15Five

• Lead and develop a team of Product Managers and Product Designers, serving as both a coach and a hands-on product leader. • Partner with the CTO and executive team to define and execute product strategy aligned with company goals. • Own multiple strategic initiatives from discovery through customer adoption, ensuring successful execution and business impact. • Drive product prioritization and decision-making using customer insights, data, technical considerations, and company strategy. • Champion selling the roadmap and future vision directly to customers. • Collaborate closely with Engineering, Design, AI, Data, Sales, Marketing, Customer Experience, Account Management, and other business leaders to deliver exceptional customer outcomes. • Foster a high-performing product organization with a culture of ownership, innovation, collaboration, and continuous improvement. • Stay at the forefront of AI technologies, tools, and best practices, championing AI-first product development and embedding AI into daily product management practices.

15Five is the AI-powered performance management platform built for business impact. 15Five’s AI-powered all-in-one people management system is easy to use,
delivers effortless insights, and enables managers to lead with impact so that companies and their people can thrive. Within the flow of work, HR leaders are empowered with data-driven insights and recommendations while managers are transformed into changemakers, accelerating engagement, performance, and retention. 15Five combines generative AI, custom analytics, and human-centered principles within a complete platform, including 360° performance reviews, engagement surveys, goal tracking, manager coaching and training, and ongoing feedback tools like guided 1-on-1s and check-ins. Working with 15Five is the chance to have high impact in a fast paced, remote startup environment that operates with focus, urgency, and accountability. Every role meaningfully impacts our trajectory. We’re a high-performance, high-purpose team that gives you the chance to build the future of work. If you're energized by a fast pace, high standards, and high accountability for yourself and others, you'll thrive here and we encourage you to apply. As a Fractional Certified Coach you work under a part-time contract to deliver one-on-one and group coaching to managers and leaders at 15Five customer organizations in APAC timezones. You will work within the 15Five coaching methodology, leveraging our platform data (engagement surveys, 1-on-1 insights, OKR progress, and review feedback) to inform and personalize each coaching engagement. Your mission is to coach managers to lead more effectively by driving measurable improvements in team engagement, retention, and performance. This role will require 5 or fewer hours per week and requires spoken and written fluency in English. Responsibilities - Deliver structured, outcome-oriented coaching engagements to people managers and senior leaders within 15Five customer organizations - Use 15Five platform data and analytics to tailor coaching conversations, identify development areas, and track progress against goals - Facilitate group coaching sessions, leadership workshops, and manager development programs as needed - Maintain timely and thorough documentation of coaching sessions, action items, and participant progress within 15Five systems - As needed, collaborate with 15Five teams to align coaching engagements with each customer’s strategic objectives - As needed, provide structured feedback to 15Five on coaching methodology effectiveness, participant trends, and product improvement opportunities - Adhere to ICF ethical guidelines and 15Five’s confidentiality standards in all coaching interactions RequirementsEducation - Graduate degree (Master’s or Doctorate) in Organizational Development, Psychology, Human Resources, Business Administration, or a closely related field - Fluent in English (spoken and written language) Certification - ICF Professional Certified Coach (PCC) credential required - Additional certifications in leadership assessment tools (e.g., Hogan, DISC, EQ-i 2.0, or 360-feedback instruments) are a plus Experience - Minimum of 5 years of professional coaching experience, with a strong emphasis on executive, leadership, or manager effectiveness coaching - Demonstrated track record of delivering coaching within B2B SaaS, technology, or high-growth environments preferred - Experience integrating data and technology platforms into coaching practice (e.g., engagement survey data, 360 feedback, OKR/performance tools) Time Zone Coverage - Coverage for APAC timezones Preferred Qualifications - Authorized to work as an independent contractor based in APAC - Prior experience coaching within a platform-embedded coaching program (e.g., BetterUp, Torch, Bravely, or similar) - Familiarity with the 15Five platform - Experience facilitating virtual workshops and group coaching in a remote-first environment - Strong understanding of people analytics, employee engagement drivers, and the link between manager effectiveness and business outcomes - Comfort operating as an independent contractor with the ability to manage your own schedule, invoicing, and client relationships within 15Five’s framework - Experience as a leader and/or people manager Compensation & Engagement Details - This is an independent contractor (1099) engagement. - Compensation is based on a per-session or per-engagement fee structure, commensurate with experience and credential level. - Scheduling is flexible and based on customer demand and your availability. All coaching is delivered remotely. - This role will require 5 or fewer hours per week. Note: This role will not cover US time zones.

