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

SaaStr

OCTOBER 29, 2021

This is the sort of organic upmarket path you see with a lot of leaders who don’t go 100% “all in” on enterprise but aggressively support it: #2. Use overages to renegotiate contracts, not charge per event. They’re growing even faster at scale. CEO Spencer Skates owns 8.5%, CTO Curtis Liu 8.0%.

Scale 300

Scale CTO Hire New CTO CTO 300

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. CTO (40 Employees).

CTO Hire 278

CTO Hire Sales Hiring Sales Recruiting CTO 278

SaaStr

MARCH 7, 2021

These are all full-time jobs by $1m ARR. 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. Hard go truly enterprise without it.

Part-Time VPE 286

Part-Time VPE Sales Recruiting Sales Hiring Scale 286

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. SaaStr 569: Classic Episode: Succeeding As a Young Enterprise Founder with Front Co-Founder and CEO Mathilde Collin.

CTO Hire 255

CTO Hire Sales Hiring CTO Scale 255

SaaStr

JUNE 12, 2022

SaaStr 560: Enterprise Communities: The What, Who, Why, When & How with Venafi Head of Community, Holly Firestone. SaaStr 559: Secrets to Building Your Marketing Engine To Drive Scale with Airtable CMO Archana Agrawal. Top 5 Mistakes Building & Scaling Global Product Teams | HubSpot GM & VP, Products Poorvi Shrivastav.

Scale 235

Scale Sales Hiring CTO Hire CTO 235

SaaStr

DECEMBER 20, 2023

So in Enterprise, they have around 2,000 companies spending $100k or more per year and dozens of companies spending over a million per year. So in Enterprise, they have around 2,000 companies spending $100k or more per year and dozens of companies spending over a million per year. Is it Cheaper or Better to go PLG?

New CTO 305

New CTO Scale Sales Hiring CTO Hire 305

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. His answers didn’t disappoint.

CTO Hire 241

CTO Hire Sales Recruiting Sales Hiring Scale 241

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 258

Sales Hiring Underperforming Technical Team Development Team Review CTO Hire 258

SaaStr

JANUARY 4, 2024

Jason Warner , who was CTO of GitHub before and during my time as COO there (and a former partner at Redpoint!) All of our Managing Directors on the early team have both founded companies and operate at scale. She invests primarily in enterprise software with a focus on DevTools, Infrastructure, AI, Security and open source.

Management 268

Management CTO Hire New CTO CTO 268

SaaStr

JULY 14, 2022

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. 2017 The Third SaaStr Annual: Scale Together. 2017 The Third SaaStr Annual: Scale Together.

Scale 300

Scale Sales Recruiting CTO Hire New CTO 300

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. Find and hire two other similar reps.

Scale 278

Scale Sales Hiring Sales Recruiting AI 278

SaaStr

AUGUST 25, 2023

On top of that, founders are full of excuses preventing them from scaling. You have to see: A couple of good hires brought in Improvement on some metrics A big deal or two hanging out there, brought in and closed Things taken off your plate. But after a couple million in ARR, you can afford any hire if they’re accretive.

Part-Time VPE 241

Part-Time VPE Sales Hiring Scale CTO Hire 241

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. There are rules in starting an enterprise software company. They’re going to figure out that enterprise is the actual way to go, and it’ll be OK.” It got better.

Part-Time VPE 283

Part-Time VPE Technical Cofounder CTO Hire New CTO 283

Sales Hacker

SEPTEMBER 29, 2020

Today on the show, we’ve got Vishal Sunak, CEO and co-founder of LinkSquares, a company that applies AI to your contract. Keys to success when scaling a company [10:56]. Sam Jacobs: Today on the show, we’ve got Vishal Sunak, CEO and co-founder of LinkSquares, a company that applies AI to your contract.

Scale 117

Scale CTO Hire CTO Coach Scaling 117

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

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. The contract size grows. Doing Business with Developers.

Outsourced Development 207

Outsourced Development Underperforming Technical Team Development Part-Time VPE 207

SaaStr

JANUARY 14, 2020

In this presentation, Pluralsight co-founder and CEO Aaron Skonnard will discuss how Pluralsight successfully transformed its business to serve both individual and enterprise customers independently and will share his lessons for SaaS companies looking to tap into individual customers to sell into enterprises and vice versa.

B2B 154

B2B B2C Scale New CTO 154

SaaStr

SEPTEMBER 26, 2019

So mid-market, we’re about 40 to 50K ACV enterprise. 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. We’re low six figures.

Scale 141

Scale Sales Hiring Sales Recruiting Technical Advisors 141

Sales Hacker

FEBRUARY 18, 2025

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? 31:55 Hiring for grit, curiosity & determination. What does Joe look like at that time?

Sales Hiring 89

Sales Hiring CTO Hire Scale VP of Engineering 89

OpenView Labs

JULY 2, 2020

Tips on Enterprise Pricing. Time and time again SaaS companies are promising customers that they will save hundreds of thousands of dollars, but their pricing strategies are only capturing a tiny fraction of that savings. Product Strategy for Scale: Pricing. Tips on Enterprise Pricing.

Pricing 138

Pricing SaaS Payments Payments SaaS 138

Intercom, Inc.

