What I’ve learned from pitching to hundreds of clients

What I’ve learned from pitching to hundreds of clients

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Most designers, marketers, and strategists dream of winning their first big client. They’ve had great luck attracting small businesses at the $5k – $10k range, and they’ve even built a great stream of income from that market. But they look around at their peers and start seeing bigger names on portfolios, or they start hearing about the $80,000 websites being closed, and suddenly FOMO (fear of missing out) and maybe even a bit of imposter syndrome starts kicking in.

I’ve been there. Numerous times, actually. First, at an agency where I was the CMO before being acquired. Second, at my design studio I launched with two friends. And most recently, in my freelancing side hustle.

In this article, I’m going to detail everything I learned from these experiences about putting together the most efficient client pitch. To fill in some gaps, I’ve asked other creatives and agency owners to lend a few words about their experiences. My hope is that after reading this, you have the confidence and tools needed to increase your price and start winning bigger projects.

But first, a brief clarification:

  • Big client in this sense does not mean the Googles, Nikes, or Apples of the world. I wouldn’t be a great source for winning these clients, because I’ve never done so myself.
  • Big client refers to clients with big budgets. These are websites or branding projects that go for over $50,000. A lot of times, these companies are in your own backyard.

Now, let’s get going.


Nail the discovery call

The discovery call is where you get to ask the company all of your questions that help build the pitch and proposal. Before I refined this process, my discovery call was focused on vanity questions that never helped guide me in the pitch. Questions like: What brands do you love? What websites do you like? What websites do you hate? 

I assumed they wanted a prettier website. I assumed they wanted to look trendy. Precisely zero of these assumptions were ever correct, and they never helped me when it came time to strategizing the pitch. 

If I was pitching a new website now, those questions might look like this:

  • What’s the goal of the new website?
  • Who loves your company the most? What do they look like, what do they do on the weekends? 
  • Where are you currently hosting your site? 
  • Is someone managing your plugin and theme updates?
  • What are the current conversion rates from the website?
  • What third party software is needed on your site?
  • What is working and not working on the website?
  • What’s the timeline for completion?
  • Who are the decision makers on this project?
  • If time and money were not an object, what would the perfect website look and feel like?
  • What’s the budget?
  • What do you need to see in our proposal?

Before asking these questions, I always paid the price of not asking technical questions in the discovery process. If I had $1 every time I failed to define the scope and paid for it dearly, I could retire in my 30s.

Plus, just highlighting the amount of research and development that goes into tying all of their software and specs into the website is enough to validate your higher prices. Remember, this conversation isn’t about you. Stay in diagnostic mode as long as possible and let the client know you have their best interest at heart. 


Abandon the wash/rinse/repeat pitches

Before I started winning larger projects, all of my pitches and proposals could be swapped out with little-to-no difference. Winning big clients means personalizing the experience every step of the way. 

“The pitch shouldn’t just be nuts and bolts and general vision board fluff; step out on a limb and include actual preemptive work made specifically for the prospective client. Use it as an ‘I can showwwww you the worlddddd’ moment. Not only does it help put their minds at ease when considering a less experienced creative, it also helps kickstart the creative process. If they love what you came up with, not only will you get the part, you’ll also have the luxury of knowing you’re the right fit vs going in completely blind *after* entering into a formal contract. Then, finish it with samples of your absolute best work.” – Sloan Anderson | Dangership (Halo Top, Ubisoft, Quest Nutrition, Activision)

The best thing I ever did for myself when pitching design projects was deleting my pitch deck template. Having a Keynote template made it entirely too easy to wait until 30 minutes before my meeting to fill in the blank slots and go off of the same script I’ve used 1,000 times before. Instead, I replaced the template with a simple checklist; a reminder of what all should be included in the deck. 

You’ll be spending significantly more time creating the pitch deck now, but the results of doing so will make up for it in the end.


Use your small size to your advantage

If self-deprecation was a CliftonStrength, it would be the first one on my profile. When I was working at Amazon, a co-worker told a room of conference attendees, “Davey is the first person to throw himself under the bus. It’s like he thrives off the humiliation.” So this is the part of the pitch that excites me the most; performing an accusation audit.

