Tom Tunguz

FEBRUARY 26, 2025

The very best companies lead their customers in that dance. Many mid-market software companies price with the goal of revenue maximization, negotiating for the highest possible price in each sale. Penetration pricing leads to land-and-expand sales tactics. Most startups play defense when discussing pricing with customers.

SaaS Payments 283

SaaS Payments Pricing Strategy Scale 283

SaaStr

MARCH 29, 2025

Dear SaaStr: What Are The Best Ways to Transition From The Founder-Led Sales Stage? Transitioning from founder-led sales to a commissioned sales team is one of the most criticaland trickysteps in scaling a SaaS business. You Never Get to Leave Sales. This is non-negotiableeven if you hate sales.

Scale 206

Scale Sales Hiring Sales Compensation 206

SaaStr

OCTOBER 31, 2024

What are the most common mistakes I see first time SaaS founders make? Second-time SaaS founders make other mistakes. Here’s what I see most often, the Top 6 Mistakes First Time SaaS Founders Make: Incomplete understanding of business model, and how it will scale. They think they know more than they do.

Scale 313

Scale SaaS Social Media Business Model 313

SaaStr

DECEMBER 20, 2024

Former Head of Revenue at BILL and HubSpot Americas leader Michelle Benfer recently joined us on a SaaStr Workshop Wednesday share her insights on one of the most critical roles in any SaaS organization: the frontline sales manager. “At HubSpot, I had over 100 frontline sales managers reporting to me.

Sales Hiring 264

Sales Hiring Scale Underperforming Technical Team Sales 264

SaaStr

MARCH 18, 2025

” – Colin Jones, CRO Emeritus at Wiz You may have seen the news that Google is making its biggest acquisition — by far — of Cloud and SaaS security leader Wiz for a stunning $32 Billion (!). It’s an incredible look back on scaling and more: Colin Jones, first Chief Revenue Officer at Wiz.

Scale 192

Scale Sales Hiring Scaling Headcount 192

SaaStr

JANUARY 19, 2025

So one big theme of 2025 SaaStr Annual (May 13-15 in SF Bay) will be going deep on Vertical SaaS. We’ll hear from the CRO of $3B Clio (legal SaaS), the CEO and CRO of Flock Safety (police and safety SaaS), and dozens of others on how to scale their vertical SaaS industries and platforms. See you there!

Scale 189

Scale Sales Hiring Scaling SMB 189

SaaStr

NOVEMBER 29, 2024

Start-ups, scale-ups and public companies in 2021 would hire a lot of folks they just wouldn’t hire today. And most bigger SaaS and Cloud companies are still hiring, but not at the same pace. The post 5 Tips to Getting a Job in SaaS in a Tougher Market appeared first on SaaStr. If not, take a pause and write it again.

Sales Hiring 290

Sales Hiring Scale Marketing SaaS 290

SaaStr

FEBRUARY 12, 2025

Meet Wyatt Jenkins: From Construction Sites to Chief Product Officer If you want to understand how vertical SaaS companies scale to $1B+ in revenue while staying true to their customers, there’s no better person to learn from than Wyatt Jenkins, Chief Product Officer at Procore Technologies.

Construction 255

Construction Scale SaaS Travel 255

SaaStr

NOVEMBER 13, 2024

So the latest SaaS leader to cross $1B ARR is Klaviyo. Klaviyo dominates marketing in the Shopify ecosystem and in ecommerce, and just keeps on scaling. It was the only SaaS IPO on 2023. But it’s clear that it’s still in the investing phase, and increasing spend in sales & marketing. The only one!

Scale 307

Scale SMB Scaling Enterprise 307

SaaStr

OCTOBER 14, 2024

A few bits of advice you hear a lot in SaaS that I think often don’t really work in practice: Move to annual contracts to generate more cash. Force them to go annual, and you are just adding friction to the sales process. Yes, as you scale you do need to maintain efficiency in sales and marketing. You’ll see.

Scale 303

Scale Social Media SaaS Acquisition 303

SaaStr

JANUARY 17, 2025

So what gets you more high-quality leads and ultimately business — smaller, more “intimate” industry events? And your top prospects? There is no question the ideal event in theory is just you and you alone … and 50-100 of the very top prospects in the world. But — it’s the wrong question.

