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

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. That’s usually enough in my book. That can be great.

Sales Hiring 362

Sales Hiring Scale Interviewing Startup 362

SaaStr

JANUARY 27, 2022

Q1 is really your last chance to get the hires done you really need for 2022. This is a pretty basic post, but one so many busy CEOs and founders just miss: It’s already almost too late to make the hires you need for 2022! And in sales it’s even worse. It takes 90 days to find a great hire. How can this be?

Sales Hiring 317

Sales Hiring Scale Scaling Onboarding 317

Tom Tunguz

APRIL 14, 2020

Sam Jacobs created the Revenue Collective , a group of more than 1700 sales professionals at some of the fastest-growing companies. With chapters across the US, Revenue Collective has broad reach within the sales community. 61% will see a decline in Q2 bookings relative to Q1. You can download the survey here.

Sales Hiring 334

Sales Hiring Sales Forecasting Travel 334

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

Tom Tunguz

FEBRUARY 7, 2019

As you build out your startup’s financial model for 2019, a key component will be the hiring plan. You’ll need to calculate the number of managers and individual contributors to achieve your goals. You will make mistakes hiring people. In the hiring plan, you should anticipate this. But don’t forget to plan for mishires.

Sales Hiring 244

Sales Hiring Engineering Customer Support Startup 244

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. You can try and hide this “issue” by talking about bookings instead of ARR. To make the hires you need now, for next year. But you have to hire them NOW, not in January. This is key.

Sales Hiring 290

Sales Hiring Scale Headcount Acquisition 290

SaaStr

JUNE 14, 2020

Each quarter, the bookings plan starts at $0 again. To hire 3-4 folks to do what you used to do mostly yourself. 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. Because SaaS is hard.

Sales Hiring 304

Sales Hiring Scale Sales Recruiting SaaS 304

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

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. If not on a month-over-month basis, then at least on a bookings basis.

Sales Hiring 324

Sales Hiring Scale Sales Scaling 324

SaaStr

AUGUST 26, 2020

Founder-led sales generally stops scaling around $1m-$2m ARR. But you see growth start to decline in new bookings, that's a sign. A sign to hire a real sales leader. Over the years at SaaStr we’ve talked a lot about hiring a great VP of Sales, when it works, when it does, and how it moves the needle.

Sales Hiring 328

Sales Hiring Sales Recruiting Scale Sales 328

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? Even if having a CRO own post-sales and CS is becoming much more common these days. A “true” VP of Sales often wants nothing more to do with a customer after a deal closes.

Sales Hiring 321

Sales Hiring Sales Customer Success Revenue 321

SaaStr

OCTOBER 18, 2019

I still see most startups way behind on their 2020 planning, and most importantly, hiring, at this point in the year. You can try and hide this “issue” by talking about bookings instead of ARR. Second, you have to try to hire as many of the sales reps you’ll need for the end of Q1 … by mid-Q4. You just can’t make it up.

Sales Hiring 242

Sales Hiring Scale Headcount Revenue 242

SaaStr

APRIL 7, 2020

In the early days of SaaStr, we wrote a bunch of posts that were controversial at the time, but later, most sales leaders eventually agreed with. That you know even in 1 sales cycle if a VP of Sales is going to work out. As soon as you hear a VP of Sales start to blame her/his own reports for missing a number, it’s over.

Sales Hiring 342

Sales Hiring Sales Retention Churn 342

SaaStr

JUNE 10, 2024

So in the earlier days especially, you’ll be tempted to lean on the sales team to do more than just … sell. Especially because the first 1-2 successful reps you hire will often be a bit of a product expert, and be great at really understanding customer problems. It has some positives, the more you ask sales to do.

Sales Hiring 325

Sales Hiring Scale Sales Customer Success 325

SaaStr

FEBRUARY 26, 2025

Only 21% of Salesforce’s Revenue is from … Sales This has been true for many years, but it often comes as a surprise to those that don’t know the company as well as they know its CRM. #2. It’s still adding almost $4B in net new bookings. Salesforce Growth: FY26 $40.9B (guidance) FY25 $37.9B 40 Billion ARR.

