SaaStr

MARCH 29, 2020

We put out a thread here you can click on for a deep dive on 100s of SaaS openings from SaaStr CEOs: Are you hiring? Respond with a link to your top hire to make, etc. They include: Auren Hoffman and Safegraph hiring 3 in sales and 5 in engineering. Matt Mullenweg and Automattic hiring 100s. — Jason ?InItTogether?

Sales Hiring 298

Sales Hiring SaaS SMB Content Marketing 298

SaaStr

FEBRUARY 22, 2022

Ok we’ve talked a bit more on SaaStr over the years on how to hire a Great VP of Sales , but hiring a Great VP of Marketing is just as important. Maybe in some ways more so, in that you can generally hire a great VP of Marketing earlier. Do you make the hire now? Not just in sales. What do I mean?

Sales Hiring 307

Sales Hiring Growth Hacking B2C SMB 307

SaaStr

SEPTEMBER 19, 2023

based SMB sales positions. SaaS sales execs with even a little bit of experience at other SaaS companies are looking for higher and higher OTEs, often with lower effective attainment and high support costs. based sales reps often aren’t really willing to work, or excel, at sub-$100k OTEs anymore. customers?

SMB 318

SMB Scale Sales Hiring Sales 318

SaaStr

APRIL 30, 2024

How do you build GTM efficiency in SMB sales? While this title is SMB-oriented, the advice applies to Mid-Market and Enterprise, too. You shouldn’t be adding a bunch of sales reps or spending a bunch of money on marketing if the economics aren’t sustainable. Kyle made this mistake in his first startup.

Scale 307

Scale SMB Sales Hiring Sales 307

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

JULY 12, 2022

One of the first what How to Hire a Great VP of Sales at the New York Enterprise Tech Meet-Up (thank you to John Lehr and Work-Bench for setting this up). The Number One Thing You Can Do to Accelerate Your Business Post-Initial Traction is Hiring a Great VP of Sales. I don’t know anything about sales.

Sales Hiring 291

Sales Hiring Part-Time VPE VP of Engineering Sales Recruiting 291

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

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. Waiting too long to start their enterprise planning.

Enterprise 244

Enterprise Sales Hiring Scale Outsourced Development 244

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

FEBRUARY 24, 2022

I’ve recently had several different conversations with founders looking to hire “PLG experts”. One wanted to hire “Mr/Ms PLG” to make their product more viral. It’s too early in this PLG cycle to hire a “VP of PLG”. Instead: * Hire a great VP of Product with strong freemium experience. Probably in that order.

Sales Hiring 279

Sales Hiring Scale SMB Acquisition 279

SaaStr

FEBRUARY 4, 2021

One of the very first SaaStr presentations ever was How to Hire a Great VP Sales (And Not Screw It Up). One was how my First Real VP of Sales Doubled Our Net New Revenue in 90 days. Brendon Cassidy joined as our VP Sales at a tough time, as we’ve discussed before, as we were coming out of our Year of Hell.

Sales Hiring 347

Sales Hiring Sales SMB Pricing 347

SaaStr

JUNE 8, 2024

So David Obrand, CEO of Salesloft, had a great post the other day on consistency being one of the biggest challenges with enterprise sales. In SMB sales, you see the variance in performance among reps really fast, and you can take action fast. That’s the nature of a very short sales cycle. The Best VPs of Sales?

Sales Hiring 300

Sales Hiring Scale Sales SMB 300

SaaStr

MARCH 18, 2021

We’ve talked a lot about hiring a VP of Sales at SaaStr , and if you hire a stretch VP of Sales (as most of you will) … how much you can stretch. A related question is — just how quickly can you gain the requisite experience to be a true first time VP of Sales? Month 6: promoted to first SMB rep.

Sales Hiring 307

Sales Hiring Sales Recruiting SMB Sales 307

SaaStr

JANUARY 19, 2025

And we’ve done several great live Workshop Wednesdays with top CROs and VPs of Sales in Vertical SaaS in particular recently that are all A+ and worth watching: #1. It takes getting out in the field, and creating a ton of true value — before the sale. #2. See you there! How Kyle does it here: #3. How Kyle does it here: #3.

