SaaStr

OCTOBER 25, 2024

Six months ago, security was the number one prohibition preventing businesses and software companies from buying AI. This can destabilize your business and have a big impact on cash. So the survey asked how much as a business has AI impacted its sales funnel. So how much business has it closed? It isn’t predictable.

Venture Capital 331

Venture Capital Marketing AI SaaS 331

SaaStr

JULY 9, 2024

So venture capital turns out to be a pretty tough business. Those rare investments that return enough money to the VC fund to pay off at least 1x the total fund size. And you can see VCs are often pretty careful to make sure structurally, any given investment can do it. Investing in the #3 or #4 in a space? A 1% stake?

Investment 302

Investment Venture Capital Social Media Startup 302

SaaStr

DECEMBER 25, 2023

G2 had us back for another great deep dive on just where SaaS investing is there days, and it was a great panel: Accel Partner Arun Mathew Inspired Capital Founder & Managing Partner Alexa von Tobel Salesforce Ventures Managing Partner Paul Drews and Jason Lemkin! Low investment multiples pose a key challenge.

B2B 282

B2B Investment Venture Capital Scale 282

Clouded Judgement

NOVEMBER 18, 2024

The document contains a plethora of information on the company including a general overview, up to date financials, risk factors to the business, cap table highlights and much more. The purpose of the detailed information is to help investors (both institutional and retail) make informed investment decisions.

Benchmarks 299

Benchmarks Payments Payment Services SaaS Payments 299

SaaStr

NOVEMBER 2, 2024

Having been through 4 acquisitions in different forms (founder, exec, etc), it’s a lot like a venture capital investment. A ton of time is invested negotiating price, and then way, way too much time on inconsequential legal terms, and then … it closes. Usually, there isn’t actually a ton of time to really get to know each other first.

Venture Capital 261

Venture Capital Acquisition Investment Pricing 261

SaaStr

MARCH 16, 2025

Instrument Everything Before running campaigns, ensure you have rock-solid data collection: Define clear metrics tied to business outcomes Create instrumentation that accurately tracks performance Focus on data that’s “directionally correct” – perfect precision isn’t required 4.

Scale 242

Scale Sales Hiring Scaling Marketing 242

USIO

FEBRUARY 7, 2025

APIs (Application Programming Interfaces) are at the heart of this transformation, enabling businesses to create customized payment workflows that meet the unique demands of their operations. API-driven payment systems reduce processing times by up to 40%, improving cash flow management for businesses of all sizes.

Payment Solutions 130

Payment Solutions Payment Services Payments Payment Methods 130

SaaStr

JUNE 2, 2023

Dear SaaStr: Does Bootstrapping Through an Agency/Services Business Work? Running two businesses at once well is really, really hard. I’ve invested in Logikcull and been an advisor to Showpad, both of which are successful and did just that. They slowly wind down the services business and stop investing (e.g.,

Business 301

Business Investment Software Scaling 301

Tom Tunguz

APRIL 21, 2024

Software companies don’t invest once in R&D & then sell copies of the software as we did in the 90s on CDs. 1 Despite the enthusiasm from Investopedia, I think it’s important to say that no financial metric is perfect & all of them are proxies for the ultimate performance of a business.

Software 296

Software Business Construction Government 296

SaaStr

NOVEMBER 20, 2024

A New GTM Mental Model for AI Products That feedback told GitHub that people who weren’t using the GitHub platform still wanted to use Copilot for Business. They ended up shipping Copilot for Business for non-GitHub Enterprise users, which was a commercial success. Another big investment during rapid growth is digital moments.

Scale 261

Scale AI Scaling Marketing 261

SaaStr

OCTOBER 31, 2024

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. Basically I only invest in first-timers. But they also make mistakes we tend not to make with experience. First-timers do just as well, if not better, than second-timers.

Scale 307

Scale SaaS Social Media Business Model 307

SaaStr

DECEMBER 16, 2024

Its a tough business, with sharp elbows, and half promises. I’ve later co-invested with VCs that treated me pretty poorly, at least IMHO. Move on and focus on your business. I know, but the thing is, someone else will still take their money. Also, no one really thinks VCs are saints. Everyone knows this. Three, let it go.

Investment 247

Investment Business 247

SaaStr

JANUARY 14, 2025

And how much that dramatically drives up the burn rate and cost of doing business. Their “sense” of what things cost is often just way too low once they start to invest the first round of VC capital they raise. Dramatically. This especially bites founders that get pretty far bootstrapping.

Startup 274

Startup Finance Engineering Investment 274

SaaStr

NOVEMBER 27, 2024

Consumers now also expect to talk to businesses through digital means. Onboarding, especially for vertical saas products and tools that oftentimes utilize hardware or require a vendor like a Mangomint to ingest 10+ years of existing data on the fly, is an order of magnitude harder since these businesses are open every day.

SaaS Payments 257

SaaS Payments Payments Payment Solutions Payment Services 257

SaaStr

NOVEMBER 19, 2024

Organizations that invest heavily in customer success earlier see much higher customer retention and loyalty than the competition. Your company is going to change business goals every year, and your customer success strategy has to move towards and align with those priorities. Pick Your Battles That Drive ROI What does that mean?

Customer Success 284

Customer Success Scaling Social Media Enterprise readiness 284

SaaStr

SEPTEMBER 8, 2024

Ryan’s previous company, ImportGenius , was the largest provider of business intelligence to the import-export industry, which gave them access to an extremely valuable list of customers, trade data, and understanding of the international trade market. Measure customer NPS early and make it a key KPI for the business.

