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 295

CTO Hire CTO Sales Hiring Innovation 295

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 292

Sales Hiring CTO Hire CTO Coach CTO 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 298

CTO Hire CTO Payment Methods Payment Solutions 298

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 296

CTO Hire CTO Sales Hiring Scale 296

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 311

Part-Time VPE CTO Hire Fractional VPE Sales Recruiting 311

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 301

Sales Hiring CTO Hire New CTO CTO 301

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 279

Scale Part-Time VPE CTO Hire Fractional VPE 279

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 321

Part-Time VPE Outsourcing Services CTO Hire CTO 321

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 278

CTO Coach CTO Hire New CTO Engineering 278

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 195

Sales Recruiting Scale CTO Hire Sales Hiring 195

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 259

Sales Hiring Part-Time VPE CTO Hire Sales Recruiting 259

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 290

CTO Hire Sales Hiring Sales Recruiting CTO 290

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

SaaStr

APRIL 7, 2021

The first type is the kind of management team hired by second+ time founders. And if you are, you are going to naturally start off hiring up-and-comers to your first leadership team. That CTO that doesn’t quite have the traditional background. There are roughly 2 types of start-up management teams.

Part-Time VPE 285

Part-Time VPE Sales Hiring Sales Recruiting CTO Hire 285

SaaStr

APRIL 28, 2020

In fact, right after that we hired a roundtrip employee as our CTO in my first start-up and it was amazing. Especially in tougher times, folks may be knocking on your door again. First, what doesn’t work, or at least hasn’t for me, is re-hiring: Folks that left for a company that was a better fit.

CTO Hire 323

CTO Hire CTO Scaling Management 323

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. Usually, this is sort of solved when you find a strong first VP of Sales. 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.

Scale 348

Scale CTO Hire Sales Hiring New CTO 348

SaaStr

MARCH 7, 2021

I thought it would be worth drilling down deeper into each of them, and sharing the learnings and mistakes: 1/ Spending less time fixing things, more time recruiting senior folks to own them. No one spends enough time recruiting as it is, after $1m ARR or so. These are all full-time jobs by $1m ARR.

Part-Time VPE 299

Part-Time VPE Sales Recruiting Sales Hiring Scale 299

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. But how do you find the pirates and romantics? It’ll fail.

CTO Hire 242

CTO Hire Sales Recruiting Sales Hiring Scale 242

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 263

Scale CTO Hire Cloud Scaling 263

SaaStr

FEBRUARY 27, 2020

It is a prerequisite to hire folks with a high IQ to success in software. You probably need a wicked smart CTO, some incredible engineers, maybe an insanely smart head of product or marketing, etc. But if you can recruit people smarter than you … which is a superpower … then that works, too.

CTO Hire 227

CTO Hire CTO Engineering Software 227

SaaStr

JULY 30, 2020

I’ve been reminded of this question in several meetings lately where founders are doing pretty well, getting to and past Initial Traction, but with hindsight it’s interesting that the founder that took the CEO gig perhaps was better suited to a different role, say CTO or SVP of Sales or President or COO or SVP Product.

Sales Recruiting 328

Sales Recruiting Venture Capital CTO Hire CTO 328

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 211

CTO Hire Sales Hiring New CTO Venture Capital 211

SaaStr

MARCH 5, 2023

Almost all of them had an amazing CTO or CPO, and hired a simply epic VP or two. Good but not great CEOs just can’t find a way to iterate fast enough. But what made them great: Ability to attract amazing co-founders and execs. Not just great, but epic. Ability to iterate pretty darn quickly. Not overnight. But eventually.

CTO Hire 288

CTO Hire CTO Investment Marketing 288

Tom Tunguz

AUGUST 14, 2024

Kevin Scott, CTO of Microsoft, framed the opportunity in AI this way : work on problems that used to be impossible, but are now really hard. Nearly 10 years ago, I wrote a post about the minimum viable average contract value to justify a sales team. Imagine a product offerd at a $10k contract value sold by an AE.

CTO Hire 223

CTO Hire Outsourced Development Sales Hiring CTO 223

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

JULY 5, 2019

But I started to learn what it took to recruit, inspire, and yes fail a team. When the time came when I found some white space, an opportunity to start a company, there was no way I could have done it without a co-founder better than me. And I learned to recruit. To hire our CTO, our first VPE, etc.

Part-Time VPE 208

Part-Time VPE Fractional VPE CTO Hire Sales Recruiting 208

SaaStr

AUGUST 20, 2023

In my first start-up, there were literally only a handful of engineers who understood our technology. The best we made our CTO. But what if our CTO gets hit by a bus? They feed on each other, hire other toxic people, and turn the company against the mission and each other. Sometimes, still hire them. For a while.

CTO Hire 246

CTO Hire CTO Technology Engineering 246

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 290

Part-Time VPE Sales Hiring CTO Hire Scale 290

SaaStr

JULY 3, 2022

The Ultimate Guide for Hiring a Great VP of Sales. Top Podcasts This Week: SaaStr 568: Mind the Gap: Balancing Growth and Efficiency in Tougher Times with Point Nine Managing Partner Christoph Janz. Balancing Growth and Efficiency in Tougher Times | Point Nine Managing Partner Christoph Janz. Top Videos This Week: 1.

CTO Hire 261

CTO Hire Sales Hiring CTO Scale 261

SaaStr

OCTOBER 25, 2023

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. There are no Cloud magicians, and you can’t hire a PLG magician. Let’s jump right into the questions.

Scale 290

Scale Sales Hiring Sales Recruiting AI 290

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. Technology staff management: A fractional CTO is responsible for managing the technology team, including hiring, training, and motivating employees.

Fractional CTO 52

Fractional CTO CTO Hire Part-Time CTO CTO 52