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

MAY 18, 2025

Dear SaaStr: How Should I Specialize My Sales Team? One thing is clear: most founders and VPs of Sales and CROs look back and wish they’d specialized their sales team earlier. SMBs often require a high-velocity sales motion, while enterprise deals are slower and more relationship-driven.

Scale 165

Scale Sales Healthcare SMB 165

SaaStr

MAY 3, 2025

Heres how Id break it down: 0 t o $ 1M ARR: Founder-Led Everything Sales : Founders should lead sales. No VP of Sales yetdont even think about it. 1 M t o $ 3M ARR: Build the Foundation Sales : Once you have 2 reps consistently hitting quota, its time to hire your first VP of Sales. AI can’t do it all.

Sales Hiring 254

Sales Hiring Part-Time VPE CTO Hire Scale 254

SaaStr

DECEMBER 29, 2024

Top Posts of the Week: #1: Salesforce: Actually Were Going to Hire 2,000 Sales Execs Now To Sell AI #2: Gong: $100k Deals Take About 70 Days to Close #3: Why The Greatest Sales Teams Just Kill It On Dec 31. When Everyone Else Has Gone Home. #4:

AI 290

AI Sales Hiring Pricing Development 290

SaaStr

FEBRUARY 14, 2024

Dear SaaStr: How often will a sales engineer also wear a customer success hat in an early stage of an SaaS startup? The “traditional” role of a sales engineer is to support the sales team through the close of a deal. Pretty darn common. And as you scale, the role should likely end there.

Scale 278

Scale Engineering Customer Success Startup 278

SaaStr

DECEMBER 22, 2024

How Many Sales Reps You Really Need for Next Year #4. But Not Always a Great Win for Their Late Stage Investors Inherent Churn vs. What It Really Takes to Sell To Developers and Engineers with Komodor CRO Jim Hunnewell #3. From Outbound to Channel Partnerships: Your Burning Sales Questions Answered by Jason Lemkin #5.

Churn 278

Churn AI B2B Engineering 278

SaaStr

OCTOBER 14, 2024

Force them to go annual, and you are just adding friction to the sales process. Yes, as you scale you do need to maintain efficiency in sales and marketing. Give that VP of Sales / Marketing / Engineering more time. You can bring in 1 or 2 great sales execs to the team. Focus, focus, focus on 1 core product.

Scale 302

Scale Social Media SaaS Acquisition 302

SaaStr

OCTOBER 11, 2024

You should find, hire, and manage the VPs of Sales, Marketing, Customer Success, Product and Engineering and even Finance yourself. I think $1.5m ARR is too early for an experienced COO in 95 cases out of 100 — unless it’s a total rocketship and you plan to be at $10m+ ARR within 12 months. ARR you should still be the COO.

Sales Hiring 304

Sales Hiring Startup Finance Engineering 304

SaaStr

OCTOBER 19, 2024

46,771 Views: “From Burn-Out to $100M in ARR with Jason Cohen, Founder of WP Engine” #6. 41,000 Views: “Veeva: The Biggest Vertical SaaS Success Story of All Time” with Founder/CEO Peter Gassner #7, 37,000 Views: “Sales Mistakes that Can Kill Your SaaS Business & How to Avoid Them” #8.

Acquisition 289

Acquisition Innovation Startup Engineering 289

SaaStr

JULY 5, 2022

By moving from Freemium to “Contact Me” only (albeit with transparent pricing), sales went way, way up. And they probably needed to do this, to get the revenue engine going. So many sales leaders get frustrated with Free editions, very low-cost editions … and the Long Tail in general. But it supports them.

Scale 328

Scale Sales Engineering Acquisition 328

SaaStr

MAY 12, 2023

Next up is Jason Cohen, founder of $100m+ WP Engine. Believing a failed experiment disproves a theory Early in WP Engine’s history I tried building an affiliate program to generate sales. It didn’t — we get barely any sales, and those we got were low-dollar and high-churn. We declared it a failure and moved on.

