GM, Digital Products (Remote)

Chiefly; United States; On-site; USD 120,000 - 160,000; Full time

Job summary

A growing education brand in the United States seeks a GM, Digital Products to lead their first SaaS subscription product. This role involves owning the digital revenue engine and launching the flagship subscription platform to a waitlist of over 3,000 potential customers. Ideal candidates will possess strong leadership skills, a successful background in SaaS products, and a data-driven mindset. The company emphasizes autonomy, high standards, and a quirky brand voice in a fully remote environment.

Qualifications

• Experience taking a subscription product from launch to thousands of paid subscribers.
• Can lead a small team and command respect.
• Must have technical skills to work with engineers.

Responsibilities

• Own the digital revenue engine for the brand.
• Launch flagship subscription product to a 3,000+ person waitlist.
• Build full funnel and customer journey strategies.

Skills

SaaS/Digital Product GTM

Product-led growth chops

Pricing, packaging, retention

Life cycle + CRO execution

Technical literacy

Leadership

Founder-led brand savvy

Direct-response chops

Data-informed

Adaptable

Job description

Overview

Chiefly connects exceptional operators with scaling internet businesses. We present this role on behalf of our partner:

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GM, Digital Products

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

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

• Title: GM, Digital Products
• Position: Leadership team
• Reporting: Direct to Founder
• Compensation: $120,000 - $160,000 USD base + performance-based upside
• Business Model: SaaS/Digital Subscriptions, Books, Tutoring
• Stage: Highly profitable, bootstrapped, scaling
• 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
• Own the digital revenue engine for a brand with massive built-in demand.
• Launch the flagship subscription product to a 3,000+ person waitlist.
• Work with a founder who demands quality but gives total execution autonomy.
• Build your machine your way - no bureaucracy, PE overlords, no exit pressure.
• 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 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.
• 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.
• Intensity: You play to win.
• 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.
• 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.
• 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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