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

Sales Hacker

JUNE 20, 2025

People post in our Slack channel that they’re hiring but it’s not posted. And in a world of layoffs, AI disruption, and hiring freezes, your next opportunity will increasingly come through backchannels, not applications. Engage venture networks (the right way) VC talent teams can be a cheat code (and of course, we’re a little bias).

Sales Hiring 95

Sales Hiring Sales Recruiting AI Search Scale 95

SaaStr

NOVEMBER 9, 2020

Maybe: – Go grab that office lease at half off – Hire Bay Area VPs now while they'll work anywhere. My top suggestions: Hire those “Bay Area VPs” now while they’ll (still) work with startups HQ’d anywhere. Go hire those VPs now that aren’t in your city. Make the hires.

Underperforming Technical Team 328

Underperforming Technical Team Sales Hiring Travel Cloud 328

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. This structure enables a seamless experience that starts when a company hires someone.

Startup 152

Startup Sales Hiring Underperforming Technical Team Cloud 152

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. Account management? Can you do truly competitive sales? But larger sales organizations put sales operations processes in place that keep you more organized.

Sales Hiring 344

Sales Hiring Underperforming Technical Team Branding Pricing 344

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. Which role should you hire for first? And for good reason. One thing is the timing.

Sales Hiring 258

Sales Hiring Underperforming Technical Team Development Team Review CTO Hire 258

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 331

Sales Recruiting Sales Hiring Scale Sales 331

SaaStr

JANUARY 29, 2023

Basically all of the SaaS CEOs/founders I know of have made at least one terrible VP+ level hire. 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). Only money. First, some context.

Sales Hiring 333

Sales Hiring Scale Underperforming Technical Team Startup 333

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 275

Sales Hiring Underperforming Technical Team Revenue Sales 275

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 322

Sales Hiring Startup Underperforming Technical Team Branding 322

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 290

Scale Sales Hiring Underperforming Technical Team Sales 290

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 284

Sales Recruiting Sales Hiring Scale Outsourced Development 284

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. A bad one can torpedo you.

Sales Recruiting 286

Sales Recruiting Sales Hiring Underperforming Technical Team Pricing 286

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 320

Scale Sales Hiring Venture Capital Marketing 320

SaaStr

OCTOBER 30, 2021

I asked Aasif Osmany to share his learnings as a top-performing SMB VP of Sales, below. Together we combed through AngelList and found companies that we saw potential in, however, most were not hiring. I considered the four companies and chose Gorgias based on my experience with their team during the interview process.

Scale 278

Scale Sales Hiring Sales Underperforming Technical Team 278

Intercom, Inc.

MARCH 12, 2019

A little over a year ago, I got the opportunity to start a new team within our sales organization – a team of Relationship Managers dedicated to growing our current customers at scale. The opportunity emerged out of a shift in how we practice sales. We had split into two distinct but complementary functions.

Sales Hiring 171

Sales Hiring Sales Recruiting Underperforming Technical Team Scale 171

Neil Patel

OCTOBER 25, 2020

But should you build your own in-house marketing team or hire an agency partner? Digital agencies are companies that help other businesses perform a specific function such as marketing, development, or design. They act as a substitute for an in-house team, serving the same labor function but outside of the organization.

Sales Hiring 145

Sales Hiring Outsourcing Services Underperforming Technical Team Sales Recruiting 145

Sales Hacker

APRIL 30, 2020

What’s your approach when hiring sales reps? Companies often hire sales reps who have knowledge of, or even a passion for, the brand’s product or industry — which is great because it gives you a team of “walking brochures” who can spout off all the benefits of your product. The best training for new sales hires.

Sales Hiring 114

Sales Hiring Sales Recruiting Sales Underperforming Technical Team 114

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 187

Sales Recruiting Sales Hiring Scale Underperforming Technical Team 187

SaaStr

DECEMBER 1, 2023

Hiring a VP of Sales isn’t new, but the conversations have evolved as the world has. SaaStr’s own Jason Lemkin shares the top 10 mistakes he sees during the hiring process during Workshop Wednesday, held every Wednesday at 10 a.m. The last 18 months have seen the biggest changes in the VP of Sales in his SaaS career.

Sales Hiring 152

Sales Hiring Sales Recruiting Sales Interviewing 152

SaaStr

JULY 15, 2022

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: I’ll answer it, but are you thinking more on sales or technology or broadly speaking in the question? That’s a great example.

Scale 286

Scale Outsourcing Services Sales Hiring VP of Engineering 286

SaaStr

JULY 1, 2021

For us, it’s about fixing this problem, serving the customer well, so a very service driven mindset, which I gave a talk on a few days ago here, has been a big part of Gusto and affected our hiring from the early days. The second is pulling more around values, and how we approached team building. Get tickets here. TRANSCRIPT.

