SaaStr

JANUARY 29, 2021

There’s an exercise I’ve been through with many founders that are just getting to Initial Traction, say $1m-$2m in ARR or so, sometimes less, where I map out their future hiring. They are often a bit shocked at how many people they are going to need to hire as they cross $10m ARR. Talkdesk inside sales team at $10m ARR.

Sales Hiring 350

Sales Hiring Headcount Scale Engineering 350

SaaStr

OCTOBER 13, 2024

I felt part of your core job as CEO was to assemble a management team, not complain about how you couldn’t get it all done. Or didn’t want to do sales. I still believe a CEO should “do it all” in terms of building a decent management team first before hiring a COO. Hiring a strong COO between Management Team 1.0

Sales Hiring 264

Sales Hiring CTO Hire Scale Startup 264

SaaStr

OCTOBER 20, 2020

Who should you hire, with limited budget? A VP of Sales? A truly great hire is >always< accretive. Hire anyone truly great you can find. And he was proud he’d just hired a VP of Sales at a below-market rate. You don’t want to save money on a great hire. In Just 2 Sales Cycles.

Sales Hiring 344

Sales Hiring Headcount Engineering Banking 344

SaaStr

NOVEMBER 24, 2020

Then, once you know how to do it yourself, you hire 2 sales reps. More on that here: When You Hire Your First Sales Rep — Just Make Sure You Hire Two | SaaStr. After you have 2 reps hitting quota, you hire a head of sales. A related post here: Should Your VP Sales Start Off as a Player-Coach?

Sales Hiring 300

Sales Hiring Scale Sales Management 300

SaaStr

DECEMBER 29, 2024

Top Posts of the Week: #1: Salesforce: Actually Were Going to Hire 2,000 Sales Execs Now To Sell AI #2: Gong: $100k Deals Take About 70 Days to Close #3: Why The Greatest Sales Teams Just Kill It On Dec 31. When Everyone Else Has Gone Home. #4:

AI 291

AI Sales Hiring Pricing Development 291

SaaStr

FEBRUARY 1, 2021

That you absolutely, positively, have to only hire “Rockstars” in your startups. A Rockstar engineer really is 10x better than the next tier. And yet … is it worth waiting 6-9 months to hire a VP that’s a true Rockstar, if you’ve struggled to make the hire? The very best of the best.

Sales Hiring 291

Sales Hiring Part-Time VPE Scale Sales Recruiting 291

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

APRIL 8, 2025

And thus — hiring more. They they are doubling down and hiring even more to keep these gains going. Net net, if the average RevenueCat engineer is twice as efficient as before AI dev tools (and it’s not that simple. but close enough) AND they then double their hiring … now they are moving 4x as quickly.

AI 289

AI Sales Hiring Scale B2B 289

SaaStr

MAY 12, 2022

The biggest mistake you can make as a founder when you hire your first VP of Sales is stepping out of sales. It only works with the very best VPs of Sales. Every other first VP of Sales needs you doing at least half of what you were doing before. A founder hires a Pretty Good First VP of Sales.

Sales Hiring 310

Sales Hiring Sales Investment Engineering 310

SaaStr

OCTOBER 2, 2024

Dear SaaStr: Why Do Founders Hire So Many Terrible VPs that Mislead Them? And Hiring folks to do something you don’t know yourself and/or haven’t done yourself. If you hire a VP of Sales and have never done sales yourself, you won’t really know. Same with marketing, engineering, everything. Needing a team.

Sales Hiring 291

Sales Hiring Scale Interviewing Engineering 291

SaaStr

DECEMBER 19, 2023

Dear SaaStr: What are the signs that an enterprise SaaS startup is ready to scale by hiring more sales people? For a higher-velocity, in-bound driven SaaS product, most sales reps will have trouble processing more than 50 or so truly qualified leads a month. Before $10m ARR or so, more qualified leads = more sales.

Sales Hiring 307

Sales Hiring Scale Scaling Sales 307

SaaStr

DECEMBER 25, 2020

The team, especially your engineering team and sales teams, may just not want to deal with the drama of a complaining segment. Instead, (z) hire them a psychiatrist. You don’t have to give them any more story points, or sales attention. Just the attention of this one brand new hire. But she can listen.

Sales Hiring 339

Sales Hiring Customer Success Customer Support Revenue 339

SaaStr

OCTOBER 27, 2020

Hiring too junior a resource to own product is almost always a huge mistake — 9 times out of 10. You can take a lot of “stretch” risk in sales. Sales breeds leadership. But what I’ve seen time and time again is “product managers” who haven’t actually owned anything. A VP of Product should be a transformational hire.

