My Freelancing Workflow, from Cold Leads to Paid Invoices

My Freelancing Workflow, from Cold Leads to Paid Invoices

How I successfully pitched my services and closed deals when I was getting started as a freelance web developer.

In January 2021, I made a sudden transition to freelance web development. I wasn't sure if I was ready to seek work as a developer, but the universe said:

"It's now or never."

After reviewing over 500 websites in my vertical, I selected 100 businesses to cold-email with a pitch offering my services.

Eight got back to me: five were retired, three were interested. I walked away from one of those interested after receiving a low-ball offer, and the other two requested proposals outlining the scope of work and my rates.

This was the point where I realized,

"Oh snap! I have a real business here. Now I actually have to figure out the logistics of seeing these projects through!"

Google wasn't much help on this topic - content in this genre tends to be heavy on fluff and light on actionable advice.

So I forged my own path based on what I could find and what I know from previous business endeavors and work experience. It ain't perfect but it's good enough to get started.

Please keep in mind that I am anything but an expert! And nothing here constitutes legal or business advice.

My results here are definitely not statistically significant, and I look forward to gaining more experience so that I might be able to share more accurate numbers in the future in terms of what others might expect. I just want to help mellow out the learning curve so other people can get up and running quickly.

Some of the services I will recommend are not free. I wish I had free alternatives, but often the "alternative" is just to invest countless hours of tedious labor into something that would otherwise cost $10-20 to automate in an instant.

That said, as someone who's been self-employed in other industries, I can say that web development requires exceptionally low startup costs relative to the return on your investment. If you are willing to part with $50-100 in your first month, you'll be fully equipped to efficiently land deals worth thousands of bucks.

My freelancing pal Nat Miletic pointed this out, and I really believe it has been crucial to my early wins:

I have been very intentional about who I am targeting and what's unique about what I offer.

Pick a Vertical

Your vertical market is the clientele that you will target who all serve similar clients themselves; think gyms, restaurants, plumbers, barber shops.

You need to "niche down," to borrow from online marketing terminology, and specialize in serving a specific market.

I worked in skilled trades for the last five years, so I speak the language of that industry. I know how to describe things like exterior hardscapes, kitchen renovations, and hardwood flooring. When I decided to start freelancing in web dev, I knew right away that my target clients would be residential contractors in my region.

Picking a vertical might not be as simple for you as it was for me. Things to consider:

  • What can you offer to business owners in this field that is unique? (Being able to speak competently about their industry is a huge plus - one of my landscaper clients really appreciates that I am also an avid gardener.)

  • What are the profit margins in this industry? Does anyone have a budget for your services?

  • What are businesses in this field using their websites for? If they just need an "online business card," your job as a developer will be much simpler than if they need some kind of database or e-commerce functionality.

  • What are the demographics of the clientele your prospects are serving? High-end businesses will have bigger budgets for branding and marketing expenses, but smaller and newer businesses might have a greater need to generate new leads for themselves through their online presence.

  • What services can you upsell your clients on? After all, if you're planning to build a business's website from start to finish, you're not just a developer. You're also taking on the roles of:

    • designer

    • copywriter & editor

    • SEO strategist

    • content & multimedia manager

    • publisher & technical support

...and you should be charging for each of these services in your proposals, commensurate with your experience! More on proposals as we dig deeper.

Generate Leads

I use d7leadfinder to generate lists of businesses in my vertical from the cities in my region.

It costs $25/month and can potentially give you more prospects in a single day than you would be able to handle in a year.

You select a keyword (choosing from a predefined list) like "Plumbing", "Hair Salons", etc. and a city. It will work its magic scraping the internet for a few minutes, then spit out a spreadsheet with contact info for all of the relevant businesses that match your query.

Your mileage may vary, but when I search "Landscaping" in "Santa Cruz, CA" for example, I get about 100 relevant listings.

Here's where you're gonna invest a lot of time, and I don't know a good way around it:

You have to go through this list and look at every. single. website.





It's going to take a long time.

Put something on in the background that will keep you in a good mood. I like old Simpsons reruns.

