SaaStr

JUNE 23, 2025

✨ Lemkin (@jasonlk) June 23, 2025 The $10M-$100M ARR Sprint: How Replit Became the Fastest-Growing “Vibe Coding” App (Or One Of The Fastest) A deep-dive into the AI development platform wars and why Replit’s 10x growth in 5.5 And allowing more experienced developer to ship far, far faster. 2023 : $2.4M

Software Review 208

Software Review AI Technical Review Venture Capital 208

SaaStr

JANUARY 26, 2025

The KPI Alignment System Have customers email explicit performance expectations Build custom reporting dashboards Weekly cross-team optimization meetings Formal performance reviews 2. The Education Ecosystem Attentive University Platform certification program “Texts We Love” showcase Industry-standard guides (e.g.,

Technical Review 258

Technical Review Payment Solutions Scale Payment Services 258

SaaStr

JUNE 14, 2025

When a development team switches to an AI-powered coding assistant, they’re not just adding a new tool—they’re often reducing their dependency on multiple legacy SaaS platforms. Weak players get acquired or shut down. Mature markets favor scale, and this disruption creates acquisition opportunities.

AI 252

AI Cloud Software Review Underperforming Technical Team 252

SaaStr

JUNE 7, 2025

Companies are discovering that hiring AI talent or upskilling existing teams takes much longer than anticipated. Many organizations are stuck in “pilot purgatory”—running successful experiments but unable to scale them. Integration challenges are mounting.

AI 274

AI Payment Services Payments Scale 274

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 244

Scale AI Underperforming Technical Team Sales 244

Intercom, Inc.

OCTOBER 13, 2020

Those companies need to spend a lot of time considering problems that will occur when a system has millions of users, and have to think carefully about ML tech debt given their scale. Similarly, don’t design far beyond what the machine learning can deliver – instead, traverse the product development tree, one level of depth at a time.

Artificial Intelligence 281

Artificial Intelligence Machine Learning Underperforming Technical Team Development 281

SaaStr

AUGUST 31, 2022

Scalability is about capability, so businesses need to understand whether they have the capacity to grow and whether their infrastructure and team can accommodate growth. The stage of scaling from $10 million to $100 million ARR may seem like a daunting task, but it is an exciting one. Turning a vision into reality.

Scale 246

Scale Underperforming Technical Team Scaling Company Culture 246

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 294

Scaling Revenue Underperforming Technical Team Market Segmentation 294

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 207

Outsourced Development Underperforming Technical Team Development Part-Time VPE 207

FastSpring

JANUARY 23, 2025

When I was running it, it was a lot smaller than that, but scaled that up very, very quickly. And that’s substantial scale in. Blake Hutchison (20:38) And of course, these businesses don’t have the scale or opportunity that a VC asset would typically have for growth. That’s now a billion dollar company.

Scale 116

Scale Entrepreneurship Scaling Underperforming Technical Team 116

Intercom, Inc.

JANUARY 12, 2021

This post is an adaptation of a talk I recently gave at the Amazon Web Services (AWS) community day event in Dublin about the technical strategies I’ve experienced that don’t work and the ones that have helped us to grow and scale at Intercom. But over time, we noticed that teams hated working on these services.

Technical Review 269

Technical Review Scale multi-cloud Kubernetes Scaling 269

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.

Sales Recruiting 198

Sales Recruiting Marketplace as a Service Underperforming Technical Team Scale 198

SaaStr

FEBRUARY 4, 2020

Lexi Reese, Gusto COO uses her 20+ years of experience to provide advice on building high performing teams using authenticity, empathy and logic. Lexi explains the importance of team trust, driver and passenger mindsets, and much more. So a playbook on scaling high performance organizations in 30 bit minutes. So big, big scale.

Scale 237

Scale Underperforming Technical Team Scaling Leadership 237

SaaStr

JANUARY 18, 2023

Unicorn companies often need to scale quickly to meet the demands of their rapidly growing customer base. Lesson 1: Everything is about your team. Every startup needs strong team dynamics to pull through tough times. It’s all about the team 99% of the time and 1% product and process. ” – David Cancel.

