SaaStr

JUNE 13, 2025

” I saw a term sheet the other day where a leading VC firm reserved $1m of the round … for hiring a “VP of AI” Leadership teams scrambling to post job descriptions for “Head of Artificial Intelligence.” Would you hire a “VP of Internet” in 2010? Think about it.

Sales Hiring 249

Sales Hiring Artificial Intelligence AI Sales Recruiting 249

SaaStr

JULY 23, 2025

Managing revenue operations (RevOps) in a SaaS company is all about aligning sales, marketing, and customer success to drive growth efficiently. Align Sales, Marketing, and Customer Success These teams need to work as one unit. If you can afford it, hire this role even earlier.

Sales Hiring 257

Sales Hiring B2B Scale SaaS Payments 257

SaaStr

JUNE 23, 2025

Should I Stop Hiring? But … if growth remains strong and the burn rate overall is manageable and isn’t growing out of control, maybe don’t fully tap the brakes. That’s not a reason to stop or slow hiring. Evaluate Your Sales Efficiency Are your sales reps hitting quota?

Sales Hiring 175

Sales Hiring Scale Investment Acquisition 175

SaaStr

JUNE 1, 2025

Dear SaaStr: What are the most common mistakes first-time founders make when building enterprise sales teams? The most common mistakes first-time founders make when building enterprise sales teams are surprisingly consistent. Heres the breakdown: Hiring a VP of Sales Too Early : This is a classic.

Outsourcing Services 194

Outsourcing Services Sales Hiring Scale Enterprise 194

SaaStr

JUNE 29, 2025

The Pivot : They interviewed 200 companies and 400 founders in just 6 weeks, asking one simple question: “If you’re open to hiring internationally, what are your biggest challenges?” Scaled Sales Without Revenue Operations (And Paid Dearly) The Explosion : From 2 AEs to 50 AEs in one year. ” Training was broken.

Payment Services 189

Payment Services Sales Hiring Payment Solutions SaaS Payments 189

SaaStr

JULY 11, 2025

Later, it’s about building a repeatable sales process and ensuring your infrastructure can handle the growth. Hiring the Right Team: A lot of founders wait too long to hire great VPs—VP of Sales, VP of Marketing, VP of Engineering. They hire VPs they know aren’t great, to finally get it domestically.

Scale 235

Scale Part-Time VPE Scaling Sales Hiring 235

SaaStr

DECEMBER 29, 2024

Top Posts of the Week: #1: Salesforce: Actually Were Going to Hire 2,000 Sales Execs Now To Sell AI #2: Gong: $100k Deals Take About 70 Days to Close #3: Why The Greatest Sales Teams Just Kill It On Dec 31. When Everyone Else Has Gone Home. #4:

Sales Hiring 284

Sales Hiring AI Pricing Development 284

SaaStr

OCTOBER 13, 2024

I felt part of your core job as CEO was to assemble a management team, not complain about how you couldn’t get it all done. Or didn’t want to do sales. I still believe a CEO should “do it all” in terms of building a decent management team first before hiring a COO. Hiring a strong COO between Management Team 1.0

Sales Hiring 260

Sales Hiring CTO Hire Scale Startup 260

SaaStr

MAY 29, 2025

At SaaStr + AI Summit 2025, Jason Lemkin and Kyle Norton CRO of $1B+ vertical SaaS leader Owner (where Jason is on the board) did a deep dive on AI in Sales today. This isn’t about being an AI expertit’s about demonstrating active engagement with AI tools and genuine interest in how they can transform sales outcomes.

Sales Hiring 239

Sales Hiring Underperforming Technical Team AI Scale 239

SaaStr

JULY 2, 2025

And Raaz just shared live with us exactly how she built their marketing engine from zero marketing experience to hyper-growth success. The Hiring Philosophy That Built a $23B Company “Every single person you hire should be your best hire ever. ” Raaz is obsessed with hiring. What are you talking about?”

Sales Hiring 175

Sales Hiring Marketing AI Cybersecurity 175

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 293

Revenue Scale Sales Hiring Compensation 293

SaaStr

JULY 16, 2025

Product innovation can reignite growth engines even at massive scale. They engineer business models that deliver both. Market category expansion (AI workloads driving new use cases) The SaaStr Takeaway: Don’t accept linear growth deceleration as inevitable.

