SaaStr

JANUARY 2, 2025

Have we lost interest in investing in the human side of sales? Not in hiring sales execs themselves, but in giving them more tools to be more efficient. AI has hardly rendered the sales professional obsolete. Salesforce itself is hiring 2,000 sales execs this year to sell its AI platform, AgentForce.

Sales Hiring 330

Sales Hiring Scale Headcount AI 330

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. So the latest SaaS leader to cross $1B ARR is Klaviyo. It was the only SaaS IPO on 2023. The only one!

Scale 304

Scale SMB Scaling Enterprise 304

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 245

Sales Recruiting Sales Hiring Scale AI 245

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. One challenge Procore faced in expansion was assuming brand awareness.

Scale 287

Scale Construction SaaS AI 287

SaaStr

MARCH 15, 2025

It’s live on SaaStr.com itself and you can also access it here and talk to AI Jason about any of 1000s and 1000s of B2B, sales, SaaS, VC, etc. Here are some of the top ones: “How My VP, Sales Doubled Our Sales in 90 Days. Here are some of the top ones: “How My VP, Sales Doubled Our Sales in 90 Days.

Sales Hiring 259

Sales Hiring AI Scale Compensation 259

SaaStr

OCTOBER 31, 2024

Here’s what I see most often, the Top 6 Mistakes First Time SaaS Founders Make: Incomplete understanding of business model, and how it will scale. You have to hire those extra few reps that we don’t really have leads for today. Basically I only invest in first-timers. You have to pay folks market.

Scale 310

Scale SaaS Social Media Business Model 310

SaaStr

AUGUST 15, 2024

There’s always someone a few years ahead of you on the scaling journey who can share their lessons learned. Robbie O’Connor, the GM EMEA at Notion and the first European hire at Asana and Dropbox takes the stage at SaaStr Europa to talk about the building blocks required to scale GTM teams and operations. Timing is also essential.

Scale 312

Scale Sales Hiring Scaling Innovation 312

SaaStr

OCTOBER 16, 2024

To set the stage, if you talk to any VC out there today, they will tell you that half of their investments which were growing at epic rates in 2021 are barely growing today. 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.

Sales Hiring 320

Sales Hiring Scale AI SaaS 320

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. The takeaway?

Scale 315

Scale Sales Hiring SaaS Payments Development 315

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 294

Scale Sales Hiring Scaling Startup 294

SaaStr

OCTOBER 13, 2024

I try to work with (and invest in) CEOs that are better than me. 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.

Sales Hiring 262

Sales Hiring CTO Hire Scale Startup 262

SaaStr

MARCH 17, 2025

Im investing in fact at SaaStr Fund in a solo founder right now. It could be a VP of Product, Sales, or Engineeringsomeone who takes ownership of a big chunk of the business and cares almost as much as you do. If youre business-focused, hire a strong technical lead. Dear SaaStr: I Have No Co-Founder. What Should I Do?

Sales Hiring 249

Sales Hiring Scale Scaling Engineering 249

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 309

Scale Scaling Strategy Sales Hiring 309

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. There will likely be multiple Toasts for SMBs.

SaaS Payments 259

SaaS Payments Payments Payment Solutions Payment Services 259

SaaStr

JULY 11, 2024

There’s only a small chance that it’ll be an IPO exit, and Stacey Bishop with Scale Ventures shares what it takes to get to that next level of funding. But that shifts over time, and most of your spend goes into sales and marketing. The 3 Other Vital Signs Investors Look For Sales efficiency becomes more important over time.

Scale 303

Scale Scaling Churn Investment 303

SaaStr

NOVEMBER 19, 2024

I see too few SaaS start-up and scale-ups truly segment churn. Finally, use NPS as a leading indicator. But I’d say 90% of SaaS companies I work with and have invested in don’t get these basics right for a long, long time. Because churn is the one thing everyone in the company can impact, on some level. Second, segment churn.

Churn 273

Churn Retention Scale Investment 273

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 287

Scale Customer Success Scaling Revenue 287

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. Bitly had an Enterprise sales-focused team. They also saw a lot of customers shortening links and sharing them on the leading link and bio platforms.

Scale 303

Scale Scaling Underperforming Technical Team User Experience 303

SaaStr

NOVEMBER 28, 2022

Dear SaaStr: What Are Some Signs That Your SaaS Marketing Programs Won’t Scale Well? Most SaaS companies, once they have a mini-brand, start to get some amount of organic, “free” leads. Paid lead services at $100 a lead? Adwords at $5 a click, and $1000 an effective lead? You need to invest there, too.

Scale 276

Scale Scaling Marketing SaaS 276

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 276

Scale Sales Hiring Scaling Outsourced Development 276

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. How selling an investment business is very different from getting VC funding. And that’s substantial scale in. That’s now a billion dollar company.

