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 234

Sales Hiring Part-Time VPE CTO Hire Scale 234

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

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

NOVEMBER 22, 2020

Prashanth Chandrasekar, CEO @ Stack Overflow recently shared with our community the four key pillars he feels are necessary to propel a company to scale upward. Is your product sound, and does it solve a big problem for customers, enough for you to scale? Deliver repeatable value early in the customer’s journey.

Scale 322

Scale Scaling Technical Review Systems Review 322

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 290

Scale Sales Hiring Scaling Startup 290

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 140

Scale Customer Success Scaling AI 140

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

JUNE 22, 2021

This is a positive trajectory, but it presents a challenge for your customer success efforts: How can you scale your support and CS while still delivering a memorable, quality customer experience? Latest Customer Learnings From New Research. Today’s Critical Challenges For Customer Success .

Scale 277

Scale Customer Success Scaling Compensation 277

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.

AI 166

AI Onboarding Customer Success Scale 166

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

FEBRUARY 15, 2022

E.g., Sales +Marketing Expenses < First Year ACV = Success ? But maybe not while you are scaling, you can often afford to invest more if you have funding. One you may not have heard but it’s a good one — is Hire One Customer Success Manager for every $2m in ARR.

Scale 261

Scale Customer Success Sales Hiring Scaling 261

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

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

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 250

Construction Scale SaaS Travel 250

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

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

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

DECEMBER 15, 2021

SaaStr Scale 2021 is starting soon. 7:00 AM (50 MINS) – Acquiring SMB 10,000 Customers Solely from Data with Gorgias’ CEO Romain Lapeyre. 7:00 AM (40 MINS) – Product-led Growth: How to Execute Across the Full Funnel (and Mistakes We Made) with Reprise’s VP of Marketing and VP of Sales. LIVE TODAY!

Scale 273

Scale VP of Engineering Scaling SMB 273

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 240

Software Scale Venture Capital SaaS 240

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

DECEMBER 1, 2021

With two weeks left to go until SaaStr Scale 2021, we’re looking at an incredible speaker line-up this year. Tickets to Scale are free, so be sure to sign up to join us live on December 15th! SaaStr Scale is dedicated to bringing you the playbooks for scaling to $100M and beyond. Mark Wayland, CRO @ Box.

Scale 278

Scale Scaling SMB compliance 278

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

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. With scale, though, these priorities can change.

Scale 246

Scale Sales Hiring Scaling Sales 246

SaaStr

JANUARY 24, 2024

Mark Roberge , SaaStr fan-favorite and Co-Founder and Managing Director of Stage 2 Capital brought together some of the top CROs in SaaS during the SaaStr Annual to share some of their greatest learnings and pivotal moments leading some of the Cloud 100 SaaS companies. From a GTM execution standpoint, they weren’t focused.

Scale 273

Scale Sales Hiring Scaling Revenue 273

SaaStr

DECEMBER 30, 2023

I’ve talked with three CEOs at leading vendors in sales and post-sales at $200m+ in ARR the past few weeks and they’ve all reinforced these are some of the biggest changes in a generation. What we’ve seen in the first 15 years of SaaS: Specialization in sales. Segment reps, and have closers close.

Customer Success 339

Customer Success Scale AI Technology 339

SaaStr

JANUARY 5, 2022

At Box, there was a culture and mindset shift early on that customer-facing teams shouldn’t live in silos. Every customer-facing team is on the renewals team: customer success, sales, product, customer support, marketing, and of course, renewals. When it comes to your sales team, productivity is paramount.

Scale 301

Scale Scaling Sales Hiring Software Review 301

SaaStr

AUGUST 2, 2021

This early phase is where you’re still looking for that perfect product-market fit and scaling the product to market. Also, they had a direct sales team mainly selling to enterprises in a top-down sales motion. “[The The focus also widens to executing an outstanding GTM strategy and build top-notch customer success.

Outsourcing Services 284

Outsourcing Services Scale Scaling Outsourced Development 284

SaaStr

FEBRUARY 7, 2025

At SaaStr AI Day 2025, Jim Palmer, Dialpad’s Chief AI Officer (and co-founder of TalkIQ, which Dialpad acquired), shared the tactical playbook they used to build and scale their AI capabilities. Here are the key learnings every SaaS company should know. Make this decision early.

AI 251

AI Scale Government compliance 251

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. But I did all the sales myself, and stupidly, had no sales comp plan at all ??. Then, as we first scaled up a sales team, we ended up literally copying Salesforce’s comp plan.

Scale 363

Scale Sales Hiring Sales SaaS 363

SaaStr

JUNE 27, 2020

A little while back we put together some of the top sales & marketing mistakes SaaS companies and founders make, especially in the early days. Sales: Hiring any reps you wouldn’t buy from yourself. Later, once you have a strong VP of Sales, it’s fine though. Your sales reps need to eat. Maybe OK for customer success.

Sales Hiring 363

Sales Hiring Scale Startup Marketing 363