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How to Train Your Sales Leaders: Key Learnings from HubSpot and BILL with Michelle Benfer

SaaStr

Having led sales teams of 500+ at BILL and 800+ at HubSpot, Michelle has unique insights into what makes great frontline managers and why investing in them is crucial for sustainable growth. “At HubSpot, I had over 100 frontline sales managers reporting to me. “That’s expensive, but optimal. ” The bottom line?

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ServiceTitan: Benchmarking the S1 Data

Clouded Judgement

The purpose of the detailed information is to help investors (both institutional and retail) make informed investment decisions. 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.

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Dear SaaStr: How Do You Let Customers Know You Are Raising Prices?

SaaStr

The key is to communicate clearly, justify the increase with added value, and give customers enough time to adjust. Communicate Through Multiple Channels Don’t rely on a single email to get the message across. The more personal and direct the communication, the better.

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Dear SaaStr: What Are Some Red Flags an Investor Might Not Be Serious?

SaaStr

First, if youre not sure they want to invest they probably dont want to. The One Question To Ask At The End of Every VC Pitch: What Are The Odds You Would Invest? Just ask what are the odds theyd want to invest, based on what they know now. And its 100% OK to ask. This can lead to hesitation or misaligned expectations.

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10 Simple Steps to Improve The Odds You Get VC Funded

SaaStr

Share everything anyone would want to know to invest in you. But unless you are raising from folks that truly invest pre-revenue, investors are going to want to see 3 strong months of growth in a row. If nothing else, point out an existing investment or two theyve made that is somewhat similar to yours. # Share it all.

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Dear SaaStr: I’m Joining a B2B Startup at $3m ARR as VP of Sales. What Should I Do First?

SaaStr

SDRs : Invest in 2–3 SDRs to generate pipeline for the AEs. Marketing : If marketing isn’t generating enough leads, you’ll need to invest here. Build a Predictable Lead Gen Engine You can’t scale without a steady flow of leads: Inbound Marketing: Invest in content, SEO, and paid ads to drive MQLs. Done right, this always works.

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Palantir’s +79% vs Bill’s -43%: The AI Divide That Defined SaaS Performance in 1H’25

SaaStr

Security and data infrastructure companies emerged as the biggest winners, while general productivity and communication tools lagged significantly. Bottom Lin e : Success in 2025 required either mission-critical positioning (security, data), clear AI differentiation (Palantir), or deep vertical specialization (Veeva, Guidewire). .

AI