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

DECEMBER 25, 2024

If you are sales-driven, youll usually stall out at $1.5m-$2m in ARR or so if you dont start growing the team to the next level, The First 50. Theres just physics here to get to $10m in ARR in a sales-led model, even a partially sales-led model: After $1.5m Youll need another sales rep at least per every $500k in new ARR.

Sales Hiring 264

Sales Hiring Scale SaaS AI 264

SaaStr

APRIL 12, 2021

The biggest mistake folks make when they go to hire a VP of Sales is hiring a top AE that's never really built a team. But it does not remotely prepare you to be a VP of Sales on its own. They are pretty good and each worth a read: If You are Going to Hire a Stretch VP — Do It Early.

Sales Hiring 340

Sales Hiring PayPal Growth Hacking Startup 340

SaaStr

DECEMBER 19, 2024

Go Hire That Missing VP! The best way to get out of a hole is to hire a great VP. A great VP of Sales. Well, stop saying you cant hire anyone. And just go finally hire her. Everyone lowered the hiring bar in the Boom. And perhaps most important, move on from mediocre customer success folks.

Sales Hiring 286

Sales Hiring SaaS Venture Capital Healthcare 286

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 263

Sales Hiring CTO Hire Scale Startup 263

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. Recently, I was talking to the CEO of a pretty successful SaaS company doing ~$3m in ARR, growing nicely, in a good space. You hire a Great VP of Marketing.

Sales Hiring 344

Sales Hiring Headcount Engineering Banking 344

SaaStr

SEPTEMBER 23, 2021

A "VP of Revenue" often knows nothing about inside sales or building a sales team. A "CRO" often doesn't want to do sales anymore. Ok this is a seemingly simple post but if you are hiring your first or second batch of VPs it will really, really save you some time. Marketing is adjacent to sales.

Sales Hiring 328

Sales Hiring Sales Recruiting Growth Hacking Product Marketing 328

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

DECEMBER 25, 2020

Or more simply, sometimes the bottom 10% of your customer base in terms of ACV just takes way too much time. The small guys suck up all your customer success and support resources, even though they make up only a small percent of your revenue. Instead, (z) hire them a psychiatrist. Hire Them a Psychiatrist Instead.

Sales Hiring 338

Sales Hiring Customer Success Customer Support Revenue 338

SaaStr

FEBRUARY 1, 2021

That you absolutely, positively, have to only hire “Rockstars” in your startups. If you don’t think you need a great VP of Sales, Product, Marketing, Customer Success, and Engineering — then all that all that means is you’ve never worked with a great one. The very best of the best.

Sales Hiring 290

Sales Hiring Part-Time VPE Scale Sales Recruiting 290

SaaStr

NOVEMBER 2, 2023

So we’ve spent a ton of time over the years on SaaS talking about hiring a great VP of Sales. Not only because it really matters, but because hiring the wrong VP of Sales can set you back a year — or longer. Don’t make this hire. 50% of what a VP of Sales really does is recruiting.

Sales Hiring 308

Sales Hiring Sales Recruiting Sales Interviewing 308

SaaStr

NOVEMBER 27, 2021

Is your CS team growing as fast as your sales team? If this is your first SaaS company, you may not have ever hired or built a Customer Success team. This one isn’t nearly as risky as a VP of Sales , or a VP of Marketing hire. You’ll make a good hire. reactive) help.

Sales Hiring 246

Sales Hiring Customer Success Scale Customer Lifetime Value 246

SaaStr

NOVEMBER 27, 2021

Is your CS team growing as fast as your sales team? If this is your first SaaS company, you may not have ever hired or built a Customer Success team. This one isn’t nearly as risky as a VP of Sales , or a VP of Marketing hire. You’ll make a good hire. reactive) help.

Sales Hiring 245

Sales Hiring Customer Success Scale Customer Lifetime Value 245

SaaStr

OCTOBER 7, 2020

As you scale up in SaaS, one thing I can almost guarantee is that you are going to hire some VPs who were either fired or quit their last role. So you’ll end up hiring VPs who went through a significant transition at their last gig, sometimes an involuntary one. You’re still going to hire VPs with some of these flags.

