SaaStr

FEBRUARY 22, 2022

Ok we’ve talked a bit more on SaaStr over the years on how to hire a Great VP of Sales , but hiring a Great VP of Marketing is just as important. Maybe in some ways more so, in that you can generally hire a great VP of Marketing earlier. Do you make the hire now? Not just in sales. What do I mean?

Sales Hiring 301

Sales Hiring Growth Hacking B2C SMB 301

SaaStr

SEPTEMBER 19, 2023

based SMB sales positions. SaaS sales execs with even a little bit of experience at other SaaS companies are looking for higher and higher OTEs, often with lower effective attainment and high support costs. based sales reps often aren’t really willing to work, or excel, at sub-$100k OTEs anymore. customers?

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SMB Scale Sales Hiring Sales 312

SaaStr

MARCH 29, 2020

We put out a thread here you can click on for a deep dive on 100s of SaaS openings from SaaStr CEOs: Are you hiring? Respond with a link to your top hire to make, etc. They include: Auren Hoffman and Safegraph hiring 3 in sales and 5 in engineering. Matt Mullenweg and Automattic hiring 100s. — Jason ?InItTogether?

Sales Hiring 266

Sales Hiring SaaS SMB Content Marketing 266

SaaStr

APRIL 28, 2025

The Journey: From WiFi to IoT Fleet Management Sekar’s journey began unexpectedly when he joined Meraki (founded by MIT researchers Sanjit Biswas and John Bicket) to help them figure out marketing and sales “from first principles.” This cross-pollination effect accelerated product development in unexpected ways.

Scale 259

Scale Transportation Scaling SMB 259

SaaStr

JANUARY 8, 2025

When Lindsey joined, she inherited an already built-out self-serve/PLG model for small businesses and a mid-market and enterprise sales, customer success, and post-sales team. But at the start of its expansion play, Checkr’s enterprise motion failed, and sales cycles were slow, taking up to a year for $100k & up deals.

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Revenue Scale Sales Hiring Compensation 293

SaaStr

JANUARY 23, 2025

You need: Sales leaders who understand complex, multi-stakeholder deals Customer success teams ready for high-touch support Legal expertise for enterprise contract negotiation Product leaders who can balance current needs with future vision Pro tip: Hire enterprise reps in pairs. Waiting too long to start their enterprise planning.

Enterprise 242

Enterprise Sales Hiring Scale Outsourced Development 242

SaaStr

SEPTEMBER 24, 2020

That when you make a mis-hire, you'll always look back and say you should have made a change 3-4 month earlier? When to hire them. 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.

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Sales Hiring Part-Time VPE Scale Underperforming Technical Team 259

SaaStr

FEBRUARY 24, 2022

I’ve recently had several different conversations with founders looking to hire “PLG experts”. One wanted to hire “Mr/Ms PLG” to make their product more viral. It’s too early in this PLG cycle to hire a “VP of PLG”. Instead: * Hire a great VP of Product with strong freemium experience. Probably in that order.

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Sales Hiring Scale SMB Acquisition 273

SaaStr

APRIL 30, 2024

How do you build GTM efficiency in SMB sales? While this title is SMB-oriented, the advice applies to Mid-Market and Enterprise, too. You shouldn’t be adding a bunch of sales reps or spending a bunch of money on marketing if the economics aren’t sustainable. Kyle made this mistake in his first startup.

Scale 300

Scale SMB Sales Hiring Sales 300

SaaStr

MAY 10, 2024

At this week’s Workshop Wednesday, Lucas Price, former SVP of Sales at Zipwhip and founder and CEO at Yardstick, shares his insights on how to hire and build a high-performing sales team. During that time, he wasted a lot of money on failed sales hires and decided to learn everything about hiring sellers.

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Sales Hiring Scale Sales Interviewing 244

FastSpring

FEBRUARY 6, 2025

If you’re running a smaller digital business, you may find it challenging to hire great talent. In this episode of Growth Stage, we interview Lizzie Mintus Founder and CEO of Here’s Waldo Recruiting and host of The Heres Waldo Podcast about her thoughts on: The most effective recruiting strategies for SMBs.

