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 300

Revenue Scale Sales Hiring Compensation 300

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? Measure leading indicators and not lagging indicators like churn.

Scale 326

Scale Scaling Technical Review Systems Review 326

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. HubSpot has gone upmarket over the past years, while also remaining even more SMB-focused. 5 More Interesting Learnings then: #1. Although they are of course highly linked. #3.

SMB 317

SMB CTO Onboarding Scale 317

SaaStr

SEPTEMBER 19, 2023

based SMB sales positions. SaaS sales execs with even a little bit of experience at other SaaS companies are looking for higher and higher OTEs, often with lower effective attainment and high support costs. based sales reps often aren’t really willing to work, or excel, at sub-$100k OTEs anymore. customers?

SMB 318

SMB Scale Sales Hiring Sales 318

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 325

SMB Enterprise Scale Scaling 325

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

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 277

Scale AI SMB B2B 277

SaaStr

APRIL 4, 2022

The ultimate success of demand generation is defined as the number of marketing qualified leads (MQL) generated, and is measured by impressions, website visits, and clicks. . But this narrow approach limits our ability to understand how to create a solid pipeline and inhibits us from understanding the end-to-end prospect journey.

Scale 279

Scale Revenue Scaling Marketing 279

SaaStr

DECEMBER 14, 2022

Yamini Rangan, CEO at HubSpot, has many insights on how to serve SMB customers at scale. The Challenge of Digital Expansion for SMB. When the shift began in 2020, everyone wrote off SMBs as unprepared for the necessary changes that lie ahead. HubSpot only made direct and partner sales for the first eight or nine years.

Scale 265

Scale SMB Scaling Innovation 265

SaaStr

NOVEMBER 27, 2024

Full-Stack SaaS for SMBs Toast today is worth $14B at $1.5B There will likely be multiple Toasts for SMBs. For restaurants, it’s the back end, front end, point of sale, payroll, ERP, and workforce management. Most sales reps hate it. When you build a high-velocity sales motion, you must find systems to scale it.

SaaS Payments 261

SaaS Payments Payments Payment Solutions Payment Services 261

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 279

Scale VP of Engineering Scaling SMB 279

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

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

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 312

Scale Scaling Strategy Sales Hiring 312

SaaStr

JANUARY 7, 2021

Zendesk’s Sharon Prosser, VP Worldwide SMB Sales & XDR, and Astha Malik, VP GTM Strategy, Planning, and Enablement share some guiding principles about how their company has grown and enriched many markets. Move your sales teams into different areas of focus and get them to need each other. The X-Factors. 3 Invest in people.

Scale 284

Scale Scaling Sales Hiring SMB 284

SaaStr

MARCH 3, 2023

At SaaStr APAC 2023, Scott Pugh, VP of Sales at Figma, shared how to scale these two sales teams while building culture. Pugh’s strategy is simple, albeit not always easy: Recruitment — how to hire the best talent to scale your sales organization. Diversity is really important when scaling.

Scale 279

Scale Sales Recruiting Sales Hiring Scaling 279

SaaStr

JULY 26, 2022

So in theory, SMB SaaS is better than enterprise, at least 9 times out of 10: Deals close much faster. Don’t need as much sales experience on sales team. SMBs often force you to build a better product, as they lack a deployment and IT team. SMBs go out of business, and quickly. Endemic churn.

SMB 363

SMB Churn Payment Services SaaS 363

SaaStr

FEBRUARY 20, 2022

Check out this week’s top blog posts, podcasts, and videos: Top Blog Posts This Week: Your Sales Efficiency Will Probably Plummet Toward $10m ARR. 30+ SaaS CEOs Share The Signs Their First VP of Sales … Just Wasn’t Going to Work Out. Dear SaaStr: Should We Pay Our Sales Reps on Renewals? Plan For It.

SMB 290

SMB Scale Marketing Sales 290

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

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 285

Scale Scaling SMB compliance 285

SaaStr

FEBRUARY 5, 2025

And when it IPO’d, it was still solidly an SMB solution. Spending on sales & marketing is down. Leaning More into Free Even as it goes more enterprise, and see a decline in SMB / Commercial accounts, PagerDuty is still leaning in more on Free. We all used some sort of tool for website monitoring, but the O.G.

SMB 282

SMB B2B Enterprise Scale 282

SaaStr

NOVEMBER 6, 2021

The other day Brendon Cassidy, the first head of sales at LinkedIn and the first VP of Sales at $10B Talkdesk, Adobe Sign / EchoSign, and more — and now co-CEO of Cosell — and I caught on what’s changing in the Sales Playbook for 2022. Even in SMB and mid-market. Well in most cases.

