We’re nine months out from the release of ChatGPT, which awakened the broader public to the possibilities of generative AI. After the initial hype, what are the areas in which excitement about generative AI is warranted?

I’m excited to publish a panel discussion on this topic that I participated in. Matt Dupree, the CEO of ATLAS, organized and moderated the conversation. Jonathan Pedoeem, CEO of PromptLayer, and Vijay Umapathy, Sr. Director of Product at Heap, were also panelists.

We discussed:

* What exactly is the value of ChatGPT?

* What are some examples of where generative AI has failed to live up to initial expectations?

* What are some emerging categories of generative AI, where it’s proving to be truly useful?

You can listen to the conversation or else read the lightly edited transcript below. Enjoy!

Announcements

If you’re excited about a new category of generative AI, I’d love to hear about it. Feel free to respond to this email newsletter or message me on LinkedIn.

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I’ve always appreciated systems-based approaches to solving problems, because they facilitate scaling. More specifically, creating thoughtful processes can enable high Growth Endurance – the subject of this Substack series – which means sustaining 70-100% growth rates even once you’re approaching $100M in ARR.

Shishir Mehrotra, Co-Founder and CEO at Coda, has spoken and written extensively about company “rituals.” I was curious to hear his take on how strong rituals can help companies grow fast for many years in a row — and I’m glad I did, because this conversation was jam-packed with actionable suggestions. We covered questions such as:

* What rituals can help companies tackle new revenue streams — new product launches, new geographies, or acquisitions?

* How should you adapt your rituals as you grow?

* If you’re looking to “get in shape” with respect to rituals, where should you start?

You can listen to the podcast or else read the lightly edited transcript of the conversation. Let's dive in!

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit allisonpickens.substack.com

Founders often ask me how to up-level their leadership teams. Their questions might include:

* My director of [function X] was one of our first employees. How do I help them grow into a VP?

* How do I know if they are actually ready to be an executive?

* How do I set expectations with them?

I had these questions and more when we were experiencing hypergrowth at Gainsight. I didn’t want to replace my direct reports if I could help it. I wanted to help them grow their skills as fast as the company’s requirements were changing. So I teamed up with a stellar executive coach to create a framework for what it means to be a strong executive. 

David Lesser is a leadership coach, but more than that, he’s a philosophical guru. I worked with him for several years at Gainsight. His focus is on helping CEOs and executives with self-actualization, which he strongly believes makes them better leaders. 

In this podcast, David and I discussed:

* Why is it important to set expectations for executives, apart from the targets on your metrics dashboard or the requirements in their job description?

* What are the 4 competencies that executives should demonstrate?

* Why is there no universal definition of a stellar VP of Sales?

You can listen to the podcast or else read the lightly edited transcript of the conversation. If you scroll way to the bottom of this post, you’ll see the actual guide that I used for coaching my executives at Gainsight.

I always love conversations with David, and you’ll see why once you listen to this episode. Enjoy!

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit allisonpickens.substack.com

In this episode, the Revenue Builders podcast interviewed me about the latest trends in customer success. I’m republishing this extensive conversation here. We covered a ton of topics, including:

* What is the impact of generative AI on customer success?

* Why has time-to-value improved for B2B products?

* How should sales relate to customer success?

…and many more questions.

You can listen to it or read the lightly edited transcript. Enjoy!

If you enjoy this conversation, share it with your favorite founder or customer success leader!

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit allisonpickens.substack.com

I’m excited to continue the series on Growth Endurance — how to sustain high growth rates for a long time, in the face of macro headwinds. In this episode, I traded notes with Steve Sloan about our experiences scaling companies through all stages. Steve is now the CEO of Contentful — #38 on the Forbes Cloud 100 list, with over 800 employees. Steve was previously Chief Producer Officer at SendGrid, growing the company from an early stage through IPO and through its subsequent $2B acquisition by Twilio, where he became Chief Product and Marketing Officer.

Steve and I discussed how to run a company differently at $10M, $30M, and $100M in ARR. We covered topics such as:

* How do you handle malaise on the sales team when you have to increase quotas, and reps can no longer rely exclusively on the heavy inbound pipeline from the early days?

* What should you expect of executives as you grow larger, and how does the executive role differ from a functional leadership role?

