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Curated SaaS and tech insight from around the web repackaged for people to put to good use
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1. SaaS METRIC OF THE WEEK: Here is a new one - The Customer Success Ratio. Calculate this as CSM expense ÷ Net New ARR from Existing Customers. Track it to see if your post-sale team drives growth or burns margin. Rule of thumb: keep it <10%.
2. AI: Bond Capital's monster 340-slide AI report is a goldmine: ChatGPT scaled 20x faster than the internet (p. 20), 73% say AI sounds human (p. 26), inference costs down 99% (p. 40), agent apps surging (p. 93), revenue scaling fast (p. 102), 70% of GenAI users seeing productivity gains (p. 109). 3. UNICORN: The 30-year unicorn backlog may finally be moving (this is referencing the 700+ unicorns stuck in private markets). Q2 saw 20 unicorn exits (vs. six last year), led by AI, cyber & health. Wiz's $32B buyout, CoreWeave IPO & more signal some kinda thaw—but with 700+ unicorns still waiting, this logjam may take some time. 4. VENTURE: VCs seem to be funding two things: AI & SaaS—but in very different ways. AI receives massive rounds, but even pre-revenue SaaS companies must show traction and efficiency. AI = 'fund the vision,' SaaS = 'fund metrics.' Same VCs, two mindsets. 5. GROWTH: Unlike the focus of #3 above, mostlymetrics breaks down why 10-15% annual SaaS growth is just fine for many. Not every startup is a rocket ship—and that's OK. Realistic growth expectations & compounding wins > unicorn-chasing. 6. PRODUCTIVITY: I've been having lots of productivity talks over the past few weeks, and this is a great article that validates a lot of the discussions (and, tbh, gave me a few hard truths to act on). It's targeted at engineers, but the 15 productivity hacks here apply to any knowledge worker IMO. High-signal, no fluff. 7. MARKETING: Here is a GitHub treasure trove: Marketing for Founders. Crowdsourced, no-nonsense advice across positioning, pricing, SEO & more. A really practical resource worth bookmarking for revisits. 8. PRICING: Check out this go-to pricing guide for early-stage founders. It covers freemium, premium, usage-based, and hybrid models—plus when (and how) to charge more. 9. MOATS (AI): Clouded Judgement dives into what modern SaaS moats in the modern AI world look like: Speed isn't just important; it is the moat. As well as scale, network effects, brand, and distribution. But because AI compresses product moats, this all matters more than ever. (also read the rest of that post - tons of nuggets always in there - benchmarks on multiples, revenues, gross margin, etc., etc.) 10. CASE STUDY: Perplexity AI is scaling fast! Check this deep dive on its acquisition and retention machine. Sixty percent of traffic is direct, mobile usage is exploding, and SEO and product-led virality do the heavy lifting. POD OF THE WEEK: Adding on to number 9 above on speed as a Moat - Sam Parr and Shaan Puri talk to Jason Lemkin about cloning yourself with AI and how ChatGPT will be the end of incumbent apps. 1. SaaS METRIC OF THE WEEK: ARR - Here is a whole book for you covering ARR. It covers everything you need to know to define, build, and report on ARR from scratch based on experiences at Intercom, Atlassian, and Stripe. I also have Bessemer Ventures claiming to have a founder's roadmap to $100 million ARR.
2. OUTBOUND vs INBOUND: How you handle an inbound lead vs an outbound lead is quite different. Check this article from Jack Jorgovan on how Outbound leads differ (and how to close them). The team at Predictive Revenue has been running over 50 outbound sales experiments to find out what works best (and what doesn't.). Watch the whole series on YouTube. SaaS Weekly also has a guide on automating outbound emails by leveraging intent signals to drive better-targeted campaigns. 3. API: APIs aren't just dev tools—they're products, and pretty much all AI needs them. Zuplo's API guide outlines how to run API product management like a SaaS, covering pricing, usage tiers, onboarding, and churn. If you've got an API, this gives you a roadmap. 4. GROWTH 1/2: Testing new tactics for marketing growth takes a lot of resources, and most of us often don't have much time to run experiments. Check out this Google Doc from Dashly, which collects 100 growth marketing hypotheses tested by their experts. (includes advert retargeting, wait list for product launches, niche glossaries, etc.) 5. GROWTH 2/2: According to Mostly Metrics, companies and deals with ACV in the $50K to $100K deal range are feeling the heat right now as they are caught in the crosshairs of CFOs being tasked with cutting budgets. I'm feeling judged. The data shows that enterprise purchases are stickier due to their complex implementation and high switching costs, while SMB purchases fly under the radar. 6. BENCHMARKS: Check out this benchmark's goldmine with the BenchmarkIT Report (all B2B SaaS), and it's pretty interactive (or snag the PDF here). Median growth for SaaS companies is 30%, and Net Revenue Retention (NRR) is at 105%. Median Customer Acquisition Cost (CAC) payback is 16 MONTHS! and here is one of my favorites - an average of $.69 per $1 of expansion revenue generated. 7. AGENTIC: This article argues that we're entering an agentic web era. This is where AI agents act on our behalf, not just answer questions; they also take action. But the "original sin" of the internet (SEO and ad-based enshitification) could distort this future - dammit. 8. AI SCALE: There's a hidden scaling law for LLMs: performance jumps when trained on multiple languages (original study here) — even if you only test in one. It's a fascinating take on multilingual data as a scale amplifier, not just a translation tool. 9. ADVICE: Here is the motherload of all advice, 99 of the sharpest insights from 99 founders, all in one post. From mindset to mechanics, it's a dense but skimmable wall of gold. There's gotta be at least three things you can copy into your notes. 10. CASE STUDY - MOATS: Complimenting the Pod of the Week (below), CB Insights reports on Moats IRL with 29 examples of enduring moats (from Amazon and Tesla to Starbucks and Coinbase). Key strategies include leveraging network effects, scaling through cost advantages, and capitalizing on brand loyalty. POD OF THE WEEK: Expanding on number 9 and 10 above, here is Jason Lemkin's pod/vid on Top 10 Moats in SaaS. 1. SaaS METRIC OF THE WEEK: AI Metrics: This is a great one from David Kellogg, who recently presented at SaaS Metrics Palooza 2024 on "The Impact of AI on SaaS Metrics" slides in a PDF version here. The event he presented at is actually whacked full of good talks so well worth the (somewhat weird) on-demand replay you can get access to here.
2. NCT: Crack open your tech dictionaries, I have a new acronym to lob your way. OKRs are old school. Ravi Mehta's NCT (Narrative, Commitments, Tasks) model simplifies goal setting. So, instead of vague objectives, start with a clear Narrative explaining the "why" behind each goal. Next, set 3-5 measurable quarterly commitments, with Tasks as actionable steps. The difference is that OKRs can be overly ambitious, but NCTs focus on achievable milestones that align closely with strategic priorities, more Agile in a way as course corrections are easier (and it increases team accountability). 3. CONFLICTS: David Kellogg suggests designing our businesses to surface essential conflicts. Instead of reducing conflicts, leaders should identify which ones add value and make sure they are heard. For example, separating Sales and Customer Success encourages transparency around upselling conflicts. By purposefully structuring teams, leaders can maintain productive tensions that drive growth and reduce irrelevant friction. 4. INCIDENT MANAGEMENT: We all have incidents and accidents, and incident reviews are critical to improving system reliability and teams, but many of us fall short of making these sessions productive. According to The Pragmatic Engineer, some of the best practices (which I have adopted and now use) include creating a blameless environment to encourage honest assessments, focusing on learning rather than punishment, and ensuring incident reviews are actionable. The template I reference is from Atlassian - they have a very detailed Incident Management book, aaaand you can generate your own template here. 5. CASH MANAGEMENT: Here is Part 1 of a 3-part Guide to Cash Management for Startups, which highlights bank account strategies at different Stages. The startup phase needs basic checking and savings accounts for operational expenses and emergencies, maintaining liquidity, managing cash flow, and keeping financial controls strict. It prioritizes simplicity and security in banking structures. 6. AI WARS (2025): The big public cloud giants are doubling down on AI. AWS, GCP, and Azure are now well in bed with leading LLMs (all three have invested in Anthropic) while also building rival foundation models and AI accelerators. This CB Insights report maps out the battlefronts: infrastructure, partnerships, custom silicon, and AI sec. Looks to be about $250B+ of capex on the table, and OpenAI's $500B Stargate ambitions, plus the crazy io news, are a looming threat. 7. DEVS: a16z outlines nine developer trends shaping up the AI era - from AI agents and LLM-native IDEs to "Bring Your Own Model" platforms. AI integrations with codebases are absolutely reshaping workflows and platform choices alike. And, of course, the smart money is watching these shifts closely. 8. BIZ DEV: Read this before your next "strategic" partnership. Business development does not necessarily equal sales. Jason Cohen breaks down startup biz dev into five distinct types, from co-marketing to integrations. And ya know, most BD flops come from mismatched expectations. 9. EQUITY: Founder equity convos are hard - especially when your co-founder is also your friend, but it ain't equal. This breakdown offers a calm, thoughtful approach to handling founder splits without ruining the relationship. 10. CASE STUDY: Palantir's moat isn't just tech—it's time. This teardown argues Palantir's edge lies in deeply embedded systems, long cycles, and government-grade entrenchment. A strong example of sticky enterprise sales done right. POD OF THE WEEK: Great growth and marketing lessons from the early days at OpenAI and Stripe on building differentiated strategies that can actually work. 1. SaaS METRIC OF THE WEEK: DAU/MAU. The DAU/MAU ratio is a popular metric for companies that need to measure user engagement. Rule of thumb: Average is 13%; apps with over 20% = good. If you have 50%+ - you're world-class.
