Head of Product & Growth

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Head of Product & Growth

Premium Test Prep & Education

Scale an established education brand's first SaaS subscription product.

Join a rapidly growing $3M bootstrapped business built on organic demand.

🎯 ROLE SNAPSHOT

• Title: Head of Product & Growth
• Position: Leadership team
• Reporting: Direct to Founder
• Compensation: $120,000 - $160,000 USD base + performance-based upside

🏢 COMPANY OVERVIEW

• Industry: Education & Premium Test Prep
• Business Model: SaaS/Digital Subscriptions, Books, Tutoring
• Stage: Highly profitable, bootstrapped, scaling
• Revenue: $3M+ annual (zero funding, zero ad spend)
• Founder: leading expert, 15-year track record, published author
• Brand: Cult-favorite brand, 30K+ books sold annually
• Team: Lean remote team (~5 core + devs)
• Location: 100% Remote
• Culture: Intense, excellence-obsessed, transparent
• Values: Student outcomes, quirky brand voice, no corporate BS

⭐ THE OPPORTUNITY

• Own the digital revenue engine for a brand with massive built-in demand.
• Launch the flagship subscription product to a 3,000+ person waitlist.
• Inherit unfair advantages: established brand, proven PMF, zero paid acquisition to date.

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• Work with a founder who demands quality but gives total execution autonomy.
• Build your machine your way - no bureaucracy, PE overlords, no exit pressure.

🎯 KEY RESPONSIBILITIES

• Launch the subscription platform to the 3,000+ waitlist members.
• Own the full funnel and customer journey: free -> paid -> retained.
• Own pricing, packaging, monetization, and the subscription growth roadmap.
• Build product growth loops & retention (virality, referrals, engagement).
• Build lifecycle messaging + winback (in-product + email).
• Build data infrastructure, dashboards, reporting, and metric definitions from 0→1.
• Run a tight shipping + experiment cadence, and hold vendors/contractors/teammates to a high standard.

📋 MUST-HAVES

• SaaS/Digital Product GTM: taken a subscription product from launch → thousands of paid subscribers.
• Product-led growth (PLG) chops: you think in activation, retention, and compounding loops.
• Pricing, packaging, retention: you’ve materially improved churn/LTV.
• Lifecycle + CRO execution: landing pages, onboarding, email/in-product messaging, and experiments that ship.
• Technical literacy: can instrument tracking and work with engineers.
• Leadership: can lead a small team, command respect, and hold the bar.
• Founder-led brand savvy: can build inside a founder-led personal brand & voice without flattening it.

✨ IDEAL BACKGROUND

• Education, content, or creator-led brand experience.
• Converted an existing audience into paid subscriptions.
• Shipped under bootstrapped constraints (small team, low tooling).
• Direct-response chops: positioning, offers, landing pages, lifecycle email.
• Subscription mechanics ownership: trials, annuals, save flows, dunning, winback.
• Socials/content fluency, familiarity with SEO and paid strategy.

🧬 YOUR PERSONAL DNA

• Intensity: You play to win.
• Direct Communicator: you give clear feedback, fast decisions, zero drama.
• Ownership: "that's not my job" is not in your vocabulary.
• High Standards: "good enough" makes you uncomfortable.
• Comfortable with friction: you push back to protect outcomes.
• Low ego: confident, coachable, founder-aligned.

🧠 MINDSET

• Builder Mentality: energized by 0→1 and “nothing exists yet.”
• Ambiguity-proof: you write the playbook, then execute it.
• Bias to action: you see problems, and fix them.
• Adaptable: you flex to the business needs, regardless of title.
• Data-informed: the numbers decide what to ship, fix, or kill.

⚠️ NOT A FIT IF

• You're a pure “strategist” - this is hands-on, in-the-weeds work.
• You’re a pure a “performance marketer” - ‘turning on’ Meta ads isn't the strategy here.
• You’re a pure a “product manager” - this is a growth focused role.
• You want to outsource everything - "I'll just hire agencies" is a dealbreaker
• You'll fight the brand voice - the quirky personality is non-negotiable.
• You need rigid structure - no complex org charts or approval chains.
• You're slowing down - this is a build role, not a coast role.

🤝 IS THIS YOU? This role is for the leader who sees a $3M bootstrapped brand with a 3,000-person waitlist and thinks: "Give me 12 months and watch what happens."

Don't just apply - convince us you're the one to own this!

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Brought to you by Chiefly - connecting exceptional operators with scaling internet businesses.