EvenUp

Role Description Join EvenUp as a Staff Machine Learning Engineer and help set the technical direction for how machine learning powers Piai™, our proprietary claims-intelligence platform. This is a technical leadership role - you'll shape modeling strategy across a broad problem space, turning raw legal and medical data into production systems that improve outcomes for personal-injury clients. You'll partner closely with Product, Research, and Engineering leaders to set strategy, and you'll be a technical anchor for the broader ML team - setting standards, mentoring senior engineers, and driving decisions that shape both product outcomes and company growth. What You'll Do - Set technical strategy for a broad area of the ML roadmap, translating ambiguous business and research goals into scoped, production-ready systems. - Tackle the hardest modeling problems in the org - complex reasoning, long-context and multi-document understanding, or other frontier challenges as they come up. - Apply advanced ML techniques - fine-tuning, reinforcement learning, retrieval, or others - and know when a technique is the right tool versus over-engineering. - Establish rigorous evaluation standards, reducing hallucinations, improving factual consistency, and defining what "good" looks like for a given system. - Drive data excellence through hands-on analysis of training and evaluation data, managing noise, edge cases, and drift at scale. - Provide technical leadership and mentorship across the ML team, raising the bar for experimentation, benchmarking, and engineering rigor. - Act as the bridge between research and production - ensuring new techniques get integrated into shippable systems, not just proofs of concept. - Partner cross-functionally with product, engineering, and legal subject-matter experts to set technical direction. - Cost effectively scale practical machine learning systems in a hyper-growth environment, ensuring they remain grounded in real business and customer needs. Qualifications - 7+ years of hands-on ML engineering experience, with multiple models shipped and running in production. - Deep expertise in ML and NLP, including LLMs, with a track record of solving hard modeling problems - not just applying existing recipes. - High proficiency in Python and strong command of modern ML/NLP frameworks. - Demonstrated ability to set technical strategy and drive execution in ambiguous, fast-moving environments. - A track record of mentoring engineers and raising technical standards beyond your own output. - Experience partnering directly with Product and Engineering leadership, not just executing their asks. Nice to Have - PhD in Machine Learning, Computer Science, or a related quantitative field. - Experience with document understanding, entity/relationship extraction, or structured extraction from unstructured text. - Experience with LLM fine-tuning techniques (LoRA, QLoRA, RLHF/RLVR) or advanced prompt engineering. - Experience in a high-growth startup environment. - Open to remote candidates or 3 days a week hybrid from our Toronto or San Francisco hubs. Benefits - Choice of medical, dental, and vision insurance plans for you and your family. - Additional insurance coverage options for life, accident, or critical illness. - Flexible paid time off, sick leave, short-term and long-term disability. - 10 US observed holidays, and Canadian statutory holidays by province. - A home office stipend. - 401(k) for US-based employees and RRSP for Canada-based employees. - Paid parental leave. - A local in-person meet-up program. - Hubs in San Francisco and Toronto.

• Open insurance claims and serve as the primary liaison with adjusters and carriers. • Request, track, and organize medical records, bills, and police reports. • Ensure treatment progression and awareness of treatment outcomes. • Identify and proactively resolve lien and subrogation issues. • Collaborate with lead paralegals to prepare complete, accurate case files for demand. • Communicate with clients daily to guide them through the pre-litigation process. • Maintain case timelines and ensure milestones are met with precision. • Spot and eliminate operational inefficiencies to drive speed and accuracy. • Uphold the highest standards in documentation, file integrity, and communication.

• Lead the design, development, and optimization of robust frontend systems for deploying LLM-based algorithms and services. • Manage projects through their complete lifecycle—from architecture to deployment, monitoring, and improvement. • Work with other engineering teams to understand use cases and deliver scalable platform solutions. • Develop high-quality, maintainable code using a modern tech stack. • Grow as an engineer working alongside world-class peers on impactful, cutting-edge generative AI projects.

• Manage, coach, and develop a team of 2–3 SMB Customer Success Managers. • Build a performance culture grounded in clear metrics, regular feedback, and accountability. • Hire and onboard future team members as the SMB segment grows. • Design and operationalize a digital-first CS motion that drives adoption, retention, and expansion across a high-volume SMB customer base. • Build and optimize automated lifecycle programs — onboarding sequences, health-based triggers, renewal campaigns, and re-engagement workflows — using tools like Salesforce, HubSpot, or equivalent. • Develop and maintain a library of digital touchpoints including in-app messaging, email nurture sequences, self-serve onboarding resources, and video content. • Identify where human intervention adds the most value and design the motion accordingly, protecting CSM time for the highest-impact moments. • Own GRR and NRR targets for the SMB segment. • Monitor customer health signals and ensure the team is proactively addressing risk before it becomes churn. • Partner with Account Managers to identify expansion and upsell opportunities within the SMB base. • Establish and track leading indicators that predict renewal outcomes 60–90 days in advance. • Build and maintain dashboards that give CS leadership real-time visibility into team performance, customer health, and segment-level risk. • Define and track the KPIs the team is measured against, including adoption milestones, health scores, renewal rates, and response SLAs. • Partner with CS Ops, Product, Support, and Marketing to continuously improve the digital customer experience.