Scale 246

Scale Underperforming Technical Team Scaling Interviewing 246

SaaStr

MAY 22, 2025

Be prepared to talk about the team youve builtwho you hired, why you hired them, and how they performed. Be ready to share specific examples of how youve developed and executed sales strategies that drove revenue growth. Bring Energy and Vision : Show that youre not just here to manage a teamyoure here to scale the business.

Sales Recruiting 192

Sales Recruiting Interviewing Sales Hiring Scale 192

Tom Tunguz

MARCH 3, 2020

Each bucket has a set of disciplines that the team scores. First, it enumerates the important priorities for a marketing team. And second, the scorecard provides a way for a team to understand their strengths and weaknesses. You might score each on a 1 to 10 scale. Business Development. who does it sell to?

Underperforming Technical Team 340

Underperforming Technical Team Marketing Scale Social Media 340

SaaStr

SEPTEMBER 24, 2020

You know how everyone says you'll never look and wish you'd kept a bad VP as long as you did? Because to scale, you are going to need to add a true management team, and then a second one, and then layers of management. The fewer weak hires they continue to make. The less they slow down feature development.

Sales Hiring 269

Sales Hiring Part-Time VPE Scale Underperforming Technical Team 269

Intercom, Inc.

SEPTEMBER 10, 2020

It’s an approach that’s served him well along the road to building the HubSpot sales team, where he was CRO for nine years. Applying data and science to scaling has become easier because of the shift that’s happened in the software industry over the past 15 years, from outside sales to inside sales. A data-driven framework for scaling.

Scale 226

Scale Scaling Sales Recruiting Sales Hiring 226

SaaStr

JUNE 19, 2024

Bitly CEO Toby Gabriner and CPO Kelsey Stevenson share the three secret ingredients that helped them when scaling to $100M ARR and what they could have done differently. You might have to rebuild your marketing team. Bitly had an Enterprise sales-focused team. While that might seem like a bad thing, it wasn’t.

Scale 294

Scale Scaling Underperforming Technical Team User Experience 294

Tom Tunguz

FEBRUARY 24, 2020

There’s a CEO at the top in red, VPs in orange, senior contributors in dark gray, team leads in green, and junior individual contributors in light gray. Sometimes there are directors running teams that should be headed by VPs. Is this so bad? To scale means hiring lots of people.

Startup 312

Startup Scale Underperforming Technical Team Scaling 312

SaaStr

JULY 15, 2022

Jason recently opened up an AMA on Twitter Spaces to answer questions about scaling from $1M to $10M. We did a good AMA on this scaling at SaaStr Europa in Barcelona, a couple weeks back. That will scale, and then take those emails after four great pieces of content and do a weekly webinar and do a weekly get-together for them.

Scale 286

Scale Outsourcing Services Sales Hiring VP of Engineering 286

ChurnZero

OCTOBER 25, 2024

There are so many questions to answer when considering how to scale a customer success team. What about team leads? When do I split my one team into two teams? How do I split one team into two? And I know you want to scale your customer success team in the right way. Well…maybe. Probably not.

Scale 52

Scale Underperforming Technical Team Customer Success Scaling 52

BetterCloud

MAY 13, 2025

Every IT team is grappling with the same reality: the ever-widening chasm between the demands placed on IT and the resources at their disposal. Automated systems, on the other hand, can provide continuous vigilance, ensuring consistent application of security updates and proactive identification of potential weaknesses.

Headcount 52

Headcount Scale Underperforming Technical Team Scaling 52

SaaStr

JANUARY 24, 2024

How should you handle presenting challenges to your C-suite team when you’ve just joined the company? She was hired because they saw a bit of softening in new business growth, and she came to help diagnose what was going on and help scale the business. The bad news is it wasn’t driving the results they wanted.

Scale 268

Scale Sales Hiring Scaling Revenue 268

Intercom, Inc.

OCTOBER 12, 2021

As a support leader, you already know how important it is to take care of your customers – but it’s just as important to take care of your support team. Here’s why human support is so crucial for any customer-centric organization, and how it can have a significant impact on your team, your business, and your customers. Here’s why.

