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 23, 2020

Q: What’s the number one challenge for scale-up founders? You will need a VP of Product to scale your roadmap. You can smother customers with love alone in the early days, but as you scale, you need a seasoned customer success team and VP that has done this before. She can be your CTO forever.

Part-Time VPE 310

Part-Time VPE CTO Hire Fractional VPE Sales Recruiting 310

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

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. SaaStr began in 2012 as a simple WordPress blog and a few answers on Quora sharing Jason Lemkin’s learnings of going from $0 to $100m ARR at EchoSign. SaaStr is turning 10!

Scale 307

Scale Sales Recruiting CTO Hire New CTO 307

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. . Build an irreplaceable team .

Scale 259

Scale CTO Hire Cloud Scaling 259

TechEmpower SaaS

DECEMBER 11, 2023

Do you anticipate scale issues presently or in the future? 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.

Software Development 443

Software Development Development Software Review Software 443

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 at scale, people will use your API in crazy ways that you might not imagine, so some margin of the unexpected is unavoidable.

CTO Hire 246

CTO Hire New CTO CTO Scaling 246

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. ” Times of crisis are actually great times to find hard problems to solve.

CTO Hire 355

CTO Hire New CTO CTO Airlines 355

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

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. Without training, reps 3-10 scale more slowly, if at all. And they see the CEO sort of judging them for not scaling quickly. Simplify to a 1 page contract. They get CEO training.

Scale 348

Scale CTO Hire Sales Hiring New CTO 348

SaaStr

FEBRUARY 15, 2023

Scaling a PLG company While it’s great to figure out a PLG model that allows you to scale your revenue with inbound, it cannot stop there. Outbound fury is about getting customer attention through tactics like viral tweets, fun videos, controversial blog posts, and a constant presence in the media.

Scale 244

Scale Sales Hiring CTO Hire Scaling 244

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. Register for SaaStr Annual and join 12,500 Cloud and SaaS Founders, VCs, and Execs at SaaStr Annual for three full days of workshops, sessions, and networking — all to help you scale faster.

CTO Coach 242

CTO Coach CTO Hire CTO Leadership 242

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. At that point, VPEs need them to scale. Why join a start-up? Not for start-ups.

Sales Hiring 257

Sales Hiring Part-Time VPE CTO Hire Sales Recruiting 257

SaaStr

FEBRUARY 25, 2025

Our 10th Annual Meet-a-VC program to opt-in ahead of time, to set up VC-Founder matchmaking, Note: the above programs are only for Cloud / SaaS / AI founders and executives. Speakers share their playbooks on everything from achieving product-market fit to optimizing CAC:LTV ratios and scaling go-to-market strategies.

Sales Recruiting 195

Sales Recruiting Scale CTO Hire Sales Hiring 195

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. with Jenn Knight, Co-founder and CTO of AgentSync, and Daryna Kulya, Co-founder of OpenPhone.

CTO Hire 258

CTO Hire Sales Hiring CTO Scale 258

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. Top Podcasts This Week: 1. SaaStr APAC 2023: Stage A Streaming LIVE 5.

Scale 246

Scale Sales Hiring CTO Hire Startup 246

SaaStr

OCTOBER 29, 2021

Some leaders like Slack have seen the same, but most Cloud leaders at scale with high NRR end up getting more and more of their revenue from their existing base, not new customers. Use overages to renegotiate contracts, not charge per event. They’re growing even faster at scale. More on that here.

Scale 307

Scale CTO Hire New CTO CTO 307

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

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. It was magical to have an A+ team member also be almost 100% scaled up his first day. Especially in tougher times, folks may be knocking on your door again. Roundtrip hires can work. Life changes.

CTO Hire 322

CTO Hire CTO Scaling Management 322

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? David considers product to be its own department that should also report directly to the CEO, instead of falling under the CTO. CTO (40 Employees).

CTO Hire 284

CTO Hire Sales Hiring Sales Recruiting CTO 284

SaaStr

DECEMBER 10, 2020

in ARR, get to Initial Traction , we then realize we have to scale. 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. My CTO and dev team is building all the features we need.

Sales Hiring 363

Sales Hiring CTO Hire Sales Recruiting Scale 363

SaaStr

JUNE 12, 2022

Check out this week’s top blog posts, podcasts, and videos: Top Blog Posts This Week: What All First-Time CEOs Should Know About Fundraising. SaaStr 559: Secrets to Building Your Marketing Engine To Drive Scale with Airtable CMO Archana Agrawal. 5 Interesting Learnings from Zoom at $4.3B Top Videos This Week: 1.

