OUR MISSION
At Redwood, we empower our customers with lights-out automation for their mission-critical business processes.

ABOUT US
Redwood Software is the leader in full stack automation fabric solutions for mission-critical business processes. With the first SaaS-based composable automation platform specifically built for ERP, we believe in the transformative power of automation. Our unparalleled solutions empower you to orchestrate, manage and monitor your workflows across any application, service or server — in the cloud or on premises — with confidence and control.

Redwood’s global team of automation experts and customer success engineers provide solutions and world-class support designed to give you the freedom and time to imagine and define your future. Get out of the weeds and see the forest, with Redwood Software.

CORE VALUES
One Team. One Redwood
Make Your Own Weather
Obsess over Customer Success
Work the Problem
Be Curious
Own the Outcome
Respect Each Other

YOUR IMPACT
As an AI Developer you will be responsible for leading high-impact AI initiatives across SDLC innovation and product research, setting technical direction, designing and evaluating experiments, and delivering prototypes and insights that shape Redwood’s development practices and product strategy.

• Lead the design and execution of AI experiments across the software development lifecycle, including coding, testing, code review, documentation, and CI/CD processes
• Evaluate and recommend AI tooling and define scalable adoption patterns across development teams
• Establish frameworks to measure the impact of AI on developer productivity, code quality, and delivery velocity
• Identify inefficiencies in development processes and propose AI-driven solutions for pilot and scale
• Champion structured, disciplined AI experimentation and clear communication of findings
• Lead exploratory research into AI capabilities for Redwood’s enterprise automation platform, including agents, orchestration patterns, and AI-powered interfaces
• Own end-to-end development of complex prototypes, from feasibility assessment to working demonstrations
• Translate emerging AI trends into actionable opportunities aligned with Redwood’s products and strategy
• Collaborate with product management and engineering leadership to shape research direction and ensure outputs are production-ready
• Provide technical leadership through design reviews, knowledge sharing, and mentorship of junior team members

YOUR EXPERIENCE

• 8+ years of professional software development experience, including at least 3 years working with AI/ML systems or LLM-based applications
• Proven ability to lead complex, ambiguous technical initiatives and deliver clear, actionable outcomes
• Deep hands-on experience with modern AI development, including LLM APIs, prompt design, RAG architectures, agent frameworks, and evaluation methodologies
• Strong backend engineering skills across languages such as Python, Java, or similar, with the ability to adapt to new technologies as needed
• Experience integrating AI into software development workflows and measuring its impact on engineering outcomes
• Excellent written and verbal communication skills, with the ability to convey complex technical concepts to diverse audiences
• Demonstrated influence on technical direction beyond immediate team scope through leadership, proposals, or architectural contributions

Bonus Skills

• Experience with enterprise automation, ERP systems, or workflow orchestration platforms 
• Familiarity with Model Context Protocol (MCP) or similar frameworks for AI tool use 
• Background in developer experience, platform engineering, or SDLC tooling  
• Experience in research, applied science, or AI prototyping environments   

Pay Transparency: The typical base salary range for this position is 132,000 - 165,000 CAD annually. The range represents base salary only, and does not include company bonus, incentive for sales roles, equity or benefits, as applicable. Final compensation will be determined based on the candidate's skills, experience, and relevant qualifications.
Vacancy Status: Existing vacancy
AI Transparency Disclosure: As part of our commitment to hiring transparency and in compliance with Ontario law, please be advised that we utilize artificial intelligence (AI) tools during our interview process. Specifically, we may use an AI-enabled notetaking assistant to help capture and summarize interview discussions. This tool is used solely to assist our hiring team in summarizing candidate information; all final hiring and selection decisions are made exclusively by individuals on the hiring team.

OUR MISSION

At Redwood, we empower our customers with lights-out automation for their mission-critical business processes.

ABOUT US

Redwood Software is the leading orchestration platform for the autonomous enterprise, driving business transformation at the lowest total cost of ownership. Redwood empowers organizations to intelligently automate and orchestrate mission-critical business and IT processes across complex ERP, hybrid cloud, data and emerging agentic AI systems. Through its SaaS-first automation fabric—with AI embedded across the automation lifecycle—Redwood accelerates the path to autonomous operations. Backed by 30 years of experience and trusted by more than 50% of the Fortune 50, Redwood helps organizations unlock human potential to focus on innovation, growth and what’s next.

