The go-to-market landscape has fundamentally shifted in the last 12-18 months. Older playbooks don’t seem to be working as well. And at the same time, the native AI leaders are growing at a pace we’ve simply never seen before.
We’ve assembled 30 of the most actionable, data-driven articles from SaaStr.com—with most published in the past few months to ensure you’re getting the latest thinking on what’s actually working today. These are battle-tested strategies from leaders who’ve scaled companies from $1M to $3B+ ARR.
Companies that adapt fastest are pulling ahead. If you’re a founder, sales leader, or anyone building revenue at a B2B company, this curated collection represents the most essential tactical insights from the SaaStr community.
? AI & Modern GTM Revolution
The age of AI in B2B and SaaS isn’t coming—it’s here.
1. AI-Native GTM Teams Run 38% Leaner: The New Normal?
The Data Behind the New Operating Model
ICONIQ’s survey of 205 GTM executives reveals a startling truth: AI-native companies aren’t just more efficient—they’re fundamentally restructuring how go-to-market teams operate. Early-stage AI companies are running with 38% fewer GTM employees while achieving superior conversion rates.
Key Takeaway: Perplexity scaled to 5,000 enterprise customers with just 5 sales reps. This isn’t an outlier—it’s a new blueprint, at least for some.
2. GTM in The Age of AI: The Top 10 Learnings from ICONIQ’s B2B SaaS Report
The Market Split That’s Defining SaaS Success
The data tells a stark story: AI-native companies achieve 56% trial-to-paid conversion rates versus just 32% for traditional SaaS. Companies with strong AI adoption are outperforming on every metric that matters.
Key Takeaway: The conversion gap isn’t about having AI features—it’s about being fundamentally built around AI.
3. AI in GTM Efficiency: The Playbooks from Databricks, Monday.com and Benchling
How Three High-Growth Companies Actually Implement AI
Go beyond the hype with tactical playbooks from revenue leaders at scale. Learn how Monday.com built their “deal desk co-pilot” and why the biggest wins come from platform integration, not point solutions.
Key Takeaway: The winners aren’t companies with the most AI tools—they’re the ones who thoughtfully integrate AI into existing workflows.
→ Read the tactical playbooks here
4. AI, Sales + GTM: This Changes Everything with Jason Lemkin and Owner CRO Kyle Norton
The Future of Revenue Teams
By end of year, successful CROs will need to manage teams that are 50% AI agents and 50% human. This isn’t science fiction—it’s operational reality for forward-thinking revenue organizations.
Key Takeaway: Team members who aren’t genuinely AI-curious should be shown the door. That’s not hyperbole—that’s the new competitive reality.
→ Read how sales teams have already changed with AI here
5. The GTM Playbook Is Mostly Dead. But What’s The AI Era Replacement?
What Actually Works in 2025
The 2021 playbook of endless outbound emails and low-energy digital events is dead. The 2025 GTM Playbook requires getting out of the home office more, working harder, and spending more human time per prospect—not less.
Key Takeaway: AI hasn’t made GTM easier; it’s made competition fiercer. The companies winning are doing the fundamentals better, not just deploying more tools.
6. Sam Blond + Jason Lemkin “GTM: How It’s Changed, How It’s Changing, and What Hasn’t Changed (Yet)”
Counterintuitive Insights from Leading CROs
Through interviews with CROs from Toast, Databricks, Wiz, and Codeium, discover why territory design beats AI tools, why in-person sales still generates 3X higher conversion rates, and why some companies are finding cold calling surprisingly effective.
Key Takeaway: While everyone chases AI tools, fundamentals like territory optimization and in-person relationships are creating outsized competitive advantages.
→ Read the counterintuitive insights here
? Sales Leadership & Hiring
Building great revenue teams starts with hiring great leaders. These articles provide the tactical frameworks for finding, evaluating, and onboarding sales leadership that can scale.
7. The Top 10+ Questions to Ask a VP of Sales During an Interview (with Cheatsheet)
The Updated 2025 Interview Guide
The classic SaaStr post, updated for the AI-driven, distributed world. These questions will help you separate the true closers from the PowerPoint-wielding process managers.
Key Takeaway: Before hiring any VP of Sales, make sure they can demo your product themselves. If they can’t sell, they can’t lead.
