SaaStr

MAY 8, 2024

As a SaaS veteran who built and sold a software company for nine figures, invested in startups since 2013, 10x-ing his fund, and continues to build a powerhouse community of SaaStr fans, he offers some hot takes on the communities’ burning questions. What metrics should we expect in this environment? Let’s start with the meta. “I

Metrics 272

Metrics Scale Sales Hiring SaaS 272

Clouded Judgement

NOVEMBER 18, 2024

The purpose of the detailed information is to help investors (both institutional and retail) make informed investment decisions. ”” Benchmark Data The data shown below depicts how the ServiceTitan data compares to the operating metrics of current public SaaS businesses.

Benchmarks 299

Benchmarks Payments Payment Services SaaS Payments 299

SaaStr

DECEMBER 20, 2024

Having led sales teams of 500+ at BILL and 800+ at HubSpot, Michelle has unique insights into what makes great frontline managers and why investing in them is crucial for sustainable growth. “At HubSpot, I had over 100 frontline sales managers reporting to me. Robust Measurement Effective measurements is really effective management.

Sales Hiring 260

Sales Hiring Scale Underperforming Technical Team Sales 260

SaaStr

DECEMBER 4, 2022

It created a lot of discussions and was more controversial then — that NPS was a great core metric. Back then, I wrote that when I was a SaaS founder, I thought Net Promoter Score (“NPS”) was a somewhat dumb, Big Company metric. I didn’t want a metric that was abstracted away from revenue. I was wrong.

Metrics 293

Metrics Churn Engineering Innovation 293

SaaStr

DECEMBER 17, 2024

All of which are epic companies with epic metrics. Some rough metrics for the last 4 SaaS IPOs — which again are epic ones: These are rough metrics. But overall, the growth investments weren’t big wins. I didn’t include antidilution protections to keep it simple. At least at IPO. Does this really matter?

SaaS 261

SaaS AI Pricing Metrics 261

SaaStr

AUGUST 9, 2022

Investments I've made that didn't work out: – Momentum investment – CEO a bit of bulls**t artist – CEO good at sales but weak product team / CTO. Investments I've made that had so-so outcomes: – CEO not better than me – CEO couldn't control burn rate – Not really SaaS.

Investment 307

Investment Sales Recruiting CTO Startup 307

SaaStr

MAY 3, 2024

What are the three most under-discussed metrics on social media, with VCs, and especially with founders? They went from on-prem to a SaaS model and may flatter their metrics a little by confusing them. This should be your North Star metric. Invest in your long-tail; don’t give up on champions and smaller customers.

Metrics 300

Metrics SaaS Scale Social Media 300

SaaStr

SEPTEMBER 23, 2022

Dear SaaStr: How Does SaaStr Fund Decide What to Invest In? Let me give my investing process at least for SaaStr Fund : First, I try somehow to identify before a first meeting if there is a >=2.5% chance of investing. Second, I then look for reasons not to invest. No matter how appealing the investment is otherwise.

Investment 301

Investment Startup Metrics Software 301

SaaStr

NOVEMBER 19, 2024

But I’d say 90% of SaaS companies I work with and have invested in don’t get these basics right for a long, long time. NPS is A Great Core Metric. Yes, a lot of this sounds basic. Not for real. More here: If Nothing Else – Segment Churn | SaaStr and I Was Wrong.

Churn 270

Churn Retention Scale Investment 270

SaaStr

OCTOBER 31, 2023

Dear SaaStr: What Did You Learn From Your Worst Venture Capital Investment? You can’t keep investing in the same companies, at the exact same stage, same valuations, etc. When I’ve cut a corner here and invested in startups with customers that aren’t super-happy, it hasn’t worked out as well. But the NPS/CSAT has to be there.

