SaaStr

JUNE 20, 2025

Customer Service Platforms Threat: Voice agents indistinguishable from humans handling phone-based jobs at a fraction of human cost Market size: $85 billion addressable market for business calls alone 3.

AI Search 289

AI Search Artificial Intelligence AI CTO Hire 289

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

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

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

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?” 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.

Technical Review 52

Technical Review Scale compliance CTO Hire 52

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.” FAQs What should I consider when selecting an API monitoring tool for my business?

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

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

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

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

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

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

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

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

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

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

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

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

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

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 565: Classic Episode: The Importance of Company Values, a Great Hiring Process, and Ownership Culture with Gusto Co-Founder & CEO Josh Reeves.

CTO Hire 290

CTO Hire CTO Sales Hiring Scale 290

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

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

SaaStr

JUNE 23, 2020

In SaaS, it is recruiting your VPs and management team : SaaS products mostly don’t sell themselves. You can hack managing and finding 1–3 reps yourself, but after that, you really need a VP of Sales. Or churn will increase, NPS will stagnate and decline, and upsell and revenue retention will be a fraction of what it could be.

Part-Time VPE 308

Part-Time VPE CTO Hire Fractional VPE Sales Recruiting 308

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

In SaaS, once you have even a few million in ARR, the #1 challenge is recruiting top-tier VPs and building a truly top-tier management team: SaaS products mostly don’t sell themselves. You can hack managing and finding 1–3 reps yourself, but after that, you really need a VP of Sales. She can be your CTO forever.

Scale 274

Scale Part-Time VPE CTO Hire Fractional VPE 274

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

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. On a purely human level, most employees like to settle down if they find a place that feels like home.

CTO Coach 273

CTO Coach CTO Hire New CTO Engineering 273

SaaStr

OCTOBER 9, 2020

I don’t know about you, but I’ve had to recruit a lot of types of folks over the years where my domain knowledge was limited. I’ve had to recruit Ph.Ds. Anyhow the one thing I learned, beyond getting help screening and hiring for these positions from domain experts, is to look for Flags. Why join a start-up?

Sales Hiring 257

Sales Hiring Part-Time VPE CTO Hire Sales Recruiting 257

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. . But the reality is that when you’re trying to find product-market fit, that probably shouldn’t be your concern.” What makes a great API?

CTO Hire 246

CTO Hire New CTO CTO Scaling 246

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? You can find the full slide deck from David’s presentation on Slideshare. Positions Needed: FP&A Analyst, Accountant, HR, Ops, Recruiter.

CTO Hire 284

CTO Hire Sales Hiring Sales Recruiting CTO 284

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. 10. “Your job as an entrepreneur is to find hard problems to solve.” ” A good reminder to us all.

CTO Hire 355

CTO Hire New CTO CTO Airlines 355

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

DECEMBER 10, 2020

Hire not just 1-2 reps, but 10. That it’s time to bring in someone that knows. But I’ve found many great SaaS founders take longer, too long, to decide to hire the other VPs. But I’ve found many great SaaS founders take longer, too long, to decide to hire the other VPs. I Need a VP of Sales.

Sales Hiring 363

Sales Hiring CTO Hire Sales Recruiting Scale 363

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. cto , product , saas Quality of Work: The end product should not only look good but function as expected. Don't be charmed by an impressive aesthetic at the expense of functional results.

Software Development 443

Software Development Development Software Review Software 443