→ Read the interview cheatsheet here
8. What A New VP of Sales Needs To Be Doing Their First 2 Weeks
The Make-or-Break First 14 Days
Your new VP of Sales should be able to demo the product by the end of Week 1 and be recruiting top talent before they even start. Here’s the tactical playbook for ensuring your revenue leader makes an immediate impact.
Key Takeaway: The first two weeks are about establishing credibility through hands-on execution, not just “learning the business.”
→ Read the first 2 weeks playbook here
9. Hiring a Great VP of Sales: The New, Latest Edition with Jason Lemkin
Avoiding the Jaded, Broken, and Done
The post-2021 market has left many sales leaders burned out. Learn to identify the “jaded” (who blame everyone else), the “broken” (who’ve lost their edge), and the “done” (who don’t want to sell anymore).
Key Takeaway: Don’t hire someone who’s spent the last 18 months as a “fractional CRO”—they’ve already shown they don’t want the intensity of full-time revenue leadership.
→ Read the updated hiring guide here
10. The Top 10 Mistakes People Make When Hiring a VP of Sales
The Patterns That Kill Revenue Organizations
From hiring based on logos to confusing CRO roles with escape routes from selling, these are the systematic errors that set revenue teams up for failure.
Key Takeaway: A VP of Sales must love closing deals above all else. CRO is not a place to escape sales—it’s where the best closers go to scale their impact.
→ Read the top 10 mistakes here
11. From $1M to $3B ARR: Databricks CRO Ron Gabrisko on Scaling a Revenue Rocket Ship
Lessons from One of the Largest Pre-IPO Companies
Ron Gabrisko’s journey with Databricks from under $1M to over $3B ARR offers rare insights into hypergrowth revenue scaling. Learn how they leveraged open-source community, built technical sales teams, and focused on pricing power over operational efficiency.
Key Takeaway: For technical products with technical buyers, hire sales leaders with engineering backgrounds. Technical buyers don’t want to talk to traditional salespeople.
→ Read the Databricks scaling story here
12. CRO Confidential: The Proven Customer Acquisition Strategies Behind Toast’s Explosive Growth
Field Sales Excellence in a Low-ACV Environment
Toast’s CRO Jonathan Vassil reveals how they built one of the strongest sales organizations in B2B, despite operating in a challenging low-ACV ($10K), field-based SMB environment. Their data shows prospects who receive on-site visits close at 3X higher rates.
Key Takeaway: One out of five deals at Toast comes from referrals. The “flywheel concept” works: when you reach density in a market, win rates and productivity increase dramatically.
→ Read the Toast growth strategies here
? Sales Compensation & Commission Plans
Get compensation wrong and even the best reps will underperform. These articles provide proven frameworks for building comp plans that drive the right behaviors.
13. A Framework For Your First SaaS Sales Comp Plan
Lessons from Scaling to $25M ARR at SaaStr
Jason Lemkin’s hard-won lessons from building sales comp plans that actually work. Learn why BigCo sales comp plans fail at startups and how to structure compensation that motivates top performers while weeding out mediocrity.
Key Takeaway: Pay competitive base salaries but make reps cover their costs before hitting full bonus. This approach attracts top talent while encouraging poor performers to leave.
→ Read the comp plan framework here
14. Dear SaaStr: How Should I Build Our First Sales Comp Plan?
The Step-by-Step Blueprint
A comprehensive guide covering everything from base+commission structures to retention bonuses and upsell incentives. Includes real examples and rough quota guidelines for SMB, mid-market, and enterprise.
Key Takeaway: Keep it simple enough that reps can calculate their earnings quickly. If they can’t understand it, they’ll lose motivation.
→ Read the step-by-step blueprint here
15. Dear SaaStr: How Much Do I Pay My First Sales Rep?
Three Simple Rules for Early-Stage Compensation
Your first rep doesn’t have to be magically profitable on Day 1. Learn how to structure competitive OTE while back-solving for the three key constraints every startup faces.
Key Takeaway: It often makes sense to pay a much higher commission for an introductory period—Jason paid his first reps 100% of what they took home for the first 60 days.
→ Read the first rep compensation guide here
16. Dear SaaStr: What’s the Proper Way to Commission Multi-Year Deals?
Handling Complex Deal Structures
Multi-year deals with increasing ACV require thoughtful commission structures. Learn when to pay on cash receipt versus contract signing, and how to avoid the incentive misalignment that can destroy deal quality.