15Five is the AI-powered performance management platform built for business impact. 15Five’s AI-powered all-in-one people management system is easy to use,
delivers effortless insights, and enables managers to lead with impact so that companies and their people can thrive. Within the flow of work, HR leaders are empowered with data-driven insights and recommendations while managers are transformed into changemakers, accelerating engagement, performance, and retention. 15Five combines generative AI, custom analytics, and human-centered principles within a complete platform, including 360° performance reviews, engagement surveys, goal tracking, manager coaching and training, and ongoing feedback tools like guided 1-on-1s and check-ins. Working with 15Five is the chance to have high impact in a fast paced, remote startup environment that operates with focus, urgency, and accountability. Every role meaningfully impacts our trajectory. We’re a high-performance, high-purpose team that gives you the chance to build the future of work. If you're energized by a fast pace, high standards, and high accountability for yourself and others, you'll thrive here and we encourage you to apply. As a Fractional Certified Coach you work under a part-time contract to deliver one-on-one and group coaching to managers and leaders at 15Five customer organizations in EU and UK time zones. You will work within the 15Five coaching methodology, leveraging our platform data (engagement surveys, 1-on-1 insights, OKR progress, and review feedback) to inform and personalize each coaching engagement. Your mission is to coach managers to lead more effectively by driving measurable improvements in team engagement, retention, and performance. This role will require 5 or fewer hours per week and requires spoken and written fluency in English. Responsibilities - Deliver structured, outcome-oriented coaching engagements to people managers and senior leaders within 15Five customer organizations - Use 15Five platform data and analytics to tailor coaching conversations, identify development areas, and track progress against goals - Facilitate group coaching sessions, leadership workshops, and manager development programs as needed - Maintain timely and thorough documentation of coaching sessions, action items, and participant progress within 15Five systems - As needed, collaborate with 15Five teams to align coaching engagements with each customer’s strategic objectives - As needed, provide structured feedback to 15Five on coaching methodology effectiveness, participant trends, and product improvement opportunities - Adhere to ICF ethical guidelines and 15Five’s confidentiality standards in all coaching interactions RequirementsEducation - Graduate degree (Master’s or Doctorate) in Organizational Development, Psychology, Human Resources, Business Administration, or a closely related field - Fluent in English (spoken and written language) Certification - ICF Professional Certified Coach (PCC) credential required - Additional certifications in leadership assessment tools (e.g., Hogan, DISC, EQ-i 2.0, or 360-feedback instruments) are a plus Experience - Minimum of 5 years of professional coaching experience, with a strong emphasis on executive, leadership, or manager effectiveness coaching - Demonstrated track record of delivering coaching within B2B SaaS, technology, or high-growth environments preferred - Experience integrating data and technology platforms into coaching practice (e.g., engagement survey data, 360 feedback, OKR/performance tools) Time Zone Coverage - Coverage for EU and UK time zones Preferred Qualifications - Authorized to work as an independent contractor based in the EU or UK - Prior experience coaching within a platform-embedded coaching program (e.g., BetterUp, Torch, Bravely, or similar) - Familiarity with the 15Five platform - Experience facilitating virtual workshops and group coaching in a remote-first environment - Strong understanding of people analytics, employee engagement drivers, and the link between manager effectiveness and business outcomes - Comfort operating as an independent contractor with the ability to manage your own schedule, invoicing, and client relationships within 15Five’s framework - Experience as a leader and/or people manager Compensation & Engagement Details - This is an independent contractor (1099) engagement. - Compensation is based on a per-session or per-engagement fee structure, commensurate with experience and credential level. - Scheduling is flexible and based on customer demand and your availability. All coaching is delivered remotely. - This role will require 5 or fewer hours per week. Note: This role will not cover US time zones.

