SaaStr

FEBRUARY 25, 2025

Including: CEO Snowflake CEO HubSpot CEO DropBox CEO Descript CEO Clio CEO Flock Safety CEO Own CRO ServiceTitan CMO Databricks CMO Infinite Reality CTO Rubrik CCO Canva CCO Bill CCO GitHub VP AI Wiz CEO Calendly and 100s more!! Investor Connections and Funding Opportunities — And $5m AI VC Pitch Stage!!

Sales Recruiting 193

Sales Recruiting Scale CTO Hire Sales Hiring 193

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. Why is it so hard for SMBs to hire the best talent when competing with big companies?

SMB 107

SMB Sales Recruiting Branding Sales Hiring 107

SaaStr

JUNE 12, 2025

We’ve been saying for months that speed is the new moat in SaaS Sales with the advent of AI, and yeah, that’s still 100% true. AI hasn’t just changed how we prep for sales calls or conduct discovery. It’s fundamentally rewired how SaaS sales works, period. Product managers who understand legal.

Scale 217

Scale AI Sales Hiring CTO Hire 217

SaaStr

JANUARY 9, 2025

Every time I see a CTO that doesn't code themselves, they fail. — Jason SaaStr 2025 is May 13-15 Lemkin (@jasonlk) November 28, 2024 So we’ve talked a ton on SaaStr over the years on the risks and benefits of hiring your various VPs and C-level execs. This VP of Eng / CTO never knows the magic, the why, or the how.

Part-Time VPE 307

Part-Time VPE Sales Hiring CTO Hire Scale 307

Scytale

FEBRUARY 10, 2025

Accelerate sales Clients are increasingly concerned about the safety of their data and hesitant to trust just any organization. Proving due diligence regarding information security can drag out the sales process. This provides you with a significant competitive advantage over companies.

Systems Review 52

Systems Review Software Review CTO Hire compliance 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. Enterprise sales cycles were painfully long with limited data points. It took 12 years to fix these metrics.

Scale 193

Scale SMB Sales Hiring Scaling 193

Sales Hacker

FEBRUARY 18, 2025

Before that, he was the first non-founder seller at three startups, turning early traction into a repeatable sales motion. Discussed in this Episode: When to hire your first account executives Key traits to look for in early sales hires Structuring compensation for first sales reps Should you ‘hire the buyer’ to be your sales rep?

Sales Hiring 95

Sales Hiring CTO Hire Scale VP of Engineering 95

SaaStr

NOVEMBER 19, 2020

IME, rough order to make hires in: VPM: $0.2m He asked which to hire first. If you have a few nickels in the bank, and you somehow find a great VP a half stage or even full stage early, just hire her. Hiring is so hard as it is. Make the hire now. ARR VPS: $1-$1.5m More here: [link].

Part-Time VPE 364

Part-Time VPE Sales Hiring CTO Hire Sales Recruiting 364

SaaStr

SEPTEMBER 10, 2020

Perhaps the single most important thing you can ever do in SaaS, at least after $1m in ARR or so, is hire the best VPs you can. We’ve talked a lot over the years about how not to hire a wrong VP of Sales — 70%+ of the first VPs of Sales don’t make it even 10 months. You need to hire up-and-comers.

Part-Time VPE 352

Part-Time VPE Sales Hiring CTO Hire Sales Recruiting 352

SaaStr

AUGUST 31, 2023

Dear SaaStr: How does a First Time Founder Identify 10x Hires? How do you hire a great CTO, a great VP of Product, a great VP of Sales … if you’ve never worked with one? There’s a reason almost every founder you talk to had a mis-hire for their first head of sales. It’s hard.

Sales Hiring 287

Sales Hiring CTO Hire CTO Coach CTO 287

SaaStr

JANUARY 19, 2024

He made many great leadership points, but one in particular rattles around my head a lot and I think deserves its own post: You usually won’t know if you’ve made a 10x hire … when you make the hire. My co-founder and our CTO were both wicked smart. But I didn’t know they were truly 10x hires. They more often rise up.

Sales Hiring 295

Sales Hiring CTO Hire New CTO CTO 295

SaaStr

JUNE 19, 2022

Two SaaS Metrics That Actually Don’t Matter That Much in the Earliest Days: Absolute Churn and Sales Cycles. SaaStr 564: Top 10 Learnings Architecting a High Throughput Critical API with RevenueCat CTO Miguel Carranza. with Jenn Knight, Co-founder and CTO of AgentSync, and Daryna Kulya, Co-founder of OpenPhone.

