SaaStr

MAY 20, 2025

Convergent evolution from 2 very different start-ups that now have many similarities at scale. Keys to HubSpot’s Success: The “Hub” Strategy : HubSpot mastered the land-and-expand model, starting with Marketing Hub and strategically expanding to Sales Hub, Service Hub, CMS Hub, Operations Hub, Commerce Hub, and Content Hub.

SMB 279

SMB Scale Education AI 279

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. But SMBs in the middle have become more cost and price-sensitive. #10. It was the only SaaS IPO on 2023. SMB Weaker.

Scale 306

Scale SMB Scaling Enterprise 306

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. There is no substitute for the voice of the customer.

Scale 312

Scale Scaling Sales Hiring compliance 312

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 283

Scale Sales Hiring Scaling Sales 283

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 299

Revenue Scale Sales Hiring Compensation 299

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 255

Construction Scale SaaS Travel 255

SaaStr

MARCH 7, 2025

The right person to lead finance at a Series A company looks very different than the right person to lead finance at a true pre-IPO company (that is near an IPO). And the scope might be even larger at an earlier stage company, but the scope/importance of most of these responsibilities dramatically increase as a company scales.

Scale 319

Scale Finance Headcount Leadership 319

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. Expand pricing and packaging. With experimentation comes pricing and entitlement tests.

Scale 306

Scale Scaling Underperforming Technical Team User Experience 306

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. The category is different.

Scale 120

Scale Entrepreneurship Scaling Underperforming Technical Team 120

SaaStr

NOVEMBER 28, 2024

It’s just hard to get most vertical SaaS start-ups to scale if they can’t get to a $10k ACV. The good news is, you can support these price points effectively with a very efficient inbound sales team, and/or a mix of self-serve and sales-led. At two different price points. To me, $10k is the firewall.

Payment Solutions 264

Payment Solutions Inbound Sales Team Marketing Scale 264

SaaStr

JULY 29, 2022

Jason recently opened up an AMA on Twitter Spaces to answer questions about how to scale faster. And I’ve watched them fairly quickly scale, to soon they’ll be at 10 million in revenue. As they scaled, they radically changed how they did sales. Jason Lemkin: Okay. Let’s get it going. Times are good.

Scale 277

Scale Scaling Sales Hiring Enterprise 277

SaaStr

SEPTEMBER 29, 2023

Naturally, demand is going to lead to a ton of supply. There are advantages beyond higher pricing, with higher pricing being the smallest advantage. Think about the growth curve inflecting more at the top of the funnel with more leads. But when they pulled it open, only 20% of the lift was explained by higher pricing.

Scale 289

Scale Scaling Startup Sales Hiring 289

SaaStr

APRIL 8, 2025

Dear SaaStr: When Should I Hire Our First Sales Person, and Who Should I Hire? "The "The one cheat code to making your first sales hires. Because as a founder, you need to understand the sales process, the objections, and what resonates with your customers. Look for at least 18 months of SaaS sales experience.

Sales Hiring 191

Sales Hiring Scale Sales Pricing 191

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

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 328

Scale Sales Engineering Acquisition 328

SaaStr

DECEMBER 11, 2024

Relying on Self-Serve Sales Structure for Enterprise Not everything needs to be a PLG product. Instead, the winning approach is human-AI collaboration: – Trained professionals assisted by AI tools – Human oversight for complex operations – Quality control for critical outputs Let’s use the sales agent example.

AI Search 290

AI Search AI Artificial Intelligence B2B 290

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 278

Scale Sales Hiring Scaling Revenue 278

SaaStr

FEBRUARY 9, 2021

Few things will frustrate you more in the early days than long sales cycles on bigger deals. You’ll feel like you just don’t have the time for a 6, 9 or even 12 month sales cycle when you’re struggling just to put the first few points on the board. You cannot force 9 month sales cycles into 9 days.

Scale 345

Scale Sales Hiring Sales Pricing 345

SaaStr

NOVEMBER 25, 2022

Scale-ups are exciting. Scaling to satisfy customers’ demands depends on innovation and foresight combined with enterprise-ready technology and the right partners. On top of considerable dedication, creating a scale-up requires a functional edge—a unique and unreplicable capability compared to the players in the industry.

Scale 264

Scale Scaling Marketplace as a Service Entrepreneurship 264

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 287

Outsourcing Services Scale Sales Hiring Outsourced Development 287

SaaStr

APRIL 14, 2025

100+ scale-ups and start-ups showing you how they do it! With 1:1 Meet-a-VC matchmaking and curated sessions, youll have unparalleled access to the capital you need to scale. From seasoned founders to rising stars, every session is handpicked to deliver actionable insights and real-world strategies to help you scale faster.