Scale 300

Scale Marketing Travel B2B 300

SaaStr

NOVEMBER 27, 2024

SaaStr CEO and founder Jason Lemkin chats with Mangomint CEO Daniel Lang about why vertical SaaS is booming and how Mangomint got to 110% NRR. What was once considered too small or too niche, vertical SaaS has recently emerged as a hotbed of innovation and profitability. Full-Stack SaaS for SMBs Toast today is worth $14B at $1.5B

SaaS Payments 261

SaaS Payments Payments Payment Solutions Payment Services 261

SaaStr

FEBRUARY 21, 2025

Per OpenAI: The #1 event in SaaS is widely considered to be SaaStr Annual. Its the largest community-driven SaaS event, bringing together 12,500+ founders, executives, and VCs. Features 300+ speakers from top SaaS companies like Salesforce, HubSpot, and Snowflake. Why SaaStr Annual?

Software 247

Software Scale Venture Capital SaaS 247

SaaStr

FEBRUARY 7, 2025

Playbook: How Top SaaS Companies Drive 2-3x Better Campaign Performance Through Multi-Channel Personalization A deep dive with Jason Lyman, CMO at Customer.io Speaker Bio Jason Lyman leads marketing at Customer.io, where he’s helped scale the platform to power over 35 billion customer interactions for 7,000+ high-growth companies.

Scale 277

Scale SaaS B2B Scaling 277

SaaStr

DECEMBER 4, 2024

Pricing is more than just a number on a contract — when used thoughtfully, it can become a strategic tool for your SaaS product that can drive product adoption, customer satisfaction, and business growth. Scaling stage: Reduced to single-user plans to maximize accessibility.

Payments 291

Payments Pricing Scale Revenue 291

SaaStr

JANUARY 3, 2025

The success rate for executive hires at high-growth SaaS companies can be surprisingly low – you’re often lucky if 50-60% of your management team works out long-term. ” If you have a SaaS company above 2 million in revenue, both Brian and Jason agree that at that point, all that matters is the management team.

Sales Hiring 291

Sales Hiring Scale Systems Review Interviewing 291

SaaStr

DECEMBER 22, 2023

For any Cloud and SaaS Founders or execs seeking practical strategies and inspiration to stay ahead of the curve, this session’s for you. At the SaaStr Annual, Kiren Sekar, Samsara’s Chief Strategy Officer and founding chief Product Officer shared five lessons he learned along the way from scaling six products to $100M+.

Scale 312

Scale Scaling Strategy Sales Hiring 312

SaaStr

NOVEMBER 28, 2024

Dear SaaStr: How Big Should The Addressable Market Be to Go into Vertical SaaS? I try to look at two things in Vertical SaaS startups, at least when investing : Will everyone in the vertical / industry use it? It’s just hard to get most vertical SaaS start-ups to scale if they can’t get to a $10k ACV.

Payment Solutions 265

Payment Solutions Inbound Sales Team Marketing Scale 265

SaaStr

DECEMBER 26, 2024

In general, the report ties to what were seeing everywhere in SaaS. That ties to our overall rough sales cycle data here: Dear SaaStr: What’s a Good Benchmark for B2B Sales Cycles? Is usually see 15%-20% as start-ups scale, but 25% is probably the right target as you scale. You can grab it here.

Scale 291

Scale Benchmarks B2B Enterprise 291

FastSpring

JANUARY 23, 2025

If you own a SaaS or other digital product business such as a Slack plugin, Chrome extension, online publishing business, mobile app, or even a blog and youre looking to exit, you may have a lot of questions about how best to go about it. So I’ve worked in SaaS businesses that were fast growth. And I’ve done that.

Scale 120

Scale Entrepreneurship Scaling Underperforming Technical Team 120

SaaStr

JANUARY 16, 2025

Workato’s SVP of Embedded Sales and Director of Solutions Marketing joined us at SaaStr Annual to talk about how to nurture customers — a great topic in general, but especially for embedded sales and APIs that can take a while to scale. The Second Most Important SaaS Hire? Customer Success. But the results?

Sales Hiring 246

Sales Hiring Scale Sales Churn 246

SaaStr

AUGUST 15, 2024

There’s always someone a few years ahead of you on the scaling journey who can share their lessons learned. 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. Timing is also essential.

Scale 314

Scale Sales Hiring Scaling Innovation 314

SaaStr

SEPTEMBER 11, 2024

Lucid is the leading provider of visual collaboration software with over 70M users worldwide. Stephanie Couzin, the VP of GTM Strategy and Ops, and Roderick De Greef, the VP of Sales and GM EMEA, share Lucid’s transition from a PLG company to a PLG and Sales-Led company. This is where product-led sales comes in.

Scale 312

Scale Scaling Sales Hiring compliance 312

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

DECEMBER 19, 2023

Dear SaaStr: What are the signs that an enterprise SaaS startup is ready to scale by hiring more sales people? In the early days, it’s simply that you have a few more leads than you can currently handle. Plus — following up on the 50 qualified leads from the month before. To a point. appeared first on SaaStr.