CTO Hire 290

CTO Hire CTO Sales Hiring Innovation 290

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 290

CTO Hire CTO Sales Hiring Scale 290

SaaStr

OCTOBER 9, 2020

A VP of Sales and Success A VP of Sales and Marketing A VP of Sales and Anything Else. Is usually not really a VP of Sales. Sales managers back when I never managed sales. For signs the prospective hire just won’t work out, no matter how strong they might look on paper.

Sales Hiring 257

Sales Hiring Part-Time VPE CTO Hire Sales Recruiting 257

TechEmpower SaaS

DECEMBER 11, 2023

While the appearance matters, remember you are hiring the development firm primarily for its development skills, not its graphic design skills. Is there a project manager? An account manager? While beneficial, some project managers hinder effective communication. cto , product , saas

Software Development 443

Software Development Development Software Review Software 443

TechEmpower SaaS

MARCH 4, 2024

Focusing on generative AI applications in a select few corporate functions can contribute to a significant portion of the technology's overall impact. Key Functions with High Impact Generative AI is revolutionizing sales by enabling dynamic pricing and personalized customer interactions, boosting conversion rates and customer satisfaction.

Generative AI 443

Generative AI CTO Hire AI Sales Recruiting 443

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? In 2008, he founded Yammer, an enterprise software company that David grew to 500 employees and $60 million in sales. Head of Sales.

CTO Hire 284

CTO Hire Sales Hiring Sales Recruiting CTO 284

SaaStr

DECEMBER 10, 2020

I hear again and again from SaaS founders growing to $5m, $10m ARR or even more that they don’t need a certain VP — with the exception of a VP of Sales. Basically, in SaaS, everyone “gets” that they need a VP of Sales. Hire not just 1-2 reps, but 10. I Need a VP of Sales. Manage a trade show?

Sales Hiring 363

Sales Hiring CTO Hire Sales Recruiting Scale 363

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. Lead generation tools do change, but the basic motions of sales and marketing haven’t changed much.

Scale 284

Scale Sales Hiring Sales Recruiting AI 284

SaaStr

MARCH 7, 2021

Yes, you can manage the sales team yourself. Fixing it yourself becomes the biggest time sink and excuse for not hiring there is. You end up spending all your time backfilling roles you should have hired. And even worse, you often sort of give up trying to make the hire. These are all full-time jobs by $1m ARR.

Part-Time VPE 293

Part-Time VPE Sales Recruiting Sales Hiring Scale 293

SaaStr

JUNE 23, 2020

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. She can be your CTO forever. That’s a different, and critical, job than CTO. Marketing is also an art and science.

Part-Time VPE 309

Part-Time VPE CTO Hire Fractional VPE Sales Recruiting 309

SaaStr

APRIL 7, 2021

There are roughly 2 types of start-up management teams. The first type is the kind of management team hired by second+ time founders. Often folks they convince to once again be a VP of Eng or VP of Sales. And if you are, you are going to naturally start off hiring up-and-comers to your first leadership team.

Part-Time VPE 282

Part-Time VPE Sales Hiring Sales Recruiting CTO Hire 282

SaaStr

FEBRUARY 15, 2021

There’s a slide I see again and again from start-ups: 2 of the early sales reps are at 100% of quota, sometimes 150%-200%. So why so often, do only 2 of the first 8-10 sales reps perform? The first 2 scaled reps you hire that hit plan (some may churn before then) get special training. They get CTO training.

Scale 348

Scale CTO Hire Sales Hiring New CTO 348

SaaStr

MARCH 1, 2024

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 can hack managing and finding 1–3 reps yourself, but after that, you really need a VP of Sales. She can be your CTO forever.

Scale 274

Scale Part-Time VPE CTO Hire Fractional VPE 274

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. It’s happened to me, and I think for whatever my faults, I have a pretty high EQ and am a half-decent manager. In my first start-up, there was one engineer we had no choice about. Everyone hated him.

