SaaStr

JUNE 4, 2025

The 40% Problem: How AI Will Finally Fix Sales Coverage and Customer Face Time A wake-up call from HubSpot’s CEO Yamini Rangan on why your sales team is failing 60% of their accountsand how AI will change everything There’s a brutal truth about B2B sales that most founders refuse to acknowledge. Think about that for a moment.

Scale 225

Scale AI Underperforming Technical Team Sales 225

SaaStr

JULY 30, 2024

Okta’s VP of Engineering, Monica Bajaj, and Senior Director of Platform Product Marketing, Priya Ramamurthi, share Okta’s playbook to PLG, developer experience, and Enterprise ARR. How do you build a stellar developer experience and continue to scale when the user base skyrockets overnight? Let’s start with product-led growth (PLG).

Underperforming Technical Team 281

Underperforming Technical Team Enterprise Scale Payments 281

SaaStr

NOVEMBER 25, 2023

Jameson Yung, SVP of Sales at Gong, and Sam Blond, Partner at Founders Fund and previous CRO at Brex, share five tactical ways to get back to growing and hitting revenue targets. The days of working a little for big returns are behind us in the Boom of ‘21, so what can you do to start hitting revenue targets? #1: Revenue matters, too.

Sales Hiring 272

Sales Hiring Underperforming Technical Team Revenue Sales 272

SaaStr

MARCH 12, 2025

About Dave Kellogg Dave Kellogg brings a rare combination of marketing and executive leadership experience to his analysis of SaaS businesses. A smaller number of high-quality leads that convert at higher rates is vastly superior to a flood of poor-fit prospects. But here’s the reality check: this is completely normal in SaaS.

Sales Hiring 190

Sales Hiring Marketing Technical Review Underperforming Technical Team 190

SaaStr

MARCH 30, 2024

Dear SaaStr: What are The Most Common Mistakes Founders Make When They Are Just Starting to Scale Revenue? Then, you’ll have enough folks and experience to put a small team on a new initiative / segment / market. Micromanaging Your First (and Second) Management Team. Bad operational model / misunderstanding the burn rate.

Scaling 301

Scaling Revenue Underperforming Technical Team Market Segmentation 301

FastSpring

JANUARY 23, 2025

If you own a SaaS or other digital product business such as a Slack plugin, Chrome extension, online publishing business, mobile app, or even a blog and youre looking to exit, you may have a lot of questions about how best to go about it. So I’ve worked in SaaS businesses that were fast growth. And I’ve done that.

Scale 118

Scale Entrepreneurship Scaling Underperforming Technical Team 118

SaaStr

OCTOBER 4, 2024

In today’s dynamic SaaS landscape of hyperfuncational SaaS, the journey of building a product that customers adore, while simultaneously scaling revenue to nearly $1B, is still quite a feat. More on that here. So how did Klaviyo do it? At the time, Shopify was still a new player. What product would you recommend?

Revenue 307

Revenue Scale Underperforming Technical Team Sales Hiring 307

SaaStr

FEBRUARY 16, 2025

While competitors invested in huge sales teams, Atlassian actually restricted direct customer interaction. The “Feature Request Arbitrage” Strategy Hidden gem in their marketplace origin: They turned their biggest product weakness (feature request backlog) into their greatest strength. The common thread?

Sales Recruiting 196

Sales Recruiting Marketplace as a Service Underperforming Technical Team Scale 196

SaaStr

APRIL 13, 2025

” Cross-selling generates $5M+ in new monthly revenue – Rippling’s cross-sell motion alone drives over $5 million in net new ARR each month before counting any new customer acquisitions. In the world of SaaS, conventional wisdom has long dictated that focus is paramount. Today, every space has multiple competitors.

Startup 157

Startup Sales Hiring Underperforming Technical Team Cloud 157

Stax

APRIL 15, 2025

For subscription-based businesses achieving consistent and predictable revenue growth is the holy grail. In fact, monthly recurring revenue (MRR) is one of the most important metrics subscription businesses should be aware of. TL;DR MRR is the average revenue that a company expects to receive each month.

Payments 88

Payments SaaS Payments Revenue Payment Services 88

SaaStr

JUNE 7, 2021

While it can be frightening to think differently, doing so has helped him make Veeva the biggest vertical SaaS success story of all time. If you don’t have tickets, lock in Early Bird pricing today and bring your team! That makes up about 35 percent of our revenue now. I was a software developer, a product person.

Sales Hiring 339

Sales Hiring Underperforming Technical Team SaaS Headcount 339

SaaStr

JANUARY 24, 2024

Mark Roberge , SaaStr fan-favorite and Co-Founder and Managing Director of Stage 2 Capital brought together some of the top CROs in SaaS during the SaaStr Annual to share some of their greatest learnings and pivotal moments leading some of the Cloud 100 SaaS companies. The bad news is it wasn’t driving the results they wanted.