Role Description We’re looking for a Senior/Staff User Researcher to build, execute, and scale a comprehensive research engine that directly informs our product strategy. In this highly cross-functional role, you will act as a "full-stack" researcher, taking ownership of the three critical pillars of our research motion: - Research Operations - Hands-on Mixed-Methods Research - Early Discovery Strategy You will roll up your sleeves to build our Research Ops infrastructure from scratch, managing participant recruitment, compliance, and tooling. Beyond operations, you will conduct rigorous qualitative and quantitative studies ranging from deep-dive focus groups to sentiment benchmarking. You will also act as a deeply embedded strategic partner to Design, Product, and Engineering leadership, helping the business validate early concepts and shaping strategy proactively. What You’ll Do - End-to-End Research Ops: Build and scale the foundational infrastructure for our research practice, managing participant sourcing and implementing modern research tools. - Mixed-Methods Research Execution: Design and conduct rigorous qualitative and quantitative research, analyze user engagement, run sentiment analyses, and execute surveys, focus groups, and targeted 1:1 user interviews. - Strategic Discovery Research: Lead early-stage exploratory research to evaluate product concepts, partnering with leadership across Design, Product, and Engineering. - Creative Artifact Generation & Business Alignment: Synthesize complex data into memorable artifacts that connect user pain points to ARR opportunities. - Cross-Functional Collaboration & Action: Proactively identify research needs based on quantitative engagement data and develop actionable recommendations. How Success Is Measured - Strategic Impact: Recognized as an influential partner in the product development lifecycle, informing the product roadmap. - Analytical Rigor: Research outputs represent a mix of quantitative data and qualitative insights. - ResOps Scalability: Establish clear, repeatable, and compliant operational systems. - Product & Business Impact: Findings translated into actionable proposals that drive feature adoption and influence ARR growth. Qualifications - 5+ years of work experience in UX Research, Product Research, or a related field within a fast-paced B2B tech environment. - Exceptional analytical skills, comfortable with both quantitative data and presenting macro-level ARR opportunities. - Proven track record of handling the logistical side of research, including compliance and participant management. - Strategic business acumen, able to connect user behaviors to revenue opportunities. - Ability to operate in detail while also building scalable systems and presenting proposals. - Outstanding communication and storytelling skills, producing exceptional research artifacts. Nice to Have - Prior experience acting as a founding researcher or establishing a Research function from the ground up. - Experience leveraging AI to accelerate qualitative data synthesis or operations. Benefits - Choice of medical, dental, and vision insurance plans for you and your family. - Additional insurance coverage options for life, accident, or critical illness. - Flexible paid time off, sick leave, short-term and long-term disability. - 10 US observed holidays, and Canadian statutory holidays by province. - A home office stipend. - 401(k) for US-based employees and RRSP for Canada-based employees. - Paid parental leave. - A local in-person meet-up program. - Hubs in San Francisco and Toronto.

• Own the technical and operational setup for our customers. • Translate firm Standard Operating Procedures into EvenUp by setting up Smart Workflows, task plans, and document templates. • Draft, test, and refine prompts, exercising strong judgment on quality thresholds for v1 launches. • Write and execute SQL queries to configure custom firm reports, ensuring data accurately reflects the firm's needs. Manage complex data mapping, including provider contact entity linking. • Design User Acceptance Testing (UAT) end-to-end scenarios, conduct UAT alongside extended teams, provide mock plugs for integrations, and meticulously validate all use cases in staging environments to ensure production readiness. • Draft training schedules, coordinate with external stakeholders, and partner with internal ops teams to update internal processes (e.g., mailroom/fax attribution). • Triage critical failures during rollout, identify missed use cases, and prioritize them in the product backlog to continuously improve the platform.

