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 212

Software Review AI Technical Review Venture Capital 212

SaaStr

JULY 8, 2025

Founders typically possess: Original architectural vision for complex enterprise platforms Deep domain expertise in customer workflows and pain points Technical credibility with both engineering teams and enterprise buyers Product roadmap intuition built from years of direct customer feedback 2.

Scale 180

Scale B2B Underperforming Technical Team Leadership 180

SaaStr

JUNE 7, 2025

The shift from “innovation budget” to “operational budget” means AI tools must compete directly with established software investments—and many aren’t winning those comparisons yet. Companies are discovering that hiring AI talent or upskilling existing teams takes much longer than anticipated.

AI 281

AI Payment Services Payments Scale 281

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 282

Underperforming Technical Team Enterprise Scale Payments 282

Intercom, Inc.

JULY 2, 2020

But obsessing over efficiency can mask what’s most important, and most rewarding, to support teams – actually helping customers. Support teams exist to solve customers’ problems, not to deflect them or find the fastest way to hit the “close” button. In her own words , “When you take care of your customers, the revenue comes.”

Outsourcing Services 253

Outsourcing Services Investment Underperforming Technical Team Outsourced Development 253

Intercom, Inc.

OCTOBER 13, 2020

ML products also require us to manage relatively large technology risks – this is an area where, unlike in most other product development, technical limitations might render the entire design impossible. It’s also easy to over- or under- invest in the technology. Balancing risks in machine learning development.

Artificial Intelligence 281

Artificial Intelligence Machine Learning Underperforming Technical Team Development 281

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 203

Sales Recruiting Marketplace as a Service Underperforming Technical Team Scale 203

SaaStr

MARCH 12, 2025

A smaller number of high-quality leads that convert at higher rates is vastly superior to a flood of poor-fit prospects. You assembled a talented team, built an amazing product, and established a growing SaaS business. Mix in the classic conflict between sales and marketing teams, and you’ve got a recipe for disaster.

Sales Hiring 197

Sales Hiring Marketing Technical Review Underperforming Technical Team 197

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

Incredo

MARCH 20, 2020

The Incredo team switched to a fully remote working system in September 2019. At the beginning it was a bit hard to track the progress of tasks and communicate with team members effectively. Since you started working from home, your whole team already saves around 1 hour of their day.

Underperforming Technical Team 227

Underperforming Technical Team Outsourced Development Systems Review Software Review 227

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

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

SaaStr

NOVEMBER 26, 2019

sales team. As everyone left to work for an investment bank in California or New York that summer of ’99, I went to work at a startup in Ann Arbor. I did all sorts of things there from sales, to project management, to running the engineering team, hiring. We have team selling here that extends beyond the sales team.

Scale 288

Scale Sales Hiring Underperforming Technical Team Sales 288

FastSpring

JANUARY 23, 2025

How selling an investment business is very different from getting VC funding. They’re interested in the return on investment, they’re interested in the growth opportunities, they’re interested in the strategies and the synergies that those businesses can bring them, either as individuals or as companies.

Scale 119

Scale Entrepreneurship Scaling Underperforming Technical Team 119

SaaStr

MARCH 5, 2025

David Frankel is Managing Partner at Founder Collective, a successful seed fund with investments in companies like The Trade Desk, Olo, and Coupang. Manage Team Expectations – Balance transparency with the need to keep the team focused on building the business.

Technical Review 201

Technical Review Software Review Development Team Review Sales Hiring 201

SaaStr

MARCH 30, 2024

It’s one thing to invest in an area where only 5% of your business is today. 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. And stymie all of them.

Scaling 301

Scaling Revenue Underperforming Technical Team Market Segmentation 301

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

Casey Accidental

MARCH 29, 2022

A common issue leaders in product management, design, or engineering face is justifying investment in the “non-sexy” stuff. Non-sexy things include general user experience improvements, performance, developer velocity, infrastructure, technical debt, and, fortunately less than it used to be, growth. User Experience.

Investment 139

Investment Underperforming Technical Team User Experience Scale 139

SaaStr

MAY 10, 2022

Recovery from COVID has taught us that adapting and learning how to thrive in new ways in the face of change, whether good or bad, can lead to exponential growth. . Develop a well-defined vision. If you have a comprehensive, compelling vision, it will be easy for your teams to trust it and rally behind you. Define your crisis.

Travel 270

Travel Revenue Underperforming Technical Team Scale 270

SaaStr

NOVEMBER 25, 2023

If someone is working hard but isn’t working out, invest in them and see if you can get them into the high-performing category. The underperformers who aren’t putting in the effort get a conversation, and if things don’t change, it’s not a good fit. Others are doing little work and not working out. Guess what? Jameson called that guy.

Sales Hiring 281

Sales Hiring Underperforming Technical Team Revenue Sales 281

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. A bad one can torpedo you.

Sales Recruiting 293

Sales Recruiting Sales Hiring Underperforming Technical Team Pricing 293

SaaStr

JUNE 4, 2021

Pomel focused his session on: Making your SaaS startup customer-centric: Hw event marketing has helped him integrate his engineering and sales teams. How many of you guys’ product rely on the highly functioning engineering team? Helping the engineering teams run smoothly and being super productive thanks to mentoring.

Scale 317

Scale Underperforming Technical Team Sales Hiring Engineering 317

SaaStr

JUNE 21, 2024

These nine sales concepts, when done correctly, will greatly improve your sales and sales teams. #1: Most people think you need to hire more salespeople in a demand-poor environment. Demand-poor environments lead to problems like: Sales reps clinging on to opportunities for too long. That’s the wrong answer.

