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This edition of the SaaStr Daily is sponsored in part by Stripe

AI Should Kill “Contact Me” in 2025. It’s Long Since Time.

By Jason Lemkin
Monday, January 13, 2025 | Early, Sales

AI Should Kill “Contact Me” in 2025. It’s Long Since Time.

Perhaps the single worst experience in B2B sales is “Contact Me”.

I don’t just mean the lack of transparent pricing inherent to that flow. I don’t even mean the need to get on the phone instead of communicating otherwise. Having a separate flow for large enterprise deals makes complete sense.

What I mean is the process is terrible, and worse than ever.

A prospect shouldn’t have to wait — often days— to talk to sales to buy your product.

MORE HERE

LIVE this Wednesday: What to Really Expect From Your CRO / VP Sales In The First 90 Days

By Amelia Ibarra
Monday, Jan 14, 2025 | Workshop Wednesday

Up Next: Wednesday, January 15th @ 10AM

Topic: What to Really Expect From Your CRO / VP Sales In The First 90 Days

Speaker: Kathy Lord, CRO, Zensai

Workshop Wednesdays is our weekly series where we’ll be bringing some of the best SaaStr speakers to you LIVE, every Wednesday.

Each workshop will be hosted in a live, interactive 30-minute format at 10am Pacific each and every Wednesday. This workshop will be 100% LIVE, not pre-recorded, and will be hosted in an, interactive 30-minute format, including Q&A.

SIGN UP FOR WORKSHOP WEDNESDAY

8 Quick Ways to Get More High Quality Leads. Right Now.

By Jason Lemkin
Sunday, January 12, 2025 | Early, Q&A

There are many “lists” you can buy out there, and most will perform relatively poorly. You can have an AI SDR assemble its own list of prospects to auto email. That rarely works all that well, either. After all, no one on those lists opted in to hear about your product. Still, they can be worth doing if your value prop is so unique and strong it can clearly be defined in one great subject line, and a short, tight email.

What you really want if your deal size isn’t tiny are at least somewhat qualified leads for your team to follow-up with. A handful of real, qualified leads you can add to the team’s pipeline — next month.

Some ideas:

Do paid marketing where your competition also does it. Don’t flee the spaces where your competitors are strong. At least a handful will be looking for a newer, more innovative vendor.
Follow up with all your champions that have moved on to other companies. Do you know where your champions have moved on to? They’ll often bring you into their next company and role. But it can help a lot to get the ball rolling. Find out where they went — and reach out.
Invite your existing customers to regular webinars together with your prospects. Do this, and your customers will sell your product to them for you.
Do events — the top ones where your customers and prospects are. If you can one way or another capture leads. Booths can work well, if you have budget. Why? Because the best events attract the best customers and prospects in their industry. The advantage here is customer concentration combined with intent. Yes, booths and workshops can be expensive. Don’t spend what you can’t afford. But if the event is the #1 or #2 in your space, they will also attract a significant number of potential customers.

HIGH QUALITY LEADS

LinkedIn: The Greatest B2B Acquisition of All Time?

By Jason Lemkin
Monday, January 13, 2025 | Blog Posts

LinkedIn: The Greatest B2B Acquisition of All Time?

So when Microsoft paid $26 Billion to buy LinkedIn, it seemed like they were getting a pretty good deal.

Fast forward to today, it looks like a great one. LinkedIn is at $17 Billion in ARR, still growing 10%, and its whole division is wildly profitable — with 50%+ operating margins!

There may be better M&A deals in the history of B2B. But there can’t be too many better ones.

THE GREATEST B2B ACQUISITION

Dear SaaStr: How Long Should a CEO Continue Being the Head of Product?

By Jason Lemkin
Sunday, January 12, 2025 | Growth, Hiring

Roughly — only for as long as it’s about a 10-hour a week job.

Or often, maybe only up to $3m-$5m in ARR or so. These days, especially, I see way too many SaaS companies at $8m-$10m ARR or beyond without a true VP of Product.

