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 179

Scale B2B Underperforming Technical Team Leadership 179

SaaStr

MAY 22, 2025

Dear SaaStr: How Can I Crush a VP of Sales Interview? To nail a VP Sales interview, you need to demonstrate that youre not just a smooth talker with a great LinkedIn profileyou need to show youre the real deal. Too many VPs of Sales and CROs show up to interviews knowing almost nothing about the product.

Sales Recruiting 195

Sales Recruiting Interviewing Sales Hiring Scale 195

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. Product-led outperformers generate ten percentage points higher in ARR and 50% higher in valuations than sales-led growth outperformers.

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. Why the Slowdown Might Be Illusory Enterprise Sales Cycles Are Finally Kicking In The most compelling explanation for the apparent plateau has nothing to do with demand and everything to do with procurement realities.

AI 281

AI Payment Services Payments Scale 281

SaaStr

NOVEMBER 26, 2019

Hear from Duo Security’s VP of Inside Sales America on how to build a $2.3B sales team. Jennifer Lawrence | VP, Inside Sales @ Duo Security. Today I’m going to start by telling you a little bit about me, a little bit about Duo, and then the secrets to building a killer inside sales org. Good afternoon.

Scale 285

Scale Sales Hiring Underperforming Technical Team Sales 285

SaaStr

MARCH 12, 2025

The 4 Things Most Founders Get Wrong About Marketing: “We’re a product company, not a marketing company” – The hard truth is that 9 out of 10 B2B companies spend more on sales and marketing than R&D. You assembled a talented team, built an amazing product, and established a growing SaaS business.

Sales Hiring 195

Sales Hiring Marketing Technical Review Underperforming Technical Team 195

SaaStr

JULY 12, 2025

” This approach gave them insights no amount of customer development interviews could provide. “We hear it all the time—people saying, ‘Oh, I first heard about Vanta on a podcast,'” their marketing team reports. “We handed this over to Segment and then asked them three questions: What did I give you?

Sales Hiring 179

Sales Hiring Software Review compliance Sales Recruiting 179

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. Some sales professionals have thrived in this environment. Instead of a crummy office at 2x the price.

Underperforming Technical Team 332

Underperforming Technical Team Sales Hiring Travel Cloud 332

SaaStr

JULY 10, 2025

Don’t Expect It to Replace Everything This is additive to your existing sales and marketing efforts, not a replacement. We developed what we call “The Four C’s” for pre-call research: Chat : What did they discuss with our AI? Create Dynamic, Customized Follow-up Materials Stop sending generic sales decks.

AI 188

AI Scale Sales Hiring Underperforming Technical Team 188

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 202

Sales Recruiting Marketplace as a Service Underperforming Technical Team Scale 202

SaaStr

OCTOBER 10, 2022

From a venture capital perspective, there’s now a premium on driving efficient growth rather than growth at any cost. . “Sales and marketing alignment is a terrific place to figure out and improve efficient growth.” . From the get-go, ensure alignment between sales and marketing teams on goals and anticipated outcomes.

Scale 325

Scale Sales Hiring Venture Capital Marketing 325

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? Some classics here: How My VP, Sales Doubled Our Sales in 90 Days. If Your VP Sales Isn’t Going to Work Out — You’ll Know in 30 Days. Your VP of Sales Shouldn’t Be Perfect. They hire weak, too junior folks.

Sales Hiring 269

Sales Hiring Part-Time VPE Scale Underperforming Technical Team 269

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?

Underperforming Technical Team 340

Underperforming Technical Team Marketing Scale Social Media 340

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.

Startup 157

Startup Sales Hiring Underperforming Technical Team Cloud 157

SaaStr

MARCH 20, 2021

I’ve seen sales reps great at $20k deals join a start-up with tons of leads but at a $2k price point and fail. Pick a sales process you are comfortable with. Can you do truly competitive sales? Not everyone is ready for highly technical or highly verticalized sales in the early days of a start-up’s life. This is #1.

Sales Hiring 345

Sales Hiring Underperforming Technical Team Branding Pricing 345

SaaStr

JUNE 21, 2024

Sam Blond, the former CRO at Brex with 15 years in tech sales, took the stage at SaaStr Europa 2024 to share nine easy sales concepts that so many get wrong. Sam got his first job in tech sales as an SDR for Jason Lemkin’s company, EchoSign, which later sold to Adobe and launched his career. They did this right at Brex.

Sales Recruiting 290

Sales Recruiting Sales Hiring Scale Outsourced Development 290

SaaStr

JANUARY 21, 2020

Justin Welsh, former SVP of Sales at PatientPop explains how he started in SaaS in 2009 as the second sales hire at Zocdoc. Justin used Sales Culture to grow a successful PatientPop team to 140 employees and 55 million in revenue. Justin Welsh | SVP Sales @ PatientPop. Want to see more content like this?

