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. Follow the Pilot-Repeat-Enlarge Methodology Pilot : Start small with minimal investment. Negotiate with vendors for smaller initial commitments.

Scale 244

Scale Sales Hiring Scaling Marketing 244

SaaStr

NOVEMBER 17, 2023

Dear SaaStr: Why Are So Many CEOs Former Engineers, or At Least Have Technical Backgrounds? I’ve come to almost exclusively invest in founder-CEOs that are engineers. You need to recruit a great engineering team. You don’t need to be an engineer to do this, but most “salespeople” CEOs can’t pull this off.

Outsourcing Services 298

Outsourcing Services Engineering CTO Scale 298

SaaStr

JANUARY 14, 2025

Their “sense” of what things cost is often just way too low once they start to invest the first round of VC capital they raise. You can’t pay a great engineer in the Bay Area $60k a year forever. And how much that dramatically drives up the burn rate and cost of doing business. Dramatically.

Startup 279

Startup Finance Engineering Investment 279

SaaStr

NOVEMBER 20, 2024

Historically, the burden of customer feedback fell on the solutions engineers and CS architects. Don’t underestimate the investments you need to make here to be compelling to your customers. Another big investment during rapid growth is digital moments. Be disciplined about prioritizing that feedback and communication.

Scale 264

Scale AI Scaling Marketing 264

SaaStr

JULY 18, 2022

The competition for engineers is fiercer than ever — and that means that companies need to work harder than ever to attract and retain them. Everyone involved has experienced these struggles firsthand, and what they say may help inform how you treat the engineers on your team. #1. Focus on retaining your engineers from day one.

CTO Coach 278

CTO Coach CTO Hire New CTO Engineering 278

SaaStr

SEPTEMBER 14, 2023

But with that out of the way, let’s talk just enough about financial accounting to explain why Big Tech Companies both acquire smaller ones — and do corporate VC investment. Because in the short-term, it often costs basically close to nothing to acquire a smaller startup with cash on hand, or do a corporate VC investment.

Acquisition 305

Acquisition Investment Headcount Banking 305

SaaStr

APRIL 28, 2025

” Despite his engineering background, Sekar helped Meraki build a scalable go-to-market engine for their wireless networking products. At both Meraki and Samsara, they launched their second and third products within 1-2 years of their first, deliberately allocating engineering resources away from their successful core offerings.

Scale 263

Scale Transportation Scaling SMB 263

Tom Tunguz

MARCH 6, 2023

As machine learning becomes core to every product, engineering teams will restructure. In the past, the core engineering team & the data science/machine learning teams worked separately. The core engineering team ships the product & focuses on reliability. The forces behind this change have been brewing for some time.

Artificial Intelligence 250

Artificial Intelligence ChatGPT Engineering Machine Learning 250

SaaStr

OCTOBER 13, 2024

I try to work with (and invest in) CEOs that are better than me. She should hire leaders for Sales, Marketing, Engineering, Product and Customer Success, or at least most of them. Dear SaaStr: Why did Jason M. Lemkin Change his Point of View on The Value of a COO for Earlier Stage Startups? they all failed or came up way short.

Sales Hiring 263

Sales Hiring CTO Hire Scale Startup 263

Clouded Judgement

MARCH 28, 2025

Now, you still had to go out and hire engineers to build the product, build out the GTM team to build brand and distribution, etc. And now, engineering and distribution (go-to-market) constraints are greatly reduced with AI. Solutions like Cursor, Codeium, GitHub copilot, etc greatly democratized engineering.

Cloud 299

Cloud AI Scale Scaling 299

SaaStr

MAY 13, 2025

I got it wrong for a while too, until I started invest in and working with more vertical SaaS companies. We’ve all learned we need to generally bring second products to market earlier than before, often as early as $10m ARR, to keep the engine going.

SMB 208

SMB Engineering Branding Investment 208

SaaStr

OCTOBER 23, 2024

” Investing for growth has been pretty flat year over year for SMBs, which means there is money there, but they’re holding onto it. With a trillion in payment volume coming through BILL in the last five years, managing the payment and compliance engine has required an ongoing effort of a sizable team.

SMB 312

SMB Payment Services Payments Payment Methods 312

SaaStr

FEBRUARY 17, 2022

Invest in your tech stack so that you keep growing while you scale. Developing a solid, data-driven strategy is key to making informed decisions for your marketing engine. Then, focus and invest in the simplicity of the customer journey, so when they experience the product, you don’t lose them in that process.

