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Stop Aiming At Happiness: Uncommon Truths About What Really Fuels Retention

Anna Jacobsen

Head of Customer Success + Onboarding, YouCanBook.me

Minneapolis, but CA is home
Anna Jacobsen

Anna Jacobsen

  • head of customer success & onboarding at youcanbook.me (calendly competitor)
  • head of customer success and lots of other things at Drip


  • old/new ways of thinking
  • data that shows better
  • 4 ways to take responsibility for your customer's success

Old/New ways of thinking

Prevailing wisdom says to make your customers happy. Is this true?

In The Effortless Experience, making your customers happier makes them more loyal.

But in practice, you can make customers really happy and they still churn.

On the flip side, really angry customers that complain all the time in your support can stick around forever.

Why is this?

Why do unhappy couples stay together?

We stay in a relationship when something is good enough.

If you're getting a good enough experience, you'll stay for a long time even if the situation isn't ideal.

There's a difference between meeting the needs of the customer and delighting the customer. By meeting your customer's needs, you're already doing the most economically viable thing you can do.

  • Example 1: Docker went from 2,500 job postings in 2014 to 43,000 in 2015. Massive imbalance in supply/demand.
  • Example 2: Fender Guitars churn went from 40% to 90% over ten years
  • Example 3: Drip opened up a free plan after their acquisition. It drove growth, but got a completely different type of customer.

In all these examples, the company is great, but there's a problem with the customer.

What did they do?

  • Docker: training program to get more people certified
  • Fender: $10/month guitar education app
  • Drip: instead of focusing on how to use Drip, Drip is focusing on teaching businesses the principles of marketing

These changes help users use the product more, use more features, and work more independently.

These are all metrics of effective adoption. Don't ask if your customer is happy, measure how

You're the expert in the room - help your customer succeed!

4 ways to take responsibility for your customer's success

1. Coach, don't sell


What does a sales person look like in your mind?

What does a sales person look like?

The most effective form of sales is to help people. Don't pitch your product with a slide deck, help your customer with their strategy to succeed.

2. Plan your customer's success

Good customer success plans measure ROI for the customer. Upselling/cross selling rate, rate of adoption, # of meetings, NPS, milestones achieved, and customer churned are all internal measurements that don't measure the core of how much you're actually helping your customer.

Ex: MailClark

3. Map processes to features

Successful sales calls spend the call listening, and the very end of the call making recommendations.

4. Scale with success playbooks

Demo process at Drip (from Anna's 2016 atendee talk)

Most people would activate, but if not they fell into a Drip campaign

The Payoff: Renewal Time

Typically, sometime before you charge a user you send the user an email letting them know they're going to get a bill.

If you get fancy, you might inject some dynamic stuff showing the user how much they used the product.

The unconventional way is to have a relationship with each customer and when it's time to renew, you upsell them. This upsell needs to be based in what the customer's need is.

Final Thoughts

  • happy customers still churn
  • our product probably isn't enough to get all users to be successful
  • focus on the needs of your customer, not delighting them. Don't be afraid to say "no" to two-hour calls for a $10/month customer so you can be freer to help higher valued customers to achieve their goals.
  • Be judicious with high touch customer service. Reserve it for people that give you a lot of money.

(P.S. If you’re having trouble scheduling meetings with your prospects and customers, book Anna at anna.youcanbook.me)


Do you have tips on getting users into demos and then converting customers?

Look at how much stickiness you introduce in the trial phase.

For demos: make it prominent in your site, include it in your emails, put it everywhere.

For converting: force education. Don't give users the option of not scheduling an onboarding session. Make it mandatory.

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