SaaStr

JULY 13, 2020

Q: What was your failed investment experience and where will you never invest funds again? I’ve made about 30 material investments. Most have been successful, but of course not all have and I’ve been reflecting on the ones that didn’t, because they still had attractive elements when I invested. Great CEO But Mediocre CTO.

Technical Cofounder 282

Technical Cofounder Investment New CTO CTO 282

SaaStr

APRIL 14, 2025

800+ VCs Ready to Invest This year, were bringing together over 800 VCs and investors, making SaaStr Annual 2025 the ultimate place to pitch, connect, and secure funding. And we’ve got an AI Demo Stage running all day, every day this year, right in the heart of Annual. 100+ scale-ups and start-ups showing you how they do it!

VP of Engineering 177

VP of Engineering CTO Coach VPCs (Virtual Private Cloud) Scale 177

SaaStr

OCTOBER 31, 2023

Dear SaaStr: What Did You Learn From Your Worst Venture Capital Investment? You can’t keep investing in the same companies, at the exact same stage, same valuations, etc. When I’ve cut a corner here and invested in startups with customers that aren’t super-happy, it hasn’t worked out as well. But the NPS/CSAT has to be there.

Venture Capital 273

Venture Capital Investment CTO Churn 273

SaaStr

JULY 18, 2022

Co-founder and CEO of Plato, Quong Hoang, the #1 mentoring platform for engineering leaders , helped moderate a discussion between CTO of Change.org, Elaine Zhou, and Head of Engineering at Notion, Michael Manapat, on this subject. As a company, you need to invest as much in your employee’s personal growth as they do.

CTO Coach 273

CTO Coach CTO Hire New CTO Engineering 273

SaaStr

MARCH 16, 2022

Jenn Knight, Co-founder and CTO of AgentSync, and Daryna Kulya, Co-founder of OpenPhone, discuss how different approaches have helped each brand reach its target audience and accomplish its goals, the potential of product-led growth, and how to scale growth strategies to yield desirable results. tip their toes in new growth strategies.

New CTO 246

New CTO CTO Scale Innovation 246

SaaStr

MAY 26, 2023

Dan Robinson, current Advisor and former CTO at Heap , shares five essential learnings from nearly a decade of building a SaaS business. What Your Job Is (And What It Isn’t) Your Job is to Make the Company Win A CTO may imagine their primary job is to provide technical expertise, lead engineers, and help build the product.

CTO Coach 240

CTO Coach CTO Hire CTO Leadership 240

SaaStr

MAY 18, 2025

” Adobe Sign / EchoSign once “failed the due diligence” on a potential sale because their CTO was perceived as not strong enough (despite later becoming a chief scientist at Adobe) “You’re being interviewed and the bet is on the people” 6.

Technical Review 155

Technical Review CTO Hire CTO Sales Hiring 155

SaaStr

NOVEMBER 17, 2023

I’ve come to almost exclusively invest in founder-CEOs that are engineers. Or at least where the co-founder CTO is a true equal partner to the CEO. Unless again, you have a true CTO as well, that is also leading the company. But usually there is an amazing CTO from Day 1. I look at the 25+ seed investments I’ve done.

Outsourcing Services 293

Outsourcing Services Engineering CTO Scale 293

USIO

JUNE 9, 2025

If you’re a CTO, architect, or lead dev navigating this decision, you’re in the right place. Side-by-Side: PayFac vs PayFac-as-a-Service ️ Let’s Talk Tech: What the CTO Cares About 1. Going full PayFac can be more profitable— if you hit significant scale and have the capital to invest upfront.

Payment Services 130

Payment Services Merchant Services PayFac as a Service SaaS Payments 130

SaaStr

MAY 20, 2020

He joined StubHub as CTO, but didn’t get nearly as much equity as the other CTO — because he “wasn’t committed enough.” They wanted to invest in apps, not APIs. He went to $125,000,000 in value — all stock — for his start-up to … $0 in 18 months. But a few investors got it.

CTO Hire 355

CTO Hire New CTO CTO Airlines 355

SaaStr

AUGUST 11, 2024

As a reminder, the SaaStr Fund is investing $170,000,000 in seed and late-seed investments. Algolia and Legacy Investment Talkdesk in BVP Cloud 100! At SaaStr Annual in September , their CTO will present all the hard data on how it actually works. A big week at SaaStr Fund! Some great news this week: #1. We led the U.S.

Cloud 300

Cloud AI Generative AI CTO 300

SaaStr

JANUARY 4, 2022

Invest in customers for life. CEO and co-founder Bill Magnuson was CTO until 2017, then took over as CEO from a co-founder, and owns 4.5%. I love to see a CTO become CEO, and founders pass the baton to each other when it works. That’s a challenge to everyone that says customer growth has to slow at scale. more today.

New CTO 69

New CTO CTO Software Review B2B 69

SaaStr

NOVEMBER 16, 2021

David Sacks: SaaS Background and Investments. David Sacks has invested in over 20 unicorn companies, including Airbnb, Bird, ClickUp, Facebook, Slack, and Uber. David considers product to be its own department that should also report directly to the CEO, instead of falling under the CTO. CTO (40 Employees). Team Size: 12.