Scale 207

Scale Sales Hiring Azure Cloud 207

SaaStr

JANUARY 11, 2021

The moment comes when it’s time to hire your first VP Sales. We’ve talked in the past about the 48 Different Types of VP Sales , What a VP Sales Really Does , and even given you a Script to Use When Interviewing a VP Sales. So at this stage, the VP Sales, while necessary, sure looks expensive.

Sales Hiring 294

Sales Hiring Scale Sales Interviewing 294

SaaStr

JULY 8, 2024

How much more could you accomplish with your sales organization? Justworks CRO, Robert Lopez, and Director of Sales, Valeria Avila, show you how to create longevity in your sales organization and why it matters. One of the more controversial things Justworks does is pay AEs on their net book of business. They’ll step up.

Sales Hiring 293

Sales Hiring Scale Sales Education 293

SaaStr

DECEMBER 16, 2020

Q: What makes a great sales leader? The best sales managers / directors / VPs: Recruit great team members. Sales requires a linear number of hires to grow bookings. In fact, the best sales leaders always upgrade the team within 60 days of taking a new role. Retain the top hires.

Sales Recruiting 299

Sales Recruiting Sales Hiring Scale Sales 299

SaaStr

MARCH 3, 2023

At SaaStr APAC 2023, Scott Pugh, VP of Sales at Figma, shared how to scale these two sales teams while building culture. Pugh’s strategy is simple, albeit not always easy: Recruitment — how to hire the best talent to scale your sales organization. Define your hiring profile. Focus on the hiring profile.

Scale 278

Scale Sales Recruiting Sales Hiring Scaling 278

SaaStr

FEBRUARY 15, 2020

We put together a basic 50/50/25 VP of Sales comp plan early on at SaaStr, and it seemed time for an update. Incentives are critical, and the VP Sales will likely be the Seemingly Most Expensive hire you ever make. Even if you hire a VP Sales very early, there has to be a clear quota and plan for him or her to hit.

Sales Hiring 355

Sales Hiring Scale Sales Payments 355

SaaStr

FEBRUARY 18, 2022

Sales-driven SaaS startups end up with about half their headcount in sales and marketing. Sales doesn't. One thing that sneaks up on you in SaaS is just how many sales, marketing and revenue professionals you are going to need: First it sneaks up on you in the early days because the initial tiny team become so efficient.

Scale 352

Scale Sales Hiring Scaling Headcount 352

SaaStr

JANUARY 5, 2024

In the latest episode of CRO Confidential, host Sam Blond, partner at Founders Fund and former CRO at Brex, sits down with Ashley Kelly, VP of Global Sales Development at Rippling. For context – Ashley had previously helped Sam scale Brex’s outbound sales from $2M to over $300M in ARR as Senior Director of SDR.

Sales Hiring 316

Sales Hiring Sales Recruiting Scale Outbound Sales Team 316

SaaStr

AUGUST 15, 2024

Robbie O’Connor, the GM EMEA at Notion and the first European hire at Asana and Dropbox takes the stage at SaaStr Europa to talk about the building blocks required to scale GTM teams and operations. Unlike product-led or sales-led growth, Notion is focused on community-led growth. You can get this wrong.

Scale 314

Scale Sales Hiring Scaling Innovation 314

SaaStr

FEBRUARY 3, 2021

Ah, the first sales rep. Being the first salesperson into a start-up in a rewarding — but very tough job: Your Founder Boss likely will never have managed a salesperson before. Whichever founder was doing sales, likely thinks that may be the way to do sales going forward. The sales “hacker”. Or vice-versa.

Sales Hiring 279

Sales Hiring Startup Sales SaaS 279

SaaStr

JANUARY 21, 2020

Justin Welsh, former SVP of Sales at PatientPop explains how he started in SaaS in 2009 as the second sales hire at Zocdoc. Justin used Sales Culture to grow a successful PatientPop team to 140 employees and 55 million in revenue. Justin Welsh | SVP Sales @ PatientPop. Want to see more content like this?

Sales Recruiting 332

Sales Recruiting Sales Hiring Scale Sales 332

SaaStr

APRIL 30, 2024

How do you build GTM efficiency in SMB sales? Lesson #1: Just Say No Once he joined, Kyle quickly discovered that Owner had a leaky bucket and had either bad or no targeting on prospects, was closing a lot of poor-fit customers, and there were a lot of miss set expectations from sales so customer handoff was sketchy at best.

