SaaStr

OCTOBER 18, 2024

You can talk about the roadmap or sales strategy until you’re blue in the face, but if you don’t have the team to do it at scale, there’s no point in talking a ‘big game.’ ” The best sales leaders are the ones that are even better recruiters than the CEO. Nothing else matters, right?

Sales Recruiting 305

Sales Recruiting Sales Hiring Scale AI 305

SaaStr

JUNE 21, 2025

Dear SaaStr: What Should I Know As a First-Time Customer Success Manager? Customers will look to you as the expert, and your ability to guide them will directly impact their satisfaction and retention. Focus on Metrics : Customer Success is all about the numbers. Build Relationships with Customers.

Customer Success 188

Customer Success Management Scale Retention 188

SaaStr

APRIL 6, 2025

A little ways back Databricks VP of Sales Heather Akuiyibo joined SaaStr to share unexpected things that work well at Databricks GTM organization as well as some things that havent worked as well. Deep Dive: Unexpected Learnings Time Management as Competitive Advantage Most sales organizations guess how reps should spend their time.

Scale 195

Scale Sales Hiring Sales Outsourced Development 195

SaaStr

JUNE 24, 2025

We’re living through the biggest transformation in B2B sales since the birth of SaaS itself. The latest from 2025 survey data by ICONIQ from 205 GTM executives across leading B2B SaaS companies The data tells a stark story. This isn’t about sprinkling ChatGPT into your sales process.

Scale 188

Scale AI B2B SaaS 188

SaaStr

FEBRUARY 10, 2025

From Sales-Led to Product-Led: How Apollo.io This analysis examines their journey from a struggling sales-led organization to a successful product-led growth company, resulting in over 880,000 paying customers and substantial revenue growth.

Scale 156

Scale Scaling Outsourced Development Sales 156

SaaStr

JUNE 25, 2025

AI and Cybersecurity: How Rubrik’s Co-Founder Built a $1B+ ARR Platform While Joining the AI Revolution Lessons from Arvind Nithrakashyap, Co-Founder and CTO of Rubrik, on scaling cyber resilience platforms, building multiple product curves, and implementing AI across both products and operations.

Cybersecurity 254

Cybersecurity AI Scale CTO Hire 254

Tom Tunguz

JUNE 20, 2020

This post is part of a series leading up to SaaS Office GTM Edition on June 24 in which we’re reviewing the results of the 2020 Redpoint GTM survey. Today, we’re answering the question: how do teams grow as a startup scales? The median startup with between 1-5M in ARR will have 12 engineers, 6 in sales and 3 in marketing.

Scale 363

Scale Scaling Sales Hiring Software Review 363

SaaStr

AUGUST 5, 2024

How do you leverage your customer success team to drive revenue growth? Hook’s Head of Customer, Natasha Evans, took the stage at SaaStr Europa to discuss the three things leaders should focus on to fuel revenue growth. Historically, customer success teams have been pretty data-poor.

Scale 284

Scale Customer Success Scaling Revenue 284

SaaStr

OCTOBER 22, 2021

The topic of scaling is central to the mission of SaaStr: “Our goal is to help everyone get from $0 to $100m ARR with less stress and more success.” We’ve curated 6 popular SaaStr Annual 2021 sessions from leaders that have navigated the proverbial rocketship to scale: . Video: HE RE. Video: HERE.

Scale 361

Scale Scaling Customer Success Revenue 361

SaaStr

JULY 11, 2025

Sales isn’t going anywhere in the Age of AI. OpenAI has a big sales team, Windsurf does, Anthropic has a great one. Especially the next generation of them: Perplexity has scaled to 5,000 enterprise customers with just 5 sales reps. Cursor built a $400M business with what appears to be a skeleton GTM team.

Scale 179

Scale AI Headcount Sales Hiring 179

SaaStr

DECEMBER 25, 2024

If you are sales-driven, youll usually stall out at $1.5m-$2m in ARR or so if you dont start growing the team to the next level, The First 50. Theres just physics here to get to $10m in ARR in a sales-led model, even a partially sales-led model: After $1.5m Youll need another sales rep at least per every $500k in new ARR.

Sales Hiring 261

Sales Hiring Scale SaaS AI 261

SaaStr

JANUARY 26, 2025

Turn Your Customers Into Your Marketing Engine The second breakthrough was making customer success the core growth engine. A self-reinforcing flywheel where successful customers: Get promoted Tell their network Become champions Drive organic growth 3.

Technical Review 262

Technical Review Payment Solutions Scale Payment Services 262

SaaStr

JANUARY 16, 2025

Workato’s SVP of Embedded Sales and Director of Solutions Marketing joined us at SaaStr Annual to talk about how to nurture customers — a great topic in general, but especially for embedded sales and APIs that can take a while to scale. Customer Success. The Second Most Important SaaS Hire?

