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

DECEMBER 16, 2023

You really need a great CTO, not just a good business team. A mediocre tech team, a part-time CTO, or even just a decent CTO just doesn’t get you there. Wait until you find a great partner here. If you can’t do the time, don’t do the startup. It’s just too competitive today.

Part-Time VPE 295

Part-Time VPE CTO Hire Sales Recruiting VPCs (Virtual Private Cloud) 295

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

SaaStr

JANUARY 27, 2024

Dear SaaStr: What are some common reasons for the failure of startups? My experience across leading 30+ seed investments, including 4 billion+ exits so far, on why startups fail: Not 200% committed to winning no matter what. That might be OK for a few months, but beyond that, startups fall into a decay curve they don’t recover from.

Startup 282

Startup Scale CTO Pricing 282

SaaStr

APRIL 4, 2024

Dear SaaStr: I’m Being Recruited by a Startup That Just Raised $5m. I’d suggest a quick 2 part test: #1. Decide if the CEO is literally a 10/10 and ideally the CTO If you aren’t sure the CEO is truly great, and ideally, the CTO, then ask around. How Do I Vet Them? At least, usually. How Do I Pick Right?

Sales Recruiting 287

Sales Recruiting CTO Startup Sales 287

SaaStr

JANUARY 16, 2023

To convert an idea into a successful venture, startups need to be equipped to scale. 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. .

Scale 259

Scale CTO Hire Cloud Scaling 259

SaaStr

MAY 28, 2023

SaaStr 663: 9 Things I Wish I Would Have Told My 2013 Self: Lessons Learned from 9 Years with Heap’s Former CTO, Dan Robinson   3. SaaStr 660: CRO Confidential: 3 Secrets For Early-Stage Startups To Acquire Customers With CoSell.io Jack Altman, CEO of Lattice: Things You Think as A First-Time Founder That Just Ain’t So 2.

CTO 246

CTO Sales Recruiting Compensation Startup 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

APRIL 21, 2024

Dear SaaStr: What Are The Top 5 Things I Should Know Before Starting a SaaS Startup? Wait and find a co-founder just as committed as you are. If you’re a “business” founder, know it’s really, really hard to win without a truly great CTO. Everyone mentally budgets 10–12 months. It’s never enough.

Startup 307

Startup CTO SaaS Interviewing 307

SaaStr

NOVEMBER 17, 2023

Or at least where the co-founder CTO is a true equal partner to the CEO. You need to recruit a great engineering team. You’ve got to recruit a much bigger, and more expensive, engineering team in many cases. Unless again, you have a true CTO as well, that is also leading the company. But — Jobs had Woz.

Outsourcing Services 293

Outsourcing Services Engineering CTO Scale 293

SaaStr

APRIL 7, 2021

The first type is the kind of management team hired by second+ time founders. They often staff up their teams with folks they already know and have been successful with at their last startup. And if you are, you are going to naturally start off hiring up-and-comers to your first leadership team. And that’s great.

Part-Time VPE 284

Part-Time VPE Sales Hiring Sales Recruiting CTO Hire 284

SaaStr

SEPTEMBER 3, 2022

Dear SaaStr: What Are The Top Things to Know Before Starting a SaaS Startup? You have to find someone at least as good as you, ideally better. A mediocre “coder” CTO because you can’t code … won’t really work out. Venture capital is a niche type of funding and 99% of startups will never be able to raise venture capital.

Venture Capital 312

Venture Capital Startup CTO SaaS 312

SaaStr

AUGUST 9, 2022

Investments I've made that didn't work out: – Momentum investment – CEO a bit of bulls**t artist – CEO good at sales but weak product team / CTO. CEO good at sales, but CTO not that great. This was a bet I made a few times, and I learned. So now I try to only invest in Great CEO + Great CTO combos.

Investment 307

Investment Sales Recruiting CTO Startup 307

SaaStr

JULY 31, 2022

An updated classic SaaStr guide on how to know if that new VP you worked so hard to find, recruit and get on board … is really going to make it. 4 Signs You Might Have a “Bad” CTO — Or At Least, One That Isn’t Going to Make It. SaaStr 574: 5 Scale-Up Mistakes for Startups with Dave Kellogg.