Sales Hiring 362

Sales Hiring Scale Interviewing Startup 362

SaaStr

MAY 27, 2021

For the past 10 years, I’ve been a sales advisor for the portfolio companies of early stage venture capital firm True Ventures. It’s fascinating work for a sales mind like mine that’s focused on helping brilliant people turn ideas into revenue-driving businesses. . In his piece, Jason recommends hiring VPs in a certain order.

Sales Hiring 252

Sales Hiring Scale Venture Capital Sales 252

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 299

Sales Hiring Management Leadership Engineering 299

SaaStr

SEPTEMBER 24, 2020

That when you make a mis-hire, you'll always look back and say you should have made a change 3-4 month earlier? When to hire them. Some classics here: How My VP, Sales Doubled Our Sales in 90 Days. If Your VP Sales Isn’t Going to Work Out — You’ll Know in 30 Days. Your VP of Sales Shouldn’t Be Perfect.

Sales Hiring 269

Sales Hiring Part-Time VPE Scale Underperforming Technical Team 269

SaaStr

SEPTEMBER 10, 2021

We’ve talked a ton on SaaStr about how to hire a great VP. We even have 3 great checklists to make sure you hire right: VP of Sales hiring checklist here. VP of Marketing hiring checklist here. VP of Customer Success hiring checklist here. Those can be amazing hires.

Sales Hiring 61

Sales Hiring Sales Recruiting Consulting Startup 61

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. Rookie error.

Sales Hiring 290

Sales Hiring Product Marketing Scale Marketing 290

SaaStr

MAY 6, 2021

A CRO owns and directs the strategy over a company’s revenue cycle, but there’s not a set standard for operational or management decisions: in addition to sales and sales development, they might be responsible for customer success, lead generation and pipelines, and even marketing and brand development.

Sales Hiring 305

Sales Hiring Sales Recruiting Interviewing Revenue 305

SaaStr

JULY 11, 2024

How Do You Sift Out the Bitter and Broken Individuals When Hiring? If it’s a role you’ve never hired, find someone great at it and have them do your final interview. For sales, product, or customer success, the best question you could ask is, “What would you do your first couple of weeks?” You interview 30 people.

Sales Hiring 291

Sales Hiring Scale Marketing Interviewing 291

SaaStr

SEPTEMBER 19, 2021

If you want to hit the plan for Q1'22, You need to be hiring all the sales reps you'll need then … Now. The biggest pro is it recurs With even 120% NRR, you basically double in 4+ years even with no new customers. To make the hires you need now, for next year. But you have to hire them NOW, not in January.

Sales Hiring 290

Sales Hiring Scale Headcount Acquisition 290

SaaStr

OCTOBER 22, 2020

Recently, a good friend of mine running a Hot SaaS Start-up asked me if he should hire a particular VP of Product candidate I knew well. The team he’d be managing was a big thumbs up on him. Just don’t hire her. And I’d say my success rate so far is about 19/20. And the CEO hired him. Let her go.

Sales Hiring 263

Sales Hiring Sales Recruiting SaaS Engineering 263

SaaStr

JUNE 14, 2020

To hire 3-4 folks to do what you used to do mostly yourself. To want a head of sales operations and a director of sales to help carry the load not later … but on Day 1. To not have to manage any customers yourself in customer success, and instead be a strategist. Do you have the budget?

Sales Hiring 304

Sales Hiring Scale Sales Recruiting SaaS 304

SaaStr

OCTOBER 10, 2022

A gap opens up when: – Sales abandons the customer the moment deal is closed – Support too reactive & slow to solve real issues – Deployment harder than should be. What I mean is, with most SaaS companies, there’s just a huge customer workflow break. So Customer Success becomes the default Gap Filler.

