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How to Re-Engage with Past Clients

Winning new clients is fun and rewarding; however, it can also be a challenging, time-consuming, and unpredictable process. Fortunately, new clients aren't the only audience that drive revenue for your web design business. By re-engaging past clients, you can create multiple revenue streams while dedicating less time and resources to sourcing new leads. In this article, we’ll offer tips on how to communicate with past clients and best practices for working with this important client base.

What we’ll cover

  • Benefits of re-engaging past clients

  • Ways to identify clients with revenue-producing potential

  • Effective communication techniques

  • Example re-engagement emails

  • Opportunities to leverage Squarespace's service add-ons

Why should I re-engage past clients? 

1. Build client retention and loyalty

Being proactive about client re-engagement is a great way to build on the momentum you've created by fostering an ongoing relationship. You put a lot of effort into building strong rapport and trust with your clients, so leverage your relationship with a client and continue building their business while generating more revenue for yours (a win-win). 

Clients remember when you do a good job. If they had a pleasant experience, then you've already started building foundational trust, which will make reconnection attempts more welcome.

2. Achieve long-term business goals

Re-engaging with clients benefits your business as much as it does theirs. From a dollars and cents perspective, research shows that: 

  • Acquiring a new customer can cost five times more than retaining an existing customer.

  • Increasing customer retention by 5% can increase profits from 25 to 95%.

  • The success rate of selling to a customer you already have is 60-70%, while selling to a new customer is 5-20%. (Source)

By building a re-engagement strategy into your client journey, you’ll create a reliable workflow to continue producing revenue well after your initial  project has ended.

3. Gain a consistent revenue stream

While finding new clients is vital to growing your business, it certainly isn't the only revenue stream you can rely on. Clients that have gone silent or inactive make up an often overlooked audience segment with revenue-producing potential. Refining your business strategy to re-engage past clients provides more value from your marketing budget. It also saves you from continuously pursuing new leads that may not be a good fit for your business.

How to re-establish contact with past clients (with examples)

When you gain new clients, create a plan to periodically connect with them down the line. Keep detailed notes on your clients and identify future opportunities to contact them based on their individual business goals and challenges. 

To make your re-engagement efforts more successful and time-saving, maintain a clean, up-to-date client database. Once you've mined your (organized!) client database and identified opportunities to reconnect with past clients, the art is in the approach. 

Best practices for re-establishing contact with past clients

  • Identify the right customers. Make sure the customer’s needs are still relevant to your business. Just because someone worked with you in the past doesn't mean they're worth pursuing again.

  • See if the customer is a good candidate for re-engagement. Look at your client’s activity and interaction with your messaging. For example, if they have opened your recent emails, they may be a better target than an account that has gone entirely unresponsive. Also look at how they've interacted with your business — did they buy multiple services or a larger package from you? These clients may be more receptive to doing more business in the future. 

  • Look at the last time you interacted with the client. The way you re-engage with churned customers will look different than a client whose previous interaction was more recent. Investigate if there was a reason for a drop-off in communication. Was there a missed email or any miscommunication? If there is a reason, a re-engagement email offers an excellent opportunity to amend and go above and beyond. 

Best practices for drafting re-engagement emails:

  • Personalization goes a long way. Use your client’s name, company's name, and other details about their business. 

  • Show that you did your research on their business by congratulating them on any recent wins or commenting on any new products. 

  • Offer a suggestion for an opportunity that they can benefit from. Share customized recommendations on how you can help them grow or save time.

A good re-engagement email shows you put time and effort into the reconnection attempt and aren't blasting out generic communication. The time spent here will yield greater response rates and return of investment for you.

Examples of re-engagement emails and why they're successful: 

Subject: Congrats on your product launch!

Hi Leo,

It's been a while since we spoke, and I wanted to check on you and your business! The last time we met, you were gearing up to launch your new fall collection. I took a peek at it, and the line is gorgeous.

To help you manage your growing customer base, I wanted to share some exciting new tools that incorporate seamlessly into your Squarespace site. Let's book a call and touch base on your business goals and how we can get you there. 

Looking forward to reconnecting!

Why this works:

  • The email is personalized with the customer's information, showing that you researched their company.

  • You're letting them know you want to recommend the right product to support their goals rather than prematurely pitching them a specific product they might not need. 


Subject: Take 15% off our VIP client services because we miss you

Hi there, Elisa! 

We haven't seen you in a while and wanted to check in on you and Company X. 

I have some new services that can help you save time while growing your business. 

Feel free to book a time on my calendar to chat. 

Happy to reconnect!

Why this works:

  • You're giving the client an incentive to come back to you, and the subject immediately indicates what's in it for them.

  • This is a good email to re-engage churned customers by grabbing their attention and making them feel valued and exclusive. 

  • The email uses a no-pressure approach to let the client come to you at their convenience. 

Circle-exclusive discount

Squarespace Circle members and their clients receive 20% off new annual product subscriptions, which is a great way to begin your re-engagement strategy.

What products can you offer past clients?

Launching new products and services is a great way to reconnect with old clients by sharing how your new offerings benefit their business. If your original project was successful, there's a good chance that they’ll repeat business with you. 