After I reviewed about 500 websites of businesses from 3 or 4 cities in my region, I was able to narrow my spreadsheets down to roughly 100 prospects.

What was my criteria?

  • First and foremost: is the existing site mobile-responsive? With half of all web traffic now happening online, a smartphone-friendly website is a must for all businesses.

  • Is it broken or difficult to use in some way? Is it inaccessible or crazy-slow due to technical issues, poor design choices, or outdated practices?

  • Is it on a WYSIWYG platform ("what you see is what you get" i.e. Wix, Weebly, Squarespace, GoDaddy)? Small biz owners sometimes think they can save money by going DIY with their site, only to discover that it's actually a much bigger undertaking than they anticipated.

Once I had 100 prospects that I identified as genuinely in need of a new website, I moved them all to a new spreadsheet and started getting my marketing materials ready.

Craft a Pitch

The best clients will be the ones who already know that they need your services. You don't need to convince them of the value of your work, and you will be solving a big problem for them by reaching out with your services.

That's how you need to approach the cold sales process: as though every single person you're contacting genuinely needs what you're offering, and perceives it as valuable. This is a big part of the mindset you need in order to communicate with confidence through the sales process.

I'll share my first email template with you, but first I want to say that, after doing some research on the topic, I realize that this email is pretty bad. Go ahead and read it, and then I'll explain:

Hi (person),

I recently came across your website and was curious if you would be interested in help with your web presence.

As a landscaper in Santa Cruz myself — I’ve been in the industry for several years now — I know how to reach the kinds of clientele you serve, and how to build websites that bring in more leads.

If you’ve been thinking about upgrading your site, I can offer a sleek, stylish, lightning-fast design that’s mobile-responsive and indexed properly for Google and other search engines to improve your rankings.

Over 50% of all web traffic happens on smartphones these days, and if your website is not optimized for small screens then you’re losing out on the majority of visitors.

You can see a sample of the kinds of sites I build here: (link to demo site)

And if you want to learn more you can check out my portfolio: (link to my portfolio)

If you’re interested, let’s schedule a time to chat about this. I look forward to hearing from you!

Sam Sycamore

// web developer & designer


  • First of all, it's way too long!

Who would want to read this? Good golly, man. What were you thinking?

  • Second, as Nat once again so astutely points out, I'm not "a landscaper who moonlights in web development as a side hustle." I'm "a web expert who specializes in online marketing for contractors and small business owners."

See the difference?

One says "I'm just some guy who's doing this for fun in his free time."

The other says "I'm the best choice for you because I'm a professional who knows how to solve your business's specific problems."

Who would you rather hire?

  • Third - and this was something else Nat pointed out - this email has no clear call to action.

If anyone actually bothered to read it, would they be compelled to do anything? If so, what would that be?

There are three links here, one repeated twice. Go there? Then what?

The final line of the email very passively asks for a quick chat, but it's hella vague and noncommittal. Nobody is going to go out of their way to make time for you.

You must have one clear call to action in the form of a request for a phone conversation at a discrete time that you suggest.

Not sure what times to suggest? Here's the secret:

It doesn't really matter!

If the prospect is interested but the time you offer doesn't work, they will work with you to find a time. But part of playing the game is directly asking for what you want: a phone call. By suggesting a time, you convey your professionalism with regards to time management: you respect the value of their time, and you present as though your schedule is neatly partitioned and organized like a professional's should be.

  • Fourth, the sample website is a poorly disguised fake organization that I made up and didn't bother to finish fleshing out (as you can see with the Lorem ipsum text near the bottom). If anybody bothered to look at it, it's not going to win them over.

  • Fifth, my portfolio website kind of sucks! It's all over the place in terms of tone because when I made it I wasn't totally sure if I was trying to be a freelancer or an employee. And it was made with a template, so it's not even an original design of mine.

I took Nat's advice and rewrote the email after I'd sent out like 25 of these. And I replaced the obvious mockup sample with one that was specifically targeted to my vertical: a real-looking website for a landscaping company that could theoretically be operating in my region.

But otherwise, the content didn't change much, and it was still just way too long.