2. CASH MANAGEMENT: Part 1 of a 3-part Guide to Cash Management for Startups highlights bank account strategies at different Stages. The startup phase needs basic checking and savings accounts for operational expenses and emergencies, maintaining liquidity, managing cash flow, and keeping financial controls strict. It prioritizes simplicity and security in banking structures. 3. CAPITAL EFFICIENCY: Capital Efficiency has been back in Vogue for a while, and according to Bessemer Venture Partners, here are the benchmarks for B2B SaaS to measure your payback against (full report here). Across all companies, engineering is consistently the largest department, with customer success and product at about 10% and marketing at only 7%. This slide also has median headcount by stage - which is a great metric to track. 4. SECONDARIES: Secondaries (selling private startup shares before exit) were quite recently seen as pretty taboo, but now they are becoming critical for seed funds managing longer timelines and shifting LP expectations. Hunter Walk's post nails the why. 5. BUYERS vs USERS: The person writing you a check is not necessarily the same person getting value from your business. So, take a read of this insightful article from HeavyBit on differentiating messaging based on this premise and the different profiles. 6. VENTURE: The Q1 2025 PitchBook NVCA report is out, and the overall VC mood looks complicated. On paper, the $91.5B in deals (thanks to a few giants like OpenAI) masks weak liquidity, stalled IPOs, and just $10B in new fundraising. Tariffs and uncertainty have investors sitting tight, and early-stage deals remain depressed. 7. LEAN STARTUP: Provocative blog post - but maybe not wrong. The Lean Startup world is gone? AI now writes most of the code—so the bottleneck is no longer dev; it's user attention. Time to rethink how we build. 8. FOUNDER OWNERSHIP: Carta's Spring 2025 SaaS report confirms the dilution game: VC money comes at a steep equity cost. Each round chips away—pre-seed, employees, co-founders, SAFEs, and traditional VCs. By IPO, founders often hold much less than they think. Dilution isn't a bug; it's the whole game. 9. QUANTUM: Late last year, I noted that Google had a new quantum chip, Willow, which marked a bonkers leap in compute power (completing a computation in under five minutes that would have taken the world's fastest supercomputer 10 septillion years - older than the known universe). Quantum cracking isn't hypothetical sci-fi anymore - it's an inevitability. 10. CASE STUDY: Crunchbase crunched the Venture numbers over the past 10 years, and global VC has nearly tripled in a decade ($158B in 2014 to $433B in 2021's peak), then cooling to $285B in 2023. Deal count? Doubled. The US leads as always, but China has pulled back. This is a data-rich look at a wild decade in VC. POD OF THE WEEK: Investor Elad Gil (Airbnb, Stripe, Coinbase) shares his playbook: Insights on why the market matters more than the founder, why AI may be under-hyped, and why he thinks remote work hurts innovation. 1. SaaS METRIC OF THE WEEK: What KPIs do venture firms consistently care about across stages? This article highlights how KPIs evolve from early traction metrics like CAC and LTV to more advanced indicators like NRR as companies scale and also shifting into survival metrics like cash runway to operational efficiencies.
2. CAPITAL (seed): AngelList data shows that, on average, seed-stage companies have about 18 months to secure a Series A. Because if a startup isn't marked up by then, it's likely to stall. 3. REVERSE TRIALS: Reverse Trials are a play on freemium, where new users start with a time-limited trial of all your paid features, and at the end of the trial, they can either buy or downgrade to a fully free tier - this article also explains how Airtable do this well. The benefit here is that, emotionally, users experience loss aversion, where the pain of losing something is twice as powerful of a motivator as the pleasure of gaining. 4. AI EVALUATIONS: Oh - this one is good. Every AI startup sounds like a rocket ship - but we all know about the good ol' Startup Jazz Hands - all sizzle and no sausage. Well, check this framework, which helps cut through the pitch BS—what matters, what's sizzle-y fluff, and how to build (or back) something real (or at least really AI). 5. AGI: Speaking of Jazz Hands - Is AGI (Artificial General Intelligence) real or just Silicon Valley cosplay with a massive budget? Check this takedown of the "AGI startup" wave, which calls out the hype, the grift, and what real researchers actually think. 6. VENTURE PITCH: Wanna know what's really happening behind the scenes in a VC pitch? Avery Law breaks down the VC decision-making process: partner politics and legal diligence bottlenecks. Founders: it's ain't just about your pitch. Timing, biases, and internal champions all matter too. 7. PLG: Upgrade paths are a well-known strategy, especially in the PLG world, for increasing revenue, especially LTV/ACV, but not all users upgrade in the same way. Check out this breakdown of SaaS upgrade paths—feature-, seat-, and usage-based. It's a smart take with practical diagrams (and I love me some good pictures). 8. TESTING: We got customers on the A/B test path this week, and y'all don't actually test enough (or at least test well) - me included. Check out this guide, which lays out a full-stack testing strategy, from messaging to monetization, and shows why velocity, not perfection, is your friend and compounds the wins. 9. GENAI: Google Cloud's new 2025 AI Infrastructure report confirms what we know to be obvious: GenAI is now mainstream. 98% of orgs are developing or using it in production. It's not hype, it's now core infra. But cost, data quality, and hybrid deployments are critical to success. Plus, those IT Consultancy companies are the biggest adopters in Prod. 10. CASE STUDY: How many hours should founders work? Check out this analysis of YCombinator Founders. It's a 3-part series, but a good TL;DR is that pre-product-market fit founders work the most hours, with time spent decreasing as companies grow and gain traction. For many of us, it's a good read for a) Validation and b) Tips on managing your time and not burning out. POD OF THE WEEK: Total Bang for the buck podcast - 11 essential SaaS metrics explained in 11 minutes. 1. SaaS METRIC OF THE WEEK: Revenue & Burn per Employee. In this profits-over-growth new SaaS world, forget vanity metrics. This post makes the case for tracking Revenue and Burn per Employee as core performance metrics. Why? They reveal whether you're scaling efficiently—or just adding bodies. It also includes great benchmarks across stages.
