Product Lead - AI-Powered Learning & CultureOS (m/f/x)

About Sharpist

At Sharpist, we're on a mission to empower everyone to lead a self-aware career and life.

We're building the always-on career companion – from first internship to boardroom. For talents on the shop floor, in the stores, on the sites, and in the HQ. Before the hard conversation, after the tough feedback, in front of the empty whiteboard.

Our Hybrid Philosophy: Real 1:1 human coaching for empathy, accountability, and breakthrough moments – combined with an AI Coach for always-on support, follow-ups, and "in the moment" guidance.

Each learner's transcribed coaching sessions form their personal memory bank – their context, goals, patterns, and aha moments – securely encrypted. Our AI draws from this, rather than recycling generic knowledge.

This is not about replacing human coaches. It's about making coaching accessible to everyone, everywhere – and making HR teams 10x more effective.

The Strategic Context

We have strong product-market fit:

• World-class client logos (IKEA, BMW, Airbus, Adidas, SoundCloud, HomeToGo, Breitling)

• Clear market differentiation

• Clients switching to us from competitors because of our unique credit-based model

But the proof is in the pudding. We have two core challenges this role exists to solve:

1. Long-term retention of our core product – Pilots don't reliably convert to enterprise-wide rollout. We need to understand why and fix it.

2. Short-term activation and retention of our AI product – Our AI Coach is live with first customers and achieving strong ratings from those who use it. But the main challenge is adoption: getting people to the first session, then keeping them coming back.

We don't want incremental thinking. If you believe we should sunset products, build something entirely new, or pivot direction – we want to hear it.

The Team & Investment

Where we are today: Our Product & Engineering team is intentionally lean: 3 engineers, 1 data engineer, and 1 designer. Small, focused, and fast-moving. Our core product is nearing breakeven – we're a financially disciplined company, not a cash-burning startup.

Where we're going: Our existing shareholders are making a dedicated investment specifically to fuel Sharpist's AI transformation. This funding will allow us to double the P&E team over the coming year.

What this means for you:

• You'll have meaningful influence in hiring and shaping the team you'll lead

• You'll work with a small, high-trust group where decisions happen fast

• You'll have the resources to execute on AI – this isn't a side project, it's our strategic bet

• You'll need to be comfortable building with constraints while scaling thoughtfully

The Role

As Product Lead, you will own the full product experience across Sharpist's platform – with a strategic focus on our AI product expansion and the evolution toward CultureOS: a complete system connecting Memory Bank, Hybrid Journeys, and an Insights Dashboard for real-time workforce intelligence.

You'll report directly to the CEO and work at the intersection of Product, Engineering, Design, and commercial teams. This is a leadership role for someone who can think in 3-year horizons while shipping weekly – and who can grow a team while delivering results.

What You'll Do

Product Strategy & Vision

• Define and own the 1-3 year product strategy for the evolution from AI Coach to CultureOS

• Shape how our three strategic pillars come together:

  • Memory Bank: AI coaching sessions that continuously learn about each learner – their goals, context, growth, and aha moments over time

  • Hybrid Journeys: Combined human coaching & AI coaching with seamless handoffs – 75% AI for always-on support, 25% human for empathy, accountability & breakthroughs

  • Insights Dashboard: Conversational interface for HR to understand trends affecting retention, succession, and transformation

• Advise C-level on product-market fit, pricing models, and competitive positioning

• Identify when to pursue incremental improvements vs. step-change big bets

Crack the Adoption Challenge

This is your core mission. From our experience:

• Two-stage problem: Getting users to onboarding is one challenge; getting them to start their first session is another. Some client cohorts achieve near-100% conversion of attendees to active users; others struggle significantly. Understand why and fix it.

• Retention vs. excitement: AI solutions are great at generating initial excitement but struggle with long-term retention. Users need reasons to come back – we're investing in solving this and need you to lead the way.

• Coach adoption matters too: Coaches must opt in to transcription features alongside learners. Some are enthusiastic ("I use AI for every session"); others are skeptical ("I'm afraid about confidentiality"). You'll need to address both sides.

AI Product Differentiation

• Maintain and extend our differentiation from general-purpose AI: Sharpist responds with coaching questions (52 words) where ChatGPT gives generic advice (372 words). We're a coaching conversation, not a textbook.

• Drive the Gold Standard Quality architecture: ICF Competencies Agent (auditing against 8 core coaching competencies), Coach Challenge Level Agent (balancing gentle vs. provocative), Validation Techniques Agent (preventing "over-validation" that feels robotic), and 12+ additional quality agents

• Shape the integration between human coaching transcripts and AI follow-up sessions – unlocking the power of looking back across multiple transcripts to surface blind spots and patterns

• Define success metrics that go beyond sessions held – goal completion, behavior change, business outcomes like retention and absenteeism

Conversational Dashboard for HR

• Build the vision for HR to chat with aggregated coaching insights – surfacing skill development correlation, program engagement, and coaching access risk

• Enable HR to ask questions like: "What are the top recommendations to achieve our program outcomes?" or "Which departments have the highest coaching engagement?"

• Always on aggregated data, never individual transcripts – end-to-end encryption and privacy are non-negotiable

Build & Lead the Team

• Shape the hiring plan as we double the P&E team – you'll have significant input on who we bring in

• Work closely with Engineering, Design, and Data to ensure we're building the right capabilities

• Foster a culture of ownership, speed, and client obsession

• Balance building for today with investing in the foundations for tomorrow

Discovery & User Understanding

• Together with our Design Lead, run user research across all user groups – from enterprise HR to shop floor workers at companies like PALFINGER

• Build deep understanding of why users adopt (or don't) – the emotional journey matters as much as the functional one

• Run experiments, concept tests, and A/B tests to validate product hypotheses

• Synthesize qualitative and quantitative insights into clear product direction

Execution & Delivery

• Break down strategy into feature epics, user stories, and prioritized backlogs

• Maintain healthy roadmaps across mobile, web, and AI surfaces

• Work closely with the Design Lead to ensure exceptional UX

• Get your hands dirty: prototype with Figma, Lovable, v0, or whatever tools you're comfortable with

Success Milestones

Within 1 Month

• Deep immersion in Sharpist's product ecosystem, AI Coach architecture, and user research

• Shadow customer conversations, coach town halls, and learner interviews

• Assess current product strategy and form your hypothesis on the core retention and activation challenges

• Build strong working relationships with the existing P&E team

Within 1 Quarter

• Own and communicate a clear AI product strategy with defined success metrics

• Ship at least several meaningful improvements to AI Coach activation or retention

• Present your perspective on which products to double down on, sunset, or pivot

• Contribute to hiring plan and help bring in key new team members

Within 1 Year

• Demonstrate measurable improvement in AI Coach adoption and retention

• Drive meaningful improvement in pilot-to-enterprise conversion

• Launch at least one major capability that differentiates Sharpist from AI-only competitors and general-purpose tools

• Successfully scale the P&E team while maintaining velocity and culture

• Establish the foundation for CultureOS with integrated Memory Bank, Hybrid Journeys, and Insights Dashboard