We replaced our sales team with 20 AI agents—here’s what happened | Jason Lemkin (SaaStr)

My guest is Jason Lemkin, founder of Saster and one of my favorite minds on sales and go‑to‑market, who just rebuilt his sales org around AI and came to show us what that future feels like.

Lucky to be a superfan and then to jump in on the other side.

Since our last chat, you went deep on AI for sales, so set the stage—what is Saster’s business and what changed?

Saster grew from a blog into a large community with an annual 10,000‑person event and eight‑figure revenue, and after two senior reps quit on site this year I told our part‑time Chief of AI, Amelia, we’re going all‑in on agents; we now have desks named for agents, productivity similar to the old team, and far more efficiency, but only after serious training and iteration.

So you sell sponsorships and tickets, right?

Yes—sponsorships are roughly 70 to 80K and tickets are high volume, and we run different agents for high‑end sales, lower‑priced tickets, and reactivating lapsed buyers using different vendors.

You used to have around 8 to 9 go‑to‑market folks; now it’s 1.2 humans and 20 agents—same results?

Output is about the same and scales better; I’d still hire great humans, but the mid‑pack is getting displaced while the best get superpowers.

Zooming out, how is go‑to‑market changing?

The plays still work—events, podcasts, outbound—but playbooks are broken because demand bifurcated, with AI leaders drowning in leads and everyone else chasing efficiency, and almost everyone is suddenly “in market” due to top‑down pressure to adopt AI, which makes build‑versus‑buy and ruthless prioritization the new game.

What’s the future of SDRs and AEs?

Email‑driven SDR cadences and inbound qualification should be mostly extinct within a year, while AEs keep a big slice of the job for now but must become more technical and agent‑savvy, with entry‑level rungs shrinking and value concentrating in people who can orchestrate agents and really know the product.

For hiring, I still see a lot of go‑to‑market asks—what kind of leaders win here?

Leadership is essential, but only a minority are ready to ditch old playbooks; hire folks eager to do the 2026 work, not just the 2021 motions.

If someone worries their job is at risk, how do they become part of the top 20 percent?

Pick one agentic tool for a painful process, ingest your data, train daily, QA relentlessly for 30 days, and ship it yourself; do one well, reuse your best prompt across vendors, and you’re suddenly hyper‑employable because almost nobody has actually done the hands‑on work.

Give us a quick tour of the agents and tools that mattered most.

Do not build GTM agents in‑house unless you’re truly Vercel‑level; we started with Delphi for Digital Jason, which evolved into support that actually responded instantly and even closed a sponsorship, then used Artisan for outbound reactivation and Qualified to qualify and schedule inbound, and the real unlock was vendors who gave us forward‑deployed help to train and deploy well.

You do not need massive scale—if you have a few hundred customers you probably have tens of thousands of contacts; Agentforce crushed reactivation on leads humans deprioritized, and the constraint now is orchestration time because agents never sleep and quality review is real work.

How do you keep outbound emails from being noisy and bad?

Start with your best human copy, train the agent on it, let it create variants, and lightly personalize from CRM and web behavior—well‑trained outputs are “pretty good,” easily beating mid‑tier humans, and it rarely matters whether you disclose it’s an AI if the message is useful and fast.

Do artisanal emails still win anywhere?

For a small, high‑value target list, great humans still outperform, but at any real scale humans cannot touch enough accounts and ignore mediocre leads, so AI fills the gap while tech sales remains mostly remote even though in‑person still lifts close rates.

Structure‑wise, it sounds like agents own the top of funnel and one AE closes, with Amelia overseeing quality—how important is that role?

Critical—promote an internal nerd from product, marketing, or RevOps to orchestrate ingestion, training, QA, routing, and segmentation so agents do not collide, because master‑agents that manage other agents are not ready yet and set‑and‑forget will fail.

Advice by level: what should leaders and junior reps do right now?

Leaders should personally buy and deploy an agent end‑to‑end to learn ingestion, training, and orchestration for real; junior reps should embrace the agent that fills their calendar, accept full transparency from tools that log everything, and ride the productivity jump instead of fighting it.

For startups, it sounds like hands‑on implementation is the wedge.

Yes—forward‑deployed help is the moat, and even Salesforce now leans in with FDEs whose job is to make customers successful at go‑live, often doing the heavy lift while sales shepherds procurement.

What’s truly changing versus staying the same in sales and go‑to‑market?

Support is permanently AI, classic SDR cadences and inbound qualification will fade fast, and AEs must become far more technical and efficient; field sales and AI calling are open questions, startups will push limits, and cold‑calling remains a specialized craft rather than the core of tech sales.

Anything else big you expect to shift?

Net we will need more go‑to‑market pros because winners are scaling so fast, PLG darlings are adding enterprise motion, and a new breed of high‑paid SDRs will manage fleets of agents instead of people, so master the tools now and focus on the next two to three years.

You sound energized by this wave.

It’s magical and it is more work—anyone can build real apps now, and my favorite test is to use your product in incognito, find what makes you wince, and fix that with an agent so the customer experience gets better forever.

And if teams worry about job impact?

Be honest that the best will get superpowers while roles shift, most change comes from not backfilling with humans, and if you will not embrace it you might be safer staying put than job‑hopping into the new world unprepared.

Lightning round—books, shows, products, and a motto?

Grab a few tactics from sales books but skip rigid playbooks until new ones land; Pluribus nails the coming hive‑mind moment and Salesforce is already the hub for agent data; I use Reve daily for fast, on‑brand marketing images from a simple prompt; and my motto right now is do not quit if you have happy customers—bolt on AI and sell them more because it is still early.

Okay, how many Sasters have you hosted at this point?

We’ve run meetups since early on, went big in 2015, paused in 2020, then came back as the only Bay Area event in 2021. At this point it’s about twelve in the US, seven in Europe, roughly twenty major events and three to four thousand talks if you count the smaller ones.

Across all those, what’s the one talk you still point people to?

For a mind‑reset, watch my chat with Ben Chestnut right after the Mailchimp acquisition, where he pokes holes in sacred B2B metrics and talks about building a huge, profitable business without obsessing over CAC and LTV. For GTM, I love the Rippling revenue playbook session with their CRO and Sam Blonde from Brex—two straight‑shooting CROs comparing notes on how to drive hypergrowth.

I just had McGinnis on the podcast, and you’re the ideal guest—deep experience, clear answers, and a hands‑on view of where we’re headed—so thank you and I’m excited for more.

Thanks, Len—huge fan and just grateful to be here.

Before we wrap, how can listeners be helpful to you?

Head to saastr dot ai and play with the tools we built—try the valuation calculator, the AI VC, and the rest—and send me candid but kind feedback. I’ve wanted to build for this community for a decade and I’m fired up to ship many more, because making your own tools is just fun.

So that’s saastr dot ai, right?

We’re still juggling dot ai versus dot com because of SEO, but the site looks great and works well.

It works, it’s shorter, and Jason, thanks again for being here. To everyone listening, subscribe on Apple Podcasts, Spotify, or your favorite app, drop a rating or review to help others find the show, and catch every episode at lennys podcast dot com—see you next time.