CORE VALUES

One Team. One Redwood

Make Your Own Weather

Obsess over Customer Success

Work the Problem

Be Curious

Own the Outcome

Respect Each Other

YOUR IMPACT

At Redwood, you’ll be working on the software that drives many of the world’s biggest companies. Our customers use our software for business critical workflows like month-end accounting processes and managing supply chain logistics. If you’re looking to have a real impact on people’s lives and on the global economy, this is your opportunity!

We are seeking a passionate entry level Full Stack Software Developer with a strong focus on Java to join our growing engineering team. In this role, you will be instrumental in designing, developing, and maintaining robust and scalable full-stack applications that power our automation and SaaS platforms. You will work across the entire software development lifecycle, from concept to deployment, collaborating closely with product managers, designers, and other engineers to deliver high-quality, impactful solutions.

• Build and ship highly performant and scalable full-stack applications using Java, JavaScript, and related modern technologies
• Develop and maintain robust back-end services, ensuring our APIs are efficient and reliable.
• Build responsive, intuitive front-end user interfaces that enhance the customer experience.
• Take ownership of small-medium sized features, collaborating with product management to translate requirements into technical designs
• Participate in all phases of the software development lifecycle from initial whiteboarding to production monitoring.
• Write clean, maintainable, and well-documented code following best practices.
• Implement and maintain automated tests (unit, integration, and end-to-end) to ensure code quality and reliability.
• Participate in troubleshooting of software defects and production issues and take proactive approach to improving system health
• Voice your perspective in technical discussions with architecture regarding topics like scalability, security, and performance.
• Advocate for modern tools and better ways of working to keep our engineering culture elite.
• Work with the larger R&D team to find ways to leverage AI tools for increased productivity and quality.

YOUR EXPERIENCE 

• Bachelor's degree in Computer Science, Software Engineering, or a related field (or equivalent practical experience).
• Proven ability to build with Java 11/17 or Spring Framework through internships or high-quality personal/school projects.
• Proficiency with front-end technologies such as HTML, CSS, JavaScript, TypeScript, and modern JavaScript frameworks (e.g., ReactJS, MobX).
• Experience with RESTful API design and development.
• Familiarity with cloud platforms (e.g., AWS, Azure, GCP) and containerization technologies (e.g., Docker, Kubernetes).
• Experience with unit testing and automation tools such as JUnit and Playwright.
• Practical knowledge of Unix environments, including command-line navigation, shell scripting (e.g., Bash), and basic log analysis for troubleshooting.
• Strong communication and interpersonal skills with a desire to contribute within a fast-paced high-performance team.. 

Preferred Skills and Qualifications:

• Experience with CI/CD pipelines and tools (e.g. Github actions, Jenkins, GitLab CI).
• Experience with relational databases (e.g., SQL, PostgreSQL, MySQL) and ORM frameworks (e.g., Hibernate, JPA). 
• Understanding of agile development methodologies (Scrum, Kanban)
• Familiarity with test-driven development (TDD) or behavior-driven development (BDD).Contributions to open-source projects or a strong GitHub portfolio.
• Familiarity with AI assisted development

Bonus Skills:

• Familiarity with other OS architectures Windows, Mac
• Experience building, maintaining, or integrating with app marketplaces

Pay Transparency: The typical base salary range for this position is 65,500 - 82,500 CAD annually. The range represents base salary only, and does not include company bonus, incentive for sales roles, equity or benefits, as applicable. Final compensation will be determined based on the candidate's skills, experience, and relevant qualifications.

Vacancy Status: Existing vacancy

AI Transparency Disclosure: As part of our commitment to hiring transparency and in compliance with Ontario law, please be advised that we utilize artificial intelligence (AI) tools during our interview process. Specifically, we may use an AI-enabled notetaking assistant to help capture and summarize interview discussions. This tool is used solely to assist our hiring team in summarizing candidate information; all final hiring and selection decisions are made exclusively by individuals on the hiring team.

Why Join Us?

• Competitive compensation package, comprehensive health, dental, and vision benefits.
• Opportunity to work on innovative and impactful products that are transforming industries.
• Career boosting learning opportunities with dedicated learning time and in-person collaboration and mentorship with other engineers.
• Work with a highly skilled, passionate, and diverse team of engineers.
• Opportunities for professional growth and development.
• Collaborative and supportive team environment.

OUR MISSION

At Redwood, we empower our customers with lights-out automation for their mission-critical business processes.