Engineering 278

Engineering Scaling Marketing Acquisition 278

SaaStr

SEPTEMBER 14, 2023

But with that out of the way, let’s talk just enough about financial accounting to explain why Big Tech Companies both acquire smaller ones — and do corporate VC investment. Because in the short-term, it often costs basically close to nothing to acquire a smaller startup with cash on hand, or do a corporate VC investment.

Acquisition 263

Acquisition Investment Headcount Banking 263

Tom Tunguz

JULY 16, 2024

In web2, the engineering team building a payment processing system will convey to the analytics team the data schema. We are thrilled to announce our investment in Allium , alongside friends at Amplify & Kleiner Perkins. In the world of blockchain, these processes are even more complex.

Blockchain 244

Blockchain Merchant Services Payment Solutions Investment 244

SaaStr

FEBRUARY 2, 2025

Their platform helps restaurant owners, who typically earn less than $50,000 annually in profit, create professional online presences without significant investment in time or resources. For example, Owner.com operates with a notably flat structure, maintaining a ratio of one product manager to sixteen engineers.

AI 222

AI Technical Review Artificial Intelligence Systems Review 222

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. And then originally trained as an aerospace engineer. Scott Barker: [6:39] We almost exclusively invest.

Scale 100

Scale Engineering Acquisition Scaling 100

SaaStr

MARCH 17, 2025

Im investing in fact at SaaStr Fund in a solo founder right now. He brought 20+ engineers with him, with outsized equity packages. Dear SaaStr: I Have No Co-Founder. What Should I Do? Thats okayplenty of successful startups have been built by solo founders. But Ill be honest: its harder. Prioritize Great Early Hires.

Sales Hiring 250

Sales Hiring Scale Scaling Engineering 250

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. Personalized Emails : Conrad stressed that generic emails get ignored.

Scale 230

Scale AI Search Sales Hiring Acquisition 230

SaaStr

APRIL 25, 2023

In last week’s Workshop Wednesday , President Sales & Field Engineering Chris Donato and SVP Business Development & Ecosystem Shelli Vivona shared how to scale out a go-to-market org. They’ve invested in in-person training, a three-day offsite where the training went deep and resulted in certifying.

Scale 242

Scale VP of Engineering Sales Hiring Engineering 242

SaaStr

MARCH 18, 2025

Joselyn Goldfein , Managing Director at Zeta Venture Partners, which invests in AI and data infrastructure-focused startups from inception through seed stage And see everyone at 2025 SaaStr Annual, May 13-15 in SF Bay!! This is exactly backward. The winning approach: Start with employee-facing tools that deliver measurable productivity gains.

Technical Review 189

Technical Review Artificial Intelligence AI Marketplace as a Service 189

SaaStr

DECEMBER 23, 2022

Focus on scaling what works best, but don’t over-engineer and waste valuable time. When you know something is working, you invest in scaling it. “It Samsara found a repeatable motion that allowed them to invest in a local team familiar with the challenges. As a result, they achieved a 15x return on their marketing investment. .

Scale 237

Scale Engineering Marketing Scaling 237

SaaStr

NOVEMBER 7, 2024

Models built by OpenAI, Google, and Anthropic have billions of dollars to invest in training these models, so you have more powerful engines under the hood at no cost to you. There are multiple, so you have a choice and can choose between them. You do pay however pay for inference.

AI 264

AI Artificial Intelligence ChatGPT Mobile 264

SaaStr

APRIL 30, 2025

But remember, this requires significant investment in product depth and breadth. 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.

Payments 147

Payments Payment Services SaaS Payments Payment Solutions 147

Tom Tunguz

JUNE 20, 2020

The median startup with between 1-5M in ARR will have 12 engineers, 6 in sales and 3 in marketing. As the company grows and reaches 50-100M in ARR, the ratio of engineers to salespeople asymptotes to 1:1, down from 2:1. In the earliest days, leads head all of these teams.

Scale 363

Scale Scaling Sales Hiring Software Review 363

SaaStr

JULY 20, 2024

Invest in People You want to keep the bar high on talent, especially in hypergrowth, and not just in the early stages. Invest Heavily in Onboarding Your typical employee takes about three to six months to get ramped. Aligning and Scaling the GTM Engine One of the core functions when hiring talent is engineering, product, and design.