2. CLOSEDAI?: OpenAI wants to drop the "nonprofit" label - at least in practice if not in name. This article takes a deeper look at what the heck that means with a shift toward profit-maximizing governance. This will bring a bunch of pretty understandable tension with its current mission and how it's navigating the AGI arms race. AI power play shenanigans are well underway. 3. VENTURE 1: On paper Q1 2025 saw a funding rebound. $113B in VC funding—AI took $60B of it, with OpenAI alone raising $40B. Late-stage deals soared 147% YoY, but if you strip out OpenAI's $40B mega-round, early and seed-stage funding actually fell. Seed dropped 14%, Asia hit decade lows, M&A saw $71B in exits. TL;DR: Big rounds for the few, AI dominance, early-stage getting squeezed. 4. VENTURE 2: Whoa! Silicon Valley is the opposite of dead. In Q1 2025, the Bay Area accounted for the majority of all US VC volume value and DOMINATED deal value - as in more dollars than the next five regions combined ($58.7B vs NY in second place at $7.1B). Startups may be everywhere, but the money's still coming from the Valley. 5. BATMAN EFFECT: OK. I'm in just based on the name! But hey - do you struggle with focus or performance in this modern multi-screen, notifications everywheeeere, distracted world? So just pretend you're someone else. Research shows that adopting an alter ego (like Batman - yup, I said it in Batman's voice) helps kids AND adults alike push through tough tasks. Sounds stupid, but works brilliantly (again - I just said that in my Batman Voice). 6. PRODUCT MARKET FIT 1: Product Market Fit - is it getting harder? Mostly Metrics digs into why hitting product-market fit feels tougher than ever - because it is! Blame crowded markets, high expectations, and tighter budgets. PMF ain't dead—but it's definitely moved. 7. PRODUCT MARKET FIT 2: Adding on from number 5 above, this Startup-ism is important because more than 50% of the time, the lack of PMF factors into the reason a startup fails (keep reading this article though as it goes through how StartupOS figured their own PMF out). AirTree Ventures has this article looking at what metrics VCs like them look at for signs of Product-Market Fit - and also what the red flags are. 8. GTM TEAMS: It's experientially obvious - but only if you have lived through it. Early GTM hires can make or break your cadence and sales motions. So check this list of 9 hiring mistakes, which includes skipping onboarding, premature AE hires - big one! 9. P&L + COGS: SaaS P&Ls are structured in specific ways, as defining what goes into the cost of goods sold (COGS) section is important. So take a good read of what the SaaSCFO recommends to include for COGS and how to structure a SaaS P&L. According to the Author - 90% of them are structured incorrectly, 5% are close, and 5% are correct. 10. CASE STUDY: Pro-Rata! Pro rata rights let VCs keep their ownership in future startup rounds - but the VC often skip them. This case study shows how one VC passed on a $2B outcome by doing just that. This " pro rata trap" reveals how to fund math, bias, and timing can block big wins. POD OF THE WEEK: Is Predictable Revenue Dead? Fascinating (but long) podcast with Collin Stewart of Predictable Revenue with statements like building an SDR team takes 730 days, not 90. What???? 1. SaaS METRIC OF THE WEEK: CHURN: This is a kinda newsletter in two halves this week - looking at the bigger pictures of churn. According to CatchJS, we're all calculating churn rates wrong. If you love Statistics, the article is well worth reading, and it even gives some Python code to perform the more complicated probability-based equation they recommend. You can then check out this tool (as a handy Google Sheet) from Newfund as a way to analyze the strength of revenue streams for any B2B startup. A complimentary article outlining the methodology behind the tool is here (and you should read it first).
2. CHURN 2: 40% of SaaS businesses with ARR in the $15-30m range have negative churn and, on average, startups with ARPA over $1k have negative churn. The higher the ARPA, the lower the monthly net MRR churn rate. This is because of lower gross churn and higher expansion revenue at higher ARPAs. This article notes that a monthly churn rate below 5% is healthy, while under 3% is best-in-class. 3. CHURN 3: It's the ultimate leaky bucket. BVP's guide on tackling customer churn explains how to identify root causes and implement strategies to reduce attrition (that can be terminal). Analyzing churn data, improving customer onboarding, and enhancing product value to retain users are all in there. The guide also provides actionable steps for creating a comprehensive churn action plan to plug those leaks. 4. RETENTION: Adding onto #1, #2, and #3 above, Churn math is messy. SaaS Capital outlines the five biggest pitfalls in measuring retention—from inconsistent cohorts to expansion masking poor GDR. If your NRR looks "fine," it might not be. Start here before your next board deck. 5. LEAD: A new term for you us all to ponder, "Leading from the front" isn't just some kind of self-help book cliché - for most of us in startup land, it's the difference between high-trust teams and checked-out ones. Stay SaaSy breaks down how great leaders model urgency, own the hard stuff, and never ask for what they won't do themselves. 6. ESTIMATES: "That'll take months." Heard that before? Ryan Singer unpacks what engineers really mean when they say it. Hint: it's often not the code—it's all the unknowns that make things so hand-wavy. 7. EXPERIMENTATION: Running one feature test a quarter won't cut it. Aakash Gupta breaks down how top SaaS teams build and scale experimentation engines -from setting up infrastructure to aligning product, data, and engineering around test velocity. If you want to ship smarter (I definitely do!), check it. 8. VENTURE: It's difficult to mention tariffs in a weekly newsletter as it's a constantly moving target (I've already removed listings twice), but Venture deal volume just posted its biggest drop in a year—and tariffs might be the reason. Startups facing supply chain costs and trade uncertainty are delaying raises (and those pesky forward multiples). Tariffs are messy to track, but their potentially chilling effects look to be starting to show. 9. WORK TRENDS: Microsoft has just launched the 2025 Work Trend Index, where the trend is the rise of the Frontier Firm: companies rebuilding around AI, human-agent teams, and intelligence on tap. 82% of leaders in the survey say it's a pivotal year to rethink strategy. Copilots, agent bosses, and flexible org charts are all actual strategies happening now. 10. CASE STUDY: Superhuman got a little obsessed with onboarding but it resulted in a 75% trial-to-paid conversion. They layered concierge onboarding calls, tailored user journeys, and laid down some agggggressive time to value (they cheesily call it time to magic) moments, they transformed their churn-prone SaaS trials into revenue. POD OF THE WEEK: Jason Lemkin jumps onto the 20VC podcast and covers everything: OpenAI acquisition of Windsurf (for a cool $3BN), Are endowments in trouble? 1. SaaS METRIC OF THE WEEK: Margins by Revenue Stream. Understanding gross margins by revenue stream is crucial for a) SaaS profitability and b) Figuring out what products/features work and what don't. Check out the SaaS CFO's article on proper rev stream accounting and a detailed SaaS P&L setup to enable accurate margin analysis across your revenue streams. Best-in-class SaaS gross margin for revenue is 80% as your reference point.
2. JTBD: Jobs to be Done is one of my favorite frameworks - it's a way to make innovation accessible and tangible in very pragmatic ways. Take a light read here on a lightweight JTBD framework - broken down with real-world business examples, you can also skip straight to the templates. Or go for the more comprehensive one here (that also has a template). Theory Ventures 2024 Go-to-Market Survey. 3. STRATEGY: Startups often inherit secondhand problems—metrics, goals, and strategies from companies (or newsletters) nothing like them. This post makes the case for solving real, first-principles-driven problems instead. 4. TERM SHEETS: Bookmark this for future reference - a Term Sheets guide that explains the most important clauses—like valuation, liquidation preferences, and anti-dilution protections—and offers some strategies for negotiating more founder favorable terms. 5. AGENTIC: You'll hear "agentic" a lot this year—Bessemer breaks down their version of an AI Agent Autonomy Scale, from dumb scripts to fully autonomous workflows. The big takeaway? Most "agents" today are barely tools, but true autonomy is coming. 6. SPEND: The SaaS Capital Spending Benchmarks for B2B SaaS Companies is out - bookmark this when it's time to benchmark your wallets y'all! Bootstrapped B2B SaaS companies spend 95% of ARR (hey - I do better than that!!), while VC-backed ones burn 107%. Equity-backed teams spend 100% more on marketing and 71% more on R&D. 7. OFFENSIVE DATA: No - not the type you don't like, the other type, that attacks! Most teams only use data when things break. Elena Verna makes the case for offensive analytics—proactively surfacing what's working and why. From Slack to Uber to Google, some great use cases profiled! 8. CHIP WARS: GPU/AI-based silicon is the new arms race. NVIDIA, AMD, Intel, and a wave of startups are battling to power the next-gen models. Speed, efficiency, and memory optimization are the focus - with big moves in open-source AI chips too. 9. FACEBOOK: Earlier this month, some leaked emails reveal how Meta scrambled to keep Facebook "culturally relevant"—pitching tie-ins with Drake, new dating features, and even Taylor Swift content. Internally? Execs admitted teens were ghosting the app. A rough look inside the social media decline curve, also things that didn't help with a book from a Facebook Insider who alleges bad behavior coming in from the top. Facebook's attempt to stop the author from promoting or distributing the book backfired - as that news made the headlines on the book's front page. 10. CASE STUDY: This one is super useful (at least I'm well aware of it) if you ever find that you need to "warm up" a domain for bulk email or marketing purposes - Resend shares how they warmed up their new domain to send 3M+ emails/month without landing in spam land. Great tactics to pay attention to here include inbox seeding, ramp schedules, and IP warm-up. It also includes what NOT to do! POD OF THE WEEK: Hiten Shah discusses how smart founders, marketers, and leaders are using AI to win. 1. SaaS METRIC OF THE WEEK: Multiples. Valuation multiples are so important for determining a company's worth. But they also seem so mysterious as they vary wildly based on growth stage, industry, and deal size. Dealroom has a multiples valuation guide with some great visuals and charts to help us all understand this mysterious metric better and also make data-driven decisions.