Customer Success 333

Customer Success Sales Hiring Scale Interviewing 333

SaaStr

AUGUST 7, 2024

Dear SaaStr: Our VC Is Encouraging Us to Hire Aggressively and Increase the Burn Rate. Most of the first-time founders I’ve invested in aren’t “spending enough” in that they are a bit too slow to make accretive hires. They don’t know at first, but they learn, as they cross 50, 100, 200 customers.

Sales Hiring 287

Sales Hiring Venture Capital Investment Customer Success 287

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 299

Sales Hiring Sales Recruiting Scale Scaling 299

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. The SMB sales team was incentivized purely on logo acquisition rather than revenue. With only 4% conversion by month two versus a 10% goal.

Revenue 299

Revenue Scale Sales Hiring Compensation 299

SaaStr

AUGUST 19, 2022

So we’ve talked a lot of the years on SaaStr on how to avoid a mis-hire for a key VP role: We’ve talked here about the 48 Types of VPs of Sales, and making sure you hire the right type. We’ve talked here about how to hire the right VP of Marketing, so you get leads and not just blue pens with your logo on them.

Sales Hiring 222

Sales Hiring Interviewing Customer Success Sales 222

SaaStr

JANUARY 12, 2024

Is it the end of an era for customer success in SaaS? We just wrote up how some of the biggest changes of SaaS are now coming, specifically in Customer Success and Sales. Customer Success Is Vulnerable to Cuts Jason shared that he didn’t realize how vulnerable customer success was to cuts until 2023.

Sales Hiring 323

Sales Hiring Customer Success Scale AI 323

SaaStr

SEPTEMBER 6, 2021

Q: Who Should Our First Head of Customer Success Report To? Ah, who should Customer Success report to. VP of Sales (once you have one). There are clear Pros and Cons to reporting to a VP of Sales. The Pros are: Usually, a VP of Sales is your best manager. It’s not super simple. image from here.

Customer Success 315

Customer Success Sales Hiring Finance Churn 315

SaaStr

JUNE 27, 2020

A little while back we put together some of the top sales & marketing mistakes SaaS companies and founders make, especially in the early days. Sales: Hiring any reps you wouldn’t buy from yourself. Later, once you have a strong VP of Sales, it’s fine though. Your sales reps need to eat. Hiring just 1 rep.

Sales Hiring 363

Sales Hiring Scale Startup Marketing 363

SaaStr

JANUARY 23, 2025

Build the Right Team for Enterprise Success Enterprise selling requires a fundamentally different skillset. Master the Multi-Stakeholder Sale Enterprise deals aren’t won in a single meeting. If both succeed, you’re ready to scale.

Enterprise 244

Enterprise Sales Hiring Scale Outsourced Development 244

SaaStr

AUGUST 17, 2024

Dear SaaStr: Does It Make Sense to Have Post-Sales Functions Report into Sales? In theory, why not let sales “keep” the customer longer? They already know the customer, after all. Even if having a CRO own post-sales and CS is becoming much more common these days. Because most great VPs of Sales are closers.

Sales Hiring 321

Sales Hiring Sales Customer Success Revenue 321

SaaStr

JULY 14, 2024

Hiring and Interviewing Tips: Jason emphasizes the importance of interviewing at least 30 candidates for a role and consulting with an expert in the field to interview the final candidate. Product-Led Growth (PLG) vs. Enterprise Sales: Jason discusses the evolution of PLG, noting that it’s essentially freemium with better analytics.

Sales Hiring 263

Sales Hiring Outsourcing Services Scale Interviewing 263

SaaStr

MARCH 1, 2020

The good news today, is there are tons of customer success veterans out there. Even just a few years ago, there weren’t enough folks when enough experience to be your first “head of customer success.” You’ll learn if they focus most on account growth vs. retention vs NPS growth, and in what order.

Customer Success 329

Customer Success Sales Hiring Leadership Interviewing 329

SaaStr

JUNE 10, 2021

We’re hiring for several roles for our tiny but might team at SaaStr, but our top priority is really professionalizing customer and account success by bringing on a great seasoned customer success leader. We’re looking for a self-starter that loves making customers happy.

Customer Success 279

Customer Success Sales Hiring Cloud Strategy 279