Jason + Lenny Are Back: The Real Future of AI in Sales
In early 2024, Jason and Lenny broke down sales and GTM fundamentals on Lenny's podcast. That advice still holds. But it came from a world where humans handled everything-sales, marketing, onboarding, support, and success.
They're back for the first show of 2026, and the shift is undeniable. At SaaStr, most of the go-to-market team has been replaced by AI agents-with the same revenue using 1.2 humans instead of 10. Here's what sales leaders and founders need to know now.
Top 10 Takeaways
- The math is real: SaaStr went from 8-9 human salespeople to 1.2 humans + 20 AI agents with equivalent revenue.
- Classic email SDRs are going extinct: Cadence-driven, inbox-qualifying SDR roles will be 90% displaced within 12 months.
- The $250K SDR is coming: Top reps won't send emails-they'll manage ~10 AI agents. Same title, totally different job.
- AI closed $70K and $100K deals: An AI agent sold a $70K sponsorship at 11 PM on a Saturday. Another $100K deal closed on New Year's Eve. Humans stepped in only for procurement.
- Training takes 30 days, not 30 minutes: Expect 50-60 hours of setup: upload data, answer questions, correct mistakes, iterate.
- Don't build-buy: Unless you have a motivated engineer, use existing products. The space moves too fast for DIY.
- Human oversight isn't optional: Appoint a "Chief AI Officer" type-someone quantitative who lives in dashboards.
- The plays work; the playbooks are broken: GTM fundamentals are the same. The 2019 execution playbooks aren't.
- Support is the easiest starting point: At leading companies, 50-80% of support is now AI-handled.
- 70% of AE jobs are safe (for now): Expect that to fall to 40-50% as AI expands into more of the cycle.
The SaaStr AI Experiment: What Actually Happened
This shift wasn't planned. Two sales team members quit in May 2025. Instead of rehiring, SaaStr doubled down on AI agents that were already showing promise.
Today: 20 AI agents run across workflows, managed by one full-time AE and ~20% of a "Chief AI Officer's" time. Low-ticket deals run fully through AI. High-end sponsorships bring in a human near negotiation and procurement.
The surprise: lead response and qualification improved. Agents reply at 11 PM on Saturdays. They don't get tired. They don't cherry-pick. They follow up on every single opportunity.
Going Extinct (next 12 months)
- SDRs who send templated emails and qualify inbound
- BDRs running classic cadence-based outbound
- Any role where the main function is routing information
Surviving (for now)
- AEs handling complex negotiation and procurement
- Enterprise sales with real relationship depth
- High-dollar deals where heavy personalization pays off
Thriving
- Sales pros who manage and train AI agents
- Data-driven demand gen marketers
- Forward-deployed engineers ensuring AI product success
- Anyone willing to put in 50-60 hours to learn to work with AI
The Practical Playbook
Start with Support. Most teams can't run true 24/7. AI can. It's the lowest-risk, highest-impact wedge into your org.
How to train agents well:
- Start with your best-performing email copy (not the average stuff).
- Upload it as your baseline templates.
- Connect data sources (CRM, billing, product usage) for personalization.
- Run constant A/B tests-AI is great at generating variants.
- Review outputs obsessively for the first 30 days.
- Correct mistakes explicitly-treat it like you would a new hire.
The "Incognito Mode Test": Create a fresh Gmail. Sign up for your own product. Experience support, sales, and onboarding like a prospect. The gaps you find are your AI opportunities.
Vendor tip: Choose vendors that offer real implementation help. Hands-on support separates winners from the also-rans.
The Uncomfortable Truth About Jobs
AI is squeezing the middle. Not the best reps. Not (yet) leadership. The midpack is being replaced by agents that don't miss follow-ups and don't get sloppy.
This isn't mass layoffs in headlines. It's silent backfilling. Jobs that would have been posted are going to AI agents instead.
If you're in sales, act now:
- Pick one AI tool and deploy it in your workflow this month.
- Train it yourself. Log the 50-60 hours. Become the in-house expert.
- Learn to manage 5-10 agents like a mini team-reporting, QA, iteration.
If you want structured upskilling, see curated AI programs by job role here: Complete AI Training.
Top Mistakes Founders Make With AI Agents in Sales
- Expecting plug-and-play magic-this is a 30-day ramp with real effort.
- Building instead of buying without the engineering capacity or appetite.
- No human oversight-"set and forget" leads to public mistakes at scale.
- Training on mediocre content-feed it your A-player's best work.
- Skipping segmentation-agents will collide and spam the same accounts.
- Underestimating change fatigue-rolling out 20 agents at once burns teams.
- Waiting for perfection-tools improve monthly; late starters fall behind.
- Ignoring the human handoff-define when and how AEs step in.
- Assuming "people person" skills are enough-add genuine strategic value.
- Not testing like a customer-use the incognito test weekly.
30-Day Starter Plan
- Day 1-2: Run the incognito test. Document every friction point.
- Day 3-5: Pick one support use case and one SDR use case to automate.
- Day 6-7: Choose a vendor. Confirm implementation support and data security.
- Day 8-10: Gather best-performing emails, call scripts, FAQs, and objection handles.
- Day 11-14: Connect CRM and data sources. Define segments and routing rules.
- Day 15-18: Launch 2-3 agents with narrow scopes. Set daily QA checkpoints.
- Day 19-22: A/B test subject lines, CTAs, and qualification paths.
- Day 23-25: Build the human handoff process and SLAs.
- Day 26-28: Expand to a second segment or channel if metrics are stable.
- Day 29-30: Document learnings. Lock in dashboards. Plan the next 60 days.
Final Word
These are magical, uncomfortable times. The plays are the same: find prospects, qualify, help them buy. The old playbooks are finished.
The people who get very good with AI will be more employable than ever. The clock is ticking-choose to be one of them.
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