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Chapter 5

The definitive guide to going Freelance.

By Kyle Racki and Ross Simmonds

Sales and Proposals

Chapter 5. Sales and Proposals
People shaking hands

Let’s be honest, selling is not why you got into freelancing. Still, it’s essential, or you’ll have no one to freelance to. Once you’ve got a solid marketing strategy in place sending you new leads every week, the process for actually turning them into clients goes like this: Qualify lead > Present proposal > Close deal.

Crafting an effective proposal is part of the basics when pitching your services. A proposal is simply a sales document that presents why you are the best fit for the project and articulates what you’ll deliver and when, along with estimated costs for your services.

While it might sound straightforward, this document is often what seals the deal. In this chapter we’ll talk about winning strategies to take your proposal from au naturel to va-va-voom.

Identifying High Probability Clients

When it comes to pitching to prospects you’ll want to spend most of your time targeting high probability clients. These are clients that you most want to do business with and who are most likely to do business with you. You’ll want to focus your attention on organizations and prospects where you’ll have the highest probability of success.

Create a list of prospective clients that fit your idea of what a “perfect client” is, whether a small non-profit, mid-sized design firm, companies in a specific industry which you have previous experience, or organizations that share your personal values. Don’t bother going after government Requests for Proposals (RFP) that will waste your time and win you no work. I also don’t recommend relying on services like Odesk or Elance, and certainly don’t touch any contest sites like 99designs, where you submit free work and only get paid if the client accepts it.

Even if someone asks you for pricing on a specific project it doesn’t mean they’re the right fit as a client. I don’t mean you should be overly picky—you still have to eat after all—but identify your deal breakers like people who are rude and demanding, don’t have a budget or have unreasonable timelines that can’t bend, and let them know you don’t think you’re the right fit for them and thank them for asking you.

Generating & Creating Leads or Opportunities

So you’re pumped now, am I right? I can practically see the lists of prospective clients swarming around your brain, just waiting to be captured on paper (yes – paper, I never leave home without my trusted Moleskine).

But where do you find these leads and what’s the next step? We’ve got you covered:

  • Marketing

    In the previous chapter we explored a variety of marketing tactics that are sure to get your desired clients’ attention. A good marketing strategy is the backbone of your sales strategy as it supports your prospecting efforts. For example, if you’re reaching out to a prospective client with a pitch or proposal, the first thing they’re going to do is run a Google search and conduct the most basic research to get a better sense of who you are and what you do. If your marketing efforts are paying off, they’ll be able to find you easily and get a sense of your work, your capabilities and skill and previous experience.

  • Associations

    A great way to generate leads and find new business opportunities is to become a member of a professional association. Whether you’re a member of a business, industry or charitable organization, it can be a direct path to some of your best prospects. Not only will you be meeting new people to share interests and ideas with, but it will also open the door to many networking opportunities that can result in new leads.

    Graphic Designers
    AIGA | the professional association for design
    Graphic Designers of Canada
    RGD | The Hub for Graphic Design
    AIGA | the professional association for design

    Welcome to The Association Of Illustrators
    Society of Illustrators

    Copywriters & Editors
    The Professional Copywriters Association
    The Editorial Freelancers Association
    American Copy Editors Society

    Content Marketers
    Branded Content Marketing Association
    Canadian Marketing Association

    IT Professionals
    IEEE Computer Society

  • Referrals

    Freelancers know that the best way to get clients is through referrals. Your first client was probably the result of a referral. But like everything else we’ll talk about, generating referrals takes work.

    Don’t be afraid to ask for a referral from a client that you trust. Although they love your work and would be happy to refer you, it’s probably not top of their mind. Once you get it, don’t forget to show gratitude. This might seem like standard manners but it can go a long way in terms of generating even more referrals.

    Finally, make referring easy for your clients. Are your services easy to define? Do your clients have a good understanding of your specialized skill and the services you offer? When people know what makes you unique, it’s easier for them to make the sale for you.

The Importance Of A Quality Proposal

The only way to get your proposal to the top of the pile is to create a masterpiece that’s worthy of your client’s attention. Proposals are generally all the same in terms of their intent, but the quality in the proposal is what will win you the contract.

The best proposals are ones delivered within existing relationships. Meeting with prospective clients and discussing the project at a discovery level before issuing a proposal will strengthen the quality of the document and enhance the level of consideration that will be given to it.

  • What Goes Into A Great Proposal?

    A great proposal demonstrates your understanding of the client and the particular needs you plan to address. In some ways it’s like a brochure customized for one specific client. It will get them excited about what you can do for them, outline the pricing and direct them to sign off on an agreement so you can close the deal.

    When thinking about the structure of your proposal, it might be something like this:

    • Cover Letter: While it’s not the most important part of your proposal, I’d be lying if I said that first impressions don’t matter. The right cover letter will help give the right impression to your potential client and prospect.

