Allison Pickens' Podcast

Hosted by Allison Pickens

Business Entrepreneurship

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Jun 2025

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Patterns and prophets, in SaaS and Web3 allisonpickens.substack.com

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June 25, 202539 min

Outselling with AI: How Founders Are Scaling Without a Sales Team

The world of AI tools for GTM is crowded, to say the least. It seems like there are point solutions for everything — an AI agentic solution for cold-calling, another for enrichment, another for research, another for upsell, another for giving executives visibility. For investors and revenue leaders alike, it can be exhausting to parse through all the options.The founders of Clarify had a much bigger vision from the beginning, which is why I was drawn to them and decided to invest in both their Seed and Series A rounds. In this conversation with co-founders Patrick Thompson and Austin Hay, I unpack their idea of “autonomous go-to-market” and their vision for what “excellence” looks like for founder-led sales and early-stage revenue teams in the genAI era. We tackle questions such as:* What should founders expect from their CRM?* What does founder-led sales look like nowadays?* What should your GTM tech stack look like?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

December 10, 202427 min

Mastering Company Alignment: How to Focus Time, Cut Waste, and Achieve Strategic Goals

CEOs know that time is their most valuable resource, but they often sense that their teams spend time on things that don't matter or are even counterproductive. This misalignment between company priorities and how people actually spend their time is a massive problem for most organizations. The symptoms of this problem include:* A terse exchange between executives after one asks the other for resources to help with a project.* A team fails to hit their metric because they were derailed by an ask from another team.* A team fails to hit their metric because another team didn't deliver.* A team member quits because they spent many weeks on a project that was ultimately shuttered, to their surprise.* A customer hears different things from different people at your company.These situations lead employees to ask, "Does my work matter at all?" Customers wonder, "Does this company have its act together?" Executives wonder, "Do I really want to work at a company where I have to constantly battle my peers?” And the CEO wonders, "Why are we burning so much money and have so little to show for it?"I sat down with Alex Terrien, the COO and Co-Founder of Parable (one of my portfolio companies) to discuss the goal of alignment. The bottom line: Alignment has been an elusive goal for most companies to date, but with advanced AI, we can achieve a new standard. You can listen to the audio or read the refined 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

January 16, 202426 min

Modal's CEO: How to Maximize Developer Productivity

The CEO of Modal, Erik Bernhardsson, is a super well regarded former CTO. In this conversation, we spoke about his best practices for driving developer productivity, a topic that he has thought a *great* deal about, as you will soon see. We covered:* What is the secret to developer productivity?* What are the common mistakes that CTOs make?* How do the best practices change over the course of a startup’s life?* How did these best practices inform the way he developed Modal to enhance the productivity of data teams?It’s always fun to host a leader who has reflected so deeply. You’ll find some useful frameworks in this conversation. Feel free to listen to the audio version or else read the lightly edited transcript below. Let’s dive in!If you’d like to hear from more CEOs about how to run AI companies, subscribe for free here. 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

January 11, 202449 min

Growth Mindset, Growth Efficiency, and Growth in Customer Success

Often I’m interviewing other company builders that I admire, but it’s always energizing to be interviewed as well. I participated in a fireside chat with Carolyn Fikke at Golden Seeds, an early-stage investment firm focused on women-led businesses. I’m re-publishing our conversation here. We covered a range of topics, including:* How does AI affect CS?* What are the 7 fundamental attributes of companies with high growth efficiency (and talent efficiency)?* What are the 4 dimensions on which we can coach our teams (and grow ourselves)?This was a fun conversation! You can listen to the audio version or else read the lightly edited transcript below.Subscribe (for free!) to listen to other fun conversations about scaling AI and SaaS companies. 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

December 12, 202339 min

Go-to-Market for Technical Founders

I had a great time participating in a panel on go-to-market strategy for open source companies at Kubecon StartupFest, hosted by Dave Zilberman at Norwest, Erica Brescia at Redpoint, and Jesse Robins at Heavybit. I represented the “sales” perspective, alongside “community whisperer” Jono Bacon at Community Leadership Core and “wunderkind marketer” Adam Frankl at Alchemist Accelerator and Dev Angels. I’m republishing our discussion here. We covered topics such as:* If you’re a technical founder, how do you build your skills in selling?* If you’re an introvert, how do you become your company’s Chief Evangelist?* What is the value of founder-led selling, and when does it make sense to hire an AE? And a VP Sales?* How do you determine your pricing and packaging strategy early on?…and many other questions.You can listen to the conversation or else read the lightly edited transcript below. Enjoy!If you’d like to learn about go-to-market strategies for AI and SaaS companies, subscribe for free! 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