• Own the editorial calendar: Build, maintain, and execute a weekly and quarterly content calendar aligned to company priorities • Write and edit content: Produce and edit content across multiple formats and channels, including blogs, executive thought leadership, customer stories, product narratives, and company announcements • Translate complexity into compelling narratives: Turn complex AI, legal, and business topics into clear, engaging, and customer-focused content • Set and maintain editorial standards: Ensure all content meets high standards for accuracy, clarity, tone, structure, and consistency across channels • Conduct research: Independently research topics, validate claims, and synthesize information into clear narratives • Apply a customer-first lens: Ensure content addresses real customer questions, pain points, and industry trends • Partner cross-functionally: Work directly with Product, Marketing, Sales, Customer Success, and executives to source stories and align messaging • Drive thought leadership: Help shape executive and company narratives that position EvenUp as a leader in AI and legal technology • Own narrative intelligence: Track industry trends, media coverage, customer conversations, and competitive positioning to identify where EvenUp should lead or proactively enter the conversation • Track performance: Monitor content performance and refine editorial strategy based on results and audience engagement

• Own and drive the post-sale onboarding process for new EvenUp customers, ensuring they achieve rapid adoption and sustained value from our platform. • Lead strategic onboarding sessions, coordinate with cross-functional teams, and work directly with key decision-makers and end-users. • Maximize trial utilization and enhance customer retention and satisfaction through proactive onboarding management. • Develop and deliver high-impact onboarding and training sessions to equip customers with the skills necessary to use EvenUp’s platform effectively. • Collaborate closely with Account Executives (AEs), Customer Success Managers (CSM), Product, Legal/Medical Operations, and Engineering teams to ensure customer requirements and feedback are promptly addressed. • Engage with key decision-makers and firm champions to establish strategic success metrics and ensure alignment on implementation milestones.

• Craft Strategic Narrative & GTM: Define the value proposition and messaging for EvenUp’s platform—spanning core capabilities, integrations, and cross-product features. Drive go-to-market strategies that shape positioning, launches, campaigns, and ecosystem engagement. • Partner with Product, Sales & Engineering: Collaborate closely with product management, sales, customer success, and enablement to align roadmap priorities, messaging, and launch strategy. • Think Creatively About Content & Campaigns: Bring fresh, out-of-the-box ideas to how we tell our story in the market. Develop compelling collateral, campaigns, and creative assets—ranging from solution briefs to demos to thought-leadership content—that capture attention and resonate with diverse audiences. • Build Strong Customer Relationships: Engage directly with customers to deeply understand their needs, workflows, and aspirations. Use these insights to refine messaging, shape campaigns, and create customer-centric content. Develop advocates who can amplify our story through case studies, testimonials, and co-marketing opportunities. • Enable Sales & Internal Teams: Create imaginative enablement materials—such as sales playbooks, competitive insights, one-pagers, solution briefs, presentations, and demos—to empower teams to articulate platform value with confidence and creativity. • Launch & Market Expansion: Lead platform-level launches and promotional initiatives. Experiment with new ways to engage customers and prospects across digital, social, analyst relations, events, and demand generation. • Research & Competitive Analysis: Conduct market research, competitive intel, and customer insights to refine messaging, uncover new opportunities, and support strategic planning.

• Serve as the primary owner of client outcomes, maintaining end-to-end accountability for the project lifecycle and proactively navigating obstacles to drive implementations to a successful, high-impact completion. • Develop and manage a comprehensive project plan for each customer enterprise platform delivery, ensuring alignment with customer needs and company goals. • Oversee workstreams including data migration, system configuration, user onboarding, change management, and go-live support. • Coordinate with Product, Engineering, and customer project teams to deliver on time and within scope. • Provide project health, status and risk management oversight, keeping various internal and external customer sponsors engaged. • Configure platform settings, including user permissions, workflow rules, and reporting tools, to meet customer requirements. • Ensure secure and scalable access controls, including API integrations, in collaboration with Engineering teams. • Lead User Acceptance Testing (UAT) to validate platform functionality and usability. • Deliver onboarding programs, including end-user training for operational staff and executive training for leadership teams. • Leverage change management principles to ensure training programs drive adoption and minimize disruption. • Design and implement customer adoption strategies using change management fundamentals to ensure high user engagement and platform success. • Develop and execute tailored adoption and programs, including stakeholder communication plans, training initiatives, and feedback loops to address resistance and build buy-in. • Drive user adoption through proactive change management, hands-on support. • Provide break-fix triage during platform deployment to address critical issues. • Monitor system performance and uptime to ensure reliability for customers. • Conduct regular status meetings with customers to gather feedback and ensure satisfaction. • Act as the primary point of contact for customer project teams, facilitating requirements gathering and adoption feedback. • Travel to customer sites (up to 30% travel) to support onboarding, training, and go-live activities. • Build strong relationships with enterprise stakeholders to ensure alignment and success.