Underperforming Technical Team 222

Underperforming Technical Team Technical Review Payment Methods Payments 222

Intercom, Inc.

JULY 28, 2022

And for Intercom’s VP of Sales EMEA, Sanj Bhayro , scaling is just what you need to invest in to ensure growth becomes as constant and linear as it can be. Sanj has plenty of experience scaling sales teams at growing businesses, and that’s precisely why, as of November of last year, he‘s overseeing EMEA sales at Intercom.

Scale 210

Scale Scaling Sales Hiring Sales Recruiting 210

User Pilot

OCTOBER 31, 2024

A product analytics strategy is essential for any business looking to make informed decisions about product development and user experience. Plus, there are many reasons why you need a product analytics strategy: Aligns product development with user needs and business goals. Lack of team resources. Outdated technology.

Strategy 105

Strategy Underperforming Technical Team Government Customer Lifetime Value 105

Intercom, Inc.

JUNE 1, 2021

Most support teams have seen an influx of support queries since COVID-19 hit – and those issues are more complex than ever. According to recent research, however, many teams aren’t sufficiently equipped to meet these new challenges. Challenge #1: Limited team bandwidth, resources, and budget.

Underperforming Technical Team 232

Underperforming Technical Team Technical Review Scale Headcount 232

SaaStr

NOVEMBER 14, 2019

If your SaaS business has a sales team, there’s no way to grow 100% year-over-year without also growing your sales leadership. Knowing the common pitfalls won’t stop you or your team from making them, but it will help build the most important skill any manager can have: resiliency. SaaS = Software that scales. Overwhelmed.

Scale 179

Scale Sales Hiring Scaling Underperforming Technical Team 179

SaaStr

JANUARY 29, 2023

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). The #1 reason to do a start-up is Career Development. It’s one of our enduring topics on SaaStr. Sometimes it’s VP Marketing.

Sales Hiring 333

Sales Hiring Scale Underperforming Technical Team Startup 333

SaaStr

JULY 22, 2019

Hear from Roger Scott, New Relic’s EVP and Chief Customer Officer as he shares his 7 tips and tricks for keeping your customers happy— and how to do so at a large scale. That’s not a bad start. We work with mostly modern teams. Want to see more content like this? Join us at SaaStr Europa 2020. FULL TRANSCRIPT BELOW.

Scale 230

Scale Scaling Sales Hiring Underperforming Technical Team 230

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 258

Sales Hiring Underperforming Technical Team Development Team Review CTO Hire 258

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. The team comes from MongoDB and Elastic, bringing deep search expertise.

AI Search 167

AI Search AI Startup Scale 167

SaaStr

JULY 29, 2022

Jason recently opened up an AMA on Twitter Spaces to answer questions about how to scale faster. And I’ve watched them fairly quickly scale, to soon they’ll be at 10 million in revenue. As they scaled, they radically changed how they did sales. Jason Lemkin: Okay. Let’s get it going. Times are good.

Scale 268

Scale Scaling Sales Hiring Enterprise 268

SaaStr

OCTOBER 10, 2022

From the get-go, ensure alignment between sales and marketing teams on goals and anticipated outcomes. Scale winning behaviors. The opportunity to scale growth is understanding the behaviors of the top of your sales force.”. Scale winning behavior across the sales force. Create dynamic alignment on goals. Key takeaways.

Scale 320

Scale Sales Hiring Venture Capital Marketing 320

SaaStr

NOVEMBER 9, 2022

Developing a product that solves a customer’s pain point provides a sense of pride and can drive the positive, emotional moment of awe that retains customers for the long haul. That doesn’t make them bad people. Most valuable employees will want to grow and develop new skills. Business model. The same goes for your investors.

Underperforming Technical Team 49

Underperforming Technical Team Business Scale Business Model 49

SaaStr

JUNE 20, 2023

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? Once you had something, once you had scale, then go help one other startup. I don’t wish to see more people in increasingly bad financial standing this year. Same holds true for developers.”

Underperforming Technical Team 316

Underperforming Technical Team Scale Sales Hiring Startup 316