Venture Capital 273

Venture Capital Investment CTO Churn 273

SaaStr

OCTOBER 25, 2024

It’s now falling to 150 because 81% percent of the dollars invested in venture capital at the height of the boom came from non-traditional venture capital firms which are all very likely to leave investing. It’s to say many of us do not know how to use AI effectively enough yet to impact conversion metrics. #6:

Venture Capital 331

Venture Capital Marketing AI SaaS 331

SaaStr

NOVEMBER 15, 2022

Metrics are the key to evaluating success and setting goals, but not every SaaS business should orient itself around the same one-size-fits-all numbers. This flexible mindset creates just the right conditions for embracing evolving business models and new metrics. The Metric Monolith: The Rise and Fall.

Metrics 272

Metrics Machine Learning Artificial Intelligence Technical Review 272

User Pilot

NOVEMBER 29, 2024

Many companies invest heavily in acquiring new customers, yet still struggle with growth. Dan, a Stanford-trained engineer with experience guiding companies like Intuit, understands how to optimize your product metrics for growth by focusing on retention and building a product users truly value. At first glance, they look identical.

Metrics 105

Metrics Scale Acquisition Retention 105

SaaStr

NOVEMBER 20, 2024

Other places this feedback loop worked well were: Adoption loop metrics. Customers crave metrics about how teams are using all AI products. Don’t underestimate the investments you need to make here to be compelling to your customers. Another big investment during rapid growth is digital moments.

Scale 261

Scale AI Scaling Marketing 261

SaaStr

DECEMBER 3, 2023

So over the past decade-and-a-half we’ve come up with a lot of yardsticks, metrics and rules for SaaS companies. E.g.,: CAC of < 12 months is Good-to-Great Paying sales reps 25%-30% of what they close is Good A burn ratio of 1 or less is Good These metrics do sort of work, if you have some capital to spend (i.e., They don’t.

SaaS Payments 278

SaaS Payments Metrics SMB Payments 278

SaaStr

NOVEMBER 10, 2022

Dear SaaStr: What is the Process You Follow When Investing in an Up-and-Coming Startup? chance of investing. The single most important thing you can do is protect your “slots” so that you meet with startups there is at least some chance you might invest in. Second, I then look for reasons not to invest. But others won’t.

Investment 284

Investment Startup Metrics Software 284

SaaStr

MARCH 23, 2025

Be explicit about success metrics Define what success looks like beyond revenue targets to align expectations. Invest early in supporting functions Don’t underestimate the importance of enablement and revops in driving growth. We let sellers ramp without proper resources for too long, which cost us deals and momentum.

Sales Recruiting 242

Sales Recruiting Sales Hiring Scale AI 242

SaaStr

APRIL 6, 2025

Celebrations are shifting from contract signatures to consumption metrics – Their team is evolving beyond celebrating closed deals to automated alerts for customer usage milestones, fundamentally changing what success looks like. This created personal investment and accountability that no executive mandate could achieve.

Scale 202

Scale Sales Hiring Sales Outsourced Development 202

SaaStr

FEBRUARY 14, 2023

In this week’s Workshop Wednesday , Salesforce Ventures Investor, Jessica Bartos, shares the 5 metrics every SaaS company should care about in any market environment, especially the one we’re currently in. Growth Is Still Number One Growth is still the number one metric, but it’s not the only one. They’re simple but not always easy.

Metrics 261

Metrics Marketing SaaS SMB 261

SaaStr

OCTOBER 31, 2023

— Jenny Fielding (@jefielding) October 17, 2023 So one of the parts I like least about investing is the follow-up. A few times a year, I’ll meet founders and a company I believe in so muc h, I’ll clearly offer to invest at the first meeting. Specifically, the follow-up when I’m not sure. That Almost No One Asks.

Investment 273

Investment Metrics Sales 273

SaaStr

MARCH 9, 2025

Meeting intensity KPI challenge : Sometimes AI efficiencies can reduce a company’s core metrics (like Calendly’s “meeting intensity”), requiring leadership to make conscientious decisions about value tradeoffs. Building separate AI interfaces can create unnecessary tech debt and learning curves.