Sales Recruiting 330

Sales Recruiting Sales Hiring Scale Sales 330

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. Create/ track a leaderboard so i f someone is below average in sales, it’s objective. If you look at the number of Sales vs. Marketing.

Sales Hiring 281

Sales Hiring Underperforming Technical Team Revenue Sales 281

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

OCTOBER 30, 2021

I asked Aasif Osmany to share his learnings as a top-performing SMB VP of Sales, below. I considered the four companies and chose Gorgias based on my experience with their team during the interview process. While at Gorgias, I expected to leave with as much knowledge to earn me an honorary bachelor’s in sales.

Scale 284

Scale Sales Hiring Sales Underperforming Technical Team 284

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

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 24, 2020

Sam Blond, CSO at Brex explains why recruiting, networking and employee happiness is the key to this playbook on recruiting your sales team. Sam Blond | Chief Sales Officer @ Brex. I’m doing The Playbook To Recruiting Your Sales Team. Once again, amazing job to the SaaStr team. FULL TRANSCRIPT BELOW.

Sales Recruiting 188

Sales Recruiting Sales Hiring Scale Underperforming Technical Team 188

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

JUNE 13, 2024

What Does AI-Enhanced Sales Look Like In Two Years Everyone’s thinking about it. What does the future of AI-enhanced sales look like from Amit’s perspective? Will a sales executive be able to manage the entire life cycle with AI? Can we get away with fewer sales professionals permanently? First, no drudgery.

Scale 306

Scale AI Sales Underperforming Technical Team 306

SaaStr

JUNE 20, 2023

Almost everyone in sales seems to be into real estate, either “multi-family” real-estate or getting their broker’s license. Especially a VP of Sales, working on a big number, and with presumably, a big upside and OTE? About 3,000 of you think it’s just fine for even a VP of Sales to have a side hustle.

Underperforming Technical Team 322

Underperforming Technical Team Scale Sales Hiring Startup 322

SaaStr

FEBRUARY 16, 2022

He also observed that after product-market fit had been achieved, companies would only ever have to worry about marketing and sales. As companies begin to succeed, they sometimes develop a tunnel vision towards the customers who have brought them their success. Listen to sales. We just have to actively listen.

Underperforming Technical Team 284

Underperforming Technical Team Company Culture Customer Success Product Marketing 284

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 169

AI Search AI Startup Scale 169

Intercom, Inc.

SEPTEMBER 19, 2019

This is the recipe for a mediocre sales team. Like a sports franchise, a top team should be both collaborative and competitive. On this week’s episode, I caught up with Steli to chat all things sales. When not writing his sales handbook, he’s been overseeing the change from Close.io to Close.com.

Sales Hiring 184

Sales Hiring Scale Underperforming Technical Team Sales 184

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. 1/ Want the best startup VP Sales candidates in the world? Only money.

Sales Hiring 336

Sales Hiring Scale Underperforming Technical Team Startup 336

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

MARCH 5, 2025

The 10-Point Checklist for Selling Your Company Understand Buyer Motivations – Have conversations with potential acquirers before announcing you’re for sale to understand what they truly value. Manage Team Expectations – Balance transparency with the need to keep the team focused on building the business.

Technical Review 198

Technical Review Software Review Development Team Review Sales Hiring 198

SaaStr

JANUARY 16, 2023

Not that they are just "great at sales" — Jason Be Kind Lemkin  (@jasonlk) January 12, 2023. So a while back we did a deep dive on why 95% of the VPs of Sales candidates just won’t thrive at your start-up. I think it’s important to repeat that analysis, but for your first few sales reps.

Sales Hiring 326

Sales Hiring Startup Underperforming Technical Team Branding 326

SaaStr

JULY 1, 2020

An open discussion with Sam Blond, CSO at Brex, and Kristen Habacht, VPS at Atlassian, about adjusting their sales process during Covid-19. Kristen Habacht runs EDR sales at Atlassian, which I got a check today, $40 billion-$50 billion company. She manages a huge global team. Four, people in the sale? Jason Lemkin: None.

Merchant Services 255

Merchant Services Scale Sales Recruiting Sales 255

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 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. In this talk, CircleCI VP of Revenue Jane Kim will talk about the 5 mistakes all new sales leaders make. She said, “Your team really needs to get to know you. FULL TRANSCRIPT BELOW.

Scale 178

Scale Sales Hiring Scaling Underperforming Technical Team 178

SaaStr

MARCH 22, 2024

After switching to SaaS, she started as an SMB sales leader with no prior management or SMB sales experience. She wanted to jump into a full cycle capacity as a sales leader, but she said yes. Shifting from an operator and loving operations and data to a sales and revenue leadership role felt like a big jump.

Scale 300

Scale Underperforming Technical Team SMB Finance 300