ABOUT US

Redwood Software is the leading orchestration platform for the autonomous enterprise, driving business transformation at the lowest total cost of ownership. Redwood empowers organizations to intelligently automate and orchestrate mission-critical business and IT processes across complex ERP, hybrid cloud, data and emerging agentic AI systems. Through its SaaS-first automation fabric—with AI embedded across the automation lifecycle—Redwood accelerates the path to autonomous operations. Backed by 30 years of experience and trusted by more than 50% of the Fortune 50, Redwood helps organizations unlock human potential to focus on innovation, growth and what’s next.

CORE VALUES

One Team. One Redwood

Make Your Own Weather

Obsess over Customer Success

Work the Problem

Be Curious

Own the Outcome

Respect Each Other

YOUR IMPACT

As UX Designer, you will own the end-to-end design of features and workflows for RunMyJobs, our enterprise automation platform. You'll collaborate with product managers, engineers, and customers to create intuitive experiences for complex automation workflows that empower finance and IT teams to orchestrate mission-critical business processes. You'll play a key role in building our design system from the ground up, establishing patterns and components that will scale across our product portfolio.

Product Design & Delivery

• End-to-end UX design for entire features and workflows within RunMyJobs

• Design intuitive interfaces for complex enterprise automation scenarios (job scheduling, workflow orchestration, monitoring)

• Create user flows, wireframes, prototypes, and high-fidelity designs that balance user needs with technical constraints

• Collaborate daily with product managers and engineers to ship high-quality experiences

• Participate in agile ceremonies and maintain design velocity alongside engineering sprints

• Conduct design QA and work with engineering to ensure implementation fidelity

User Research & Insights

• Plan and conduct user research activities (interviews, usability tests, observation sessions)

• Synthesize research findings into actionable insights and design recommendations

• Build empathy for enterprise users (finance teams, IT admins, automation engineers)

• Validate design decisions with real users and iterate based on feedback

• Partner with product management and customer success to understand user needs

Design System & Standards

• Contribute to building a new design system for Redwood's product portfolio

• Create reusable components, patterns, and guidelines that scale across features

• Consider existing design artifacts and evolve them into cohesive system

• Document design patterns and interaction standards

• Collaborate with engineers on component implementation and design tokens

• Advocate for design consistency and accessibility across products

Collaboration & Communication

• Present design work to cross-functional stakeholders and incorporate feedback

• Partner with product managers to define feature scope and success metrics

• Work closely with engineers to ensure designs are technically feasible

• Articulate design rationale and defend design decisions with data and user insights

• Leverage AI tools daily to accelerate design exploration, content generation, and workflow efficiency

YOUR EXPERIENCE

Required:

• 3-5 years of UX/product design experience, ideally in B2B SaaS or enterprise software

• Strong portfolio demonstrating full-stack UX capabilities (research, interaction design, visual design, prototyping)

• Experience designing for complex, data-dense enterprise applications

• Proficiency with Figma (primary tool) and modern design/prototyping tools

• Daily hands-on experience using AI tools (ChatGPT, Claude, Copilot, Midjourney, or similar) to enhance design productivity and workflows

• Demonstrated ability to balance user needs, business goals, and technical constraints

• Experience working in agile development environments alongside engineers

• Understanding of interaction design patterns, information architecture, and visual design principles

• Proven ability to conduct user research and translate insights into design solutions

• Experience contributing to or building design systems and component libraries

• Excellent communication and presentation skills

• Bachelor's degree in design, HCI, or related field (or equivalent experience)

Preferred:

• Experience designing automation, workflow, or developer tools

• Background in enterprise software domains (ERP, finance, IT operations, DevOps)

• Familiarity with accessibility standards (WCAG) and inclusive design practices

• Experience with front-end technologies (HTML, CSS, React) to collaborate effectively with engineers

• Experience using AI tools for design system work (component generation, design token automation)

• Track record of shipping complex features in cross-functional product teams

• Experience with user analytics and data-driven design decisions

• Contributions to open-source design systems or published design work

Pay Transparency: The typical base salary range for this position is CAD annually. The range represents base salary only, and does not include company bonus, incentive for sales roles, equity or benefits, as applicable. Final compensation will be determined based on the candidate's skills, experience, and relevant qualifications.

