Long Sales Cycles: Managing the Periods between Lead Gen and Conversion

A few weeks ago, I was watching a video from James O’Sullivan (current Apollo Academy Professor and former Senior Manager at Uber), where he detailed the story behind one of his biggest deals (an 8-figure deal he pulled in from a delivery company).

In this video, James explained how he carefully curated a list of leads and contacted them separately via email. In one of his sales cycles, he sent out an email message to one of his leads, the founder of a big delivery company… and didn’t get a response. 5 emails later and still no response from this founder. At this point, most people would have wrapped it up and gone… “Well, he doesn’t need my services yet, besides, this sales cycle is getting too long, let’s just call it a day”.

But not James. Sending the 7th email, the founder responded with a short message, referring James to another member of his company who was better suited to handle the rest of the conversation, and the rest is history.

I know sending 7 emails can seem like a lot (even for experienced salespeople and prospectors), but one thing I picked from James’ experience is the fact that sales cycles sometimes take forever to convert.

And as freelancers and artisans, it is no different. I am sure you’ve spoken with clients who told you they’d message you soon… and you did not hear a pip from them for months, only for them to appear later and tell you they want to work with you… 4 months after your first contact.

Sounds familiar, right? That’s one side of the service business we all have to learn to deal with and in this piece, we share important tips that can help you navigate the extended periods between lead gen and conversion.

1. Master the art of the follow-up: You may not be a master salesman, but mastering the art of the follow-up is crucial if you want to keep your offer front and center in the period between the first engagement and conversion. To do this right, send timely (so your leads don’t feel overwhelmed) reminders about the details of your earlier conversation, offering any help you can in the interim, and reminding your prospects of your offers.
2. Put out educational content when you can: While long sales cycles are typically a result of complex decision-making processes, there are times when your leads don’t yet understand the value of your offer. One way to get them to see this value is by putting out educational content that provides the important information they need to make the right decision… and make it quicker!
3. Study your sales process carefully and identify what parts lengthen the process: All sales processes differ, some are typically shorter (say a lead wants to buy a simple item like a watch or a pair of shoes) and some longer (for example a company that wants to get a software to use in its day-to-day processes needs to ensure other parts of their business/workforce will be able to adapt to this new tech and ensure compliance across board). Knowing your sales process inside out and identifying the areas that are problematic can help you shorten the sales cycle. Once you identify these areas, you can develop walkarounds to help you navigate the hurdles associated with it and move faster.
4. Be patient: Sales cycles can be long and sometimes, it gets too easy to become discouraged (especially as a freelancer or one-man business) speaking with multiple leads. But spacing out your sales and follow-up process, while consistently sticking to your schedule and system can help you ride the wave, and come out on the other side of the cycle victorious.

So when next you reach out to a lead (and get a response) and the conversation seems to be taking too long to lead to a conversion, remember that sales cycles can be long and you can apply any of the tips above–depending on your niche and the uniqueness of your sales process– to keep your boat afloat in the period between generation and conversion.