SaaStr

JANUARY 23, 2025

Julie Iskow, CEO of $600m+ public SaaS leader Workiva joined Norwest Venture Partners Sean Jacobson at SaaStr Annual for a deep dive on going More Enterprise. Just look at the numbers: Enterprise customers bring 95%+ best-in-class retention vs. 85% in mid-market. Waiting too long to start their enterprise planning.

Enterprise 244

Enterprise Sales Hiring Scale Outsourced Development 244

SaaStr

JANUARY 31, 2021

The time is probably going to come when you have to build a sales team in SaaS. It may be Day 1 if you have plenty of capital and are selling to large enterprises. It may be X months down the road, once you close a few deals of large enough size ($x,000 ACV) to justify hiring a sales rep. You need at least 2 to learn.

Sales Hiring 328

Sales Hiring Scale Sales Enterprise 328

SaaStr

MAY 26, 2025

So what does that mean for inside sales? A 50/50 Sales Team. At least for SMB and more routine mid-market sales. By 2026, these same AI systems will have evolved to manage entire sections of the sales process autonomously. An A+ AI will soon join every sales call, for real. You’ll Need to Manage Both.

Scale 238

Scale Sales Hiring AI Sales 238

SaaStr

NOVEMBER 19, 2020

IME, rough order to make hires in: VPM: $0.2m He asked which to hire first. If you have a few nickels in the bank, and you somehow find a great VP a half stage or even full stage early, just hire her. Hiring is so hard as it is. Make the hire now. ARR VPS: $1-$1.5m More here: [link].

Part-Time VPE 363

Part-Time VPE Sales Hiring CTO Hire Scale 363

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 233

Sales Recruiting Sales Hiring Scale AI 233

SaaStr

JUNE 19, 2025

✨ Lemkin (@jasonlk) June 16, 2025 The Top 3 Reasons AI Sales Tools “Don’t Work” (Spoiler: They Actually Do, If You Use The Tools Properly) I get this question at least 3x a week: “Jason, we tried AI sales tools and they just don’t work. I’ve been in B2B and Saa sales for 15+ years.

Scale 266

Scale AI Sales Hiring Sales 266

SaaStr

DECEMBER 19, 2024

Go Hire That Missing VP! The best way to get out of a hole is to hire a great VP. A great VP of Sales. Well, stop saying you cant hire anyone. And just go finally hire her. But launching a new, more enterprise / more powerful / better edition? Everyone lowered the hiring bar in the Boom. Of Marketing.

Sales Hiring 273

Sales Hiring SaaS Venture Capital Healthcare 273

SaaStr

OCTOBER 20, 2020

Who should you hire, with limited budget? A VP of Sales? A truly great hire is >always< accretive. Hire anyone truly great you can find. And he was proud he’d just hired a VP of Sales at a below-market rate. You don’t want to save money on a great hire. In Just 2 Sales Cycles.

Sales Hiring 341

Sales Hiring Headcount Engineering Banking 341

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 294

Sales Hiring Growth Hacking B2C SMB 294

SaaStr

MAY 10, 2025

A good playbook for customer success is all about driving retention, expansion, and customer happiness while making it scalable: Hire Truly Product-Savvy Customer Success Managers at First Focus on hiring people who customer-focused product nerds to start. Measure time-to-value and/or time-to-go-live. Be careful here.

Sales Hiring 227

Sales Hiring Customer Success Scale Retention 227

SaaStr

DECEMBER 11, 2021

We’ve talked about how all the Second Timers are hiring in customer success way early , ahead of sales, ahead of revenue. To hire in customer success. First, let’s make a rule, a compact, and a commitment: You Must Hire your First Customer Success Manager as a “Single Digit” Hire.

Sales Hiring 286

Sales Hiring Customer Success Headcount Churn 286

SaaStr

JANUARY 9, 2025

Dear SaaStr: What Are Some Successful SaaS Leaders Without Sales Teams? Many that are self-serve and SMB-focused can start off without a sales team … for a while. But almost none stay without a sales team … forever. Yes, Atlassian since well past its IPO had almost no direct sales team. Maybe on Day 0.

Scale 269

Scale Sales Hiring Sales Headcount 269

SaaStr

FEBRUARY 7, 2021

When you go to hire a VP of Sales or even your first sales rep, one of the top qualifying questions I always recommend asking is if they have experience at your deal size, at your ACV (Annual Contact Value). And sales professionals certainly can learn skills and go up (and perhaps even down) a deal size in sales.

SMB 328

SMB Sales Hiring Scale Enterprise 328

SaaStr

DECEMBER 19, 2023

Dear SaaStr: What are the signs that an enterprise SaaS startup is ready to scale by hiring more sales people? For a higher-velocity, in-bound driven SaaS product, most sales reps will have trouble processing more than 50 or so truly qualified leads a month. Before $10m ARR or so, more qualified leads = more sales.

Sales Hiring 294

Sales Hiring Scale Scaling Sales 294

SaaStr

FEBRUARY 7, 2025

His view is your sales team teaches your customers how to get value out of your product. Ron explains: “Wehire mostly technical backgrounds, but as our customers get larger and larger, you start to get global account managers, and they’re going to have much more business strategic account management experience.

Scale 169

Scale Sales Hiring Scaling Revenue 169

SaaStr

APRIL 8, 2025

And thus — hiring more. They they are doubling down and hiring even more to keep these gains going. but close enough) AND they then double their hiring … now they are moving 4x as quickly. If you want to compete in bigger deals, in the enterprise, you probably have to do the same. In a handful of months!

