Bots, AI and The Next Customer Communication Platform

Recently my company Drift announced Drift 2.0 and I want to take a quick second to share a little more about what we’re up to…

Over the last few months, nearly 4,000 businesses have used Drift to talk to their customers (and people who are just visiting their websites).

But that was just part one. Our mission at Drift is to help businesses grow by delivering a better, personal experience across every conversation your customers have with your company and we’re just getting started.

With the launch of Drift 2.0 today, we're bringing the power of Artificial Intelligence to the most important part of your business: the relationships you have with your customers. And the response was amazing -- we were the number one product for the day on Product Hunt.


With Drift 2.0, we can finally help the largest companies around the world deliver the highly personal experience that modern customers demand.

This is where Artificial Intelligence (AI) comes in.

And we know "artificial" and "personal" together might sound funny, but here's how it can help make things better. Modern customers expect a highly personal experience. They want every interaction with your business to feel like a one to one conversation.

Drift can understand all of the conversations your customers are having with your company, and help get the right message to the right person at the right time.

With the help of machine learning, your business will be able to deliver a personal customer experience at scale -- that means no more worrying about sales reps wasting time with support questions, or angry customers going unanswered for days.

But we believe that we’re in the middle of a big shift in marketing and we need your help. We believe that helping is the new selling, and that customer experience is the new marketing.So come help us transform the way that the world does business :)

Help make business personal again with Drift.


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This Is Why I Never Hire Product Managers

I’ve spent 20 years in my career building and leading product teams. But I have a contrarian approach when it comes to hiring product managers. For the first time I’m sharing my hiring checklist the we use at Drift here: Click here to get access to it.

When I first got into tech and startups, the most valuable and sought after asset was experience. And when it came to product management, every product manager wanted to leave their current job to go out and get a business degree.

Business skills were super valuable, while product management sat at the bottom of the totem pole in most organizations. Because of that, a lot of people were trying to escape from product management.

Today, the power balance has completely shifted. How often do you seen startups on Product Hunt or coming out of YC boasting that they have “business-driven co-founders.” Never.

That’s because today, product and design are the differentiators for most modern companies — not business. As a result, having business experience has gone out of style, and instead, all those “business” types want to become product managers.

This has been obvious for a while now, but it really hit me a few weeks ago while I was speaking at Harvard Business School.

Back in the day, all of the product managers at my companies wanted to leave to go get their MBA. Today, everyone wants to go to business school to leave and become a product manager.

Note: This post originally appeared on my Medium channel.

“What do you look for when hiring a product manager?” Is one of the questions I get the most, so I thought I’d share my process for hiring product managers:

I try to never hire someone who has been a product manager before.

This might seem counterintuitive — especially considering that hiring is one of the hardest parts of a startup, but stick with me. Here’s why:

Experience rarely matters.

I’ve never seen a correlation with past experience and future success when it comes to product managers.


Our world — especially in the technology space — has changed and continues to change at a rapidly increasing rate.

We value people who are learning machines and are highly adaptable (antifragile) over people who only bring experience.

There’s very little overlap.

Product management is a role that is very unique to a specific company. If you meet five product managers from five different companies, then you’ve truly met five different product managers. There will be very little overlap. The PM role is different at every company. Sometimes it’s a true product owner. Sometimes they are really just project managers. Sometimes they are product marketers. Sometimes they are a little of each.

Sometimes they report to a VP of Product. Sometimes they report to a VP of Engineering. Sometimes to the CTO (outside of core engineering which the VP of Engineering runs). Sometimes in small companies they work directly for the CEO. Sometimes they report to Marketing — and I’ve even seen a few PMs that report into Sales.

See a problem here? Throughout my career I’ve seen countless definitions for what a PM is, what they do and who they report into (and I’m sure you’ve seen the same thing, just think about the PMs that you know and what they do).

Our special sauce has always been product.

The companies that I’ve started have all been product-driven companies. Product has been our special sauce.

And if your special sauce is product (like it is for most modern companies) then you’re better off growing your product team from within. Hire from other groups. Hire the people that already share your “DNA.”

Why? Because you have a playbook that is your competitive advantage.

Even if you can find a PM externally who happens to meet your definition of a great PM, the experience they bring is something that you’ll most likely want to retrain/untrain them of. You want them to use your special sauce, your differentiator.

Think about what your special sauce is and hire experienced people with playbooks in areas that aren’t your special sauce area. For me that’s been in HR, Sales and Finance. Those are the areas where I really value the experience that an outsider can bring. And this goes for any area, not only Product. Say your special sauce is Marketing. Then you probably should grow your marketing talent vs. acquire it.

Now, all of that said, there are a set of patterns and heuristics that we look for specifically when hiring product managers. Here are the things that I’ve found to be helpful.

