SaaStr 840: From 1 Agent to 20+: The Reality of Managing Multiple AI Agents Across Your GTM with SaaStr's CEO and CAIO

SaaStr 840: From 1 Agent to 20+: The Reality of Managing Multiple AI Agents Across Your GTM with SaaStr's CEO and CAIO

Author: SaaStr February 4, 2026 Duration: 1:03:23

SaaStr 840: From 1 Agent to 20+: The Reality of Managing Multiple AI Agents Across Your GTM with SaaStr's CEO and CAIO

Eight months and 20+ AI agents later, what does managing a multi-agent GTM stack actually look like day to day?

SaaStr's CEO and Founder, Jason Lemkin, and SaaStr's Chief AI Officer, Amelia Lerutte, get candid about what's working, and what's not.

$4.8M in additional pipeline later, AI agents deployed across Go To Market have helped deal volume doubled and win rates double. But here's what nobody talks about on LinkedIn: the 15-20 hours per week each spent maintaining agents, the messy flows holding it all together, and why you still can't outrun your own AI.

They cover the 90/10 build vs. buy rule, why hyper-segmentation is the key to AI SDR success, what to demand from vendors before signing, and why bad context will always produce bad emails, whether a human or an AI writes them. Plus, they walkthrough how they built SaaStr's custom AI VP of Marketing agent to plan and execute every campaign for the year, grounded entirely in data.

If you've deployed your first agent and are thinking about what comes next, or you're skeptical the whole thing works at all, this one's for you.

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This episode is Sponsored in part by HappyFox:

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Hey everybody, the biggest B2B + AI event of the year will be back - SaaStr AI in the SF Bay Area, aka the SaaStr Annual, will be back in May 2026. 

With 68% VP-level and above, 36% CEOs and founders and a growing 25% AI-first professional, this is the very best of the best S-tier attendees and decision makers that come to SaaStr each year.  

But here's the reality, folks: the longer you wait, the higher ticket prices can get. Early bird tickets are available now, but once they're gone, you'll pay hundreds more so don't wait. 

Lock in your spot today by going to podcast.saastrannual.com to get my exclusive discount SaaStr AI SF 2026. We'll see you there.


Tune into The Official SaaStr Podcast: SaaS | Founders | Investors for direct conversations with the people building and funding the software-as-a-service industry. This isn't about abstract theory; it's the practical, often hard-won wisdom from prominent founders and seasoned investors who have navigated the path themselves. Each episode digs into the specific mechanics of scaling a SaaS business, focusing on the critical journey from zero to one hundred million dollars in annual recurring revenue. You'll hear founders break down what actually worked when it came to hiring key talent, entering new markets, and managing the immense pressure of hyper-growth. From the investor side, the discussions reveal how top venture capitalists evaluate potential, what metrics truly matter beyond the pitch deck, and their perspectives on sustainable company culture. Hosted by SaaStr, this podcast serves as an ongoing masterclass for operators and entrepreneurs who prefer learning through candid stories and detailed strategies rather than generic advice. The dialogue is always grounded in the fierce realities of the competitive tech landscape, making every interview a source of actionable insights you can apply to your own challenges.
Author: Language: English Episodes: 100

The Official SaaStr Podcast: SaaS | Founders | Investors
Podcast Episodes
SaaStr 850: The Agents, Episode 1: Who Maintains All This? [not-audio_url] [/not-audio_url]

Duration: 1:08:06
SaaStr 850: The Agents, Episode 1: Who Maintains All This? Welcome to The Agents, a new weekly series where Amelia Lerutte, Chief AI Officer at SaaStr, and Jason Lemkin, Founder and CEO of SaaStr, pull back the curtain o…