OCTOBER 31, 2019

When a company is moving from the startup to the scale-up phase, there is the potential for productivity practices to be lost along the wayside. Dee: And you’ve worked in the industry for more than 22 years, so you have an incredible insight into the expansion of cloud networks, enterprise and data center technologies.

Artificial Intelligence 169

Artificial Intelligence Scale CTO Hire Technology 169

Scytale

OCTOBER 21, 2024

Streamlining the Sales Process: Ever been knee-deep in contract negotiations when the client suddenly asks, “Are you SOC 2 certified?” Yaron Lavi CTO at Deel Book a Demo Unlocking Business Opportunities with SOC 2 Certification Now that you’ve put in the hard work to become SOC 2 certified, it’s time to reap the rewards.

Technical Review 52

Technical Review Scale compliance CTO Hire 52

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. And so we hired somebody who had a lot of experience and could recommend ways to build the team.

Outsourcing Services 216

Outsourcing Services Sales Hiring CTO Hire Acquisition 216

SaaStr

APRIL 4, 2019

You’ll also learn how leading SaaS companies are able to scale and thrive in this complex, dynamic environment. It’s changing the landscape for large enterprise that you are very familiar with. And the same customer challenges that we were being presented, which was: How do you scale? Join us for SaaStr Annual 2020.

Cloud 171

Cloud Scale Trends Machine Learning 171

Intercom, Inc.

JANUARY 5, 2022

And as nice as verbal assurances and a handshake are, as you grow and try to sign with more established, enterprise-level companies, you’ll find yourself more and more having to provide proofs of compliance before closing the deal: The shift to the cloud, more and more data breaches – it really put a magnifying glass on third-party risk.

Scale 212

Scale Software Review compliance Technical Review 212

SaaStr

APRIL 9, 2019

Mallun Yen : So, you were an engineer by training and then you became an engineering leader, as the CTO of Webex, and then you became a CEO. You’ve got to learn about sales, about marketing and, otherwise, you need to hire a lot of other people around you to help. Eric Yuan: Because, at that time, we really needed a product.

Sales Hiring 136

Sales Hiring Scale CTO Hire Marketing 136

Intercom, Inc.

FEBRUARY 22, 2022

As we scale, we’re working with larger mid-market and enterprise customers with more complex needs and specifications. Hiring and cultivating incredible talent on our Information Security team. The overlap and synergies between these teams means we can use automation to efficiently solve problems at scale while remaining lean.

Data 118

Data CTO Hire Technical Review Scale 118

Sales Hacker

OCTOBER 13, 2020

Instead, there’s one continuous streamlined customer-centric journey, leveraging the next generation of artificial intelligence, Outreach allows sales reps to deliver consistent, relevant, and responsible communication for each prospect every time enabling personalization at scale previously unthinkable. Are they hiring?

Marketplace as a Service 110

Marketplace as a Service CTO Hire Sales Recruiting Scale 110

Neil Patel

JULY 7, 2021

Do we have the technical support, in-house or contracted, to take on the learning curve of an emerging platform? As you scale, ensuring a great customer experience can become harder and harder, but building a solid e-commerce website can help. Do I need a platform to do all these things simultaneously and from one location?

AI Search 126

AI Search CTO Hire Scale Artificial Intelligence 126

Sales Hacker

OCTOBER 8, 2018

Chris is a 20 year Silicon Valley veteran having launched the first part of his career at EMC before finding his way to Snowflake in 2013. At Snowflake, he was the first rep and single-handedly built the outbound-engine on the way to scaling the business from pre-revenue all the way past $150M+ in ARR. Show Agenda and Timestamps.

Scale 77

Scale Sales Hiring Sales Recruiting CTO Hire 77

Sales Hacker

MARCH 25, 2019

Simmone talks about her experience building Gilt City and Kidpass as a woman of color and how she advises companies to build diversity and inclusion into their hiring practices and sales teams. How to build diversity into your hiring practices. It really starts in how you’re hiring. Unconscious bias is a part of all of us.

Sales Hiring 87

Sales Hiring Revenue CTO Coach CTO Hire 87

Mucker Capital

APRIL 6, 2023

If you're primarily targeting very large enterprise companies, it's very hard usually to use PLG as the only way to sell to those companies. Obviously if you target enterprise customers, you usually have a very large ACV (Annual Contract Value) and the product usually is complex. Are POCs part of the PLG play?

Startup 52

Startup Scale CTO Hire Outsourced Development 52

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 60

Payment Methods Scale CTO Coach SMB 60

SaaStr

JUNE 1, 2025

The latest one is all AI with a big enterprise / B2B slant and is very good but dense. China Is Playing a Different Game Entirely The Models Youve Barely Heard Of: DeepSeek R1: 93% performance of OpenAI’s o3-mini at fraction of training cost Alibaba Qwen 2.5-Max: 300+ pages. So weve summarized it for B2B founders below!

AI Search 238

AI Search AI CTO Hire ChatGPT 238

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. They’ve got a proven concept they need to scale. You run the gamut.

CTO Coach 52

CTO Coach Customer Success VP of Engineering CTO Hire 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. At SaaStr, we’re obsessed with knowing how the best SaaS companies scale from zero to IPO and beyond.

Scale 178

Scale SMB Sales Hiring Scaling 178