2025 And The Rise of the Mech Account Executive

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

Have we lost interest in investing in the human side of sales?  

Not in hiring sales execs themselves, but in giving them more tools to be more “efficient”. It sort of seems like it.

AI has hardly rendered the sales professional obsolete.  Not yet, at least. Salesforce itself is hiring 2,000 sales execs this year to … sell its AI platform, AgentForce.

At most B2B companies, 35%-40%+ of the headcount is in sales and it’s often the largest functional area. And in any sales-led motion, you are going to just need more sales reps year after year to scale. Even now. Even in a more efficient world. Even with AI, as it is today.

And yet, there’s one thing that’s clearly changed the past 18 months. For the most part, folks seem done investing in more productivity for their sales humans. Unless it leverages AI.

2025 won’t be the death of the AE or even the SDR. But it may be all the investment goes into AI to supplement them, to turn them into “Mech AEs” — rather than adding tools to just make sales execs work better as humans.

We may be building Mech AEs.

Surrounded and powered by AI, making them much more powerful than before. 

See you soon at biggest SaaS event of the year — SaaStr Annual, May 13-15 2025!

Grab your tickets now before prices go up midnight tonight!!

• Save 20% on 1-2 tickets, $200 savings
• Save 30% on 3+ or more tickets, $350 savings
• on each ticket!

But should you miss these holiday savings: 

• Startup tickets will be $1099 at midnight
• Big Co & VC tickets will be $1299 at midnight

2025 should be a good year for almost all leading public SaaS companies:

1) Overall, any “downturn” ended in Q3’24, if there was one at all in their segment.

2) Most SaaS leaders are now in market with an AI offering, and even if early and minor, it’s leading to a boost — because there is incremental budget there. See Salesforce, Asana, etc. All getting a boost even though it’s early for AI.

3) Everyone got so efficient and at least non-GAAP profitable the past 2 years that they have room to hire and invest more. 

Some leaders with limited B2B2B exposure had a great 2024 (Samsara, Toast, Shopify, etc). Those with a lot of exposure often didn’t see a boost until the end of the 2024:

But 2025 should be better all across the board.

Not a magical time like 2021. But better.

The success rate for executive hires at high-growth SaaS companies can be surprisingly low – you’re often lucky if 50-60% of your management team works out long-term. In a recent conversation between HubSpot Chairman and co-founder Brian Halligan and SaaStr Founder and CEO Jason Lemkin, they shared their advice on what actually works when hiring VPs and building your SaaS executive team.

If you missed part 1 of this interview, you can catch up on their conversation about the current state of SaaS, evolving board meeting formats, and how AI is reshaping the industry.

One of the hottest topics in AI for B2B is around outcome-based pricing.

I worry it’s the cart driving the horse.

What do I mean? Simply that outcome based pricing may be exciting to VCs who think it unlocks more TAM and budget, and it may seem exciting to founders and execs who think it will help them grow deal size.

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

Read how Duro Labs increased integration adoption, reduced engineering time for integrations, and launched them 10x faster.

Many of the companies I’ve invested in only offer annual pricing. The common denominator is:

• they are products that require some real business process change to achieve the value from the product.
• and that sell mainly larger deals ($50k ACV and up).

If your product can be used successfully in 5 minutes, without any need for business process change, a freemium / free trial model works well. And here, forcing annual pricing just creates gates to getting paid. Your smaller customers may want to pay as they go with a cheap, simple product.

But in the case of true “enterprise” applications, where you are changing the way entire companies work, you usually have business process change to manage. Freemium doesn’t work well here.

Smartsheet for example standardized on annual pricing … plus a free trial. Why? Despite being somewhat competitive with vendors that offer monthly pricing (e.g., Asana and Monday), they learned their workflows were complicated enough they wanted customers to invest for a year to benefit from them.

My first meeting with a VC …

It went really well. In fact the very first VC I ever pitched as a founder offered to fund us tentatively with $5m — by the end of the first meeting!

Yes, it was a strong pitch with a strong albeit first-time team. But still, it seemed pretty easy, all things being considered. A $5m term sheet from my first VC pitch ever as a founder!

And … then I blew it.

What happened? Well, first the intro was from an ex-boss, so I had a strong warm referral. I also had a pretty good deck and presentation and team. Market timing was also on our side. We had 2 strong early reference customers. And … we were a pretty good duo pitching, my co-founder and me. Bear in mind, I’d done a lot of VC pitching as a VP at start-ups before. I knew what a good pitch was, and what good metrics were, and what VCs were interested in. I was new as a founder — but not new to fundraising.

We fairly quickly got a draft term sheet for $5m on something like a $10m pre. Not a very good today given the early traction we had, but fair enough for the time.

I went and asked some more seasoned folks what to do. I was advised by an angel investor to push back and ask for a significantly higher price. So … I did. Without even thinking about it. I asked for something like $7m-$8m at a significantly higher price. The details I sort of forget. But I know I asked for materially more.

The VC got offended / pissed / angry / spooked / worried / something. I don’t know what to this day. But he went dark.

© SaaStr 2025

644 Emerson St. Suite 200, Palo Alto, CA, 94301

If you'd like to stop receiving the SaaStr Daily, click here