Top SaaStr Content for the Week: Aileen Lee, Erika Schultz, HubSpot’s CoFounders and more!

Each week, we round up our most popular content so you can catch up on anything you may have missed. Check out this week’s top blog posts, podcasts, and videos:

Top Blog Posts This Week:

  1. The Early Hire That Almost Never Works: Director of Outbound.  A mistake I see way, way too often.  A new VP of Sales comes in that doesn’t know outbound.  And they hire a Director to get it going.  Why this almost always implodes in this post.
  2. 10 Tips to Start Selling to Big Companies as a Tiny Startup.  Why would a Huge Co take a risk on a tiny startup, without a brand?  They often won’t.  But sometimes, it’s worth it.  Here’s when, and how to get in the door.
  3. Seasoned VPs Cost 10x a Stretch VP Now. Is It Worth It?  It’s not just VP salaries that have gone up.  It’s the size of the teams they want on Day 1.  Does this still make sense in today’s tougher fundraising environment?
  4. 5 Interesting Learnings from HubSpot at $1.7 Billion in ARR.  HubSpot is the latest Cloud leader growing even faster as it approaches $2B in ARR than it did at $1B ARR.  Pretty amazing.  This post shows how they really do it.
  5. 5 Very Good Days, and 5 Pretty Bad Days, as a SaaS CEO.  It’s not just you.  Here were my Top 5 Days, and Top 5 Toughest Days, on the way to the first $10m ARR.

Top Podcasts This Week:

1. SaaStr 596: Scaling Revenue in 2022: What’s the Same and What’s Different? with Confluent President of Field Operations Erica Schultz

2. SaaStr 595: 5 Critical and Company-Altering Learnings from B2B Startups with Y Combinator MD of YC Continuity Anu Hariharan

3. SaaStr 597: VC State of the Market with SaaStr CEO Jason Lemkin and Cowboy Ventures Founder & Managing Partner Aileen Lee

4. SaaStr 594: Optimizing GTM for PLG with Stage 2 Capital Co-Founder and Managing Director Mark Roberge

5. SaaStr 593: State of the Cloud 2022: The Centaur Report with Bessemer Venture Partners Sameer Dholakia, Mary D’Onofrio, and Elliott Robinson

Top Videos This Week:

1. Everything that Breaks on the Way to $1B ARR with Mailchimp Co-Founder Ben Chestnut

2. Finding Opps in Every Challenge: From Humble Beginnings to 30 Million Users with Miro CEO Andrey Khusid and ICONIQ Growth GP Matthew Jacobson

3. Designing a Product Your Customer Can’t Live Without  with Brex Co-founder and Co-CEO, Henrique Dubugras, and Mutiny founder and CEO, Jaleh Rezaei

4.10 Lessons Learned Along the Path to $100M ARR with UserZoom CEO Alfonso de la Nuez and CMO Sophie Chesters

5. Why Y Combinator is Worth It – Clip with SaaStr CEO & Founder Jason Lemkin

Published on October 9, 2022

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