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

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. You can’t build a whole new product, but you can tweak what you have. ” A good reminder to us all.

CTO Hire 355

CTO Hire New CTO CTO Airlines 355

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. These webinars will also be great training for the new folks.

Scale 348

Scale CTO Hire Sales Hiring New CTO 348

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

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

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. Random or persistent bugs: “The menu bar has been fixed three times now!” It also provides concrete recommendations for improvements.

Technical Review 390

Technical Review Software Review Development Team Review Systems Review 390

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

MAY 10, 2023

Combining Strong Growth With A New Level of Efficiency. 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. 45% of Customers Now Use 3 or More HubSpot Products.

Scale 325

Scale SMB Headcount New CTO 325

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 have to try new things. You see this all the time.

Part-Time VPE 290

Part-Time VPE Sales Hiring CTO Hire Scale 290

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

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. You’re not building a product or getting any new customers. You can’t hire a magician Head of Product.

Scale 290

Scale Sales Hiring Sales Recruiting AI 290

SaaStr

FEBRUARY 7, 2023

The goal is to help each other learn something new, find mentorships, create partnerships, and exchange strategies. with Aashish Krishna Kumar, Head of GTM at Togai Sales Enablement 2.0 – Elevate Rep Performance with Divanshu Goyal, Sales at GTM Buddy Common scaling pains for SaaS businesses and how to overcome them.

VP of Engineering 298

VP of Engineering Technical Cofounder Outsourcing Services CTO Coach 298

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

JANUARY 4, 2024

“Doubling Down” is a new series where we hear from top B2B SaaS investors on their most recent activities and takes on the current market. Jason Warner , who was CTO of GitHub before and during my time as COO there (and a former partner at Redpoint!) Check that out here. What’s your most recent disclosed investment?

Management 278

Management CTO Hire New CTO CTO 278

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

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

OCTOBER 28, 2019

Though our second day of the event is focused on mythical creatures of all kinds, you’ll find that there are unicorns hiding in our agenda every day this year. Well, we did the heavy lifting and highlighted a few here for you… Marianna Tessel, Intuit CTO + Cathy Polinsky, Stitch Fix CTO + Robin Ducot, Survey Monkey CTO.

New CTO 113

New CTO CTO Scale Engineering 113

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 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. Soon after, new teams started building a lot of new features and services, and they assumed full on call responsibilities. Finding the right on call process. The history of on call at Intercom.

Engineering 209

Engineering Software Review Technical Review Systems Review 209

SaaStr

FEBRUARY 25, 2020

So even the freshest new SaaS startup celebrating their 50th customer may find themselves dealing with sales tax in multiple states. . hiring in-house talent). The last thing you want is to make the news because a state comes at you for unpaid sales tax. Leverage automation to support scaling.

Merchant Services 207

Merchant Services Scale Technical Review Sales Hiring 207

SaaStr

NOVEMBER 21, 2019

Since 2010 we’ve seen more startups, funds, and capital than ever before, but with this drastic increase, investors are seeing unexpected new trends reshaping the future of the industry. The panel that we are in is called Is Seed the New Series A, and this is a question that I’ve been asking informally yesterday and today.

New CTO 182

New CTO Sales Hiring B2C CTO Hire 182

Intercom, Inc.

FEBRUARY 16, 2022

We identified some “ known unknowns” too; problems we needed to solve, but didn’t know how just yet – like integrating the new region into our billing system. We were reluctant to make changes of that scale and slow down our R&D teams (in the middle of a pandemic!), That meant moving fast, despite the scale of the project.

Scale 234

Scale New CTO Engineering CTO 234

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

SaaStr

JANUARY 14, 2020

What sets apart some of the most successful, high-growth companies we see today—Slack, Dropbox, Atlassian—has been their ability to tap into and master a new GTM strategy: B2C2B. We saw inside the company this tension between our classroom business and this new B2C digital business, and we knew we had to make a decision.

B2B 173

B2B B2C Scale New CTO 173

BetterCloud

SEPTEMBER 6, 2019

Our new Chief Technology Officer (CTO) Andra Milender defected from a medical career track before finding her footing on a technology path. She’s looking forward to helping BetterCloud scale and become one of the most reliable solutions that customers use. You wear all hats as CTO.

Part-Time CTO 8

Part-Time CTO CTO New CTO Technology 8

Intercom, Inc.