Sales Recruiting 322

Sales Recruiting Scale Venture Capital Sales Hiring 322

Clouded Judgement

MARCH 28, 2025

Any disruption of service at this facility could harm our business… We currently intend to add a second data center facility in 2008, the primary purpose of which is to add capacity. The incentives to start a competing business to an on prem software company that hit $25m in revenue were low. Someone can always catch you.

Cloud 299

Cloud AI Scale Scaling 299

SaaStr

MAY 10, 2025

High net retention (120%+ for bigger customers) is a sign of a healthy, scalable business. Invest in Relationships Customer success isnt just about metricsits about people. Dont wait until youre at $5M or later to invest in customer success. It combines renewals, churn, and upsells. Be careful here. Start Early.

Sales Hiring 214

Sales Hiring Customer Success Scale Retention 214

SaaStr

NOVEMBER 28, 2024

I try to look at two things in Vertical SaaS startups, at least when investing : Will everyone in the vertical / industry use it? Even a fairly small business can pay $10,000-$20,000 a year for one app, usually. and Is the app so core, or at least is on a path to become so core, that they can charge $20,000+ a year for it?

Payment Solutions 261

Payment Solutions Inbound Sales Team Marketing Scale 261

SaaStr

DECEMBER 12, 2024

So theres a theme Ive been working on with all the SMB-focused founders I work with and have invested in: # 1. You can still make them super happy, but a subset of small businesses will churn at that rate anyway. # The Goal for SMB SaaS is 100%+ NRR. Easy in enterprise, hard in true SMB. # Thats often 3% a month or so.

Churn 273

Churn SMB Payments Payment Solutions 273

SaaStr

APRIL 5, 2025

SEO: How Rupa Health Dominated Search with Programmatic SEO and AI Rupa Health invested heavily in search, aiming to own the top spots for specific lab tests and biomarkers. Invest in scraping and cleaning tools, and make sure your emails are personalized to grab attention. Pro Tip: Outbound sales rely on data quality.

Scale 229

Scale AI Search Sales Hiring Acquisition 229

SaaStr

OCTOBER 23, 2024

In 2006, BILL CEO and Founder René Lacerte set out to define a category around financial operations for small and midsize businesses (SMBs). ’ Bill is approaching half a million customers, so has a good pulse on small businesses. With SMBs, the smallest business is owner-operated. Needless to say, he succeeded. in revenue.

SMB 307

SMB Payment Services Payments Payment Methods 307

Buffer Resources

OCTOBER 10, 2024

Turns out, I’m not alone: A study by HubSpot found 31 percent of participants saying that an About Us page is one of the most important elements of a business website. It’s not what will initially provide you with the most return on investment (ROI) , either. How do you operate in your day-to-day business?

Social Media 120

Social Media Merchant Services Business Branding 120

SaaStr

DECEMBER 27, 2024

Engineering resources: With thousands of engineers, companies like HubSpot can make substantial AI investments when they choose to 3. The Future of AI in Customer Support While many vendors are achieving similar baseline results with AI customer support, Brian believes we’re still early in unlocking its full potential.

AI 284

AI Marketing SaaS Interviewing 284

SaaStr

MARCH 18, 2025

A Philadelphia native, Colin started his professional career as a Business Development Representative (BDR) 14 years ago and worked his way up to his current role as CRO. This approach required immense trust from the CEO to invest millions ahead of proven results.

Scale 185

Scale Sales Hiring Scaling Headcount 185

SaaStr

APRIL 15, 2025

About Ethan Kurzweil Ethan is the founder of Chemistry VC, a focused early-stage venture firm that writes $3-30M checks with an average of $10-12M for Series A investments. Prior to founding Chemistry, Ethan spent 16 years at Bessemer Venture Partners, where he led investments in successful companies like PagerDuty, Intercom, and SendGrid.

Technical Review 157

Technical Review Venture Capital Outsourced Development ChatGPT 157

SaaStr

MARCH 17, 2025

Im investing in fact at SaaStr Fund in a solo founder right now. 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. If youre business-focused, hire a strong technical lead. Dear SaaStr: I Have No Co-Founder. What Should I Do?

Sales Hiring 247

Sales Hiring Scale Scaling Engineering 247

SaaStr

JANUARY 23, 2025

Moving upmarket isn’t just a nice-to-have for most SaaS companies – it’s often the difference between building a sustainable $100M+ ARR business and getting stuck in the mid-market quicksand. But the rewards – higher retention, bigger deals, and ultimately a much larger TAM – make it worth the investment.

Enterprise 244

Enterprise Sales Hiring Scale Outsourced Development 244

SaaStr

APRIL 28, 2025

CAC Payback Period Predicts Success More Accurately Than Any Other Metric CAC payback period stands above all other SaaS metrics as the most holistic indicator of business health. The Five Lessons 1. When customers desperately need your solution, your CAC decreases because they seek you out and move quickly through your funnel.

Scale 260

Scale Transportation Scaling SMB 260

SaaStr

FEBRUARY 7, 2025

They: Started with clear use cases Built a strong data foundation Focused on measurable customer value Invested consistently over time Maintained a human-centric approach For SaaS companies looking to leverage AI, the key is to start building your data advantage now, even if you’re using third-party tools.

AI 262

AI Scale Government compliance 262