SaaStr

APRIL 28, 2025

The Journey: From WiFi to IoT Fleet Management Sekar’s journey began unexpectedly when he joined Meraki (founded by MIT researchers Sanjit Biswas and John Bicket) to help them figure out marketing and sales “from first principles.” This cross-pollination effect accelerated product development in unexpected ways.

Scale 260

Scale Transportation Scaling SMB 260

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

APRIL 16, 2022

Per LinkedIn data, SMB AEs at some of the top SaaS and B2B companies have: an average base salary of $70k, an average OTE of $125k, and. SMB AE | TOP 30 Sales Organizations. Sales Organization 1 Miro 2 Okta 3 Arctic Wolf 4 Sprout Social 5 Google 6 Clickup 7 Cisco Meraki 8 Microsoft 9 Klaviyo 10 AWS 11 Rippling 12 Fivetran.

SMB 335

SMB AWS SaaS B2B 335

SaaStr

APRIL 28, 2025

What’s Changing in Sales: The AI Revolution is Here — and Coming Fast After analyzing 139,000+ conversations through SaaStr’s New AI, it’s now clear from the data: AI is about to fundamentally transform B2B sales. This isn’t some distant futureit’s happening right now.

AI 244

AI Underperforming Technical Team Sales Technical Review 244

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 276

SMB B2B Enterprise Scale 276

SaaStr

OCTOBER 16, 2024

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. But even as they push more and more into the enterprise, the SMBs still are buying. A reminder to not stay too reliant on direct sales as you scale. Either way — ouch.

Scale 284

Scale Compensation SMB Cloud 284

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. You shouldn’t be adding a bunch of sales reps or spending a bunch of money on marketing if the economics aren’t sustainable. Kyle made this mistake in his first startup.

Scale 301

Scale SMB Sales Hiring Sales 301

SaaStr

NOVEMBER 27, 2023

​Accurate sales forecasting is more critical to business success than most realize. During SaaStr Annual , Eric Huff, VP of Sales Strategy and Programs, and Theresa Stevens, Regional VP of the SMB sales team, shared an “under the hood” look at how Salesforce does its internal forecasting using Salesforce.

Forecasting 284

Forecasting SMB Sales Technical Review 284

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 283

SMB Scale Marketing Sales 283

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 157

AI Scale Sales SMB 157

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 293

Revenue Scale Sales Hiring Compensation 293

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 284

Sales Hiring Scale Systems Review Interviewing 284

Tom Tunguz

MARCH 27, 2023

Sales cycles shifted dramatically in 2023. Slower sales cycles create pipeline shocks & startups are feeling the impacts. The average startup saw a 24% increase in sales cycle from early 2022 to 2023. 60 day sales cycles are now 75 days. But the latency isn’t evenly distributed.

Startup 350

Startup SMB Headcount Sales 350

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. I’d suggest a few basic thoughts and rules: If you have sales involved, then you need customer success, too. Just assign a certain amount of ARR per each SMB customer success manager.

Customer Success 353

Customer Success Scale SMB Sales 353

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 257

SaaS Payments Payments Payment Solutions Payment Services 257

FastSpring

FEBRUARY 6, 2025

In this episode, we’re going to be talking about how SMB digital brands can win the best talent Joining us for that conversation is someone who knows quite a bit about that. X sales force, X meta. The post How SMB Digital Brands Can Win the Best Talent appeared first on FastSpring. I’d like to welcome Lizzie Mintus.

SMB 107

SMB Sales Recruiting Branding Sales Hiring 107

SaaStr

JULY 11, 2023

How do you win with a high-velocity sales strategy in a fast-moving, competitive market? In a special session of Workshop Wednesday, Gorgias Founder & CEO Romain Lapeyre and Gorgias VP of Sales & Partnerships Aasif Osmany share their learnings, advice, and hacks for optimizing your sales process. Sign up for free.

Sales Hiring 200

Sales Hiring SMB Sales Recruiting Payment Methods 200

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 261

Scale SMB Scaling Innovation 261

SaaStr

APRIL 14, 2025

AI Speakers: CEO Snowflake + CEO Observe: Where B2B Applications Are Going CEO Box Aaron Levie: AI, Agents and The Next Era of SaaS COO Google Cloud Francis deSouza: Hyperscalers: The Future and More CTO Rubrik: Co-Founder & CTO, Arvind Nithrakashyap CTO Neo4j: Philip Rathle (Valuation $2B+): How Revolut Left Salesforce and More: Rolling Your (..)

VP of Engineering 204

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

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. Waiting too long to start their enterprise planning.

Enterprise 244

Enterprise Sales Hiring Scale Outsourced Development 244

SaaStr

DECEMBER 1, 2021

So SaaS companies now must think about ways to sell to prospects before the sales team even contacts them. . This means that your team’s work is far from over at the closing of the sale –– your customer service must be on point, your product useful and simple to use. . Key Highlights: Adopt a product-led growth mindset.

