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. The Critical Question: Is This Additive or Replacement? What This Means for B2B Leaders 1.

AI 257

AI Cloud Software Review Underperforming Technical Team 257

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 263

Technical Review Payment Solutions Scale Payment Services 263

SaaStr

DECEMBER 23, 2021

Q: Dear SaaStr: How Can I Develop Confidence as a Startup CEO? But you need to be confident enough to lead the team and make everyone believe. Care about your team for real. Caring about your team and colleagues alone isn’t enough. Your team needs to look up to you. You need your team to believe in you.

Underperforming Technical Team 293

Underperforming Technical Team Development Startup Leadership 293

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 247

Scale AI Underperforming Technical Team Sales 247

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

SaaStr

JUNE 7, 2025

Companies are discovering that hiring AI talent or upskilling existing teams takes much longer than anticipated. This isn’t necessarily bad news for the AI market, but it does represent a significant shift from the explosive growth patterns of 2023 and early 2024. Integration challenges are mounting.

AI 281

AI Payment Services Payments Scale 281

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. Talk about how youve taken small teams and turned them into revenue machines.

Sales Recruiting 197

Sales Recruiting Interviewing Sales Hiring Scale 197

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. Once you have solidified your company’s vision and have developed a strategic plan on how you will achieve success, don’t get too comfortable. Creating a category.

Scale 246

Scale Underperforming Technical Team Scaling Company Culture 246

SaaStr

NOVEMBER 9, 2020

Do a lot more Business Development and Partnerships. Underperformers found it harder to hide after Covid, and many have already left or moved on. Respectfully move on from any other underperformers by year-end. Those of us who have been around for a while know what happens when office space goes from plentiful to nonexistent.

Underperforming Technical Team 332

Underperforming Technical Team Sales Hiring Travel Cloud 332

SaaStr

MARCH 8, 2025

“Even with a bad hand, if the potential reward is great enough, taking a risk can make mathematical sense.” As second-time founders, Atiyah and his team raised an outsized seed round for Ramp, giving them the capital to tackle a space that most startups couldn’t touch. But this challenge also presents opportunity.

CTO Hire 202

CTO Hire CTO Coach Scale CTO 202

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. Resolution Bot is a product that automatically answers the repetitive questions faced by customer support teams.

Artificial Intelligence 281

Artificial Intelligence Machine Learning Underperforming Technical Team Development 281

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

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.

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

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

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. sales enablement: how strong are the materials sales teams use to pitch? Comms Marketing.

Underperforming Technical Team 340

Underperforming Technical Team Marketing Scale Social Media 340

Intercom, Inc.

JUNE 10, 2020

I hope this post allows people and teams to safely talk about Product Judgment. If you ever had to face a Manager, Director or Exec as they make bad product decisions and you’re struggling to persuade them otherwise, this post will help you. It takes years to build, and therefore ranges from very weak to very strong.

Underperforming Technical Team 291

Underperforming Technical Team Interviewing Communication B2B 291

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

SaaStr

NOVEMBER 8, 2022

How To Build A High-Performing Team And Retain Top Talent. Every leader needs to have a strategic playbook to build high-performing teams and retain top talent,” says Guan Wang, Global Director of Market Intelligence for Snowflake. . Stage 3: Employee Development. The Playbook For Building And Retaining A High-Performing Team .

Underperforming Technical Team 246

Underperforming Technical Team Technical Review Acquisition Company Culture 246

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?

Underperforming Technical Team 210

Underperforming Technical Team Outsourced Development Development Part-Time VPE 210

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

SaaStr

MARCH 20, 2021

Don’t skip too many steps of development. But when I see folks skip 2+ stages of development, I’ve almost never seen that work out. A great boss will find ways to backfill your weaknesses, get you trained one way or another, get you into the right role with the right leads. From 60 days as an SDR straight to a quota-carrying AE.

Sales Hiring 345

Sales Hiring Underperforming Technical Team Branding Pricing 345

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

APRIL 13, 2025

Conrad personally runs payroll for Rippling’s 2,000 employees across a dozen countries as a “part-time job,” while UK companies with even small teams often spend 5-6 days monthly just managing payroll. His rationale: Training capacity : Sales teams can only absorb so much product knowledge. The proof of effectiveness?

Startup 157

Startup Sales Hiring Underperforming Technical Team Cloud 157

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. I think the foundation of high performance teams is that they share five things.

Scale 241

Scale Underperforming Technical Team Scaling Leadership 241

SaaStr

NOVEMBER 26, 2019

sales team. I did all sorts of things there from sales, to project management, to running the engineering team, hiring. This is where I got my chops in growing and scaling enterprise sales teams. We have team selling here that extends beyond the sales team. Want to see more content like this? FULL TRANSCRIPT BELOW.

Scale 288

Scale Sales Hiring Underperforming Technical Team Sales 288

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? Owning an airbnb, doing a podcast, coaching a team, volunteering or trading cards – that’s a hobby and a side-hustle and very much encouraged). Same holds true for developers.”

Underperforming Technical Team 322

Underperforming Technical Team Scale Sales Hiring Startup 322

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? Hiring a large team is necessary, but insufficient. That won’t work.

Startup 312

Startup Scale Underperforming Technical Team Scaling 312

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 170

AI Search AI Startup Scale 170

SaaStr

JANUARY 18, 2023

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. It’s about enabling the people on your team to be more productive and efficient. Lesson 6: Pivoting isn’t a bad thing.

Scale 246

Scale Underperforming Technical Team Scaling Interviewing 246

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

FEBRUARY 16, 2022

As companies begin to succeed, they sometimes develop a tunnel vision towards the customers who have brought them their success. If you don’t work to keep your knowledge of the market fresh and current, you may be left with a narrow view that will inevitably catch your sales and product teams flat-footed. Verify product-user fit.

Underperforming Technical Team 284

Underperforming Technical Team Company Culture Customer Success Product Marketing 284

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 336

Sales Hiring Scale Underperforming Technical Team Startup 336

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

Stax

MARCH 16, 2025

This means having the right technology team in place, setting up ample customer support options, and ensuring that your team is available and trained to address software challenges when they occur. Bad software user experience User experience is everything when it comes to SaaS platforms. This helps alleviate confusion.

Payment Solutions 88

Payment Solutions Software Review Churn SaaS Payments 88

Sales Hacker

AUGUST 7, 2024

He previously built the pre and post sales solutions team at mParticle from zero to supporting hundreds of enterprise customers. Is there a lot of internal or customer work that needs to be done or managed by your team? While mParticle has a killer, commercially focused CS team, inertia affected the team as well early on.

Underperforming Technical Team 119

Underperforming Technical Team Technical Review Sales Hiring Scale 119