Monetization StrategistPaid.ai • San Francisco • In-person • Full-time
The RoleWe're hiring a Monetization Strategist. You'll be the person prospects and customers turn to when they need to answer the hardest commercial questions in software: how much do we charge for AI, how, and how do we justify it. This is a founding role: you'll be the first strategist based full-time in San Francisco.
You'll pair with the Paid Sales team, interfacing directly with founders and C-suite executives in live sales cycles, during implementations, and long after the contract is signed. You'll diagnose monetization problems, design the packaging and pricing that achieves their objectives, make sure it actually gets implemented in Paid, and validate that it works in the market. This is a practitioner's role, not an advisory one: your recommendations get implemented in software you help configure, for customers whose renewal depends on your being right.
This is a multifunctional job sitting at the heart of the company: you'll be working with Sales to land customers, Product to help shape what we need to build, and Growth on our go-to-market motion. It's an opportunity to come in on the ground-floor, take on increasing responsibility as the business scales, and build out new business functions.
What You'll Do- Be directly responsible for our business' and our customers' success
- Architect monetization strategies with founders and executives as part of live sales cycles: diagnose issues with their current model, review potential paths forward, and convince them that Paid is the solution
- Own the monetization outcome after signature: translate the agreed model into value metrics, value rules, and pricing configuration in Paid
- Oversee project management of the implementation, mobilizing Paid and customer resources to drive a successful and swift launch into the market of the new model
- Guide customers through the internal work a pricing change actually requires: internal functional alignment, customer migration and grandfathering, sales enablement, customer communication, etc.
- Own the ongoing relationship, acting as a trusted partner to customers, self-critically reviewing their monetization and helping to refine it over time, alongside expanding their use of Paid's capabilities
- Codify the methodology into playbooks, diagnostics, benchmarks, and packaging archetypes for AI-native businesses, ensuring our knowledge scales beyond any one person and ultimately into a hybrid human/agentic practice
- Contribute to business development and thought leadership: proposals, POV pieces, and market-facing content that make the next conversation faster
- Bring what you learn back into Paid's product, positioning, and our own pricing
- Coach and raise the bar across the team as the function grows
What We're Looking ForMust have- Directly relevant experience in at least one but ideally both of: a pricing or commercial strategy consultancy practice working on software pricing, or an in-house role owning pricing or monetization at a software company
- Ability to engage with senior stakeholders one-on-one: we need to trust you to be alone in a room with an intelligent and skeptical founder
- Demonstrated experience managing projects end-to-end, from design through delivery
- Strong analytical capabilities and attention to detail, alongside pragmatism about when they're required
- Significant interest in the AI ecosystem, fluency in recent developments, and an understanding of underlying unit economics
- The willingness and ability as a front-line operator to build spreadsheets, presentations, processes, playbooks, etc., from scratch yourself utilizing AI
- Strong motivation to take accountability and drive successful customer outcomes, no matter what that takes
- Based in or willing to relocate to San Francisco, willing to travel 10% of the time
Nice to have- Experience with usage, output, or outcome-based pricing
- Start-up experience in a fast growing tech company
- Ability to advise on Sales best-practices: operating models, compensation scheme design, target & quota setting, etc.
- Technical fluency: you're comfortable discussing APIs, SDKs, and OpenTelemetry
- Ability to write clear, concise, and elegantly worded prose
- Front-line experience with a pricing migration and its aftermath: grandfathering, sales enablement, the customer conversations nobody enjoys
The expected base compensation for this role is $180k to $220k + equity options.
