Enterprise and Sales Recruiting

How Windsurf / Codeium Built a Billion-Dollar AI Company and a Winning Sales Machine

SaaStr

MARCH 23, 2025

5 Key Learnings from Scaling from 3 to 75 Go-To-Market Team Members in Less Than 12 Months The latest SaaStr CRO Confidential is out and Sam Blond did a great deep dive with Graham Mareno, VP of Worldwide Sales at Codeium. Create Compelling Economic Incentives For sales talent, compensation is critical.

Sales Recruiting

Sales Recruiting Sales Hiring Scale AI

3 Key Steps to Successfully Recruit a VP of Sales with Greenhouse

SaaStr

JULY 13, 2023

A strong sales leader is vital to any company hoping to scale. With this in mind, hiring for the Head of Sales role is one of the most important things a business can do. Unfortunately, too many companies focus on the wrong things when hiring their sales leaders, which can lead to hires that aren’t the best fit for the business.

Sales Recruiting

Sales Recruiting Sales Hiring Scale Sales

Running the Enterprise Playbook with Envoy Head of Enterprise Sales Sarah Lash (Video)

SaaStr

JANUARY 31, 2022

Having learned from thousands of customers and prospects, Sarah Lash, Envoy’s head of enterprise sales, will talk about what it takes to guide and scale enterprise sales programs during an uncertain future. In my first six months at Envoy , I grew the sales team from six to 17. Combine Strategies To Drive Sales.

Sales Recruiting

Sales Recruiting Sales Hiring Scale Enterprise

Dear SaaStr: Should I Move My Start-Up to SF Bay Area?

SaaStr

JUNE 6, 2025

Whether it’s hiring a VP of Sales who’s scaled a team to $50M ARR or finding a product leader who’s built enterprise-grade solutions, the talent pool here is unparalleled. #2. Legitimacy and Credibility Being based in the Bay Area still signals legitimacy, especially when selling to enterprise customers or raising capital.

Sales Recruiting

Sales Recruiting Scale Sales Hiring B2B

The Playbook to Recruiting Your Sales Team with Brex Chief Sales Officer Sam Blond (Video + Transcript)

SaaStr

MARCH 24, 2020

Nothing matters but recruiting and using your personal network. 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.

Sales Recruiting

Sales Recruiting Sales Hiring Scale Underperforming Technical Team

Dear SaaStr: How Can I Crush a VP of Sales Interview?

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

Sales Recruiting Interviewing Sales Hiring Scale

Scaling A SaaS Sales Team While Building Culture with Scott Pugh, VP of Sales at Figma (Pod 639 + Video)

SaaStr

MARCH 3, 2023

At SaaStr APAC 2023, Scott Pugh, VP of Sales at Figma, shared how to scale these two sales teams while building culture. Pugh’s strategy is simple, albeit not always easy: Recruitment — how to hire the best talent to scale your sales organization. Let’s look at five tips to consider for successful recruiting.

Scale

Scale Sales Recruiting Sales Hiring Scaling

The Playbook to Building a Thriving Sales Culture with PatientPop SVP of Sales Justin Welsh (Video + Transcript)

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. I was a local sales manager or regional manager.

Sales Recruiting

Sales Recruiting Sales Hiring Scale Sales

5 Nonobvious Learnings from Atlassian’s Path to The First $10B in ARR With Ex-CRO Cameron Deatsch

SaaStr

FEBRUARY 16, 2025

The “Anti-Enterprise” Enterprise Model Most surprising insight: Atlassian’s growth challenges conventional enterprise wisdom. While competitors invested in huge sales teams, Atlassian actually restricted direct customer interaction. 5 Nonobvious Learnings from Atlassian’s Path to $10B 1.