Scale 273

Scale Sales Hiring Scaling Revenue 273

SaaStr

NOVEMBER 25, 2020

Both are two of the most impressive and inspiring public SaaS CEOs — but their products and companies couldn’t be more different. One was to get a sense of what the bar was to pull off a successful SaaS IPO these days (answer = oh man, very high). Do you have two sales teams? I wish I had some magic answers.

Underperforming Technical Team 356

Underperforming Technical Team Cloud Revenue Acquisition 356

Tom Tunguz

JANUARY 23, 2023

I’m watching public company earnings to identify early weaknesses in the software market. Azure ML revenue alone has increased more than 100 percent for five quarters in a row 4. Microsoft’s Ability to Cross-Sell its Suite is Driving Dominance in Many Categories GitHub is now home to 100 million developers.

Azure 256

Azure Underperforming Technical Team Artificial Intelligence Machine Learning 256

Stax

MARCH 16, 2025

That said, industry experts agree that your SaaS companys goal churn should be below 2%. As a SaaS business leader, reducing software user churn is an important part of maintaining your customer base and increasing revenue. TL;DR The average software industry churn rate is 14%, but SaaS companies should aim for under 2%.

Payment Solutions 88

Payment Solutions Software Review Churn SaaS Payments 88

SaaStr

JULY 10, 2021

So let’s take a look back to a deep dive with the CEOs on what they learned building their first senior teams: ———-. As a founder/CEO, building your first management team is something that you often lose sleep over. What makes you feel that you need to level up your management, set up your first management team?

Sales Hiring 261

Sales Hiring Underperforming Technical Team Development Team Review CTO Hire 261

User Pilot

OCTOBER 31, 2024

How to apply actionable metrics to different SaaS business stages. A product analytics strategy is essential for any business looking to make informed decisions about product development and user experience. Enables teams to track progress toward key performance indicators (KPIs). Lack of team resources.

Strategy 105

Strategy Underperforming Technical Team Government Customer Lifetime Value 105

User Pilot

OCTOBER 19, 2024

What does customer satisfaction look like for SaaS businesses? Unlike traditional businesses, most SaaS businesses operate the subscription pricing model. As a result, satisfying customers is key to any success in SaaS. Satisfaction in SaaS, therefore, isn’t simply about developing a nice product and launching it in the market.

Business 111

Business Underperforming Technical Team Customer Lifetime Value Systems Review 111

SaaStr

JUNE 20, 2023

Everyone wants “multiple revenue streams”, even if that means doing none of them as well as they could if they focused. If a VP of Sales has a $500k+ OTE and a big team to manage, does it even make senses to sell courses on the side? I don’t wish to see more people in increasingly bad financial standing this year.

Underperforming Technical Team 322

Underperforming Technical Team Scale Sales Hiring Startup 322

SaaStr

OCTOBER 24, 2022

Developers act, think, and behave differently than your average customer. As an API-first company, WorkOS focuses on selling primarily to developers. Doing Business with Developers. Developers haven’t typically been the buyers in enterprise software, so why should you build for developers?

Outsourced Development 210

Outsourced Development Underperforming Technical Team Development Part-Time VPE 210

SaaStr

JANUARY 29, 2023

Basically all of the SaaS CEOs/founders I know of have made at least one terrible VP+ level hire. Sometimes it’s VP Sales (OK, often, this is the most common mishire — another post here on what a really great VPS can do for you, and how a poor one can wreck your company, coming). Sometimes it’s VP Marketing.

Sales Hiring 335

Sales Hiring Scale Underperforming Technical Team Startup 335

SaaStr

JULY 1, 2021

Dropbox just hit one billion dollars in annual revenue. What’s the secret to SaaS success at YCombinator? Sam : We’re going to talk today about a lot of topics, but the general theme is, what’s the difference between good and great SaaS companies? Getting the team right is so key here. TRANSCRIPT.

VP of Engineering 293

VP of Engineering Sales Hiring Sales Recruiting Underperforming Technical Team 293

SaaStr

APRIL 4, 2025

Companies can meet stringent quality requirements at a fraction of the cost of in-house teams, while accelerating their AI initiatives. Why It Matters : Customer support teams are drowning in tickets, with resolution times getting longer, not shorter. Why It Matters : Business users waste hours navigating complex SaaS UIs.

AI Search 163

AI Search AI Startup Scale 163

Sales Hacker

MAY 9, 2025

In 2023, we saw a surge of SaaS brands adding anything AI-powered or AI-driven into their website headlines. A quick use of Wayback Machine for the top 100 SaaS brands will show you just how pervasive it was. Bad: We use AI to streamline sales workflows. But avoid buzzwords, make it visual and concrete.

AI Search 82

AI Search AI Scale SaaS 82

SaaStr

MARCH 22, 2024

The path to Cheif Revenue Officer (CRO) is different for many people. Tracy Young , CEO and co-founder at TigerEye, sits down with three CROs to talk about how they navigated the journey to revenue leader. Different Pathways to CRO For Jane Kim, former CRO of CircleCl,, she used to work in finance before transitioning to SaaS.