VP of Engineering 204

VP of Engineering CTO Coach VPCs (Virtual Private Cloud) Scale 204

Sales Hacker

FEBRUARY 7, 2025

SaaS pricing isn’t static – it’s a living strategy that grows with your company. In this article we dive into a playbook for pricing across different stages of company growth, inspired by Geoffrey Moore’s Crossing the Chasm. Tiered pricing models emerge to address these differences.

Pricing 110

Pricing Scale SaaS Technical Review 110

SaaStr

OCTOBER 3, 2022

What is the pricing? Imagine a coverage model, from end to end, for the full customer life cycle: from demand generation to sales to post-sales. Sales Cycle. This includes everything from inside sales to account executives to strategic asset allocation. Post Sales. Execution is not just a sales process.

Scale 277

Scale Sales Hiring Sales Recruiting Scaling 277

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

JANUARY 28, 2025

Bella Liu of Orbee leads a company focused on generative process automation, creating AI solutions that understand and automate complex enterprise workflows. Top-Down vs. Bottom-Up Sales Models Writer and Orby follow a top-down sales model, while Limitless follows a bottom-up sales model, and the effectiveness of each approach is debated.

AI Search 244

AI Search AI Artificial Intelligence Technical Review 244

SaaStr

MAY 10, 2024

At this week’s Workshop Wednesday, Lucas Price, former SVP of Sales at Zipwhip and founder and CEO at Yardstick, shares his insights on how to hire and build a high-performing sales team. During that time, he wasted a lot of money on failed sales hires and decided to learn everything about hiring sellers.

Sales Hiring 245

Sales Hiring Scale Sales Interviewing 245

SaaStr

JULY 31, 2024

In this week’s Workshop Wednesday , SaaStr Founder and CEO Jason Lemkin shares the 7 things the best sales reps get right and the 8 ways the rest make things worse. #1: The best sales reps solve your problems. When you’re doing so well that you’re in order-taking mode, sales reps don’t have to solve a problem.

Scale 290

Scale Sales Pricing ChatGPT 290

SaaStr

NOVEMBER 28, 2022

These two departments are a SaaS company’s most important; without their alignment, there is no growth or scale. We are seeing more agile packaging and pricing methods, dynamic deals, ramp-up revenue, and consumption and usage. One strategy for growth is launching new product lines and expanding the prospects who need your services.

Scale 246

Scale Finance Sales Hiring Scaling 246

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 298

Scale Outsourcing Services Sales Hiring VP of Engineering 298

SaaStr

DECEMBER 15, 2022

So we’ve got all the amazing sessions from 2022 SaaStr Scale up on YouTube here ! “3 Lessons from Building a Marketing Engine to Grow Pipeline from Millions to Billions with Samsara’s CMO” A great session on marketing at scale, across multiple products — with ton of great Q&A at the end. #2.

Scale 242

Scale Scaling Engineering Acquisition 242

SaaStr

OCTOBER 30, 2024

Sales Hub, i.e Sales Hub, Growing Almost Twice as Fast as Marketing Hub HubSpot really has become a CRM company even more than a marketing one. A Per Seat Model is Key to Expansion at HubSpot Long live per-seat pricing! 5 More Interesting Learnings then: #1. Although they are of course highly linked. #3.

SMB 317

SMB CTO Onboarding Scale 317

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 101

Scale Engineering Acquisition Scaling 101

SaaStr

APRIL 7, 2025

and try it here : I did a deep dive live on Workshop Wednesday with my Top 10 Learnings, and brought in Simon Farshid, founder of Assistant UI , which offers the leading platform to add ChatGPT-like interfaces to your own app and to add some color. It’s about doing things at a scale where there’s simply no human alternative.

AI 218

AI B2B ChatGPT Scale 218

SaaStr

FEBRUARY 7, 2021

When you go to hire a VP of Sales or even your first sales rep, one of the top qualifying questions I always recommend asking is if they have experience at your deal size, at your ACV (Annual Contact Value). And sales professionals certainly can learn skills and go up (and perhaps even down) a deal size in sales.

SMB 334

SMB Sales Hiring Scale Enterprise 334

SaaStr

OCTOBER 25, 2021

Q: What billing or pricing tactic have you found in the end just wasn’t worth it? Usually they are a sign of a weak VP of Sales (who can’t close), or founders just trying everything possible (which isn’t all bad). “Regular price increases for SaaS” — Benjamin Irvine. Jason, ed. :

Pricing 325

Pricing Scale Enterprise Onboarding 325

SaaStr

MARCH 25, 2021

The other day, a sales leader working asked me how I got to be “so good at sales.” In fact, that’s why I have so much respect for the art and process of sales. I saw you really could be 2-3x better than me in sales, and make it repeatable, and really scale that way. ” I’m not.

Scale 317

Scale Sales Hiring Sales Pricing 317

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 321

Scale Sales Hiring Sales Marketing 321