2. ENGINEERING: Here is a sharp take on the identity shift ahead. Software engineers are facing a massive identity crisis in the AI age (and so are Product Designers). As coding commodifies (is that a word?), devs must shift from "builders" to "designers of intelligent systems." Product design shifts from crafting UI to orchestrating intelligent workflows. 3. CAPITAL: Non-dilutive funding is having a moment. Startups are increasingly turning to grants, revenue-based financing, and venture debt to extend runways without giving up equity. This post breaks down when and how to tap each one. 4. MARKETING: Do you also feel personally attacked by the title of this article, "You Suck at Marketing." As an operator wearing many hats, including marketing, I begrudgingly have to agree. Most of what works for us inbound, and the result of Content Marketing - so read this article from the team at Organic SaaS Growth on how to be less sucky at that. 5. PRODUCT: Product Compass has rounded up a bunch of the best Product management frameworks—from Jobs-to-be-Done to RICE—and shows how to apply them contextually (not religiously). An excellent resource for not just PMs, but people who want signal over structure. 6. SEED-STRAPPING: A new for our tech dictionaries: Seed Strapping is the middle ground between bootstrapping and blitzscaling—raising just enough to find product-market fit while keeping burn and dilution low. Smart, flexible, and, in this new kinda venture market, increasingly popular. 7. AI: Stanford University is back with a 2025 version of their Artificial Intelligence Index Report (the 2024 version can be found here). It's not a quick read. Private AI investment hit a record $252.3B, U.S. funding in GenAI alone hit $109B—12x China. 78% of companies are now using AI (up from 55%), inference costs (cost of running AI prod) dropped 280x in 2 years, but performance is plateauing, and the AI marketplace is getting cramped! 8. 12-FACTOR APPS: Another entry for your tech dictionaries, this framework laid the foundation for scalable, maintainable SaaS. From config to logging to dev/prod parity—it's essential reading for any of us building modern software. 9. AI STACK: Inspired by the 12-Factor Apps methodology in #8 above, this Git-Hub repo outlines what it takes to build 12-Factor AI Agents - from runtime modularity to tool use, feedback loops, and logging. If you're more on the techy-side and serious about deploying LLM agents in production, this is a great read. 10. CASE STUDY: ChatGPT doubled its weekly active users in <6 months, hitting 180M+. Credit goes to GPTs (custom bots), voice features, and Assistants API. Product velocity + sticky features = growth. POD OF THE WEEK: Adding onto #5 above, Tried and tested AI tools for product managers. Dave Killeen, VP of Product at Pendo, shares his go-to AI tools that can help make life a little easier for product managers. 1. SaaS METRIC OF THE WEEK: CARR - Contracted Annual Recurring Revenue. This is a forward-looking SaaS revenue metric that estimates a SaaS company's maximum revenue size, measuring current recurring revenue from your SaaS P&L and future revenue that sits in newly won customer contracts.
2. KNOWLEDGE BASE: I complain all teh time that building a comprehensive and useful customer Knowledge Base platform is hard. But here is something to really consider (it's certainly a helpful article for my mindset): There are probably stakeholders/purchases of your product who do not respond well to traditional marketing and, in fact, may actively hate it. These people are like me, and while I may moan about how difficult creating good documentation is, it may be one of the best anti-marketing-marketing tools you have available, Especially if you have an API as part of your product. 3. AI TEAMS: I brought up the idea of AI-first startups a few weeks back. But here is a great article on AI-first product teams. It's not just about adding AI features— it's rethinking how products are built. From architecture to staffing to shipping, the best AI teams blur the lines between data, design, and engineering. Great examples and org patterns 4. TARIFS: Last week was fun for anyone with a passive stock portfolio. Buckle-up Tariffs are here for who knows how long. CJ Gustafson nails the moment IMO: a two-day $6.6T hit to global equities and SaaS multiples dropping below 5x. Tariffs triggered it, but the future implications go deep—slower procurement, delayed renewals, and CFOs reverting to spreadsheets. Ruben Dominguez backs it up with details: tariffs on chips, EVs, and AI hardware are redrawing supply chains, squeezing margins, and will complicate GTM for startups globally. If you're building software, your customers may be hurting. If you're building hardware, you're already in the blast zone of this absurdity. 5. VENTURE: Let's see how #4 above will impact Venture because we WERE on a bit of a comeback. The new CB Insights State of Venture for Q1 2025 report is out, and VC funding reached the highest level in nearly 3 years at $121B - but deal count keeps falling. This is all led by OpenAI's mammoth $40B round. Annual median deal size is the highest it has ever been ($3.5M), and AI continues to reshape the venture ecosystem, driving 1 in 5 deals. 6. TERM SHEETS: ESG clauses hit 26%: HSBC's 2025 Term Sheet Guide breaks down 588 UK deals. Seed deals surged 46% YoY—driven by the good ol' AI buzz—while later-stage rounds saw tighter terms, more board controls, and a rise in participating prefs. 7. CLOUD: Notion Capital's 2025 Euro-centric Cloud Challengers list is out. 50% of the top 100 are (surprise surprise!) AI-native. Average team size? Just 16. Seed rounds surged to a median of $5.2M. Developer tools dominate, and PLG is going hybrid. 8. AI MODELS: (of the business kind) Check out this super interesting discussion centered on AI is breaking old SaaS economics. Legacy biz models show us where value will accrue: either let users own it (platforms), or fully outsource it (services). "Operate" plays are caught in the middle and at risk. 9. SALES: Need to boost conversions? Try Psychology. This post unpacks why buyers actually convert—highlighting the classics: urgency, FOMO, loss aversion, and more. Full of simple, high-impact tactics you can all steal today. 10. CASE STUDY: ChatGPT is one of the fastest-growing apps ever, and its parent company, OpenAI, is projected to hit $12.7B this year (up from $3.7B last year) and projected to hit $29.4B next year, but the organization still expects to lose money until it hits $125B ARR. Why? Infra costs are massive, and margins still look like those of hardware startups, not software. A killer reminder: scale ≠ profitability in AI (yes, yes we know about Deepseek). Also, the first-mover advantage normally doesn't play out well. POD OF THE WEEK: From David Kellogg and Co: CARR, ARR, and the Impact of Usage-Based Pricing. Contracted Annual Recurring Revenue (CARR) and Annual Recurring Revenue (ARR) are commonly used terms in the SaaS and Cloud Industry but are not standardized, leading to inconsistent calculations. 1. SaaS METRIC OF THE WEEK: CRO stands for Conversation Rate Optimization, and Banklinko has created a great web guide about what it is and how to design for CRO within a business.
