SaaStr

JUNE 20, 2025

The Infrastructure Bypass Midmarket software companies are caught in a “pressure cooker” with fast-moving AI startups developing applications far more rapidly than traditional software companies on one side, and tech giants investing billions in proprietary AI tools on the other.

AI Search 233

AI Search Artificial Intelligence AI CTO Hire 233

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 222

Scale AI Underperforming Technical Team Sales 222

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 278

Underperforming Technical Team Enterprise Scale Payments 278

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 297

Scaling Revenue Underperforming Technical Team Market Segmentation 297

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 269

Sales Hiring Underperforming Technical Team Revenue Sales 269

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. Not only is Klaviyo a rocketship but also the first to IPO in over 2 years (since December 2021) when it went public in September of 2023.

Revenue 304

Revenue Scale Underperforming Technical Team Sales Hiring 304

SaaStr

AUGUST 31, 2022

The $100 million in Annual Recurring Revenue (ARR) mark is a magnificent milestone for companies that indicates sustainable business growth. 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. Creating a category.

Scale 246

Scale Underperforming Technical Team Scaling Company Culture 246

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. . He highlights the three key strategies that helped TripActions scale and boost their revenue. Develop a well-defined vision. Do not waste time developing a Plan B.

Travel 265

Travel Revenue Underperforming Technical Team Scale 265

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 186

Sales Recruiting Interviewing Sales Hiring Scale 186

SaaStr

MARCH 12, 2025

With 10+ years as a CMO at companies ranging from $1M to $1B in revenue, another 10+ years as CEO of companies in the $0-$100M range, and extensive experience as an independent director on startup boards, Dave offers a 360-degree perspective on marketing’s role in SaaS success. . But there’s a better way.

Sales Hiring 186

Sales Hiring Marketing Technical Review Underperforming Technical Team 186

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 193

Sales Recruiting Marketplace as a Service Underperforming Technical Team Scale 193

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

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 262

Sales Hiring Part-Time VPE Scale Underperforming Technical Team 262

SaaStr

JANUARY 24, 2024

How should you handle presenting challenges to your C-suite team when you’ve just joined the company? Solving High Volume, Low Conversion at Lattice Dini Mehta joined Lattice at $3M in revenue when it had just 10 people in seat for Go-To-Market and 7 salespeople. The bad news is it wasn’t driving the results they wanted.

Scale 271

Scale Sales Hiring Scaling Revenue 271

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 260

Sales Hiring Underperforming Technical Team Development Team Review CTO Hire 260

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. Sales Organization Structure Conrad reveals his preference for dedicated sales teams for each product, despite internal disagreement.

Startup 154

Startup Sales Hiring Underperforming Technical Team Cloud 154

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 208

Outsourced Development Underperforming Technical Team Development Part-Time VPE 208

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 319

Underperforming Technical Team Scale Sales Hiring Startup 319

SaaStr

NOVEMBER 25, 2020

Do you have two sales teams? Who gets what part of the long-term development budget? And most importantly, multiple products can be very distracting at the management team level. The new product tends to dominate the discussions, yet by definition, is only a tiny percent of the revenues in the early days.

Underperforming Technical Team 356

Underperforming Technical Team Cloud Revenue Acquisition 356

Stax

MARCH 16, 2025

As a SaaS business leader, reducing software user churn is an important part of maintaining your customer base and increasing revenue. Key metrics include customer churn rate, revenue churn, and net revenue retention (NRR). Lower churn leads to higher customer lifetime value (LTV), better brand reputation, and increased revenue.

Payment Solutions 88

Payment Solutions Software Review Churn SaaS Payments 88

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 334

Sales Hiring Scale Underperforming Technical Team Startup 334

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

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 160

AI Search AI Startup Scale 160

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 289

Sales Recruiting Sales Hiring Underperforming Technical Team Pricing 289

User Pilot

OCTOBER 19, 2024

Satisfaction in SaaS, therefore, isn’t simply about developing a nice product and launching it in the market. For instance, you can launch a CSAT survey after a customer interacts with your support team. Similarly, unhappy customers are more likely to tell others of their poor experience. Userpilot review on G2.

Business 111

Business Underperforming Technical Team Customer Lifetime Value Systems Review 111

SaaStr

NOVEMBER 23, 2022

The success of an executive team often depends as much on their interpersonal harmony as their professional expertise. How does a team establish rapport with one another? Algolia’s Bernadette Nixon (Chief Executive Officer) and Michelle Adams (Chief Revenue Officer) have spent the past few years developing this relational toolbox.

Underperforming Technical Team 310

Underperforming Technical Team Leadership Outsourced Development Finance 310

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

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

FEBRUARY 16, 2022

Product-led companies face a long road as they attempt to manifest themselves from having abstract vision to millions in revenue. As companies begin to succeed, they sometimes develop a tunnel vision towards the customers who have brought them their success. Jeff Bezos says that customers are always unhappy; they always want more.

Underperforming Technical Team 281

Underperforming Technical Team Company Culture Customer Success Product Marketing 281

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. Shifting from an operator and loving operations and data to a sales and revenue leadership role felt like a big jump.

Scale 296

Scale Underperforming Technical Team SMB Finance 296

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. We had 5,000 employees and $14 billion in revenue. Our customers, our employees, our revenue.

Scale 216

Scale Underperforming Technical Team Scaling Leadership 216

FastSpring

JANUARY 23, 2025

Podcast Full Interview: Video Transcript Jesse Paliotto (00:04) Hello, everyone, and welcome to Growth Stage podcast, where we discuss how digital product companies grow revenue, build meaningful products and increase the value of their business. And then of course you generate revenue in much the same way as a blog.

Scale 118

Scale Entrepreneurship Scaling Underperforming Technical Team 118

SaaStr

DECEMBER 18, 2019

If you needed to triple revenue within the next three years, would you know exactly how to do it? Whether you have a $1 billion or a $100,000 business, you can use the same insights as these notable companies to learn what it really takes to break your own revenue records. Read more to find out how! How do you sustain growth?

Underperforming Technical Team 248

Underperforming Technical Team Revenue Development Software 248

Blulogix

DECEMBER 3, 2024

By BluLogix Team Planning for Growth: Using Revenue Insights Planning for Growth: Using Revenue Insights For businesses seeking to expand or enter new markets, strategic planning is critical to achieving successful outcomes.

Revenue 52

Revenue Underperforming Technical Team Payment Features Leadership 52

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

APRIL 1, 2021

Not necessarily in revenue, and often not in their core market. Some examples: Okta basically won the corporate side of identity (rocketed to #1) but wasn’t #1 on the developer side. Smaller deals can sometimes just be about experiments, and teams. Buy a pre-revenue startup in space with a strong team.

Underperforming Technical Team 263

Underperforming Technical Team Cloud Acquisition Communication 263

Intercom, Inc.

DECEMBER 4, 2019

That commitment and focus on how to foster real human connections is evident in every single thing we do on a daily basis, and the resulting success is clear to see, with a valuation of more than $1 billion and revenue to justify it. 1 Poor definition of value proposition and feature focus. 2 First-mover disadvantage. . #2

Branding 209

Branding Underperforming Technical Team Technical Review Airlines 209