SaaStr

DECEMBER 1, 2020

We’ve talked a lot on SaaStr about the damage a bad VP of Sales can do. More on that, and the line between Great, Good and Bad here : But what if you are struggling to just find a Good VP of Sales … should you hire an Interim one? A good interim, seasoned, proven VP of Sales: Will help you focus.

Sales Hiring 321

Sales Hiring Sales Pricing SaaS 321

SaaStr

NOVEMBER 16, 2021

Q: Dear SaaStr: What Are The Top 3 Criteria for Hiring Your First Head of Sales? We’ve talked a lot on SaaStr about hiring that first VP of Sales. Do they have proven success selling at your price point? Training is a critical part of sales management. This is #1 by far. Can they train you ?

Sales Hiring 321

Sales Hiring Sales Pricing Management 321

SaaStr

MAY 10, 2024

At this week’s Workshop Wednesday, Lucas Price, former SVP of Sales at Zipwhip and founder and CEO at Yardstick, shares his insights on how to hire and build a high-performing sales team. During that time, he wasted a lot of money on failed sales hires and decided to learn everything about hiring sellers.

Sales Hiring 245

Sales Hiring Scale Sales Interviewing 245

SaaStr

APRIL 1, 2023

So everyone is now paying the price for lowering the bar in the Boom Times of mid ‘20 to early ‘22. On the hiring side, it often seemed like you just couldn’t hire anyone. Everyone was hiring everyone, anyone, back in mid-2021. We hired job hoppers that never stayed anywhere for more than 18 months for leadership roles.

Sales Hiring 316

Sales Hiring Investment Leadership Startup 316

SaaStr

JULY 12, 2021

Q: What are some common blind spots and mistakes startups make when hiring for and building out a sales team? Some of the top blind spots founders and even VPs of Sales make: #1. You hire a sales rep to sell before you can prove you can do it yourself. You don’t let reps go that fail in one sales cycle.

Sales Hiring 279

Sales Hiring Sales Recruiting Sales Branding 279

SaaStr

DECEMBER 11, 2021

We’ve talked about how all the Second Timers are hiring in customer success way early , ahead of sales, ahead of revenue. To hire in customer success. First, let’s make a rule, a compact, and a commitment: You Must Hire your First Customer Success Manager as a “Single Digit” Hire.

Sales Hiring 299

Sales Hiring Customer Success Headcount Churn 299

SaaStr

MAY 24, 2022

Many mediocre hires were made to fill slots, reference checks not made, etc. Yes, public stock prices are way down, which creates a lot of pressure in general and on venture fundraising in particular. And everyone got so tired with the accelerated hiring frameworks, that even more corners were cut than that. We All Need To).

Sales Hiring 323

Sales Hiring Sales Recruiting Interviewing Startup 323

SaaStr

FEBRUARY 7, 2025

His view is your sales team teaches your customers how to get value out of your product. Ron explains: “Wehire mostly technical backgrounds, but as our customers get larger and larger, you start to get global account managers, and they’re going to have much more business strategic account management experience.

Scale 182

Scale Sales Hiring Scaling Revenue 182

SaaStr

MARCH 12, 2021

We’ve talked a lot about hiring a great VP of Sales at SaaStr, and I’ve relinked to some of the most popular posts below. But after 5+ years of SaaStr.com, I think we can almost boil it all down to 2 things to look for when you make the hire — and 2 things not to look for as much. That takes years to learn.

Sales Hiring 279

Sales Hiring Sales Recruiting Scale Development Team Review 279

SaaStr

APRIL 2, 2025

Dear SaaStr: How Long Should You Give a New Sales Rep? sales cycles. Sales is tough. And while sales is pretty similar in SaaS at a given price point / ACV, different products are still different to sell.A sales cycles, it rarely works out. sales cycles, I’ve seen that work.

Sales Hiring 179

Sales Hiring Sales Onboarding Pricing 179

SaaStr

JULY 17, 2022

Q: Dear SaaStr: When Should a Startup Hire its First Sales Person, and What Should Their Profile Look Like? Try to close at least 10–20 customers yourself first, before you hire a sales rep. Then, hire a sales rep to help you. Then, hire a sales rep to help you. A bit more here. More here.

Sales Hiring 264

Sales Hiring Scale Startup Sales 264

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 299

Revenue Scale Sales Hiring Compensation 299

SaaStr

JANUARY 23, 2025

You need: Sales leaders who understand complex, multi-stakeholder deals Customer success teams ready for high-touch support Legal expertise for enterprise contract negotiation Product leaders who can balance current needs with future vision Pro tip: Hire enterprise reps in pairs. If both succeed, you’re ready to scale.

