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 214

Outsourced Development Underperforming Technical Team Development Part-Time VPE 214

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 233

AI Payment Services Payments Scale 233

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 199

Sales Hiring Marketing Technical Review Underperforming Technical Team 199

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 296

Sales Recruiting Sales Hiring Scale Outsourced Development 296

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 205

Sales Recruiting Marketplace as a Service Underperforming Technical Team Scale 205

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 284

Scale Sales Hiring Underperforming Technical Team Sales 284

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

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 334

Underperforming Technical Team Sales Hiring Travel Cloud 334

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 162

Startup Sales Hiring Underperforming Technical Team Cloud 162

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 328

Scale Sales Hiring Venture Capital Marketing 328

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 268

Sales Hiring Part-Time VPE Scale Underperforming Technical Team 268

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 311

Scale AI Sales Underperforming Technical Team 311

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 290

Scale Sales Hiring Sales Underperforming Technical Team 290

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 286

Sales Hiring Underperforming Technical Team Revenue Sales 286

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 328

Sales Recruiting Sales Hiring Scale Sales 328

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 264

Sales Hiring Underperforming Technical Team Development Team Review CTO Hire 264

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 290

Underperforming Technical Team Company Culture Customer Success Product Marketing 290

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

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 337

Sales Hiring Scale Underperforming Technical Team Startup 337

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 172

AI Search AI Startup Scale 172

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 325

Underperforming Technical Team Scale Sales Hiring Startup 325

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 202

Technical Review Software Review Development Team Review Sales Hiring 202

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 329

Sales Hiring Startup Underperforming Technical Team Branding 329

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 190

Sales Recruiting Sales Hiring Scale Underperforming Technical Team 190

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 21, 2023

They hired their first VP of Sales with a wonderful pedigree and experience at some of the hottest startups. 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.

Sales Recruiting 298

Sales Recruiting Sales Hiring Underperforming Technical Team Pricing 298

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

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 305

Scale Underperforming Technical Team SMB Finance 305

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 233

Underperforming Technical Team Technical Review Scale Headcount 233

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

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 317

Underperforming Technical Team Leadership Outsourced Development Finance 317

FastSpring

JANUARY 23, 2025

Listen for the full insights into: How Flippa.com works to connect for-sale businesses with buyers while managing the complexities of valuation and seller expectations. But if someone’s going to sell something for $250,000, it’s a highly emotional sale. And so you’ve got to get that right.

Scale 121

Scale Entrepreneurship Scaling Underperforming Technical Team 121

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 321

Scale Underperforming Technical Team Sales Hiring Engineering 321

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 259

Merchant Services Scale Sales Recruiting Sales 259

SaaStr

OCTOBER 4, 2024

They built one platform that does it all, but also made it simple so that these small businesses they wanted to serve, could actually use it to grow revenue without needing a developer that they didn’t have. But in consumer that just doesn’t work. At the time, Shopify was still a new player. What product would you recommend?

Revenue 312

Revenue Scale Underperforming Technical Team Sales Hiring 312

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. It’s rare for companies to improve both their sales and margin during a downturn. Key takeaways.

Consulting 49

Consulting Underperforming Technical Team Management Marketing 49