Small Deals at Large Customers. Hooray!! And 100% At Risk. (Updated)

by Jason Lemkin | Feb 23, 2024 | Blog Posts, Customer Success, Customer Success, Growth | 2 comments

So there’s kind of a mean exercise I do at board meetings. It doesn’t sound mean, I do it very kindly.  But I’ll be honest, it’s a bit of a trick question. A VP of Sales will do a deal review and talk about how they closed a new epic logo for a small initial deal that...

Doubling Down: Harpinder Singh, Partner at Innovation Endeavors

by Jason Lemkin | Feb 22, 2024 | Blog Posts, Doubling Down, Growth | 0 comments

“Doubling Down” is a new series where we hear from top B2B SaaS investors on their most recent activities and takes on the current market. We had a great one last time with Hilarie Koplow-McAdams, Venture Partner at NEA. Check that out here. This week...

You Don’t Do Nearly Enough to Help With Customer Migration. But It’s Magic If You Do.

by Jason Lemkin | Feb 22, 2024 | Blog Posts, Customer Success, Early, Growth, Sales | 0 comments

When you ask customers to switch from an existing vendor to you … Do you offer to do ALL the work? The migration?The implementation?The integrations?The data mapping? If not, imagine all the friction you could remove if you did — Jason ✨Be Kind✨ Lemkin  🇮🇱...

A Soft Miss vs. A Hard Miss in Sales (Updated)

by Jason Lemkin | Feb 18, 2024 | Blog Posts, Growth, Sales, Sales | 0 comments

I've never seen a great VP of Sales hide from a miss — Jason ✨Be Kind✨ Lemkin  🇮🇱 (@jasonlk) August 26, 2023 We’re coming up on the quarter.  We always are, really. Some of you are going to beat the plan! Most of you maybe, even. I hope. But not all....

The #1 Hack To Making Sure a VP of Sales or Top AE Will Work Out

by Jason Lemkin | Feb 17, 2024 | Blog Posts, Growth, Leadership, Sales, Sales | 0 comments

We’ve talked a ton on SaaStr over the years on how to make sure your VP of Sales and top hires really work out.  That they are the right ones. We can pretty much summarize a lot of it into the following: Your VP of Sales should have lots of experience selling at...

The Thing Is, Maybe 10%-15% of Venture-Backed Startups Are Still Running the 2021 Playbook. In 2024.

by Jason Lemkin | Feb 16, 2024 | Blog Posts, Growth | 0 comments

Reading social media, tech press, and blog posts you’d think everything was about efficiency.  Heck, the 5 Interesting Learning series on SaaStr is all about efficiency. And for many in SaaS, especially those that sell mainly to startups and tech, it’s...

Entrepreneurship … It Changes You

by Jason Lemkin | Feb 16, 2024 | Blog Posts, Growth, Leadership | 0 comments

Dear SaaStr: Could you talk about your experience with the downside of entrepreneurship or startups? The “downside” of entrepreneurship is that it changes you. Not immediately, but sometime around 24 months in: You will think about your start-up close to...

Doubling Down: Hilarie Koplow-McAdams, Venture Partner at NEA

by Jason Lemkin | Feb 15, 2024 | Blog Posts, Doubling Down, Growth | 0 comments

“Doubling Down” is a new series where we hear from top B2B SaaS investors on their most recent activities and takes on the current market. We had a great one last time with Satya Patel, Partner at Homebrew. Check that out here. This week we’re...

2024 Is The Year to Think About Buying Someone. Or Merging. At Least Think About It.

by Jason Lemkin | Feb 13, 2024 | Blog Posts, Growth | 0 comments

2024 is the year every founder think about an acquisition That doesn’t mean do one, but it does mean think about doing 1 that could move the needle. Valuations are somewhat down, but more importantly, folks are more rational than they have been in years. In 2021, no...

11 Things That Set The Best Sales Teams Apart From The Rest

by Jason Lemkin | Feb 12, 2024 | Blog Posts, Growth, Sales | 0 comments

A great sales team can get a prospect to: – Buy now vs. later (a big deal) – Buy from you vs. a competitor more often (huge) – Buy product that sort of meets their needs (good-ish) – Buy product they won’t actually use (not as good) A mediocre...

My App Stack: Rachel Wolan, CPO at Webflow

by Jason Lemkin | Feb 10, 2024 | Blog Posts, Growth, My App Stack | 0 comments

“My App Stack” is a new series where we dig in with top CMOs, CROs, CTOs and CEOs on just what apps they’re really using to run their business.  I always learn a lot from these — they are in essence a best practices list from each leader.  Last time we had a great one...

How to Sell a Second Product

by Jason Lemkin | Feb 6, 2024 | Blog Posts, Growth, Product | 0 comments

Biggest challenge with rolling out a second product: Sales will sell whatever is easiest to sell A second product needs a second sales team maybe even from Day 01 — Jason ✨Be Kind✨ Lemkin  🇮🇱 (@jasonlk) January 30, 2024 So we’ve had a ton of great...

Sapphire Ventures: GenAI Funding is Up 271%. Everything Else? Down -36%

by Jason Lemkin | Feb 5, 2024 | Blog Posts, Growth | 0 comments

Pretty good: "OpenAI on track to hit $2bn revenue milestone as growth rockets" https://t.co/H8xJmVWcNc via @ft — Jason ✨Be Kind✨ Lemkin  🇮🇱 (@jasonlk) February 9, 2024 So most of you can probably infer from funding posts and press releases just how...

Dear SaaStr: How Do You Keep Yourself From Getting Fired as a Founder CEO?

by Jason Lemkin | Feb 2, 2024 | Blog Posts, Career Growth & Advice, Growth, Leadership, Q&A | 0 comments

Dear SaaStr: How Do You Keep Yourself From Getting Fired as a Founder CEO? First, note it isn’t easy to get fired as a founder CEO.  Especially if you haven’t raised all that much money.  I’ll leave the legal and contractual answers to others. But...

Dear SaaStr: What Is The Ideal Size For a SaaS Marketing Team?

by Jason Lemkin | Feb 1, 2024 | Blog Posts, Growth, Hiring, Marketing, Marketing, Q&A | 0 comments

Dear SaaStr: What Is The Ideal Size For a SaaS Marketing Team? The ideal size of a SaaS marketing team until you are at $10m+ ARR is the size that is accretive. The last thing you want is a bunch of “marketers” whose ROI you don’t understand.  That’s where...