OCTOBER 31, 2019

The next generation of workforce will want and expect the next generation of technology. Outdated and misapplied technologies are ill-suited to the tasks at hand, which creates trouble for the humans using it. By retiring technologies proactively , you can remain focused on consistently moving the needle. Calendars are broken.

Artificial Intelligence 169

Artificial Intelligence Scale CTO Hire Technology 169

Tom Tunguz

OCTOBER 24, 2021

Great to see a lot of repeat attendees and some new ones. We’re excited to continue the Month of Scale here for Redpoint Office Hours. A thanks to [Marsh 00:00:34] for stepping in at the beginning of the month, and a great session with our own Jason Warner and Adrian, the CTO of Zendesk. I’m Travis Bryant.

CTO Coach 164

CTO Coach Sales Hiring Sales Recruiting CTO Hire 164

Tom Tunguz

NOVEMBER 18, 2015

Last night, SaaS Office Hours hosted Optimizely co-founder and CTO Pete Koomen. First, hire a management coach to work with you as the company grows. The best ways he found to learn leadership skills was to hire a management coach to meet him once per month, to talk through the issues facing him at Optimizely.

CTO Coach 113

CTO Coach Sales Hiring CTO Hire Startup 113

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. You have the opportunity to upsell new features and capabilities to them.

Outsourced Development 214

Outsourced Development Underperforming Technical Team Development Part-Time VPE 214

Panintelligence

JUNE 7, 2024

In this blog, we asked Panintelligence CEO Zandra Moore and CTO Ken Miller what they think are some of the most frequent mistakes in SaaS development and offer actionable insights to help you steer clear of them. But keeping what you’ve got is as important as bringing in new customers. Recruit on your cultural values.

CTO Hire 98

CTO Hire SaaS Business Underperforming Technical Team 98

SaaStr

SEPTEMBER 18, 2020

You can watch the full session , and if you missed the podcast with the first half of the interview, you’ll find that here. If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin. We might’ve touched on this one too on the hiring and the people.

Sales Hiring 246

Sales Hiring CTO Hire Scale Investment 246

SaaStr

NOVEMBER 11, 2019

Though our second day of the event is focused on mythical creatures of all kinds, you’ll find that there are unicorns hiding in our agenda every day this year. Well, we did the heavy lifting and highlighted a few here for you… “When to Hire and When to Automate” with Zapier CEO Wade Foster. Check it out below!

Payment Services 113

Payment Services CTO Hire Payments New CTO 113

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. Again, we felt that there was much greater value in being authentic than trying to be someone that we weren’t and try to find positives. We had no New York city presence.

CTO Hire 178

CTO Hire Travel Underperforming Technical Team CTO Coach 178

Intercom, Inc.

JULY 21, 2022

What started as a series of interviews by co-founder Des Traynor soon bloomed into hundreds of episodes where we explore how businesses are driving growth through customer relationships and how to build successful products at scale. For Slack, that was clearly the engineering and dev communities, who love new tools.

Outsourcing Services 215

Outsourcing Services Sales Hiring CTO Hire Acquisition 215

Scytale

MARCH 12, 2025

As the co-founder and CEO of leading fintech company, OakNorth , – valued at over 1 billion – he has revolutionized lending for scale-up businesses through advanced data analytics, providing fast, flexible financing solutions for SMEs. Will Donnelly Will Donnelly is a passionate entrepreneur tackling the eldercare industry.

Startup 59

Startup Scale Cybersecurity AI Search 59

Sales Hacker

SEPTEMBER 29, 2020

Keys to success when scaling a company [10:56]. Major challenges facing a new CEO [19:40]. How to find advisors when you’re a CEO [22:32]. Vishal Sunak: We are on the scale to eight digits right now, not that far away. So yeah, we’re five years old and scaling to eight digits and beyond now.

Scale 120

Scale CTO Hire CTO Coach Scaling 120

Intercom, Inc.

JUNE 14, 2018

I am the Vice President of Product at Business Talent Group, where we help find really good freelance jobs for high-end consultants at very large companies. I’m currently building a lot of internal tools to help folks do their jobs more efficiently—and to help them scale. Adam: You’ve also managed to write two books.

VP of Engineering 190

VP of Engineering Underperforming Technical Team CTO Coach New CTO 190