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Every agency should upsell at 3 months. Here's how.

Many agencies aren’t upselling soon enough. And they’re risking premature customer churn because of it. Knowing when to upsell a client...

Profile picture of Gal Zohar


8 min read

Many agencies aren’t upselling soon enough. And they’re risking premature customer churn because of it.

Knowing when to upsell a client can feel more art than science, but a study by Vendasta claims to have found the perfect time to expand your relationship with a client: 3 months.

Ninety days may seem like a short timeline to start upselling, but if a client is satisfied with your work in that time period then upselling can bring them more value quicker than they expected. Alternatively, if they’re not satisfied, it gives you a chance to recalibrate so you can keep their business. Both of those scenarios result in additional revenue you would have missed out on had you not initiated the conversation.

Upsells are easier to approach and able to start earlier than most agencies realize. Here are four critical steps that will help you upsell sooner successfully.


1. Investigate upsell opportunities with discovery questions during the sales process

Upsells work only if your client needs the additional services you’re proposing to them. So to upsell successfully in the first three months, start exploring where your clients might need more help in the future by asking discovery questions during the sales process. (Bonus: this will likely help you close more deals too).

The best discovery questions to ask change from client to client because every client and sales process is different. So instead of focusing on a set of specific questions, focus on learning more about your client’s needs: their pain points and goals.

However, keep in mind that the pain points and goals which result in a successful upsell are often things your client won’t consider relevant or aren’t aware of. So you’ll need to dig into the details of their business with them to draw out what’s really going on if you want to find opportunities to offer additional services that will be well received.

Discovery questions that help you uncover upsell opportunities

Below are a few discovery questions we’ve found helpful for digging deeper and uncovering a client’s true needs during the sales process.

  1. What brought you our way? Right or wrong, today’s clients often have well-developed notions of what they need, thanks to the Internet. This question helps you establish a baseline for the reasons a client is exploring the services and the potential results you offer.

  2. What are two or three primary pain points/goals your business is experiencing? Clients love to talk about what they're trying to achieve or the challenges they're facing. The answer to this question will help you understand which other services you offer that may also help a client in the future if they haven't explicitly mentioned them in answering question one.

  3. How are you currently addressing/working toward your pain points/goals? What’s working/not working? Can you give me an example? Understanding what a client has tried will help you frame any future upsells the right way. For example, if they have tried social media marketing before and say it doesn’t work for them, you can avoid pitching them something they don’t need. Or it may provide an opportunity for you to explain why your approach is different and might work better for them.

  4. If we’re three to six months into working together, and you’re excited about the results you’re seeing, what would those results look like? Asking this question helps you understand the work you’ll need to do and the results you’ll need to provide in the first few months in order to set up any upsell conversations for success (more on this in the next section).

  5. Long term, where do you want to be? What does that look like? Can you give me an example? Understanding how the client envisions themselves in the future will help you understand where you might be able to help today to get them there.


2. Build trust with new clients by starting with a smaller contract

Although it may seem counterintuitive, starting with a smaller contract often makes it easier to upsell a client at the three-month mark than starting with a bigger contract would.

For example, web design agency 10COM won more than a 50% of their pitches by picking up smaller projects like logo design on the Wix Marketplace. They would then upsell for additional work after the initial project was complete. 10COM proved their worth to the client and delivered the ROI they were looking for, something that’s easier to do in three months on a more limited contract. Upselling requires trust, and that trust can be built with smaller projects.

As B2B sales expert Andy Paul explained in a webinar with ringDNA, bigger deals make it harder to prove your value because they’re harder to support for both your client and your agency. The risk of failure, both perceived and actual, is higher for everyone involved.

Starting with a smaller deal, however, reduces the number of results you have to produce. Fewer results to deliver makes it easier to deliver them well and also creates a streamlined customer experience that increases your perceived value. (That also has a direct impact on things like price plasticity, retention and customer lifetime value).

This is especially important when you consider that a long-term relationship with a client is often worth a lot more than one big deal for a service business. One big job in marketing or advertising pays your bills for a year, one anchor client pays them for a decade.

3 examples of starting with a smaller contract for different agency types

The best way to arrange the initial deal, including determining how small you should start, will change from agency to agency and depend on the services you offer. But for most agencies, a winning strategy involves scaling back your initial engagement with a new client to just one to three primary goals so you can focus on executing on them really well.

