SaaStr

JULY 16, 2025

Even if you’ve hired someone to do it? When they launched a huge new feature customers were demanding, the CTO not only built it himself — but launched it in person at 10 customers. Here’s why it’s not just okay, but often necessary … at times: 1. Yes, absolutely. Flew out, set it up, and managed the launch.

CTO Hire 203

CTO Hire New CTO Sales Hiring CTO 203

SaaStr

JULY 22, 2025

A CTO can point to technical debt reduction or infrastructure improvements. Their scoreboard is updated in real-time. Plus, boards generally give CEOs more time to execute their vision, especially if they’re founders or were hired with a clear mandate for transformation. Hire for quick ramp time.

Part-Time CTO 203

Part-Time CTO CTO Sales Hiring CTO Hire 203

SaaStr

MAY 18, 2025

Big Company M&A Is Incredibly Complex “Acquiring a company is a much bigger deal for a tech company than you think” “The soft costs are much, much more than the cash or stock” Integration can consume “10,000 hours of like expensive people’s time” 2.

Technical Review 176

Technical Review CTO Hire CTO Sales Hiring 176

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!! Investor Connections and Funding Opportunities — And $5m AI VC Pitch Stage!!

Sales Recruiting 190

Sales Recruiting Scale CTO Hire Sales Hiring 190

SaaStr

JUNE 23, 2025

The CTO who said “we don’t need AI people, our engineers can figure it out “ is now 12 months behind companies that hired AI-native talent in early 2024. Meanwhile, their competitors hired AI-native talent and shipped three product iterations. Hire for AI-first thinking, not AI expertise.

AI Search 172

AI Search AI Technical Review CTO Hire 172

Teamgate

JUNE 11, 2025

Sarah Kim, CTO at GrowthCraft, highlighted the cost efficiency: “As our system grew to hundreds of services, our previous monitoring solution became prohibitively expensive. Uptrace offers all the features we need at a fraction of the cost.” Case Studies Learn best practices from our customers.

Scale 52

Scale Payment Solutions SaaS Payments Payments 52

Scytale

OCTOBER 21, 2024

Streamlining the Sales Process: Ever been knee-deep in contract negotiations when the client suddenly asks, “Are you SOC 2 certified?” Yaron Lavi CTO at Deel Book a Demo Unlocking Business Opportunities with SOC 2 Certification Now that you’ve put in the hard work to become SOC 2 certified, it’s time to reap the rewards.

Technical Review 52

Technical Review Scale compliance CTO Hire 52

SaaStr

JUNE 1, 2025

China Is Playing a Different Game Entirely The Models Youve Barely Heard Of: DeepSeek R1: 93% performance of OpenAI’s o3-mini at fraction of training cost Alibaba Qwen 2.5-Max: As Andrew Bosworth (Meta CTO) noted: “This is our space race…there’s very few secrets. 80% cheaper than predecessor, costs 0.2%

AI Search 259

AI Search AI CTO Hire ChatGPT 259

SaaStr

JUNE 12, 2025

” His real-world example is that when he gets a contract to review as the CBO of Perplexity in a buying role, he doesn’t immediately send it straight to legal anymore.

Scale 214

Scale AI Sales Hiring CTO Hire 214

SaaStr

JANUARY 9, 2025

Every time I see a CRO that doesn't sell themselves, they fail. Every time I see a CTO that doesn't code themselves, they fail. Every time I see a CMO that doesn't market themselves, they fail. We’ve spend the most time on hiring a great first VP of Sales, but all the VPs are super important.

Part-Time VPE 307

Part-Time VPE Sales Hiring CTO Hire Scale 307

Scytale

DECEMBER 3, 2024

Penetration Testing Explained Imagine you hire someone to try to break into your business – not physically, but digitally. If penetration testing is like hiring a hacker to test your defenses against security threats, then a compliance audit is like inviting an official inspector to verify whether you’re playing by the rules.

compliance 52

compliance CTO Hire Technical Review Software Review 52

Scytale

FEBRUARY 10, 2025

By integrating automation into your compliance strategy, your business can achieve and maintain ISO 27001 compliance at a fraction of the cost and in significantly less time. This includes the cost of productivity to get (and stay) compliant and the practical requirements related to ISO 27001 compliance. The result?

Systems Review 52

Systems Review Software Review CTO Hire compliance 52

SaaStr

JANUARY 28, 2025

Because they could build it, but that would take time. Salesforce bought an online wordprocessor for $750m … just to get its CTO. #2. Hire an M&A Banker: Their expertise and negotiation skills can prevent costly rookie mistakes. Hire one 95% of the time. Or in smaller deals, it’s often the team.

