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

JANUARY 3, 2025

Or a great growth marketer paired with a great sales team will punch above their weight class. In sales, t he more SMB you are, the more you should lean on your bench. With SMBs in particular, internal promotions can work better due to more “at-bats” and learning opportunities on the front lines.

Sales Hiring 290

Sales Hiring Scale Systems Review Interviewing 290

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

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 325

Scale Scaling Technical Review Systems Review 325

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

APRIL 30, 2024

How do you build GTM efficiency in SMB sales? While this title is SMB-oriented, the advice applies to Mid-Market and Enterprise, too. Ways to scale that don’t include rampant inefficiency and burn. The growth engine from both sales and marketing should to be working before you add gas to it.

Scale 306

Scale SMB Sales Hiring Sales 306

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 317

SMB Scale Sales Hiring Sales 317

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 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 264

Scale SMB Scaling Innovation 264

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 260

SaaS Payments Payments Payment Solutions Payment Services 260

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 278

Scale VP of Engineering Scaling SMB 278

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 147

Payments Payment Services SaaS Payments Payment Solutions 147

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 311

Scale Scaling Strategy Sales Hiring 311

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

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 283

Scale Scaling Sales Hiring SMB 283

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 276

Scale AI SMB B2B 276

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 278

Scale Sales Recruiting Sales Hiring Scaling 278

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 289

SMB Scale Marketing Sales 289

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 284

Scale Scaling SMB compliance 284

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 281

SMB B2B Enterprise Scale 281

SaaStr

MAY 4, 2025

Dear SaaStr: How will Ai Change Sales in The Next 12 Months? It’s already fundamentally remade the contact center and post-sales. And it’s just getting there in sales. This will take sales calls from 10% being great to 95% being great because the AI will always be prepared and accurate.

AI 162

AI Scale Sales SMB 162

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 282

Scale Scaling SaaS Point of Sale 282

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

APRIL 29, 2025

250+ speakers. 12,000+ SaaS leaders. 100B+ in market cap. 250+ speakers. 12,000+ SaaS leaders. 100B+ in market cap. 250+ speakers. 12,000+ SaaS leaders. 100B+ in market cap.

AI Search 165

AI Search AI New CTO Scale 165

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 257

Scale Scaling SMB Acquisition 257

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

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

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

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 290

Scale Sales Recruiting Sales Hiring Sales 290

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