Former FBI lead hostage negotiator (and MasterClass instructor) Chris Voss uses an accusation audit as a means to turn negative thoughts and assumptions into positive talking points in his negotiations. 

“List the worst things that the other party could say about you and say them before the other person can. Performing an accusation audit in advance prepares you to head off negative dynamics before they take root.” – Chris Voss

When applying this technique in a pitch, you’re doing a couple things:

  1. Disarming the client’s pre-emptive assumptions about you.
  2. Letting the client know that you understand their perspective.

What kinds of accusations could a client have about a solo freelancer or a small agency? Here are a couple that I’ve come across:

1. Large agencies work faster than small agencies due to the amount of people available for the project. 

While the size assumption is true, larger agencies also have to have multiple projects moving at once to afford payroll and expenses. Very seldomly does a Creative Director only have one project on their plate at a time. As a freelancer, you can ensure that the client will receive 100% of your time and attention for the coming weeks.

2. Larger agencies have more experience, and therefore do better work. 

If I was going in for open heart surgery, experience matters. If I was handing over my life savings to a financial investor, experience matters. To redesign a website, there are other matters that take precedence, and I don’t believe it’s the experience they’re actually after. I believe it’s the feeling of safety in their decision. 

How do you make them feel safe? You show them you understand their company, their needs, and their audience, and you highlight your process of combining these understandings into the only solution that fits them. Sure, a bigger agency could arrive at the same solution, but it could take longer and cost more. Once the client feels like you understand them, their guide starts to lower and you’re in the running against the big dogs.


Emphasize your process

Having worked on the agency side and the client side, I can safely say that one of the biggest differentiators between agencies that win big projects and agencies that lose big projects is the process. 

Clients want to know what happens the moment they sign your proposal. Oftentimes, the person that you’re pitching to doesn’t have the final say in whether or not you’re hired, so outlining your entire process from start to finish gives them something to hand to their boss to ease their mind and excite them about the project. 

Something I always outlined in my web design pitch that started winning bigger projects are the key activities and key deliverables for each phase of the project. For instance, the first phase of a web design project would look something like this:

  • Research and discovery:
    • Key activities:
      • Kickoff meeting
      • Brand attributes workshop
      • UX strategy
      • Sitemap development
    • Key deliverables:
      • Meeting videos and notes
      • Sitemap
      • UX audit and suggestions
      • Estimated 4 meetings

I run this same level of detail for the design, development, revisions, and migrations phases of the project. Your prospective client should walk away from that meeting knowing what to expect in the coming months, and exactly when to expect them. 

Now you just have to live up to those expectations and make sure you’re not setting yourself up for failure. One thing I started doing was adding some room for error. If I thought the research phase would last four days, I’d give myself seven days. If design was going to take me two weeks, I’d give myself three. I would do this in hopes that I could under promise and over deliver every step of the way. And if I hit any roadblocks, I’d have some cushion to meet my promise. 

“When you pitch bigger clients, you need to think through all angles and put yourselves in their shoes: how will that person go back and sell this to her leadership team? What’s the anticipated ROI? What does updating the site look like? If you bring your 5 year vision to the pitch, and you’ve thought through every angle, there’s no question you won’t be able to answer.” – Natalie Micale | Oh Hello


Build a network of people you can lean on for help

The last thing I want to touch on here is the importance of your professional network. I’m lucky to have made friends with designers and strategists that I hold up to the highest regard. These people are quick to respond when I shoot a panicked text message or call them out of the blue to pick their brain on a strategy. Without this network, the lessons I’ve outlined here could have taken me twice as long to learn; if I even learned them at all. 

That’s just one of the benefits of joining Flywheel’s (free) Agency Partners Program. You’ll be immersed into the private Facebook group where you have access to hundreds of other designers, strategists, and agency owners who love to help each other grow and learn. If you’re building WordPress sites for clients, I’d strongly encourage you to join the program today.

If he didn’t have a career in marketing, Davey would still read every marketing book he could get his hands on. As a long-time customer of Flywheel, he joined the company as our paid marketing strategist, crafting ads and chewing bubblegum. Outside of work, Davey spends his time with his daughter Lydia, wife Karmen, and their house of furry friends in Lincoln, Nebraska.


Join these agencies: Learn how to land your first big client

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