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 276

Scale Part-Time VPE CTO Hire Fractional VPE 276

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 295

CTO Hire CTO Payment Methods Payment Solutions 295

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 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 310

Part-Time VPE CTO Hire Fractional VPE Sales Recruiting 310

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 320

Part-Time VPE Outsourcing Services CTO Hire CTO 320

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 293

CTO Hire CTO Sales Hiring Scale 293

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 261

Scale CTO Hire Cloud Scaling 261

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 258

Sales Hiring Part-Time VPE CTO Hire Sales Recruiting 258

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

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 287

CTO Hire Sales Hiring Sales Recruiting CTO 287

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

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 296

Outsourcing Services Engineering CTO Scale 296

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

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 303

New CTO CTO SMB Venture Capital 303

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

AUGUST 9, 2023

I should have camped in his office and literally never taken No for an answer. I had a great CTO, but I also needed a truly great VPE to scale past $10m ARR and deal with all those issues. Not finding a way to work through team conflicts better. Our CTO was amazing, but we didn’t work together as well as we should of.

Part-Time VPE 246

Part-Time VPE Sales Recruiting CTO Scale 246

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 296

Part-Time VPE Sales Recruiting Sales Hiring Scale 296

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

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

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. And the others perform so poorly vs. the 2 that are doing well?

Scale 348

Scale CTO Hire Sales Hiring New CTO 348

SaaStr

JANUARY 27, 2024

There are other reasons startups something do “Good But Not Great” or just OK, but that don’t lead to failure IMHE: Great CEO, Merely Good CTO. Can’t Recruit a Great VP Team / Only Able to Recruit Mediocre VPs. Some founders can do a lot on their own with a small team, but just never recruit great VPs.

Startup 285

Startup Scale CTO Pricing 285

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

MARCH 16, 2022

Jenn Knight, Co-founder and CTO of AgentSync, and Daryna Kulya, Co-founder of OpenPhone, discuss how different approaches have helped each brand reach its target audience and accomplish its goals, the potential of product-led growth, and how to scale growth strategies to yield desirable results. The Power of PLG.

New CTO 246

New CTO CTO Scale Innovation 246

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

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 106

SMB Sales Recruiting Branding Sales Hiring 106

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 310

Scale Sales Recruiting CTO Hire New CTO 310

SaaStr

JULY 21, 2020

But everyone hears from you all the time. Your investors and others will learn a lot more hearing about sales from your VP of Sales, your CTO co-founder … and not you. Regularly Ask Your Investors How Happy They Are on a Scale of 1-10. Spend more time with her or him. All-hands meetings, board meetings, whenever.

Sales Recruiting 363

Sales Recruiting New CTO Scale CTO 363

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

JUNE 27, 2019

Erica has led New Relic through massive growth, scaling the company’s enterprise business 10x since she joined the business pre-IPO. Erica will share the five critical steps (and some lessons learned along the way) for scaling in the enterprise. We operate at great scale. Hire builders who are experienced, strategic, and agile.

Scale 239

Scale Enterprise Scaling Sales Hiring 239

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 287

Scale Sales Hiring Sales Recruiting AI 287

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

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. This part of the report can go deep on how your software stacks up with respect to feature delivery, security, reliability, and scalability.

Technical Review 390

Technical Review Software Review Development Team Review Systems Review 390

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 287

Part-Time VPE Sales Hiring CTO Hire Scale 287

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 260

CTO Hire Sales Hiring CTO Scale 260

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

MAY 10, 2023

HubSpot’s operating margins have scaled into the double-digits the past two quarters for the first time. A reminder of just how important being multi-product is at scale. We did a deep dive here with CTO Dharmesh Shah a little while back: And a few other interesting learnings: #6.

Scale 324

Scale SMB Headcount New CTO 324

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