Head of Product

Building tools that power modern business. Not content. Not theory.

Actual systems people use to make money, save time, and scale.

Contrarian Thinking is building the operating system for modern operators.

We sit on top of millions of people who want to buy businesses, grow them, and generate cash flow. Most don’t fail from lack of information -- they fail from lack of execution.

We fix that.

We build:

• Tools that turn ideas into action
• Systems that replace guesswork with data
• Products that collapse time from “thinking” → “doing”

This is not a media company. It’s a technology company with distribution.

We're hiring a Head of Product to turn ideas into shipped products -- fast.

This is not a roadmap theater role. You own 0→1 builds, iterate in public, and tie everything to revenue or retention. But more than that -- you're running a startup inside a startup. That means you hold the vision, make the calls, absorb the ambiguity, and keep moving when the org can't give you a clean answer. You've done this before. You know the difference between a product strategy and a product fantasy, and you don't confuse activity with progress.

You work with leadership to pressure-test ideas before they become projects, and to kill projects before they become debt. You translate business goals into product bets, not backlogs. When you come to the table, you come with a point of view -- on what to build, what to cut, and what success actually looks like in 90 days. You push back. You're comfortable being wrong. You make the call anyway.

The one-dimensional product person doesn't survive here. You have an eye for design -- not the ability to hire someone who does. You can look at a screen and know something is off before a designer tells you why. You're just technical enough to know what's hard, what's not, and when an engineer is sandbagging. You understand unit economics well enough to write the business case yourself. You've managed agencies, briefed offshore teams, and you know the difference between a vendor who needs direction and one who needs to be replaced. Your juniors should learn from watching you work -- not just from following your instructions.

• Own product strategy across web, AI, and internal tools
• Ship MVPs quickly (days/weeks, not quarters)
• Translate members data + audience data into product decisions
• Partner with growth to monetize (funnels, upsells, LTV)
• Build and manage a small, high-output developer & design team
• Define metrics that actually matter (usage, revenue, retention)

• Cloud & Data: GCP, BigQuery (or similar cloud/data warehouse experience)
• CRM & Ops: HubSpot (or equivalent CRM systems)
• Integrations: Slack, Zoom, Avoma (or comparable SaaS tools)
• Data Pipelines: Fivetran, Airbyte (or other ETL/ELT tools)
• Development:
  • Modern frontend frameworks (React, Next.js, or similar)
  • Backend systems (Node, Python, or equivalent)
• Tooling: AI-assisted development (e.g. Claude, Replit or similar tools)

• You’ve built and shipped multiple products (not just managed them)
• You’re technical enough to work directly with engineers
• You default to action over decks
• You care about business outcomes, not feature lists
• You’ve worked in fast-paced, founder-led environments

• Experience with AI products or LLM integrations
• Experience building data pipelines or internal tooling
• Creator economy, media, or education products

Fast. Practical. No theater.

1. Intro Call (20 min): Alignment, background, speed check
2. Build Exercise (2–4 hours max)
   • Take a real product idea
   • Outline + prototype how you’d ship it
   • Focus: speed, clarity, decisions
3. Deep Dive (45 min): Walk through your thinking live
4. Follow-Up Interview(s)
5. Founder Conversation: Final alignment on ownership + expectations

Full-time, in-office role at our Austin, Texas headquarters. Applicants must reside within a 1-hour drive of Austin or be willing to relocate.

• Health Coverage: Comprehensive medical, dental, and vision plans to support you and your family
• 401(k) with Company Match: Competitive match to help you build long-term financial security
• Flexible Time Off:  Take the time you need to perform at a high level—no unnecessary constraint
• Ownership & Upside: Compensation is structured to reward impact, with meaningful performance-based upside tied to the success of the products and business
• Build Your Own Lane: Opportunity to take on increasing responsibility, lead initiatives, and shape the direction of the company as it grows