    • Approach: Remember earlier when we talked about the importance of having a process? In the approach section of your proposal you need to talk about how you’re going to deliver and what the process will be like on the other end for your client.

    • Scope & Milestones: This is the real meat of the proposal. It describes the exact deliverables the client will receive (if they’re known), and when they’ll receive those deliverables (if a start date isn’t known yet you can just say “Week 3”). Be diligent here because your clients will expect everything written in this part to be what they receives and may refer back to the proposal if you have a disagreement on deliverables.

    • Budget: This should be pretty straightforward. This is where you will highlight the budget you’re proposing to the client. Proposify gives you a budget table that is ready to be customized making it easy for you to allocate time for both fixed rate and hourly work.

    • Company/History: Alright, this is where you have a chance to sell yourself. This is where you will want to tell the prospect how great you are and why you’re the perfect fit for this project. Talk about your strengths and don’t be shy when it comes to bragging about your accomplishments.

    • Team: If you’re going to bring someone else in on this project, don’t forget to include them as a part of the team. Highlight their skills, talents and experience similar to what you did for yourself in the history section.

    • Work Examples: Even if you have your work on your website don’t forget to put in your case studies and testimonials in the proposal. Don’t bother putting all your work in the proposal, just pick three examples specific for this client that show off what you can do.

    • Terms & Conditions: It’s often overlooked but it’s something you shouldn’t underestimate. The terms & conditions of a contract are very important and will ensure you don’t get burned. Proposify delivers pre-written terms & conditions that you can customize to your liking.

That’s the underlying framework of every quality proposal. I know some of these items may not be required but they’ll definitely help set you apart from the competition. I’ve witnessed first hand, too many people assuming they had a project in the bag and missed out because they didn’t put in the effort to deliver a quality proposal. Don’t make that mistake.

Other important elements to a winning proposal include clearly articulating the objectives and end goals of the project and illustrating how you’ll get there. This helps the client to compare your approach to other (obviously less riveting) proposals. Clearly specify and quantify the project deliverables, and be sure to draw a clear line where the project ends. Avoid jargon and other “fluff” words. Short concise statements appeal more to prospective clients and let’s face it; it makes your proposal more enjoyable to read.

Price your proposal fairly and realistically. If you’ve previously discussed the project with the client and have a good understanding of the client’s means and the project scope, you’re better positioned to price the proposal appropriately. Too low or two high of an estimate can ultimately kill the sale. When the price is right, you’re better positioned to close the deal.

  • What Tools Can Help You Win Business?

    You’ve thought long and hard about how you’re going to bring magic to this perspective client, you’ve met with the client face-to-face and are confident you have what it takes to win the contract. As you sit down to put pen to paper, keep in mind that presentation matters.

I’m not just implying that your proposal needs to look awesome (although it should); I’m talking about demonstrating some creativity and resourcefulness by using a variety of tools that kill two birds – make your proposal relevant and interesting and look good.

The traditional way to make proposals is with document editors like Word, Pages, InDesign or Google Docs, however it can really increase your efficiency to use cloud-based proposal management software like Proposify, which lets you reuse content a lot more quickly and cut your proposal time down. It will also help you do stuff like manage your proposal deadlines, gather data on your win/loss rate, send your clients online proposals they can sign-off on digitally and a lot more.

There are also tools to help you with the presentation of the contents of your proposal too. Using Prezi, for example, is a great way to show your client the details of the proposal in a captivating way. It’s a great tool to leverage when you actual pitch your proposal. The other benefit to using online tools like Prezi is that potentially millions of visitors to that site might see your work. You can also embed your prezi to your own website or share them across other social platforms. Like I said…two birds, one stone!

Closing the Deal

“Put that coffee down! Coffee’s for closers.” - Alec Baldwin’s Blake in Glengarry Glen Ross

All of this hard work of marketing yourself, sifting through leads, meeting with prospects and writing proposals will be a complete waste of time if you can’t close the deal. Now, the good news is that if you’ve done your work upfront and only written proposals for qualified leads your close rate should be pretty high. Still it won’t be 100%, it never is. People get busy and lose their focus on the project, or there are internal changes at their company that move it to the backburner. Another freelancer may have come in a bit lower in price than you. There’s nothing you can do about these situations.

What about the things you can do to help close the deal? Following up is the simplest, most effective way to keep deals from going cold. If your prospect asked you for a quote then you have permission to pick up the phone and contact them as many times as you need to in order to get a definitive answer. Obviously you don’t want to be a nuisance calling them five times a day, but if you called once a week it wouldn’t seem out of place.

Try the phone first as it’s a more personal way of communicating and it also puts them on the spot so they can’t ignore you! If you get their voicemail just leave a short, pleasant message saying “Hi it’s Kyle calling, it’s been a couple of weeks since I presented my proposal for web design. I just wanted to follow up and see when you’d like to start the project or if you have any more questions before moving ahead.” Then send a follow up email stating basically the same thing. That’s it - real simple! Even if the prospect is inconsiderate of other peoples time (sadly, many are), he will eventually feel bad for putting you off or just want to stop being asked about it, so he’ll get back to you with either a yes or no. If the answer is no, be sure to learn why and see if there’s anything you could have done differently so you’ll know for future proposals.

