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 141

Scale Sales Hiring Sales Recruiting Technical Advisors 141

Sales Hacker

JANUARY 21, 2020

SMB Sales & SDRs at (Smaller) Scale [18:20]. We were part of the office of the CTO. At that time, Marc Andreessen, the founder was the CTO of the company and there were only three of us in the group. It was pretty easy being an SDR for Marc Andreessen because he’d been on the cover of Time magazine.

Payment Methods 60

Payment Methods Scale CTO Coach SMB 60

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. We had to say: what does SMB want? So, we combined our 20 products into one and said here’s a package for SMB, here’s a package for mid-market, and here’s a package for enterprise.

CTO Coach 52

CTO Coach Customer Success VP of Engineering CTO Hire 52

Mucker Capital

APRIL 6, 2023

It's very hard for PLG to be the only or main motion with infrastructure products because it's not something one engineer will just test and buy. Obviously if you target enterprise customers, you usually have a very large ACV (Annual Contract Value) and the product usually is complex. That is a natural hurdle for PLG motion.

Startup 52

Startup Scale CTO Hire Outsourced Development 52

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. The SMB market offered a sweet spot between enterprise complexity and consumer scale.

Scale 177

Scale SMB Sales Hiring Scaling 177

SaaStr

MAY 27, 2024

Public valuations are still at a fraction of their 2021 peaks, but seed rounds are more expensive than ever. Investors should immediately engage with the CTO to assess their technical capabilities and potential, as great CTOs can demonstrate their exceptional skills quickly. Is it sustainable?

CTO Hire 277

CTO Hire Development Team Review Software Review Technical Review 277

SaaStr

AUGUST 15, 2020

Nick Mehta: I think it’s really well said and I think that what I’m seeing, actually, in some cases as chief customer officers getting value engineering, like you have in pre-sales, underneath them as well to tie that altogether. From contract signature to launch. We are still heavily oriented to SMB and to entrepreneurs.

Payment Methods 261

Payment Methods Merchant Services Scale Payments 261

SaaStr

MARCH 12, 2019

How can founders know when is the right time to make the move from SMB to enterprise? Because one message isn’t necessarily always transferable when considering kind of SMB to enterprise. ” How do you know when’s the right time to think about moving from an SMB and mid-market to enterprise?

Scale 206

Scale Enterprise Scaling Sales Hiring 206

SaaStr

DECEMBER 3, 2020

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? * We were hired into the same role, same start date, competed head to head. Bret was formerly the CTO at Facebook.

Scale 214

Scale Sales Hiring Sales Recruiting Sales 214

OnStartups

JULY 7, 2021

And I think part of it's because you've been in the game for a while and you're incredibly successful. Is your title CTO? Dharmesh: Yes, CTO. How do you have time to have your hands in all this different stuff? He was like, "You should probably hire someone outside of HubSpot for this role, for your growth.".

Payment Methods 140

Payment Methods Technical Review Software Review Payment Solutions 140

OnStartups

JULY 7, 2021

And I think part of it's because you've been in the game for a while and you're incredibly successful. Is your title CTO? Dharmesh: Yes, CTO. How do you have time to have your hands in all this different stuff? He was like, "You should probably hire someone outside of HubSpot for this role, for your growth.".

Payment Methods 40

Payment Methods Technical Review Software Review Payment Solutions 40

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 141

VP of Engineering CTO Hire Technical Review Sales Hiring 141