Key Takeaway: Until you’re at $10M+ ARR, pay higher commissions on prepaid cash for multi-year deals—the cash flow benefits usually outweigh the commission costs.
→ Read the multi-year deal guide here
17. Yes, You Do Have To Pay Sales Commissions When a Partner Mostly Closes The Deal
Partnership Channel Compensation
Don’t deduct partner referral fees from sales commissions. Your rep still needs to coordinate, manage the relationship, and ensure the deal closes successfully.
Key Takeaway: Partners rarely close deals entirely on their own—your rep is still doing significant work that deserves compensation.
→ Read the partner compensation guide here
18. Dear SaaStr: How Much Do SaaS Sales People Make in Commission?
The 4x-5x Rule and Market Standards
Sales reps need to bring in 4x-5x what they take home in total compensation. Most B2B companies end up with roughly a 10%/10% model: 10% of quota in base, 10% in commission.
Key Takeaway: If your SaaS sales rep can close $1M a year, paying them $200K (20%) in base+bonus is standard and justifiable.
→ Read the market standards here
? GTM Strategy & Scaling
Moving from founder-led sales to scalable revenue requires systematic GTM strategy. These articles show you how the best companies build repeatable growth engines.
19. How to Scale Go-to-Market Through IPO with ICONIQ Growth’s General Partners
The Four Stages of GTM Evolution
ICONIQ’s data-driven framework for scaling GTM from founder-led sales through IPO. Learn the key milestones, benchmarks, and team-building strategies for each stage of growth.
Key Takeaway: 30% of companies hire their CMOs less than a year before going public—the last CMO hire is crucial for IPO readiness.
→ Read the IPO scaling guide here
20. How to Build Go-to-Market Efficiency in SMB Sales with Owner.com CRO Kyle Norton
From $3M to $21M ARR in 22 Months
Kyle Norton’s tactical playbook for building GTM efficiency while scaling rapidly. Learn how Owner reduced CAC and operated with sub-one burn multiple during hypergrowth.
Key Takeaway: The first lesson is learning to say no. If you’re losing too many customers early, don’t add more to the top of the funnel—fix the leaky bucket first.
→ Read the GTM efficiency playbook here
21. How We Scaled OpenAI’s Sales Team from 10 to 500 People in 2 Years: The Inside Playbook from ChatGPT Enterprise’s GTM Leader Maggie Hott
Hypergrowth Lessons from the AI Revolution
Maggie Hott’s tactical playbook from scaling one of the fastest-growing enterprise applications in history. Learn why one exceptional hire beats three average ones, how to avoid the “logo trap,” and why early sales teams should focus on salary over commission.
Key Takeaway: When founders tell her they want to go after Walmart or Nike, she pushes back 10/10 times. Enterprises are wrong for early-stage companies because of complex hierarchies and lengthy cycles.
→ Read the OpenAI scaling playbook here
22. Top 10 GTM Mistakes Founders Are Making Today with SaaStr CEO Jason Lemkin
Updated for the AI GTM World
The GTM landscape has fundamentally changed since 2023, let alone the 2021 era. Learn the new mistakes founders are making, from hiring VPs who can’t demo the product to cutting marketing to zero during downturns.
Key Takeaway: Whatever you do, don’t hire a Head of Sales who can’t demo the product before day one. You don’t have the resources or brand to carry you.
→ Read the top GTM mistakes here
? Sales Operations & Process
Great sales teams aren’t just about great people—they’re about great processes. These articles show you how to build the operational foundation for scalable revenue.
23. How to Build Pipeline and GTM Alignment with Datadog’s CMO Sara Varni
The Four-Horsemen Model for Pipeline Management
Sara Varni’s framework for creating alignment between sales and marketing through joint pipeline targets. Learn how to avoid the trap of departmental optimization at the expense of overall business results.
Key Takeaway: You never want marketers taking a victory lap if they hit their targets but sales didn’t. Marketing should take ownership over pipeline, even if they don’t get credit.
→ Read the pipeline alignment guide here
24. How Salesforce Runs Its Internal Forecasting Process
Under the Hood at the World’s Largest SaaS Company
Salesforce’s three-pillar approach to forecasting culture: people (data-driven accountability), process (alignment across departments), and technology (clean pipeline management). They have sales forecasting meetings every single day.