2. MARKETS: Redpoint's March 2025 market update shows a public/private disconnect (due to IPO pipeline inactivity and investor cooling) - top software names are thriving, while most of the market lags. AI startups continue to raise at record valuations (up to 39% premiums), and time-to-$50B valuations is shrinking fast. Liquidity? Still slow, with most unicorns stuck in "Zombieland." 3. R&D: What if you cut R&D by 50%? Tomasz Tunguz ran the numbers - it turns out you'd only boost enterprise value by 3%. But if you grow revenue by 5%, you unlock 5x the value. TL;DR: cost-cutting is fine, but growth still reigns. 4. BILLING: ChartMogul's 2024 Billing Report breaks down all kinds of interesting billing benchmarks and trends: monthly billing is on the rise, but quarterly and annual still dominate revenue. Usage-based pricing keeps growing, and the best-run SaaS teams are doubling down on payment flexibility to boost retention and cash flow. 5. API: APIs aren't just dev tools—they're products, and pretty much all AI needs them. Zuplo's API guide lays out how to run API product management like SaaS, covering pricing, usage tiers, onboarding, and churn. If you've got an API, this gives you a roadmap. 6. APPS: Most SaaS companies pay other SaaS companies to build their SaaS company. It's a big ol' Ponzi scheme, and those SaaS costs are rising - currently $4,830 per employee/year, according to Zylo's new report. There is also some massive waste - an average of 52.7% of licenses are unused, and companies are still running vendor reviews looking to consolidate. AI-driven price hikes. Shadow IT, one-year contracts, and decentralized purchasing all compound this pain. 7. OUTCOME-BASEDSED PRICING: Another term for your AI Tech Dictionaries, outcome-based pricing. It's a pricing strategy tied directly to the value your product delivers to customers, very much a pricing model driven by the growth of AI. 8. PRICING: Based on 7 above, is it time for a pricing review? Great pricing can equal better growth. This post breaks down why pricing should be owned, not inherited—and why repackaging can outperform raising prices (such as Outcome based). Bonus: a dead simple framework for revisiting pricing without blowing up your funnel. 9. WRAPPER: We all rapidly became quite dismissive of startups with ChatGPT wrappers. But for all you Vertical AI integrators, give your wrappers even more thought. Without deep integration into existing B2B tools like CRMs or billing systems, your AI agents will probably fall short. Real power (and stickiness) lies in the data and workflows—exactly where vSaaS (new acronym y'all) incumbents thrive. 10. CASE STUDY: Wiz's $7B revenue-less exit to Google made headlines, but this breakdown shows the real winners: early employees and insiders. OnlyCFO estimates many engineers walked away with $10M–$50M+, making this a masterclass in cap table structuring and momentum-led outcomes. POD OF THE WEEK: Last month, I did the annual post sharing the "Shape-Up" technique for designing, prioritizing, and shipping products/features. So check this Podcast featuring the Shape Up creator, Ryan Singer, on how Agile/Scrum methods often lead teams into endless cycles of work without meaningfully "shaped" shipping milestones. 1. SaaS METRIC OF THE WEEK: Metric plot twist: Metric ownership. Metrics are only as good as the motivation to manage and measure them. Let's say you have done the hard strategic work and clearly understand the metrics you want to measure in your business. So go check this framework for assigning metrics ownership within teams. All that clear ownership helps drive better performance and data-driven decision-making.
2. GTM 1: Sure, inbound is great, but it is often not enough. MKT1's 2-part series on account-driven GTM lays out how to map your TAM, tier accounts, and track intent signals to engage buyers earlier and close faster. Includes tactical tips on CRM setup, signals, and org structure. Part 1 here and part 2 here. (there is a third part, but it's not out or not free just yet) 3. MARKETING: Check out this recent survey from Insight Partners. According to their survey, 70% of marketing-sourced pipeline comes from just four channels: SEO, events, social media, and paid search (and of those 4 SEO is under most pressure). Despite this, 50% of companies in the report are using 11-15 different pipeline-generating channels, many with minimal impact (combined 30% obvz). There are also some great benchmarks in there: Marketing drives almost half of the pipeline across B2B companies, Sales drives a third (33%), and Partners/Channel is 15%. 4. TYPING: I'm a sucker for a good blog title and also terrible at typing, so obviously and "The Rise & Fall of the Keyboard" hooked me. Tomasz Tunguz explores a future where voice and agents replace traditional input, making "typing" feel archaic. Hey - I already talk to my AI tools about 30% of the time, so as UX evolves, expect startups to rethink how users even interact. 5. VERTICAL AI: Vertical AI startups are changing how early-stage VC works—faster GTM, lower upfront costs, and niche market domination. Unlike broad AI plays, these companies win by embedding deep into industry workflows. Investors are adapting, and founder-market fit in these cases is more critical than ever. 6. SOCIAL MEDIA: Conquering social media in startup land is no joke, especially in the early stages when no real marketing team or specialists exist. So check this 11-step article (using SMART goals, which we all likely already understand). Regardless of the steps, Social Media is a metric-driven game, here is how to build out that part. 7. PMF: Something to bookmark time: Explaining Product Market Fit to potential customers, investors, and other stakeholders is tricky, so check out this free template using something called the Value Logic Framework, which helps founders articulate how their product uniquely solves a specific problem. I'm definitely going to take a crack at adopting this one. 8. DEMAND GEN: You always gotta look at this from the buyer's perspective, so let's dig into the stages buyers go through - from problem recognition to decision-making - you can tailor your strategies to align with buyer needs. The goal being the increase of engagement and conversion rates. 9. VENTURE: Between 2021 and 2024, the number of active US venture capital firms reduced by over a quarter, but startups are raising more cash than at any point since 2021 thanks to investor AI: $80B in Q4 '24, but 40% of that was spread over just six large deals (OpenAI, xAI, Databricks, etc). 10. CASE STUDY: An expansion of number 6 above is a list of five SaaS companies who are doing their Social Media well. Includes Hootsuite, Slack, and Shopify. POD OF THE WEEK: From SaaStr, how did Databricks scale from $1m ARR to $3B across sales, open source, pricing, and customer-led growth? 1. SaaS METRIC OF THE WEEK: ASP or Average Sales Price. ASP tracks the average price new customers pay when signing up. Unlike ARPA, which includes renewals and expansions, ASP spotlights initial deal size—a key signal for sales performance and pricing strategy. Track it by region, plan, or channel to optimize revenue growth.
2. THE END: No - not of this newsletter! But could the rise of AI tools, which are the ones achieving insane ARR growth (like $20m ARR in 2 months), signal a shift where software creation becomes democratized (by users)? There is definitely some food for thought in this article that outlines a current industry transformation that is blurring the lines between developers and users and possibly positioning software as a medium for personal expression and creativity. The future may see countless micro-startups addressing niche needs with tailored solutions? 3. AI AGENTS: Spinning off from number 2, (and also something I'm also working on), AI agents are poised to revolutionize SaaS by automating repetitive tasks and offering on-demand insights - but could they replace it, or how about a more hybrid approach - this article maps all that out, and this LinkedIn Article has a great visual! 4. AI STACK: Bolt was referenced in #2 above as a company that grew to $20m ARR in 2 months, but it's also a great case study in the new new. A really lightweight and fast, AI-first (See #5 below) company/ This structure rips the band-aid off some traditional constraints of headcount and dev cycles and also introduces a new stack to build a business on, the AI-Agent Stack. Shit is getting Agentic fast! Don't believe me? A quarter of startups in YC's current cohort have almost entirely AI-generated codebases. 5. AI-FIRST: My word this newsletter is turning into an AI-based one this week - but the "AI-First" approach is emerging as the new "Cloud-First" for startups. Unlike traditional SaaS targeting IT budgets, AI-first service businesses aim at labor costs, delivering services more efficiently through automation and task management. I think this is a pretty significant paradigm shift emphasizing the importance of integrating AI at the core of so many business models. 6. BPOs and AI: Business process outsourcing - is something many Enterprise (and SMBs) businesses engage in often around mundane or repetitive tasks. It's a $300B BPO industry primed for disruption by AI (and new-SaaS), according to this article from a16z. Customer support, back-office operations, and invoice reconciliation tasks can all be solved via AI, cutting costs while providing faster and more efficient scaling options. 7. BUSINESS PLAN: Finally, a non-AI post. Business plans!! Most business plans fail due to a skill set of founders: over-optimism, as well as a lack of adaptability and inadequate market understanding. Founders often overestimate their control and underestimate challenges, leading to misguided strategies. Recognizing these pitfalls and fostering a culture of flexibility and realistic planning are the big skills for success. 8. PROTOTYPE (AI): Back to AI again 🤖 (and Bolt - see #2 and #4). AI-driven prototyping tools like Bolt (and others like v0) are revolutionizing product development. The main reason for hype I think is that these platforms enable rapid iteration and real-time feedback, allowing teams to quickly visualize concepts, test functionalities, and refine user experiences. This accelerates time-to-market and reduces development costs, which in turn should be leading to more innovative and user-centric products. 9. MOATS: Moats used to come in all kinds of different flavors (such as speed, Brand, or growth), but as AI lowers those software development barriers I've mentioned in #2, #3, #4, #5, and #8 this week, traditional moats like complex software code are totally eroding. To maintain durable revenue and stay competitive, startups should focus on trust, unique data, and network effects (multi-product ecosystems, if you can build 'em, also help). 10. CASE STUDY: Big claim: The OG "Cloud-first" (see number 5 above) business, Salesforce, is freezing engineering hires in 2025—but also growing sales by 20%. Why? AI automates a lot of dev work, but selling AI-powered products still takes us humans. This signals a major shift across an organization: AI won't kill sales teams—it will make them even more essential. POD OF THE WEEK: Is there too much to read up there? 👆🏼 Listen to the Notebook LLM AI-generated podcast summarizing this week's newsletter for your commute home. 1. SaaS METRIC OF THE WEEK: Gross Dollar Retention (GDR) measures the percentage of recurring revenue retained from existing customers over a specific period (excluding any upsells or expansion revenue). It focuses solely on revenue lost due to customer churn and downgrades, providing insight into the stability of your customer base - high GDR indicates strong customer satisfaction and product value. To calculate GDR, subtract churned and downgraded revenue from starting MRR, then divide by starting MRR. For example, if you start with $1M MRR and lose $25K to churn and downgrades, your GDR is 97.5%.
