SaaStr

DECEMBER 20, 2024

Former Head of Revenue at BILL and HubSpot Americas leader Michelle Benfer recently joined us on a SaaStr Workshop Wednesday share her insights on one of the most critical roles in any SaaS organization: the frontline sales manager. “At HubSpot, I had over 100 frontline sales managers reporting to me.

Sales Hiring 257

Sales Hiring Scale Underperforming Technical Team Sales 257

SaaStr

NOVEMBER 13, 2024

Klaviyo dominates marketing in the Shopify ecosystem and in ecommerce, and just keeps on scaling. But it’s clear that it’s still in the investing phase, and increasing spend in sales & marketing. New Startups and Companies and Enterprise Strong. So the latest SaaS leader to cross $1B ARR is Klaviyo. SMB Weaker.

Scale 294

Scale SMB Scaling Enterprise 294

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

MARCH 13, 2025

” It was the gold standard for B2B software companies scaling from $1M to $100M ARR. A deep dive with two leaders at the forefront of AI startup scaling and investment. Previously leading growth at Cohere and Heroku, he’s been instrumental in scaling multiple category-defining companies in the AI space.

AI 268

AI Scale Artificial Intelligence Startup 268

SaaStr

FEBRUARY 14, 2025

What does it take to build and scale a vertical SaaS giant over two decades? In a recent conversation with SaaStr CEO and Founder Jason Lemkin, Tooey shared insights into his 23-year journey as CEO of Procore , the leading SaaS platform for construction management. That pivot paid off. The era of point solutions is over, Tooey states.

Scale 278

Scale Construction SaaS AI 278

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 159

Scale Scaling Outsourced Development Sales 159

SaaStr

DECEMBER 4, 2024

These outcomes might include: Driving user growth Maximizing revenue Ensuring user satisfaction Scaling adoption A different outcome would lead to a different pricing choice. Growth stage: Introduced business plans with 20-user minimums to provide enterprise-grade features.

Payments 278

Payments Pricing Scale Revenue 278

SaaStr

FEBRUARY 8, 2025

The Hidden Math Behind CS Evolution Perhaps the most fascinating revelation from the panel was how CS needs to transform at different revenue scales. The entire success organization aligned around a single north star: proving so much value that growth became inevitable. Forget everything you know about SMB customer success.

Customer Success 263

Customer Success Scale Government Systems Review 263

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 236

Sales Recruiting Sales Hiring Scale AI 236

SaaStr

DECEMBER 26, 2024

That ties to our overall rough sales cycle data here: Dear SaaStr: What’s a Good Benchmark for B2B Sales Cycles? And a few other data from the report: Gongs enterprise customers see about a 25% win rate, conversion from Opportunity to Closed. Thats a bit higher than I expected.

Scale 278

Scale Benchmarks B2B Enterprise 278

SaaStr

OCTOBER 16, 2024

It’s been around for decades but has continued to iterate, expanding into the enterprise, the contact center, and so much more. Even With a Big Enterprise Push for Years, 60% of Revenue Still From Mid-Market and SMB RingCentral closed 20 $1M+ TCV deals last quarter. A reminder to not stay too reliant on direct sales as you scale.

Scale 278

Scale SMB Compensation Cloud 278

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 273

SaaS Payments Pricing Strategy Scale 273

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

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. Building a $100M+ ARR business is no easy feat.

Scale 306

Scale Sales Hiring SaaS Payments Development 306

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 271

Scale Sales Hiring Scaling Sales 271

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. Many founders want the customers and leads and users to come to them. Your product will always be deficient in some fashion in the enterprise.

Scale 300

Scale Sales Hiring Enterprise Sales 300

SaaStr

DECEMBER 19, 2023

Dear SaaStr: What are the signs that an enterprise SaaS startup is ready to scale by hiring more sales people? In the early days, it’s simply that you have a few more leads than you can currently handle. Plus — following up on the 50 qualified leads from the month before. To a point. appeared first on SaaStr.

Sales Hiring 294

Sales Hiring Scale Scaling Sales 294

SaaStr

JANUARY 24, 2025

One thing is clear is the team that send this isnt the A or B sales team. Which makes sense, since Salesforce is mainly hunting big enterprise deals. And a great example of running a very successful outbound program at scale here: And what I’d do better. Its being sent by the C team. This much is clear.

Scale 278

Scale Sales AI Enterprise 278

SaaStr

FEBRUARY 6, 2025

Thread AI’s founder and Palantir alum Maya Gonimah has cracked the code on enterprise AI implementation through their strategic partnership with Google Cloud. Darren Mowrey (Google Cloud) Darren leads strategic partnerships at Google Cloud, focusing on helping startups scale their AI implementations.

AI 184

AI Cloud Enterprise Technical Review 184

SaaStr

APRIL 8, 2025

Many of the early break out leaders in AI for B2B and otherwise have been “small but mighty teams” Honestly we’d all love it if that scaled. The Second “Problem” With Small But Mighty AI Teams … Is Enterprise Sales A tiny team can be fairly efficient with a 100% self-serve and PLG motion.

AI 276

AI Sales Hiring Scale B2B 276

SaaStr

OCTOBER 16, 2024

AI has ripped through categories like the post-sales space and customer support centers. Salesforce is doing it, Zendesk and Intercom are all doing it at scale. You see this first point viscerally if you’re involved in post-sales or support. Sales is beginning to promise this. 2: The product has to be better for it.

