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A Founder’s Guide to Building and Scaling Marketing Channels: Lessons from Datadog’s CMO and First Marketing Hire

SaaStr

Alex Rosenblatt was the first marketing hire and Chief Marketing Officer at Datadog, all the way through IPO and beyond. The 10th marketing hire is the most critical inflection point for team scaling – This is where informal processes break down and requires a complete rethinking of how the team operates. The problem?

Scale 242
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The 2026 Sales Team: 50% Humans, 50% AIs. All 1 Team.

SaaStr

So what does that mean for inside sales? A 50/50 Sales Team. At least for SMB and more routine mid-market sales. By 2026, these same AI systems will have evolved to manage entire sections of the sales process autonomously. An A+ AI will soon join every sales call, for real. You’ll Need to Manage Both.

Scale 247
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How Windsurf / Codeium Built a Billion-Dollar AI Company and a Winning Sales Machine

SaaStr

5 Key Learnings from Scaling from 3 to 75 Go-To-Market Team Members in Less Than 12 Months The latest SaaStr CRO Confidential is out and Sam Blond did a great deep dive with Graham Mareno, VP of Worldwide Sales at Codeium. Create Compelling Economic Incentives For sales talent, compensation is critical.

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How to Transition From Founder-Led Sales to Your First Sales Team: 9 Top Tips

SaaStr

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. Be specific.

Scale 199
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Fundraising In a Tighter VC Market, Advice for Hiring in 2024 and Much More with Jason Lemkin 

SaaStr

How Do You Sift Out the Bitter and Broken Individuals When Hiring? If it’s a role you’ve never hired, find someone great at it and have them do your final interview. For sales, product, or customer success, the best question you could ask is, “What would you do your first couple of weeks?” Don’t hire those people to lead.

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A 4 Point Test To Know If You Are Ready to Hire BigCo Folks

SaaStr

It’s easy to say “only hire people with start-up experience.” ” It’s also very tempting to hire folks that have worked at the partners, in the ecosystem that you work in, and at the companies you aspire to be like. When can you that risk on a Big Company hire? have documented systems and processes.

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The Enterprise Journey: 8 Keys to Going Upmarket Successfully with Workiva’s CEO Julie Iskow

SaaStr

You need: Sales leaders who understand complex, multi-stakeholder deals Customer success teams ready for high-touch support Legal expertise for enterprise contract negotiation Product leaders who can balance current needs with future vision Pro tip: Hire enterprise reps in pairs. If both succeed, you’re ready to scale.