SaaStr

AUGUST 28, 2020

I know we’ve hit a number of these points individually before on SaaStr, but after getting asked about the top mistakes hiring your first sales team so many times over the years, I thought it would be worthwhile to assemble a Top 10 List. Yes, you may be terrible at sales. It’s sales, after all. Here’s my Top 10 list: #1.

Sales Hiring 332

Sales Hiring Sales Recruiting Scale Sales 332

SaaStr

FEBRUARY 12, 2022

What was the first warning sign your VP of Sales wasn't going to work out? A new VP of Sales doesn’t always double sales in 30 days — although it can happen in SMB sales. The old playbook does help, but every great VP of Sales knows they quickly have to evolve it to any new role.

Sales Recruiting 274

Sales Recruiting Sales Hiring Sales SaaS 274

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? Do the diligence here to make sure she’s really been able to recruit at least a few successful reps. Has she sold as your price point, approximately ?

Sales Recruiting 284

Sales Recruiting Sales Hiring Scale Development Team Review 284

TechEmpower SaaS

MARCH 4, 2024

Key Functions with High Impact Generative AI is revolutionizing sales by enabling dynamic pricing and personalized customer interactions, boosting conversion rates and customer satisfaction. Post-sale, AI analyzes customer data to improve service and loyalty, making it a cornerstone of modern sales methodologies.

Generative AI 443

Generative AI CTO Hire AI Sales Recruiting 443

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 is hard.

Sales Recruiting 300

Sales Recruiting Sales Hiring Technical Review Scale 300

SaaStr

JUNE 21, 2023

They hired their first VP of Sales with a wonderful pedigree and experience at some of the hottest startups. because they needed to rebuild the sales team. They rebuilt the sales team and closed some big deals. A good executive recruiter is like a real estate agent or matchmaker. A good recruiter is worth it.

Sales Recruiting 293

Sales Recruiting Sales Hiring Underperforming Technical Team Pricing 293

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. Do the diligence here to make sure she’s really been able to recruit at least a few successful reps. Has she sold as your price point, approximately ? This is a tough skill to develop.

Sales Hiring 274

Sales Hiring Sales Recruiting Scale Development Team Review 274

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 hire a VP of Sales to sell before you prove you can do it yourself.

Sales Hiring 274

Sales Hiring Sales Recruiting Sales Branding 274

SaaStr

FEBRUARY 26, 2021

Brendon Cassidy, my VP of Sales wrote a version of this piece a while back. I though an updated version of this would be good for founders thinking about hiring a VP of Sales … VPs of Sales themselves … and VPs-to-be to read — Jason, ed. … 10 Rules to Being a VP of Sales in a Startup.

Sales Hiring 301

Sales Hiring Sales Recruiting Startup Sales 301

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. Work with Great Executive Recruiters ”The first time I saw an invoice for an executive search, I think I had a heart attack,” Shrav joked.

Sales Recruiting 299

Sales Recruiting Sales Hiring Scale Engineering 299

SaaStr

JUNE 24, 2022

Your best sales reps can close so much more than your average rep. Move the bottom 10% out and give the best leads to your top performer, and watch sales go up 20%. The best VPs of Sales design comp plans so the team never wants to leave. You should be striving for zero voluntary attrition on your sales team.

Sales Recruiting 281

Sales Recruiting Sales Hiring Scale Customer Success 281

FastSpring

FEBRUARY 6, 2025

In this episode of Growth Stage, we interview Lizzie Mintus Founder and CEO of Here’s Waldo Recruiting and host of The Heres Waldo Podcast about her thoughts on: The most effective recruiting strategies for SMBs. So during the intro, I kind of talked about how you run here’s Waldo recruiting.

SMB 106

SMB Sales Recruiting Branding Sales Hiring 106

SaaStr

MAY 24, 2022

Yes, public stock prices are way down, which creates a lot of pressure in general and on venture fundraising in particular. Even the very best VPs of Sales I know admitted to lowering the bar a bit on their sales teams, when I quietly pushed them. A related post here: How To Get Better at Recruiting. (We We All Need To).

Sales Hiring 320

Sales Hiring Sales Recruiting Interviewing Startup 320

SaaStr

SEPTEMBER 28, 2024

Kyle Norton CRO of Owner is kicking off a new podcast for Pavillion with revenue leaders, and we were lucky enough to be guest #001 here: It’s a great convo on many SaaStr themes — but from the perspective of a VP Sales / CRO. Never play the blame game As a revenue leader, it’s crucial we take accountability for sales performance.