Squarespace offers a diverse range of products you can sell to clients, ensuring there is a product for nearly every facet of running a business. Before deciding which product to promote among your past clients, take the time to review each client’s file and assess which product(s) best fits their goals. 

A good rule of thumb is to make sure you can detail why the product you're selling can help achieve their specific goals. Identify any gaps in their business plan and recommend the product solution. 

Let's look at Squarespace add-ons you can use to re-engage your past clients.

1. Acuity Scheduling 

Acuity Scheduling is an online booking tool that syncs with your client's calendar. Your clients will benefit from automated appointment management and reminders, giving them the opportunity to efficiently sell and regulate their time.

Automated booking provides a better experience for your clients and their customers by reducing the time it takes to manually book and reschedule meetings. This reduced back and forth ensures a shorter sales cycle for your client, which frees them up to gain more revenue with new customers. 

Acuity also removes human error and calendar mix-ups, creating a reliable system that allows your clients to focus on their business and not administrative tasks. Ask how your client is currently handling scheduling. If they’re using a traditional method, guide them to transition to an automated system. 

Here are some key points to share with your customer when explaining the benefits of Acuity Scheduling:

  • Free up time and resources that are better spent focusing on your business.

  • Acuity Scheduling is built into the Squarespace ecosystem and syncs with your calendar, so you won’t have to manage a third-party calendar site. 

  • Automated scheduling means you'll enjoy a shorter sales cycle and serve your customers as quickly as possible.

  • Time zone conversions, double booking, or overlapping meetings are all taken care of when you use Acuity Scheduling. 

  • Keeping your customer data in one place means you’ll have a frequently updated contact list.

  • Appointment reminders increase your customers’ show-up rate — less wasted time and more revenue. 

2. Member Sites

Member Sites within your client's Squarespace site make it easy to share premium gated content and manage memberships. This can be used in a wide variety of ways depending on your client's business. For example, a fitness studio may offer exclusive videos for an extra fee, or a cooking school may offer workshops to select members. 

To identify which of your past clients are a good fit for Member Sites, look for clients that have grown a sizable following of engaged customers with free content that’s already attracting and providing value. 

A good time to offer gated or premium content is when a client's business has customers with whom they've established trust or brand familiarity. These customers are likely more willing to provide personal information or payments to gain access to exclusive offerings. 

You can sell Member Sites to clients who want to engage customers who’ve already shown interest in their offerings and services. 

  • Member sites are seamlessly connected with your Squarespace website, and you can offer customers private, members-only access via email capture or payment. 

  • You can host any content suitable for your business: blogs, photos, videos — all in your brand style. 

  • Exclusive content doesn't need to be downloadable. You can offer to unlock a free consultation or product demo. 

  • Offering exclusive content strengthens your relationships with your customer base. 

  • Providing content in exchange for email addresses is a powerful tool to build your email database and generate leads. 

3. Email Campaigns

Squarespace Email Campaigns offers a streamlined and straightforward way for your clients to grow and connect with their customers, all in their unique brand voice and design. Choosing Squarespace Campaigns for brand communications means that you can help clients hit the ground running to deliver on-brand, engaging emails quickly through a single platform. This practical integration saves time and makes sharing content and updates simple and frictionless. 

If you're unsure what product to use to re-engage with past clients, Email Campaigns is a great choice that benefits businesses of any size in any industry. Email marketing is an effective way to grow businesses and provide a meaningful customer experience.

Automating your client's email communication does more than save time and money. Here are some benefits you can share when discussing Email Campaigns:

  • Email marketing is known to deliver exponential returns on investment while being affordable to implement. 

  • Email Campaigns are simple to create, design, and launch. They don't involve complicated third-party software, and Squarespace makes designing on-brand emails straightforward and intuitive. 

  • Using email and building a subscriber base means you have an owned database of people with an active interest in your business that want to hear from you. 

  • Email Campaigns offers analytics to make it easy to see how users engage with emails. This enables you to create well-timed and personalized emails based on what subscribers respond to best.

  • The platform automates interactions with customers, which reduces manual work — you’ll save time while delivering a better experience to your customers.

  • Email Campaigns expedites the customer journey by using automated emails to guide customers from one stage to the next.

Additional products

Unfold is Squarespace's mobile app for making highly shareable social media content.

If your client has an active social media presence, Unfold is a great add-on to enhance social media marketing efforts. With Unfold, your clients can:

  • Create unique, on-brand stories for social media platforms like Instagram and Snapchat.

  • Make and publish a link hub containing links to all social media accounts and content. This link hub can be promoted in your social media bios.

  • iOS users can map out how your Instagram grid will appear to visitors.

Maintaining communication with past clients is a vital retention tactic, and promoting add-ons is a great way to start the conversation. 

When you build a proactive re-engagement plan for clients, you'll gain loyal collaborators who are more likely to use your services in the future. Reconnecting with past clients is a great way to provide lasting value for your business and gives them all the more reason to work with you again or even refer your business.

Plus, Squarespace Circle members can re-engage past clients with exclusive savings. Circle members and their clients receive 20% off new annual product subscriptions. Learn more about Circle membership benefits.


Want more? 

Check out Squarespace Circle, Squarespace’s program for professional designers. Along with exclusive content, discounts, and other perks, Circle brings professionals together from all across the globe to exchange advice while connecting with new clients and collaborators.