Sales Hiring 300

Sales Hiring Management Leadership Engineering 300

SaaStr

JULY 31, 2021

The time comes for every growing SaaS company when you need to hire your first managers. Not VPs, but Directors and managers under them. Some rough rules: You need one Sales Director for each 8 sales reps. Your VP can’t directly manage more than 8. Each 10 SDRs, even 8 ideally, need a manager.

Sales Hiring 325

Sales Hiring Scale Management Engineering 325

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 293

Sales Hiring CTO Hire CTO Coach CTO 293

SaaStr

MARCH 17, 2025

Hire an Ex Post-Facto Co-Founder: This is someone who isnt technically a co-founder but acts like one. It could be a VP of Product, Sales, or Engineeringsomeone who takes ownership of a big chunk of the business and cares almost as much as you do. Prioritize Great Early Hires. If youre technical, hire someone who can sell.

Sales Hiring 251

Sales Hiring Scale Scaling Engineering 251

SaaStr

JANUARY 26, 2021

There’s nothing wrong with hiring folks from the competition. Only hire them if you still would if they worked somewhere else. The time will come when you are first tempted to hire someone from your competitor. Hiring from your Competitor. Then, sure, hire all the great ones there. It may sound great.

Sales Hiring 294

Sales Hiring Interviewing Engineering SaaS 294

SaaStr

JANUARY 8, 2025

When Lindsey joined, she inherited an already built-out self-serve/PLG model for small businesses and a mid-market and enterprise sales, customer success, and post-sales team. But at the start of its expansion play, Checkr’s enterprise motion failed, and sales cycles were slow, taking up to a year for $100k & up deals.

Revenue 300

Revenue Scale Sales Hiring Compensation 300

SaaStr

FEBRUARY 7, 2025

For context,Ron has an MBA and a master’s in engineering from Stanford. His view is your sales team teaches your customers how to get value out of your product. Similar to most structures of a technical sales team. From the early days, we had a more technical sales team.” You gotta know the product cold.)

Scale 183

Scale Sales Hiring Scaling Revenue 183

SaaStr

JULY 13, 2022

Q: Dear SaaStr: What Were The First Five Hires You Made After Product-Market Fit? My first 5 hires at Adobe Sign / EchoSign, beyond the core founding+ team, once we had paying customers and first, if early, product-marketing fit: #1: Full-time sales rep at $8k-ish MRR. I Should have hired two. I hired at $20k MRR.

Sales Hiring 291

Sales Hiring Product Marketing Scale Marketing 291

SaaStr

SEPTEMBER 26, 2022

Dear SaaStr: When should a bootstrapped startup hire a (CFO, COO, CMO)? How can a CEO hire those C-level positions for the first time as a CEO and entrepreneur? Here are some rough rules: You want a VP of Everything (Sales, Marketing, Product, Eng) by about $5m ARR, and ideally, Sales and Marketing well before that.

Sales Hiring 291

Sales Hiring Part-Time VPE VPCs (Virtual Private Cloud) Startup 291

SaaStr

APRIL 28, 2025

The Journey: From WiFi to IoT Fleet Management Sekar’s journey began unexpectedly when he joined Meraki (founded by MIT researchers Sanjit Biswas and John Bicket) to help them figure out marketing and sales “from first principles.” This cross-pollination effect accelerated product development in unexpected ways.

Scale 245

Scale Transportation Scaling SMB 245

SaaStr

JANUARY 23, 2021

And I gave him an insanely great VP of Sales candidate. But like any candidate, this VP of Sales wasn’t perfect. He said he’d hire him … with a great package … but only as “Head of Sales” Not VP. And this VP Sales candidate met with another CEO I know well. A real gift.

VP of Engineering 348

VP of Engineering Sales Hiring Scale Engineering 348

SaaStr

MAY 30, 2023

Hiring has way slowed down, but many folks are still hiring, albeit at a reduced rate. 56% of you aren’t hiring, or barely hiring. But a good chunk of you are still hiring, albeit in moderation. Many did layoffs and capped hiring to get radically more efficient — and it worked.

Sales Hiring 279

Sales Hiring Headcount Engineering Revenue 279

SaaStr

APRIL 5, 2025

Here are the five channels that worked for Rupa: Search Engine Optimization (SEO) Social Proof and Trust Building Educational Partnerships and Rupa University Conferences and Event Sponsorships Outbound Sales and Data Quality Lets dive into each. Find trending topics, hire experts, and create the best content available for that topic.