CTO Hire 284

CTO Hire Sales Hiring Sales Recruiting CTO 284

SaaStr

FEBRUARY 1, 2022

I’ve come to almost exclusively invest in founder-CEOs that are or were engineers. Or at least — where the co-founder CTO is a true equal partner to the CEO. But usually there is an amazing (in terms of cleverness, if not always pure skillset) CTO from Day 1. I look at the 25+ seed investments I’ve done.

Outsourcing Services 256

Outsourcing Services Engineering CTO SaaS 256

SaaStr

FEBRUARY 8, 2021

” — Jason Riedel, founder/CTO of Aspireship. “When customers get back $100k’s in minutes and want to pay us more” — Kanat Bekt, founder/CTO, SupplyPike. Received 6 unsolicited angel investment offers from ordinary people. “When we had 1 in 5 people using our products across cafes.

CTO Hire 344

CTO Hire New CTO CTO Healthcare 344

TechEmpower SaaS

OCTOBER 9, 2023

It gives stakeholders an opportunity to assess the benefits and challenges before making additional investment on iterative improvements. cto , infotech , innovation , product , project , saas However, you often get a 70% solution pretty quickly through a Proof of Concept - and it’s often already better than the existing search.

AI Search 519

AI Search Artificial Intelligence Generative AI AI 519

SaaStr

JULY 30, 2022

But say this to a VC, and that’s not a sign of founders they want to invest in for the next 5–10 years. “We Our CTO is leaving.” We need the money to get sales and marketing going.” While logical, again, this isn’t what VCs want to hear. Not jump start it. Important to know.

CTO 336

CTO Engineering Startup Revenue 336

SaaStr

JULY 24, 2022

Personally, I’ve made about 30 VC investments (see SaaStrFund.com), 6 of them unicorns, and 0 CEOs have been fired. However, perhaps more importantly, the 2 CEOs I’ve invested in that have decided to bring on an outside CEO, in both cases with the encouragement of the board. That’s when they can fire you.

Technical Cofounder 284

Technical Cofounder Venture Capital Startup CTO 284

SaaStr

JANUARY 5, 2021

What makes a bad CTO? What types of due diligence are undertaken by VCs before investing in a company? As a CTO in a startup, what should I do when the CEO wants to interfere with making technical decisions? He has met Adam Neumann for only 4 minutes and decided to invest $4.4 What should I do? How much does a VC make?

Software Review 293

Software Review CTO Coach Technical Review Sales Recruiting 293

SaaStr

JULY 21, 2020

Your investors and others will learn a lot more hearing about sales from your VP of Sales, your CTO co-founder … and not you. Just assume none of your investors invest again. Professional investors can even write off any given investment if they have to. All-hands meetings, board meetings, whenever. Yes, you are the CEO.

Sales Recruiting 363

Sales Recruiting New CTO Scale CTO 363

SaaStr

MARCH 5, 2023

I’ve invested in 5 start-ups that had a $1,000,000,000+ cash exit or IPO. Almost all of them had an amazing CTO or CPO, and hired a simply epic VP or two. Dear SaaStr: What Qualities Make a CEO The Best In Their Industry? The CEOs were all quite different. Some extroverted, some introverted. Some wicked smart, some merely very smart.

CTO Hire 281

CTO Hire CTO Investment Marketing 281

SaaStr

FEBRUARY 25, 2025

Including: CEO Snowflake CEO HubSpot CEO DropBox CEO Descript CEO Clio CEO Flock Safety CEO Own CRO ServiceTitan CMO Databricks CMO Infinite Reality CTO Rubrik CCO Canva CCO Bill CCO GitHub VP AI Wiz CEO Calendly and 100s more!! In addition, this year Mayfield is sponsoring our VC AI Pitch Stage and will invest from $500k-$5m in the winner!

Sales Recruiting 167

Sales Recruiting Scale CTO Hire Sales Hiring 167

SaaStr

MARCH 7, 2021

Less and you under-invest. At $8m in ARR, if you have $2m of cash in the bank, you get real nervous investing much more than $500k-$750k, $1m max. It’s subtle, but in SaaS I’ve learned you under-invest if you have < 50% of your ARR in the bank. 5/ Moving from CTO-led -> VPE-led dev team. More here.

Part-Time VPE 293

Part-Time VPE Sales Recruiting Sales Hiring Scale 293

SaaStr

JANUARY 27, 2024

My experience across leading 30+ seed investments, including 4 billion+ exits so far, on why startups fail: Not 200% committed to winning no matter what. There are other reasons startups something do “Good But Not Great” or just OK, but that don’t lead to failure IMHE: Great CEO, Merely Good CTO.

Startup 281

Startup Scale CTO Pricing 281

SaaStr

MAY 30, 2022

But it can blow up on you if the CTO has issues, or your co-founder is leaving, etc. 50% or more of each investment is in the team. Write your own investment memo. Forget the business plan, but instead, write a memo on why if you were a VC, you’d invest in your own company. Sometimes, they really will just invest Later.

