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

AUGUST 5, 2024

When you find the answer to these questions, you can expand an existing customer base and create cool data-driven case studies to help your sales team bring in net business. 1: Build a Value Narrative Value narratives have been around for some time in pre-sales motions. Often, that doesn’t feed through to post-sales.

Scale 289

Scale Customer Success Scaling Revenue 289

SaaStr

JUNE 22, 2021

This is a positive trajectory, but it presents a challenge for your customer success efforts: How can you scale your support and CS while still delivering a memorable, quality customer experience? According to the Totango report, 77% of respondents said that scale was their top challenge. How Customer Success Drives Growth.

Scale 283

Scale Customer Success Scaling Compensation 283

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. They also saw a lot of customers shortening links and sharing them on the leading link and bio platforms.

Scale 306

Scale Scaling Underperforming Technical Team User Experience 306

Intercom, Inc.

SEPTEMBER 10, 2020

It’s an approach that’s served him well along the road to building the HubSpot sales team, where he was CRO for nine years. That experience led to his bestselling book, The Sales Acceleration Formula. A data-driven framework for scaling. Mark’s latest ebook, The Science of Scaling , outlines a precise framework for success.

Scale 226

Scale Scaling Sales Recruiting Sales Hiring 226

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 189

Sales Hiring Scale Sales Pricing 189

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. Can you start and stop a PLG motion? How do you diagnose and solve churn?

Scale 278

Scale Sales Hiring Scaling Revenue 278

SaaStr

OCTOBER 8, 2024

So, you have to make more money to justify the sales process and recognize that a lot of what drove the first generation of this was rapidly commoditizing and chasing people to the bottom. If you look at the best sales reps, they smash their numbers no matter what. Sales’ greatest filter is brutal work. You need to do it all.

Scale 282

Scale Scaling SaaS Point of Sale 282

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. It’s pretty good, someone did a Tweet storm the other day on Zeb from ClickUp’s presentation at SaaStr Annual 2020. It was packed.

Scale 298

Scale Outsourcing Services Sales Hiring VP of Engineering 298

SaaStr

JUNE 14, 2023

At SaaStr Europa, UiPath’s Dines shared five insights from growing a company from nothing, so other founders can learn what it takes to scale a SaaS startup to $1B+ ARR. Finally, he understood what was needed to scale a business. When you have the courage to be bold, people will take you seriously.” I hired nice crazy people.

Scale 246

Scale Artificial Intelligence Technical Review Software Review 246

SaaStr

APRIL 28, 2025

You Always Learn More Than You Expect When I was scaling Adoe Sign / EchoSign, I didnt visit customers enough early on. Should You Still Visit Your Prospects In Person? Roadmap Presentations Are Gold If youre unsure how to structure these visits, do a roadmap presentation. Heres why it works: 1. Almost Certainly 2.

Scale 126

Scale Travel Technical Review Retention 126

SaaStr

FEBRUARY 15, 2021

There’s a slide I see again and again from start-ups: 2 of the early sales reps are at 100% of quota, sometimes 150%-200%. So why so often, do only 2 of the first 8-10 sales reps perform? The first 2 scaled reps you hire that hit plan (some may churn before then) get special training. And 8 others? Well yes, probably.

Scale 348

Scale CTO Hire Sales Hiring New CTO 348

SaaStr

FEBRUARY 1, 2024

As companies scale, they evolve, so how should marketing evolve accordingly to add maximum value? PST, Kady shares the ten things that change in marketing as you scale. PST, Kady shares the ten things that change in marketing as you scale. But, as you grow, you start to reach the limits of what your original ICP presents.

Scale 280

Scale Scaling Sales Hiring Marketing 280

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

OCTOBER 5, 2022

Confluent’s President of Field Operations, Erica Schultz, explores different tactics businesses can employ to scale revenue and increase efficiency in the current macro environment. As you look to scale your business and make your processes more efficient, it’s essential to foster a shared understanding of who your target customer is.