This Cold Email Masterclass from Mailshake has some fantastic advice about crafting the perfect cold pitch. For my next marketing campaign, I plan to keep it to 3-4 pithy lines, and A/B test the "AIDA" and "BAB" structures here.

Something like this:

Hi (person),

Did you know that (name of business)'s website is really tough to use on a phone?

I ask because solving this problem is what I do best - crafting smart-phone friendly websites that will impress your visitors for many years to come, no matter the screen size.

My clients get overwhelmingly positive feedback from their customers when my sites deploy.

I'd love to set up a time to talk more about this. Are you free next Monday or Tuesday at 11?


Sam Sycamore

Founder, Sycamore Design

Better, right? I think so anyway. Please don't steal this wholesale! But feel free to tweak it to suit your needs.

Another upgrade coming in my next round: GMass for Gmail. For my first 100 emails I sent each one out individually and it took many hours. For $20/month, GMass will enable me to send potentially thousands of individualized emails with a single click, then track open and click-thru rates, and auto-send follow-ups a few days later to those who don't open the first message - all directly through Gmail! I am really excited to use it after doing it the long way first!

Sell Your Services

Once you have a few leads who are interested in your services, you need to set up a phone call with them to determine if the project is a good fit, explain how the process works, and answer any questions they have.

Remember: you are interviewing them to decide if you want to take on their project. They are not doing you a favor by hiring you - exactly the opposite.

They have a problem, and you are here to solve it. But first you have to figure out if it's a problem that you truly want to take on.

Again, this is a mindset thing. Your perspective will inform how you communicate about your services when your carefully memorized script flies out the window.

Sales is a whole thing unto itself that is beyond the scope of this post, but this I know for sure:

Don't name prices during your intro phone call!

Your goal here is to not to get the client to say:

"Yes I want to give you $XXXX for this service,"

but instead to say:

"Yes I agree that this is a good fit, please send me your quote for all of the things we've discussed today."

Over the course of the call, even if you never talk numbers, you will get a sense of what your prospect's budget might be, and whether they're looking for "good enough" or if they might be willing to pay a premium for something better.

If the client forces the price question, you need to redirect the conversation:

  • Ask what their budget is, as you are happy to accommodate a wide range of budgets

  • Explain that you offer many related services and want to be able to craft a proposal that is perfectly suited to their specific needs

  • Offer ballpark numbers as a last resort ("My rates begin at $XXXX for the basic package") to avoid wasting time on prospects who you suspect may try to lowball you

  • Be prepared to justify your price! Your clients are paying for your expertise, not the number of hours it takes to complete the project. They are paying for the countless hours you've invested in the skills that enable you to deliver on these kinds of projects. Those skills are valuable, and the industry as a whole is better off if we all push back against the race to the bottom that takes place on sites like Fiverr, Upwork et al. (No disrespect if you earn a living on these platforms- that is a serious accomplishment!)

By the end of this call, you should have a clear understanding of what the client is looking for. If you're a solid salesperson, they should be excited to receive an email proposal from you after the call, outlining the scope of the work and the fees for each service you provide.

Write a Proposal

This part is possibly even more terrifying than the sales call, because at this point you feel like you're on the right track but now you actually have something to lose - a warm lead who's going to be turned off by your price!


If you've done your work as a competent salesperson, you should already have a general idea of the price point this client will be comfortable with, and you've conveyed a level of professionalism that reflects the rates you feel you deserve.

You've already won them over personally and professionally during the phone call by being kind and friendly and assuring them that you are the best person for the job because you have the expertise to meet their specific needs.

Your prospect won't be scared off by the price if you demonstrate the kind of authority that they expect to see at your price point.

Here's an example of a proposal that led to a sale for me:

  • Design & Development: $1500

    • Bold, sharp, mobile-responsive design

    • Content management system (CMS) configuration

    • Technical search engine optimization (SEO)

    • Pages

      • Landing page

      • Services

      • Photo gallery

      • Testimonials

      • About

      • Contact

  • Copywriting: $500

    • I will provide you with a brief questionnaire to help me fill in the details and take on the tone and branding of your business

    • Adheres to Google’s best practices for SEO

    • Includes one round of revisions

  • Setup & Deployment: $200

    • Site deployment to web host, I recommend

    • Setup of CMS

  • Total: $2200

  • Optional Technical Support: $100/month or $75/hour

    • If you would like help managing your CMS or addressing minor technical issues, I am available for tech support on a monthly basis, or by the hour as needed

This format seemed to work fine for me, but next time around I plan to bill for SEO separately as I feel more competent about my skills now, and I think it's something distinct from design & dev. Speaking of which, I may also separate out those two categories in the future as well.

