Winning every pitch: 8 expert tips for digital agencies

Coming up with creative ideas is hard; selling them to strangers is even harder.

The word "pitch" might bring to mind a baseball game—a fast throw, hoping for a strike. But in the business world, pitching is more than just hurling ideas at a client, hoping one will hit. It’s about knowing your client, making a connection, telling a story, and offering a solution that feels like it was made just for them. That’s why the best pitches often don’t feel like sales pitches at all.

For a digital agency, winning a pitch is part strategy, part creativity, and part psychology. So, how do you ensure that your pitches aren’t just fastballs but home runs?

As Prepr, we've seen many agencies pitch to their clients in different ways and after watching so many approaches, we've gained valuable insights that we'd like to share with you.

Here are some tips we've learned along the way.

When giving advice, it's natural to draw from personal experience. Jouko Huismans, Prepr CEO, for example, always emphasizes that pitching new ideas requires more than just words—it requires making them tangible and easy to grasp.

"Instead of just explaining a concept, show its impact," Jouko suggests. "Demonstrate how it works in different scenarios, so the client can see the results in action.”

This visual approach not only clarifies the concept but also builds a connection between the client’s needs and the proposed solution. As Jouko puts it, “The client needs to see the value, but also believe they can execute it.”

The key here is to simplify without oversimplifying. You want the client to see the value of your solution in a way that’s directly applicable to their business. If the idea is too abstract, it risks being dismissed. Therefore, keep it practical, relatable, and focused on outcomes.

Winning a pitch isn’t just about meeting expectations—it’s about exceeding them.

"Initially, I went all out on pitches, developing detailed concepts and strategies and presenting them with great enthusiasm. The result? Clients were often impressed but overwhelmed. This approach, while enthusiastic, failed to connect because the ideas seemed too complex for immediate implementation,” Bernard Jan Boekholt, Prepr CXO, mentions.

Realizing this, a shift in strategy was necessary. Bernard Jan introduced me to the concept of “going ACE,” which stands for Above Customer Expectations. This means incorporating an element into your pitch that truly surprises and delights the client, making your proposal not just a solution, but an experience.

However, the trick is to balance the ACE element with a solid, grounded proposal. As Bernard Jan explained, “You want to inspire and excite the client, but also give them something they can easily sign off on.”

A great way to go ACE is by pitching an Adaptive Website. This approach can make you stand out and show your expertise. An adaptive website, for instance, can dynamically customize content for various segments—like Segment A, Segment B, and Segment C—showing clients firsthand how it can address different needs and improve engagement.

Start with a clear example, such as adapting the homepage for different segments, to illustrate how this solution can make a significant difference. This strategy not only surprises and delights the client but also reinforces your position as a forward-thinking agency.

No matter how innovative your solution is, clients will always ask themselves, “Will this really work for me?”

To address this, Jouko stressed the importance of providing proof. Show how similar concepts have been successfully implemented in familiar contexts. Whether it's a case study from a well-known brand or demonstration of a successful project, providing concrete examples helps alleviate doubts. The goal is to build trust by proving that your solution is not just theoretical—it’s achievable and sustainable.

A crucial piece of advice from Bernard Jan was about the structure of the pitch itself. Many pitches begin with introductions and background information, but by the time you get to the heart of your proposal, the client’s attention may have waned. Instead, start with an engaging insight that immediately grabs attention.

For example, if your pitch is about improving user experience, start with a statistic that highlights the current problem. Or if you’re pitching to a hospital, you might start by mentioning a common issue faced by nurses that your digital solution can address. This approach not only wakes up the room but also shows that you’ve done your homework and are genuinely interested in solving their problems.

Even the most compelling ideas can fall flat if the client feels they’re too complex or unmanageable. Jouko highlighted the importance of keeping the initial proposal simple and focused. Start with a straightforward solution before introducing more advanced features.

This approach makes it easier for the client to say “yes” to the project, knowing they’re starting with something manageable. It also opens the door for future upsells, once the client sees the initial success. As Jouko noted, “Make sure you win the pitch with a simple, effective solution, and then add more value later on.”

The timing of your pitch can also influence its success. Depending on the situation, you may want to be the first to present—particularly if you have unique ideas that can set the bar for subsequent pitches. Alternatively, being the last can work to your advantage if you want to be the freshest in the client’s mind.

Regardless of your position in the lineup, Bernard Jan suggests avoiding times when the audience might be distracted, such as right after lunch or on a Monday morning. If possible, negotiate for a slot that will give you the best chance to engage your audience fully.

Beyond the rational arguments and impressive statistics, winning a pitch often comes down to trust. Clients are not just choosing a service provider; they’re choosing a partner. Bernard Jan and Jouko agree on how flexibility, empathy, and a collaborative spirit can go a long way in convincing a client that you’re the right team for the job. This emotional connection can be the tipping point that wins you the contract.

Bernard Jan and Jouko's last but not least tip is about continuous engagement.

“Do not underestimate the power of ongoing communication. Engage with the client between the briefing and the pitch presentation,” Jouko points out.

"Even when everything seems clear, come up with some questions and engage with your client. Each interaction deepens your relationship and can reveal valuable insights that give you an edge." Bernard Jan emphasizes.

Winning every pitch as a digital agency requires a blend of empathy, innovation, strategic planning, and relationship-building. By understanding your client’s needs, showcasing practical and innovative solutions, proving your credibility, and building a strong human connection, you can consistently turn pitches into partnerships. As our experts highlighted, it’s not just about the best idea, but about being the best fit for the client’s unique needs and vision.

So, are you ready to hit a home run?