Scale 267

Scale B2B Sales Hiring Acquisition 267

SaaStr

JULY 12, 2025

Over-Engineered Early Hiring and Created “Unicorn” Roles In their early days, Vanta convinced themselves they were so special that standard SaaS roles didn’t apply to them. Instead of hiring a customer success manager, they created bespoke roles that mashed together different functions. The lesson?

Sales Hiring 185

Sales Hiring Software Review compliance Sales Recruiting 185

SaaStr

FEBRUARY 7, 2025

For context,Ron has an MBA and a master’s in engineering from Stanford. His view is your sales team teaches your customers how to get value out of your product. Similar to most structures of a technical sales team. From the early days, we had a more technical sales team.” You gotta know the product cold.)

Scale 176

Scale Sales Hiring Scaling Revenue 176

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. Better to hire for your specific needs and stage. These “five-five” CMOs barely exist.

Sales Hiring 202

Sales Hiring Marketing Technical Review Underperforming Technical Team 202

SaaStr

MAY 31, 2025

Key hires like a VP of Engineering or VP of Product might get 1%-2% each. Senior engineers or designers might get 0.5%-1%. Another way to think of this stage; the first 10 or so should probably get at least twice the equity of others for joining early, if they are mission-critical hires. Junior employees might get 0.1%-0.25%.

Part-Time VPE 210

Part-Time VPE Sales Hiring Sales Recruiting Compensation 210

SaaStr

MARCH 17, 2025

Hire an Ex Post-Facto Co-Founder: This is someone who isnt technically a co-founder but acts like one. It could be a VP of Product, Sales, or Engineeringsomeone who takes ownership of a big chunk of the business and cares almost as much as you do. Prioritize Great Early Hires. If youre technical, hire someone who can sell.

Sales Hiring 247

Sales Hiring Scale Scaling Engineering 247

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 260

Scale Transportation Scaling SMB 260

SaaStr

JULY 4, 2025

Less Budget Being Routed to AI Initiatives (For Now) Tech companies are pouring massive budgets into AI initiatives – new models, AI infrastructure, prompt engineering teams. A plumbing company isn’t hiring a Chief AI Officer. At Least Right Now. Non-tech industries? They’re not there yet.

Merchant Services 323

Merchant Services SaaS Payments Payment Services Payments 323

SaaStr

JULY 5, 2025

You have to have enough to hire people to dedicate on it. ” Negotiation philosophy : “I have apples for sale. It’s a good set of people that can work together and be multidisciplinary – software, engineering, product management, strategy – a cohesive group.” net income, 111.5%

Underperforming Technical Team 239

Underperforming Technical Team Sales Hiring compliance Outsourced Development 239

SaaStr

JULY 11, 2025

Sales isn’t going anywhere in the Age of AI. OpenAI has a big sales team, Windsurf does, Anthropic has a great one. Especially the next generation of them: Perplexity has scaled to 5,000 enterprise customers with just 5 sales reps. Cursor built a $400M business with what appears to be a skeleton GTM team.

Scale 185

Scale AI Headcount Sales Hiring 185

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 229

Scale AI Search Sales Hiring Acquisition 229

SaaStr

NOVEMBER 20, 2024

Historically, the burden of customer feedback fell on the solutions engineers and CS architects. Other Learnings in the GTM Journey GitHub has had to adjust to new sales stages and new buyer personas. Sometimes, you have to say no or push them into a specific package, which is true post-sale for adoption.

Scale 261

Scale AI Scaling Marketing 261

SaaStr

JUNE 6, 2025

Whether it’s hiring a VP of Sales who’s scaled a team to $50M ARR or finding a product leader who’s built enterprise-grade solutions, the talent pool here is unparalleled. #2. From hiring to partnerships to fundraising, being here makes it easier to connect with the right people at the right time.

Sales Recruiting 225

Sales Recruiting Scale Sales Hiring B2B 225

SaaStr

JUNE 20, 2025

billion valuation after 175M round Scale AI : $29 billion valuation / “sale” with Meta’s $14.3 The Team Reality Check: Your Biggest Blind Spot Here’s the uncomfortable truth most SaaS leaders won’t admit: your current engineering team may not be equipped for AI transformation. billion in funding xAI : $6.4

AI Search 289

AI Search Artificial Intelligence AI CTO Hire 289

Sales Hacker

DECEMBER 17, 2024

As the co-founder and CEO of Intellimize (acquired by Webflow), Guy brings a unique perspective from his journey through iconic companies like Microsoft, Yahoo, and Twitter, as well as his background in aerospace engineering. It includes a breakdown of the Sales AI landscape, adoption of GenAI and Sales software across buyer groups.

