SaaStr

FEBRUARY 25, 2025

Unparalleled Networking Opportunities SaaStr Annual brings together thousands of SaaS, Cloud and AI executives, founders, VCs, and industry leaders under one roof across our 40+ acre campus, May 13-15 in SF Bay! Finding and recruiting top talent is consistently ranked as one of the biggest challenges for growing SaaS companies.

Sales Recruiting 193

Sales Recruiting Scale CTO Hire Sales Hiring 193

SaaStr

JUNE 23, 2025

The Talent Reckoning Here’s what I’ve learned from talking to 200+ SaaS founders over the past six months: The companies shipping great AI aren’t necessarily the ones with the biggest AI budgets or the fanciest ML infrastructure. Meanwhile, their competitors hired AI-native talent and shipped three product iterations.

AI Search 173

AI Search AI Technical Review CTO Hire 173

Scytale

OCTOBER 21, 2024

It’s particularly relevant for SaaS companies, cloud providers, and tech-based services that manage sensitive client data. Streamlining the Sales Process: Ever been knee-deep in contract negotiations when the client suddenly asks, “Are you SOC 2 certified?” Uh-oh, now what? For some, that’s an instant deal-breaker.

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.” Case Studies Learn best practices from our customers.

Scale 52

Scale Payment Solutions SaaS Payments Payments 52

SaaStr

JUNE 12, 2025

We’ve been saying for months that speed is the new moat in SaaS Sales with the advent of AI, and yeah, that’s still 100% true. It’s fundamentally rewired how SaaS sales works, period. These are the 5 ways AI has already changed SaaS sales forever. These aren’t just predictions anymore.

Scale 217

Scale AI Sales Hiring CTO Hire 217

SaaStr

JUNE 1, 2025

Every B2B and SaaS company now competes in a global, AI-enabled market from Day 1. The Kicker: ChatGPT’s daily usage increased 202% over 21 months, with users spending more time per session (47% longer) and having more sessions per day (106% more). For B2B and SaaS Leaders: The infrastructure layer is being rebuilt from scratch.

AI Search 262

AI Search AI CTO Hire ChatGPT 262

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

SaaStr

JANUARY 28, 2025

We were bought in part to help spark the SaaS and Cloud transition in one business unit — Document Cloud. Because they could build it, but that would take time. Salesforce bought an online wordprocessor for $750m … just to get its CTO. #2. Hire one 95% of the time. And it did that.

Technical Review 273

Technical Review CTO Hire CTO Cloud 273

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. At SaaStr, we’re obsessed with knowing how the best SaaS companies scale from zero to IPO and beyond.

Scale 193

Scale SMB Sales Hiring Scaling 193

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. Two SaaS Metrics That Actually Don’t Matter That Much in the Earliest Days: Absolute Churn and Sales Cycles. Late Stage VC is Kind of Frozen, Down at Least 40%.

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 Scale 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. In The End, The “Covid Boost” in SaaS Was a Bust. AngelList: Seed Rounds Have Fallen 50% in Volume Since March. They Quit You.

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

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. And SaaStr Europa brings 2,500+ SaaS execs, founders, and VCs together to Europe every summer. We were the first major SaaS event back in the SF Bay Area. SaaStr is turning 10!

Scale 307

Scale Sales Recruiting CTO Hire New CTO 307

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.

Part-Time VPE 352

Part-Time VPE Sales Hiring CTO Hire Sales Recruiting 352

SaaStr

JUNE 23, 2020

In SaaS, it is recruiting your VPs and management team : SaaS products mostly don’t sell themselves. SaaS products get too complex to hack a product roadmap too long. 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 309

Part-Time VPE CTO Hire Fractional VPE Sales Recruiting 309

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

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. SaaS products get too complex to hack a product roadmap too long. 95% of the time, your super-smart hacker co-founder is not that person.

Scale 274

Scale Part-Time VPE CTO Hire Fractional VPE 274

SaaStr

NOVEMBER 16, 2021

As your SaaS company grows and you go through various fundraising stages, your company size also grows. 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 Sacks: SaaS Background and Investments.

CTO Hire 284

CTO Hire Sales Hiring Sales Recruiting CTO 284

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

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. Not for start-ups.

Sales Hiring 257

Sales Hiring Part-Time VPE CTO Hire Sales Recruiting 257

SaaStr

MAY 26, 2023

You’ll never truly understand how to lead a SaaS company until you’ve done it firsthand. Dan Robinson, current Advisor and former CTO at Heap , shares five essential learnings from nearly a decade of building a SaaS business. Software is Fractal A SaaS product is richly nuanced and contains multiple layers.

CTO Coach 242

CTO Coach CTO Hire CTO Leadership 242

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. Dear SaaStr: How Many Sales Reps Do I Need? Top Videos This Week: 1.

CTO Hire 258

CTO Hire Sales Hiring CTO Scale 258

SaaStr

DECEMBER 10, 2020

I hear again and again from SaaS founders growing to $5m, $10m ARR or even more that they don’t need a certain VP — with the exception of a VP of Sales. Basically, in SaaS, everyone “gets” that they need a VP of Sales. Hire not just 1-2 reps, but 10. That it’s time to bring in someone that knows.