Part-Time VPE 284

Part-Time VPE Sales Hiring CTO Hire Scale 284

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 639: Scaling a SaaS Sales Team While Building Culture with Figma VP of Sales Scott Pugh   3. 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

JULY 3, 2022

The Ultimate Guide for Hiring a Great VP of Sales. Dear SaaStr: How Many Sales Reps Do I Need? Top Podcasts This Week: SaaStr 568: Mind the Gap: Balancing Growth and Efficiency in Tougher Times with Point Nine Managing Partner Christoph Janz. 10 Common Misconceptions About Getting Funded. Top Videos This Week: 1.

CTO Hire 258

CTO Hire Sales Hiring CTO Scale 258

SaaStr

JUNE 12, 2022

with Jenn Knight, Co-founder and CTO of AgentSync, and Daryna Kulya, Co-founder of OpenPhone. Attract, Hire & Build a Diverse Sales Team | Handshake VP, Employer Partnerships Jessica Peluso. Attract, Hire & Build a Diverse Sales Team | Handshake VP, Employer Partnerships Jessica Peluso.

Scale 237

Scale Sales Hiring CTO Hire CTO 237

SaaStr

FEBRUARY 15, 2023

Lightspeed Partner, Anoushka Vaswani, is joined by Raj Sarkar, CMO at 1Password, Kim Walsh, SVP, Sales, Partnerships and Customer Success at Apollo.io, and Chris De Vylder, CRO at Sentry, to pass along key lessons from their growth journey. Then build your segmentation and sales processes around that. 20 million?

Scale 244

Scale Sales Hiring CTO Hire Scaling 244

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. Q: Where Should SDRs Report — Marketing or Sales?

CTO Hire 242

CTO Hire Sales Recruiting Sales Hiring Scale 242

SaaStr

JULY 10, 2021

As a founder/CEO, building your first management team is something that you often lose sleep over. 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. And for good reason.

Sales Hiring 261

Sales Hiring Underperforming Technical Team Development Team Review CTO Hire 261

SaaStr

DECEMBER 20, 2023

So to serve both segments at the simultaneously, ZoomInfo has been rolling out a Product-led sales motion, that gives the ability for an SMB customer to sign up directly on their website for a free trial and grow into a paid customer, without ever having to talk to an sales rep or go through a demo process. So, what’s new at ZoomInfo?

New CTO 312

New CTO Scale Sales Hiring CTO Hire 312

Tom Tunguz

AUGUST 14, 2024

Kevin Scott, CTO of Microsoft, framed the opportunity in AI this way : work on problems that used to be impossible, but are now really hard. Nearly 10 years ago, I wrote a post about the minimum viable average contract value to justify a sales team. AI-based sales development changes the economics of this calculation.

CTO Hire 219

CTO Hire Sales Hiring Outsourced Development CTO 219

SaaStr

JANUARY 12, 2022

You have to be careful to pair that with someone strong to manage the relationship, that has more time and that also can be trusted. As a founder, you’ll just run out of time to properly manage key customers and partners yourself. Hire that person, and make sure they are someone the top customers can really trust and count on.

CTO Hire 325

CTO Hire Sales Hiring New CTO CTO 325

SaaStr

JULY 5, 2024

GTM Mistake #1: A VP of Sales That Can’t Sell or Demo the Product Mistake number one has always been an issue, and it’s the number one reason startups struggle in today’s world. They hire a VP of Sales who doesn’t want to sell or learn the product. You also don’t want to hire a VP of Sales who won’t carry a bag.

CTO Hire 209

CTO Hire Sales Hiring New CTO Venture Capital 209

SaaStr

MARCH 15, 2019

I remember my CTO once arguing with a Fortune 500 company on a “security” concern they had which really made no sense. More here: I Never Lost a Customer I Actually Visited | SaaStr Not hiring a full-time RFP person. They are too much work to just dump on a product person, success person, sales leader, etc. Didn’t matter.

Sales Hiring 174

Sales Hiring Enterprise CTO Hire CTO 174

Intercom, Inc.

FEBRUARY 28, 2018

A big part of why we are seeing this growth is that our customers have found that when they use Intercom to engage their website visitors, conversion rates and sales increase by more than 80%! That means we’ll be hiring 350 people over the next 18 months across our offices in San Francisco, Dublin, London, Chicago and Sydney.

Sales Hiring 195

Sales Hiring Scale CTO Engineering 195