Sales Recruiting

Sales Recruiting Marketplace as a Service Underperforming Technical Team Scale

5-6 Years Is About As Fast As You Can Mint a True VP of Sales

SaaStr

MARCH 18, 2021

We’ve talked a lot about hiring a VP of Sales at SaaStr , and if you hire a stretch VP of Sales (as most of you will) … how much you can stretch. A related question is — just how quickly can you gain the requisite experience to be a true first time VP of Sales? Month 16: promoted to enterprise rep.

Sales Hiring

Sales Hiring Sales Recruiting SMB Sales

Want to Get Ahead in Sales? Make Sure You Pick the Right Track

SaaStr

JUNE 26, 2023

Dear SaaStr: What’s the Best Way to Get Ahead in SaaS Sales? It is important to decide which of 3 life tracks you want to be on: Super-successful sales rep / individual contributor. Successful sales manager. I.e., become a VP of Sales someday. Leverage “sales” to become a founder, business owner , etc.

Sales Recruiting

Sales Recruiting Sales Hiring Sales SMB

What’s The #1 Challenge After $1m-$2m ARR?

SaaStr

JUNE 23, 2020

In SaaS, it is recruiting your VPs and management team : SaaS products mostly don’t sell themselves. You can hack managing and finding 1–3 reps yourself, but after that, you really need a VP of Sales. Q: What’s the number one challenge for scale-up founders? You’ll need more than 5–6 core engineers to go big.

Part-Time VPE

Part-Time VPE CTO Hire Fractional VPE Sales Recruiting

Top 10 Mistakes Getting to $100M ARR with LaunchDarkly’s Co-founder Edith Harbaugh (Pod 668 + Video)

SaaStr

JUNE 21, 2023

They hired their first VP of Sales with a wonderful pedigree and experience at some of the hottest startups. because they needed to rebuild the sales team. They rebuilt the sales team and closed some big deals. A good executive recruiter is like a real estate agent or matchmaker. A good recruiter is worth it.

Sales Recruiting

Sales Recruiting Sales Hiring Underperforming Technical Team Pricing

Now, For the First Time Ever, You Really Can Hire “Bay Area VPs” Anywhere in the World. Carpe Diem.

SaaStr

NOVEMBER 5, 2020

It’s an even bigger deal in the enterprise, where the playbook to closing large deals is more critical to have down. The companies that create the SVPs you’ll need, especially in Sales and Marketing, are still mostly based in the SF Bay Area. Even today. With SMBs, you can hack it a bit more. At least, not for now.

Sales Hiring

Sales Hiring Sales Recruiting Scale Scaling

How We Increased Sales Nearly 100% In One Quarter

SaaStr

JUNE 9, 2021

A ways back, I asked Brendon Cassidy, VP of Sales at LinkedIn, Adobe Sign / EchoSign, and Talkdesk to put together his playbook for double sales. … How We Increased Sales Nearly 100% In One Quarter at HackerRank – Brendon Cassidy. I thought it was a great checklist for all of us to take a look at.

Scale

Scale Sales Recruiting Sales Hiring Sales

Top 10 Unexpected Learnings from Scaling Wiz From $0 to The First $100M ARR with founding CRO Colin Jones and Sam Blond

SaaStr

MARCH 18, 2025

Rather than seeing this as a liability, Wiz leveraged it as a strategic advantage — even in its sales team. By building operational capacity ahead of revenue, they avoided the common trap of having sales capabilities outstrip the organization’s ability to deliver and support those sales.

Scale

Scale Sales Hiring Scaling Headcount

10 Things That Would Have Helped Me Go From $1m to $10m Faster with Less Stress

SaaStr

MARCH 7, 2021

I thought it would be worth drilling down deeper into each of them, and sharing the learnings and mistakes: 1/ Spending less time fixing things, more time recruiting senior folks to own them. No one spends enough time recruiting as it is, after $1m ARR or so. Yes, you can manage the sales team yourself. You can do this.