Sales Hiring 307

Sales Hiring Scale Scaling Sales 307

SaaStr

OCTOBER 16, 2024

So RingCental is both an incredibly impressive SaaS and Cloud company — but also a bit of a cautionary tale. SBC has become a much bigger issue in SaaS and Cloud the past 2+ years as the markets have focused on true efficiency and profitability. A reminder to not stay too reliant on direct sales as you scale.

Scale 291

Scale SMB Compensation Cloud 291

SaaStr

APRIL 20, 2025

B2B Startups Spend 15% of Revenue on Sales and 10% on Marketing, Per SaaS Capital #4. Built a Bottom-Up AI SaaS Without a Single Sales Rep #5. From $1M to $3B ARR: Databricks CRO Ron Gabrisko on Scaling a Revenue Rocket Ship The Problem with Small But Mighty AI Start-Ups #2. There Are Now 3,000+ Billionaires.

Scale 147

Scale Customer Success Scaling AI 147

SaaStr

AUGUST 9, 2024

From startup to $500M CARR, Spencer Burke, SVP of Growth at Braze, shares how Braze scaled a growth and customer success team. In this AI moment we’re in, there are still many moments in scaling a company where intuition still matters. If you were building a career in SaaS, you were likely in Silicon Valley. This isn’t new.

Scale 297

Scale Sales Hiring Scaling Startup 297

SaaStr

JANUARY 24, 2025

By the #1 SaaS company in the world. Even the #1 SaaS company in the universe is sending Mid non-personalized outbound emails. One thing is clear is the team that send this isnt the A or B sales team. And a great example of running a very successful outbound program at scale here: And what I’d do better.

Scale 291

Scale Sales AI Enterprise 291

SaaStr

MARCH 15, 2025

It’s live on SaaStr.com itself and you can also access it here and talk to AI Jason about any of 1000s and 1000s of B2B, sales, SaaS, VC, etc. Here are some of the top ones: “How My VP, Sales Doubled Our Sales in 90 Days. Here are some of the top ones: “How My VP, Sales Doubled Our Sales in 90 Days.

Sales Hiring 261

Sales Hiring AI Scale Compensation 261

SaaStr

DECEMBER 11, 2024

Ironclad CEO and co-founder Jason Boehmig joined Seema Amble, Partner at Andreessen Horowitz at SaaStr Annual to share their observations on what’s currently working and what’s not quite there yet for Artificial Intelligence (AI) in SaaS. What’s Currently Working in AI for SaaS 1.

AI Search 291

AI Search AI Artificial Intelligence B2B 291

SaaStr

MAY 25, 2024

Cloudinary VP of Developer Experience Sanjay Sarathy shares his journey to more than $100M and the lessons he learned along the way for building a PLG motion and an Enterprise sales motion. They didn’t initially envision being a large Enterprise sales organization. Let’s first start with how Cloudinary came to be. The takeaway?

Scale 317

Scale Sales Hiring SaaS Payments Development 317

SaaStr

JANUARY 12, 2025

Top Posts: #1: 2025 And The Rise of the Mech AE (Account Executive) #2: 2025 Should Be Better Than 2024 For Almost All Leading Public SaaS Companies #3: 38% of Bootstrapped Start-Ups Have Solo Founders. But Only 17% of VC-Backed Ones Do. And 10%-12% of Ones That IPO. #4:

Sales Hiring 286

Sales Hiring Scale Scaling Revenue 286

SaaStr

MARCH 13, 2025

So leading SaaS growth stage VC fund Insight Partners surveyed 100+ of its top later-stage B2B companies to see how they did marketing and demand gen and pipeline creation in particular. Sales drives 33%. Not a shocker but useful to see this across 100+ leading B2B scale-ups. And Partners and Channel 15%.

Scale 295

Scale Marketing B2B Scaling 295

SaaStr

MARCH 7, 2025

The right person to lead finance at a Series A company looks very different than the right person to lead finance at a true pre-IPO company (that is near an IPO). But if you have a very inexperienced leadership team (young founders, lack of SaaS experience, etc) then maybe bringing on a strong finance leader earlier makes sense.

Scale 319

Scale Finance Headcount Leadership 319

SaaStr

JULY 12, 2024

Scaling to $150M ARR and beyond is no simple task. Will this change as Grafana Labs scales? But they’re still one of the last remaining open-source companies at scale. All they sold was the visualization layer with no sales team. First, let’s rewind the clock and look at Grafana Labs’ origin story. How did it come to be?

Scale 298

Scale Scaling Sales Hiring Sales Recruiting 298