Scale 233

Scale AI Search Sales Hiring Acquisition 233

SaaStr

JULY 3, 2023

Dear SaaStr: When Should You Hire Your First Demand Generation Marketer in SaaS? A deep dive on that and why here: I Hired My VP of Marketing at $20k MRR. In a recurring revenue model, you want to make every accretive hire you can. Or just hiring a junior marketer to start to save a few dollars. Even when you hire a VP.

Sales Hiring 279

Sales Hiring Marketing SaaS Engineering 279

SaaStr

MARCH 12, 2025

The 4 Things Most Founders Get Wrong About Marketing: “We’re a product company, not a marketing company” – The hard truth is that 9 out of 10 B2B companies spend more on sales and marketing than R&D. Better to hire for your specific needs and stage. These “five-five” CMOs barely exist.

Sales Hiring 208

Sales Hiring Marketing Technical Review Underperforming Technical Team 208

SaaStr

OCTOBER 27, 2022

You need engineering, product in all start-ups — but in SaaS, even in the very early days, you also need sales, client success, true support, demand gen marketing, etc. Why didn’t we just hire another 3 guys in TechOps much, much. I was lucky to have a great hire who handled our first few large customers.

Sales Hiring 300

Sales Hiring Sales Recruiting Scale Scaling 300

SaaStr

MARCH 22, 2022

This requires effort from your entire organization, and Handshake VP, Employer Partnerships Jessica Peluso outlines some changes that you can make to your brand, and your application, interview, and offer process that will help find the talent you are trying to attract and hire. Below is the transcript of Jessica’s session. Hi everyone.

Sales Hiring 265

Sales Hiring Sales Recruiting Scale Sales 265

SaaStr

JUNE 5, 2022

Most of you are hiring twice as many sales reps as last year. This isn’t an epic insight, but I did the poll because I find so many SaaS founders underestimate how many reps you have to hire. If you want to double, you have to at least double your sales team. At least. #23. Of course not. #24. Another Sigh.

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Sales Hiring Interviewing Revenue Sales 288

SaaStr

DECEMBER 16, 2020

We’ve talked a lot on SaaStr about how to make that critical hire: the VP Sales. But when you make a mis-hire, it’s about the worst mis-hire you can make. You’ll end up with a crummy sales team under a mis-hire. We’ve posted a script to use when interviewing a VP Sales.

Sales Recruiting 360

Sales Recruiting Sales Hiring Sales Engineering 360

SaaStr

JUNE 25, 2020

One of the classic original SaaStr posts was on the Top 10 Questions to Ask a VP of Sales Candidate. We did an update of that classic post below together with this brand new video on the topic: Use this script for hiring that first VP of Sales. Ready to hire your first VP Sales? And When to Hire One.

Sales Hiring 353

Sales Hiring Scale Interviewing Sales 353

SaaStr

NOVEMBER 20, 2024

Historically, the burden of customer feedback fell on the solutions engineers and CS architects. Other Learnings in the GTM Journey GitHub has had to adjust to new sales stages and new buyer personas. Sometimes, you have to say no or push them into a specific package, which is true post-sale for adoption.

Scale 265

Scale AI Scaling Marketing 265

SaaStr

APRIL 7, 2025

I’m shocked we don’t already have this for sales calls. By the end of the year, every single sales call should have a digital representative that can fill in when the human doesn’t know an answer. This will utterly change how we do sales. Don’t wait to launch your AI for a year.

AI 219

AI B2B ChatGPT Scale 219

SaaStr

MAY 12, 2023

Next up is Jason Cohen, founder of $100m+ WP Engine. Believing I had to do a job before I could hire someone to do that job It makes sense: How can you hire someone, and hold them accountable, if you don’t know anything about the domain? Then I tried hiring SEO experts. Here are my top ten mistakes.

Engineering 298

Engineering Sales Hiring Interviewing Scale 298

SaaStr

MAY 7, 2024

At SaaStr AI Day, Siqi Chen, founder, and CEO of Runway , discussed his belief of why every role will become a prompt engineering role, along with some no-code AI tips showing how to build products without knowing how to code. Why Is Every Role a Prompt Engineering Role Runway is a next-generation finance platform. How does that work?

AI 282

AI Engineering Sales Hiring ChatGPT 282

SaaStr

APRIL 13, 2025

This structure enables a seamless experience that starts when a company hires someone. One button click in Rippling sets up the new hire across HR, payroll, all relevant apps (Slack, Dropbox, GitHub, email, Salesforce), provisions their computer, and establishes them within the company’s financial systems.

Startup 163

Startup Sales Hiring Underperforming Technical Team Cloud 163