Scale 109

Scale Entrepreneurship Scaling Underperforming Technical Team 109

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 276

Scale Sales Hiring Scaling Revenue 276

SaaStr

DECEMBER 25, 2021

Here’s the advice they had to offer on scaling your SaaS company. Adam #18: Invest in a strong hiring and onboarding process from day one. In the early days, Zapier invested a lot into all-hands support. It’s hard to re-engineer your business at scale. Instead, understand the strong foundation and then scale from there.

Scale 333

Scale Scaling Innovation Investment 333

SaaStr

APRIL 30, 2024

How do you build GTM efficiency in SMB sales? Ways to scale that don’t include rampant inefficiency and burn. You shouldn’t be adding a bunch of sales reps or spending a bunch of money on marketing if the economics aren’t sustainable. While this title is SMB-oriented, the advice applies to Mid-Market and Enterprise, too.

Scale 304

Scale SMB Sales Hiring Sales 304

SaaStr

SEPTEMBER 29, 2023

Many of you are familiar with this visual, most likely created by an investment firm. 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. And almost all of it was lifted by better conversion rates and more leads. That’s unbelievable!

Scale 287

Scale Scaling Startup Sales Hiring 287

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 327

Scale Sales Engineering Acquisition 327

SaaStr

SEPTEMBER 27, 2024

The reality is you have to find a way for your business to support the kind of investment needed to build an entire outbound team: SDRs, managers, directors, the whole machine. The prospect had posted on LinkedIn that their father had passed, so the AI template said, “Saw your father passed away. Sorry to hear that. That won’t work.

Scale 321

Scale Sales Hiring Revenue Scaling 321

SaaStr

NOVEMBER 28, 2024

I try to look at two things in Vertical SaaS startups, at least when investing : Will everyone in the vertical / industry use it? It’s just hard to get most vertical SaaS start-ups to scale if they can’t get to a $10k ACV. Dear SaaStr: How Big Should The Addressable Market Be to Go into Vertical SaaS?

Payment Solutions 263

Payment Solutions Inbound Sales Team Marketing Scale 263

SaaStr

OCTOBER 25, 2023

For part one of this Ask Me Anything session, Jason covers everything you need to know about hiring your first VP of Sales, what he really thinks about AI, what the future of lead generation in 2024 looks like, and much more. Q: What is the Future of Lead Generation, and How Do You Stand Out? People don’t do that today.

Scale 287

Scale Sales Hiring Sales Recruiting AI 287

SaaStr

JANUARY 23, 2025

You need: Sales leaders who understand complex, multi-stakeholder deals Customer success teams ready for high-touch support Legal expertise for enterprise contract negotiation Product leaders who can balance current needs with future vision Pro tip: Hire enterprise reps in pairs. If both succeed, you’re ready to scale.

Enterprise 244

Enterprise Sales Hiring Scale Outsourced Development 244

SaaStr

JULY 15, 2022

Jason recently opened up an AMA on Twitter Spaces to answer questions about scaling from $1M to $10M. We did a good AMA on this scaling at SaaStr Europa in Barcelona, a couple weeks back. That will scale, and then take those emails after four great pieces of content and do a weekly webinar and do a weekly get-together for them.

Scale 296

Scale Outsourcing Services Sales Hiring VP of Engineering 296

SaaStr

FEBRUARY 1, 2024

As companies scale, they evolve, so how should marketing evolve accordingly to add maximum value? PST, Kady shares the ten things that change in marketing as you scale. PST, Kady shares the ten things that change in marketing as you scale. The reality is that a lot of things change as we scale. The answer isn’t simple.

Scale 277

Scale Scaling Sales Hiring Marketing 277

Sales Hacker

DECEMBER 17, 2024

Building ‘opinionated products’ and the importance of customer intimacy Lessons learned from scaling Twitter’s ad business from zero to $650 million in three years. 15:41) Scaling Twitter’s ad business and managing hyper-growth. (26:54) Plus, an analysis of the top 75 trending sales AI tools.

Scale 102

Scale Engineering Acquisition Scaling 102

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. Learn your prospects’ business processes in detail, and how your product enhances them.

Scale 309

Scale Sales Hiring Enterprise Sales 309

SaaStr

DECEMBER 16, 2022

How do you enter a highly competitive marketplace, carve a niche for yourself, and then scale the business to $100 million+ ARR? Sam Blond, Partner at Founders Fund, joined Matt Plank, VP of Sales at Rippling, to unlock the secrets to exponential revenue growth. Scaling your go-to-market efforts.

Outsourcing Services 285

Outsourcing Services Scale Sales Hiring Outsourced Development 285

SaaStr

MARCH 28, 2025

Treat this like a sales pipelinetrack leads, co-selling efforts, and revenue generated from these partnership. This data will be critical when scaling your program. Shopifys partner revenue grew from 8% in 2018 to 20% by 2020, but it took years of investment to get there . Its not a quick win. Do lots of them.

Scale 147

Scale Sales Hiring SMB Enterprise 147