Sales Recruiting 290

Sales Recruiting Sales Hiring Scale Outsourced Development 290

SaaStr

JULY 1, 2021

The second is pulling more around values, and how we approached team building. Even as a three person team, we went through an exercise to figure out what do we stand for, as a team? Sam : This is not my insight, but someone else says… I really do believe it, that the team you build is the company you build.

VP of Engineering 293

VP of Engineering Sales Hiring Sales Recruiting Underperforming Technical Team 293

SaaStr

JANUARY 12, 2023

Management teams must determine how to thrive in a downturn to position their businesses for profitable growth. However, management teams that pursued growth at all costs were punished severely. As a result, it’s crucial to evaluate the right blend of long-term investments and target the core methodically. Key takeaways.

Consulting 49

Consulting Underperforming Technical Team Management Marketing 49

SaaStr

DECEMBER 31, 2020

What you really want if your deal size isn’t tiny are at least somewhat qualified leads for your team to follow-up with. What you really want if your deal size isn’t tiny are at least somewhat qualified leads for your team to follow-up with. After all, no one on that list opted in to hear about your product.

Underperforming Technical Team 236

Underperforming Technical Team Content Marketing Innovation Investment 236

SaaStr

MARCH 22, 2024

The highs and lows always come, usually involving the people on your team. For Erica, the bad days are when they’re not executing or achieving growth the way they want. But you don’t carry any numbers, so your success is predicated on your team’s success. Each of these CROs describes what their worst day is.

Scale 300

Scale Underperforming Technical Team SMB Finance 300

SaaStr

AUGUST 1, 2022

The developed world revolves around e-commerce. Push yourself and your team to keep an open mind when you’re considering whom you can serve and how you can serve them. Embed innovation into your team’s DNA. Innovation should happen across the entire company, not just in the product team. Global approach. it can’t be done.

Underperforming Technical Team 261

Underperforming Technical Team Marketing Innovation Investment 261

SaaStr

OCTOBER 30, 2021

A mentor of mine suggested that I reframe my search to seek out companies that I would invest in, instead of the other way around. He told me, you can invest time, talent, or treasure. Unfortunately for me, I had little experience, not much talent, and lacked the treasure/money to invest. It seemed like the best investment! .

Scale 284

Scale Sales Hiring Sales Underperforming Technical Team 284

Sales Hacker

JUNE 17, 2025

But behind every product launch and revenue milestone is a team – and building that team is one of the hardest and important parts of the journey. Build the team that builds the company.” – that is part of your go-to-market strategy responsible for growth. I think that that like is probably the thing I see the least of.

AI 82

AI Technical Advisors Underperforming Technical Team Sales Hiring 82

SaaStr

JULY 8, 2020

What Nobody Tells You About Seed Investing with SaaStr CEO Jason Lemkin and Cowboy Ventures Founder and Partner Aileen Lee. I think it gives us a perspective that maybe we don’t get in some other places, in addition to many great investments over the years. Personally, our team has been holding back a little bit.

Investment 202

Investment Technical Review Part-Time VPE Development Team Review 202

SaaStr

JANUARY 2, 2024

You don’t want conflict with the sales team. How do you leverage that offer to develop relationships with partners? This is where they started, but startups weren’t adopting the product as much with a discount, and there was a lot of conflict with the sales team. During SaaStr Annual, Zendesk Sr. Do they have a CRO in place?

Startup 262

Startup Scale Underperforming Technical Team AWS 262

Sales Enablement, SaaS and Growth

MARCH 23, 2020

Companies which don’t use mental models risk unleashing mayhem with poor choices or becoming bloated and bureaucratic by reducing the volume and speed at which decisions are made - both scenarios are undesirable and will impact growth. OKRs are a useful mental model - they make it crystal clear what people and teams should be striving for.

Underperforming Technical Team 215

Underperforming Technical Team Scale Sales Hiring Marketplace as a Service 215

Intercom, Inc.

APRIL 22, 2021

If you’re a senior engineer and want to further your career, what skills should you develop? Moving forward in your career, avoid the trap of doing work that feels high-impact, but it’s actually not , or work that makes you look good at the expense of the project and the team. How do people move into staff engineering roles?

Technical Review 274

Technical Review Leadership VP of Engineering CTO Coach 274

Stax

MAY 5, 2025

In recent years, businesses have seen this massive shift from desktop to mobile devices which has forced them to develop apps with built-in integrated payment gateways. A bad payment experience can lose customers and damage your brand. There are many different gateways available, each with its strengths and weaknesses.

Payments 88

Payments Payment Services Merchant Services Payment Solutions 88

Intercom, Inc.

JUNE 8, 2021

According to one Microsoft Global State of Customer Service report , 90% of consumers surveyed said that customer service is an important factor in their choice of, and loyalty to, a brand, while nearly two-thirds (58%) would sever their relationship with a business due to poor customer service. Conversational support is the new normal.

Technical Review 222

Technical Review Underperforming Technical Team Customer Support Marketplace as a Service 222

SaaStr

NOVEMBER 1, 2022

They are hiring leaders, building teams, and attracting advisors in the US while devouring the SV SaaS playbook. AI is likely the next platform, dev tools are strategic given the scarcity of developers, cybersecurity is front and center for enterprises, and the data stack is still going strong. Proximity to customers helps too.

Scale 293

Scale Sales Hiring Underperforming Technical Team Cybersecurity 293