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 213

CTO Hire CTO Coach Scale CTO 213

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 333

Underperforming Technical Team Sales Hiring Travel Cloud 333

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

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 159

Startup Sales Hiring Underperforming Technical Team Cloud 159

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 212

Outsourced Development Underperforming Technical Team Development Part-Time VPE 212

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

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 205

Sales Hiring Marketing Technical Review Underperforming Technical Team 205

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 263

Sales Hiring Underperforming Technical Team Development Team Review CTO Hire 263

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

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 177

AI Search AI Startup Scale 177

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

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, hey Jesse, I like the look of your blog, can I buy it? Blake Hutchison (06:32) Yes.

Scale 120

Scale Entrepreneurship Scaling Underperforming Technical Team 120

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 252

Scale Underperforming Technical Team Scaling Leadership 252

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. A bit more here: Corporate Blogs Always Work.

Underperforming Technical Team 245

Underperforming Technical Team Content Marketing Innovation Investment 245

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 295

Scale Sales Hiring Underperforming Technical Team Sales 295

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 324

Underperforming Technical Team Scale Sales Hiring Startup 324

SaaStr

JANUARY 27, 2024

So with that, let’s dive into what’s new at WordPress: Is Blogging on the Decline? Matt shares that blogging did decline for a while, and it does seem to be all over social how folks are quitting blogging or vlogging these days. What people love about a blog is a person’s voice and their story.

Underperforming Technical Team 332

Underperforming Technical Team Social Media Government Subscription 332

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

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 287

Underperforming Technical Team Company Culture Customer Success Product Marketing 287

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 337

Sales Hiring Scale Underperforming Technical Team Startup 337

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. I know it’s a lot of pressure.

Scale 52

Scale Underperforming Technical Team Customer Success Scaling 52

SaaStr

JULY 15, 2022

You could watch it on YouTube or search on SaaStr on the blog about how ClickUp leveraged it. Jason Lemkin: You certainly can hire a whole content team and build 10,000 pieces of content, but I will tell you what I have always seen work is one incredible piece a week. Jason Lemkin: But usually your teams can’t do that.

Scale 296

Scale Outsourcing Services Sales Hiring VP of Engineering 296

SaaStr

NOVEMBER 25, 2023

The underperformers who aren’t putting in the effort get a conversation, and if things don’t change, it’s not a good fit. Jameson and Sam also recommend that across the org: sales, marketing and CS — the early and sooner you can get the entire team re-focused on creating their own pipeline, the better. Guess what?

Sales Hiring 284

Sales Hiring Underperforming Technical Team Revenue Sales 284

Intercom, Inc.

JANUARY 12, 2021

While that doesn’t sound very bad, according to Corey Quinn, the world’s most notorious Cloud Economist, it goes against best practices or “sensible defaults” and is “ the worst practice to be avoided by default.” .” But over time, we noticed that teams hated working on these services.

Technical Review 269

Technical Review Scale multi-cloud Kubernetes Scaling 269

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 296

Sales Recruiting Sales Hiring Underperforming Technical Team Pricing 296

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 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 293

Sales Recruiting Sales Hiring Scale Outsourced Development 293

SaaStr

MARCH 30, 2024

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. It’s one thing to invest in an area where only 5% of your business is today. The “I Give Up” VP Hire.

Scaling 304

Scaling Revenue Underperforming Technical Team Market Segmentation 304

SaaStr

NOVEMBER 7, 2023

The good news is you have a big backlog, and the bad news is you have a big backlog. Adam came up with the wildest idea he could think of for an app and used Anthropc, a large language model company, to help develop the idea. All these developers will have agents to help them write faster and faster. What’s the data model?

Generative AI 296

Generative AI AWS Artificial Intelligence AI 296

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 296

VP of Engineering Sales Hiring Sales Recruiting Underperforming Technical Team 296

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 319

Scale Underperforming Technical Team Sales Hiring Engineering 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 last thing you want the team doing is chasing a shiny penny, when what really matters is hitting the plan for the quarter.

Underperforming Technical Team 356

Underperforming Technical Team Cloud Revenue Acquisition 356

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 315

Underperforming Technical Team Leadership Outsourced Development Finance 315

SaaStr

JANUARY 16, 2023

That doesn’t mean they are “bad” Many, in fact, will thrive as a VP or Director somewhere else. Someone selling Gong today often will really struggle selling a complex developer product or nuanced pharma SaaS. It’s just they won’t make it at your particular, early-stage, quirky, pre-brand startup.

Sales Hiring 328

Sales Hiring Startup Underperforming Technical Team Branding 328

SaaStr

DECEMBER 18, 2019

Growth exposes your weaknesses, and it will cause more problems than it solves – until you make sales scalable. Develop a culture of initiative, not adequacy, by embracing employee ownership. From Impossible to Inevitable helps you take impossible goals and turn them into inevitable successes for your business and team.

Underperforming Technical Team 256

Underperforming Technical Team Revenue Development Software 256

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 303

Scale Underperforming Technical Team SMB Finance 303

Intercom, Inc.

AUGUST 11, 2020

Intercom has responded by hiring a diversity and inclusion consultant, updating our recruitment strategy and hiring practices to reduce bias, scheduling allyship training for all employees, and amplifying Black voices in our podcast and blog. They equate “white” with “good” and “black” with “bad.”. This was going to be a team effort.

Technical Review 289

Technical Review Software Review Systems Review CTO Hire 289