When your prospect gets back to you, be sure to address any further questions he has over the phone, and if he’s sold then close the deal in the following way:

  • 1. Get the contract signed.

    It’s easy to get digital signatures without the hassles of printing, scanning and emailing. The contract should include all your basic terms and conditions along with the scope and price/rate of the project. You can find some sample statement of work and consulting contracts on Docracy. Just use the type of contract that best fits your project and add your details to it. When starting out it’s worth paying some money for a lawyer to look at your contract to make sure it’s legally binding. Once you have a standard template you shouldn’t need to consult a lawyer again except for rare occasions where the nature of the agreement is very different from your standard ones or your client wants to add some terms to it.

    Some freelancers are hesitant of using contracts because they think it shows a lack of trust. Get that idea out of your head right now—professionals use contracts(you’re a professional, right?). No one is doing favors for anyone. You’re running a business and this is a financial exchange between the two of you. Both parties want to be protected in the event something goes wrong, and clients are usually less likely to act shady if they know they’ve signed a contract with you. If your client refuses to sign a contract it means they are probably not worth doing business with in the first place and you just saved yourself a lot of time and money.

  • 2. Collect your deposit.

    This should be in your proposal and contract so there’s no surprises. You should always collect a deposit before beginning new work, especially if it’s for a new client you’ve never done business with before. This creates a feeling of reciprocity between the two of you, and gives you confidence to make room in your schedule, perhaps even turn down other projects to work for this client. It’s easy to collect deposits online using Paypal, Stripe, email money transfers and so on. Avoid cheques like the plague unless your client promises a cheque will be ready at your kick-off meeting.

    Trust me, there’s no better feeling than hearing that sweet, whooshing sound of a new email arrive in your inbox confirming the funds were successfully deposited to your account. You just closed a deal! Now celebrate with a cup of your favorite dark roast.

Sell to existing clients

There’s one more point I want to make about selling, which is the easiest deals you’ll ever close will be with existing clientele because your cost of sale goes down. What’s that you say, cost of sale? Allow me to explain:

In many types of businesses a key metric to monitor is your customer acquisition cost, or CAC, which is how much money you had to spend to acquire a single customer. For example you may have spent $5,000 in advertising during a given month and gotten 100 new customers from that, therefore your CAC is $50. Obviously each customer should be paying you a lot more than $50 for a transaction in order for the economics to work, otherwise you’re losing money.

Well you’re a freelancer and you don’t pay for advertising (I hope), but you put your time and money into other activities that bring you new clients like events, meetings, coffees, proposals, pitch meetings and so on. Every project you win has a cost associated with it. Winning a project with a new client naturally has the highest cost because it took you more time and money to win it.

But existing clients have an almost free cost of sale associated with them since they are coming to you and you don’t have to spend time convincing them you’re the right freelancer for the project or feeling them out to see if they’re a good fit. All you need to do is tell them how much it will cost, get their approval and move ahead! You probably don’t even need to get them to sign another contract since they’d be bound to the original one they already signed.

Make it a habit to keep a list of your best clients handy and regularly stay in touch with them. Maybe every month or two you send them a customized email with a link to a helpful resource or congratulate them on some recent news you heard about them in the press. Here’s some example emails:

Hi Stacy,
I hope all is well. Congrats on the recent news of the big investment you landed, that’s amazing and well deserved. Let me know if there’s anything I can do to help.

Hi John,
I just wrote a blog article on conversion optimization and I thought of you since I know it’s something you’ve struggled with in the past. [link_to_article] Let me know if it helps!

That’s it - no need to send a long winded pitch. Focus on providing value to them, be friendly, congratulatory or helpful, and you will stick in their mind the next time they need something you can provide.

We are a really small team, and as the managing partner who also directs and edits the majority of our work, I have a lot of things on my plate, so logistically having a tool like Proposify [to create stylized and customizable proposals] is huge...It feels like having a part-time employee on the team.

Dan Napoli Owner
Disconnected Media


  • Identify the ideal client and create sales materials and marketing materials tailored around their needs and wants from a supplier. Use your knowledge of what they want to create content that will resonate with their business.
  • Leverage groups and associations to build a broad network quickly and have the ability to make powerful business connections that are built on trust.
  • Understand the art of the proposal. It’s important to highlight the key aspects of your proposal including the cover letter, approach, budget, history, team and terms.
  • Embrace technology when identifying opportunities to improve your sales cycle. It’s important to be effective and efficient when it comes to developing proposals and prospecting. Embrace technology as a tool that can help.
  • Learn to close deals by persistently following up on proposals you’ve sent and simply ask your client when to begin the project. Sell to new and existing clients.
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