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

APRIL 1, 2023

On the hiring side, it often seemed like you just couldn’t hire anyone. Everyone was hiring everyone, anyone, back in mid-2021. This data from Carta helps illustrate it: So we cut corners. We hired job hoppers that never stayed anywhere for more than 18 months for leadership roles. No time, didn’t want to know.

Sales Hiring 317

Sales Hiring Investment Leadership Startup 317

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. But often, they don’t really have all the data and metrics, or even really know what they are getting themselves into. You’re still going to hire VPs with some of these flags.

Sales Hiring 362

Sales Hiring Scale Interviewing Startup 362

SaaStr

JANUARY 12, 2025

4: What Really Works When Hiring VPs, and How M&A Really Works, with HubSpot Co-Founder and Chair Brian Halligan + Jason Lemkin #5: Whats Better, X/Twitter or LinkedIn? And 10%-12% of Ones That IPO. #4:

Sales Hiring 286

Sales Hiring Scale Scaling Revenue 286

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 253

Sales Hiring Scale Venture Capital Sales 253

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 183

Scale Sales Hiring Scaling Revenue 183

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 5, 2025

Here are the five channels that worked for Rupa: Search Engine Optimization (SEO) Social Proof and Trust Building Educational Partnerships and Rupa University Conferences and Event Sponsorships Outbound Sales and Data Quality Lets dive into each. Find trending topics, hire experts, and create the best content available for that topic.

Scale 233

Scale AI Search Sales Hiring Acquisition 233

SaaStr

MARCH 22, 2022

This requires effort from your entire organization, and Handshake VP, Employer Partnerships Jessica Peluso outlines some changes that you can make to your brand, and your application, interview, and offer process that will help find the talent you are trying to attract and hire. Below is the transcript of Jessica’s session. Hi everyone.

Sales Hiring 265

Sales Hiring Sales Recruiting Scale Sales 265

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

MARCH 12, 2025

The 4 Things Most Founders Get Wrong About Marketing: “We’re a product company, not a marketing company” – The hard truth is that 9 out of 10 B2B companies spend more on sales and marketing than R&D. In reality, effective marketing is deeply analytical and data-driven, with clear KPIs at every funnel stage.

Sales Hiring 208

Sales Hiring Marketing Technical Review Underperforming Technical Team 208

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

JANUARY 27, 2023

As the past few years have demonstrated, it’s wise to expect the unexpected, especially when it comes to hiring. In particular, hiring for your sales team is critical in an uncertain economic outlook. Additionally, sales professionals looking for a new role should choose their next company wisely.

Sales Recruiting 244

Sales Recruiting Sales Hiring Scale Compensation 244

SaaStr

FEBRUARY 2, 2023

Product marketing can be difficult, and managing product launches and rollouts can be complex. Your sales rise to a very high level You may realize that your sales are reaching high levels, but at the same time, you may encounter a situation where there needs to be more structure or control in your sales process.

Sales Hiring 264

Sales Hiring Product Marketing Scale Marketing 264

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

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 192

Scale Sales Hiring Scaling Headcount 192

SaaStr

APRIL 13, 2025

Integration with underlying systems of record : At Rippling, all products tap into employee data, unlocking unique capabilities. This structure enables a seamless experience that starts when a company hires someone. His rationale: Training capacity : Sales teams can only absorb so much product knowledge.

Startup 163

Startup Sales Hiring Underperforming Technical Team Cloud 163

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 219

AI B2B ChatGPT Scale 219

SaaStr

APRIL 8, 2022

There's always a 50% chance that manager you need to hire already works for you. So Gong has a new report on Sales Talent and there’s some good data in here. And you have to try to source 50% of your managers from within. More on that here: Time To Staff Up Your First Directors and Managers?

Sales Hiring 313

Sales Hiring Sales Startup Management 313

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. Typically, sales leaders have reduced quota somewhere between 10-50%. You can download the survey here.

Sales Hiring 334

Sales Hiring Sales Forecasting Travel 334

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

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 307

Scale SMB Sales Hiring Sales 307

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

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

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

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. Hire more CSMs.

Scale 322

Scale Sales Hiring Sales B2C 322

SaaStr

FEBRUARY 23, 2021

I want to spend a few posts and some time on sales comp plans for early-ish stage SaaS companies (up to say $20m in ARR). Because almost all the sales comp plans you are going to read about, and learn about are great — for SaaS companies that are well post-Scale. That work great for Salesforce, or Box. Just the top rep.

Sales Hiring 329

Sales Hiring Scale Sales Business Model 329

SaaStr

DECEMBER 14, 2021

Kazuki Ohta, CEO & Founder at Treasure Data, shares his company’s story of how pivoting at the right time saved their business and accelerated their growth to $100 million ARR. When it launched in 2011, Treasure Data’s positioning was a Hadoop-based big data warehouse in the cloud. The Platform: $0 – $5 Million ARR.

Sales Hiring 313

Sales Hiring Data AWS Leadership 313

SaaStr

AUGUST 9, 2024

Hiring for Customer Success When Braze was looking for their first customer success hires, you couldn’t find a CSM with seven years of experience in software because those people didn’t exist yet. Every incremental hire with a small team matters, so it’s worth being clear on what you want.

Scale 297

Scale Sales Hiring Scaling Startup 297

Tom Tunguz

APRIL 28, 2020

How do you benchmark a sales organization in a time like this? Using data across 10m telephone calls, Jim highlights how the coronavirus is changing sales team performance. Timeline risk, the likelihood a sale drags to a close, has doubled to about 2% of calls. An additional 2% mention hiring freezes.

Benchmarks 331

Benchmarks Sales Hiring Sales Data 331

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 286

Sales Hiring Travel Sales SaaS 286

SaaStr

JANUARY 31, 2022

Having learned from thousands of customers and prospects, Sarah Lash, Envoy’s head of enterprise sales, will talk about what it takes to guide and scale enterprise sales programs during an uncertain future. In my first six months at Envoy , I grew the sales team from six to 17. Combine Strategies To Drive Sales.

Sales Recruiting 246

Sales Recruiting Sales Hiring Scale Enterprise 246

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. Timing is also essential. You can get this wrong.

Scale 314

Scale Sales Hiring Scaling Innovation 314

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. Back in 2015, when didn’t have the data or NRR or GRR of 115 public SaaS companies. If there were one or two metrics or data points that Nick learned at Gainsight by sitting in on board meetings, what were they?

Sales Hiring 323

Sales Hiring Customer Success Scale AI 323

SaaStr

NOVEMBER 20, 2024

Other Learnings in the GTM Journey GitHub has had to adjust to new sales stages and new buyer personas. There was a proliferation of conversations centered around legal, privacy, and models that took much longer in these sales stages than ever experienced. You might have to take a new approach to feedback to keep up with demand.

Scale 265

Scale AI Scaling Marketing 265

SaaStr

AUGUST 4, 2021

Ask them what those top 3 are before you hire them. So with that, let’s add to our classic Top 10 Interview Questions for a VP of Sales and also our Top 9 Interview Questions for a VP of Customer Success with … Our Top 10 Interview Questions for a VP of Marketing! How have you worked with the sales team in the past?

Interviewing 356

Interviewing Sales Hiring Marketing Branding 356

SaaStr

JANUARY 30, 2023

They focused on building a payment platform that empowers international talent and independent contractors to get paid on time in a compliant way while also ensuring that companies can hire international talent and make payments efficiently. Use your data to inform. Identifying a direction is just the starting point. Trust the process.

Sales Hiring 279

Sales Hiring Payment Services SaaS Payments Scale 279