My Top 10 Learnings From Ben Chestnut, CEO of Mailchimp

So the recent SaaStr Annual 2020 at Home was a smashing success.  3 days, 100s of roundtables and sessions, and 1000s of 1-on-1s.

I was fortunate enough to lead two discussions, the first with one of my favorite CEOs, but one I hadn’t been able to do a deep dive with before, Ben Chestnut, CEO of Mailchimp.

I’ve been a 3x customer and watched Mailchimp over almost 20 years grow to be perhaps the first SaaS company to hit $1b+ in ARR being 100% bootstrapped.

My top 10 learnings:

1. Yes, bootstrapping really does take 3-4 years longer.  We’ve talked about and written about this many times before, but Ben vigorously agreed.  Mailchimp took years to transition from an agency to a software business, and then years until it finally took off when they added freemium.  In fact, really, it took 2 years to get going and 4 years to hit Initial Traction.  Bootstrapping is less a lifestyle than something we just do when it’s the only or best option.  More here.

2.  You may not need a moat. Maybe let them go if they aren’t happy. Happiness is a moat.  I’ve had a lot of discussions over the years on what constitutes a “moat” for many SaaS products.  Ben confirmed there is no moat at Mailchimp.  He said in fact, he doesn’t want moats.  If a customer wants to leave, he wants them to leave.  And hopefully earn them back later.  “Customer happiness is a moat”.  You don’t get that if you make it hard to leave.

3. Phase 2 might take 12 years to get to. It’s OK. Talk to more customers to know when you are ready.  Mailchimp in the past 2 years has grown from an email company to a marketing automation company.  That’s a big change, and their own version of finally going upmarket.  But boy — they waited!  Almost 20 years.  They waited until $1b in ARR to go upmarket more, to add a much richer and broader product suite that took them out of “just” email.  So do at the right pace. A bit more here.

4.  It can take 24+ mos. to get to real Product Market Fit. Mailchimp didn’t really have product-market fit until it went Freemium a full 2 years in.  We’ve talked for years on SaaStr on how you have to budget 24 months to really get something off the ground in SaaS.  Here’s another case study.  It also took Mailchimp 24 months, and a tilt to freemium (which they initially resisted), to even get to $1m in ARR.  A bit more here.

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Mailchimp and Salesforce Integration

If you use Mailchimp and Salesforce together to manage your leads, keeping them in sync is vital. But that shouldn’t come at the cost of your precious time and effort. Have do that grunt work for you.

It is a simple tool that connects your favorite web apps and automates your tedious manual work so you can spend your time working on things that matter to you.

You will see the ‘Add Accounts’ screen. Here you will connect your Salesforce & Mailchimp accounts to Now, let’s enter our account credentials. We always keep your data secure with bank-level encryption. Alright! Our apps are connected. Now, let’s build this automation, also called a Bot.

First, let’s focus on Mailchimp. It is our trigger app, which starts our Bot. This Bot triggers every time there is a new subscriber in our Mailchimp account. By the way, Mailchimp has a lot more triggers that can come in handy for other use cases.

Now, let’s move to Salesforce. It’s the action app that performs our desired action. In this case, we want to create a lead on Salesforce for every new Mailchimp subscriber. However, you can modify this Bot and save each new Mailchimp subscriber as a contact instead, on Salesforce. And just like Mailchimp, there are a bunch of other actions in Salesforce that can come in handy for other use cases.

This template also comes with standard contact fields that are already mapped for you. But you can override it and make any changes you want. You can map more details to Salesforce by taking the help of these additional fields.

We’ve now set up our bot. Click Done. And, test it out. Now, come back to your dashboard. Alright, it looks good. Let’s check our Salesforce. There you go! Your bot will now run in the background and do all the work for you. You don’t have to do it manually anymore.


Learn more about Mailchimp , SalesforceAutomateio


Best Free Email Marketing Software 2020

In this video, I’m going to compare the best free email marketing software for 2020 you can use to build your email list. I’ll also go through an email marketing software review, more specifically, the “free plans” offered by popular and best email marketing platforms – MailChimp, MailerLite, ConvertKit, and SendInBlue. When it comes to email marketing for beginners, this review and comparison video shares free email marketing platforms you can use to start building an email list.

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