SaaStr

DECEMBER 7, 2024

The HubSpot co-founders, for example, had $100m exits the first time. As Dharmesh Shah co-founder and CTO notes in the SaaStr Annual deep dive below, the second time … they just really wanted to go big. (And most things in venture dont really work.) HubSpot was their second one. Today, its worth almost $40 Billion.

Venture Capital 274

Venture Capital New CTO CTO Product Marketing 274

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

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. Meet and Find Your Next VP / CXO!

Sales Recruiting 190

Sales Recruiting Scale CTO Hire Sales Hiring 190

SaaStr

APRIL 14, 2025

Whether youre looking for a co-founder, a mentor, or your next big customer, youll find them here. Find your next VP there! 1,000+ Networking Sessions Weve doubled down on networking opportunities, with over 1,000 sessions, including Braindates, AMAs, mentoring, and 1:1 meetings. Screenshot 6.

VP of Engineering 201

VP of Engineering CTO Coach VPCs (Virtual Private Cloud) Scale 201

FastSpring

FEBRUARY 6, 2025

If you’re running a smaller digital business, you may find it challenging to hire great talent. Larger technology companies can pay more, offer more benefits, and provide a more marketable brand on a candidate’s resume. Podcast Full Interview: Audio Listen online or find it on more podcast services.

SMB 107

SMB Sales Recruiting Branding Sales Hiring 107

SaaStr

JUNE 20, 2025

Business Intelligence & Analytics Threat: Real-time AI analysis vs. static dashboards Problem: Most BI tools still require human interpretation 4.

AI Search 289

AI Search Artificial Intelligence AI CTO Hire 289

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

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

Buffer Resources

SEPTEMBER 3, 2024

Tagging your partner organizations, influencers, or thought leaders at your company (your CEO, CTO, etc.)   To tag your brand, type “@yourcompanyname” A popup will appear, find the appropriate page or person, and click to tag.   For us, we have a cadence of sharing blog posts multiple times throughout the week.

Social Media 107

Social Media B2B Interviewing New CTO 107

SaaStr

DECEMBER 30, 2024

The numbers are strong, but the CTO isnt good enough. They waste a ton of time. I find them torture. They frustrate everyone and waste precious time. Not all the deals, but probably 80% of them. The Almosts. These are brutal as an investor and confusing for founders. Theres good stuff there, so its close.

Startup 261

Startup CTO Investment Marketing 261

BetterCloud

FEBRUARY 6, 2025

For instance, if new hires don’t request access to a particular tool, or if no new licenses have been acquired within a year, it may be an opportunity to discontinue that tool. Last month, IT Brews webinar focused on an all too common issue – rising software costs colliding with sprawling tech stacks.

CTO 52

CTO Cost optimization & reporting SaaS Operational efficiency. 52

Chart Mogul

OCTOBER 17, 2024

"Singular events can distort reality, but ChartMogul helps us see the bigger picture", says Patrick Craston, Intruder's CTO. Intruder provides ongoing monitoring to find security weaknesses in networks, websites, APIs, and cloud setups. What is Intruder? Their system helps businesses spot and fix security problems quickly.

Payment Solutions 52

Payment Solutions Payment Methods Payment Features Payments 52

Scytale

MARCH 12, 2025

As co-founder and CEO of Lottie , he has built a trusted platform that helps families easily navigate, find, and finance later-life care. Will Donnelly Will Donnelly is a passionate entrepreneur tackling the eldercare industry.

Startup 59

Startup Scale Cybersecurity AI Search 59

Scytale

APRIL 30, 2025

Without standardization, businesses could find themselves at risk of overlooking key aspects of AI ethics, privacy , or security. Scytale streamlined the process by providing expert-driven technology. They shared valuable insights about our security systems so we can better protect our customers data.

AI 52

AI Government compliance Artificial Intelligence 52

Scytale

OCTOBER 21, 2024

The time to audit completion will depend on the size and complexity of your organization. Once the audit is complete, you’ll receive a SOC 2 Attestation Report outlining the auditor’s findings. Scytale streamlined the process by providing expert-driven technology. If you meet all the requirements, congratulations!

Technical Review 52

Technical Review Scale compliance CTO Hire 52

SaaStr

JUNE 12, 2025

As Dmitry put it: “Instead of you having to always ask for the update of what’s happening with this account, we’re able to detect those changes that are meaningful and surface that to you.”

