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2026 Will Be a World of PLG+AI. PLG plus AI Sales Reps. We Have No Choice.

By Jason Lemkin
Wednesday, April 30, 2025 | Artificial Intelligence (AI), SaaStr.Ai

For some, PLG was an expansion, adding new lower-end customers (HubSpot + Atlassian). For others, it was the core, and just an evolution of freemium, done better (Canva + Notion), where later a sales team would be added.

So for many years, so many B2B founders wanted to be “more PLG” or “add a PLG motion”. They really wanted though was to add a better self-serve product with a more viral element. PLG was a great way to describe the next evolution of self-serve + viral:

HubSpot added self-serve, it worked great
Atlassian added self-serve, it worked
Canva and Figma and other B2B leaders perfected PLG motions

For many next-generation AI leaders, PLG is core. ChatGPT, Windsurf, etc. all at their core have PLG motions, often with large enterprise teams backing up the bigger deals.

PLG + AI

Apply to our VIP Summits at SaaStr Annual

Hey SaaStr Community,

SaaStr Annual is less than < 20 DAYS AWAY.

Join us at the SaaStr Annual on May 13, 14 and 15 for the world's largest SaaS + AI event of the year.

We'll have over 10,000 fellow SaaS professionals, giving you the perfect opportunity to connect face-to-face with your team, customers, investors and partners.

Plus our closed-door VIP Summits are back!!

CRO + CEO exclusive poker night on Wednesday, May 14 - Join the party with 100 of the best CROs and 100 of the top CEOs in the ‘biz right at SaaStr Annual.
Chief Customer Officer Summit at SaaStr Annual. This special collaboration between the SF Customer Success Meetup and SaaStr Annual. The Chief Customer Officer Meetup at SaaStr Annual will feature a day of invite-only content and networking for leaders and executives in Customer Success on Wednesday, May 14th.
Join us for the official Chief Finance Officer (CFO) Summit at SaaStr Annual. The CFO Summit at SaaStr Annual will feature an afternoon of invite-only content and networking for leaders and executives in Finance only on Tuesday, May 13.
SaaStr Annual CMO Brunch. The Chief Marketing Officer Summit at SaaStr Annual will feature a half-day of invite-only content and networking for leaders and executives in Marketing only.

SEE YOU THERE

Our SaaStr AI Has Done 139,156 Conversations On Its Own Already. And They Are Really, Really Good. Don’t Fall Behind.

By Jason Lemkin
Tuesday, April 29, 2025 | Q&A

Our SaaStr AI Has Done 139,156 Conversations On Its Own Already. And They Are Really, Really Good. Don’t Fall Behind.

So SaaStr is a 5 person entity. Just 5 of us, but we do a lot. A lot. And yes, there are agencies and contractors that help us (bless them), but the full-time team is just 5.

Before AI, we maybe could respond to a handful of email-based issues, and a few chats. And we could not provide any direct 1-on-1 advice.

Oh so much has changed in just a month or so. Our AI has now handled 139,156 conversations for us. And most of them are epically good.

Now our AI can:

Advise founders on who to hire
Review VC pitch decks
Review board materials
Help you pick the right SaaS vendor
Help you work through slowing growth
Answer ticket questions for SaaStr Annual better than any human
Help folks that want to volunteer for SaaStr Annual figure out how
Manage 100s of speaker submissions
Help sponsors pick the right sponsorship for them, without bias
Answer 100s of nitty gritty sponsorship questions

Before, we had a pre-AI intercom chat that we answered maybe once a week. Now we can do 139,156 conversations a month with AI. And they are really, really good.

SAASTR AI

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Dear SaaStr: What Should I Do in a Sales Audit?

By Jason Lemkin
Wendesday, April 30, 2025 | Q&A

A sales audit should be comprehensive and focus on identifying strengths, weaknesses, and opportunities across your sales process.

Here’s what to include:

Pipeline Health: Review the pipeline metrics—deal velocity, win rates, average deal size, and pipeline coverage. Are there enough opportunities at each stage to hit your targets? Are deals moving through the funnel at the right pace? AI tools can help flag bottlenecks or anomalies here.
Sales Process Efficiency: Analyze how well your sales process is working. Are reps following the playbook? Are there inefficiencies in deal progression? Tools like Gong can provide insights into call quality, follow-ups, and adherence to best practices.
Forecast Accuracy: Evaluate the accuracy of your sales forecasts. AI can reduce forecasting errors by 20-50%, so if you’re still relying on guesswork, it’s time to upgrade your approach.
Rep Performance: Dive into individual and team performance metrics. Look at quota attainment, activity levels (calls, emails, demos), and conversion rates. Identify top performers and those who need coaching. Reps who get just three hours of coaching per month can increase close rates by 70%.
Customer Segmentation and Targeting: Are you focusing on the right customer segments? Review lead quality, conversion rates by segment, and the effectiveness of your ICP (Ideal Customer Profile). AI can help refine your ICP and prioritize high-propensity leads.
Deal Quality and Close Rates: Examine the quality of deals entering the pipeline and the close rates at each stage. Are you losing deals at a specific stage? If so, why? Metrics like time spent in each stage and reasons for lost deals can provide clarity.
Churn and Expansion: For existing customers, analyze churn rates, upsell/cross-sell performance, and NRR (Net Revenue Retention). AI can help predict churn and identify expansion opportunities.
Sales Enablement and Training: Assess the effectiveness of your sales enablement efforts. Are reps equipped with the right tools, content, and training? AI-powered tools can provide personalized coaching and identify skill gaps.
Technology and Tools: Audit your tech stack. Are your CRM, AI tools, and other platforms being used effectively? Are there gaps in your tech stack that are slowing down your team or creating inefficiencies?
Competitive Analysis: Review how your team is handling competitive threats. Are they losing deals to competitors? If so, why? AI tools can analyze call recordings to identify mentions of competitors and provide insights into how to counter them.
Customer Feedback: Incorporate customer feedback into your audit. Are customers satisfied with the sales process? What objections are they raising? This can help refine your approach and improve win rates.
Alignment Across Teams: Ensure alignment between sales, marketing, and customer success. Are leads being handed off smoothly? Is marketing supporting deals throughout the funnel? Are customer success teams equipped to drive renewals and expansions?
Compliance and Documentation: Check that all deals are properly documented and compliant with company policies. This includes contracts, pricing approvals, and any legal requirements.

Especially in the founder-led days, or even with a stretch head of sales, a lot of times these steps are skipped. Things stay too qualitative and “best efforts”. Do the sales audit right, you’ll close more.

WHAT TO DO IN A SALES AUDIT

Dear SaaStr: What Metrics Should I Be Using to Measure My Outbound Team?

By Jason Lemkin
Tuesday, April 29, 2025 | Q&A

For mid-market outbound, the funnel stats can vary depending on your execution, but here are some benchmarks to keep in mind:

Connect Rate: If you can get 5% of your targeted accounts to take a meeting or demo, you’re in a good spot. North of 10% is a sign to really lean in on outbound. This is a key metric for outbound success. It shows you’ve nailed your targeting and messaging. Anything below that, and you need to revisit your ICP (ideal customer profile) or outreach strategy.
Demo-to-Close Rate: A good demo-to-close rate for midmarket is typically around 10%-20%. If you’re below 8%-10%, your sales team will struggle to hit quotas, and you’ll burn them out. On the flip side, if you’re above 20%, it might mean your top-of-funnel isn’t broad enough, and you’re only attracting highly qualified leads.
Outbound Conversion Rate: For assisted outbound (where sales reps are actively involved), aim for a conversion rate of 15% from lead to opportunity. Higher in SMB. If you’re below that, you might need to refine your pitch or improve your follow-up process.
Sales Cycle Length: Simpler SMB deals typically close in 30 days or less. Midmarket deals typically close in 3-6 months. If your sales cycle is dragging beyond that, it’s worth analyzing where deals are getting stuck—whether it’s in discovery, proposal, or negotiation stages.
Pipeline Coverage: You’ll want at least 3x pipeline coverage to hit your targets. This means if your quarterly quota is $1M, you should have $3M in pipeline at the start of the quarter.

MORE HERE

5 Interesting Learnings from ServiceTitan at $840,000,000 in ARR

By Jason Lemkin
Wednesday, April 30, 2025 | 5 Interesting Things, Scale

5 Interesting Learnings from ServiceTitan at $840,000,000 in ARR

ServiceTitan, the operating system for the trades, continues to scale impressively, with $772M in FY25 revenue, $800m+ ARR and a clear path to $1B ARR. It’s the vertical SaaS rocketship:

$840m ARR
Still growing a stunning 29% (!)
Just above non-GAAP break-even (3% non-GAAP margins)
110% NRR and 95% GRR
$10.5B market cap (12x ARR)

This is what a 12x ARR vertical B2B leader looks like today.

5 INTERESTING LEARNINGS

644 Emerson St. Suite 200, Palo Alto, CA, 94301

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2026 Will Be a World of PLG and AI