2. SHAPE UP: This is the annual refresher for your tech dictionaries and reading list. Software product development requires innovative strategies based on today's cadence expectations of continuous integration, micro-services, feature delivery, and scale. The team at Basecamp (I'm an old-school fan) has developed ShapeUp, their publications, and toolbox of techniques designed to eliminate chaos when it comes to designing, prioritizing, and shipping products/features. 3. GROWTH: Coming off the back of last week's quite popular post on Growth Marketing - is it even marketing in the first place? I like this find, and I've been sitting on it a little while - but share it with your marketing team: The Strategic Growth Calendar Framework is a year-long blueprint that combines "Always On" growth channels with impactful "Marketing Moments." Emphasizing the integration of those steady, foundational channels like SEO and email with high-impact campaigns such as product launches, event, influencer collabs and the likes. Aligning these strategies with seasonal demand over your calendar year optimizes planning and (hopefully) continuous/steady growth throughout the year. 4. PRIVATE EQUITY: Private equity looks to be bouncing back after a two-plus-year slump. This McKinsey Global Private Markets Report 2025 report shows a 14% increase in global PE deal value, marking it the third-highest year on record. Distributions to LPs have exceeded contributions for the first time since 2015, which definitely signals renewed confidence. Large deals (over $500M) are on the rise, and financing conditions are improving, with new-issue loan values for PE-backed borrowers nearly doubling. But fundraising remains challenging, down 24% year-over-year, urging GPs to innovate in sourcing capital. 5. SPEND: Tropic's 2025 Software Spend Report is out and is just mashed with all kinds of goodies now that y'all follow Financial best practices and can report on total software spend and manage across different categories, right? The big takeaway is that spending jumped 10% YoY(not including any Fx for non-US businesses). Smarter buyers are consolidating tools. Enterprises still get the best pricing (and SMBs pay about 2x per seat in comparison). Fastest-growing vendors are your stock AI-first tools like OpenAI, Deel, and Notion. FYI - Price hikes are accelerating, so start renewal talks 180 days out and benchmark against this and your peers. 6. LAW: Always a goodie to repost, from CBInsights is a 67-page report covering the 11 laws driving success in tech. These law-isms cover concepts such as Amazon's 2-pizza rule, the 80/20 principle, and more. 7. DUE DILIGENCE (pre-seed): Pre-seed due diligence is all about people, cap tables, and corporate hygiene. Charles Hudson breaks down the red flags: ex-founders still holding equity, missing vesting schedules, messy SAFE structures, and unclear advisor stakes. Investors aren't just betting on ideas—they're betting on clean execution 8. VENTURE: According to this Substack, specialist VC funds (ones that invest exclusively in a specific industry, technology, or market niche) are 47% more likely to hit top-quartile returns than generalists. In today's market, depth beats breadth. Generalists chase hype and overpay, while specialists spot winners before valuations explode. 9. AI: All of our favorite (OpenAI, Anthopic, xAI, et al., well at least US Favorite) Foundation AI model startups are burning cash—OpenAI expects $4B revenue in 2024 but a $5B loss. The API model is looking like a commodity, and vertical integration is emerging as the only real moat. The future? AI apps, not just models. Whoever controls distribution wins. Which turns out (based on the Manus launch earlier this week) to probably be geopolitical bullshit. 10. CASE STUDY: Continuing on from #9 above, AI agents (hopefully) won't replace humans overnight: Accountability, context, and coordination are super necessary to work in IRL business environments. NFX breaks down how AI agents are being onboarded, such as employees, learning company processes, and integrating into workflows. The future of automation starts here. POD OF THE WEEK: From a16z, Creativity vs Control: Where AI Fits in the Creative Toolbox (and what happens when creative scarcity disappears and AI-generated content becomes ubiquitous). 1. SaaS METRIC OF THE WEEK: ARR. Two cool publications. The first one is "The Ultimate Guide to ARR," which offers practical advice on measuring, influencing, and reporting ARR based on experiences at Intercom, Atlassian, and Stripe; the second one is from Bessemer Ventures and claims to be a founder's roadmap to $100 million ARR.
2. GROWTH: ICONIQ's latest report on Growth and Efficiency is really insightful and reveals that top-quartile B2B companies are achieving 100% growth at $25M ARR, targeting 38% YoY revenue growth this year (up from 29% last year). They're achieving this by increasing investments in growth initiatives and keeping operating expense growth below half of revenue growth rates, aiming for that sweet spot of balanced focus on profitability and expansion. 3. MARKETING 1: A quick add-on to #2 above: testing new tactics of marketing growth takes up resources, and most of us are pretty time-poor for running experiments. So check this Google Doc from Dashly, where they collected 100 growth marketing hypotheses tested by a bunch of their experts. (includes advert retargeting, waitlists for product launches, niche glossaries, etc). 4. MARKETING 2: Where do Marketers feel most confident about getting an ROI from their campaigns? This article answers that for you - but the TL;DR - it's LinkedIn (and this is a survey of B2B AND B2C marketers) 5. UN-SCALE: I've talked about this a few times lately - we're all focused on building out that repeatable scaleable business model, but along the way, there are things that have to be done that are totally un-scaleable. This article highlights three specific non-scalable things sales teams should be doing right now. 6. TEAM: Check this stat: VCs say startup success depends on your TEAM DYNAMICS (56% of them), then timing (12%), and tech (9%). Tech sector likes teams more (64%) than healthcare (42%). 7. INVESTORS: Not all VC money is equal. Dealroom's report breaks down what we all already kinda know about what makes a value-add investor (those who do more than just write checks). The best? They offer hiring support, strategic GTM insights, deep industry connections, and help in closing enterprise deals. If your investor isn't opening doors, they're a dead weight. So check this article on drilling in more, don't ask VCs how they "add value." Instead, grill them on their win rate, portfolio support metrics, and founder success stories. If they can't answer, that's a red flag 8. VENTURE: Silicon Valley Bank's State of the Markets H1 2025 report is out and shows AI gobbling up Venture dollars. 48% of all VC funding in H1 2025 went to AI startups, with mega-deals skewing heavily toward the sector. Meanwhile, revenue multiples are down 10-50% from 2023, Series A valuations now take 2+ years to grow, and exits are still frozen—unless you're an AI unicorn 9. VENTURE MATH: Following from #8 above: Big funds = bigger problems. The Rule of 32 says a $5B VC fund needs $160B in exit value to hit a 3x return—more than Meta + Uber's IPOs combined. But with median exits shrinking 96% since 2019, and LPs paying $1B in fees before carry even kicks in, incentives are breaking. The math no longer works—neither does the game. 10. CASE STUDY: It's a common tech-ism from the tech industry that innovation needs a lot of failure before success, something they often do not configure culturally. CB Insights has analyzed almost 500 startup failure post-mortems - PMF, Cash, and Team Dynamics (see #6 above!) play pretty consistent roles across the board. POD OF THE WEEK: Funnel and revenue math kindly explained by Mark Roberge and Matt Plank of Rippling in the Science of Scaling podcast. 1. SaaS METRIC OF THE WEEK: Net Dollar Retention is an essential metric in product-led growth and consumption-based operations. It's used to help answer the following: Does my startup need to increase customer acquisition/marketing spend? Crunchbase crunched the numbers to calculate what good NDR benchmarks should look like, and Tomasz Tunguz looked at what it takes to achieve 200% NDR!