VP of Engineering 245

VP of Engineering Scale Scaling Sales Hiring 245

SaaStr

MARCH 25, 2023

So one recent survey we did really brought out a healthy debate: does your VP of Sales really need to be a product expert? Many of the comments said it was more important a VP of Sales understand process and leadership more than the product itself. Be present. If they are just saying the wrong things to customers and prospects.

Scale 297

Scale Sales Hiring Sales Recruiting Sales 297

SaaStr

DECEMBER 21, 2022

Airtable CEO Howie Liu shared Airtable’s journey into enterprise, what he’s learned from scaling the company, and his best advice for other SaaS companies looking to make a similar move. Before you think about scaling for enterprise, you must first build the right company foundations. Build the right foundations.

Scale 245

Scale Enterprise Scaling Management 245

TechEmpower SaaS

JULY 31, 2023

One way to approach that last question is to use this simple model: Customer Acquisition Cost (CAC) How will your business reach prospects? Don’t worry about scaling just yet. If your numbers work out, then scaling becomes a question of capital. Be sure to check out the entire presentation. How will you convert them?

Metrics 390

Metrics Startup Scale New CTO 390

SaaStr

FEBRUARY 25, 2025

The Best Speakers In The World With hundreds of sessions from proven SaaS leaders who have scaled companies to significant revenue milestones, SaaStr Annual offers practical, actionable insights you won’t find elsewhere. Sessions typically focus on real metrics, strategies, and lessons learned, not theoretical concepts.

Sales Recruiting 193

Sales Recruiting Scale CTO Hire Sales Hiring 193

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

OCTOBER 10, 2022

From a venture capital perspective, there’s now a premium on driving efficient growth rather than growth at any cost. . “Sales and marketing alignment is a terrific place to figure out and improve efficient growth.” . From the get-go, ensure alignment between sales and marketing teams on goals and anticipated outcomes.

Scale 328

Scale Sales Hiring Venture Capital Marketing 328

SaaStr

JULY 13, 2022

First, you hire your sales team. Finally, growth occurs when sales, product, and marketing can come together. She draws from personal experience scaling a global product company to $1B and shares common mistakes. Call their previous employers and find out whether your prospective hire was hitting their quotas.

Scale 288

Scale Sales Hiring Revenue Marketplace as a Service 288

SaaStr

OCTOBER 26, 2021

Presented By: Amanda Malko – CMO – G2 – @amandamalko. Intriguing Session Slides: Marketing SaaStr Session #2: “Slow and Steady Wins the Race: Building Marketing Channels Slowly to Achieve Massive Scale with Datadog’s CMO”. Presented By: Alex Rosemblat – CMO – Datadog – @alexrosemblat.

Scale 358

Scale SMB Marketing Leadership 358

SaaStr

MARCH 20, 2023

Vanta’s Chief Revenue Officer, Stevie Case, shares lessons learned from leading Twilio’s mid-market team and shepherding Vanta into a mid-market leader as the company’s first CRO. You want to be ready for this to ensure you can serve this market and prevent hitting speed bumps, particularly late in the sales cycle. What do you do?

Scale 243

Scale Enterprise Scaling SMB 243

SaaStr

OCTOBER 30, 2021

Gorgias is the leading contact center for e-commerce and it’s been a fun one to track at SaaS, from 1,000 to 3,000 to now 7,000 customers. Their CEO will join us at SaaSr Scale 2021 on December 15 to talk about using data to get to 10,000 SMB customers! Your sales process should not be a closed box with little insights. .

Scale 290

Scale Sales Hiring Sales Underperforming Technical Team 290

SaaStr

MAY 16, 2025

Look don’t throw money away on sales & marketing. If your sales team can’t close anything , you need to part ways. But more often, sales and marketing is closing some deals, just not enough. Audit your sales and marketing spend at a channel-by-channel level. Should We Cut and Marketing To The Bone?

Marketing 164

Marketing Scale Churn Content Marketing 164

SaaStr

JANUARY 11, 2022

Let’s talk about why it’s a good investment: Trade shows / events produce a lot of so-called “leads”, but a lot of cr*p leads and long lead time leads. Many leads need 2-3 touches, 2-3 contact points, before they close. You gotta be present. All of his prospects. True enough.