Enterprise 244

Enterprise Sales Hiring Scale Outsourced Development 244

SaaStr

MARCH 18, 2025

As Colin describes it, “I went to the CEO and asked to generate more revenue and hire more people, which is counter-intuitive to the standard approach where revenue leaders may sandbag to over deliver and crush numbers.”

Scale 191

Scale Sales Hiring Scaling Headcount 191

SaaStr

APRIL 13, 2025

Pricing advantages : Compound products can optimize pricing across their entire bundle, allowing them to “run circles around competitors” in specific product categories. This structure enables a seamless experience that starts when a company hires someone.

Startup 162

Startup Sales Hiring Underperforming Technical Team Cloud 162

SaaStr

NOVEMBER 10, 2022

And importantly, in the boom times of late 2020-early 2022 … in many cases, all hiring discipline was lost: Everyone lowered the hiring bar, which reduced efficiency. Sales teams hired way, way ahead to hit huge plans, and in many cases, ended up with a tough combo of lower quota attainment and higher comp structures.

Sales Hiring 325

Sales Hiring Pricing Cloud Startup 325

SaaStr

MAY 27, 2022

41% of you have sales do some customer onboarding, not just CS or other specialists. Should sales just disappear once the contract is signed? #5. On average, you got a 33%+ boost in revenue when you hired your first VP of Sales. Hire a great VP of Sales, and revenue goes up. So yes, it always works.

Sales Hiring 340

Sales Hiring Pricing Scale Interviewing 340

SaaStr

NOVEMBER 30, 2020

Now … On that deal … go quote twice your highest price ever. What it does force you to think about is providing a true solution to a big problem (more on that here: A Solution Sale Can Capture 3-20x the Revenues of A Tool Sale. That solves me having to hire an engineer, or 3, to do something. Almost always.

Pricing 321

Pricing Sales Hiring Engineering Enterprise 321

Tom Tunguz

JULY 10, 2024

Pricing an AI product will be a defining question in software for the next few years. We can observe the market trends today across some of the larger SaaS companies who offer AI pricing. Company Product Base Price AI Price Ratio Github Github Enterprise 21 10 0.67 AI products offer productivity gains.

AI 276

AI Pricing Sales Hiring Strategy 276

SaaStr

MARCH 18, 2024

Dear SaaStr: If you were hiring a head of sales for a high-priced, niche B2B SaaS product, would you focus on general B2B SaaS sales experience or on market/customer knowledge, assuming it will be very difficult to find a candidate with both? You’ll be very tempted to hire someone with a seemingly magical rolodex.

Sales Hiring 317

Sales Hiring Sales SaaS B2B 317

SaaStr

FEBRUARY 5, 2021

Would you still hire them if they hadn't last worked at [insert logo here]? You’ll be very tempted to hire someone with a seemingly magical rolodex. You’ll be very tempted to hire someone with a seemingly magical rolodex. But at $250k a year, those two ringer deals can more than justify the hire. See who does better.

Sales Hiring 334

Sales Hiring Sales Enterprise Pricing 334

SaaStr

JANUARY 8, 2022

We’ve talked a lot on SaaStr about how to hire a Great VP of Sales, and how you have to close the first 10 or so customers yourself, and how when you do go to hire your first sales rep — make sure you hire two. But how do you get those first few reps right, when you haven’t made the hire before?

Sales Recruiting 290

Sales Recruiting Sales Hiring Sales Pricing 290

SaaStr

JUNE 28, 2020

A debate so many start-ups go through is what to do about a Just OK VP of Sales they’ve hired. The VP of Sales turns out to be OK, but great. A Great VP of Sales has an immediate impact and closes much more than before she started. A Bad VP of Sales sees bookings decline. Like in one sales cycle.

Sales Hiring 324

Sales Hiring Scale Sales Scaling 324

SaaStr

FEBRUARY 7, 2021

When you go to hire a VP of Sales or even your first sales rep, one of the top qualifying questions I always recommend asking is if they have experience at your deal size, at your ACV (Annual Contact Value). And sales professionals certainly can learn skills and go up (and perhaps even down) a deal size in sales.

SMB 334

SMB Sales Hiring Scale Enterprise 334

SaaStr

DECEMBER 2, 2020

My 7 top tips to increase sales quickly. Hire a great VP of Sales. Hire a great VP of Sales, and even if nothing else changes … she’ll increase the revenue per lead by 20–100%+. In one sales cycle or less. More here: How My VP, Sales Doubled Our Sales in 90 Days. Raise prices 20%.