Scale 214

Scale AI Sales Hiring CTO Hire 214

SaaStr

JUNE 1, 2025

As Andrew Bosworth (Meta CTO) noted: “This is our space race…there’s very few secrets. ” Duolingo CEO Luis von Ahn (all-hands): “AI use will be part of what we look for in hiring. AI use will be part of what we evaluate in performance reviews. revenue (33x multiple) Anthropic: $61.5B

AI Search 259

AI Search AI CTO Hire ChatGPT 259

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. Companies using Datadog have reported significant improvements in issue resolution times – up to an 80% reduction.

Scale 52

Scale Payment Solutions SaaS Payments Payments 52

Scytale

DECEMBER 3, 2024

Penetration Testing Explained Imagine you hire someone to try to break into your business – not physically, but digitally. Cybercriminals are at the top of their game and they know just how to find those sweet spots. Scytale streamlined the process by providing expert-driven technology. Why Do You Need It?

compliance 52

compliance CTO Hire Technical Review Software Review 52

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

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

Scytale

FEBRUARY 10, 2025

This includes the cost of productivity to get (and stay) compliant and the practical requirements related to ISO 27001 compliance. Faster certification, reduced administrative burden, and a stronger security posture – all while keeping costs under control. Plus, our whole team is more security-aware now thanks to Scytale!

Systems Review 52

Systems Review Software Review CTO Hire compliance 52

SaaStr

JULY 17, 2025

No hiring developers. Without hiring a dev, coding myself, etc.? I just DM’d with a CTO that’s trying to do a similar project, he spend $4k in 2 weeks on Replit in max/max mode too. If I could even find anyone I trust to help me, and stick with it? “Just a quick prototype,” you tell yourself.

CTO Hire 256

CTO Hire Software Review New CTO Technical Review 256

Crafty CTO

JUNE 18, 2025

I think you can find a wide spectrum of very strongly held opinion that is all mutually contradictory. Kirschner dives a layer deeper into MCP, with great insights into how “early days” we are, and the basic primitives of the protocol. ” And guess what he announced for VS Code: full MCP spec support. .”

Engineering 52

Engineering AI Search AI Payment Solutions 52

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.

Scale 191

Scale SMB Sales Hiring Scaling 191

User Pilot

MARCH 30, 2025

Jose Gomez, CTO & Co-Founder at Evinex. Timely, contextual, and relevant messages can enhance the user experience and increase daily active users. Apps with solid ASO strategies achieve better user retention by making it easier for users to find them and understand their value quickly. Key elements of an app with good ASO.

Payment Solutions 52

Payment Solutions Retention Payment Methods Strategy 52

TechEmpower SaaS

AUGUST 7, 2023

What does it mean to be a CTO for a startup? Should a startup CTO spend their time programming? Exploring new technologies? The role of a CTO varies as the company matures. That’s why the CTO’s attention is on programming for the earliest stage. A CTO can help you find the right answers.

CTO Hire 390

CTO Hire New CTO CTO Fractional VPE 390

Crafty CTO

JULY 1, 2025

Finding the right crossbar for the Forester’s low-profile rails would have been a nightmare in Google, and even likely to trip up a smart one-shot model LLM GPT-4o. But o3 thought hard, using every bit of context I gave it, such as photos of the low-profile rails, and recommended solutions that checked out as accurate.

ChatGPT 52

ChatGPT Artificial Intelligence Pricing 52

SaaStr

JULY 2, 2020

Q: 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. So … a “bad” CTO is one that can’t recruit a strong “pizza box” team.

Part-Time VPE 361

Part-Time VPE CTO Engineering Scaling 361

Sales Hacker

FEBRUARY 18, 2025

Previously, he was an operating partner at Fractal Software, helping launch vertical software companies and find product-market fit. If you missed GTM 134, check it out here: Build your AI Outbound Machine with ChatGPT | Jordan Crawford Highlights: 05:03 When to hire your first sales reps. What does Joe look like at that time?

Sales Hiring 98

Sales Hiring CTO Hire Scale VP of Engineering 98

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

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

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

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

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 19, 2022

SaaStr 564: Top 10 Learnings Architecting a High Throughput Critical API with RevenueCat CTO Miguel Carranza. SaaStr 565: Classic Episode: The Importance of Company Values, a Great Hiring Process, and Ownership Culture with Gusto Co-Founder & CEO Josh Reeves. Product-Led Growth: Panacea or Boondoggle?

CTO Hire 290

CTO Hire CTO Sales Hiring Innovation 290

TechEmpower SaaS

MARCH 4, 2024

The shift towards AI-driven ad technologies enables brands to set and achieve highly specific engagement KPIs, moving away from generic strategies to more personalized, data-driven approaches that resonate with their target audience. This not only speeds up hiring but also lowers the costs associated with lengthy recruitment cycles.

Generative AI 443

Generative AI CTO Hire AI Sales Recruiting 443