Sales Hiring 312

Sales Hiring Scale AI SaaS 312

SaaStr

DECEMBER 22, 2024

The Future of AI, Open Source and Enterprise SaaS with Databrick’s Founder CEO Ali Ghodsi: #2. “Lessons Learned in Scaling Databricks, AWS, VMWare and More” with Databrick’s SVP and GM Ed Lenta #3. The Top 5 Lessons Learned Scaling Databricks’ to $1.5B ARR with VP Product Nadim Hossain #5.

Scale 269

Scale AWS Leadership AI 269

SaaStr

DECEMBER 22, 2023

At the SaaStr Annual, Kiren Sekar, Samsara’s Chief Strategy Officer and founding chief Product Officer shared five lessons he learned along the way from scaling six products to $100M+. Lesson 1 — The Magic “Scale or Pivot” Metric With so many different SaaS metrics out there, which metric can really steer a business?

Scale 300

Scale Scaling Strategy Sales Hiring 300

SaaStr

JULY 12, 2024

Scaling to $150M ARR and beyond is no simple task. Will this change as Grafana Labs scales? Grafana Labs still has features and capabilities they hold back that appeal to large enterprises, such as things around security and compliance. But they’re still one of the last remaining open-source companies at scale.

Scale 284

Scale Scaling Sales Hiring Sales Recruiting 284

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 248

Construction Scale SaaS Travel 248

SaaStr

APRIL 2, 2025

Today it’s at: $800m ARR Growing 22% 20% Free Cash Flow Margins Modest re-acceleration in revenue growth and new customer count — but not NRR Roots are SMB, but 60% of ARR comes from mid-market and enterprise today And a $4B market cap, so 5x ARR Freshworks is getting a bit of a second wind, which is great to see!

Scale 257

Scale AI SMB B2B 257

SaaStr

NOVEMBER 27, 2024

For restaurants, it’s the back end, front end, point of sale, payroll, ERP, and workforce management. How to Make Onboarding Work for SMBs While in some cases, selling to SMBs is easier than Enterprise in many ways, one way in which it’s fundamentally harder is onboarding. Most sales reps hate it.

SaaS Payments 254

SaaS Payments Payments Payment Solutions Payment Services 254

SaaStr

JULY 30, 2024

Okta’s VP of Engineering, Monica Bajaj, and Senior Director of Platform Product Marketing, Priya Ramamurthi, share Okta’s playbook to PLG, developer experience, and Enterprise ARR. Product-led outperformers generate ten percentage points higher in ARR and 50% higher in valuations than sales-led growth outperformers.

Underperforming Technical Team 276

Underperforming Technical Team Enterprise Scale Payments 276

SaaStr

FEBRUARY 21, 2025

Offers workshops, networking, and investor matchmaking for startups and enterprises. Key points about SaaStr Annual : Focus on SaaS: Primarily focused on all aspects of SaaS business including sales, marketing, product development, and customer success. Held annually in the San Francisco Bay Area (usually in September).

Software 240

Software Scale Venture Capital SaaS 240

SaaStr

NOVEMBER 13, 2023

How do you scale a product organization quickly? years, has seen massive growth and over 14 different frameworks, trust center capabilities, Enterprise risk management capabilities, audit capabilities, work center capabilities, over 100 plus integrations, and 350 different features. #1: 1: Ship Fast. 1: Ship Fast. Iterate Faster.

Scale 277

Scale Scaling Sales Hiring Construction 277

SaaStr

JUNE 19, 2024

Bitly CEO Toby Gabriner and CPO Kelsey Stevenson share the three secret ingredients that helped them when scaling to $100M ARR and what they could have done differently. Around 2012, the focus became solely on the Enterprise, which is interesting considering they had a full-blown PLG engine. Bitly had an Enterprise sales-focused team.

Scale 294

Scale Scaling Underperforming Technical Team User Experience 294

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 269

Scale Part-Time VPE CTO Hire Fractional VPE 269

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. What should you look for in an Enterprise rep vs. a Mid-Market rep?

Scale 268

Scale Sales Hiring Scaling Revenue 268

SaaStr

JANUARY 28, 2025

Cutting Through the Noise: Three Gen AI Pioneers Reshaping Enterprise Technology In a pivotal moment for generative AI, Vanessa Larco, partner at NEA, brought together three visionary CEOs convened at SaaStr Annual to share insights that are redefining the technological landscape.

AI Search 244

AI Search AI Artificial Intelligence Technical Review 244

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 269

Scale Sales Hiring Scaling Outsourced Development 269

SaaStr

SEPTEMBER 17, 2024

So two of the great leaders in SMB SaaS, Shopify for e-commerce, and HubSpot for sales, marketing and more, are going more upmarket: HubSpot 100+ seat deals are up 55% Shopify now gets 31% of its revenue from “Plus” or its bigger brands and more enterprise product And yet … they are also both going more SMB as well!

SMB 316

SMB Enterprise Scale Scaling 316

SaaStr

JULY 5, 2022

By moving from Freemium to “Contact Me” only (albeit with transparent pricing), sales went way, way up. He got into conversations with top prospects, and got them to buy bigger, better editions. So many sales leaders get frustrated with Free editions, very low-cost editions … and the Long Tail in general.

Scale 321

Scale Sales Engineering Acquisition 321