Scale 299

Scale Underperforming Technical Team SMB Finance 299

Sales Hacker

JUNE 17, 2025

Dennis amassed incredible insights through his experience as the Chief Revenue Officer of Procore, where he helped grow the company from $10M to $900M+ in revenue and guided it through a successful IPO. Build the team that builds the company.” – that is part of your go-to-market strategy responsible for growth.

AI 80

AI Technical Advisors Underperforming Technical Team Sales Hiring 80

SaaStr

APRIL 30, 2022

Average Revenue per Customer. So the first question is what made SaaS so successful. If you kind of that question, thinking about the stakeholders and the decisions and companies of using SaaS products, there’s kind of three types. Customers love SaaS products and tools because it simply works. MRR, obviously.

SaaS Payments 246

SaaS Payments Metrics Payment Methods Scale 246

SaaStr

DECEMBER 29, 2022

At Maxio , we help B2B SaaS companies unlock their next stage of growth. Our financial operations platform is designed to meet the unique financial challenges of B2B SaaS, including billing, subscription management, revenue and expense recognition, and SaaS analytics. Instant live customer conversations! With over $1.5B

Scale 271

Scale Underperforming Technical Team B2B AI 271

SaaStr

JUNE 21, 2023

After three months, this talented guy came to Harbaugh with the recognition that LaunchDarkly’s customers were developers. He didn’t like to sell to developers, so he quit. because they needed to rebuild the sales team. They rebuilt the sales team and closed some big deals. And it was true.

Sales Recruiting 293

Sales Recruiting Sales Hiring Underperforming Technical Team Pricing 293

FastSpring

APRIL 26, 2022

Last week, I canceled an annual SaaS subscription (I had three weeks left until renewal). In the language of SaaS, I churned. In part two, we’ll cover five churn-prevention strategies that have been successful in other SaaS businesses. Part I: SaaS Churn Benchmarks. Is There an Ideal Churn Rate for SaaS?

Benchmarks 147

Benchmarks Churn Payments SaaS Payments 147

SaaStr

NOVEMBER 1, 2022

Sequoia Capital’s India arm put together a terrific summary of all their learnings about SaaS and Cloud from SaaStr Annual this year. They also did an A+ session at Annual with several top India SaaS founders, which you can catch below! Here’s 22 of the most relevant takeaways for India’s SaaS ecosystem.

Scale 287

Scale Sales Hiring Underperforming Technical Team Cybersecurity 287

Subscription Flow

OCTOBER 2, 2024

In simple terms, revenue leakage means that a business is unable to collect a 100% of its earned income. There is always a small percentage of income that gets ‘leaked out’, causing revenue loss. Revenue leakage is that amount of money from your customers which gets processed, but which does not end up in your account.

Payments 105

Payments Payment Features Payment Services Payment Solutions 105

SaaStr

APRIL 5, 2021

Hmmmm … well, to me, that’s not a bad place to be once a space, a category, gets to $100m+. But that’s not Disruption — in SaaS at least. Sometimes in SaaS, there are natural monopolies. But more often, SaaS categories with significant complexity in workflows and features end up in natural oligopolies.

Scale 264

Scale Sales Recruiting Underperforming Technical Team Pricing 264

SaaStr

JULY 29, 2019

It got a lot of engagement from the SaaS veterans out there, so I thought it would be worth digging in more on each point: Regrets are different than mistakes. The flip side of recurring revenue is you will later regret things that you could have done earlier to help, that were sort of obvious, that would have helped more of it recur.

Sales Hiring 208

Sales Hiring Venture Capital Scale SaaS 208

User Pilot

DECEMBER 31, 2024

You get something that truly works for you, and we get to connect with people who value what we offer and have the potential to become power users (and sources of sustainable revenue!). In fact, it was first created as an analytics tool, and only in recent years has it also developed an engagement suite. The alternative?

Technical Review 105

Technical Review Underperforming Technical Team Software Review Onboarding 105

SaaStr

JULY 15, 2022

So how feasible do you think that works for a typical B2B SaaS business that probably our user-base is not too knowledgeable about [inaudible] on the internet for something specific in their day-to-day use case? Jason Lemkin: But usually your teams can’t do that. This always works. If you do Salesforce, try to do Pipedrive.

Scale 292

Scale Outsourcing Services Sales Hiring VP of Engineering 292

SaaStr

JANUARY 12, 2023

Management teams must determine how to thrive in a downturn to position their businesses for profitable growth. Companies that operate above 40% revenue growth rate and profit margin stand to generate a sustainable profit, while those operating below 40% may have cash flow or liquidity issues. . “It’s

Consulting 49

Consulting Underperforming Technical Team Management Marketing 49