Key Takeaway: A deal doesn’t become part of the pipeline until it reaches stage two. Clean pipeline definition is essential for accurate forecasting.
→ Read the Salesforce forecasting process here
25. Dear SaaStr: How Do I Know If My New VP of Sales is Working Out?
The 60-Day Evaluation Framework
Revenue growth, pipeline metrics, team building, process improvements, and deal closing—here’s how to evaluate whether your VP of Sales is actually moving the needle.
Key Takeaway: If your revenue per lead doesn’t improve within one sales cycle, they’re not doing their job. Time is your most valuable asset in SaaS.
→ Read the VP evaluation framework here
? Early-Stage Sales Hiring
Getting your first sales hires right sets the foundation for everything that follows. These articles provide the tactical guidance for building your initial revenue team.
26. Should You Hire a Sales Rep First, Or a Sales Manager?
The Ideal Hiring Sequence
Close the first 10-20 customers yourself, then hire 2 sales reps (not just 1), then hire a head of sales after they’re both hitting quota. Don’t ask a VP of Sales to figure out product-market fit.
Key Takeaway: You need to run an A/B test with your first sales hires. If you only hire one rep, you won’t know why they succeed or fail.
→ Read the hiring sequence guide here
27. When You Hire Your First Sales Rep — Just Make Sure You Hire Two
The A/B Testing Imperative
Even if it seems expensive, hire two reps to start. You need at least two to learn what works, run comparisons, and avoid the trap of not knowing whether success or failure is due to the rep or your process.
Key Takeaway: No matter how well your first rep does, you won’t learn anything if you only hire one. You need data points to build a scalable system.
→ Read the two-rep strategy here
28. Dear SaaStr: When Should a Startup Hire its First Sales Person, and What Should Their Profile Look Like?
The Non-Negotiable Criteria
Hire someone who’s sold at your price point, has startup experience, and—most importantly—someone you’d buy your own product from. Don’t hire someone that hasn’t worked at a startup; they can’t survive without brand and infrastructure.
Key Takeaway: Everyone makes the mistake of hiring someone they wouldn’t buy from themselves. Leads are precious in the early days—you can’t entrust them to someone who can’t sell.
→ Read the first salesperson guide here
?️ Sales Team Building & Culture
Building a high-performing sales culture requires intentional effort. These articles show you how to create environments where top performers thrive.
29. 7 Learnings: Building Your First, Great Sales Development (SDR) Team
The Foundation of Scalable Pipeline
SDR teams with the right talent, onboarding, and management can build consistent pipeline that scales. But miss on talent and your team is almost certain to fail—great people find a way to succeed even when systems aren’t perfect.
Key Takeaway: Hire SDRs in pairs to create “compassionate competition.” Top performers become pacesetters who raise the game of their peers.
→ Read the SDR team building guide here
30. Scaling A SaaS Sales Team While Building Culture with Scott Pugh, VP of Sales at Figma
Category Creator Playbook
Scott Pugh’s strategy for scaling sales teams at category creators like Figma: recruitment (hiring the best talent), enablement (investing in professional growth), and culture (developing sub-cultures that enable scaling).
Key Takeaway: Culture beats strategy. Without culture, strategic plans are useless. When you build culture, it democratizes decision-making and enables people to make decisions without constantly seeking approval.
→ Read the Figma culture scaling guide here
The Bottom Line
The revenue landscape is evolving faster than ever. AI is creating new opportunities for efficiency while making competition fiercer. Traditional GTM playbooks are breaking down, but the fundamentals—great people, clear processes, aligned incentives—remain more important than ever.
These 30 articles represent thousands of hours of real-world experience from leaders who’ve built revenue engines that scale. Whether you’re a first-time founder hiring your initial sales rep or a seasoned executive navigating AI transformation, these insights will help you build the revenue organization your business needs to win.
The companies that study these playbooks, adapt them to their context, and execute with discipline will be the ones that thrive in the age of AI. The question isn’t whether your GTM will need to evolve—it’s how quickly you can learn from those who’ve already figured it out.
Want to dive deeper? Each of these articles contains tactical frameworks, real data, and actionable advice you can implement immediately. Start with the areas most relevant to your current challenges, but don’t skip the sections that feel “advanced”—the best revenue leaders are always learning from stages they haven’t reached yet.