VP of Engineering 286

VP of Engineering Sales Hiring Sales Recruiting Underperforming Technical Team 286

SaaStr

APRIL 5, 2023

A bad experience with a revenue operations leader might taint your view of the position at all future companies, but that would be a mistake, as CRO Confidential podcast host Sam Blond learned first-hand. Considering aspects of sales and GTM strategies. A good range for this hire might be between 2-8 sales reps.

Sales Hiring 245

Sales Hiring Education Scale Strategy 245

SaaStr

JULY 25, 2021

They talked about product adoption, sales alignment, freemium models and lessons they have learned throughout their successful SaaS careers. As two CEO who love the art of sales and scaling, this one really was special. You can have the great product and a great team, but the market of small or very niche. Jyoti Bansal: Yeah.

Sales Recruiting 258

Sales Recruiting Sales Hiring Scale VP of Engineering 258

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 201

Technical Review Software Review Development Team Review Sales Hiring 201

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. Let me start by telling you about my first role as a manager. FULL TRANSCRIPT BELOW.

Scale 181

Scale Sales Hiring Scaling Underperforming Technical Team 181

OpenView Labs

MARCH 8, 2021

B2B sales involves one business selling its product to another business. Those with experience in both B2B and B2C sales know that B2B is a lot tougher—the deals are bigger, there’s often more than one decision-maker, and the competition is intense. For all those reasons, hiring and management must be on point.

Sales Hiring 98

Sales Hiring Scale Sales Recruiting B2B 98

SaaStr

OCTOBER 26, 2023

Getting off the ground is one thing — an easy pitch of being an HR tech startup focused on improving hiring. Hiring is complicated, so you have to build a lot of software to get to $200M ARR. Now, over the next decade, they need to think about other things their customers do in hiring that aren’t done well and could be scaled.

Sales Hiring 274

Sales Hiring AI SMB Scale 274

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

Sales Hacker

JUNE 17, 2025

At Procore, he led all customer-facing functions—Sales, Marketing, CS, RevOps, and BD. But behind every product launch and revenue milestone is a team – and building that team is one of the hardest and important parts of the journey. It’s the one person that can hire or fire you. It drives employee engagement.

AI 81

AI Technical Advisors Underperforming Technical Team Sales Hiring 81

SaaStr

JUNE 7, 2021

If you don’t have tickets, lock in Early Bird pricing today and bring your team! When you get that thing where you’re a rational person and you think it will be great and 99 out of 100 people think it’s bad, that’s when you have opportunity. I was a software developer, a product person. Get tickets here.

Sales Hiring 337

Sales Hiring Underperforming Technical Team SaaS Headcount 337

Intercom, Inc.

JUNE 21, 2018

Whether you’re at an early-stage startup that’s just made its first sales hires, or part of a fast-moving sales team in a large organization, the key to success often comes down to efficiency. That means your focus should be on building the right customer profile and developing precise messaging to reach them.

Sales Hiring 183

Sales Hiring Scale Sales Recruiting Technical Advisors 183

SaaStr

NOVEMBER 1, 2022

They are hiring leaders, building teams, and attracting advisors in the US while devouring the SV SaaS playbook. AI is likely the next platform, dev tools are strategic given the scarcity of developers, cybersecurity is front and center for enterprises, and the data stack is still going strong. Proximity to customers helps too.

Scale 286

Scale Sales Hiring Underperforming Technical Team Cybersecurity 286

SaaStr

JANUARY 24, 2024

How should you handle presenting challenges to your C-suite team when you’ve just joined the company? She was hired because they saw a bit of softening in new business growth, and she came to help diagnose what was going on and help scale the business. The bad news is it wasn’t driving the results they wanted.

Scale 268

Scale Sales Hiring Scaling Revenue 268

Intercom, Inc.

APRIL 4, 2019

The fastest growing software companies in recent years all have something in common – they started with little to no sales team. But even for companies with this early viral growth, there comes a point in time when this organic growth needs to be supplemented with formal sales. Yes, Slack started off with no sales team.

Scale 162

Scale Sales Hiring Underperforming Technical Team Payment Services 162

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. The critical role of product managers and ways to utilize them effectively. How many of you guys’ product rely on the highly functioning engineering team?

Scale 311

Scale Underperforming Technical Team Sales Hiring Engineering 311

FastSpring

FEBRUARY 6, 2025

If you’re running a smaller digital business, you may find it challenging to hire great talent. If you’re facing challenges winning the best candidates for your roles, or if you have a small number of roles and every hire really matters, then don’t miss this episode of Growth Stage. X sales force, X meta.

SMB 106

SMB Sales Recruiting Branding Sales Hiring 106