How the heck did I arrive at these rates?

Set Your Price

The reason it's so hard to find concrete advice about how to set your rates is that it's mostly up to you to decide how to do it. There is no secret formula, and what the market can bear will vary wildly between industries, demographics, regions, and continents.

I won't go too deep here into pricing strategies, but I will share my thought process.

When I did my review of 500 sites in my vertical, I paid close attention whenever I found a link to a developer's site at the bottom of an existing site. I would always scope out their sites to see how they pitch their services and find out if they share any pricing info.

The pricing that I found in my region started at around $1000 for simple template solutions, and upwards of $3-5000 for custom designs, Wordpress blogs, and SEO. I decided I should try to set my rates a little lower than the competition, at least to start.

I didn't want to charge an hourly rate, but when all was said and done I wanted to earn $100/hr for my time investment, so I set my flat fees based on my estimated number of hours multiplied by the target of $100/hr.

But I would be perfectly happy with $50/hr, and this target range gave me a lot of wiggle room: even if the project took twice as long as I estimated, I'd still earn a solid wage.

My first project clocked in at about $75/hr, so I feel really good about this pricing strategy going into my next round of sales.

Sign a Contract

Before you fire up Figma or write a single line of code, you need both parties to sign a contract that clearly lays out the scope of work and what happens if either party fails to meet their obligations.

Leon Noel recommends the Stuff & Nonsense Contract Killer open-source contract, and while I appreciate the framework, the cheeky British humor doesn't really jive with my style.

So I revised that contract for American English and posted it to my Github here - please feel free to use it if it's helpful to you!

(None of this has been reviewed by anyone I know in any legal capacity. If I'm able to land a few more clients then I intend to seek legal advice from a CPA - I would recommend that you do the same if you are serious about being self-employed.)

I insert the relevant details into this template and upload it to, which enables you and your client to register legally binding e-signatures online - no need for paper documents or faxing. This service is free for the first few, but you have to pay after you reach a certain number of contracts per month.

Determine a Payment Schedule

One key element of the contract is the payment schedule, which should clearly define how much your client owes you and when. I've tried a few different schedules, and these two seem to work the best for me:

50% upfront, 50% when all work is completed but before the site is deployed to its host


25% upfront, 75% when all work is completed but before the site is deployed to its host


I repeat:


You must have a down payment in hand before you start the work. And you need to be paid in full before your completed site is deployed to the host. This is to prevent a bad-faith client from taking your work and using it without paying you.

And you need to make this payment schedule crystal clear to your client. If not, there's a good chance that this could lead to headaches when you send an invoice that your client isn't expecting.

Receive Payments

When I was first getting started, I used Stripe for invoicing and payment processing. It worked fine, but I didn't love the 3% cut they took off the top.

Recently I've started doing all of my accounting and invoicing with FreshBooks. The basic plan is $15/month, and they take 1% from the payments I receive. So far I really dig this platform and I'm happy to pay the monthly fee.

I request payment within 7 days of sending out an invoice. My clients almost always pay within the day every time, perhaps because I alert them to the fact that the invoice will be on its way, and that it needs to be paid in order for me to continue with the work.

Now Get to Work!

And there you go, that's essentially everything that I know about the process of finding cold prospects, pitching my services, landing deals, and securing payments.

I sincerely hope you find this helpful. If you have a question that isn't answered in here somewhere, then I probably don't have a good answer to offer, honestly!

Best of luck to you! Let me know how you fare out there—we can trade notes.

If you enjoyed this piece and you want to keep up with my work, you can sign up for my email newsletter through this link. I promise to make every email something you will be excited to open!

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