SaaStr

MARCH 1, 2024

Dear SaaStr: What’s The Number One Challenge for Scale-Up Stage Founders? 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 will need a VP of Product to scale your roadmap.

Scale 279

Scale Part-Time VPE CTO Hire Fractional VPE 279

SaaStr

JUNE 23, 2020

Q: What’s the number one challenge for scale-up founders? 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. You will need a VP of Product to scale your roadmap.

Part-Time VPE 311

Part-Time VPE CTO Hire Fractional VPE Sales Recruiting 311

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

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

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

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

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 263

Scale CTO Hire Cloud Scaling 263

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 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

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

TechEmpower SaaS

DECEMBER 11, 2023

Do you anticipate scale issues presently or in the future? Are specific technologies or platforms involved in your project? While the appearance matters, remember you are hiring the development firm primarily for its development skills, not its graphic design skills. cto , product , saas Or is your project a clean slate?

Software Development 443

Software Development Development Software Review Software 443

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

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

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 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. 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 323

CTO Hire CTO Scaling Management 323

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?

CTO Hire 242

CTO Hire Sales Recruiting Sales Hiring Scale 242

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 290

Part-Time VPE Sales Hiring CTO Hire Scale 290

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. It starts at the beginning when someone interacts with your brand.” – Kim Walsh Hiring and collaboration for growth The product marketing team is the first function to hire for.

Scale 244

Scale Sales Hiring CTO Hire Scaling 244

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? He scaled up our technology in a way folks for years had thought was impossible. You find a way, or at least come close, to fill the gap.

CTO Hire 246

CTO Hire CTO Technology Engineering 246

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

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 14, 2022

Many teams got to come together and meet each other in person for the first time. Founders were able to recruit on-site. Fast forward to today, and there is an amazing amount of B2B-centric content out there, and many others have put together amazing events around the hard-learned lessons of scaling revenue and scaling SaaS companies.

Scale 312

Scale Sales Recruiting CTO Hire New CTO 312

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

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 638: Lessons Learned in Scaling Your Team & Revenue from $1M ARR to $1B+ with Cloudflare CRO Chris Merritt  2. SaaStr 639: Scaling a SaaS Sales Team While Building Culture with Figma VP of Sales Scott Pugh   3.

Scale 246

Scale Sales Hiring CTO Hire Startup 246

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. LIVE from SaaStr Europa 2023: Stage A – Tuesday 4.

CTO Hire 246

CTO Hire New CTO CTO Startup 246

SaaStr

JUNE 12, 2022

SaaStr 559: Secrets to Building Your Marketing Engine To Drive Scale with Airtable CMO Archana Agrawal. Top 5 Mistakes Building & Scaling Global Product Teams | HubSpot GM & VP, Products Poorvi Shrivastav. with Jenn Knight, Co-founder and CTO of AgentSync, and Daryna Kulya, Co-founder of OpenPhone.

Scale 237

Scale Sales Hiring CTO Hire CTO 237

Valerian Tech

JANUARY 5, 2023

It can be beneficial to hire a fractional CTO (Chief Technology Officer) in a variety of situations. When you don't have an in-house technology leader: If you don't have a CTO or a similar technology leader on your team, a fractional CTO can fill that role.

Fractional CTO 52

Fractional CTO CTO Hire Part-Time CTO CTO 52

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 191

CTO Coach Engineering CTO Hire Development 191

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 264

Sales Hiring Underperforming Technical Team Development Team Review CTO Hire 264

TurnKey Labs

MARCH 6, 2023

The fact is, not every company needs a Chief Technology Officer. Knowing how to hire a CTO is one thing—knowing when to hire a CTO is another. If […]

CTO 57

CTO CTO Hire Technology Scaling 57

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 Scale Sales Hiring CTO Hire 242

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 278

Management CTO Hire New CTO CTO 278

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 316

New CTO Scale Sales Hiring CTO Hire 316

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. You’ll find out tomorrow.

Part-Time VPE 296

Part-Time VPE Technical Cofounder CTO Hire New CTO 296

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. Our chat covers the origins of Run Less Software, how it has evolved at scale, and how it differs from the equally valid approaches of other engineering teams.

Outsourcing Services 192

Outsourcing Services Part-Time VPE Software AWS 192

Intercom, Inc.

APRIL 27, 2018

Back in the early days of Intercom, our CTO Ciaran was the entirety of the on call team, both in and out of the office. This felt natural at the time, as it was a lightweight way to scale our on call team and was consistent with our values that emphasized the importance of ownership. Finding the right on call process.

Engineering 209

Engineering Software Review Technical Review Systems Review 209