Scale 189

Scale Sales Hiring Scaling SMB 189

SaaStr

NOVEMBER 6, 2021

The other day Brendon Cassidy, the first head of sales at LinkedIn and the first VP of Sales at $10B Talkdesk, Adobe Sign / EchoSign, and more — and now co-CEO of Cosell — and I caught on what’s changing in the Sales Playbook for 2022. Even in SMB and mid-market. Well in most cases.

Scale 342

Scale Sales Hiring Sales SMB 342

FastSpring

FEBRUARY 6, 2025

If you’re running a smaller digital business, you may find it challenging to hire great talent. 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.

SMB 99

SMB Sales Recruiting Branding Sales Hiring 99

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

JULY 27, 2022

If a SaaS business hopes to win over the SMB market successfully, it will need a precise GTM approach. Founded in 2015, PayFit is a software company that empowers entrepreneurs and SMBs to digitize payroll and HR processes. Secret 1: A Self-Serve Product is Non-Negotiable For SMBs.

SMB 244

SMB Sales Hiring Scale B2C 244

SaaStr

JULY 11, 2023

How do you win with a high-velocity sales strategy in a fast-moving, competitive market? In a special session of Workshop Wednesday, Gorgias Founder & CEO Romain Lapeyre and Gorgias VP of Sales & Partnerships Aasif Osmany share their learnings, advice, and hacks for optimizing your sales process. Sign up for free.

Sales Hiring 203

Sales Hiring SMB Sales Recruiting Payment Methods 203

SaaStr

JULY 1, 2024

It’s less jack-of-all-trade hires, so the knowledge and questions they’ll ask will look a lot different. Either way, ensure the demand gen team sits down with sales and decides which accounts to go after. Either way, ensure the demand gen team sits down with sales and decides which accounts to go after.

Sales Hiring 306

Sales Hiring Scale SMB compliance 306

SaaStr

AUGUST 26, 2022

As SaaStr Europa 2022 drew to a close, attendees took one more opportunity to ask Jason questions about topics like how to navigate the current market, the future of work, playing in a crowded space, and hiring your first VP of Sales. It was funny for Henry to say he segmented his sales team at 80 million in ARR. Transcript.

Sales Hiring 246

Sales Hiring Scale Sales Recruiting Scaling 246

SaaStr

JANUARY 21, 2022

Dorian Stone , Head of Organizations Revenue at Grammarly, is here to share lessons from his experience of scaling the company from consumer to SMB to Enterprise to help you steer your expansion efforts in the right direction. The admin, influential decision-makers, and consumer sales reps can be the same people in a Consumer or SMB setting.

Scale 246

Scale SMB Enterprise Sales Hiring 246

SaaStr

OCTOBER 30, 2021

Their CEO will join us at SaaSr Scale 2021 on December 15 to talk about using data to get to 10,000 SMB customers! I asked Aasif Osmany to share his learnings as a top-performing SMB VP of Sales, below. Together we combed through AngelList and found companies that we saw potential in, however, most were not hiring.

Scale 291

Scale Sales Hiring Sales SMB 291

SaaStr

FEBRUARY 9, 2024

Everything from hiring on the GTM side to layering in a sales-led motion into PLG. Let’s dive into what’s making that hybrid model successful: PLG and Sales Led? Given this, you must understand the role that each facet of the business plays in promoting that product, from marketing and sales to customer service.

Scale 321

Scale Sales Hiring Sales Marketing 321

SaaStr

MARCH 28, 2025

Hire a dedicated partnership manager from day one. Treat this like a sales pipelinetrack leads, co-selling efforts, and revenue generated from these partnership. Expect your sales cycle to double when working with partner s. It takes time to build trust, align incentives, and close deals together.

Scale 147

Scale Sales Hiring SMB Enterprise 147

SaaStr

JULY 28, 2024

Hire a Very Good VP of Sales that has sold at your “high end” price point. If you can make this hire now — you will do much, much better. More here: The 48 Types of VP Sales. Make Deadly Sure You Hire the Right One. #2. Make Deadly Sure You Hire the Right One. #2. Get zen about longer sales cycles.

Sales Hiring 286

Sales Hiring Scale SaaS SMB 286

SaaStr

DECEMBER 12, 2023

Keybanc and Sapphire have some great overall metrics here : Overall, the media AE closes $750,000 a year, and that’s actually up from 2022 — mainly due to hiring freezes and contractions. Enterprise reps tend to close more ($1m+), and SMB reps less (maybe $500k), with $750k net new bookings per year the median.