Technical Review 298

Technical Review Sales Hiring Sales Recruiting Revenue 298

SaaStr

SEPTEMBER 5, 2022

Going from sales-led to PLG is doable, but it is not easy. Sales-led organizations struggle to adapt to a PLG mindset.”. Let’s use sales-led organizations as a comparison point. If a company has started out with a heavy sales focus, its onboarding process within the actual product may not be intuitive enough for customers.

Sales Recruiting 284

Sales Recruiting Business Pricing Churn 284

SaaStr

DECEMBER 28, 2019

Enough with the excuses for not having hired your real VP of Sales, or that VP of Engineering, or whatever. Hire a real recruiter. Increase Pricing For New Customers in January — The Right Way. Pricing is a nuanced topic. And if you don’t think you can support higher pricing yet, that’s OK.

Part-Time VPE 325

Part-Time VPE Sales Hiring Scale Sales Recruiting 325

SaaStr

APRIL 5, 2021

Once the players in a new market get pretty big themselves, they’ll ultimately most likely raise prices. And at a sales perspective, they’ll move to optimizing revenue per lead, over closing every possibly lead. Harder to Recruit. You’ll have to develop a very lean sales culture. More on that here.

Scale 294

Scale Sales Recruiting Underperforming Technical Team Pricing 294

Kellblog

MARCH 17, 2020

Rephrasing Lewis Carroll, “if you don’t know what you’re recruiting for, any candidate looks great.” ” I liken executive recruiters to Realtors. ” That know-not-what, by the way, is that it’s for sale. Let’s switch to executive recruiting. Nice to Have. 4 bedrooms.

Sales Recruiting 86

Sales Recruiting Sales Enablement Startup Pricing 86

Tom Tunguz

NOVEMBER 24, 2018

You might have a few account executives and a sales leader in place; maybe some revenue and a handful of customers. The sales team costs real money, and the question before the company is: how do you know what quota plan to assign to the account executives? Stage 1: Management by Objectives.

Compensation 195

Compensation Sales Recruiting Sales Hiring Scale 195

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. At twice the price. “The Leads are There, the Problem is the Sales Team.” More on that here.

Part-Time VPE 348

Part-Time VPE Sales Hiring Scale Sales Recruiting 348

SaaStr

APRIL 30, 2022

Customer acquisition is basically how much do you spend in terms of sales people, sales team, and in terms of marketing to acquire a new customer. The key here is knowing what your sales model is. And there are basically two sales models out there. Kind of extreme sales models out there for SaaS businesses.

SaaS Payments 246

SaaS Payments Metrics Payment Methods Scale 246

OpenView Labs

APRIL 29, 2021

Recruiting top talent is the common denominator across all scaling startups. Nine out of 10 founders and CEOs I connect with are involved in recruiting on a weekly, if not daily, basis. Many of them are learning on the fly and trying to juggle being CEO and Chief People Officer/Lead Recruiter/Brand Evangelist all at once.

Sales Recruiting 81

Sales Recruiting Outsourcing Services Sales Hiring Scale 81

SaaStr

NOVEMBER 12, 2022

The main issue is price. Growing too slowly after Initial Traction at a minimum means a lot of VCs will rule you out at any price. Lack of a (at least the Genesis of a) Management Team. You never have a perfect management team until you are at $10m+ ARR, at the earliest, in 98/100 cases. I don’t, but many do).

Scale 343

Scale Sales Recruiting Machine Learning Artificial Intelligence 343

SaaStr

OCTOBER 3, 2022

What is the pricing? Imagine a coverage model, from end to end, for the full customer life cycle: from demand generation to sales to post-sales. Sales Cycle. This includes everything from inside sales to account executives to strategic asset allocation. Post Sales. What is the product strategy?

Scale 273

Scale Sales Hiring Sales Recruiting Scaling 273

SaaStr

JULY 25, 2021

They talked about product adoption, sales alignment, freemium models and lessons they have learned throughout their successful SaaS careers. As two CEO who love the art of sales and scaling, this one really was special. Recruiting is easier, but the things that don’t change are customers don’t care.

Sales Recruiting 261

Sales Recruiting Sales Hiring Scale VP of Engineering 261

SaaStr

JULY 1, 2021

I want to come be your VP of sales and, you’re going to meet me for the first time. Spencer : For me, the key things for a VP of sales is, “OK, tell me about your best reps. We’re trying to recruit someone that’s way above our weight class, so that we can actually scale. You hire a search firm.