Sales Recruiting 304

Sales Recruiting Sales Hiring Scale Engineering 304

SaaStr

APRIL 7, 2025

The AI Is Shockingly Good – It’s Often Better Than Me (For Some Things) One of our fastest-growing portfolio companies had all board members and investors provide feedback on their investment memo – and the AI won. Look at Assistant UI and other frameworks – your engineers can implement this in a week.

AI 215

AI B2B ChatGPT Scale 215

SaaStr

MAY 29, 2025

Do you invest in upskilling your middle performers, or do you focus resources on amplifying your stars? Digital Sales Engineers (SEs) that join every customer call. Top performers will see exponential gains from AI augmentation, while average performers may struggle to adapt and could find themselves displaced.

Sales Hiring 175

Sales Hiring Underperforming Technical Team AI Scale 175

Tom Tunguz

NOVEMBER 7, 2024

In a daring feat of economic analysis, I asked it to calculate if the after-tax returns of two ETFs were statistically significant & to compare the energy portfolios using the 13-Fs of a few hedge funds for investment ideas. Then The New Yorker. It’s an approach to solving a computer science problem I never would have considered.

Artificial Intelligence 185

Artificial Intelligence AI Engineering Investment 185

SaaStr

MARCH 12, 2025

Reverse Engineer Marketing from Buyer Empathy Great marketing starts with understanding the buyer’s state of mind. This isn’t just about priceit’s about the importance of the purchase and how much time/energy buyers will invest in making the right decision. But marketing shouldn’t be intimidating.

Sales Hiring 204

Sales Hiring Marketing Technical Review Underperforming Technical Team 204

SaaStr

FEBRUARY 7, 2025

For context,Ron has an MBA and a master’s in engineering from Stanford. Final Advice for Revenue Leaders After nearly a decade of scaling Databricks, Ron has one core piece of advice for revenue leaders: hire the best people and invest in them. If I could go back, Id tell myself to invest even more aggressively early on.

Scale 182

Scale Sales Hiring Scaling Revenue 182

SaaStr

SEPTEMBER 4, 2021

The bottom line is every professional VC firm and investing entity divides its investments up into 3.5 When you want to increase their ownership, and/or do “Super Pro-Rata” (invest more than your % ownership share) in the next round. You want to be careful about investing further. You are out. It’s OK.

Investment 67

Investment Engineering Leadership 67

Tom Tunguz

JUNE 2, 2024

As data has become a critical component of analytics & production systems, data engineers require more sophisticated tools to manage their data transformations. A short SQL statement can delete a table , reformat date into the US format, or compute the average quota attainment by account executive by region over a company’s history.

Scale 185

Scale Investment Finance Software Development 185

Tom Tunguz

JANUARY 17, 2021

From time to time, I chart the fastest growing categories of startup investment in the US for seed through Series C. The automation of QA is a secular trend that perhaps accelerated with more software engineers working from home. Here are 2015 , 2017 , This year, I was certain the categories would have been influenced by COVID19.

Startup 362

Startup Software Engineering Finance Engineering 362

Tom Tunguz

DECEMBER 6, 2022

PLG companies R&D spend hasn’t produced new business at the same rate as a dollar invested in sales & marketing post-Covid. Some about the data: PLG companies R&D spend hasn’t produced new business at the same rate as a dollar invested in sales & marketing post-Covid.

Headcount 344

Headcount Market Research Acquisition Education 344

SaaStr

NOVEMBER 12, 2022

I’ve had the privilege to invest one way or another in about 35 SaaS companies, both as a VC and as angel. They understand why they got “No”s in the early, pre-traction days, and even, in the early-ish days when they had a handful of customers but wasn’t really taking off yet (my favorite time to invest).

Scale 344

Scale Sales Recruiting Machine Learning Artificial Intelligence 344

SaaStr

MARCH 16, 2025

For example, ask engineers to complete a quick coding challenge or have marketing candidates critique your product. Dont wait too long to make this hireits worth the investment. If you find the perfect candidate at #12, greatbut plan for 30. The best candidates will find these tasks engaging, and itll save you hours of wasted meetings.

Software Review 162

Software Review Interviewing Engineering Startup 162