Too many CEOs especially keep winging it for far too long.

Three mistakes I see so many SaaS founders make:

First, they wait too long to hire a full-time “head of product” even after the product gets complex. Once your product has 50–100 workflows, dozens of use cases, 100s or 1000s of customers, etc. … even just 15-20+ really big customers, all using your product differently … it’s just too much to hack and juggle informally. My rough rule of thumb is somewhere between $3m and $5m in ARR in SaaS most products just get too complicated to hack product anymore. You’ll ship better-prioritized features, with happier customers, with better trade-offs, with a full-time head of product. CEOs that hang on too long here start shipping features and products that are no longer force-ranked the way they should be. And the key is to hire a true head of product. Someone that can own it, and in the past, has owned a product. If you hire someone too junior, you get a project manager but not enough of an owner here.
And second, later, CEOs wait too long to give up on being the product visionary. Hopefully, the CEO is always the strategic visionary, forever. But at some point, the product itself gets so deep and rich, and the markets evolve so much, and the customer needs are so varied and nuanced once you dig in deep … that the founders’ original product vision becomes too simplistic, too dated and stale. Every 5–6 years or so, in most cases, everything in the market has changed, and the product has evolved so far that the Day 0 vision is very dated. At this stage, founders need to let go and have the team own the product vision — not them. The founders still are the heart of the corporate strategy. But the team is now spending 1000x more time with customers, with feature enhancements, with nuances on product lines with 1000s of features … you have to let the team define 95% of The Future. And your job becomes more to set the direction, but not provide the directions.
And finally, too many CEOs just hire too junior of a product person. That never works. You need someone seasoned enough to own the product and the product roadmap. Someone that has truly put features into production and managed some sort of team. Not someone just to make charts and hope someone in engineering might listen to them.

So bring in more help, and let it go a bit earlier than planned. It’s your idea, and your vision, but both of those need to evolve in the coming years.

HEAD OF PRODUCT

This edition of the SaaStr Daily is sponsored in part by Stripe

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STRIPE SESSIONS

Microsoft Pays Its AI Engineers 48% More. What About You?

By Jason Lemkin
Saturday, January 11, 2025 | Blog Posts

Microsoft Pays Its AI Engineers 48% More. What About You?

So a newer issue that is discussed a lot at start-up board meetings and investor meetings is AI Engineer comp.

In general, I find most start-ups want to keep engineering comp fairly flat. Back in the day, my CTO just wanted 3 tiers: entry level, top IC, manager. That was it. 3 pay bands, and they were very tight. Equity varied a lot more, but I know it was important to my CTO that everyone on his team felt like equal stakeholders, relative to experience.

I do think this is true at most start-ups, today too.

They want fairly consistent comp across engineering, and fear if nothing else, lots of issue if favorites are played, the new “guy” gets a better deal, etc.

But AI is challenging this.

ENGINEERS PAID 48% MORE

Dear SaaStr: How Bad Does it Look to Be on The Product Team at a Failed Startup?

By Jason Lemkin
Monday, January 13, 2025 | Early, Product

If the company actually shipped a strong product people respect — not bad at all.

If the company shipped something cr*ppy, a POS hack that looks like it — it’s a negative, at least to folks that have really shipped products to production.

Don’t worry too much. There aren’t enough great seasoned product folks out there. There just aren’t enough. So we have to hire every great product manager we can get. And it’s often not their fault they didn’t pick the next Slack.

We don’t blame you if the start-up failed. We don’t even care — so long as you’ve proven you can ship A+ level software. Ideally, that at least some customers have purchased.

When I meet someone like this, I ask for a demo. If the product rocked, I don’t really care exactly how far the company itself got. Further is better, of course. But unless it’s for a VP of Product position, I’m OK if you didn’t get enough paid customers to hit escape velocity.

HOW BAD?

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AI Should Kill 'Contact Me' in 2025