Hi everyone! In this newsletter, I want to focus on how to strengthen your communication with clients, including golden cover letter rules and keeping conversations going with your leads.

P.S.: Back in time, we had a great webinar about cover letters on Upwork, which you can check out here.

Here are the golden rules of communication with leads who could become your clients, based on what I’ve learned from working with hundreds of agencies on Upwork.

🏁 Start Strong

Remember, the client only sees the first sentence of your cover letter when scrolling through incoming proposals.

Don’t waste this crucial space on unnecessary intros or information that’s already on your profile.

Start with something personal and directly address the client’s pain points.

🃏 Avoid Exposing All Your Cards

Starting with “We have the perfect developer for you” is a mistake.

This phrase usually means you’re referring to your agency, and it often involves attaching a faceless CV of some random guy, while the client is evaluating the profile you’re using to apply.

Remember, Upwork is a platform where trust and feedback are everything, so proposals like these are likely to be ignored.

First of all, you need to win a reply. Then you can dictate your own rules.

🗣 Avoid Loud Titles

Don’t start or structure your cover letter around your position, like CEO or founder.

Here we have a combo!

Clients want to hire the person behind the Upwork profile, not someone with a title that makes them think of extra costs or complexity.

Save the title for the call—first, focus on getting the client to that call.

Similarly, don’t start with lines like “I am a senior front-end developer” if it’s already clear from your profile.

📣 Avoid Overusing Fancy Text

Using too many emojis and bold Unicode text can make your cover letter seem immature or unprofessional.

Imagine your lead is an experienced businessman from Scandinavia looking for a team to build a complex freight software solution. They’re not going to be impressed with “₊✩‧₊˚౨ৎ˚₊✩‧₊🎬 ,🍿 𝒉𝙚𝒍𝙡𝒐 𝒅𝙖𝒓𝙡𝒊𝙣𝒈.”

Keep it clean and professional.

🧘 Personalize

Ask Sardor AI to find an interesting detail in the job posting to use as a hook. If you're applying manually, try to locate the client's name in the feedback section. But never use “Dear hiring manager.”

Here’s why:

a) It’s an outdated phrase, often generated by AI like ChatGPT 3.5, making it obvious that your cover letter wasn’t written personally.

b) It could offend a founder, especially if they’re running a small company and don’t see themselves as just a “hiring manager.” For instance, a founder of a freight company in Norway might find it off-putting to be addressed this way.

🧪 Experiment

Our Sardor AI is trained on thousands of cover letters, so it can write them in various styles. However, remember that using generic templates will likely result in generic outcomes.

Here’s a tip: you can fine-tune your cover letters by tweaking the prompts you give to Sardor AI. For example, add a prompt like:

[Based on the job posting, extract and ask a thoughtful question regarding the most emphasized pain point related to React Native development]

Remember, Sardor AI is familiar with who you are, so you can set it to use information directly from your profile!

Check out our help center for more prompts to make the most of Sardor AI.

🤏 Keep It Short

A short cover letter is easier to read and doesn’t tire the client.

Remember, your application is one of hundreds they’re reviewing. Don’t overwhelm them—get straight to the point and address their pain points directly.

✍ Grammar matters

Correct grammar is crucial. With so many tools available that automatically correct your writing—even on your phone—there’s no excuse.

Have you heard of the Broken Windows Theory? It applies to your lead generation too—small details make a big impact.

📩 Invitations = Bids

When responding to invitations, approach them with the same effort and attention as you would a proposal you initiated.

Don't respond only with: "Yes, i am ready". 

To win that contract, you still need to put in the effort.

🤗 Leave a Good Impression

Never leave your leads without a proper reply or farewell, even if they seem irrelevant.

You never know if, in a couple of months, they might require your expertise. If you left a good impression, it’s more likely they’ll return (after nice-built follow-ups, of course!)

🔄 Follow Up x3

Always follow up with your leads:

• Don’t worry about being too pushy.
• The third follow-up message can be the best icebreaker.
• On Upwork, each message brings your conversation to the top of your lead’s inbox.
• Set tasks in your CRM to follow up with leads three times during the first contact and another three times over the next three months.

💡 Follow Up x3 Wisely

Don’t just write “Hello” or “What do you think?”.

• Check the job posting again, find a new pain point, and address it in your follow-up message.
• Ask a relevant question. Look to see if the lead has posted other jobs and mention it too.
• Show you’re interested—it doesn’t take much effort but can make a big difference.

🎯 Be Concise

When responding to leads, avoid overwhelming them with too much information.

For example, if you’re sharing an estimation with your rate and hours, don’t just write "12.5 * $40." Clearly state that the total cost will be $500.

🌪️ Healthy Upwork Pipeline: Business Development 

• Niche: Sales <> Appointment Setting | Business Development
• Upwork Agency: Top Rated
• Lead Generation Budget: $~1.5k (It's an example, where agency owner closes leads)

Here we have a very interesting niche: sales and business development. This includes services like:

• Appointment setting
• Lead generation (email and LinkedIn outreach)
• Cold calling
• Closing

As you can see from the LRR, this niche has always performed well on Upwork due to less competition.

And, let’s face it, if you’re selling sales, you likely know how to get the job done, which typically results in higher conversion rates.

weekly stats

A quick note: cold calling is much more popular in North America, whereas in Europe, GDPR has made it less effective. So, if you’re a US-only agency, a cold calling offer might boost your LRR by 30-40%.

You might notice that one stage is missing on the graph. Why?

Most B2B BizDev agencies offer packages with predefined pricing, which is usually discussed during the conversation or checked on the Upwork profile. This often leads directly to a call with a proper estimation.

As for the final stage, keep in mind that the sales cycle in this niche is short, especially compared to something like web development.

This means you need to close deals quickly or set a “follow-up in 1 month” task in your CRM.

Are there any business development agencies here? What are your stats?

P.S. I remember one client who showed around 45% LRR for cold calling and appointment setting services—but that was from a US-only freelancer profile.

In our #education channel, members share valuable insights at every growth stage. Here’s a recent post that aligns with the vision behind GigRadar.

As I built GigRadar, matching the right leadership to each growth stage was crucial. This community post reflects that approach.

Key Takeaways

1. Early Stage ($0-$2M ARR): Avoid hiring an “Evangelist” too soon. Focus on using your founding team or early reps to drive growth.
2. Growth Stage ($1M-$10M ARR): Now, you need someone who can scale your wins into a repeatable process. Look for a leader with proven experience at this stage.
3. Scaling Stage ($10M-$20M+ ARR): Hire someone who excels in standardizing operations and taking your agency upmarket.

And remember, we’re always waiting for you in Our GigRadar Community!

We created this Community to bring everyone together for collaboration, sharing expertise, and tackling challenges as a team. 💼 Here we discuss everything related to Upwork, GigRadar, and Business

Join Community!