Technical Review 272

Technical Review CTO Hire CTO Cloud 272

Crafty CTO

JUNE 10, 2025

First, my book of business on the fractional CTO side of things filled up completely, reducing available writing time. Thinking back on it, I see two causes. Second, the AI emergence , like Solomon Epstein’s ill-fated space yacht in The Expanse , just kept accelerating.

AI 40

AI Artificial Intelligence CTO Hire ChatGPT 40

TechEmpower SaaS

AUGUST 7, 2023

What does it mean to be a CTO for a startup? Should a startup CTO spend their time programming? The role of a CTO varies as the company matures. Here’s a graphic from Socal CTO that illustrates the roles as they change over time: In its earliest days, a startup’s top need is often to produce a product.

CTO Hire 390

CTO Hire New CTO CTO Fractional VPE 390

SaaStr

MARCH 30, 2025

Co-founders Dharmesh Shah (CTO) and Brian Halligan (Chairperson) shared at SaaStr Annual the unfiltered truth on building an SMB powerhouse, pivoting to product-led growth, and why the “M” segment is SaaS gold. The company had to retrench and restart their global efforts multiple times. Focus obsessively on churn.

Scale 191

Scale SMB Sales Hiring Scaling 191

SaaStr

JUNE 19, 2022

Check out this week’s top blog posts, podcasts, and videos: Top Blog Posts This Week: 5 Interesting Learnings from Sprout Social at $240,000,000 in ARR. SaaStr 564: Top 10 Learnings Architecting a High Throughput Critical API with RevenueCat CTO Miguel Carranza. Product-Led Growth: Panacea or Boondoggle?

CTO Hire 290

CTO Hire CTO Sales Hiring Innovation 290

SaaStr

NOVEMBER 19, 2020

IME, rough order to make hires in: VPM: $0.2m He asked which to hire first. If you have a few nickels in the bank, and you somehow find a great VP a half stage or even full stage early, just hire her. Hiring is so hard as it is. Make the hire now. ARR VPS: $1-$1.5m More here: [link].

Part-Time VPE 364

Part-Time VPE Sales Hiring CTO Hire Sales Recruiting 364

SaaStr

JUNE 26, 2022

Check out this week’s top blog posts, podcasts, and videos: Top Blog Posts This Week: Be Careful Hiring “Dualies” — Folks That Are a VP of More Than One Thing. SaaStr 564: Top 10 Learnings Architecting a High Throughput Critical API with RevenueCat CTO Miguel Carranza. appeared first on SaaStr.

CTO Hire 290

CTO Hire CTO Sales Hiring Scale 290

SaaStr

JANUARY 19, 2022

Dear SaaStr: What Makes a Bad CTO? While there is no legal definition for CTO or bright line between CTO and VPE, I’d suggest a start-up CTO really only has to do a few things — which are very hard: Assemble a small team (3–9) of very good engineers. That often were never anticipated and aren’t part of the job spec.

CTO Hire 292

CTO Hire Part-Time VPE CTO Engineering 292

SaaStr

SEPTEMBER 10, 2020

Perhaps the single most important thing you can ever do in SaaS, at least after $1m in ARR or so, is hire the best VPs you can. We’ve talked a lot over the years about how not to hire a wrong VP of Sales — 70%+ of the first VPs of Sales don’t make it even 10 months. You need to hire up-and-comers. Get on jets?

Part-Time VPE 352

Part-Time VPE Sales Hiring CTO Hire Sales Recruiting 352

SaaStr

AUGUST 31, 2023

Dear SaaStr: How does a First Time Founder Identify 10x Hires? How do you hire a great CTO, a great VP of Product, a great VP of Sales … if you’ve never worked with one? There’s a reason almost every founder you talk to had a mis-hire for their first head of sales. It’s hard.

Sales Hiring 287

Sales Hiring CTO Hire CTO Coach CTO 287

SaaStr

JUNE 23, 2020

Or churn will increase, NPS will stagnate and decline, and upsell and revenue retention will be a fraction of what it could be. 95% of the time, your super-smart hacker co-founder is not that person. She can be your CTO forever. That’s a different, and critical, job than CTO. Marketing is also an art and science.

Part-Time VPE 308

Part-Time VPE CTO Hire Fractional VPE Sales Recruiting 308

SaaStr

FEBRUARY 22, 2023

Many companies believe excellent product design comes from hiring the best engineers and signing up for the latest software instead of building from the users’ perspectives. Stripe’s CTO, David Singleton, shares how they use a system of feedback, iteration, and fast shipping to create products that meet users’ expectations.