SMB 336

SMB Sales Hiring Enterprise Metrics 336

SaaStr

NOVEMBER 16, 2021

You’ll need to hire aggressively to get to the next level and continue that rapid growth. But what roles should you hire for, and what will your org chart look like at each stage? In 2008, he founded Yammer, an enterprise software company that David grew to 500 employees and $60 million in sales. Head of Sales.

CTO Hire 291

CTO Hire Sales Hiring Sales Recruiting CTO 291

SaaStr

OCTOBER 26, 2023

Getting off the ground is one thing — an easy pitch of being an HR tech startup focused on improving hiring. Hiring is complicated, so you have to build a lot of software to get to $200M ARR. In a year like this, SMB is doing worse, with a lot more churn and startups going out of business. On websites.

Sales Hiring 287

Sales Hiring AI SMB Scale 287

SaaStr

MARCH 17, 2021

The other day, I met with a great founder who talked with me about how he was about to top his VP of Sales. As founders, we often get obsessed with “right timing” hires. You definitely don’t want to hire some SVP of Sales at Salesforce to come be your VP of Sales at $1m in ARR — that we can all agree on.

Sales Hiring 313

Sales Hiring Sales Recruiting Scale SMB 313

SaaStr

JUNE 20, 2023

Dear SaaStr: What remarks have a salesperson said to you that lost them the sale? Sales is there to serve. If sales was routed the wrong lead, that’s the company’s fault, not the prospect’s. I’m basically an SMB these days. And let especially SMBs out if you don’t deliver for them. Yes, you have to do that.

Sales Hiring 274

Sales Hiring Scale Sales SMB 274

SaaStr

DECEMBER 26, 2020

Even once you hit just $2m-$3m ARR — fairly early — the trade-offs start to become clear for startups with customers both Smaller and Larger: Small customers consume just as many sales, success, and marketing resources. 1000 small customers may be a death of small cuts to your sales and success teams. Probably more.

SMB 361

SMB Sales Hiring Marketing Enterprise 361

SaaStr

MAY 5, 2022

What are some of the foundational ways sales leaders can think about building their sales teams as their company continues to expand and grow? There’s no shortage of ways to tackle this challenge, but one thing is clear: build sales teams thoughtfully and intentionally. Principle #1: Ownership is Key.

Scale 246

Scale Sales Hiring Scaling Sales 246

SaaStr

JULY 24, 2024

Sign #2: You’re Too Slow to Hire VPs If you want to gauge momentum in a startup, see how quickly they hire VPs. Is it easy to hire mercenary VPs when you’re growing 500%, or you’ve raised $100M? Maybe they made the wrong hire or entered the wrong market. The solution is hiring the right person or relaunching next quarter.

Sales Hiring 307

Sales Hiring Startup Scale SMB 307

SaaStr

DECEMBER 1, 2023

Hiring a VP of Sales isn’t new, but the conversations have evolved as the world has. SaaStr’s own Jason Lemkin shares the top 10 mistakes he sees during the hiring process during Workshop Wednesday, held every Wednesday at 10 a.m. The last 18 months have seen the biggest changes in the VP of Sales in his SaaS career.

Sales Hiring 163

Sales Hiring Sales Recruiting Sales Interviewing 163

SaaStr

SEPTEMBER 15, 2023

Big Bet #2: Find Tomorrow’s Great Anglers — Hire Talent With A Learning Mindset In 2010 and 2011, San Francisco was the place for SaaS talent. So, if he wanted to hire customer support, it could be a biomechanical engineer. Instead of hiring for skill, he focused more on core traits like empathy, patience, and being detail-oriented.

Sales Hiring 290

Sales Hiring Scale SMB SaaS 290

SaaStr

NOVEMBER 18, 2020

Mistake #1: Hiring Too Inexperienced and Junior Managers and “VPs” Stretch VPs can do amazing things if you get it right. Hiring someone who’s never really been a manager at all, for a management role, for a true “owner” role … is usually a stretch too far. More on that here.

Sales Hiring 363

Sales Hiring Scale SaaS Enterprise 363