Allison Pickens' Podcast

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 big...

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 res...

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...

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...

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 Angel...

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 las...

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 the...

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 ad...

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 kno...

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 co...

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 o...

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...

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...

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...

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...

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 unstructure...

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...

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 elsewhe...

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 d...

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...

As part of my Substack series on Growth Endurance, I wanted to speak with the most successful late-stage SaaS companies out there. ServiceTitan is #7 on the Forbes Cloud 100 list of the world’s top private cloud companies. So I was psyched to sit down with CEO Ara Mahdessian and learn how he has been able to grow his company so fast for so long. This conversation is super relevant to any CEO or ot...

At the start of a new year, many people are thinking about how they might grow in their careers in 2023. Employers need to stay ahead of those aspirations, even with the prospect of a more significant economic downturn. Employers must also adapt to employees’ changing expectations about career growth, resulting from the shift to remote work, social justice movements, and the talent shortage. I’m r...

Many startups are aspiring to “grow into their valuations” from 2021. For most of them, this will take a couple of years, at minimum. Even once they reach that target revenue level, these startups will need to show that at the end of that period, they can continue to grow fast — since their valuation presumed they would be able to sustain high growth rates into the future. Mary D’Onofrio , a partn...

This is the first post in a series on the topic of Growth Endurance — fast growth, many years in a row. We’re accustomed to hearing about startups that have tripled, quadrupled, quintupled, or grown even faster in the early stages. But once you’ve reached the tens of millions of ARR, it’s very hard to grow fast. That’s why very few companies have reached $100M in ARR, and why even fewer continue t...

Leaders are accustomed to having control over information: who sees it, how much is shared, and when. Arguably, an important purpose of leadership is to explain context to people in a narrative form. But there are major trends in our society that run counter to this idea. For example, there is a movement to make data on employee compensation more accessible. Some people believe that governments sh...