How often should I follow up on Upwork applications, what script or texting principles should I use for high reply rate, and should I offer a call in the first message?
He recommends following up every 24 to 48 hours with anyone who replies on Upwork, freelancer.com, Fiverr, or similar platforms. Following up more frequently makes you seem desperate and hasn't worked for him. His sole goal in every message is to get the person on a call, because a call's bandwidth far exceeds text and lets you convey far more information. He avoids trying to close directly on a call due to high pressure and also avoids hourly follow-ups. Instead, he ends each message by asking for a call: after thanking the person for replying, answering their questions, he proposes a quick 15-minute call, offers specific times (e.g., today or tomorrow), and invites them to share their calendar if those don't work. He then provides a link to his calendar and remains flexible. The idea is that every contact should move the prospect toward a call; if you never get them on a call, they're as good as lost.
He starts by asking whether you're replying within a few minutes; if so, your speed-to-lead is already good. Then he advises acknowledging the reply with a thank-you, answering their questions, and giving them several specific times to jump on a call while also offering to look at their calendar to find a slot that works for them. For example, you might say: Hey Pete, thanks so much for getting back to me. Yeah, sure. Here's the answer to that question... Would love to chat Tuesday at 12:30 p.m. or Wednesday at 4:00 p.m. work for you. I can also do Thursday and Friday at these times. If neither works, please send me over your calendar—I'll be happy to book according to your schedule and make something happen. He adds that, for convenience, you can include a link to your calendar. If the prospect says they can't jump on a call today but thank you, you respond with something like Hey, for sure. Yeah, X, Y, and Z. Awesome. Thank you. If that still doesn't work, you propose another option, such as booking for tomorrow at 8:15 a.m., staying flexible. The core principle is that every single interaction should move the prospect toward a call; if you never get them on a call, they're as good as lost.
Yes, you should pitch them on a sales call immediately. When a prospect replies on Upwork, they often ask follow‑up questions like, “Hey Pete, I liked your video. Can you do this for X amount? Can you do it this way?” If you give them all the information in the reply, there’s no incentive for a call—you’ve already proved everything in writing. A call lets you demonstrate how you differ from the sea of generic Upwork freelancers.
The best approach is to lightly address their questions in your reply, thank them, and then suggest a short 15‑minute call to go over details and provide a scoped price. Offer a few time slots (e.g., next hour, 4 p.m., 6 p.m.) and include a calendar link so they can pick what works for them. This way you keep the conversation moving and avoid endless back‑and‑forth.
I also provide multiple ways for them to get in touch—email, calendar link, and other contact options—so they can choose the method that’s most convenient.
Nick says spending an hour on follow‑ups is normal and part of the game; in his door‑to‑door marketing days, most outreach time was spent on follow‑ups, and they later moved to cold calling and phone sales, with the first two hours of the day spent following up on warm leads. He explains that money is in the follow‑up because even slight interest is hard to get from a cold offer, so you want to squeeze that interest as much as possible. Regarding automating follow‑ups: if they’re templated, you could automate, but he prefers personalizing follow‑ups when possible, especially if the prospect showed personalized interest. He notes that free automation tools exist (like connecting via make.com or using Claude routines) but at scale you’ll need to do more, implying paid solutions are necessary.
When you get a lead from an ad, you've paid for it, so try to recoup that cost. Top operators follow up every couple of hours via SMS and text nonstop. I'd send a text, email, and call within one minute of sign‑up—make sure they see the text if they're on phone, the email, and hear the caller ID as your business name. If they don't pick up, leave a voicemail and say something like, 'Hey, how's it going? I can solve your problem quickly, book you in, and have someone sent out soon.' Then follow up every couple of hours, pushing hard on SMS and email. Remember, ad clicks aren't intent‑based; treat those people like goldfish with short attention spans, unlike my organic content where a relationship already exists. To increase perceived value, be crystal clear about what the meeting will cover—run through your agenda, note the exact length (15‑60 min), and offer something like a $250 Amazon gift card just for their time. Have them fill out the form, contact them immediately, try to hold the meeting right then; if they can't, follow up later. When you book later, lay out exactly what you'll do, with no strings attached, then deliver a customized audit and over $1,000 in value, making it a no‑brainer to say yes.