AI 202

AI Scale Education User Experience 202

SaaStr

MARCH 24, 2025

If you’ve used Zendesk, Algolia, Contentful, or Loom, you’ve experienced the impact of his investment thesis firsthand.

Data 147

Data Acquisition AI Finance 147

Clouded Judgement

MARCH 21, 2025

Given most software companies are not profitable, or not generating meaningful FCF, it’s the only metric to compare the entire industry against. I created this subset to show companies where FCF is a relevant valuation metric. This is for information purposes and should not be construed as an investment recommendation.

Cloud 188

Cloud Pricing Subscription Payment Features 188

SaaStr

FEBRUARY 7, 2025

They: Started with clear use cases Built a strong data foundation Focused on measurable customer value Invested consistently over time Maintained a human-centric approach For SaaS companies looking to leverage AI, the key is to start building your data advantage now, even if you’re using third-party tools.

AI 262

AI Scale Government compliance 262

SaaStr

MARCH 18, 2025

The result was a 5x increase over initial projections – growing from an $8M revenue target to $40M actual results – driven by a belief that market demand justified the investment. This approach required immense trust from the CEO to invest millions ahead of proven results.

Scale 185

Scale Sales Hiring Scaling Headcount 185

SaaStr

SEPTEMBER 25, 2024

What data and metrics do you need to convince SaaS investors you’re in good shape and aligned with what they care about? These metrics are more targeted to those preparing for a Series A or B round and could make the difference between an excited-to-invest-in-you investor and a pass. They’re looking for excellent retention.

Metrics 184

Metrics Sales Hiring Retention Churn 184

Clouded Judgement

MARCH 28, 2025

That juxtaposition is what makes investing in venture markets these days so fun! Given most software companies are not profitable, or not generating meaningful FCF, it’s the only metric to compare the entire industry against. I created this subset to show companies where FCF is a relevant valuation metric.

AI 184

AI Cloud Scale Scaling 184

SaaStr

JANUARY 23, 2025

But the rewards – higher retention, bigger deals, and ultimately a much larger TAM – make it worth the investment. Focus on Land-and-Expand Economics Don’t obsess over initial deal size. The Bottom Line Moving upmarket successfully requires intentional planning, the right team, and relentless execution.

Enterprise 244

Enterprise Sales Hiring Scale Outsourced Development 244

SaaStr

JULY 20, 2024

Metrics, Metrics, Metrics The first thing Secureframe thinks about is metrics. If you don’t know your key company or North Star metrics, talk to your investors or other experts to figure out what they should be. So they can take action on the metrics in real time if they’re going in a direction they don’t like.

Sales Recruiting 299

Sales Recruiting Sales Hiring Scale Engineering 299

SaaStr

AUGUST 7, 2023

Learn about the most important SaaS metrics for founders in 2023 with the CEOs of the most metric-oriented company, monday.com, and the founder of SaaStr. For a quick recap on SaaS metrics: What is ARR in SaaS? Then the Boom happened, and everyone could justify insane investments, and it warped everything.

Metrics 245

Metrics SaaS Sales Hiring Finance 245

Clouded Judgement

DECEMBER 20, 2024

Given most software companies are not profitable, or not generating meaningful FCF, it’s the only metric to compare the entire industry against. I created this subset to show companies where FCF is a relevant valuation metric. This is for information purposes and should not be construed as an investment recommendation.

Cloud 144

Cloud Banking Payment Features Subscription 144

SaaStr

FEBRUARY 25, 2025

Sessions typically focus on real metrics, strategies, and lessons learned, not theoretical concepts. In addition, this year Mayfield is sponsoring our VC AI Pitch Stage and will invest from $500k-$5m in the winner! Meet and Find Your Next VP / CXO! Many vendors offer special event pricing or extended trials, creating additional value.

Sales Recruiting 195

Sales Recruiting Scale CTO Hire Sales Hiring 195