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SMB Sales Recruiting Branding Sales Hiring 106

SaaStr

JANUARY 19, 2025

And we’ve done several great live Workshop Wednesdays with top CROs and VPs of Sales in Vertical SaaS in particular recently that are all A+ and worth watching: #1. It takes getting out in the field, and creating a ton of true value — before the sale. #2. See you there! How Kyle does it here: #3. How Kyle does it here: #3.

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Scale Sales Hiring Scaling SMB 189

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 6: promoted to first SMB rep.

Sales Hiring 301

Sales Hiring Sales Recruiting SMB Sales 301

SaaStr

NOVEMBER 6, 2021

The other day Brendon Cassidy, the first head of sales at LinkedIn and the first VP of Sales at $10B Talkdesk, Adobe Sign / EchoSign, and more — and now co-CEO of Cosell — and I caught on what’s changing in the Sales Playbook for 2022. Even in SMB and mid-market. Well in most cases.

Scale 341

Scale Sales Hiring Sales SMB 341

SaaStr

JULY 27, 2022

If a SaaS business hopes to win over the SMB market successfully, it will need a precise GTM approach. Founded in 2015, PayFit is a software company that empowers entrepreneurs and SMBs to digitize payroll and HR processes. Secret 1: A Self-Serve Product is Non-Negotiable For SMBs.

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SMB Sales Hiring Scale B2C 242

SaaStr

JUNE 8, 2024

So David Obrand, CEO of Salesloft, had a great post the other day on consistency being one of the biggest challenges with enterprise sales. In SMB sales, you see the variance in performance among reps really fast, and you can take action fast. That’s the nature of a very short sales cycle. The Best VPs of Sales?

Sales Hiring 293

Sales Hiring Scale Sales SMB 293

SaaStr

JULY 11, 2023

How do you win with a high-velocity sales strategy in a fast-moving, competitive market? In a special session of Workshop Wednesday, Gorgias Founder & CEO Romain Lapeyre and Gorgias VP of Sales & Partnerships Aasif Osmany share their learnings, advice, and hacks for optimizing your sales process. Sign up for free.

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Sales Hiring SMB Sales Recruiting Payment Methods 200

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?

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Sales Recruiting Sales Hiring Scale Sales 312

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. Define your hiring profile. Focus on the hiring profile.

Scale 272

Scale Sales Recruiting Sales Hiring Scaling 272

SaaStr

JULY 1, 2024

It’s less jack-of-all-trade hires, so the knowledge and questions they’ll ask will look a lot different. Either way, ensure the demand gen team sits down with sales and decides which accounts to go after. Either way, ensure the demand gen team sits down with sales and decides which accounts to go after.

Sales Hiring 299

Sales Hiring Scale SMB compliance 299

Clouded Judgement

JUNE 17, 2025

For businesses selling predominantly to SMB customers, these benchmarks are all slightly lower given the higher-churn nature of SMBs. I consider >120% best in class for companies selling to SMBs (like Bill.com). In theory, any growth rate is possible with an unlimited budget to hire AEs.

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Cloud Software Benchmarks Retention 277

SaaStr

JANUARY 21, 2022

Dorian Stone , Head of Organizations Revenue at Grammarly, is here to share lessons from his experience of scaling the company from consumer to SMB to Enterprise to help you steer your expansion efforts in the right direction. The admin, influential decision-makers, and consumer sales reps can be the same people in a Consumer or SMB setting.

Scale 246

Scale SMB Enterprise Sales Hiring 246

SaaStr

OCTOBER 30, 2021

Their CEO will join us at SaaSr Scale 2021 on December 15 to talk about using data to get to 10,000 SMB customers! 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.

Scale 284

Scale Sales Hiring Sales Underperforming Technical Team 284

SaaStr

FEBRUARY 9, 2024

Everything from hiring on the GTM side to layering in a sales-led motion into PLG. Let’s dive into what’s making that hybrid model successful: PLG and Sales Led? Given this, you must understand the role that each facet of the business plays in promoting that product, from marketing and sales to customer service.

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Scale Sales Hiring Sales Marketing 316

SaaStr

DECEMBER 12, 2023

Keybanc and Sapphire have some great overall metrics here : Overall, the media AE closes $750,000 a year, and that’s actually up from 2022 — mainly due to hiring freezes and contractions. Enterprise reps tend to close more ($1m+), and SMB reps less (maybe $500k), with $750k net new bookings per year the median.