Part-Time VPE

Part-Time VPE Sales Recruiting Sales Hiring Scale

If You Don’t Think You Need a VP of Product, VP of Marketing, Etc. — Then You Haven’t Worked With a Great One

SaaStr

DECEMBER 10, 2020

I hear again and again from SaaS founders growing to $5m, $10m ARR or even more that they don’t need a certain VP — with the exception of a VP of Sales. Basically, in SaaS, everyone “gets” that they need a VP of Sales. To get to $5m-$10m ARR and beyond, we’ll need a real VP of Sales. But trust me.

Sales Hiring

Sales Hiring CTO Hire Sales Recruiting Scale

Building a Successful Customer Advisory Board in the Enterprise with Mapistry’s VP of Customer Experience Maya Colato

SaaStr

MARCH 18, 2022

Mapistry recruited a diverse pool by inviting both legacy customers and new customers. . New customers add value to your CABs with their fresh experience with your sales cycle and onboarding processes. Which customer segments best represent your growth focus? Keep in mind that prospective board members lead busy lives.

Sales Recruiting

Sales Recruiting Enterprise Onboarding Investment

If Your VP Hasn’t Done Some Key Part of the Job by Day 90. He Never Will.

SaaStr

MARCH 19, 2021

A head of sales that doesn’t recruit at least one strong rep in the first 90 days. A VP of Sales that has never done outbound, if they don’t take it on fairly early — they never really will. But the top VPs of Sales know you have to get it going soon. Never will. That hits quota or better. Never will.

Sales Recruiting

Sales Recruiting Sales Hiring SMB Engineering

The Beauty and ROI in The Zero Voluntary Attrition Sales Team

SaaStr

OCTOBER 5, 2020

There’s a common thinking that sales teams should be relatively high churn. That the bottom 15-20% of the sales team almost has to churn each year, because it’s survival of the fittest. At Salesforce, at Box, the bottom end of the sales team churns out each year. First, do sales reps really compete with each other?

Scale

Scale Sales Hiring Sales Recruiting Sales

Does Your VP of Sales Need to be An Expert In Your Product?

SaaStr

MARCH 25, 2023

So one recent survey we did really brought out a healthy debate: does your VP of Sales really need to be a product expert? Many of the comments said it was more important a VP of Sales understand process and leadership more than the product itself. They often melt. I say, you just gotta know the product. Not just with buzzwords.

Scale

Scale Sales Hiring Sales Recruiting Sales

Dear SaaStr: What’s The Number One Challenge for Scale-Up Stage Founders?

SaaStr

MARCH 1, 2024

In SaaS, once you have even a few million in ARR, the #1 challenge is recruiting top-tier VPs and building a truly top-tier management team: SaaS products mostly don’t sell themselves. You can hack managing and finding 1–3 reps yourself, but after that, you really need a VP of Sales. She can be your CTO forever.

Scale

Scale Part-Time VPE CTO Hire Fractional VPE

How to Attract, Hire & Build a Diverse Sales Team with Handshake VP, Employer Partnerships Jessica Peluso (Video)

SaaStr

MARCH 22, 2022

I really appreciate you coming to talk about how to attract, hire, and build a more diverse sales team in your organization. So I’ve been building top-producing sales teams for a really, really long time. So over the years, I’ve watched many sales leaders go out and say, “Brian’s my top producer.

Sales Hiring

Sales Hiring Sales Recruiting Scale Sales

SaaStr Podcast 453 (and Video): Building a Second Unicorn: A Deep Dive With Jyoti Bansal

SaaStr

JUNE 15, 2021

Recruitment: Getting the right talent onboard is a critical step. Sales: You must understand how to grow your sales machine, and it isn’t easy. Sales: You must understand how to grow your sales machine, and it isn’t easy. In fact, you need both to optimally grow your sales efforts. Surprises Along the Way.

Sales Recruiting

Sales Recruiting Scale Software Delivery Travel

My Top 10 Year One SaaS Mistakes. Save Yourself Some Pain & Just Don’t Make Them Yourself.