Vacancy Status: Existing vacancy

AI Transparency Disclosure: As part of our commitment to hiring transparency and in compliance with Ontario law, please be advised that we utilize artificial intelligence (AI) tools during our interview process. Specifically, we may use an AI-enabled notetaking assistant to help capture and summarize interview discussions. This tool is used solely to assist our hiring team in summarizing candidate information; all final hiring and selection decisions are made exclusively by individuals on the hiring team.

OUR MISSION

At Redwood, we empower our customers with lights-out automation for their mission-critical business processes.

ABOUT US

Redwood Software is the leader in full stack automation fabric solutions for mission-critical business processes. With the first SaaS-based composable automation platform specifically built for ERP, we believe in the transformative power of automation. Our unparalleled solutions empower you to orchestrate, manage and monitor your workflows across any application, service or server — in the cloud or on premises — with confidence and control. 

Redwood’s global team of automation experts and customer success engineers provide solutions and world-class support designed to give you the freedom and time to imagine and define your future. Our collaborative and dynamic environment fosters creativity, continuous learning, and a passion for building exceptional products. Get out of the weeds and see the forest, with Redwood Software.

CORE VALUES

One Team. One Redwood

Make Your Own Weather

Obsess over Customer Success

Work the Problem

Be Curious

Own the Outcome

Respect Each Other

YOUR IMPACT

We are seeking a highly skilled and passionate Full Stack Software Developer with a strong focus on Java to join our growing engineering team. In this role, you will be instrumental in designing, developing, and maintaining robust and scalable full-stack applications that power our automation and SaaS platforms. You will work across the entire software development lifecycle, from concept to deployment, collaborating closely with product managers, designers, and other engineers to deliver high-quality, impactful solutions.

• Design, develop, and implement highly performant and scalable full-stack applications using Java, Javascript,  and related technologies.
• Build and maintain robust back-end services, APIs, and microservices.
• Develop responsive and intuitive front-end user interfaces.
• Collaborate with product management to understand requirements and translate them into technical specifications.
• Participate in all phases of the software development lifecycle, including planning, design, coding, testing, deployment, maintenance, and assisting support.
• Write clean, maintainable, and well-documented code following best practices.
• Implement and maintain automated tests (unit, integration, and end-to-end) to ensure code quality and reliability.
• Troubleshoot, debug, and resolve software defects and production issues.
• Contribute to architectural discussions and decisions to ensure scalability, security, and performance.
• Stay up to date with emerging technologies and industry trends and advocate for their adoption where appropriate.
• Mentor less experienced developers and contribute to a culture of continuous learning and improvement

YOUR EXPERIENCE 

• Bachelor's degree in Computer Science, Software Engineering, or a related field (or equivalent practical experience).
• Professional experience as a Full Stack Software Developer, with a strong emphasis on Java (Java 11/17).
• Strong proficiency in Java and the Spring Framework (Spring Boot, Spring MVC, Spring Security).
• Experience with relational databases (e.g., SQL, PostgreSQL, MySQL) and ORM frameworks (e.g., Hibernate, JPA). 
• Solid understanding of front-end technologies such as HTML, CSS, JavaScript, TypeScript, and modern JavaScript frameworks (e.g., ReactJS, MobX).
• Experience with RESTful API design and development.
• Familiarity with cloud platforms (e.g., AWS, Azure, GCP) and containerization technologies (e.g., Docker, Kubernetes).
• Excellent problem-solving, analytical, and debugging skills. 
• Unit testing and automation tools such as JUnit and Playwright.
• Strong communication and interpersonal skills, with the ability to collaborate effectively in a team environment. 

Preferred Skills and Qualifications:

• Experience with message queues (e.g., Kafka, RabbitMQ).
• Knowledge of NoSQL databases (e.g., MongoDB, Cassandra).
• Experience with CI/CD pipelines and tools (e.g. Github actions, Jenkins, GitLab CI).
• Understanding of agile development methodologies (Scrum, Kanban)
• Familiarity with test-driven development (TDD) or behavior-driven development (BDD).
• Experience in the automation or SaaS industry.
• Contributions to open-source projects or a strong GitHub portfolio.

Bonus Skills:

•  SAP knowledge: ABAP, HANA
• OS knowledge: Windows, UNIX (Linux), Mac
• Relational databases (eg: H2, Postgres)
• Gradle
• Shell scripting
• Jest
• Tomcat
• AWS
• Experience with AI

Why Join Us?