2. AGILE MARKETING: Agile processes are coming for ya marketing people! This is another one for our Tech Dictionaries - it's how to really validate learnings, make mistakes, and deliver impactful results. Hubspot covers this concept in detail and outlines how DoorDash hardcore leveraged this methodology to increase revenues from $885m to $2.89 billion in just ONE year! 3. ESOP: Employee Share Option Plans are a great idea to incentivize and retain great staff, but under the hood, ESOPs are complex, especially with changing valuations, both positive and negative, in today's market. So here are some great resources for you: 1. Data-driven VC's ultimate guide to startup equity breaks down everything from vesting schedules to tax implications. 2. Airtree Venture's best practices for communicating the value of ESOP to teams - this article also has a bonus financial model template (value calculator, salary package calculator, and vesting schedule). Check this cheat sheet for common ESOP terms. 4. ESOP BENCHMARKS: A fast follow from above is this site that has complied a set of Option benchmark data (taken from 20,000 option grants across 1,650+ startups across the US and Europe) - this is all sorted by Seed or Venture stage. Last year, Carta did the ESOP math and found that for seed-stage valuations ($1M to $10M), the median pool size is 12.9%. 5. UNDERSELL: If expansion fits into your growth strategy (it should btw), take a read of the two-part series from Tomasz Tunguz and Bill Binch - part one is deliberately underselling as a sales strategy to minimize churn and increase upsell/expansion opportunities as a land and expand strategy and post 2 is an expansion of land and expand witch details how to structure a Startup sales team for optimal land & expand. 6. FOUNDER-LED SALES: Founder-led sales is a well-documented part of the startup journey, especially in the early days, and often with very inexperienced or more technical founders. Here is a great article (with Engineering-based analogies) on how Founders can mentally re-frame and execute an excellent sales program. 7. GTM: Early-stage startups waste time when sales and marketing aren't aligned. ChartMogul lays out how to tighten your ICP, unify messaging, and avoid the classic trap of marketing generating leads sales can't close. 8. SEO 1: SEO is under some pretty interesting changes. Google's new AI Overviews are changing how users interact with search results (which is reducing click-through rates). New acronym time, apps like ChatGPT and Claude focus on EEAT-ing you (Experience, Expertise, Authoritativeness, and Trustworthiness). User-generated content is also becoming a significant factor in search rankings. 9. SEO 2: Choosing the right keywords is one of the major levers for SEO success, and it's super hard to figure out. Focus on highly relevant terms, proper search intent alignment, manageable competition, and significant search volume. If you need to figure out your SEO monthly tasks (like analyzing organic traffic patterns, evaluating rankings, and optimizing outdated content), take a read of this article to get you started. 10. CASE STUDY: Outreach (the Company) didn't scale by accident—it followed a 5-phase GTM framework to dominate their space (sales engagement). From early adopter focus to repeatable sales motions and strategic market expansion, this breakdown shows exactly how they did it. POD OF THE WEEK: From Lennys Newsletter is an insightful and entertaining podcast with growth-guru Elena Verna (dropbox Mire, SurveyMonkey) covering 10 growth tactics that never work (and 3 of her favorite frameworks that do). 1. SaaS METRIC OF THE WEEK: Fundraising Metrics. Make your fundraising way less chaotic by getting these metrics dialed in. Unless you are pre-revenue, Investors will expect to see detailed ARR, CAC, LTV, retention rates, and engagement metrics. A strong data deck (or data room) can answer investors' questions and show a clear path to growth.
2. PPG: Tech dictionary time - another acronym for you: PPG or People Powered Growth. This is a derivative of product-led growth, which consists of a cross-functional team with both customer-facing and non-customer-facing members. It's a People + Product partnership that develops and tests solutions, searching for ways to scale human interactions/intervention with a product. Some examples of PPG companies are Drift, Dropbox, and Loom. 3. PRODUCT-MARKET FIT: Finding Product-market fit isn't a one-and-done event—just like the product you ship, it's an ongoing process. This updated playbook breaks down the key signals, from retention curves to sales velocity, and the tactical moves to iterate faster. If you're still guessing, this is your roadmap. 4. MARKETS: Carta's Q4 2024 report is out and shows a fairly dynamic shift in private markets. Early-stage startups saw a 36% drop in deal activity. Series D rounds are up 60% YoY, and Series C bridge valuations doubled! Hopefully, this will give investors confidence in scaling ventures. Despite early-stage declines, median valuations rose by 22%, and M&A activity hit a record high, with 333 deals in 2H 2024. 5. FREEMIUM: AI is sparking a freemium renaissance in SaaS, according to Jason Lemkin. OpenAI and Claude offer robust free tiers, setting new customer expectations. Established players like PagerDuty, HubSpot, and Cloudflare are doubling down on freemium models to drive growth and enterprise pipeline. With AI costs plummeting, embracing freemium is both feasible and strategic. 6. GTM 1: Bookmark and take a read of these 25 automated GTM plays you're probably not using—but should be. From reviving closed-lost deals to automating expansion motions, this list can help your teams rethink your GTM plays for sure! 7. GTM 2: Fast follow from above, Enterprise GTMs are a lil' different, as they aren't just about sales—it's orchestration. This article breaks down the critical pillars: cross-team alignment, stakeholder mapping, sales productivity, and support structures that make or break frustratingly complex deals. 8. INFRASTRUCTURE: The AI boom has a very unique platform architecture compared to prior tech booms, and this article explores the next wave of data infrastructure companies that will be built for AI-scale efficiency. As a former platform geek, what's cool is that energy efficiency, new compute architectures, edge initiatives, and novel go-to-market motions are all going to be needed. 9. SCALE: Hitting $1M ARR is part luck and part product (and PMF), but you don't get there without execution. Bessemer Ventures breaks down what separates those winners: selling before building, picking the right GTM motion early, and ruthlessly qualifying customers. If you're grinding through the early days, this is a solid playbook 10. CASE STUDY: Series B+ raises. Most of us should be so lucky to get to this stage, but how do you raise funds beyond Series B (roughly 15% that raise seed make it to Series B)? Scale Ventures' Stacey Bishop gives the lowdown. POD OF THE WEEK: Why read when you can listen to this? Leveraging Notebook LLM again for the podcast version of this week's newsletter - but the AI cannot pronounce "SaaS." 1. SaaS METRIC OF THE WEEK: Share of Wallet. This is a fun one for all you marketplace people (who should also check this other article on Marketplace Liquidity). Share of Wallet is a measure of a marketplace going from being one of many options to becoming the primary option for a buyer (AND also a supplier).