AI 276

AI Sales Hiring Scale B2B 276

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 348

Sales Hiring Sales Recruiting Scale Scaling 348

SaaStr

JULY 11, 2024

How Do You Sift Out the Bitter and Broken Individuals When Hiring? If it’s a role you’ve never hired, find someone great at it and have them do your final interview. For sales, product, or customer success, the best question you could ask is, “What would you do your first couple of weeks?” Don’t hire those people to lead.

Sales Hiring 279

Sales Hiring Scale Marketing Interviewing 279

SaaStr

JUNE 7, 2025

The Deceleration Evidence Ramp’s card spend data reveals several concerning trends that suggest the AI adoption curve is indeed slowing: The growth rate from Q4 2024 to Q1 2025 was significantly lower than previous quarters, even accounting for typical seasonal variations in enterprise spending. ROI scrutiny is intensifying.

AI 275

AI Payment Services Payments Scale 275

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.

Revenue 286

Revenue Scale Sales Hiring Compensation 286

SaaStr

MARCH 20, 2023

Dear SaaStr: How Do You Become Successful at Enterprise Sales? If you haven’t done enterprise sales before, the biggest thing to understand: you can do it. But for enterprise sales, you’re going to have to get your arse out of your home office and go close some real live human beings: Listen — often in person.

Scale 300

Scale Sales Hiring Enterprise Sales 300

SaaStr

MARCH 22, 2022

This requires effort from your entire organization, and Handshake VP, Employer Partnerships Jessica Peluso outlines some changes that you can make to your brand, and your application, interview, and offer process that will help find the talent you are trying to attract and hire. Below is the transcript of Jessica’s session. Hi everyone.

Sales Hiring 258

Sales Hiring Sales Recruiting Scale Sales 258

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 246

Sales Recruiting Sales Hiring Scale Enterprise 246

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. Better to hire for your specific needs and stage. These “five-five” CMOs barely exist.

Sales Hiring 193

Sales Hiring Marketing Technical Review Underperforming Technical Team 193

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 257

Scale Transportation Scaling SMB 257

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 225

Sales Recruiting Scale Sales Hiring B2B 225

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 283

AI Search Artificial Intelligence AI CTO Hire 283

SaaStr

NOVEMBER 27, 2021

Is your CS team growing as fast as your sales team? If this is your first SaaS company, you may not have ever hired or built a Customer Success team. This one isn’t nearly as risky as a VP of Sales , or a VP of Marketing hire. You’ll make a good hire. So hire your first as soon as you can. >>

Sales Hiring 246

Sales Hiring Customer Success Scale Customer Lifetime Value 246

SaaStr

NOVEMBER 27, 2021

Is your CS team growing as fast as your sales team? If this is your first SaaS company, you may not have ever hired or built a Customer Success team. This one isn’t nearly as risky as a VP of Sales , or a VP of Marketing hire. You’ll make a good hire. So hire your first as soon as you can. >>

Sales Hiring 245

Sales Hiring Customer Success Scale Customer Lifetime Value 245

SaaStr

JULY 14, 2024

Hiring and Interviewing Tips: Jason emphasizes the importance of interviewing at least 30 candidates for a role and consulting with an expert in the field to interview the final candidate. Product-Led Growth (PLG) vs. Enterprise Sales: Jason discusses the evolution of PLG, noting that it’s essentially freemium with better analytics.

Sales Hiring 250

Sales Hiring Outsourcing Services Scale Interviewing 250

SaaStr

AUGUST 9, 2021

Selling to enterprise is no easy feat, and it can be a lengthy, complex process. So how do you simplify and speed up your sales cycles? Michael Sindicich, GM of TripActions Liquid, understands what it takes to close big deals and boost enterprise win rates. Read on for Michael’s insightful advice for driving faster sales cycles.

Scale 286

Scale Sales Hiring Enterprise Sales 286

SaaStr

JULY 22, 2020

I’m not ashamed to admit that when I set up our first SaaS sales comp plan, I had no idea what I was doing. In my first start-up, yes I sold to the enterprise. But I did all the sales myself, and stupidly, had no sales comp plan at all ??. SaaS Enterprise Sales Compensation Pl an.

Scale 363

Scale Sales Hiring Sales SaaS 363

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. PLG, enterprise SaaS, marketplaces). The hiring landscape is shifting. It’s a crazy market.

Sales Hiring 95

Sales Hiring Sales Recruiting AI Search Scale 95

Tom Tunguz

JULY 13, 2022

Yesterday, Office Hours welcomed Lars Nilsson, VP Sales Development from Snowflake to talk about his learnings across 5 companies he helped take public. Throughout the hour, Lars provided insightful perspectives on how to build sales organizations. Then, many founders opt to hire an AE. Hire for hunger.

Scale 324

Scale Sales Hiring Development Sales 324

SaaStr

FEBRUARY 5, 2021

Would you still hire them if they hadn't last worked at [insert logo here]? You’ll be very tempted to hire someone with a seemingly magical rolodex. You’ll be very tempted to hire someone with a seemingly magical rolodex. But at $250k a year, those two ringer deals can more than justify the hire. See who does better.

Sales Hiring 328

Sales Hiring Sales Enterprise Pricing 328

Kellblog

JUNE 1, 2025

When a B2B SaaS startup is hiring their first salesperson, I think they should look for someone who: Is a dyed-in-the-wool seller with sales blood coursing through their veins. Their first sales job was in high school and they’ve sold anything from dictionaries to shoes to cars early in their career. Such people exist.

Sales Hiring 60

Sales Hiring Startup Scale Onboarding 60

SaaStr

MARCH 26, 2025

Dear SaaStr: What Skills Do I Have to Learn To Get Good At Enterprise Sales? If you haven’t done enterprise sales yourself before, the biggest thing to understand: you can do it. Many founders who haven’t done sales before want the customers and leads and users to come to them. Really, really hustle.

Scale 146

Scale Sales Hiring Enterprise Sales 146