15Five is the AI-powered performance management platform built for business impact. 15Five’s AI-powered all-in-one people management system is easy to use,
delivers effortless insights, and enables managers to lead with impact so that companies and their people can thrive. Within the flow of work, HR leaders are empowered with data-driven insights and recommendations while managers are transformed into change-makers, accelerating engagement, performance, and retention. 15Five combines generative AI, custom analytics, and human-centered principles within a complete platform, including 360° performance reviews, engagement surveys, goal tracking, manager coaching and training, and ongoing feedback tools like guided 1-on-1s and check-ins. A career at 15Five is the chance to have high impact in a fast paced, remote startup environment that operates with focus, urgency, and accountability. Every role and every hire meaningfully impacts our trajectory. We’re a high-performance, high-purpose team that gives you the chance to Build the Future of Work. We run on High Standards and High Support — holding a high bar for results, ownership, clarity, and disciplined execution, while investing in manager enablement, skill development, and whole-person care. We are committed to a No B.S. environment, meaning we anchor ourselves in truth, course-correct in real time, and expect people to lean into direct conversations. We are focused on ensuring every 15Fiver can Work in the Future and that starts with proactively using AI across all aspects of your role to increase leverage, speed, and impact. If you're energized by a fast pace, high standards, and high accountability for yourself and others, you'll thrive here and we encourage you to apply. Senior Software Engineer Remote (US) | Reports to: Sr. Director of Engineering We’re looking for a Senior Software Engineer to help build and evolve 15Five’s Data Intelligence Platform—the foundation that powers our AI, agentic capabilities, and data‑driven product experiences. You’ll work across a modern tech stack, partner closely with Data Science and Product Engineering, and help define the standards, tooling, and infrastructure that enable our next generation of AI‑powered features. Areas of Ownership - Build and evolve 15Five’s Data Intelligence Platform - Partner across Data Science and Product Engineering - Elevate engineering quality and culture What You’ll Do - Build and enhance the Data Intelligence Platform, including pipelines, tooling, and agentic infrastructure. - Partner with Data Scientists to develop AI platform capabilities, complex models, and agentic applications. - Own and improve existing autonomous agents; design, orchestrate, and deploy new ones across the product. - Implement best practices across software, data, and ML/AI engineering to strengthen our agentic ecosystem. - Build data models and pipelines that support the entire engineering organization. - Design scalable data platform features for ingestion, storage, validation, governance, monitoring, and ETL/reverse‑ETL. - Use AI‑assisted code generation effectively while ensuring code quality, security, and performance. - Review code and architecture, contribute to documentation, and elevate engineering standards. - Bring a product mindset to planning, helping shape vision, goals, and roadmap. What You Bring - 5+ years of software development experience with strong foundations in algorithms, data structures, and design principles. - Proficiency in languages used for data and AI (e.g., Python, Java, C++, Go, Scala) plus SQL and relational/NoSQL databases. - Solid understanding of data engineering concepts: ETL pipelines, data modeling, schema design, enrichment, and governance. - Experience with cloud‑native big‑data environments and optimizing for cost and performance. - Familiarity with Python frameworks (Django is a plus). - Experience or interest in MLOps, AI model development, or knowledge graphs. - Strong communication skills and comfort collaborating across engineering, product, design, and customer‑facing teams in a remote setting. Nice to Have - Experience with agentic systems or autonomous agents. - Exposure to DBT, Airflow, Snowflake, Django, or similar technologies. - Background in HR tech, people systems, or performance management. Work Schedule Fully Remote, Monday–Friday. Typical hours align with 7/8am–3/4pm PT or 9am–5pm ET, with flexibility. Some early‑morning meetings may be required to support cross‑time‑zone collaboration. Compensation & Benefits US Annual Salary, Senior Software Engineer: $120,500 - $160,000/ year This role's Total Rewards package includes participation in an annual discretionary company bonus program, equity awards, and comprehensive benefit and wellbeing offering. We offer amazing benefits that align with our values and culture at 15Five. Your Health & Wellbeing Medical, dental, vision with 15Five cost subsidy Employer paid Short-Term, Long-Term Disability, and Term LifeFamily planning support with enhanced medical plans and consultation programs Inclusive Benefits Stipend Access to mental health and wellness resources Your Life Flexible Time Off Program Generous paid leave for new parents Military leave Paid Company Holidays Sabbatical Program Your Future 401K with 4% Matching after 6 months Your Work Life Remote work Work with experts in leadership, culture, and personal development For more information see: Our Mission, Vision, & Values -https://www.15five.com/about Our People and Culture -https://www.15five.com/about/careers