Scale 338

Scale Investment Retention Customer Success 338

Tom Tunguz

SEPTEMBER 8, 2022

It formed the basis for a career at HubSpot predicated on consistent quantitative analysis to scale the go-to-market, which he detailed in the Sales Acceleration Formula in 2015. I think it’s still one of the best books on how to repeatably scale sales teams. What would the chart above look like for your sales team?

Sales Hiring 349

Sales Hiring Sales Recruiting Scale Marketing 349

SaaStr

AUGUST 16, 2022

But even there, to truly scale, they went more enterprise and built out a full enterprise sales and marketing function. What works to get you leads? The magic is in getting them together, and inviting a bunch of prospects. And invite all your prospects and your customers. At least for a while. But I was wrong.

Scale 332

Scale Sales Hiring Marketing SaaS 332

SaaStr

OCTOBER 8, 2021

If you missed out on attending SaaStr Annual 2021 – where our outdoor format earned an analogy to the “ Coachella of SaaS ” – or just want to understand PLG better, here are 6 sessions to study: PLG SaaStr Session #1: “Mastermind Masterclass: Beyond Product-led Growth: 7 Lessons Learned in Product-Led Scaling with Dropbox’s GM”.

Scale 363

Scale Engineering Revenue Scaling 363

Andreessen Horowitz

OCTOBER 18, 2023

It’s also important to recognize that although much of this post focuses on large-scale nuclear fission reactors—because that’s what have been delivering civilian power for the past several decades—smaller, more modular reactors will likely play a major role going forward, perhaps as a means to address more local, and even hyper-local, energy needs.

Scale 28

Scale Scaling VP of Engineering Construction 28

SaaStr

AUGUST 23, 2021

Selling mid-market and enterprise software to manage strategic accounting and financial close and account reconciliation in particular is a sizeable market, but one with real work and sales cycles to sell and close, and with more competition than you might think. I love seeing how they present both side-by-side. Year 2 is scaling up.

Scale 279

Scale Scaling Enterprise Cloud 279

SaaStr

APRIL 4, 2025

Come meet them (and also watch 100+ present live at our first AI Demo Stage ) at 2025 SaaStr Annual, May 13-15 in SF Bay!! We automated contact centers employing >100 human agents and now handle their incoming customer support and sales calls, end-to-end. Businesses use us for customer support, leads qualification, and more.

AI Search 178

AI Search AI Startup Scale 178

Tom Tunguz

JUNE 25, 2020

The presentation is embedded below. It contains data on go to market team structure, performance by sales function, marketing spend benchmarks, and customer success priorities. 1:1 AE/XDR ratios are the most common in both inside and outside sales teams. But, it’s important to consider sales cycle when setting ramp time.

Headcount 364

Headcount Scale Benchmarks Retention 364

SaaStr

MAY 1, 2024

Most SaaS companies steer away from phone support in general, and especially for lower-end and trial prospects/customers. At scale it can be expensive, no doubt. Especially if you can segment out support issues (where you should still pick up the phone) from questions from prospects and trial users. Be Present.

Outsourcing Services 290

Outsourcing Services Scale Banking Branding 290

SaaStr

MARCH 7, 2021

Yes, you can manage the sales team yourself. Cash was tight and I didn’t know any great VPs of Biz Dev, so between myself and my VPs of Sales, Product and Customer Success, we all jointly managed our key partners. Fight and create mindshare with partners that deliver you leads. Get on jets and go meet them. A lot more.

Part-Time VPE 299

Part-Time VPE Sales Recruiting Sales Hiring Scale 299

TechEmpower SaaS

DECEMBER 11, 2023

Do you anticipate scale issues presently or in the future? Will you have direct access to a lead developer? Do you have the basics already defined and merely need them fleshed out? Or is your project a clean slate? Are there complexities revolving around algorithms or databases? Communication: Evaluate their communication style.

Software Development 443

Software Development Development Software Review Software 443