Sales Hiring 246

Sales Hiring Scale Sales Churn 246

SaaStr

JULY 11, 2025

How Canva’s CCO Built a $7B Enterprise Motion While Preserving PLG Culture Rob Giglio, Canva’s Chief Customer Officer, shares the playbook for scaling from 170M to 230M monthly active users while building enterprise sales without compromising company culture. Top 5 Takeaways 1.

Scale 169

Scale AI Enterprise Venture Capital 169

SaaStr

APRIL 20, 2025

B2B Startups Spend 15% of Revenue on Sales and 10% on Marketing, Per SaaS Capital #4. Built a Bottom-Up AI SaaS Without a Single Sales Rep #5. The Top 10 Customer Success Metrics Investors Care About in 2025 with Gainsight CEO Nick Mehta #4. The Problem with Small But Mighty AI Start-Ups #2. 100+ Are in B2B. #3.

Scale 141

Scale Customer Success Scaling AI 141

SaaStr

AUGUST 9, 2024

From startup to $500M CARR, Spencer Burke, SVP of Growth at Braze, shares how Braze scaled a growth and customer success team. In this AI moment we’re in, there are still many moments in scaling a company where intuition still matters. Everything customer facing that required product expertise lived under the umbrella.

Scale 291

Scale Sales Hiring Scaling Startup 291

SaaStr

JULY 12, 2025

This creates several advantages: Immediate scalability : No lengthy enterprise sales cycles Usage-based pricing : Revenue scales directly with customer success Lower customer acquisition costs : Developers can start using APIs instantly Key Pricing : Claude Sonnet 4 is priced at $3 per million input tokens and $6 per million output tokens.

B2B 245

B2B Scale Outsourced Development AI 245

SaaStr

MAY 3, 2025

Heres how Id break it down: 0 t o $ 1M ARR: Founder-Led Everything Sales : Founders should lead sales. No VP of Sales yetdont even think about it. Having said that, if you have a steady stream of leads and customers, you really can’t hire a great VP of Demand Gen / Growth too early. More on that here.

Sales Hiring 237

Sales Hiring Part-Time VPE CTO Hire Scale 237

SaaStr

OCTOBER 10, 2023

On a sales front, how do you evolve past founder-led sales, or together with it, so that you can scale your organization? Founder-led sales can be an immense strength and rapidly become a limiting factor. PST, Laura Connell, Partner at Atomico, shares how to scale beyond founder-led sales on your path to Series B.

Scale 277

Scale Sales Hiring Scaling Sales 277

SaaStr

SEPTEMBER 11, 2024

Lucid is the leading provider of visual collaboration software with over 70M users worldwide. Stephanie Couzin, the VP of GTM Strategy and Ops, and Roderick De Greef, the VP of Sales and GM EMEA, share Lucid’s transition from a PLG company to a PLG and Sales-Led company. This is where product-led sales comes in.

Scale 307

Scale Scaling Sales Hiring compliance 307

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. The SMB sales team was incentivized purely on logo acquisition rather than revenue. With only 4% conversion by month two versus a 10% goal.

Revenue 293

Revenue Scale Sales Hiring Compensation 293

SaaStr

OCTOBER 13, 2024

Or didn’t want to do sales. She should hire leaders for Sales, Marketing, Engineering, Product and Customer Success, or at least most of them. But now, I see that if you can hire a great COO as soon as possible after that, you can scale faster. is one of the top ways to help all of us scale faster.

Sales Hiring 260

Sales Hiring CTO Hire Scale Startup 260

SaaStr

MAY 25, 2024

Cloudinary VP of Developer Experience Sanjay Sarathy shares his journey to more than $100M and the lessons he learned along the way for building a PLG motion and an Enterprise sales motion. They didn’t initially envision being a large Enterprise sales organization. Let’s first start with how Cloudinary came to be.

Scale 312

Scale Sales Hiring SaaS Payments Development 312

SaaStr

JUNE 7, 2021

If a sales rep closed a deal, A customer success manager should take it over. An open question around smaller customers is how do you staff up Customer Success for them — if at all. And as startups scale, many try to automate away support and success for the smaller accounts.

Customer Success 353

Customer Success Scale SMB Sales 353

SaaStr

NOVEMBER 13, 2023

How do you scale a product organization quickly? So be sure to use every comment or suggestion that comes from users of your product as stepping stones leading towards perfecting your overall strategy. 5: It’s More Than Just Product When thinking about scaling your product organization, look for three pillars. 1: Ship Fast.