15Five is the AI-powered performance management platform built for business impact. 15Five’s AI-powered all-in-one people management system is easy to use,
delivers effortless insights, and enables managers to lead with impact so that companies and their people can thrive. Within the flow of work, HR leaders are empowered with data-driven insights and recommendations while managers are transformed into change-makers, accelerating engagement, performance, and retention. 15Five combines generative AI, custom analytics, and human-centered principles within a complete platform, including 360° performance reviews, engagement surveys, goal tracking, manager coaching and training, and ongoing feedback tools like guided 1-on-1s and check-ins. A career at 15Five is the chance to have high impact in a fast paced, remote startup environment that operates with focus, urgency, and accountability. Every role and every hire meaningfully impacts our trajectory. We’re a high-performance, high-purpose team that gives you the chance to Build the Future of Work. We run on High Standards and High Support — holding a high bar for results, ownership, clarity, and disciplined execution, while investing in manager enablement, skill development, and whole-person care. We are committed to a No B.S. environment, meaning we anchor ourselves in truth, course-correct in real time, and expect people to lean into direct conversations. We are focused on ensuring every 15Fiver can Work in the Future and that starts with proactively using AI across all aspects of your role to increase leverage, speed, and impact. If you're energized by a fast pace, high standards, and high accountability for yourself and others, you'll thrive here and we encourage you to apply. Staff Data Scientist Role We take pride in our position as an innovator in the Human Resources landscape. This wouldn’t be possible without our outstanding team of engineers that apply next-generation thinking to our software - their abilities allow us to continually elevate the user experience and push leading performance-management technology into the global market. As an experienced Staff Data Scientist, you will play a critical role driving the discovery, creation, and integration of AL/ML models into our performance-management platform at 15Five. You will combine statistical methods with engineering best practices to help meet our business needs. We will rely on your statistical analysis skills, as well as insight for collecting, filtering, and preparing meaningful training data for AI/ML projects. You will be instrumental in modeling HR data and building rich structured context to power our knowledge base as well as AI agents engaging with our customers. You will work closely and collaborate with software and data engineers and guide them on operationalizing your work. You will be a self-starter, and build from the ground up leveraging your experience. Areas of Focus - Applied data science - Statistical analysis - Feature engineering - Supervised/Unsupervised model training & delivery Responsibilities - Data analysis and exploration: Conduct in-depth analysis of large structured and unstructured datasets to uncover patterns, insights, and signals that inform AI models, knowledge representations, and product decisions. - Statistical modeling: Develop and apply statistical methods to identify patterns, trends, and correlations in HR performance, engagement, and behavioral data, supporting evidence-based insights and model development. - Feature engineering and knowledge modeling: Design and engineer features from diverse data sources (e.g., reviews, surveys, behavioral signals, organizational data) to power machine learning models and construct structured AI context layers and knowledge representations used by intelligent systems and agents. - Training data development: Lead the creation and curation of high-quality labeled datasets, including annotation frameworks, evaluation datasets, and ground truth benchmarks that support model training and validation. - Machine learning model development: Design, develop, and train machine learning models (supervised, unsupervised, and representation-learning approaches) for use cases that enhance customer outcomes and enable intelligent