Inside Carrot: 3 Leadership Lessons From The Front Lines Of Customer Success

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Customer Success Post HeaderWorking the front lines of any business can feel like you’re the grunt worker or the person that’s completely expendable. You’ll hear folks tell you to delegate basic tasks and hire someone who can help answer client questions. That these tasks aren’t the ones that will take you to the next level.

Because of this perception, being hired or working those support-based positions can seem like a chore or like it’s the bottom of the rungs on the corporate ladder, but we believe differently at Carrot. We believe that you can’t have a great product or team unless it starts from those initial interactions — which is why it’s best to hire great leaders, even on the front lines — because the front line is where leaders are built.

I could dive into many reasons this is applicable but will limit this to three leadership lessons that I — Andre, a Customer Success Hero — have learned at Carrot from helping our team answer over 100 inquiries every single day.

Customer Success Lesson #1: Put Yourself In The Place Of Your Prospects

In support, we throw out a lot of information immediately and it can even be overwhelming if you have used websites before and focused your efforts toward online marketing.

It’s drastically more confusing if you have never touched a website before. And then you login and see our system… and holy cow!

Imagine all of the terms we will throw your way — from setting up a domain and seeing TTL, CName, 301 redirects, MX Records, A Records, IP Addresses. Then imagine hearing about keywords and keyword phrases, longtail and shorttail, and trying to decipher if they’re the same things and which you really need to use. Then you have SEO for real estate and PPC for real estate, Paid Traffic, Retargeting, USP, and so many other terms! Where do you start? Where do we start?

That’s kind of what it feels like when you’re asking support teams questions, isn’t it?

You’ve faced this in the real estate industry, as well. Typically, it happens when a motivated seller approaches you and they’ve reached a point of being overwhelmed and need help — quickly! Let’s face it, supporting those you serve and your business is all about triaging and facing each situation with brand new eyes and an open heart.

And above all, understanding where that person is coming from and their experience level. Here are a few ways to help put yourself in someone else’s shoes and find a way to best serve them:

  • Ask clarifying questions.
  • Find out what problems the person is experiencing.
  • Find out what interests they have/what excites them.

When you take the time to get to know your prospects — their story and hopes and dreams — then you know how best to approach someone’s situation and what their next step and yours should be.

Customer Success Lesson #2: Be Lovingly Honest

You can’t buy everyone’s house. You can’t work with every investor. And Customer Success teams have difficult conversations. One conversation we have regularly is when we find copyrighted information and have to respond. When people scrape our site and content, the support team has to tell them to take the content down. And, as you might expect, that’s an uncomfortable conversation to have.

One day, I found myself in a situation where it was an actual Carrot customer that was scraping our content. That’s a big no-no. Our terms explicitly prohibit this.

What’s worse? This person had been a customer for about two years.

It was a hard conversation and not one that I looked forward to pursuing. But I ended up having a lot of empathy for him and I desperately wanted to find a solution — even though what he was doing was technically illegal. I reached out and told him the pages would need to be removed and he agreed but was shocked that this was the case when he was a customer. And I understood… it’s a very grey line.

After lots of thought, both in and out of the office, the support team didn’t find an answer for over 48 hours and I was concerned about how we could help the customer without offending our policies.

Finally, I had it!

Although it was the end of the night when I came up with the idea, I woke the next day invigorated and wrote him back and, saying, “Here’s what you can do: You can add a link on your site menu to our own website content.”

Of course, we don’t have all the answers immediately, or even at all, but it’s important, to be honest with yourself, your company, and – most importantly – those you serve. Even if that honesty is hard.

And always make sure to balance that honesty with a healthy dose of empathy and — dare I say? — love.

  • Tell folks “yes” or “no” and try to find a solution or coach them on what’s best for the end game.
  • There is always a way, but you may not always have the solution or be able to help. Accept that.
  • Offer what you can, but don’t jump the gun on making commitments before you know what you’re capable of doing.

Customer Success Lesson #3: Learn To Say You’re Not Perfect

I’m definitely not the perfect example for performance at my job and I know it. Not every batter hits a homerun… sometimes you strike out.

Okay. I’m not the worst. But there are definitely days that my support conversations just don’t go like I want them to.

When I feel elated, I often wonder who I could have helped better. When you’re in the business of relationship, you’re gonna let people down. It’s important to recognize your strengths but, most importantly, to recognize that you’re gonna suck and it’s going to be difficult to admit it.

This is the reason why so many of us on the success team have our strengths and we all rely on one another to be the best foundation for Carrot and our partners and members. We make errors every day — sometimes every minute — such as misreading a name or misunderstanding a customer.

But sometimes, we make large errors.

I have missed calls with clients because a meeting ran long or I didn’t check my calendar. I have attached domains and broken domain emails because I forgot to review if someone had certain integrations.

Sites have been upgraded to include new features and all changes weren’t discussed… but reverting was impossible. There have been times when billing errors were been made on our support team and it’s never a good thing to take someone’s money.

Heck, there was even this time that I made a billing mistake.
lesson in customer success
We don’t want to be awful and we definitely want to do the best at our job that we can possibly do, but we make our mistakes. The important thing is to acknowledge your mistakes and admit them. If you can say that you’re not perfect, it opens the door for building a relationship.

The point?

You have to put yourself out there.

  • Admit when you’re wrong and move forward.
  • Stop dwelling on your mistakes.
  • Allow other team members to do the same thing.


I hope this helps.

Working on a Customer Success team’s front lines means you will have hundreds of conversations a day and you will be able to build relationships. It is a sure-fire way to get much-needed practice in both conversational and time-management skills.

It’s challenging but very rewarding to witness when a person’s dreams come to fruition — when a lead comes in on a site you helped create. Or when a house sells and the family can finally have closure. Even cooler: when a first deal is made from a site lead.

The point is, at Carrot, we all lead in our own right.

If you want to join us, then consider applying to our customer success team here; but only if you’re ready to lead. :-)


Andre likes to start her day early, before the birds wake, setting and keeping a strong momentum. An avid reader, runner, and cook. She enjoys learning, laughing, gardening, singing and dancing. She wants to help you be successful and will make sure you have fun along the way.

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