• Competitive compensation package, comprehensive health, dental, and vision benefits.
• Opportunity to work on innovative and impactful products that are transforming industries.
• Generous paid time off, holidays and flexible work arrangements.
• Work with a highly skilled, passionate, and diverse team of engineers.
• Opportunities for professional growth and development.
• Collaborative and supportive team environment.
• “One Redwood” company culture.

OUR MISSION
At Redwood, we empower our customers with lights-out automation for their mission-critical business processes.

ABOUT US
Redwood Software is the leader in full stack automation fabric solutions for mission-critical business processes. With the first SaaS-based composable automation platform specifically built for ERP, we believe in the transformative power of automation. Our unparalleled solutions empower you to orchestrate, manage and monitor your workflows across any application, service or server — in the cloud or on premises — with confidence and control.

Redwood’s global team of automation experts and customer success engineers provide solutions and world-class support designed to give you the freedom and time to imagine and define your future. Get out of the weeds and see the forest, with Redwood Software.

CORE VALUES
One Team. One Redwood
Make Your Own Weather
Obsess over Customer Success
Work the Problem
Be Curious
Own the Outcome
Respect Each Other

YOUR IMPACT
As a Senior Full Stack Software Developer you will be responsible for leading the design, development, and delivery of scalable full-stack applications, shaping system architecture, and driving engineering excellence across Redwood’s automation and SaaS platforms.

• Design, develop, and implement scalable, secure, and high-performance full-stack applications using Java, JavaScript, and related technologies
• Architect and build backend services, APIs, and microservices with a focus on scalability, reliability, and maintainability
• Develop responsive, accessible, and high-quality front-end user experiences
• Partner with product managers and stakeholders to define technical strategy and translate business requirements into system designs
• Own and contribute across the full software development lifecycle, from architecture and design to deployment and optimization
• Establish and promote best practices in coding, testing, observability, performance optimization, and AI usage
• Lead architectural discussions and influence technical decisions for long-term scalability and performance
• Identify and resolve complex technical challenges, including production issues and system bottlenecks
• Champion automated testing strategies including unit, integration, and end-to-end testing
• Mentor and coach junior and mid-level developers, fostering a culture of engineering excellence
• Stay current with emerging technologies and drive adoption of innovative solutions

YOUR EXPERIENCE

• Bachelor’s degree in Computer Science, Software Engineering, or related field (or equivalent practical experience)
• 5+ years of professional experience in full stack development with strong expertise in Java (Java 11/17+)
• Deep proficiency in Java and experience designing distributed systems
• Strong experience building scalable APIs and microservices architectures
• Experience with front-end technologies including HTML, CSS, JavaScript/TypeScript, and frameworks such as React
• Experience with cloud platforms (AWS, Azure, or GCP) and containerization/orchestration tools such as Docker and Kubernetes
• Strong understanding of system design principles including scalability, resiliency, and security
• Proven ability to troubleshoot complex systems and implement long-term solutions
• Experience with automated testing frameworks (e.g., JUnit, Playwright) and quality engineering practices
• Strong communication and collaboration skills in agile environments
• Experience mentoring developers and contributing to team growth and technical direction

BONUS SKILLS

• Experience with event-driven architectures and message queues (e.g., Kafka, RabbitMQ)  
• Experience contributing to system architecture or technical strategy  
• Advanced knowledge of relational databases (e.g., PostgreSQL, MySQL) and ORM frameworks (Hibernate, JPA) 
• Experience designing and maintaining CI/CD pipelines (e.g., GitHub Actions, Jenkins, GitLab CI)  
• Understanding of agile methodologies and modern development practices (TDD/BDD)  
• Experience with application performance tuning and diagnostics at the OS level 
• Experience with the Spring ecosystem (Spring Boot, Spring MVC, Spring Security)  
• Experience in SaaS, enterprise software, or automation platforms  
• Contributions to open-source projects or strong GitHub portfolio  
• Experience building AI-integrated product architectures  
• Experience with app marketplaces or platform integrations  
• Experience decomposing monolithic applications into microservices  
• Experience integrating with SAP ABAP or HANA  
• Proficiency with shell scripting 
• Experience deploying and integrating with AWS  
• Familiarity with Windows and Mac OS environments  
• Familiarity with Gradle and Tomcat  

OUR MISSION

At Redwood, we empower our customers with lights-out automation for their mission-critical business processes.