Scale 321

Scale Sales Hiring Sales B2C 321

SaaStr

JULY 2, 2021

I’ve written a lot about this, but for most start-ups, you can boil it down to two criteria any first VP of Sales just has to meet: Has she built at least a small team before? Have they hired at least 2–3 reps that have performed well? If you can hire 2–3 great ones, you can likely scale and hire 20–30. More here: [link].

Sales Recruiting 290

Sales Recruiting Sales Hiring Scale Development Team Review 290

SaaStr

DECEMBER 16, 2022

Sam Blond, Partner at Founders Fund, joined Matt Plank, VP of Sales at Rippling, to unlock the secrets to exponential revenue growth. Instead, they focused on how it’s the one that takes away busy work beyond payroll by helping with new hires’ IT requirements, saving founders significant time. Scaling your go-to-market efforts.

Outsourcing Services 287

Outsourcing Services Scale Sales Hiring Outsourced Development 287

SaaStr

JULY 9, 2021

Q: What are the common mistakes in the sales process that may lead to customer loss? In SaaS, the prospect is expecting the sales rep to be their guide, their expert on the product. The best sales reps listen and hear what the prospect’s problem is in the space — and use the product to design a solution. Being dishonest.

Sales Hiring 306

Sales Hiring Sales Pricing Onboarding 306

SaaStr

JUNE 29, 2020

We’ve talked a lot on SaaStr over the years about all different types of VPs of Sales. small, medium, and large) and through multiple processes (in-bound, out-bound, upsell, channel, partner) … you can’t expect your VP of Sales to be perfect at everything. And the endless hiring to keep up. And winning fast.

Sales Hiring 325

Sales Hiring Scale Sales Customer Success 325

Tom Tunguz

FEBRUARY 19, 2019

Others want to innovate in every dimension and re-invent every discipline from pricing to marketing to support to customer success. At the outset, Brad also sought to change the pricing model. So pricing’s a really difficult thing, right? We thought innovator pricing would be very important to us.

Pricing 277

Pricing Startup Sales Hiring Innovation 277

SaaStr

MAY 4, 2020

Q: How do you structure a sales team when you’ve got zero experience doing sales? Well, first go get some experience with sales ??. A few thoughts: First, make sure your sales reps can “eat”, that they can make enough money if they close deals. Second, only hire reps you’d buy from yourself. That helps a lot.

Sales Hiring 293

Sales Hiring Scale Sales Pricing 293

SaaStr

MARCH 25, 2021

The other day, a sales leader working asked me how I got to be “so good at sales.” In fact, that’s why I have so much respect for the art and process of sales. I saw you really could be 2-3x better than me in sales, and make it repeatable, and really scale that way. ” I’m not.

Scale 317

Scale Sales Hiring Sales Pricing 317

SaaStr

FEBRUARY 9, 2021

Few things will frustrate you more in the early days than long sales cycles on bigger deals. You’ll feel like you just don’t have the time for a 6, 9 or even 12 month sales cycle when you’re struggling just to put the first few points on the board. You cannot force 9 month sales cycles into 9 days.

Scale 345

Scale Sales Hiring Sales Pricing 345

SaaStr

MAY 28, 2024

If you’ve read SaaStr or have been around for the last decade, you might be familiar with some of the repeated GTM mistakes founders tend to make, but the world of hiring, people, scaling, and workplace expectations are significantly different today than they were before March 2020. Don’t make the hire. They weren’t getting any leads.

Sales Hiring 311

Sales Hiring Scale AI Search AI 311

SaaStr

MARCH 14, 2022

We’ve talked a ton about How to Hire a Great VP of Sales on SaaStr, but I wanted to highlight a few VP of Sales “personas” that I rarely, if ever, see work out. Because again and again, many of your will hire this VP of Sales. Here are the types of VP of Sales that just never work out.

Sales Recruiting 306

Sales Recruiting Sales Hiring Technical Review Scale 306

SaaStr

OCTOBER 3, 2024

And when we polled the 400+ CROs, CMOs and CCOs attending SaaStr Annual, almost 100% of them said they were hiring. To network, meet hundreds of great VPs of Sales, CROs, founders, and more. Literally, every single CRO at SaaStr Annual I talked to was hiring. These are sales execs after all! A gift, IMHO. 100% of them.

Sales Hiring 285

Sales Hiring Travel Sales SaaS 285

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.

AI 218

AI B2B ChatGPT Scale 218