CTO Hire 292

CTO Hire CTO Payment Methods Payment Solutions 292

SaaStr

JULY 14, 2022

What started as a simple WordPress blog in 2012 has now become the world’s largest community of SaaS executives, founders, and entrepreneurs. SaaStr began in 2012 as a simple WordPress blog and a few answers on Quora sharing Jason Lemkin’s learnings of going from $0 to $100m ARR at EchoSign. SaaStr is turning 10! Now a staple!)

Scale 307

Scale Sales Recruiting CTO Hire New CTO 307

SaaStr

JANUARY 19, 2024

He made many great leadership points, but one in particular rattles around my head a lot and I think deserves its own post: You usually won’t know if you’ve made a 10x hire … when you make the hire. A good / great employee can become 10x in a new environment was part of Auren’s point. But I didn’t know they were truly 10x hires.

Sales Hiring 295

Sales Hiring CTO Hire New CTO CTO 295

SaaStr

MARCH 1, 2024

Or churn will increase, NPS will stagnate and decline, and upsell and revenue retention will be a fraction of what it could be. 95% of the time, your super-smart hacker co-founder is not that person. She can be your CTO forever. That’s a different, and critical, job than CTO. Marketing is also an art and science.

Scale 274

Scale Part-Time VPE CTO Hire Fractional VPE 274

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.” If your customers love your product now, hire reps. ” Times of crisis are actually great times to find hard problems to solve.

CTO Hire 355

CTO Hire New CTO CTO Airlines 355

TechEmpower SaaS

DECEMBER 11, 2023

While the appearance matters, remember you are hiring the development firm primarily for its development skills, not its graphic design skills. Our blog post 53 Questions Developers Should Ask Innovators has a list of questions any good development team would ask. cto , product , saas Either way, we can help!"]

Software Development 443

Software Development Development Software Review Software 443

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. Focus on retaining your engineers from day one. More like this at 2022 SaaStr Annual, Sep 13-15 in SF Bay Area!!

CTO Coach 273

CTO Coach CTO Hire New CTO Engineering 273

SaaStr

JUNE 16, 2022

Miguel Carranza, CTO at RevenueCat, shares ten learnings from firsthand experience in architecting an API & SDK that is currently on 5,000+ apps and has seen 3x growth Year-over-Year. . Instead, the CTO suggests that you avoid adding new pieces of infrastructure until absolutely necessary. What makes a great API?

CTO Hire 246

CTO Hire New CTO CTO Scaling 246

SaaStr

OCTOBER 9, 2020

Anyhow the one thing I learned, beyond getting help screening and hiring for these positions from domain experts, is to look for Flags. For signs the prospective hire just won’t work out, no matter how strong they might look on paper. Why join a start-up? Well reason #1 is personal and career advancement.

Sales Hiring 257

Sales Hiring Part-Time VPE CTO Hire Sales Recruiting 257

SaaStr

SEPTEMBER 11, 2021

Lately I’ve been working with 5+ SaaS companies all hiring their first VP of Product. And critically, most have a really strong CEO-CTO partnership. A few general learnings: A VP of Product that Reports to CTO / Engineering Rarely Meets With That Many Customers. I just see this time and time again.

Part-Time VPE 318

Part-Time VPE Outsourcing Services CTO Hire CTO 318

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 242

CTO Coach CTO Hire CTO Leadership 242

SaaStr

FEBRUARY 15, 2021

The first 2 scaled reps you hire that hit plan (some may churn before then) get special training. They get CTO training. And so we see reps 3-10, or reps-from-#3-until-The-VP-of-Sales-is-Hired … fail. Simplify to a 1 page contract. And the others perform so poorly vs. the 2 that are doing well? So what can you do?

Scale 348

Scale CTO Hire Sales Hiring New CTO 348

SaaStr

NOVEMBER 16, 2021

You’ll need to hire aggressively to get to the next level and continue that rapid growth. But what roles should you hire for, and what will your org chart look like at each stage? 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).

CTO Hire 284

CTO Hire Sales Hiring Sales Recruiting CTO 284

SaaStr

JULY 3, 2022

Check out this week’s top blog posts, podcasts, and videos: Top Blog Posts This Week: Zendesk and Anaplan: A Tale of Two Very Similar, And Very Different, $10B SaaS Acquisitions. The Ultimate Guide for Hiring a Great VP of Sales. with Jenn Knight, Co-founder and CTO of AgentSync, and Daryna Kulya, Co-founder of OpenPhone.

CTO Hire 258

CTO Hire Sales Hiring CTO Scale 258