CTO 312

CTO Investment Branding Churn 312

SaaStr

JUNE 25, 2023

A few that I’ve seen across the handful of investments I’ve made … that didn’t work out: Not really committed to going long. A great CTO usually can solve this problem just in time to save the customers, but without one, revenue stalls. What are some qualities of a bad startup CEO/founder in Silicon Valley?

Startup 258

Startup New CTO CTO Investment 258

Tom Tunguz

OCTOBER 28, 2024

On Monday, at TC Disrupt Colin Zima CEO of Omni , Jordan Tigani CEO of Motherduck , Daniel Svnova CEO of Superlinked & Toby Mao CTO of Tobiko Data who are leading the evolution of the Post Modern Data Stack discussed the trends they are seeing. Here are some of the themes & predictions from the group.

Trends 248

Trends Data New CTO CTO 248

SaaStr

FEBRUARY 7, 2023

Tips: to manage OKRs, and KPIs with ease with Kashinath Kadaba Shrish, Cofounder & CTO at Fitbots Leveraging new age AI technologies(GPT and NLP) to increase Organic Traffic using Scalenut with Saurabh Wadhawan, CoFounder at Scalenut What are the best marketing channels for SaaS B2B businesses?

VP of Engineering 293

VP of Engineering Technical Cofounder Outsourcing Services CTO Coach 293

TechEmpower SaaS

AUGUST 21, 2023

At TechEmpower, we’ve done over 50 technical reviews for budding startups, scaling enterprises, discerning investors, and ambitious companies seeking investment or acquisition. cto , infotech , innovation , product , project , saas Do I really know what’s going on under the hood?

Technical Review 390

Technical Review Software Review Development Team Review Systems Review 390

SaaStr

JANUARY 22, 2021

Ciara Peter (Gainsight VP of Product & Design) and Mickey Alon (CTO & Founder of Gainsight PX) share their practical tips for product leaders looking to achieve business growth. The return on marketing investment is much faster. What does it mean to make your product the star in your SaaS growth strategy?

Scale 284

Scale New CTO CTO Acquisition 284

SaaStr

NOVEMBER 19, 2020

Enough to invest, but not enough to go crazy with. No matter how great a hacker your CTO is. IME, rough order to make hires in: VPM: $0.2m ARR VPS: $1-$1.5m ARR VPCS: $2m ARR VPP: $3m-$4m ARR VPE: $5m-$6m ARR CFO: $10m ARR COO: $20m ARR. More here: [link]. — Jason BeKind Lemkin (@jasonlk) July 21, 2019. Wait longer?

Part-Time VPE 363

Part-Time VPE Sales Hiring CTO Hire Scale 363

SaaStr

MAY 19, 2023

Reference other great investments they’ve made, and why they are similar. Share up front why your first CTO left. And no one is in a rush today to invest. But hiding both doesn’t help. #3. Cold outreach and email does work but please, please slow it down and make it great. Truly hyper-personalize it. Share lots of details.

New CTO 300

New CTO CTO Banking Cloud 300

SaaStr

JANUARY 4, 2024

What’s your most recent disclosed investment? Jason Warner , who was CTO of GitHub before and during my time as COO there (and a former partner at Redpoint!) What’s your sweet spot for investing — check size, stage, type of deal? We are currently investing out of our 9th Early Stage fund, a $650M vehicle.

Management 273

Management CTO Hire New CTO CTO 273

SaaStr

DECEMBER 4, 2020

As the year starts to wind to a close, one exercise I go through with many CEOs I’ve invested in or am close to is this: Did you ship at least 3 truly game-changing features this year? What were they, and how did they truly move the needle? You’d be surprised if CEOs are being honest how many fail this test. Not just at $0.1m

New CTO 243

New CTO CTO Engineering Investment 243

SaaStr

SEPTEMBER 17, 2020

“Our journey with JFrog started back in November 2015 when I first met CEO and co-founder Shlomi Ben Haim and the JFrog team,” said Jai Das, who is the president and managing director at Sapphire Ventures , which participated in the $50 million Series C investment. “One But even more appealing was the product vision the founders outlined.

New CTO 258

New CTO CTO Benchmarks Consulting 258

Valerian Tech

DECEMBER 30, 2022

The role of a Fractional Chief Technology Officer (CTO) is to provide technical expertise and leadership to a company on a part-time or temporary basis. This can be a useful option for startups or small businesses that may not have the resources to hire a full-time CTO or may not need one on a permanent basis.

Fractional CTO 52

Fractional CTO CTO Hire Part-Time CTO CTO 52

BetterCloud

SEPTEMBER 6, 2019

Our new Chief Technology Officer (CTO) Andra Milender defected from a medical career track before finding her footing on a technology path. What does your role as the CTO entail? You wear all hats as CTO. The definition of CTO is so broad and that’s what I like about this role! Go Yankees!

Part-Time CTO 8

Part-Time CTO CTO New CTO Technology 8