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 265

Sales Hiring Underperforming Technical Team Development Team Review CTO Hire 265

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. You will fail if you: 1) try to build a suite of products out of the gate, 2) focus solely on SMBs, or 3) have an MBA. But of course, it wasn’t always quite that big!

Part-Time VPE 297

Part-Time VPE Technical Cofounder CTO Hire New CTO 297

SaaStr

JUNE 26, 2024

Deals are contracting, not because of layoffs, but because people are managing budgets so tightly. It Takes Time To Bounce Back Jason was the first investor in RevenueCat , a company that automates mobile subscriptions on your phone. Or Scale AI securing $1B. They’re very SMB and just closed their first $750k TCV deal.

CTO Hire 148

CTO Hire AI Venture Capital Sales Hiring 148

SaaStr

SEPTEMBER 18, 2020

Immediately told them to hire 50 reps in a different city, in a different city, and they did. The CEO was deferential because that was 10 times what he’d ever raised before, and did all of it. Jason Lemkin: 50 reps in a new city that you’ve never met, and hired in 60 days when you’re in the low millions ARR.

Sales Hiring 246

Sales Hiring CTO Hire Scale Investment 246

SaaStr

SEPTEMBER 26, 2019

So up to 100-150K and SMB, we’re at 2K. And actually when we started, I see one face in the room that I recognize, Kurt Freytag, was one of our big customers at the time when I joined. So you were the first sales hire. So my first sales hire was beginning of 2015. So over time, don’t hire resumes necessarily.

Scale 150

Scale Sales Hiring Sales Recruiting Technical Advisors 150

Sales Hacker

JANUARY 21, 2020

SMB Sales & SDRs at (Smaller) Scale [18:20]. Today’s sponsor is Outreach , the leading sales engagement platform that enables sales reps to humanize their communications at scale, from automating the soul-sucking manual work that eats up selling time to providing action-oriented tips on what communications are working best.

Payment Methods 63

Payment Methods Scale CTO Coach SMB 63

ChurnZero

DECEMBER 9, 2022

More and more people are hiring leaders, not for past experience, but for capability and capacity. We hire a third-party firm. Q: FranConnect has customers of all sizes, from emerging and growing to scaling and enterprise. We had to say: what does SMB want? They’ve got a proven concept they need to scale.

CTO Coach 52

CTO Coach Customer Success VP of Engineering CTO Hire 52

Mucker Capital

APRIL 6, 2023

Obviously if you target enterprise customers, you usually have a very large ACV (Annual Contract Value) and the product usually is complex. We talk about using the product complexity, your target customer size, your contract value, and whether there's individual use case–those four things--to help you decide if PLG is a fit.

Startup 52

Startup Scale CTO Hire Outsourced Development 52

SaaStr

MARCH 12, 2019

How can founders know when is the right time to make the move from SMB to enterprise? Where does Erica often see founders make mistakes with this scaling? With the scaling of departments and teams, what has Erica seen work really well when it comes to making cross-functional teams communicate really well?

Scale 214

Scale Enterprise Scaling Sales Hiring 214

SaaStr

AUGUST 15, 2020

I mean, maybe you do, but I don’t know anyone right now with extra money, time, or people, right? And well, that simplicity theme obviously is so massive and also just doing more in the product when you have that massive scale that you all have at Algolia and New Relic has as well. From contract signature to launch.

Payment Methods 274

Payment Methods Merchant Services Scale Payments 274

SaaStr

DECEMBER 3, 2020

What was Sam’s biggest lesson from scaling the sales team at Dropbox? When is the right time to hire the first sales rep? Should you hire 2 at a time? What does one look for in their first sales hire? How does this change when selling to SMBs vs enterprise? * Bret was formerly the CTO at Facebook.

Scale 253

Scale Sales Hiring Sales Recruiting Sales 253

SaaStr

MAY 2, 2019

And then it was just a matter of, okay, make sure that it works, make sure that it scales, then very important not to forget, make sure that people buy it, that they know how to find you, you know. en you start saying, scaling and what does that even mean? They’re really giving them money to scale the business. Vlad : Ye ah.

Scale 208

Scale Business Sales Hiring CTO Hire 208

SaaStr

MARCH 30, 2025

Co-founders Dharmesh Shah (CTO) and Brian Halligan (Chairperson) shared at SaaStr Annual the unfiltered truth on building an SMB powerhouse, pivoting to product-led growth, and why the “M” segment is SaaS gold. At SaaStr, we’re obsessed with knowing how the best SaaS companies scale from zero to IPO and beyond.

Scale 201

Scale SMB Sales Hiring Scaling 201

Sales Hacker

DECEMBER 10, 2024

Currently, he’s the founder of MartinRoth.com, specializing in helping startups scale from $1M to $10M in ARR. Martin brings a wealth of experience in building and scaling sales teams, developing effective go-to-market strategies, and navigating the challenges of startup growth. I’m not a founder.

Scale 116

Scale Sales Hiring Scaling CTO Coach 116

SaaStr

JULY 19, 2019

Previously, Peter was also the CTO/CIO of CBS Interactive where he brought CBS into the cloud. At Sun, Peter was the CTO of the Liberty identity consortium that designed SAML 2. Why is it no longer to come into large enterprises with a small contract and expand? How has Peter found the transition from CTO to CEO this time?

VP of Engineering 160

VP of Engineering CTO Hire Technical Review Sales Hiring 160