Growth After Headcount

CRO 2.0: $25M To $100M From The Terminal — Omar Ismail (Ascend) #003

Haris Odobasic — Thu, 30 Jul 2026 07:32:36 GMT

Ascend grew from zero to $25M ARR with no growth team. No growth marketer, no ads manager, no paid engine. Word of mouth, referrals, and a small set of partnerships. Then Omar Ismail joined as COO and built the entire go-to-market stack himself, orchestrated end to end in Claude Code. The target now: $100M ARR without meaningfully scaling headcount.

Omar calls the second half of his job CRO 2.0: one person owning strategy and the machine that executes it. He argues the real trust problem with AI is not hallucination but software bugs in the systems it builds, which is why his next hire is a go-to-market engineer, not a marketer. And when everyone has the same tools, differentiation moves back to taste, judgment, and the things AI can't do at scale: physical mail, conferences, human relationships.

Chapters

00:00 — Intro

00:35 — Banking, VC, and a music-tech exit before Ascend

03:08 — Zero to $25M ARR on word of mouth, now going AI native

03:46 — No growth team: one COO owns the whole go-to-market

07:18 — Claude Code as the orchestration layer

08:48 — The trust problem is bugs, not hallucinations

10:24 — The next hire: a go-to-market engineer

11:22 — HubSpot backbone, natural-language dashboards on top

13:15 — Where humans stay: taste, judgment, 14 usable hooks out of 20

15:24 — When everyone runs AI outbound, mailers and conferences win

19:08 — $25M to $100M without adding people

20:44 — The KPI that never changes: retention

Guest

Omar Ismail, COO at Ascend.

LinkedIn: https://www.linkedin.com/in/omarismailb/

Ascend: https://www.joinascend.com/

https://omarismail.com/projects/growth-engine

About the show

Growth After Headcount is a podcast and a book about how companies scale with AI

instead of people. New episodes weekly. The book lands in 2027.

More at https://www.growthafterheadcount.com/

About the host

Haris Odobasic is Managing Partner at Revenue Wizards (https://revenuewizards.com/),

a GTM and RevOps consultancy, and the author of The RevOps Pendulum

(https://geni.us/revops-pendulum). He writes and speaks about how AI is changing the

way companies are built and scaled.

LinkedIn: https://www.linkedin.com/in/harisodobasic/

X: https://x.com/OdobasicHaris

100x The Human, Skip The Headcount — Amos Bar-Joseph (Swan AI) #002

Haris Odobasic — Sun, 26 Jul 2026 09:37:04 GMT

Amos Bar-Joseph built and scaled two B2B startups on the old playbook. Raise big, hire to forty people before the first million in revenue, then spend years fighting the bloat you created. With Swan AI he threw it out. In 2025 Swan went from zero to over 200 customers and seven figures in ARR with three founders and no additional hires.

The number he's aiming at is ten million dollars in ARR per employee.

This episode is about how that actually works. Amos started where most teams start, building a specialized agent for every task, and it didn't hold. Swan now runs its entire go-to-market on a single coding agent with a file system and a knowledge base it updates itself. We get into why data is not context, why the job that's left for humans is specification and review, and why he'll never let AI write his LinkedIn posts.

Chapters

00:00 — Intro

00:21 — Two startups on the old playbook, and why it broke

01:10 — The autonomous business: scaling ARR per employee, not valuation

01:39 — Zero to 200 customers with three founders

02:54 — Why Swan killed its specialized agents and runs one

04:54 — Data is not context: what your CRM teaches an agent

06:40 — Context engineering, and why it's the core RevOps skill now

10:29 — Fully automated, semi-automated, human-first

12:19 — Different beats better: don't give AI your edge

14:17 — Personal brand, and the rise of the analog

18:14 — Scaling one seller to 100x instead of hiring ten

20:41 — What this means for VC and bootstrapping

23:03 — Talent, compensation, and widening inequality

25:09 — A software revolution, not a labour revolution

Guest

Amos Bar-Joseph, co-founder of Swan AI.
LinkedIn: https://www.linkedin.com/in/amos-bar-joseph/
Swan: https://www.getswan.com/

About the show

Growth After Headcount is a podcast and a book about how companies scale with AI instead of people. New episodes weekly. The book lands in 2027.

More at https://www.growthafterheadcount.com/

About the host

Haris Odobasic is Managing Partner at Revenue Wizards (https://revenuewizards.com/), a GTM and RevOps consultancy, and the author of The RevOps Pendulum (https://geni.us/revops-pendulum). He writes and speaks about how AI is changing the way companies are built and scaled.

LinkedIn: https://www.linkedin.com/in/harisodobasic/
X: https://x.com/OdobasicHaris

Growth After Headcount — The Podcast (Trailer)

Haris Odobasic — Wed, 22 Jul 2026 19:55:01 GMT

The old playbook said scale revenue by scaling people. That playbook is dead.

A new generation of companies is running on AI instead of headcount. Small teams, serious revenue, and org charts that would have looked impossible three years ago. This podcast goes inside those companies to find out how they actually work, from the founders building them.

Each episode is a conversation with someone running an AI-native company: what they automated, what they didn't, what broke, and what the numbers really look like. No hype, no "AI is transforming business" filler. Just how these companies are built and what it means for everyone still hiring the old way.

The podcast runs alongside the book of the same name, Growth After Headcount: How to Scale a Company with AI Instead of People.

New episodes coming soon. Subscribe so you don't miss the first one.

🔗 Website & newsletter: https://www.growthafterheadcount.com/

About the host

Haris Odobasic is Managing Partner at Revenue Wizards, a GTM and RevOps consultancy, and the author of The RevOps Pendulum. He writes and speaks about how AI is changing the way companies are built and scaled.

Connect with Haris:
LinkedIn & X

Growth After Headcount — What is this about? #001

Haris Odobasic — Tue, 21 Jul 2026 20:57:48 GMT

The old playbook said scale revenue by scaling people. A new generation of companies is throwing it out.

I'm Haris Odobasic, and this is Growth After Headcount — a podcast and a book about how companies scale with AI instead of headcount.

I come from revenue operations, where the whole job is aligning people, process, technology, and data into one efficient revenue system. It works, but it's still people-dependent. Plug AI into that system and something changes: a handful of people can run work that used to take a hundred. That shift is creating a new kind of company, built lean from day one, and it's putting pressure on incumbents who grew the old way.

Over the coming months I'll talk to the founders, investors, and operators building these companies. What they automated, what they didn't, what broke, and what the numbers actually look like. We'll get into the big questions too: can there be a one-person, billion-dollar company? What does a truly autonomous business look like when marketing, sales, service, and even the product improve themselves?

New episodes weekly. Occasionally it'll just be me. Everything feeds the book, out in 2027.

Follow along and build alongside me.

Haris Odobasic is Managing Partner at Revenue Wizards a GTM and RevOps consultancy, and the author of The RevOps Pendulum. He writes and speaks about how AI is changing the way companies are built and scaled.

Connect with Haris on LinkedIn or X