Scale 342

Scale Sales Hiring Sales SMB 342

SaaStr

APRIL 1, 2023

How To Capture This Global SMBTech Opportunity There is massive market opportunity to sell to SMB businesses. Efficient Go To Market There are a lot of ways to GTM as an SMB. With SMB, you want hundreds or thousands of little merchants to pay you every month. Nail an efficient SMB motion before trying to move upmarket.

Scale 245

Scale SMB Merchant Services Payment Methods 245

SaaStr

OCTOBER 8, 2024

To win for SMBs, you need to own the whole operation stack for them to achieve the ROI they need. You Need to Own the Whole Operation In SMB Vertical SaaS For a pizza shop, it isn’t rocket science or that complex of a business, so you can chip away at jobs to be done and give them world-class solutions. People miss that in vertical.

Scale 283

Scale Scaling Point of Sale SaaS 283

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

DECEMBER 17, 2020

SaaStr Scale 2020 was a huge hit, thank you to the 20,000+ that registered or watched our sessions! 2: “Stop Losing Customers: 5 Steps to Creating Customers for Life with Freshworks” A very popular deep-dive on SMB customer success with $100m+ ARR Freshworks. #3: Let’s take a look! #1:

Scale 258

Scale Scaling SMB Acquisition 258

SaaStr

FEBRUARY 1, 2022

And that challenge some of your assumptions on how to scale. 60% of Asana’s customers come from self-service, 40% from sales. This is trending to 50/50 now that Asana has crossed $400m in ARR, but still a reminder a self-serve motion combined with sales jumping on the bigger deals can scale very, very far.

Scale 363

Scale SMB SaaS Scaling 363

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 279

Scale Sales Hiring Scaling Revenue 279

SaaStr

DECEMBER 7, 2022

SaaStr Scale is our biggest digital / on-line event of the year and its streaming LIVE TODAY – Wednesday, December 7th! SaaStr Scale is starting soon and will be live streaming today! . Revenue Confidential with Rippling and Founders Fund Sam Blond, Partner at Founders Fund Matt Plank, VP Sales at Rippling.

Scale 48

Scale VP of Engineering Scaling SMB 48

SaaStr

JUNE 9, 2021

A ways back, I asked Brendon Cassidy, VP of Sales at LinkedIn, Adobe Sign / EchoSign, and Talkdesk to put together his playbook for double sales. … How We Increased Sales Nearly 100% In One Quarter at HackerRank – Brendon Cassidy. I thought it was a great checklist for all of us to take a look at.

Scale 291

Scale Sales Recruiting Sales Hiring Sales 291

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 263

Scale CTO Hire Cloud Scaling 263

SaaStr

NOVEMBER 16, 2021

We’re getting excited for the third annual SaaStr Scale on December 15. It’s all digital, and all free. appeared first on SaaStr.

Scale 264

Scale Scaling SMB Revenue 264

SaaStr

JUNE 27, 2019

Erica has led New Relic through massive growth, scaling the company’s enterprise business 10x since she joined the business pre-IPO. Erica will share the five critical steps (and some lessons learned along the way) for scaling in the enterprise. We operate at great scale. Want to see more content like this?

Scale 240

Scale Enterprise Scaling Sales Hiring 240

SaaStr

JUNE 7, 2021

If a sales rep closed a deal, A customer success manager should take it over. Find a way to fund both, even with SMBs. And as startups scale, many try to automate away support and success for the smaller accounts. The grey area is often with SMBs. Support has to handle a lot of routine SMB issues anyways.

Customer Success 353

Customer Success Scale SMB Sales 353

SaaStr

AUGUST 21, 2023

So SaaStr itself is a little funky — we only have 9 team members but a fair amount of scale in terms of reach, revenue, and in some cases, software utilization. So we reached out to the leading SMB vendor. 5x more for the SMB vendor! $50k But the SMB vendor is pushing hard to monetize its biggest SMBs the most.

SMB 246

SMB Enterprise Scale Pricing 246

SaaStr

AUGUST 29, 2022

SMB SaaS has a lot going for it: – Millions of them – Short sales cycles – Easier compete. But, it's often hard to get to $100m ARR selling just to SMBs. sell just to SMBs pic.twitter.com/Po1I2aMaBK. So many VCs and others have gotten more and more excited about SMB SaaS. Much higher.

SaaS Payments 347

SaaS Payments Scale SMB PayPal 347

SaaStr

FEBRUARY 16, 2021

Q: What are the common mistakes in B2B sales in the early-ish days? The list could be endless, and it can vary a lot based on type of customer, type of sale, etc. The list could be endless, and it can vary a lot based on type of customer, type of sale, etc. Firing” prospects. Do not fire a prospect. A lot more.

Scale 286

Scale Sales Hiring Sales SaaS 286