From Ownership to Strategic Leadership: Embracing the CEO Role

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Do you struggle to write proposals? Do you know the 2 keys to winning more clients in the proposal stage? Mastering the art of creating fast, high-quality proposals remains crucial for agency growth. The best way to guarantee your proposal has a chance to stand out from competitors is to ensure speed and accuracy. That is why our featured guest is sharing how he went from owning an agency to creating the tool for overcoming proposal anxiety.

He spent years thinking about ways to turn what was often the worst part of the job for him into an easier and more enjoyable process and eventually launched a software that does just that. Learn more about Joe's entrepreneurial journey and insights into the agency world.

Joe Ardeeser is a former agency owner and entrepreneur who ran a web design shop and high-end WordPress shop for twelve years. He shares his journey from agency owner to launching his latest venture, Smart Pricing Table. Joe discusses his early experiences in the agency business, highlighting his desire for independence and the challenges he faced, including developing RSI and chronic back pain, which led him to hire his first employees out of necessity. He reflects on the things that took away from his agency’s growth and the way to keep improving your proposals until you’re yielding the expected results.

In this episode, we’ll discuss:

• 2 keys to drafting a successful proposal.

• Learning from past mistakes to continuously improve your proposals.

• The solution to overcome proposal anxiety.

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When Setbacks Become Stepping Stones in Agency Growth

Joe's story begins with a common entrepreneurial struggle: the desire for independence. Truth be told, he didn’t like having a boss. After working in a corporate environment that stifled his creativity and autonomy, Joe ventured into freelancing. However, an unexpected challenge arose when he developed an injury that hindered his ability to perform tasks like typing. This setback, rather than derailing his ambition, became the catalyst for hiring.

Enlisting help helped Joe realize that delegating tasks could free him to focus on higher-level strategic thinking. The first time he realized the critical role played by that initial hire was during a simple errand. Upon his return, he realized his employee kept everything running smoothly in his absence. He was hooked. The experience highlighted the power of collaboration and the importance of building a team that could share the workload.

As his agency grew, each strategic hire—from developers and designers to a pivotal sales manager—freed Joe to focus on broader business strategy. The decision to hire a salesperson, though questioned by some who thought the agency was too small, proved particularly transformative. By delegating the pressure of closing deals, Joe could finally step away from the day-to-day stress of revenue generation.

Little by little his hires and careful delegation led to the big day when a client was onboarded without his input at any level and not even knowing the client prior to that moment. It was the moment he knew he had transitioned from an owner to a CEO.

2 Keys of a Successful Proposal: Speed and Precision

As for so many agencies, Joe recognizes lead generation as a significant pain point for him. Luckily, the agency got tons of leads from Clutch back in the beginning. Still, they did a lot of one-time work and hadn’t cracked the code on landing retainers.

#1 - Speed

Back then, Joe hated writing proposals, because of the urgency that came with it. In his experience, every day that went by meant the odds of getting picked went slimmed. In his experience, clients often go with the first-engaged vendor. By reaching out immediately, an agency demonstrates its commitment and also capitalizes on the momentum of the prospect's interest.

#2 - Accuracy

Secondly, the proposal, scope, and expectations must be accurate. If not, the project could blow up post-sale and become a nightmare. These two proposal conditions, it having to be ready quickly but also be high-quality, are two elements that come together to create what Joe calls “proposal anxiety” which is one of the bigger stressors in agency life.

Your proposal should be detailed to avoid painful mistakes like greatly underestimating the time and resources you’ll be investing on that project. According to Joe, it should be detailed enough to provide “handles to grab onto” without being obnoxious. Vagueness will lead to situations where all your resources keep getting sucked into that project without the proper limits to stop at a certain point.

Why You Should Record All Issues with Previous Proposals to Yield Better Results

Ideally, agency owners should keep a repository of all the learnings from previous projects. Record all the issues you’ve ran into that could’ve been avoided by clearing it up in the proposal. In this sense, Joe recommends having reusable items that can be improved over time as you test through agency work. Many things might change in these documents as you get better and better but Joe makes two main recommendations for making successful proposal drafts:

• Make it visually appealing. Even if you are making very detailed proposals, don’t underestimate the importance of the layout. If it basically looks like a wall of text the prospect will be overwhelmed and be less likely to read it, and that will inevitably lead to expectation issues. Lay out your proposal so it is digestible by creating bullet points as visual clear representation of the work included, limitations, and upsales available.

• Define the “Spirit of the work”. Joe particularly recommends taking to the time to define this as something you can always come back to if you feel the scope of the project is getting out of hand.

As you continue to test and improve upon this document it will become a proposal that’ll help you yield the expected results.

The Solution to Proposal Anxiety

Joe became obsessed with the idea of creating a more structured and efficient approach to proposals to streamline and agency’s proposal processes. His goal was turning what is often the worst part of the job into something actually enjoyable.

With this mission in mind, three years ago he took his vision to the market in the form of Smart Pricing Table, a proposal software built for marketing agencies. As someone who ran an agency for many years, Joe knows his software offers the type of features agencies want and can provide the structure to provide quick and accurate proposals.

By focusing on the needs of agencies and incorporating feedback from users, the software has evolved to meet the changing demands of the industry. This adaptability is vital, as it allows agencies to continuously refine their proposal processes and stay ahead of the competition.

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