16 Lessons For A First-Time B2B Marketing Leader
This guide is a crash course in what actually matters when you take on marketing leadership. It’s built from hard-earned lessons by Dave Gerhardt: former CMO and founder of Exit Five. If you're stepping into a Head of Marketing or VP role (or want to), this is the playbook you wish you had earlier.
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What’s inside the guide?
We went deep on leadership so you don’t have to learn the hard way.
This guide is built from Dave Gerhardt’s real experience as a first-time Head of Marketing and later CMO.
It’s packed with lessons on how to lead your team, work with your CEO, and actually move the business forward -- not just run campaigns.
You’ll get clear guidance on:
- How to think like a marketing leader — not just a great marketer
- What your CEO actually wants from you — and how to deliver it
- Why storytelling is more important than strategy docs
- How to align with sales — and stop playing defense
- What to prioritize when you're building (or fixing) your team
- Why momentum is everything — and how to create it yourself
Plus: Tactical advice you can apply right away, from budget planning to managing up, hiring smart, and making big decisions with imperfect data.
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FAQs
It’s for B2B marketers who are in (or heading into) leadership roles: like Head of Marketing, VP, or CMO. If you're moving from execution to strategy, this is for you.
You’ll learn the mindset, skills, and leadership habits required to succeed as a marketing leader—not just a great marketer. The guide covers:
- How to manage up to the CEO and executive team
- How to manage down and build a high-performing team
- How to manage around with finance, ops, product, and sales
- Real-world lessons about prioritization, hiring, internal comms, budget management, and more
It’s the stuff most people learn through years of trial and error, summarized for you in 30 minutes.
Yes. Every lesson comes from Dave Gerhardt’s real journey, from being the first marketing hire at Drift, to VP of Marketing, to CMO at Privy, and now founder of Exit Five. The mistakes, the wins, the lessons: it’s all in here.
Yes. 100% free. Just drop your email, and we’ll send you the full PDF right away.
It’s a beautifully designed, downloadable PDF, formatted like a playbook. Easy to read, easy to share, and packed with visual takeaways. You can read it in under an hour or skim and come back to it anytime you need guidance.
Join Exit Five today
- Access to Exit Five’s online community (more than 8,000 posts and 5,700 members)
- Access to the B2B marketer matching program (make 1:1 connections with peers)
- Access to monthly B2B marketing training sessions
- Access spaces for finding a job or looking to hire marketers
- Discount pricing on Exit Five courses and in-person events