November 21, 202325 min

AI in Customer Success

Right now it’s hard not to read about anything except OpenAI’s rapidly evolving situation. At the same time, even if the future of OpenAI’s technology and ecosystem is uncertain, there is certainly a wave in AI that is unlikely to be deterred for long. Given this, I’m going ahead and publishing this post on AI in Customer Success, which is as relevant today as it was when I queued up this post last week. With that said, let’s dive in!***AI is quickly transforming many professions, including the role of Customer Success. I was psyched to join a panel on this topic at Matik’s recent AI+CS Summit and am republishing the conversation here. The panel was moderated by Nik Mijic and included Zeya Yang at a16z, Grace Ge at Menlo Ventures, and John Gleeson from Success Venture Partners.We covered topics such as:* What types of AI companies are attracting investors right now?* How is AI being adopted within tech companies?* How should CS teams be using AI?You can listen to the conversation or else read the lightly edited transcript. 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

October 17, 202317 min

GTM Strategy for GenAI Companies

Lightning-fast activation. A surge in top-of funnel. Churn due to AI tourism. Lower hurdles for monetization. Fast-changing market.Your go-to-market can change massively when you incorporate LLMs into your product. The team at Gamma certainly found this to be true. Gamma was founded as a new medium to replace the slide deck, well before the launch of ChatGPT, then experienced a huge uplift in their business after they started deploying generative AI. Their numbers changed, but so did the fundamentals of their go-to-market.I sat down with Gamma cofounder Jon Noronha to discuss GTM topics like:* How did they expect LLMs would change their GTM, and what actually changed?* What user metrics are they focused on?* How have they handled AI tourism?* What is their strategy for monetization?You can listen to the conversation or else read the lightly edited transcript below. Enjoy!If you’d like to learn from more founders about how to scale generative AI companies, subscribe for free! 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

October 10, 202325 min

AI Ops: A New Startup Arena

New tech shifts often precipitate the rise of new best practices and new roles. I was excited to speak with Sarmad Qadri, CEO and founder at LastMileAI, about the emerging category of AI Ops. We covered topics such as:* What have been the primary gaps in workflow for technical people trying to use AI?* What are the software categories within AI Ops?* In which categories do startups have an advantage versus older companies that have operated in adjacent categories?You can listen to the conversation or else read the lightly edited transcript below. Enjoy!If you’d like to learn from more founders about how to scale generative AI companies, subscribe for free! 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

September 19, 202325 min

How to Drive User Referrals - Your Best Growth Channel

Word of mouth is crucial to a company’s growth. But historically, B2B companies haven’t been able to track, measure, or influence word-of-mouth systematically. Meanwhile, our B2C counterparts have benefited from referrer codes and trackable invitations for over a decade!Stefan Bader, Founder/CEO at Cello, figured out a fintech solution to enable B2B companies to incentivize referrals. So he knows more about “user-led growth” than anyone else. After investing in his seed round, I was excited to dive deep into this new functional discipline that growth marketers everywhere should be mastering.We discussed:* How does user-led growth relate to product-led growth?* What are the metrics for best-in-class user-led growth?* What growth marketing tactics can multiply referrals?…and many other topics, as we unpacked this new category.You can listen to the conversation or else read the lightly edited transcript. 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

September 13, 202325 min

Product Marketers: The New Hub of Marketing

There’s a big opportunity for category creation when a tectonic shift has elevated the importance of a particular role.This was exactly the opportunity we had at Gainsight: the explosion of the SaaS ecosystem propelled the population of Customer Success Managers, who were now essential for driving Net Dollar Retention at most SaaS companies.Today, the advent of LLMs has increased the focus on content, thereby positioning Product Marketers, the owners of that content, as the strategic drivers of marketing campaigns.Derek Osgood, the CEO and Founder of Ignition, believes that Product Marketing is the new hub of Marketing teams. In this episode, we discussed:* Why have so few big marketing tech companies been created in recent years?* How has AI changed the way marketing teams operate, and therefore also changed the best-in-class marketing tech stack?* What are the new best practices for Product Marketing teams?You can listen to the conversation or else read the lightly edited transcript below. 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