New CTO 300

New CTO CTO SMB Venture Capital 300

SaaStr

MARCH 3, 2020

Brendon introduces his playbook to hiring the first VP of Sales from his experiences as VP of Sales at LinkedIn, EchoSign, Talkdesk and more. Learn the dos and don’ts to make the correct hire the first time and not rush into hiring the wrong VP of Sales, which can cost the company months or even years. Roughly 90%.

Sales Hiring 229

Sales Hiring Sales Recruiting CTO Hire Scale 229

SaaStr

OCTOBER 30, 2022

The Simple Reason Startups That Just Raised $100s of Millions Are Doing Layoffs. SaaStr 603: SaaStr CRO Confidential Presents the Ultimate Guide to Sales Compensation, Quotas and Recruiting with SaaStr CEO and Founder, Jason Lemkin. CRO Confidential: Sales Comp, Quotas & Recruiting with Jason Lemkin and Sam Blond of Founders Fund.

Sales Recruiting 301

Sales Recruiting CTO Compensation Software Review 301

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. Q: How Do You Get Sustainable Output In A Startup?

CTO Hire 242

CTO Hire Sales Recruiting Sales Hiring Scale 242

SaaStr

FEBRUARY 1, 2022

Or at least — where the co-founder CTO is a true equal partner to the CEO. You need to recruit a great engineering team. You need to pay up to recruit a “technical co-founder” and then she often will bring in 2x the engineers, at a higher price, than an engineer CEO. I’ve found that works equally well. How to be super agile.

Outsourcing Services 263

Outsourcing Services Engineering CTO SaaS 263

TechEmpower SaaS

DECEMBER 11, 2023

Although noteworthy, working with large corporations differs remarkably from working with startups. While the appearance matters, remember you are hiring the development firm primarily for its development skills, not its graphic design skills. cto , product , saas Are they publicly available? Either way, we can help!"]

Software Development 443

Software Development Development Software Review Software 443

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 102

SMB Sales Recruiting Branding Sales Hiring 102

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.” Jeff says he’s realized startups are either “product constrained or distribution constrained “ Make your investments accordingly.

CTO Hire 355

CTO Hire New CTO CTO Airlines 355

SaaStr

MARCH 5, 2023

Ode to the $100,000,000 Exit Dear SaaStr: Should You Hire Someone That Seems Good … But Always Job Hops? SaaStr 636: Extreme Product Design: Building Things People Actually Use with Stripe CTO David Singleton  5. SaaStr CRO Confidential: Brex GM of Startups Lucas Fox on Customer Retention and Expansion 2. TAM is Great.

Scale 246

Scale Sales Hiring CTO Hire Startup 246

SaaStr

JANUARY 5, 2021

It’s been a fun experience being on Quora for … a decade We’ve crossed 60,000,000 views of our answers there, so let’s take a look at the Top 50 most viewed SaaStr Answers on Quora in 2020: Why do many startup owners sell their firm and move on instead of planning on making it a big player like Google, Microsoft, etc.?

Software Review 293

Software Review CTO Coach Technical Review Sales Recruiting 293

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 284

Scale Sales Hiring Sales Recruiting AI 284

SaaStr

JULY 5, 2019

For me, it took a while to build up the experiences and confidence to get there: First, I worked with enough startups and CEOs to “get it”. I had a chance as a startup lawyer working in “Silicon Valley” to work with 20+ startups. Second, I joined the best startup that would have me, as a Director and then Senior Director.

Part-Time VPE 206

Part-Time VPE Fractional VPE CTO Hire Sales Recruiting 206

SaaStr

JULY 28, 2021

One of the most popular sessions at SaaStr Annual, Busting the Myths About Startup Success with BlackLine CEO and Founder Therese Tucker is up at the top of our must-watch list. I retired from SunGard Treasury Systems as their CTO. We see that guy all the time down in LA. Don’t be that guy with your startup.

