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From Zero to Hero: How to Dominate Outbound SaaS Sales with Rippling and Founders Fund on CRO Confidential

SaaStr

In the latest episode of CRO Confidential, host Sam Blond, partner at Founders Fund and former CRO at Brex, sits down with Ashley Kelly, VP of Global Sales Development at Rippling. For context – Ashley had previously helped Sam scale Brex’s outbound sales from $2M to over $300M in ARR as Senior Director of SDR.

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Systematizing Go-To-Market Hiring

Tom Tunguz

It formed the basis for a career at HubSpot predicated on consistent quantitative analysis to scale the go-to-market, which he detailed in the Sales Acceleration Formula in 2015. I think it’s still one of the best books on how to repeatably scale sales teams. The cost of an incorrect hire is 6-12 months.

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The 5 Characteristics of a Great Sales Leader

SaaStr

Q: What makes a great sales leader? The best sales managers / directors / VPs: Recruit great team members. Sales requires a linear number of hires to grow bookings. So you have to be a great recruiter to scale. But the best sales leaders know where they are #1. Decrease sales cycles.

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Dear SaaStr: What Are The Biggest Problems You Face as a Startup Founder?

SaaStr

From $1m in ARR, and Then Forever After: Recruiting Great VPs. You need to learn to become great at recruiting. As you finally begin to scale, you’ll have enough revenue to hire some great folks, but not enough to build very redundant teams. More here: From Initial Traction to Initial Scale (~$10M in ARR): The Hardest Phase.

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Dear SaaStr: What Are The Biggest Pains as CEO?

SaaStr

The toughest part in the end is always recruiting. Recruiting. Over time, that’s recruiting more and more senior folks, so the target changes. As your company scales, you’ll start to hit 15%+ attrition in your employee base just naturally each year. You’ll have to be recruiting new ones all the time.

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Why Founder-Led Sales Breaks Earlier Than You Think

SaaStr

Founder-led sales generally stops scaling around $1m-$2m ARR. But you see growth start to decline in new bookings, that's a sign. A sign to hire a real sales leader. Over the years at SaaStr we’ve talked a lot about hiring a great VP of Sales, when it works, when it does, and how it moves the needle.

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Flat Metrics: The One Clear and Simple Sign its Time to “Top” a VP

SaaStr

Pretty incredible at scale. You’ll see: Bookings that stop increasing. For example, a great Stretch VP of Sales might get you to from $50k to $500k a month in new bookings. To recruit the team and resources it takes not just to meet the plan this quarter, but the next one and the following quarters as well.