SaaStr

JANUARY 25, 2021

If I had, I would have better understood the likely end point vis-a-vis freemium vs. enterprise. Not Hiring 2-3 Sales Reps to Start. More on that here: When You Hire Your First Sales Rep — Just Make Sure You Hire Two. Our first ‘enterprise’ customer seemed like an outlier. We should have taken $2m more.

Sales Recruiting

Sales Recruiting Sales Hiring Scale SaaS

What CEOs Should Know About Recruiting Top Talent

OpenView Labs

APRIL 29, 2021

Recruiting top talent is the common denominator across all scaling startups. Nine out of 10 founders and CEOs I connect with are involved in recruiting on a weekly, if not daily, basis. Many of them are learning on the fly and trying to juggle being CEO and Chief People Officer/Lead Recruiter/Brand Evangelist all at once.

Sales Recruiting

Sales Recruiting Outsourcing Services Sales Hiring Scale

The $939B Question: Is AI Eating SaaS or Feeding It?

SaaStr

JUNE 20, 2025

The Great Spending Showdown: AI vs SaaS in 2025/2026 — What Every B2B Leader Needs to Know We’re witnessing the most dramatic shift in enterprise tech spending since the cloud migration began 15 years ago. billion valuation after 175M round Scale AI : $29 billion valuation / “sale” with Meta’s $14.3

AI Search

AI Search Artificial Intelligence AI CTO Hire

The Top 10 Worst Pieces of SaaS Advice

SaaStr

JANUARY 27, 2021

“Give the VP of Sales More Time” This is always terrible advice. If a VP of Sales can’t improve things in one sales cycle or less — she never will. In one sales cycle, or less. RFPs are part and parcel of real enterprise deals. They’re for Enterprise Winners. ” No.

Part-Time VPE

Part-Time VPE Sales Hiring Scale Sales Recruiting

What Order Should You Hire Your Management Team In?

SaaStr

NOVEMBER 19, 2020

More on that here and a great video discussion below: You’ll probably be ready for your first VP of Sales by $1m in ARR. We’ve talked about this a lot on SaaStr, but hiring a true VP of Sales before you have 2 reps hitting quota (and thus a repeatable, if not yet fully repeating process) is too early. Earlier is better.

Part-Time VPE

Part-Time VPE Sales Hiring CTO Hire Scale

How Data-Driven Recruiting Helps Sales Leaders Make the Right Hire with Mike Levy

Sales Hacker

MAY 18, 2021

On today’s episode of Sales Hacker podcast, we have Mike Levy of TitahHouse, a transparent and effective platform, loaded with in-depth career and job intelligence, exclusively designed to connect tech-focused sales professionals with their next great position. Subscribe to the Sales Hacker Podcast. Special Announcement.

Sales Recruiting

Sales Recruiting Sales Hiring Data Sales

“Talk to You in 2025”: When There Isn’t Budget

SaaStr

JANUARY 18, 2023

It’s the most common objection you’ll get in SaaS sales … Not Right Now. It can’t strategically improve sales software, financial software, quoting software, recruiting software, QA processes, call center software, etc. It usually takes 3-4 years in the enterprise for this to happen, 1-2 in SMBs. I Don’t Have Budget.

Sales Recruiting

Sales Recruiting Sales Hiring Technical Review Software Review

On Recruiting: The Must-Have / Nice-to-Have List

Kellblog

MARCH 17, 2020

Rephrasing Lewis Carroll, “if you don’t know what you’re recruiting for, any candidate looks great.” ” I liken executive recruiters to Realtors. ” That know-not-what, by the way, is that it’s for sale. Let’s switch to executive recruiting. Sound judgment and maturity.

Sales Recruiting

Sales Recruiting Sales Enablement Startup Communication

Should Google acquire Salesforce?

SaaStr

JANUARY 9, 2020

For example, Google put a lot of work into Google Hire, its recruiting SaaS product. Salesforce is really 4+ clouds that are all at scale (sales, marketing, commerce and platform). Accelerated Enterprise Credibility. Everyone in Cloud is now dueling in the enterprise. But then shut it down. Salesforce.