Scale 237

Scale Sales Hiring CTO Hire CTO 237

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. Get on a jet, at least twice a quarter.

Part-Time VPE 293

Part-Time VPE Sales Recruiting Sales Hiring Scale 293

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. Then, they can scale almost infinitely. And that’s great.

Part-Time VPE 284

Part-Time VPE Sales Hiring Sales Recruiting CTO Hire 284

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. He was literally the only person on the planet with the specific scaling experience we needed. It did work — we got the scaling done. You see this all the time. Everyone hated him.

Part-Time VPE 284

Part-Time VPE Sales Hiring CTO Hire Scale 284

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 I’ve almost failed every time.”

CTO Hire 242

CTO Hire Sales Recruiting Sales Hiring Scale 242

SaaStr

AUGUST 20, 2023

The best we made our CTO. But what if our CTO gets hit by a bus? He scaled up our technology in a way folks for years had thought was impossible. They feed on each other, hire other toxic people, and turn the company against the mission and each other. Sometimes, still hire them. Well he was toxic. For a while.

CTO Hire 246

CTO Hire CTO Technology Engineering 246

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

DECEMBER 23, 2019

From large scale mainstage sessions to intimate workshops and even a dedicated lounge, we are carving out some of SaaStr Annual just for developers and engineers. ” When to Hire and When to Automate” with Zapier CEO Wade Foster. ” When to Hire and When to Automate” with Zapier CEO Wade Foster.

CTO Coach 188

CTO Coach Engineering CTO Hire Development 188

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. I am guessing it’s probably the hardest problem to solve, hiring a job, let alone at this level. And for good reason.

Sales Hiring 261

Sales Hiring Underperforming Technical Team Development Team Review CTO Hire 261

SaaStr

JANUARY 4, 2024

Jason Warner , who was CTO of GitHub before and during my time as COO there (and a former partner at Redpoint!) All of our Managing Directors on the early team have both founded companies and operate at scale. This week we’re focusing on Erica Brescia, Managing Director at Redpoint Ventures! #1. Why did you do the deal?

Management 273

Management CTO Hire New CTO CTO 273

SaaStr

DECEMBER 20, 2023

In that case, is PLG cheaper for expanding the base than their sales-driven process? “I think it’s both if you look at scale,” Henry says. “PLG is cheaper, right? It can’t come from scaling something five years ago from 10 to 400 SDRs, but real innovation.

New CTO 312

New CTO Scale Sales Hiring AWS 312

SaaStr

AUGUST 25, 2023

On top of that, founders are full of excuses preventing them from scaling. You have to see: A couple of good hires brought in Improvement on some metrics A big deal or two hanging out there, brought in and closed Things taken off your plate. But after a couple million in ARR, you can afford any hire if they’re accretive.

Part-Time VPE 242

Part-Time VPE Sales Hiring Scale CTO Hire 242

Intercom, Inc.

APRIL 19, 2018

Rich Archbold , Senior Director of Engineering, has been at the forefront of codifying and scaling this philosophy over the past few years. The concept was the foundation for his popular talk and ultimately his classic, long-form blog post. Ciaran, our CTO , came up with this magical line. Recodifying Run Less Software at scale.

Outsourcing Services 192

Outsourcing Services Part-Time VPE Software AWS 192

SaaStr

JUNE 1, 2021

Co-founder and CTO Dharmesh Shah shared with us how they got there — and the top mistakes they made — just 3 quarters after their IPO. We have someone that probably 98 percent of you know virtually or socially in some sense, Dharmesh Shah, founder and CTO of HubSpot. It got much better over time. A SaaStr Classic!!

Part-Time VPE 290

Part-Time VPE Technical Cofounder CTO Hire New CTO 290

SaaStr

OCTOBER 24, 2022

WorkOS CEO Michael Grinich, Developer Success Manager Betsy Calender, and VP of Developer Experience Zeno Rocha share how to price your product for developers, how to market it to developers, how to how to support them as they scale and use the products. The contract size grows. Doing Business with Developers.

Outsourced Development 210

Outsourced Development Underperforming Technical Team Development Part-Time VPE 210

SaaStr

APRIL 16, 2019

Learn how Pendo built a product, team, and culture in its Raleigh hometown that could scale coast-to-coast and continent-to-continent. You can read blog posts, tweets about why you shouldn’t try to create a company outside the Bay area. We ended up signing that contract in the uber back to the airport on the way home.

CTO Hire 177

CTO Hire Travel Underperforming Technical Team CTO Coach 177