Engineering 297

Engineering Sales Hiring Interviewing Scale 297

Sales Hacker

DECEMBER 17, 2024

As the co-founder and CEO of Intellimize (acquired by Webflow), Guy brings a unique perspective from his journey through iconic companies like Microsoft, Yahoo, and Twitter, as well as his background in aerospace engineering. It includes a breakdown of the Sales AI landscape, adoption of GenAI and Sales software across buyer groups.

Scale 101

Scale Engineering Acquisition Scaling 101

SaaStr

MAY 7, 2024

At SaaStr AI Day, Siqi Chen, founder, and CEO of Runway , discussed his belief of why every role will become a prompt engineering role, along with some no-code AI tips showing how to build products without knowing how to code. Why Is Every Role a Prompt Engineering Role Runway is a next-generation finance platform. How does that work?

AI 281

AI Engineering Sales Hiring ChatGPT 281

SaaStr

NOVEMBER 20, 2024

Historically, the burden of customer feedback fell on the solutions engineers and CS architects. Other Learnings in the GTM Journey GitHub has had to adjust to new sales stages and new buyer personas. Sometimes, you have to say no or push them into a specific package, which is true post-sale for adoption.

Scale 264

Scale AI Scaling Marketing 264

SaaStr

MAY 20, 2025

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. Its not either / or. Or at least, it doesnt have to be. At least not in horizontal plays.

SMB 268

SMB Scale Education AI 268

SaaStr

OCTOBER 13, 2024

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. . … they all failed or came up way short. I felt part of your core job as CEO was to assemble a management team, not complain about how you couldn’t get it all done. I still believe this.

Sales Hiring 263

Sales Hiring CTO Hire Scale Startup 263

SaaStr

DECEMBER 27, 2024

Engineering resources: With thousands of engineers, companies like HubSpot can make substantial AI investments when they choose to 3. Proprietary data access: “We’ve got the zoom data, the calling data, the email data…If you’re a startup breaking in and you want to do some amazing AI work, it’s tricky.”

AI 290

AI Marketing SaaS Interviewing 290

SaaStr

JANUARY 18, 2023

Dear SaaStr: What’s a Good Benchmark for B2B Sales Cycles? To overgeneralize, but to give you a pretty rough sense: Sales cycles are very much impacted by the intent of the prospect. Once you have a bit of an engine going though: Deals < $2,000 in ACV should close on average within 14 days. appeared first on SaaStr.

Benchmarks 334

Benchmarks B2B Sales Engineering 334

SaaStr

JULY 18, 2024

How can you bridge the gap between sales and tech to drive customer success? Sarah Polan, EMEA Field CTO at HashiCorp, and Louise Fellows, VP NEMEA at HashiCorp, explore the relationship between Field CTO and sales to help you understand why it exists and how you can leverage this relationship when you have a highly technical product.

CTO Coach 305

CTO Coach CTO Technical Review Customer Success 305

SaaStr

APRIL 8, 2025

Net net, if the average RevenueCat engineer is twice as efficient as before AI dev tools (and it’s not that simple. The Second “Problem” With Small But Mighty AI Teams … Is Enterprise Sales A tiny team can be fairly efficient with a 100% self-serve and PLG motion. And can it sell and scale sales?

AI 288

AI Sales Hiring Scale B2B 288

SaaStr

FEBRUARY 21, 2025

Key points about SaaStr Annual : Focus on SaaS: Primarily focused on all aspects of SaaS business including sales, marketing, product development, and customer success. Large Audience: Considered the biggest SaaS conference with a large number of attendees from leading SaaS companies, startups, and venture capital firms.

Software 246

Software Scale Venture Capital SaaS 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. An interim VP of Sales can work — if it’s done right.

Scale 342

Scale Sales Hiring Sales SMB 342

SaaStr

FEBRUARY 11, 2021

In SaaS, #1 most common misfire, with a bullet, is the VP/head of sales. It goes something like “You’ve Got to Get Past the Carcass of Your First VP of Sales” or “It’s The Second VP of Sales When You Really Start Selling” or variants thereof. Because in SaaS start-ups, it seems like the majority of first VP Sales fail.

