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 293

Revenue Scale Sales Hiring Compensation 293

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

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. The Second Most Important SaaS Hire? Customer Success. But the results?

Sales Hiring 246

Sales Hiring Scale Sales Churn 246

SaaStr

JANUARY 3, 2025

Or a great growth marketer paired with a great sales team will punch above their weight class. HubSpot recently changed its interview process to try and help maximize tenure and employee retention at the executive level. In sales, t he more SMB you are, the more you should lean on your bench. It can make all the difference.

Sales Hiring 284

Sales Hiring Scale Systems Review Interviewing 284

Tom Tunguz

FEBRUARY 26, 2025

The very best companies lead their customers in that dance. Many mid-market software companies price with the goal of revenue maximization, negotiating for the highest possible price in each sale. Penetration pricing leads to land-and-expand sales tactics. Most startups play defense when discussing pricing with customers.

SaaS Payments 283

SaaS Payments Pricing Strategy Scale 283

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. The 5 Key Elements of Codeium’s GTM Scaling Playbook 1. What is Codeium and Windsurf?

Sales Recruiting 237

Sales Recruiting Sales Hiring Scale AI 237

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. You don’t have to leave as the organization scales. This isn’t new.

Scale 291

Scale Sales Hiring Scaling Startup 291

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. Focus on Net Retention Net retention is the ultimate metric for customer success.

Sales Hiring 232

Sales Hiring Customer Success Scale Retention 232

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. Upsell and retention is an art, science and craft. She can be your CTO forever.

Scale 274

Scale Part-Time VPE CTO Hire Fractional VPE 274

SaaStr

AUGUST 5, 2024

When you find the answer to these questions, you can expand an existing customer base and create cool data-driven case studies to help your sales team bring in net business. 1: Build a Value Narrative Value narratives have been around for some time in pre-sales motions. Often, that doesn’t feed through to post-sales.

Scale 284

Scale Customer Success Scaling Revenue 284

SaaStr

FEBRUARY 7, 2025

Speaker Bio Jason Lyman leads marketing at Customer.io, where he’s helped scale the platform to power over 35 billion customer interactions for 7,000+ high-growth companies. Before Customer.io, Jason built and scaled marketing teams at several B2B SaaS companies, with a focus on customer engagement and revenue operations. .

Scale 271

Scale SaaS B2B Scaling 271

SaaStr

MAY 5, 2025

The New Rules of SaaS Growth: Whats Next for AI, PLG, and Revenue Scale with HubSpots CEO 2. From Startup to $10B+: Lessons on Scaling, AI, and the Future of SaaS with Dropboxs Founder and CEO 3. How to Build Top-Performing Sales Orgs: OpenAI, Slack, Webflow + more 7. How to Build a Category-Leading Product: Owns CEO 12.

Scale 172

Scale New CTO CTO AI 172

SaaStr

DECEMBER 15, 2021

SaaStr Scale 2021 is starting soon. 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. 8:00 AM (50 MIN) – The Secrets to Building Your Marketing Engine To Drive Scale with Airtable CMO Archana Agrawal. LIVE TODAY!

Scale 273

Scale VP of Engineering Scaling SMB 273

SaaStr

MAY 28, 2025

Building a commission plan for Account Managers (AMs) is a bit different than for AEs (Account Executives) because AMs are typically focused on retention, expansion, and upsells rather than net-new sales. The variable portion should be tied to measurable outcomes like net retention, upsell revenue, and customer satisfaction.

Scale 196

Scale Management Churn Finance 196

FastSpring

JANUARY 23, 2025

Listen for the full insights into: How Flippa.com works to connect for-sale businesses with buyers while managing the complexities of valuation and seller expectations. When I was running it, it was a lot smaller than that, but scaled that up very, very quickly. And that’s substantial scale in.

Scale 121

Scale Entrepreneurship Scaling Underperforming Technical Team 121

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 243

Software Scale Venture Capital SaaS 243

SaaStr

APRIL 5, 2022

Q: Dear SaaStr: What are Some Common Decisions SaaS Startups Make that Hurt Their Ability to Scale? The problem here is that instead of hiring an accretive resource, you hire a cost center than can’t deliver sales/leads/upsells. Hire someone above your team members that can’t scale as soon as they stop scaling.

Scale 261

Scale Sales Hiring Scaling Startup 261

SaaStr

JANUARY 23, 2025

Just look at the numbers: Enterprise customers bring 95%+ best-in-class retention vs. 85% in mid-market. If both succeed, you’re ready to scale. Master the Multi-Stakeholder Sale Enterprise deals aren’t won in a single meeting. That compounds dramatically over time.

Enterprise 244

Enterprise Sales Hiring Scale Outsourced Development 244

Clouded Judgement

MARCH 28, 2025

Starting and scaling a software company was really hard. Starting and scaling a software company was really hard. If you wanted to scale users and growth, you needed to scale a physical data infrastructure footprint. ” This used to be how companies scaled! It wasn’t very elastic. What does this mean?

Cloud 299

Cloud AI Scale Scaling 299

SaaStr

MAY 31, 2025

Early Growth Stage ($1M-$10M ARR) At this stage, you’re starting to scale, and the risk is lower. Scaling Stage ($10M-$50M ARR) By now, you’re hiring people who want the machine running already. For example, a VP of Sales driving ARR growth might get closer to 1%, while a VP of HR might be closer to 0.3%.

Part-Time VPE 205

Part-Time VPE Sales Hiring Sales Recruiting Compensation 205

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. Because founder-led sales worked really well for most of the early stages, but you eventually start running out of juice around $15M ARR.