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Sales Hiring SMB Enterprise Metrics 333

SaaStr

MAY 5, 2022

What are some of the foundational ways sales leaders can think about building their sales teams as their company continues to expand and grow? There’s no shortage of ways to tackle this challenge, but one thing is clear: build sales teams thoughtfully and intentionally. Principle #1: Ownership is Key.

Scale 246

Scale Sales Hiring Scaling Sales 246

SaaStr

NOVEMBER 16, 2021

You’ll need to hire aggressively to get to the next level and continue that rapid growth. But what roles should you hire for, and what will your org chart look like at each stage? In 2008, he founded Yammer, an enterprise software company that David grew to 500 employees and $60 million in sales. Head of Sales.

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CTO Hire Sales Hiring Sales Recruiting CTO 284

SaaStr

MARCH 17, 2021

The other day, I met with a great founder who talked with me about how he was about to top his VP of Sales. As founders, we often get obsessed with “right timing” hires. You definitely don’t want to hire some SVP of Sales at Salesforce to come be your VP of Sales at $1m in ARR — that we can all agree on.

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Sales Hiring Sales Recruiting Scale SMB 307

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. In a year like this, SMB is doing worse, with a lot more churn and startups going out of business. On websites.

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Sales Hiring AI SMB Scale 276

SaaStr

NOVEMBER 18, 2020

Mistake #1: Hiring Too Inexperienced and Junior Managers and “VPs” Stretch VPs can do amazing things if you get it right. Hiring someone who’s never really been a manager at all, for a management role, for a true “owner” role … is usually a stretch too far. More on that here.

Sales Hiring 363

Sales Hiring Scale SaaS Enterprise 363

SaaStr

JULY 24, 2024

Sign #2: You’re Too Slow to Hire VPs If you want to gauge momentum in a startup, see how quickly they hire VPs. Is it easy to hire mercenary VPs when you’re growing 500%, or you’ve raised $100M? Maybe they made the wrong hire or entered the wrong market. The solution is hiring the right person or relaunching next quarter.

Sales Hiring 301

Sales Hiring Startup Scale SMB 301

SaaStr

JUNE 20, 2023

Dear SaaStr: What remarks have a salesperson said to you that lost them the sale? Sales is there to serve. If sales was routed the wrong lead, that’s the company’s fault, not the prospect’s. I’m basically an SMB these days. And let especially SMBs out if you don’t deliver for them. Yes, you have to do that.

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Sales Hiring Scale Sales SMB 262

SaaStr

SEPTEMBER 15, 2023

Big Bet #2: Find Tomorrow’s Great Anglers — Hire Talent With A Learning Mindset In 2010 and 2011, San Francisco was the place for SaaS talent. So, if he wanted to hire customer support, it could be a biomechanical engineer. Instead of hiring for skill, he focused more on core traits like empathy, patience, and being detail-oriented.

Sales Hiring 284

Sales Hiring Scale SMB SaaS 284

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 157

Sales Hiring Sales Recruiting Sales Interviewing 157

SaaStr

FEBRUARY 8, 2022

Scaling a sales organization isn’t easy. Knowing which metrics matter and how to analyze them to increase your revenue and hit organizational sales goals is essential. . What makes a sales organization grow? What’s the best way to grow a sales organization? Enter your email below for the latest SaaStr updates.

Scale 290

Scale Sales Hiring Compensation Sales 290

SaaStr

APRIL 8, 2023

Over the years, we’ve done just an incredible number of deep dives, AMAs, and more with many of the best CROs and VPs of Sales in SaaS!

Scale 300

Scale Sales Hiring SMB SaaS 300

SaaStr

SEPTEMBER 26, 2019

What we learned from ’08-’09 in SaaS: First, SMB churn went through the roof — as SMBs went under much more quickly and often. As soon as the economy went south, SMBs started to simply go bankrupt and/or shut down. Anyone processing a lot of SMB and credit-card deals saw churn probably double.

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SaaS Payments Sales Hiring Scale SMB 280