product capabilities. - Context layer and AI system support: Develop data structures, embeddings, and context-enrichment pipelines that enable AI agents to retrieve relevant organizational knowledge, behavioral insights, and product context. - Model deployment and integration: Partner with engineering teams to operationalize models in production environments, ensuring scalability, reliability, and alignment with product architecture. - Model evaluation and iteration: Design evaluation frameworks and continuously monitor model performance, iterating on models, data pipelines, and features based on experimentation, feedback, and evolving business needs. - Cross-functional collaboration: Work closely with product, engineering, and design teams to translate business problems into data science solutions and ensure models deliver measurable value. - Documentation and knowledge sharing: Maintain clear documentation for datasets, modeling approaches, evaluation frameworks, and data pipelines to ensure reproducibility, transparency, and knowledge transfer across teams. - AI evaluation and benchmarking: Design evaluation datasets and benchmarking frameworks to measure AI agent performance, including retrieval quality, reasoning accuracy, and contextual relevance. - Data governance and responsible AI: Ensure that data used in models and AI systems meets privacy, security, and ethical standards, particularly when working with sensitive employee performance and engagement data. Required Experience/Competencies/Attributes - Education: BS or higher in Computer Science, Statistics, Mathematics, Physics, or a related quantitative field, or equivalent practical experience. - Industry experience: 7+ years of experience in data science, machine learning, or applied statistics in a production environment. - Statistical expertise: Strong foundation in statistical methods and the ability to apply them to large, complex datasets to identify patterns, trends, and actionable insights. - Machine learning experience: Demonstrated experience developing, evaluating, and deploying machine learning models that drive measurable business impact. Experience with large language models (LLMs), embeddings, or AI-driven systems is a strong plus. - Programming proficiency: Strong programming skills in Python and SQL, with experience building data processing pipelines, training models, and analyzing large datasets. - Data infrastructure experience: Experience working with modern data platforms including data warehouses, relational databases, and distributed data processing systems. - MLOps and production systems: Familiarity with MLOps practices and tools for model training, versioning, deployment, monitoring, and lifecycle management. - Software engineering practices: Understanding of modern software development workflows, including version control (Git), CI/CD pipelines, code review, testing practices, and agile development methodologies. - Communication and collaboration: Strong ability to communicate complex technical concepts to non-technical stakeholders and collaborate effectively with product, engineering, and cross-functional teams. Compensation & Benefits Annual Base Pay Range, US Full-Time Staff Data Scientist: $132,500 - $170,500/year Range may vary based on candidate's home location and proximity to different US compensation zones. This role's Total Rewards package includes participation in an annual discretionary company bonus program, equity awards, and comprehensive benefit and wellbeing offerings. We offer amazing benefits that align with our values and culture at 15Five. Your Health & Wellbeing Medical, dental, vision with 15Five cost subsidy Employer paid Short-Term, Long-Term Disability, and Term LifeFamily planning support with enhanced medical plans and consultation programs Inclusive Benefits Stipend Access to mental health and wellness resources Your Life Flexible Time Off Program Generous paid leave for new parents Military leave Paid Company Holidays Sabbatical Program Your Future 401K with 4% Matching after 6 months Your Work Life Remote work Work with experts in leadership, culture, and personal development For more information see: Our Mission, Vision, & Values -https://www.15five.com/about Our People and Culture -https://www.15five.com/about/careers

• Serve as the Technical Closer and Strategic Co-Pilot for 15Five’s revenue team, covering both Mid-Market and Enterprise segments. • Secure the "Tech Win" by validating complex requirements, navigating global HRIS integrations, and translating high-level HR philosophy into technical reality. • Embed yourself in the sales cycle as a revenue partner, adapting to various sales styles and elevating deal strategy. • Conduct high-stakes demos tailored to the audience, showcasing edge cases and bespoke workflows. • Serve as the authority on the HRIS ecosystem, building and scoping API/SFTP integrations live.

