier in the sales cycle, our 24/7 virtual receptionists can deliver everything that you need. In addition to handling admin and communications, we can also assist with outreach campaigns, outbound sales and support, and more. 

To learn more, schedule a consultation to find out what the 24/7 virtual receptionists can do for your sales deals and so much more. You’ll also reach us at hello@smith.ai or (650) 727-6484. 

Business Education
Solo Business
Sales Tips
Written by Samir Sampat

Samir Sampat is a Marketing Manager with Smith.ai. He has experience working with businesses of all sizes focusing on marketing, communications, and business development.

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