Startup 284

Startup CTO Hire Sales Hiring CTO Coach 284

TechEmpower SaaS

AUGUST 21, 2023

It provides findings and recommendations intended to foster a mutual understanding between business and software leaders, shedding light on the current state of your technology and your team. Outgrowing your stack: Your tech stack was just right for your startup. Your tech team is suggesting a costly, time-consuming overhaul.

Technical Review 390

Technical Review Software Review Development Team Review Systems Review 390

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. SaaStr 567: Classic Episode: eCommerce API Startup to Unicorn With Shippo Co-Founder and CEO Laura Behrens Wu.

CTO Hire 258

CTO Hire Sales Hiring CTO Scale 258

SaaStr

JANUARY 12, 2022

Indeed this was also my #1 mistake and the #1 I see from so many startups learning to go upmarket. You have to be careful to pair that with someone strong to manage the relationship, that has more time and that also can be trusted. As a founder, you’ll just run out of time to properly manage key customers and partners yourself.

CTO Hire 325

CTO Hire Sales Hiring New CTO CTO 325

SaaStr

JUNE 18, 2023

Answers from the CEOs of Twilio, Veeva, Amplitude, HubSpot, Gainsight and More What Your First 100 Hires Will Look Like Top Podcasts This Week: 1. SaaStr 666: Scaling a SaaS Startup to $1B+ ARR: Insights from UiPath’s CEO and Founder Daniel Dines  2.

CTO Hire 246

CTO Hire New CTO CTO Startup 246

SaaStr

JULY 5, 2024

GTM Mistake #1: A VP of Sales That Can’t Sell or Demo the Product Mistake number one has always been an issue, and it’s the number one reason startups struggle in today’s world. 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. Or why you lose?

CTO Hire 209

CTO Hire Sales Hiring New CTO Venture Capital 209

SaaStr

AUGUST 25, 2023

To some extent, if you have the hottest startup in the world, the full package, you can play some games with investors. 99% of startups aren’t that. For 99% of startups, when you want money, tell VCs you want money. 2 “Give the VP of Sales more time.” Hiring someone too junior. Ask for money when you want advice.”

Part-Time VPE 242

Part-Time VPE Scale Sales Hiring CTO Hire 242

Intercom, Inc.

FEBRUARY 28, 2018

That means we’ll be hiring 350 people over the next 18 months across our offices in San Francisco, Dublin, London, Chicago and Sydney. Her most recent startup, where she was CEO, was sold to Airbnb, and Ann then went on to work closely with Brian Chesky and Joe Gebbia in a role where she led development for all new products at Airbnb.

Scale 195

Scale Sales Hiring CTO Engineering 195

SaaStr

JULY 10, 2021

Which role should you hire for first? For starters, your first hire should be someone who can complement your skills, someone who is strong in areas where you’re weak, but it goes much deeper than that. Obviously, I can’t imagine a chief executive not having loss of sleep over building a management team. Mallun : Sure.

Sales Hiring 261

Sales Hiring Underperforming Technical Team Development Team Review CTO Hire 261

SaaStr

FEBRUARY 7, 2023

The goal is to help each other learn something new, find mentorships, create partnerships, and exchange strategies. Straight from a SaaS CCO with Yellow.ai’s CCO with Shekar Murthy, Chief Customer Officer at Yellow.ai with Yamini Jain, Co-founder at Global roots inc How to manage a SAAS startup effectively?

VP of Engineering 293

VP of Engineering Technical Cofounder Outsourcing Services CTO Coach 293

Scytale

MARCH 12, 2025

As the UKs tech startup ecosystem continues to thrive, visionary founders are driving innovation across various industries, shaping the future of technology , finance , healthcare , and beyond. In this article, we highlight the top 10 tech startup founders in the UK for 2025 (who you should be following if you arent already!),

Startup 59

Startup Scale Cybersecurity AI Search 59

SaaStr

AUGUST 18, 2019

Not hiring a good enough CTO. A bit more here: 15+ of The Top Sales & Marketing Mistakes SaaS Startups Make | SaaStr. The post What are the biggest mistakes first-time startup founders make, and how can they be avoided? Even if you don’t like sales, or big companies, or whatever. The most agile teams win.

Growth Hacking 154

Growth Hacking CTO Hire Startup Sales Hiring 154