Here are a couple of examples of how different types of agencies could approach this:

  • A web development agency could suggest starting with an SEO strategy/site structure before pursuing a full website build.

  • A content marketing agency could suggest starting with fewer posts per month and expanding into link-building services once the client is happy with their work.

  • A social media marketing agency could suggest starting with Instagram marketing and expand into Facebook, TikTok and more once the client sees results on Instagram.


3. Increase your perceived value through communication

The way you communicate with your client has a big impact on whether they'll be satisfied with their investment in you and whether they'll invest more.

Tiny moments of doubt, like confusion over work you delivered, even if it’s what they asked for, can negatively affect customer experience. And because customer experience is directly tied to your perceived value, poor communication can severely limit your ability to upsell.

However, while the importance of proactive communication may seem obvious to you, keep in mind it may not be as obvious to your team. So it’s essential to reinforce communication best practices with each employee who interacts with your clients to ensure they’re communicating your value appropriately as well.

Here are three simple communication tips that will help your employees create a greater perceived value for your agency.

Tie any work you do back to a client’s goals

Always explain why the work you’ve done is building towards the client’s overall goals.

For example, if you finish a project and email your work to a client with a request for feedback without an explanation of how it helps them, you’re leaving them to figure out how your work helps them achieve their goals. If your client does not immediately see how your work does that, their initial reaction might be frustration, even though you delivered exactly what they needed.

However, when you deliver work to a client with a line that explains, “Here’s what we did and why it helps you achieve [A DESIRED RESULT],” it helps them frame the work you did in terms of their organizational goals and positions you as an agency that works with intent.

Manage a client’s expectations for them

Never leave clients guessing what will happen next, especially early on in the relationship. This helps reduce the uncertainty and doubt that inevitably creeps in when clients are left to their own devices.

When you deliver work, let them know that you’re expecting feedback so that they know what next steps look like. Or when they sign a contract with you, send them an email that details what will happen next.

Little pieces of extra communication like this may seem redundant, but they can go a long way toward creating a better overall experience for your client and, by proxy, bolstering your value proposition in those vital first three months.

Share regular progress reports

Regular progress reports can improve client retention by 38%. That’s because they help reduce the fear that you’re wasting a client’s time and money, which is one of the primary risks associated with any purchase decision.

Regular progress reports also provide a natural place to start an upsell conversation. If you’re delivering the results you initially promised and can show improvement over time, reports create a transparent foundation you can use to offer a client more.

The regularity of your progress reports depends on the nature of your business and the work you’re doing. Base the report cadence on the length of your contract: Monthly reports for monthly contracts, biweekly for biweekly ones, etc. Just make sure you’re communicating what your reports mean and how the results tie back to your client’s goals.


4. Focus on how the upsell benefits the client, not on the service itself

Your client wants results, not another service. So when you’re ready to pitch an additional service to them, you need to present it as a uniquely valuable way to get the result(s) they’re after, not as a contract expansion.

The approach you should take to upsell will vary, and depends on the nature of your business and the specific client you’re upselling.

Here are three ways to think about an upsell pitch that will help you find the right framing.

  1. Show a client how they can achieve additional ROI by expanding the capacity of the services you’re already providing. For example, if you’re already doing pay-per-click (PPC) ad campaigns for a client, show them how increasing the number of keywords they’re targeting can help them increase sales.

  2. Show a client valuable new opportunities for additional ROI they may not have thought of. For example, show a PPC ad client how running ads on a new platform could help them increase sales.

  3. Show a client how they can overcome a challenge they’re facing with a different service. For example, if you provide SEO/content marketing services to a client that wants to increase rankings faster, you could offer a backlink-building service in addition to the content you’re producing for them.


Upselling earlier benefits you and your clients

An early upsell is always a win for both you and your clients. For instance, if you and your client agree that the relationship is providing value, an upsell helps them get more of what they need. In turn, you increase profitability as an agency.

However, if a client rejects the offer, you now have a chance to recalibrate and help them achieve the results they’re looking for before you lose them. That’s worth its weight in gold in today’s world, considering most clients leave agencies because they are dissatisfied with the quality of work.


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