Sales Hiring 363

Sales Hiring Scale Sales Recruiting Sales 363

SaaStr

MARCH 16, 2025

Prior to Datadog, Alex held leadership positions at several high-growth SaaS companies and has a proven track record of building marketing engines that deliver consistent, measurable growth. He spent over eight years scaling their marketing from zero to supporting a multi-billion dollar public company. The problem?

Scale 247

Scale Sales Hiring Scaling Marketing 247

SaaStr

JUNE 16, 2023

Dear SaaStr: How Many Sales Reps Do I Need? You can back into how many sales reps you’ll need in SaaS. Your VPs and Directors of Sales and sales ops and rev ops leaders and sales engineers are cost centers here. Assume 1 sales manager for each 8 sales professionals. 60% is OK, too.

Scale 322

Scale Sales Hiring Sales Headcount 322

SaaStr

FEBRUARY 8, 2025

The Three Types of Context Your AI Needs Your AI agent needs access to: Team documents & engineering specs (the “how it works” knowledge) Systems of record like CRM (the structured data) Unstructured info from Slack, Zoom, etc. That’s the difference between a toy and a real product.

AI 247

AI Artificial Intelligence SaaS User Experience 247

SaaStr

APRIL 7, 2025

I’m shocked we don’t already have this for sales calls. By the end of the year, every single sales call should have a digital representative that can fill in when the human doesn’t know an answer. This will utterly change how we do sales. Don’t wait to launch your AI for a year.

AI 218

AI B2B ChatGPT Scale 218

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

FEBRUARY 2, 2025

Sales up 22%! For example, Owner.com operates with a notably flat structure, maintaining a ratio of one product manager to sixteen engineers. Engineers are empowered to make technical decisions and write their own product requirement documents, functioning essentially as “mini-founders” within the organization.

AI 227

AI Technical Review Artificial Intelligence Systems Review 227

SaaStr

MARCH 17, 2025

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. He brought 20+ engineers with him, with outsized equity packages. Stay in the Deals: If youre selling a complicated product, youll need to stay deeply involved in sales, even as you hire.

Sales Hiring 250

Sales Hiring Scale Scaling Engineering 250

SaaStr

MARCH 12, 2025

The 4 Things Most Founders Get Wrong About Marketing: “We’re a product company, not a marketing company” – The hard truth is that 9 out of 10 B2B companies spend more on sales and marketing than R&D. Mix in the classic conflict between sales and marketing teams, and you’ve got a recipe for disaster.

Sales Hiring 207

Sales Hiring Marketing Technical Review Underperforming Technical Team 207

SaaStr

APRIL 5, 2025

Here are the five channels that worked for Rupa: Search Engine Optimization (SEO) Social Proof and Trust Building Educational Partnerships and Rupa University Conferences and Event Sponsorships Outbound Sales and Data Quality Lets dive into each. Rupas sales team sent highly specific emails, doubling their ROI.

Scale 232

Scale AI Search Sales Hiring Acquisition 232

SaaStr

JULY 22, 2024

So lately I’ve watched a lot of new VPs of Sales crash and burn when they start. You’re going to possibly laugh at a few, but here are the Top 10 Mistakes I’ve Seen New VPs of Sales Make The First Week on the Job. Is it their fault? The CEO’s? It really doesn’t matter in the end. No chance. #3.

Sales Hiring 312

Sales Hiring Scale Sales Interviewing 312

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 290

Forecasting SMB Sales Technical Review 290

SaaStr

MAY 13, 2025

A playbook ensures your sales team knows how to handle these situations without making ad-hoc promises that strain your team. If a customers demands will take months of engineering time and dont align with your roadmap, its better to pass. This should include: Criteria for evaluating requests (e.g., Pricing guidelines for custom work.

Outsourcing Services 200

Outsourcing Services Outsourced Development Enterprise Pricing 200

SaaStr

APRIL 30, 2025

This efficiency is driven by their tailored go-to-market engine, which includes high-velocity inbound marketing, strategic partnerships with private equity firms, and a dedicated sales team for upselling Pro products and FinTech solutions. This shift has been critical to scaling beyond $500M ARR. But it’s early.

Payments 147

Payments Payment Services SaaS Payments Payment Solutions 147