2. ADVISORS: Startups need them; often they can be a little overly plentiful and somewhat predatory. If you find a sound advisor, how should they be compensated? Peter Walker from Carta has some data for you. TL;DR market rates are 0.23%-0.07% median based on stage unless full-time hires, who get 1% typically. 3. VENTURE: Dealroom's latest Global VC report reveals a mixed venture landscape. Startups raised $330B globally in 2024, with megadeals ($100M+) making up 53% of investment. The U.S. dominated, claiming 57% of global VC funding, mainly AI-driven. Meanwhile, early-stage funding slowed. 4. PRIVATE MARKETS: Mostly Metrics has looked into the current state of private markets at EOY 2024 SOY 2025. Much of the same, really - slower deal activity, cautious investors, and a shift toward profitability over growth. Despite the slowdown, AI continues to attract capital. 5. AI: Nice handoff from #3 and #4 above, AI startups have and are rewriting the fundraising playbook. But when can we all expect AI-based economic growth, and how much? This article backs the sentiment by outlining that 2025 should be the year of killer AI apps. 6. AI and JOBS: Bonus content expanding from above - this article has looked at the impact of AI across different tiers of AI and tech sector unemployment. Is it feeling the flow on? IT unemployment rates rose to 5.7% in Jan from 3.9% in Dec (that's a 46.15% change, according to ChatGPT). This same article also shows that job listings for Devs are down -8.5% YoY in Jan 7. GROWTH: Kalungi's Growth Matrix shows how to pinpoint hidden opportunities by plotting segments and adoption stages. It's an excellent four-step process that helps you focus and even comes with a template. 8. FUNDRAISING: What does it take to raise a Series A? How do you break through the $10M ARR barrier and secure growth capital? More Intelligent has a great guide along with must-hit fundraising milestones—from scaling your go-to-market motion to tightening unit economics and KPIs. 9. DRAKE EQUATION: No, Kendrick isn't involved with this; it's for your tech dictionaries. The Drake Equation was originally used to estimate alien civilizations (totally my jam) and calculates success by multiplying probabilities of key factors. This article adapts it to startups—highlighting how market fit, execution, and scalability shape your survival odds. 10. CASE STUDY: Deel's on a growth rocketship right now —70% YoY at $800M ARR (AND profitable). This proves that in SaaS, market share isn't everything when your TAM is massive. SaaStr analyzes Deel's strategy, focusing on category expansion and prioritizing global scale over head-to-head competition, and it looks like they may be able to kickstart Tech IPOs again. POD OF THE WEEK: This is such a great article covering day-to-day AI use that I used Notebook LLM to turn it into a Podcast. 1. SaaS METRIC OF THE WEEK: CAC - in a modern SaaS world that has maturing companies using both Sales Led Growth (SLG) and Product Led Growth (PLG) motions and teams, how do you calculate CAC? The answer is, really, they should be kept separate (see Pod of the Week for more below).
2. PLG vs. SLG: According to the Expansion SaaS Benchmarks report (it's a downloadable PDF), PLG businesses lead the pack, but as stated above, SLG can outperform PLG. According to this article, it's not a "vs." thing—you don't have to choose; both strategies can coexist. 3. BOARD: Mostly Metrics delivers a three-part series on running effective board meetings, covering roles and responsibilities, prepping killer materials, and locking in more discreet updates. 4. MARKETING: We all want to run a high-performing marketing team. MKT1 breaks down that Operating Cadence - how to set the right rhythm for planning, execution, and iteration. From weekly stand-ups to quarterly reviews. This is a super helpful framework to keep all your marketing bits aligned and moving fast. 5. R&D: Research and Development is a major component of any competent Software startup, and often, public R&D incentives (via Grants, Tax breaks, or deductions) align well at the difficult early and growth phases. So, how do you measure if your R&D spend is actually paying off? Mostly Metrics breaks down key efficiency metrics—like R&D as a % of revenue, time-to-market impact, and capitalized vs. expensed costs—to help SaaS leaders optimize innovation investments. 6. CORE 4: Adding onto #5 above is a new framework for your tech dictionaries, Core 4. a pretty powerful (but simple) way to prioritize R&D investments. Instead of spreading resources thin, focus on four core product bets that drive real impact. 7. FACILITATE: A super fun and VERY bookmarkable resource this week. It's a library of tools available to facilitate your next session with people or a team - team building, brainstorming, ice-breakers, check-ins. They are all there! 8. PREDICTIONS: Dave Kellogg's 2025 forecast anticipates continued challenges in the startup ecosystem (yay!), with a stock-standard focus on efficient growth and the rising influence of AI. But he also predicts that LinkedIn may face challenges in maintaining its professional focus amid increasing non-work-related content (why Videos Linkedin? Why?). Additionally, Kellogg discusses the potential for increased division in the U.S. political landscape (check!) and the evolving role of public relations in the era of AI-driven content. 9. MARKETING: eBooks are dead? According to Hubspot, SaaS marketers are pivoting to (free) mini-tools that actually solve problems and add value. Read more about how to get started in that article as well. I guess marketers found the loss leader they've been looking for, and I should start sharing more. 10. CASE STUDY: The GTM Newsletter reveals Outreach's 5-phase GTM framework that drove their growth. This article covers $0-$230m ARR and covers early experiments, scaling tactics, and strategies that cool framework. POD OF THE WEEK: To marry #1 and #2 above from the SaaS CFO Calculating CAC when you have PLG and SLG motions. 1. SaaS METRIC OF THE WEEK: NRR is one metric that has become a new modern gold standard for SaaS growth (see Pod of the Week below). So much so that ChartMogul has a trends and benchmark report: industry average NRR ranges from 90% to 100%, and the top-performing SaaS companies achieve NRRs 120%+. It's an action-packed NRR report, though - lots of fantastic insight.
2. EXPANSION: Expanding from above (get it???) - NRR and expansion strategies are pragmatic and capital-efficient growth practices that any good SaaS company needs but are getting harder to come by. Top quartile companies have been hit hard, seeing NRR drop from 119% to 107%. But at scale, more growth is coming from expansion vs. new. The proportion of ARR gained from expansion has increased from 28.8% in 2020 to 32.3% now. In comparison, the proportion of ARR gained from the new business has fallen from 62.0% to 57.9%. 3. TRIGGER TECHNIQUE. This is a new entry for the Tech Dictionaries; The Trigger Technique outlined in this article shows how to leverage customer interviews to learn what "triggers" potential customers' buying decisions. This information helps design more targeted marketing campaigns and boost sales. 4. RETENTION: Can your retention rate be too good? This is an interesting question this week, and Mostly Metrics explores the (surprising to me) downsides of high retention rates—like stifled growth and untapped revenue streams. It's well worth a read just as a reframing exercise. 5. AI part 1: Unless you were living under an AI rock this week, you may have noticed that a new AI Model, DeepSeek, stole the show, showing us all a few things: First mover advantage usually doesn't play out too well, constraints are a ripe spot for innovation (in this case US sanctions on Chips) and that AI commoditization was inevitable. It also ripped deep into the already established AI markets, giving Nvidia the most unwanted crown of the "biggest market loss In history" (about $600B). Yay to everyone's Stock Portfolio! 6. AI part 2: Fast follow to #4 above; Benedict Evans breaks down the real issue with AI models: it's not enough just to be better. As AI commoditization accelerates, differentiation shifts from model capabilities to distribution, UI, and product integration. The AI gold rush isn't just about who builds the best model—it's about who owns the customer (and why first-mover advantage is generally problematic) 7. AI part 3: This is a repost from a newsletter section late last year, but very relevant to #4 and #5 above this week. Every year, Benedict Evans goes on an absolute blinder in PowerPoint, exploring macro and strategic trends in the tech industry. This year's version (across a 90-page slide deck) is all about AI (again, as last year's presentation was "AI, and everything else"). This year's post is about the post-hype investment surge where proven market value hasn't yet been firmly established (by that, I mean investment vs. Value Creation), which Deep Seek may be close to cracking. He wrote this in November and noted back then (which seems to be like 5 AI years ago) that scale is hard and REALLY expensive, which limits competitiveness (until last week). Slide 59 is the best TL;DR: The future can take a long time - unless US sanctions provide the ripe, constrained environment for quick innovation. 8. FRICTION LOGS: Another addition to your tech dictionary. Software and product design are never truly finished. Friction logs track every pain point in a product experience, helping teams pinpoint issues and refine UX. Want to set one up? Here's a solid guide on how to do it right. 9. VENTURE: The Q4 2024 PitchBook-NVCA Venture Monitor shows a venture market still in limbo. Exit activity remains really weak, with only 3.6% of exits exceeding $500M, but optimism is creeping back for 2025? High dry powder levels, a handful of strong IPOs, and potential rate cuts could shake things up, but valuation expectations are still holding back the IPO market. 10. CASE STUDY: Is growth still good? Ben Thompson tackles the "growth at all costs" dilemma with real-world examples from Meta, Uber, and Tesla. He unpacks how aggressive scaling strategies are now clashing with regulation, shifting market expectations, and economic reality—making sustainable growth the smarter play. POD OF THE WEEK: From SaaS Stock, a podcast covering what makes a Founder, not a startup. investible (TL;DL) it's founder compatibility, and also companies with an efficiency edge, strong GTM potential and the right metrics (especially NRR - see #1 and #2 above). |
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