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

SaaStr

Former Head of Revenue at BILL and HubSpot Americas leader Michelle Benfer recently joined us on a SaaStr Workshop Wednesday share her insights on one of the most critical roles in any SaaS organization: the frontline sales manager. “At HubSpot, I had over 100 frontline sales managers reporting to me.

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A Lot of Great Sales Leaders — Just Aren’t Great at Selling Anymore. And Why You Really Need a VP of Sales, and Not a CRO.

SaaStr

I’m not talking about any close friends in sales here. But — there are a ton of folks I know that used to be great in sales. The other day someone who used to be an A+ sales leader emailed me about a position I’d introduced to him as a super hot start-up. And you just might want to hire him.

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5 Top Learnings from Legal SaaS Logikcull’s Almost $300,000,000 Sale to Private Equity

SaaStr

So the other day on Workshop Wednesday Andy Wilson, founder CEO of Logikull , and I did a deep dive on what it’s really like selling your company to Private Equity for almost $300,000,000! 3 Came from the Investment Bank They Hired. They lost their entire sales team, except one exec. In 2021, they moved to a PE mindset.

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I Hired My VP of Marketing at $20k MRR. It Wasn’t a Week Too Early.

SaaStr

One of the starkest differences I see between First Timers in SaaS and Second Timers is when they hire their VP of Marketing. They often hire a VP of Demand Gen Marketing even before they have their first paying customers. But it’s very, very easy to make the hire late. Second Timers know. But she can help. Don’t.

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You Won’t Know Most of Your 10x Hires Are That Good on Day 1

SaaStr

So Auren Hoffman did a SaaStr workshop a few years back that was one of my favorites, I’ve embedded it below. He made many great leadership points, but one in particular rattles around my head a lot and I think deserves its own post: You usually won’t know if you’ve made a 10x hire … when you make the hire. months later.

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Hiring and Building a High-Performing Sales Team with Lucas Price, Former SVP of Sales at Zipwhip ($700m Sale to Twilio)

SaaStr

At this week’s Workshop Wednesday, Lucas Price, former SVP of Sales at Zipwhip and founder and CEO at Yardstick, shares his insights on how to hire and build a high-performing sales team. During that time, he wasted a lot of money on failed sales hires and decided to learn everything about hiring sellers.

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4 Things Most Founders Get Wrong About Marketing with Dave Kellogg

SaaStr

And see everyone at 2025 SaaStr Annual, May 13-15 in SF Bay for 300+ more sessions, workshops, and braindates like this! “Marketing is fluffy and unmeasurable” – Unlike sales, which has clear metrics like quota attainment, founders often believe marketing can’t be measured.