• Conduct in-depth analysis of large structured and unstructured datasets to uncover patterns, insights, and signals that inform AI models, knowledge representations, and product decisions. • Develop and apply statistical methods to identify patterns, trends, and correlations in HR performance, engagement, and behavioral data, supporting evidence-based insights and model development. • Design and engineer features from diverse data sources (e.g., reviews, surveys, behavioral signals, organizational data) to power machine learning models and construct structured AI context layers and knowledge representations used by intelligent systems and agents. • Lead the creation and curation of high-quality labeled datasets, including annotation frameworks, evaluation datasets, and ground truth benchmarks that support model training and validation. • Design, develop, and train machine learning models (supervised, unsupervised, and representation-learning approaches) for use cases that enhance customer outcomes and enable intelligent product capabilities. • Develop data structures, embeddings, and context-enrichment pipelines that enable AI agents to retrieve relevant organizational knowledge, behavioral insights, and product context. • Partner with engineering teams to operationalize models in production environments, ensuring scalability, reliability, and alignment with product architecture. • Design evaluation frameworks and continuously monitor model performance, iterating on models, data pipelines, and features based on experimentation, feedback, and evolving business needs. • Work closely with product, engineering, and design teams to translate business problems into data science solutions and ensure models deliver measurable value. • Maintain clear documentation for datasets, modeling approaches, evaluation frameworks, and data pipelines to ensure reproducibility, transparency, and knowledge transfer across teams. • Design evaluation datasets and benchmarking frameworks to measure AI agent performance, including retrieval quality, reasoning accuracy, and contextual relevance. • Ensure that data used in models and AI systems meets privacy, security, and ethical standards, particularly when working with sensitive employee performance and engagement data.

• Build and enhance the Data Intelligence Platform, including pipelines, tooling, and agentic infrastructure. • Partner with Data Scientists to develop AI platform capabilities, complex models, and agentic applications. • Own and improve existing autonomous agents; design, orchestrate, and deploy new ones across the product. • Implement best practices across software, data, and ML/AI engineering to strengthen our agentic ecosystem. • Build data models and pipelines that support the entire engineering organization. • Design scalable data platform features for ingestion, storage, validation, governance, monitoring, and ETL/reverse‑ETL. • Use AI‑assisted code generation effectively while ensuring code quality, security, and performance. • Review code and architecture, contribute to documentation, and elevate engineering standards. • Bring a product mindset to planning, helping shape vision, goals, and roadmap.

• Define and own the product vision for AI‑assisted performance and agentic workflows. • Build and execute a clear, outcome‑driven product strategy and roadmap. • Lead end‑to‑end product delivery across performance workflows, agentic systems, AI meeting assistance, and coaching. • Partner closely with Engineering and Design to deliver intuitive, low‑friction experiences. • Ensure alignment between core platform capabilities and in‑workflow AI surfaces across web, integrations, and agents. • Establish human‑in‑the‑loop safeguards, transparency, and trust in AI outputs. • Drive customer discovery through interviews, usability testing, and early‑adopter beta programs. • Translate insights into rapid iteration and continuous improvement. • Define and own product success metrics, including adoption, engagement, and impact. • Collaborate with GTM, Support, and Customer teams to ensure strong delivery and enablement. • Communicate product vision, roadmap, and progress to internal and external stakeholders.

• Lead the design vision for your product area and connect it to company goals. • Translate customer needs into clear flows, prototypes, and polished designs. • Use and evolve our Design System, identifying when patterns need to be extended or improved. • Partner with Product and Engineering to discover and solve customer problems. • Plan and run user research, synthesize insights, and influence roadmap decisions. • Communicate design decisions clearly across teams and give constructive feedback to peers. • Ensure visual and interaction quality across your product area and raise quality concerns proactively. • Contribute to improving design processes, tools, and team rituals. • Help foster an inclusive, collaborative design culture and champion design thinking across 15Five.