Scale 306

Scale SMB Sales Hiring Sales 306

SaaStr

AUGUST 9, 2024

A case study in the book In the Age of the Smart Machine, The Future of Work and Power discusses work at paper mills in the mid-1980s as that wave of computation came into industrial processes. Before computers, intuition was a key part of managing paper mills. Determine the skills you want and how you’ll discover them in an interview.

Scale 296

Scale Sales Hiring Scaling Startup 296

SaaStr

APRIL 19, 2019

What are a SaaS startup’s first 100 hires? In our NEW Ultimate Guide For Scaling, Sales and Raising Capital: 100 SaaS Questions Answered , we compile the most helpful, tactical advice to help you scale your startup. This book is page after page of life-changing SaaS advice. How does a CEO/founder/owner pick his salary?

Scale 54

Scale Sales Hiring Scaling Sales 54

SaaStr

AUGUST 7, 2020

A few factors that contribute to high-performing sales teams: High quota attainment. The best startups invest in their sales teams and work hard so most of the reps hit and exceed quota. It does mean a well-oiled machine that hires strong reps of all backgrounds, and gets them the help and training so they can scale up and succeed.

Sales Hiring 363

Sales Hiring Scale Sales Recruiting Compensation 363

SaaStr

DECEMBER 13, 2021

It’s a bit of a bummer than oftentimes, once you finally hire a few great VPs at $1m, $2m, $3m ARR … and they do a great job … that they then don’t scale. Either by yourself, or with a Sales Ops / Marketing Ops / Some Sort of Ops leader under you. Inability to hire great Directors / managers under them.

Scale 354

Scale Sales Recruiting Sales Hiring Scaling 354

SaaStr

MARCH 11, 2021

Congratulations on finally hiring your VP of Sales! There are 3 general options: Your VP of Sales is responsible for net new revenue only. Post-sales, other than upsell which adds to net new revenue for this year, is someone else’s job. Your VP of Sales is responsible for the ARR target for the end of the year.

Sales Hiring 279

Sales Hiring Metrics Sales Churn 279

SaaStr

JULY 20, 2024

Dedicated Slack Channel For Every Metric From the early days at Secureframe, they have had a dedicated Slack channel for every metric: every net new sale, every expansion, every churn, and every expense. So, as you’re considering hiring your VP of Sales or Engineering, find a great executive recruiter to work with and eat the bill.

Sales Recruiting 304

Sales Recruiting Sales Hiring Scale Engineering 304

SaaStr

JANUARY 27, 2021

“Give the VP of Sales More Time” This is always terrible advice. If a VP of Sales can’t improve things in one sales cycle or less — she never will. In one sales cycle, or less. Don’t hire some junior marketing person that can’t really get you more leads. More on that here.

Part-Time VPE 348

Part-Time VPE Sales Hiring Scale Sales Recruiting 348

SaaStr

FEBRUARY 28, 2022

A few ideas on how to help the sales team make this your best year so far: Hire dedicated sales / revenue ops. Many of you will have little to no dedicated help in sales operations , even up to $10m ARR or beyond. If that’s you, or your VP of Sales, or even your VP of Marketing … it can sort of work for a while.

Scale 246

Scale Sales Hiring Sales Enterprise 246

SaaStr

JANUARY 12, 2024

We just wrote up how some of the biggest changes of SaaS are now coming, specifically in Customer Success and Sales. ” Prediction #3: CSM Hiring Doesn’t Bounce All The Way Back Things are bouncing back, in 2024, not all the way back, so efficiency still matters. They paused hiring for a year (rather than cut) and got profitable.

Sales Hiring 323

Sales Hiring Customer Success Scale AI 323

Predictable Revenue

AUGUST 1, 2022

Appointment setting is the best way to scale your outbound sales efforts. Learn our top tips for booking more meetings and hiring sales development reps. The post Booking Sales Meetings: Everything You Need To Know appeared first on Predictable Revenue.

Sales Hiring 147

Sales Hiring Scale Sales Development 147