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We're looking for a Senior Product Manager to own TokenShift, PointFive's product for finding and cutting wasted AI token spend. This is a chance to define product strategy for a brand-new category, working hands-on with R&D on how AI agents and LLM models actually run, get monitored, and get paid for in production. You'll take TokenShift from early adoption to a core pillar of PointFive's platform, alongside our flagship DeepWaste product.
What You'll Do:
Own the product strategy and roadmap for TokenShift, from discovery through GA and beyond.
Translate a deep technical understanding of how AI agents and LLM workloads run, inference calls, endpoints, agent harnesses and orchestration, into requirements R&D can build against.
Partner with R&D, design, and data science to scope, prioritize, and ship features that surface and reduce AI token waste.
Work directly with enterprise customers and prospects to understand how they deploy AI agents in production and where their cost and visibility gaps are.
Define and track success metrics, adoption, cost savings, detection accuracy, and use them to drive roadmap decisions.
Collaborate with go-to-market teams on positioning, messaging, and launch plans for new capabilities.
Stay current on the landscape: coding agents and harnesses, LLM gateways and routers, AI observability, and endpoint management.
Represent the voice of the customer internally, balancing technical depth with business impact.

we are looking for a AI Data Lead.
As Data Lead, you will own how data gets turned into decisions across the company - and lead the shift from traditional BI into AI-driven BI, powered by agents that surface insight in real time. You'll work closely with one data engineer today, with room to grow the team as scope expands.
You'll define what the data function looks like when AI is embedded in it, not bolted on - from the underlying infrastructure to the dashboards and agents people actually use. The playbook for AI-native BI is still being written, and you'll write a lot of it.
Key Responsibilities
Data Strategy & Ownership:
Own the vision and roadmap for the data function, including the shift from classic BI to agent-based, AI-driven BI
Set priorities in partnership with senior leadership
Work closely with a data engineer today, with the option to grow the team as the function scales
AI-Driven BI & Agents:
Drive adoption of AI across data workflows - from automating analyses to agents answering business questions in real time
Own the semantic and metrics layer so every dashboard and every agent reads the same definitions
Build in a git-based workflow: dashboards and queries live in git, edited through PRs, built with agents
Expose our data to agents over MCP so business questions get answered without waiting for a dashboard
Define where AI speeds things up - and where human judgment still has to hold the line
Infrastructure & Analytics:
Own the data infrastructure: BigQuery, dbt, pipelines, and data reliability
Lead complex analytics work, A/B testing, and impact measurement, hands-on
Define evals and quality metrics for AI features and agents - not just A/B tests on dashboards
Cross-functional Collaboration
Partner with product, marketing, finance, operations, and engineering to define analytical needs and turn them into solutions
Represent the data function to the organization - senior-level storytelling with data

We are looking for a Customer Support Operations Lead to define how high-touch support operates as we expand. This role sits at a unique intersection: one side involves shaping our support people operations through structured training, QA frameworks, and actionable feedback loops, while the other centers on constructing the AI tooling and systems infrastructure to power it. Both pillars must scale side-by-side as our organization expands, creating a distinct blend of human touch and technical building that sets this position apart.
This is a builder's role, not a people management one. You won't manage agents day to day, but the systems, training, and technology you build will shape how the whole team works, and how members experience us in some of their most sensitive moments. You'll partner closely with support leadership on hiring, coaching, and escalations, and with product and dev on new flows, automations, and AI infrastructure. You'll also take part in shaping our AI and support strategy: helping decide what moves to AI and what still needs a human touch, and owning our sources of truth so they stay accurate and current, using smart, efficient ways to keep them that way.
If you're excited by combining hands-on human coaching and training with hands-on AI and systems building, and you want a role with real ownership and cross-team reach, this is that role.

we are looking for a Head of Product, AI Therapy.
As a Head of Product - AI Therapy, you will own how AI and clinical expertise come together across the product to create a new kind of therapy experience. This role sits at the intersection of consumer product, AI technology, and clinical science - defining what intelligent relationship support looks like when it's grounded in real therapeutic data and validated by real clinicians.
You'll design the conversational AI that supports users between sessions - emotional processing, conversation preparation, reflections, personalized guidance. You'll build the intelligence layer that turns therapy session data into structured relationship context, so every interaction feels informed by the couple's actual journey. And you'll push into open space - new product surfaces, new modes of support, new ways to make therapists more effective - because the category is being created now and the playbook doesn't exist.
This is a hands-on role that requires balancing vision with execution, working closely with our clinical lead, AI engineers, and design team to ship products where every word matters - because people are vulnerable when they use them. In regular collaboration with founders and clinical leadership, you'll shape the AI therapy strategy and help define the future of continuous, tech-enabled relationship support.

We are looking for a Generative AI Engineer to lead our AI efforts end-to-end - from infrastructure and production systems to internal adoption and cross-team enablement.
You will play a significant role in building the world's first Consumer Therapy AI Product (someone said RAG? But we mean a real one that works in production...).
This is a critical role in a high-growth, fast-paced B2C startup, requiring a leader who can advocate for Engineering requirements, tech-debt and best practices while promoting a product-mindset and putting our customers front and center.