From Left To Right: Michael Bloch (Partner, Quiet Capital), Garrett Marker (CRO, Brex), Jennifer Burke (CRO, Faire), & Tomer Chernia (VP GTM, Cursor)
Last week, vibescaling and Quiet Capital co-hosted a private GTM leadership panel in SF (at one of my favorite spots now, The Progress).
The theme was "GTM Leadership in the Age of AI” - see below for a short snippet:
Big thank you to Michael Bloch (Partner @ Quiet Capital) for moderating the panel, as well as Garrett Marker (CRO @ Brex), Jennifer Burke (CRO @ Faire), & Tomer Chernia (VP of GTM @ Cursor) for giving us a ton of great insights on how the role of a sales leader is changing and what they’re seeing on the front lines.
It was an awesome turnout, ~30 of some of the best AI-natives GTM leadership talent in SF.
We’re expanding to GTM executive search as a firm at vibescaling, ran by Cailen, so this was a good kickoff event for that stream. Many more of these to come, as we solely focus on GTM recruiting, media, and investing moving forward for seed through series C AI-natives in SF/NYC.
Here are my 4 takeaways from the event:
Table of Contents
#1 - The Org Chart Is Being Redrawn: One Operator, Many Agents
The most consistent theme across the panel and the post-event conversations: companies at scale are fundamentally rethinking how they staff GTM.
It's not just "we're hiring fewer people." It's a structural shift in what a role even is.
The roles that used to be GTM Finance Analyst, RevOps, BDR, and Post-Sale CSM are getting consolidated into a single employee operating multiple agents across the workflow.
Same job-to-be-done, but the operator is orchestrating agents instead of stitching together Slack DMs across five teammates.
This shows up most obviously in deal motions. The days of rolling into an in-person meeting over-gunned with an AE + SE + CSM are showing signs of aging.
A single technical seller, with the right tooling and agent stack behind them, can now do the job of three.
Two implications I'm sitting with:
The IC seller who is also operator-minded is the most valuable profile in GTM right now. If you're an AE who can also build a Clay workflow, run a Dust/Claude Cowork orchestration, and self-serve on RevOps stuff, you're worth multiples of the AE who can only sell.
Hiring is shifting from "more headcount" to "more leverage per headcount." This is going to compress the GTM org chart in a way we haven't seen in SaaS.
#2 - The SaaS Stack Is Collapsing & Budgets Are Under The Microscope
The natural follow-on from #1: if one person can do the job of three, what tools are they actually using?
The answer that kept coming up: fewer, and increasingly through MCP and headless experiences instead of standalone UIs.
What I heard from the room in the post-panel convos:
Teams are being told to build the agent before asking for headcount or new SaaS budget. The default is no longer "let's evaluate a vendor," it's "can we put this together ourselves in Cowork/Dust/Clay?"
A lot of products that felt essential 12 months ago are being deemed irrelevant. Either the workflow is now headless (the LLM is the interface), or the underlying job-to-be-done has been absorbed by a more horizontal tool.
The renewal conversation has changed. CROs and CFOs are walking into renewals with a much sharper "do we actually still need this?" energy.
This is a really big deal for the SaaS vendor world, and I don't think a lot of category leaders have fully priced it in yet.
For sellers, it also means your discovery has to be sharper than ever. An "we'd love to do an evaluation" inbound is not the buying signal it used to be.
The real signal is when someone has already tried to hack it together themselves and hit a wall.
#3 - Anyone Entering Data Into A CRM Will Feel Barbaric In 6 Months
One skill that's going to absolutely go away in 6 months, it's going to feel barbaric, is anybody entering anything into a CRM.
The pattern I'm seeing (and that panelists + folks I talked to confirmed): Wispr Flow into Claude Cowork (or another orchestration layer), then out to CRM, calendar, email, Slack, the whole stack.
You talk into the prompt window. Cowork updates the opp, drafts the follow-up, schedules the next step, pushes notes to/from Granola, and so on.
The before/after:
Before: Rep finishes a call, opens Salesforce, types for 15 minutes, half-asses it because they're late for the next call, manager nags them about it in 1:1
After: Rep talks for 60 seconds, every system is updated, follow-up is drafted, manager has accurate pipeline data
Two things are converging here:
Voice-first interfaces are finally good enough that you genuinely don't need to type (see Granola, Wispr Flow eating the productivity stack)
Tool orchestration via MCP means a single voice command can hit every system you care about, not just one
I'd bet money that "manual CRM hygiene" disappears as a meaningful part of the AE job by EOY 2026.
The reps who get fluent with this stack now will look like these new-age reps in 6 months.
#4 - Forecasting Is Going Quarterly, Not Annual
This one was the most surprising to me, and it came up more in the post-panel conversations than on stage.
At a lot of the fastest-growing AI-natives, including some of the top 50 AI-natives, annual planning/annual numbers are dead.
The reasoning: the markets are moving too fast to commit to a 12-month plan that anchors comp, quotas, and forecasts.
What's happening instead:
Quotas and forecasts are being reset quarterly (and sometimes faster)
Sales is blowing past their numbers at a rate that makes the comp math look broken to finance, "we're overpaying salespeople" is a phrase I heard more than once
Finance and sales are in a near-constant calibration loop, adjusting comp, accelerators, and territory in much shorter cycles
This is obviously a good problem to have. But it has some implications:
If you're a candidate evaluating a role, the OTE number a company quotes you is way less meaningful than it used to be. Ask how they handle quota resets, what happened to comp when reps blew past plan last quarter, and whether accelerators get capped.
If you're a sales leader, the org you're running today is going to look meaningfully different in 6 months.
TL;DR: annual cycles are a SaaS-era artifact. AI-native GTM runs on shorter loops.
The through-line across all 4: the shape of a GTM org is being rewritten in real time, and the operators who lean into it are the ones compounding the fastest.
Stay tuned for the next one! Excited to keep throwing these monthly.
If you want on the list for the next one in NYC or SF, DM me.
And if you're a BDR, AE, or sales leader curious about what's out there in AI-native GTM right now, DM me on that too 🙂.
Thanks for tuning in!
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For those who are new, my name is Chris Balestras, partner @ Vibescaling - a GTM advisory, recruiting, media, and investing firm, working with seed through series C AI-natives to help them grow.
Where to find Vibescaling:
We work with many of the hottest AI-native startups in various capacities, and for those who are interested, shoot me an email at [email protected] or a DM on LI.
🫡 cheers,
Chris