Sales Recruiting

Sales Recruiting Scale Sales Hiring Cloud

CRO Confidential: Principles that drove Wiz’s $0 to $100M Journey with Wiz CRO Colin Jones (Pod 665 + Video)

SaaStr

JUNE 2, 2023

The company helps enterprises internationally with contextual and actionable insights to secure their cloud infrastructure. Recruit diverse leaders The goal of hiring a revenue leader is to put gasoline on finding product market fit success. CROs should focus on capturing that unrealized demand which is not a sales-led effort.

Sales Recruiting

Sales Recruiting Sales Hiring Scale Branding

Be Careful Hiring “Dualies” — Folks That Are a VP of More Than One Thing

SaaStr

OCTOBER 9, 2020

A VP of Sales and Success A VP of Sales and Marketing A VP of Sales and Anything Else. Is usually not really a VP of Sales. I don’t know about you, but I’ve had to recruit a lot of types of folks over the years where my domain knowledge was limited. I’ve had to recruit Ph.Ds. Not really.

Sales Hiring

Sales Hiring Part-Time VPE CTO Hire Sales Recruiting

The SaaS Org Chart Live with David Sacks (Podcast #491 and Video)

SaaStr

NOVEMBER 16, 2021

In 2008, he founded Yammer, an enterprise software company that David grew to 500 employees and $60 million in sales. Head of Sales. Positions Needed: Enterprise AEs, Mid-Market & SMB AEs, SDRs, Sales Ops, Sales Engineer. Positions Needed: FP&A Analyst, Accountant, HR, Ops, Recruiter.

CTO Hire

CTO Hire Sales Hiring Sales Recruiting CTO

The Curious Case of The Stubbornly High OTE

SaaStr

AUGUST 29, 2023

So I was on a group Zoom with a number of CROs and VPs of Sales the other day and a consistent theme came up: everyone was surprised how high OTEs (On Target Earnings) had held up in the current environment. An enterprise rep might be looking for a $200k OTE, with say a $100k base and a $100k bonus. Look, it just makes sense.

Sales Recruiting

Sales Recruiting Venture Capital Enterprise Sales

What Does — And Doesn’t — Get Easier After $10m ARR

SaaStr

JANUARY 23, 2024

Efficiency goes down in other places (sales efficiency usually, marketing efficiency often). Account expansion starts to work. The best mid-market and enterprise SaaS companies grow their accounts 120%-160% as a cohort, inclusive of churn. It’s much cheaper to renew a customer than to acquire one. You have redundancy.

Sales Recruiting

Sales Recruiting Scale Branding Scaling

What SaaStr CEO and Founder Jason Lemkin Really Thinks About AI, Sales & Lead Gen In 2024

SaaStr

OCTOBER 25, 2023

For part one of this Ask Me Anything session, Jason covers everything you need to know about hiring your first VP of Sales, what he really thinks about AI, what the future of lead generation in 2024 looks like, and much more. Lead generation tools do change, but the basic motions of sales and marketing haven’t changed much.

Scale

Scale Sales Hiring Sales Recruiting AI

What Could Possibly Go Wrong? Scaling from 2 to 200 Employees and 0 to 75,000 Customers with Storyblok CEO Dominik Angerer and VP of Operations Lydia Kothmeier (Video)

SaaStr

FEBRUARY 27, 2023

They credit this growth to their global team, a switch to an enterprise business model switch, and flexible work operations. Storyblok started with a leadership-first hiring plan and a recruitment strategy that involved the following: A test to know how candidates handle different tasks and their expertise level.

Scale

Scale Sales Hiring Sales Recruiting Scaling

How Windsurf / Codeium Built a Billion-Dollar AI Company and a Winning Sales Machine

3 Key Steps to Successfully Recruit a VP of Sales with Greenhouse

Trending Sources

Running the Enterprise Playbook with Envoy Head of Enterprise Sales Sarah Lash (Video)

Dear SaaStr: Should I Move My Start-Up to SF Bay Area?