Scale 283

Scale Scaling Sales Hiring Construction 283

SaaStr

FEBRUARY 12, 2025

Meet Wyatt Jenkins: From Construction Sites to Chief Product Officer If you want to understand how vertical SaaS companies scale to $1B+ in revenue while staying true to their customers, there’s no better person to learn from than Wyatt Jenkins, Chief Product Officer at Procore Technologies.

Construction 251

Construction Scale SaaS Travel 251

SaaStr

NOVEMBER 27, 2024

For restaurants, it’s the back end, front end, point of sale, payroll, ERP, and workforce management. Mangomint has one onboarding manager for every two sales reps, but with no contracts and a 30-day free trial, onboarding starts during the trial. Most sales reps hate it. Daniel talks to at least 5-10 customers every week.

SaaS Payments 257

SaaS Payments Payments Payment Solutions Payment Services 257

SaaStr

MAY 27, 2025

So we’ve been proponents of customer success at SaaStr since the earliest days, since our first SaaStr posts in 2012. Especially the power of it leading to second order revenue, from upgrades to referrals to word of mouth and more: CLTV Isn’t The Whole Story. Customers will expect it.

Onboarding 169

Onboarding AI Customer Success Scale 169

Tom Tunguz

FEBRUARY 26, 2025

Most startups play defense when discussing pricing with customers. They dance between asking for too little, leaving money on the table, and asking for too much, only to lose the customer’s interest. The very best companies lead their customers in that dance. Many infrastructure as a service companies do this.

SaaS Payments 283

SaaS Payments Pricing Strategy Scale 283

SaaStr

JUNE 14, 2025

For example, instead of saying, “We’ll hit $10M ARR in two years,” break it down: “We’ll grow from $1M to $3M ARR by expanding our sales team and doubling our lead generation, then scale from $3M to $10M by launching into a new vertical.” What they’re really betting on is you—your ability to execute, adapt, and lead.

Scale 227

Scale Sales Hiring Benchmarks Churn 227

SaaStr

MAY 19, 2022

I remember about 24 months back I asked one of the very best VPs of Sales I know to help me find a VP of Customer Success. This VP of Sales has built legendary teams, and his Directors and Managers have gone on to run many of the top SaaS companies out there. The best VPs of Sales are closers. Or want to, really.

Customer Success 293

Customer Success Scale Sales Hiring Sales 293

SaaStr

FEBRUARY 21, 2025

Key points about SaaStr Annual : Focus on SaaS: Primarily focused on all aspects of SaaS business including sales, marketing, product development, and customer success. Large Audience: Considered the biggest SaaS conference with a large number of attendees from leading SaaS companies, startups, and venture capital firms.

Software 241

Software Scale Venture Capital SaaS 241

SaaStr

MARCH 1, 2024

Dear SaaStr: What’s The Number One Challenge for Scale-Up Stage Founders? You can hack managing and finding 1–3 reps yourself, but after that, you really need a VP of Sales. You will need a VP of Product to scale your roadmap. But you won’t scale past $4m-$5m without a true, seasoned VP of Engineering. As are you.

Scale 274

Scale Part-Time VPE CTO Hire Fractional VPE 274

SaaStr

JULY 12, 2024

Scaling to $150M ARR and beyond is no simple task. Will this change as Grafana Labs scales? But they’re still one of the last remaining open-source companies at scale. Less Than 1% of Grafana Labs’ Users Pay The 6,000 to a million ratio is staggering regarding how much usage there is vs. paid customers. Probably not.

Scale 291

Scale Scaling Sales Hiring Sales Recruiting 291

SaaStr

NOVEMBER 30, 2023

General Partner Doug Pepper and General Partner and Head of Analytics at ICONIQ Growth, Christine Edmonds, share the art and science of scaling GTM at this year’s SaaStr Annual. According to ICONIQ’s data, many successful companies hit a growth plateau at around $15M ARR. Founders are still leading sales and are very good at it.

Scale 274

Scale Sales Hiring Scaling Outsourced Development 274

SaaStr

OCTOBER 13, 2024

ChurnZero: 38% More Customer Success Departments Are Reporting to the CRO. 4 out of 800 Sales Execs Raised Their Hand. How to Build a Product Customers Love and Drive Nearly $1B in Revenue Along the Way with Klaviyo CEO Andrew Bialecki Top Videos and Pods of the Week: #1. The SaaS Era of 2013-2022 is Over. FBOW. | #3.

Scale 292

Scale SaaS Scaling Customer Success 292

SaaStr

JUNE 20, 2025

The Billion-Dollar AI Unicorn Factory The scale of AI startup funding isn’t just impressive — it’s existential for SaaS: The AI Billion-Dollar Club: OpenAI : $8.4 billion valuation after 175M round Scale AI : $29 billion valuation / “sale” with Meta’s $14.3 billion in funding xAI : $6.4

AI Search 289

AI Search Artificial Intelligence AI CTO Hire 289