What I Look For When Hiring Product Managers

Here’s the quick hit list of things to think about when talking to potential PMs for your startup.

Are they truly a product junkie? Do they geek out on new products? Is Product Hunt one of the first sites they read every day? Are they the first to be playing around with new products? Are they telling me about some product I don’t know about? Do they know about more products than me? And do they have passion around this. I love to have candidates show me their phone or desktop to see which apps they are using, which new products they are testing. It’s easy to tell if someone genuinely geeks out over new products. This one’s tough to fake.

Are they curious? Look for the curious ones. Are the settling for yes or questioning for why? Do they want to learn from others? Too many people try to re-invent the wheel instead of finding familiar patterns from other companies and innovating.

How would they make existing products better? What ideas do they have for products? How would they make them better? Pick a product on the spot and ask them to show you how they use it, what they’d change and how they would improve it.

How do they work everyday? Find out what they use from a process standpoint. Do they use Trello? Evernote? ProdPad? The best PM’s are always trying new things and finding ways to improve when it comes to process and organization.

Do they have a customer-driven mindset? It’s the PMs job to understand the customer better than nearly everyone else. PMs should be talking to the customer the most at your company other than support (most likely). Do they live and breathe customers? Can they help engineering and design get closer to the customer? This is the most glamorous part of being a PM. The point of business is to sustain and generate customers, and in the SaaS world, the PM is the closest person to that customer. The right fit for a PM role gets excited about this.

Two things that don’t matter:

  1. Technical ability. You do not need to be very technical. That is a common misconception.
  2. Dashboards and strategy. Someone who is more interested in being a BD or strategy person will be the wrong fit. This role should be customer-driven first. Product management is not about dashboards, slide decks and Excel. Looking at data all day is not what being a PM is about. Keep an eye out for candidates that want these things.

At the end of the day, here’s what matters the most:

Think about your secret sauce, especially when it comes to hiring PMs. If it’s product, then look outside the box to find PM’s that you can mold and grow.

PS. You can get access to our hiring checklist at Drift right here.

Listen to @DaveGerhardt and I discuss this topic on the latest episode of Seeking Wisdom.

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The Books Every Startup CEO Should Read

Note: This post originally appeared on my Medium channel.

Since I’m always talking about the books I’ve read, I often get asked for book recommendations, especially by fellow Startup founders.

This morning Nick Rellas the CEO of Drizly asked me for a list of must-readbooks, so I quickly put together this list.

I think every Startup CEO & Founder would benefit from reading the books on this list.

Sorted by books I’ve re-read the most:

  • The Hard Thing About Hard Things — The only “real” business book. This book captures what it is like leading a startup.
  • Made in America — The story of how Sam Walton created Wal-Mart and became the richest man in the world. I have stolen many concepts from this book including the concept of Servant Leadership. Read 3x.
  • Seeking Wisdom — I can’t remember how I first found this book years ago, but it’s been on my nightstand ever since. I continuously read this book finding new gems each time.
  • Zingerman’s Guide to Giving Great Service — If you care about creating agreat customer experience read this book.
  • Managing Oneself — buy this tiny book by Peter Drucker and re-read it every five years.
  • Behind the Cloud — The story of Salesforce from its founder & CEO, Marc Benioff.
  • Let My People Go Surfing — The story of the founding of Patagonia and more importantly how to build a company with strong values.
  • Positioning: The Battle for Your Mind — This and Influence: The Psychology of Persuasion are the best books on Marketing. These books will teach you why you buy the things you do.
  • Meditations — So deep you need to re-read this book every few years.
  • Practicing The Power of Now — The best way I’ve found to deal with the daily anxiety of running a business is to focus on the “Now.” Start practicing with Tolle’s book.
  • Influence: The Psychology of Persuasion — I’m reading this book for the 3rd time now. The best book there is to understand the cognitive biases we all use to make decisions.
  • Entreleadership — If you want to learn how to work on your business, not in it, read this.
  • Setting the Table — I’m obsessed with great customer service. Nobody knows delivering great service better than Danny Meyer, one of America’s leading restauranteurs.
  • The Big Moo — So many great Seth Godin books to read, I’ve read all of them. I always come back to two books, Purple Cow and The Big Moo, a companion book to the Purple Cow.
  • Re-Imagine! — Too many great Tom Peters books, start with this one.
  • High Output Management — The book that started the recent OKR trend used by Google and many other companies to manage priorities.
  • Predictable Revenue — This book is a great guide to running a sales team from an early sales leader. I had a hard time choosing between this book and The Sales Acceleration Formula (read both).


Find out what I’m learning building my 5th startup, Drift, by subscribing to my free newsletter.


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