Sales Hiring 363

Sales Hiring CTO Hire Sales Recruiting Scale 363

SaaStr

FEBRUARY 8, 2021

Because as a SaaS founder especially, it can be hard to know. ” — Jason Riedel, founder/CTO of Aspireship. “When on New Year’s Eve, customers kept sending us signed contracts.” I recently asked on Twitter when folks knew their startup had something … great. 20% conversion.

CTO Hire 347

CTO Hire New CTO CTO Healthcare 347

SaaStr

JULY 5, 2024

They hire a VP of Sales who doesn’t want to sell or learn the product. You also don’t want to hire a VP of Sales who won’t carry a bag. If you joined a startup at $2M and wanted to get to $6M with reps doing $400k, that VP of Sales would need to hire ten reps. 90% of the time, sales falls when a founder steps out of it.

CTO Hire 209

CTO Hire Sales Hiring New CTO Venture Capital 209

SaaStr

JULY 13, 2023

Startups come in all shapes and sizes on various stages of a timeline, yet it’s not surprising how many have the same questions and concerns about how to scale from x to y to z, the right time to hire and fire, and how to keep a team motivated during hard times. His answers didn’t disappoint. They wanted a one-call close.

CTO Hire 242

CTO Hire Sales Recruiting Sales Hiring Scale 242

SaaStr

JUNE 18, 2023

Check out this week’s top blog posts, podcasts, and videos: Top Blog Posts This Week: About 70% of SaaS Public Companies Are New Versions of Existing Categories of Software (Updated) Growth Slowed Down About 33% On Average For Everyone in Q1 The Top 20 SaaStr Tips to Getting a SaaS Start-Up Going When Should You Add a Second Product?

CTO Hire 246

CTO Hire New CTO CTO Startup 246

SaaStr

MARCH 5, 2023

Check out this week’s top blog posts, podcasts, and videos: Top Blog Posts This Week: Does Anyone Want To Be a Unicorn Anymore? Ode to the $100,000,000 Exit Dear SaaStr: Should You Hire Someone That Seems Good … But Always Job Hops? TAM is Great. If So, How Much? Top Podcasts This Week: 1.

Scale 246

Scale Sales Hiring CTO Hire Startup 246

SaaStr

MARCH 7, 2021

These are all full-time jobs by $1m ARR. Fixing it yourself becomes the biggest time sink and excuse for not hiring there is. You end up spending all your time backfilling roles you should have hired. And even worse, you often sort of give up trying to make the hire. And hire against it. More here.

Part-Time VPE 293

Part-Time VPE Sales Recruiting Sales Hiring Scale 293

SaaStr

OCTOBER 29, 2021

There, Amplitude has become part of the core product stack for many SaaS and software leaders for product analytics. Use overages to renegotiate contracts, not charge per event. Folks come out differently here, but while Amplitude charges per volume, in part, it doesn’t make a material amount from overages.

Scale 307

Scale CTO Hire New CTO CTO 307

SaaStr

JANUARY 16, 2023

Hiring a reliable team is an all-encompassing issue where startups dive in head-first but fail to optimize it for success. . Hiring an expert produces 1000x better results than someone with interests elsewhere. . “A Hiring in a streamlined manner with a rigorous selection process initially builds momentum for long-term goals.

Scale 259

Scale CTO Hire Cloud Scaling 259

SaaStr

APRIL 7, 2021

The top SaaS companies grow faster than ever these days. The first type is the kind of management team hired by second+ time founders. Veterans of the SaaS journey. But most of us are first-time founders, or close to it. That CTO that doesn’t quite have the traditional background. More on that here ).

Part-Time VPE 282

Part-Time VPE Sales Hiring Sales Recruiting CTO Hire 282

SaaStr

NOVEMBER 29, 2020

They’ll revolt when you make a senior or mid-level hire that as a group, they simply cannot suffer one day longer. But I forced us to hire him, over my CTO’s strong objection and my VPE’s grudging acknowledgment we had no choice. It was a hire I wasn’t really in favor of, but it was an experiment.

Part-Time VPE 284

Part-Time VPE Sales Hiring CTO Hire Scale 284

SaaStr

OCTOBER 25, 2023

Each year, tens of thousands of SaaS fans attend SaaStr Annual. For part one of this Ask Me Anything session, Jason covers everything you need to know about hiring your first VP of Sales, what he really thinks about AI, what the future of lead generation in 2024 looks like, and much more. People don’t do that today.

Scale 284

Scale Sales Hiring Sales Recruiting AI 284

SaaStr

AUGUST 25, 2023

Hundreds of thousands of experts are telling you how to succeed in SaaS. SaaStr Founder and CEO Jason Lemkin shares the 10 worst pieces of SaaS advice, excuses, and mistakes founders make, and what to do instead You can’t always expect a great VP of Sales to double sales in 30-60-90 days. Hiring someone too junior. Yes, you do.

Part-Time VPE 242

Part-Time VPE Sales Hiring Scale CTO Hire 242