VP of Engineering 293

VP of Engineering Sales Hiring Sales Recruiting Underperforming Technical Team 293

SaaStr

OCTOBER 3, 2023

It’s so, so easy to stand out in recruiting if you’ve actually done your homework. I spent a week preparing and about halfway into that I realized that something was off about the pricing page, so I redid it from scratch and presented towards the end of the “workshop” Chalk and cheese I was told afterwards.

Interviewing 273

Interviewing Sales Hiring Sales Recruiting Consulting 273

Clouded Judgement

FEBRUARY 7, 2025

Signal can come from many places (sales team notes, customer support tickets, etc) IT Incident Management: Similar to the security alert example. Group related incidents or tickets by severity to help prioritize. Revenue multiples are a shorthand valuation framework.

Systems Review 144

Systems Review Cloud AI Artificial Intelligence 144

Tom Tunguz

APRIL 14, 2019

These startups use machine learning to disrupt an industry traditionally dominated by agencies: law, accounting, recruiting, translation, debt collection, marketing…the list is long. Second, how to price the product relative to the competition? These are two short term pricing headwinds.

AI 203

AI Sales Recruiting Underperforming Technical Team Machine Learning 203

SaaStr

JULY 1, 2020

An open discussion with Sam Blond, CSO at Brex, and Kristen Habacht, VPS at Atlassian, about adjusting their sales process during Covid-19. Kristen Habacht runs EDR sales at Atlassian, which I got a check today, $40 billion-$50 billion company. She manages a huge global team. Four, people in the sale? Jason Lemkin: None.

Merchant Services 259

Merchant Services Scale Sales Recruiting Sales 259

Kellblog

JUNE 27, 2020

I’ve worked with several startups that fell into the following pattern: Selling a SaaS application at a healthy price (e.g., The problem is the company is not charging the appropriate price for the services needed. If you sell: A recruiting app, running your first recruiting campaign. 100K to $200K ARR).

Consulting 144

Consulting Sales Recruiting Sales Hiring Startup 144

SaaStr

NOVEMBER 12, 2019

I started a software company in college to make it easy to update websites called Content Management Software Now, and I had this idea for Pardot, I wanted to make it easy for marketers to run campaigns online and measure their results. SalesLoft, why was that Pardot, I tried to recruit this guy, Kyle Porter, to come run sales at Pardot.

Sales Recruiting 201

Sales Recruiting Scale Outsourcing Services Sales Hiring 201

SaaStr

AUGUST 7, 2020

359: The Secrets to Vertical Growth, What it Really Takes to Build a $1B SaaS Company with Matt Garratt, SVP, Managing Partner @ Salesforce Ventures, Trisha Price, Chief Product Officer @ nCino and David Schmaier, CEO & Founder @ Vlocity. Trisha Price. They need fewer sales as a percentage of overall employees.

Payment Solutions 215

Payment Solutions Pricing Payments Payment Services 215

Sales Hacker

AUGUST 20, 2024

As Upland’s Chief Revenue Officer, Matt Breslin oversees customer success, demand generation and communications, sales, revenue enablement, and revenue analysis, supporting our Shared Services Organization. Matt started his career as a Certified Public Accountant for Price Waterhouse and Kraft Foods. Brought to you by IPS.

Sales Recruiting 123

Sales Recruiting Software Review Software Sales 123

Sales Hacker

APRIL 8, 2024

In the competitive arena of B2B sales, mastering the art of prospecting is key to ensuring a healthy sales pipeline, daily demos booked, and hitting your sales quota. Fortunately for you, we’ve sifted through the clutter and done all the legwork to bring you the top 10 sales prospecting tools. Wiza reviews 4.5/5

Scale 125

Scale Sales Recruiting B2B AI Search 125

Intercom, Inc.

SEPTEMBER 10, 2020

It’s an approach that’s served him well along the road to building the HubSpot sales team, where he was CRO for nine years. That experience led to his bestselling book, The Sales Acceleration Formula. I just don’t think sales have anything to do with product-market fit. A data-driven framework for scaling.

Scale 226

Scale Scaling Sales Recruiting Sales Hiring 226

SaaStr

JANUARY 24, 2024

Sales reps were hosting 4-6 calls daily but most of these calls were early demos or top-of-funnel discovery calls Sales was closing really small deals on one end while talking to really large companies with hundreds of thousands of people on the other. Define your ICP as early as you can and segment your sales team accordingly.

Scale 273

Scale Sales Hiring Scaling Revenue 273