* Why is your pricing model so important, and what does it take to get it right?

You can listen to the podcast or else read the lightly edited transcript of the conversation below. Let's dive in!

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit allisonpickens.substack.com

Every time your users post a product review with a photo or video, they’re contributing to the vast treasure trove of user-generated content. But companies have barely scratched the surface in leveraging that visual content for marketing purposes. Why aren’t we mining the data across those images and videos?

In my latest podcast episode, I discuss how to bring structure to this kind of unstructured data, in a conversation with Cody Coleman, CEO of Coactive. Coactive recently announced its combined Series A and Seed funding from a16z, Bessemer Venture Partners, and others.

* What are the best practices for data teams to work with visual data?

* What mistakes are data teams making?

* Is this kind of unstructured data a “data problem” or a “marketing problem”?

You can listen to the podcast or read the lightly edited transcript. Let’s dive in!

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit allisonpickens.substack.com

The application layer of generative AI has become very crowded. How can your startup stand out from the pack?

Jasper is a generative AI company that has grown at an astounding pace. When I invested in the fall of 2021, CEO Dave Rogenmoser and his team of 9 people had grown the company from zero to $40M in ARR in 9 months.

Although they had the advantage of being among the first to market, they’ve also deftly and steadily built walls around their business, as a flock of talented folks start new generative AI companies.

I sat down with Jasper’s CMO Meghan Keaney Anderson to discuss:

* What are the latest trends in generative AI?

* What has driven Jasper’s ongoing success?

* What can other generative AI companies learn from Jasper’s playbook?

You can listen to the podcast or read the lightly edited transcript below. Let’s dive in!

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit allisonpickens.substack.com

Generative AI has sparked our imaginations. It also has terrified us. Bing’s chatbot declaring its love for a NYTimes columnist, CNET’s saga with AI-generated content, and many other incidents have shown that AI can generate horrific outcomes. Moreover, the nature of the adverse outcome can be totally unpredictable.

Randol Aikin helped build safety systems for self-driving cars at Uber and elsewhere. He was particularly affected by a fatality caused by a self-driving car and began to envision how he could prevent other types of generative AI from generating catastrophes like this. That’s now the mission of his new startup: to create guardrails for generative AI more broadly.

In this conversation, we discussed:

* How are safety systems for self-driving cars instructive for preventing adverse outcomes from generative AI?

* What are some examples of adverse outcomes that would be hard to predict?

* What are best practices for avoiding them?

* What should be the role of boards in monitoring generative AI used by their companies?

You can listen to the podcast or read the lightly edited transcript. Let’s dive in!

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit allisonpickens.substack.com

Strategic planning is a formidable task. It’s downright daunting in the current macroeconomic climate. How can you say with confidence, “Here’s how we’re going to grow from $X million to $2X or $3X million in ARR”?

This question was at the heart of my conversation with Marcus Bragg, COO at Netlify, which was named to the Forbes Cloud 100 list of the world’s top private cloud companies. In this discussion, we covered questions such as:

* How do you align with your board on a revenue plan?

* How do you incorporate riskier bets into the plan — especially when the macro-environment presents more risk?

* How do you motivate your team members to pursue moonshots while also not making them feel like they’re going to get fired if the experiment fails?

You can listen to the podcast or read the lightly edited transcript. Let’s dive in!

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit allisonpickens.substack.com

This conversation was a real treat for me. Nick Mehta, CEO of Gainsight, and I worked together for 6 years, building the company from $1M to $85M in ARR while I was there. One repeat topic in our exec team and board meetings was, “How large is our market, and how fast is it growing?” While it’s standard to have back-of-the-envelope math on your market size in your Seed and Series A pitch deck, the reality is that market sizing is much more complex than that when you’re actually scaling your business. And knowing the size and growth rate of your market is critical to sustaining high growth rates for your company.

In this conversation, Nick and I discussed questions like:

* How can you track whether customers are truly ready to buy — i.e. are “in market” — so that you’re not wasting your time?

* What do you do if your market isn’t growing fast enough right now?

* How do you adapt your messaging to the current macro climate?

You can listen to the podcast or else read the lightly edited transcript of the conversation. Let's dive in!

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit allisonpickens.substack.com