Customer Success | April 7, 2023

Hacks to Make Retention Easier

Read time: 5 minutes

Written by:

  • Joel A Arnold
    VP of Revenue Operations Strategy

Don’t try to save a customer when it’s renewal time. It’s already too late.

We are focusing more today on retaining and growing our current customers. When we start emphasizing that, we may find that the damage is already done, or that things that make a customer happy happened long ago before they ever signed a contract.

Do the right things early so you can get the benefits a long time from now.  We will coach you on how to make your customers happy consistently.

Document Learnings

To give customers a good experience, it’s important to avoid asking them the same questions multiple times. When you’re selling your products, you’re probably already keeping track of:

  • Why the customer is buying
  • What they consider success
  • The systems they’re replacing
  • The important features they need
  • And many other details.

Our first tip is to have a standard way of documenting this information. Talk to your delivery team to see what they need to know from a sale. Identify which of that information is already being collected in the sales process or can be easily added. Create a document template and make sure it’s attached to an opportunity before closing the deal. Once the sale is made, share the document with the delivery team.

By implementing this standardized documentation, your customers will see that your company is organized and efficient. They won’t have to answer the same questions repeatedly, and you’ll need fewer meetings during implementation. It’s an easy and simple solution that will benefit everyone and set them up for success.

Your Kickoff Process is the Key Step

So you made a sale. Your next interaction with your customers will be to begin the implementation process. This is also an internal handoff point between your Sales and Delivery teams. With so many things happening at once, it’s easy to become disorganized or leave a negative impression. It’s important to prioritize and sort out these details from the start.

Scheduling a kickoff meeting right away is a great way to give customers a positive experience. We’ve seen companies take weeks to organize a team around a project, and delays like this can slow down the project’s momentum. We recommend setting specific days or times in your team for kickoff calls and having transition documentation ready to go at deal closure.

Invite representatives to all kickoffs so they can advocate for and translate for customers. For more complex projects, it may be helpful to have a pre-kickoff meeting where the Sales rep can brief the team, but this should be done on an as-needed basis.

Keep Reps Involved

The Sales team should continue to advocate for their customers even after the sale is made. It’s important to keep them involved in the deal until go-live, even if they’re not directly managing the implementation as project managers. They have a relationship with the customer, know the history, and can serve as an important liaison between your business and the customer.

We suggest making the Sales team somewhat accountable by tying their compensation plan to selling business that goes through implementation smoothly. This will give them a stake in the game and motivate them to ensure that the customer has a positive experience even after the sale is made.

When to Transition Account Ownership

This is a big struggle for a lot of companies, even one’s of significant size. When does ownership of a customer relationship change hands? The fact is that is going to depend on your business, but the following are things to consider:

  • Do your products and services lend themselves to being sold within a few months of the initial sale? If you won’t logically sell more in the first few months, then it may make sense to hand off the customer to your retention team sooner.
  • Is the expansion sale, i.e. the next contract after the first, going to be with the same buyer? If post-sale the persona changes, then it may make sense to transition to the retention team earlier on.
  • How long are your contracts? If one year or less, and the person responsible for renewing a customer is not the same AE that sold that deal, then you may want to transition ownership to the retention team earlier so they can become embedded before the end of the annual renewal cycle.


  • Keep a record of what is driving the purchase, what success looks like, etc., and share that with the implementation team
  • Schedule kickoffs quickly and organize the department around doing this
  • Make sure Reps that sold the deal are involved at least until go live and they have skin in the game
  • Understand when transitioning reps makes sense for your business

When you’re ready, here’s how we can help:

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