Scale 102

Scale Engineering Acquisition Scaling 102

SaaStr

APRIL 8, 2025

And thus — hiring more. They they are doubling down and hiring even more to keep these gains going. Net net, if the average RevenueCat engineer is twice as efficient as before AI dev tools (and it’s not that simple. but close enough) AND they then double their hiring … now they are moving 4x as quickly.

AI 283

AI Sales Hiring Scale B2B 283

SaaStr

APRIL 13, 2025

This structure enables a seamless experience that starts when a company hires someone. One button click in Rippling sets up the new hire across HR, payroll, all relevant apps (Slack, Dropbox, GitHub, email, Salesforce), provisions their computer, and establishes them within the company’s financial systems.

Startup 157

Startup Sales Hiring Underperforming Technical Team Cloud 157

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. Don’t wait to launch your AI for a year.

AI 214

AI B2B ChatGPT Scale 214

Clouded Judgement

JUNE 27, 2025

Making strategic hires before the strategy is fully locked. This also has implications on the people you hire. You don’t want to hire the “old guard” who only knows how to run the “old guard” playbooks. That means doing things in parallel that used to be sequenced. The list goes on!

Cloud 157

Cloud Sales Hiring Scale Investment 157

Sales Hacker

OCTOBER 15, 2024

Cliff is a recipient of the 2024 Modern Sales Leader award from HubSpot and a 2024Top 50 CRO to Watch by Pavilion. Navigating the challenges of rapid growth, including hiring and managing cash flow. Navigating the challenges of rapid growth, including hiring and managing cash flow.

Acquisition 113

Acquisition Sales Hiring ChatGPT AI 113

SaaStr

MARCH 6, 2025

One of the classic original SaaStr posts was on the Top 10+ Questions to Ask a VP of Sales Candidate. It’s a different world today, AI-fueled, often distributed and hybrid, and with inflation both in titles (CRO or VP Sales) and compensation expectations. Use this updated script for hiring that first VP of Sales.

Sales Recruiting 184

Sales Recruiting Sales Hiring Scale Interviewing 184

SaaStr

FEBRUARY 25, 2025

SaaStr Annual attracts thousands of high-quality SaaS professionals across functions like engineering, product, marketing, sales, and customer success. Many companies strategically use the event to meet potential hires, conduct interviews, and build their talent pipeline.

Sales Recruiting 195

Sales Recruiting Scale CTO Hire Sales Hiring 195

ChurnZero

NOVEMBER 26, 2024

This is a guest article by Swati Garg , founder and CEO, Melo Associates , and Lindsay Lynch , senior recruitment consultant, Melo Associates , a recruitment firm focused on customer success hiring for SaaS and tech companies nationwide. Hiring the right talent for your company’s customer success team determines its success.

Technical Review 52

Technical Review Sales Recruiting Customer Success Sales Hiring 52

FastSpring

FEBRUARY 6, 2025

If you’re running a smaller digital business, you may find it challenging to hire great talent. If you’re facing challenges winning the best candidates for your roles, or if you have a small number of roles and every hire really matters, then don’t miss this episode of Growth Stage. X sales force, X meta.

SMB 107

SMB Sales Recruiting Branding Sales Hiring 107

Payrix

DECEMBER 18, 2024

While many partners excel technically, broader operational considerationssuch as resourcing and support considerations , sales strategies , marketing , and portfolio managementremain areas for growth. Are you planning to stand up a sales arm? You know, how do you stand up a support and operational function within your organization?

Payments 130

Payments Embedded Payments Merchant Services Payment Services 130

Sales Hacker

JUNE 17, 2025

At Procore, he led all customer-facing functions—Sales, Marketing, CS, RevOps, and BD. Hiring the right people, keeping them supported, and creating the infrastructure to help them thrive is critical. It’s the one person that can hire or fire you. TriNet exists to make that easier. It drives employee engagement.

AI 88

AI Technical Advisors Underperforming Technical Team Sales Hiring 88