Software Review 284

Software Review SMB Enterprise Software 284

SaaStr

APRIL 30, 2025

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. While ServiceTitan started as an SMB-focused platform, theyve steadily moved upmarket. Just above non-GAAP break-even (3% non-GAAP margins) 110% NRR and 95% GRR $10.5B

Payments 144

Payments Payment Services SaaS Payments Payment Solutions 144

SaaStr

JULY 27, 2022

If a SaaS business hopes to win over the SMB market successfully, it will need a precise GTM approach. Founded in 2015, PayFit is a software company that empowers entrepreneurs and SMBs to digitize payroll and HR processes. Secret 1: A Self-Serve Product is Non-Negotiable For SMBs.

SMB 244

SMB Sales Hiring Scale B2C 244

SaaStr

JUNE 8, 2024

So David Obrand, CEO of Salesloft, had a great post the other day on consistency being one of the biggest challenges with enterprise sales. In SMB sales, you see the variance in performance among reps really fast, and you can take action fast. That’s the nature of a very short sales cycle. The Best VPs of Sales?

Sales Hiring 293

Sales Hiring Scale Sales SMB 293

SaaStr

JANUARY 21, 2022

Dorian Stone , Head of Organizations Revenue at Grammarly, is here to share lessons from his experience of scaling the company from consumer to SMB to Enterprise to help you steer your expansion efforts in the right direction. The admin, influential decision-makers, and consumer sales reps can be the same people in a Consumer or SMB setting.

Scale 246

Scale SMB Enterprise Sales Hiring 246

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 341

Scale Sales Hiring Sales SMB 341

SaaStr

JANUARY 21, 2020

Justin Welsh, former SVP of Sales at PatientPop explains how he started in SaaS in 2009 as the second sales hire at Zocdoc. Justin used Sales Culture to grow a successful PatientPop team to 140 employees and 55 million in revenue. Justin Welsh | SVP Sales @ PatientPop. I was a local sales manager or regional manager.

Sales Recruiting 332

Sales Recruiting Sales Hiring Scale Sales 332

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

MARCH 18, 2021

We’ve talked a lot about hiring a VP of Sales at SaaStr , and if you hire a stretch VP of Sales (as most of you will) … how much you can stretch. A related question is — just how quickly can you gain the requisite experience to be a true first time VP of Sales? Month 6: promoted to first SMB rep.

Sales Hiring 301

Sales Hiring Sales Recruiting SMB Sales 301

SaaStr

JANUARY 19, 2025

And we’ve done several great live Workshop Wednesdays with top CROs and VPs of Sales in Vertical SaaS in particular recently that are all A+ and worth watching: #1. It takes getting out in the field, and creating a ton of true value — before the sale. #2. See you there! How Kyle does it here: #3. How Kyle does it here: #3.

Scale 189

Scale Sales Hiring Scaling SMB 189

SaaStr

APRIL 13, 2022

Dear SaaStr: How Many Deals Can a Sales Rep Close Per Month? A successful but not top 5% sales rep in SaaS typically can close: 20–50 deals a month if $0.5k-$2k ACV , i.e., very transactional 1–2 call close. Think about an SMB rep doing small-but-not-tiny deals — say $2k ACV. Usually all inbound. deals image from here.

Sales 315

Sales SMB Enterprise SaaS 315

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 346

SaaS Payments Scale SMB PayPal 346

Tom Tunguz

FEBRUARY 26, 2025

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. Salesforce sells CRM seats based on an aggregate ROI of increased sales productivity for example.

SaaS Payments 283

SaaS Payments Pricing Strategy Scale 283

SaaStr

MAY 23, 2023

So leading growth stage VC Iconiq has published its latest and very detailed Definitive Guide to Sales Compensation here. Corners were cut in the boom times of 2021, but we are back to sane sales models. Renewals, if they are done by sales, are paid out at about 40% of an initial commission. Everyone should have a read.

Compensation 301

Compensation Scale Sales SMB 301

SaaStr

FEBRUARY 1, 2022

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. A reminder that you don’t need to settle for sub-100% NRR from SMBs.

Scale 363

Scale SMB SaaS Scaling 363

SaaStr

FEBRUARY 8, 2022

Scaling a sales organization isn’t easy. Knowing which metrics matter and how to analyze them to increase your revenue and hit organizational sales goals is essential. . What makes a sales organization grow? What’s the best way to grow a sales organization? Enter your email below for the latest SaaStr updates.

Scale 292

Scale Sales Hiring Compensation Sales 292

SaaStr

OCTOBER 4, 2022

Dear SaaStr: At What ACV Can We Afford a Sales Team? Even with a very efficient team, it’s tough to afford a sales team much below $299 a month / $3k a year. Then, to make say $100k a year as an SMB rep, you then have to close 4x that (or more), so say $400k a year, maybe more. At least in the U.S. and Western Europe.

SMB 245

SMB Sales Pricing Revenue 245