Scale 274

Scale Sales Hiring Scaling Outsourced Development 274

SaaStr

SEPTEMBER 29, 2023

Naturally, demand is going to lead to a ton of supply. Think about the growth curve inflecting more at the top of the funnel with more leads. The second product had better retention. And almost all of it was lifted by better conversion rates and more leads. This question exists whether you have 2, 12, or 50 sales reps.

Scale 284

Scale Scaling Startup Sales Hiring 284

SaaStr

APRIL 30, 2025

ServiceTitan, the operating system for the trades, continues to scale impressively, with $772M in FY25 revenue, $800m+ ARR and a clear path to $1B ARR. Net Dollar Retention >110% and GDR of >95%: The Power of Being a True Operating System ServiceTitans NRR consistently exceeds 110%, even with SMB-heavy customers. Thats rare.

Payments 144

Payments Payment Services SaaS Payments Payment Solutions 144

SaaStr

JANUARY 16, 2023

To convert an idea into a successful venture, startups need to be equipped to scale. Mike Wiacek, CEO at Stairwell, Mo Jebrini, CTO at Mashvisor, and Michael Ermolenko, CTO at Inworld.ai, discuss with Helene Ambiana, Global SMB and Startups Marketing Director at Google Cloud, how they overcame the hurdles of scaling and reached their goals.

Scale 259

Scale CTO Hire Cloud Scaling 259

SaaStr

AUGUST 18, 2024

Massimo Arrigoni, CEO of Beefree, and Enrica Lipari, the People and Culture Director of Beefree’s parent company, Growens, share 5 secrets to a high employee retention rate. When you default to transparency, it leads to awareness, awareness leads to alignment, and alignment leads to better-performing teams.

Retention 312

Retention Scale Company Culture Leadership 312

SaaStr

MAY 28, 2025

Their sales and marketing expenses as a percentage of revenue dropped from 113% in FY-20 to just 51% in FY-24. NRR and Expansion Revenue Remains Strong at 112% With a net dollar retention rate of 112% overall and 117% for $100k+ customers, Monday.com continues to demonstrate strong expansion within existing accounts.

Scale 184

Scale SMB Acquisition Enterprise 184

SaaStr

APRIL 14, 2020

Or at least by splitting up sales-driven and self-service revenue. And setting different goals for sales and retention for each segment: Growing. Most of you that I talk to haven’t fully finished segmented their prospects and existing customer base this way. But allow material relaxation of account retention.

Scale 321

Scale Sales Healthcare Retention 321

SaaStr

JUNE 14, 2023

Ten years ago, no one would have guessed Europe would generate the largest software IPO globally, yet UiPath has done it, and net retention is 144%. At SaaStr Europa, UiPath’s Dines shared five insights from growing a company from nothing, so other founders can learn what it takes to scale a SaaS startup to $1B+ ARR.

Scale 246

Scale Artificial Intelligence Technical Review Software Review 246

SaaStr

JANUARY 21, 2022

You might feel confused about where to begin, how to scale up, which mistakes you should avoid, and things you should consider before expanding. Now, let’s look at ten learnings that Dorian gathered while scaling Grammarly from a Consumer to an Enterprise brand with B2B offerings. Enter your email below for the latest SaaStr updates.

Scale 246

Scale SMB Enterprise Sales Hiring 246

SaaStr

JUNE 7, 2023

Scaling a tech startup doesn’t come easy, and when you’ve tried all the conventional SaaS advice, it might be tempting to give up. But before the years of rapid scaling, it took the company a little while to hit its stride. What Did WorkRamp Do Differently to Scale? In one year, WorkRamp improved gross retention by 11%.

Scale 246

Scale Scaling SMB Marketing 246

SaaStr

APRIL 20, 2022

This famous quote from self-help author Robert Collier applies to every sales organization because excellent results come through repeatable activities, not one-off wins. Alice Katwan , SVP at Twilio , discusses how you can build a high-retention sales team while being remote. Implement systems to attract great talent.

Sales Hiring 272

Sales Hiring Scale Retention Sales 272

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.

Scale 317

Scale Sales Hiring Sales Marketing 317

SaaStr

JUNE 7, 2021

If a sales rep closed a deal, A customer success manager should take it over. And as startups scale, many try to automate away support and success for the smaller accounts. I’d suggest a few basic thoughts and rules: If you have sales involved, then you need customer success, too. Set clear KPIs on NRR and retention.

Customer Success 353

Customer Success Scale SMB Sales 353

SaaStr

DECEMBER 14, 2022

Yamini Rangan, CEO at HubSpot, has many insights on how to serve SMB customers at scale. But because SMBs are rarely digital-first, their recent challenges allowed HubSpot to leverage their years of experience in marketing automation, as it became a core feature of how these companies worked to scale. HubSpot for Startups” program.

Scale 261

Scale SMB Scaling Innovation 261

SaaStr

MAY 27, 2025

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. Customer Success has in many cases turned into a weaponized arm of sales, and has stopped being the champion of the customer. Especially as AI takes over more and more of the sales process.

AI 176

AI Onboarding Customer Success Scale 176

SaaStr

MARCH 9, 2025

Jess Clark, Head of User Experience at Calendly Jess leads Calendly’s user experience initiatives, working closely with Steven to create intuitive scheduling experiences that help people connect more efficiently and achieve their desired outcomes. His background combines deep product strategy with practical AI implementation experience.

AI 198

AI Scale Education User Experience 198

SaaStr

FEBRUARY 24, 2023

They initially double their ARR each year in scaling post $10M. Their net dollar retention (NDR) is consistently above 120% post $10M ARR. The revenue per FTE surpasses the spending around the $100M mark in ARR, and the trend continues to IPO where revenue growth doesn’t lead to an inflation of per-employee spend.

Scale 246

Scale Sales Hiring Scaling Venture Capital 246