The Playbook to Recruiting Your Sales Team with Brex Chief Sales Officer Sam Blond (Video + Transcript)

Dear SaaStr: How Can I Crush a VP of Sales Interview?

Scaling A SaaS Sales Team While Building Culture with Scott Pugh, VP of Sales at Figma (Pod 639 + Video)

The Playbook to Building a Thriving Sales Culture with PatientPop SVP of Sales Justin Welsh (Video + Transcript)

5 Nonobvious Learnings from Atlassian’s Path to The First $10B in ARR With Ex-CRO Cameron Deatsch

5-6 Years Is About As Fast As You Can Mint a True VP of Sales

Top SaaStr Content for the Week: Grammarly’s CEO, CRO Confidential, Braze’s CEO and lots more!

Want to Get Ahead in Sales? Make Sure You Pick the Right Track

Top SaaStr Content for the Week: CRO Confidential, Workshop Wednesday and more!

What’s The #1 Challenge After $1m-$2m ARR?

Top 10 Mistakes Getting to $100M ARR with LaunchDarkly’s Co-founder Edith Harbaugh (Pod 668 + Video)

Now, For the First Time Ever, You Really Can Hire “Bay Area VPs” Anywhere in the World. Carpe Diem.

How We Increased Sales Nearly 100% In One Quarter

Top 10 Unexpected Learnings from Scaling Wiz From $0 to The First $100M ARR with founding CRO Colin Jones and Sam Blond

10 Things That Would Have Helped Me Go From $1m to $10m Faster with Less Stress

If You Don’t Think You Need a VP of Product, VP of Marketing, Etc. — Then You Haven’t Worked With a Great One

Building a Successful Customer Advisory Board in the Enterprise with Mapistry’s VP of Customer Experience Maya Colato

If Your VP Hasn’t Done Some Key Part of the Job by Day 90. He Never Will.

The Beauty and ROI in The Zero Voluntary Attrition Sales Team

Does Your VP of Sales Need to be An Expert In Your Product?

Dear SaaStr: What’s The Number One Challenge for Scale-Up Stage Founders?

How to Attract, Hire & Build a Diverse Sales Team with Handshake VP, Employer Partnerships Jessica Peluso (Video)

Top SaaStr Content for the Week: Mailchimp’s Co-Founder, Y Combinator’s CEO, Workshop Wednesday and More!

SaaStr Podcast 453 (and Video): Building a Second Unicorn: A Deep Dive With Jyoti Bansal

My Top 10 Year One SaaS Mistakes. Save Yourself Some Pain & Just Don’t Make Them Yourself.

What CEOs Should Know About Recruiting Top Talent

The $939B Question: Is AI Eating SaaS or Feeding It?

The Top 10 Worst Pieces of SaaS Advice

What Order Should You Hire Your Management Team In?

How Data-Driven Recruiting Helps Sales Leaders Make the Right Hire with Mike Levy

“Talk to You in 2025”: When There Isn’t Budget

On Recruiting: The Must-Have / Nice-to-Have List

Should Google acquire Salesforce?

CRO Confidential: Principles that drove Wiz’s $0 to $100M Journey with Wiz CRO Colin Jones (Pod 665 + Video)

Be Careful Hiring “Dualies” — Folks That Are a VP of More Than One Thing

The SaaS Org Chart Live with David Sacks (Podcast #491 and Video)

The Curious Case of The Stubbornly High OTE

What Does — And Doesn’t — Get Easier After $10m ARR

What SaaStr CEO and Founder Jason Lemkin Really Thinks About AI, Sales & Lead Gen In 2024

What Could Possibly Go Wrong? Scaling from 2 to 200 Employees and 0 to 75,000 Customers with Storyblok CEO Dominik Angerer and VP of Operations Lydia Kothmeier (Video)

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