ABOUT US

Redwood Software is the leader in full stack automation fabric solutions for mission-critical business processes. With the first SaaS-based composable automation platform specifically built for ERP, we believe in the transformative power of automation. Our solutions help thousands of organizations across 150 countries execute with speed and precision.

We pride ourselves on having an inclusive, supportive, coaching culture, giving you the opportunity to build lasting relationships with all our team members and senior leadership.

CORE VALUES

One Team. One Redwood

Make Your Own Weather

Obsess over Customer Success

Work the Problem

Be Curious

Own the Outcome

Respect Each Other

WORK ARRANGEMENT

This is a hybrid role based out of our leased Markham, Ontario office (target opening date: July 2026). In alignment with Redwood’s Canada In-Office Policy, the following schedule applies:

• Monday and Tuesday are mandatory in-office days for all GTA-based employees.

• Wednesday through Friday are flexible — work from the office or remotely based on team needs, project requirements, and personal preference.

• A monthly innovation and team-building day will be held in-office. 

• All GTA-based employees are required to be in-office for one full week (Monday–Friday) each fiscal quarter. Dates are communicated at least four weeks in advance.

Given the nature of this role — supporting multiple ELT members and serving as the operational anchor for the Markham office — additional in-office presence may be expected during leadership visits, executive offsites, and key planning periods. Flexibility to be on-site when it matters most is essential to success in this position.

YOUR IMPACT

As Redwood opens its first Canadian office in Markham, Ontario, this newly created role sits at the intersection of two critical functions: launching and running a best-in-class physical workspace, and providing high-impact executive support to 3-4 members of our Executive Leadership Team (ELT).

You will be the on-the-ground force that brings our Markham office to life — establishing culture, coordinating the day-to-day, and making sure local team members have everything they need to do their best work. Simultaneously, you will operate as a trusted executive partner, keeping senior leaders organized, on time, and focused on what matters most.

You will collaborate closely with two other EAs (based in Florida and Virginia) to ensure consistent, high-quality executive support, and you will report to the Chief of Staff to the CEO. This is a high-impact, high-trust role for someone who is deeply organized, proactive, and energized by variety.

Office Management (40% time)

• Support all activities related to the opening of our leased Markham office, including coordinating with vendors, building management, and IT to ensure readiness for a July 2026 launch — target headcount of 40–55 employees by end of year.

• Serve as the primary point of contact for all office-related matters — facilities, supplies, equipment, maintenance, and vendor relationships.

• Create a welcoming, functional, and well-organized work environment that reflects Redwood's culture and supports both on-site meetings and remote engagement.

• Plan and execute in-office employee engagement events, team meetings, all-hands gatherings, and culture moments that connect local employees to the broader global organization.

• Own office budgets, expense tracking, and invoice processing related to facilities and operational needs.

• Establish and maintain office policies, procedures, and safety protocols in compliance with local regulations and Redwood's global standards.

• Partner with IT, HR/People, and Finance to support seamless onboarding experiences for new hires based in or visiting the Markham office.

• Manage relationships with building management, security, cleaning services, and other local service providers.

• Act as a cultural ambassador — helping remote employees feel connected when they visit, and ensuring local employees feel part of One Redwood.

Executive Assistance (60% time) 

• Provide proactive, anticipatory calendar management for 3-4 ELT members, including one semi-local to the Greater Toronto Area and others based remotely. 

• Coordinate complex, multi-party meeting scheduling across time zones, balancing competing priorities with professionalism and good judgment.

• Manage end-to-end domestic and international travel arrangements including flights, accommodations, ground transportation, visa/entry requirements, and detailed travel itineraries.

• Own expense management — accurately processing and submitting expense reports and ensuring timely reconciliation for supported executives.

• Coordinate logistics for leadership offsites and cross-functional executive sessions — including room booking, A/V, catering, and materials.

• Maintain organized digital filing systems, shared drives, and reference documents for ELT members.

• Collaborate with the EA team in the US to share best practices, align on processes, and cover for one another as needed.

• Handle sensitive and confidential information with complete discretion and professionalism at all times.

YOUR EXPERIENCE

• 4+ years of combined experience in office management, executive assistance, or administrative operations, ideally within a fast-paced technology or SaaS environment.

• Bachelor’s degree in Business Administration, Communications, or a related field.

• Demonstrated experience managing complex, multi-stakeholder calendars and travel logistics across time zones.

• Proven ability to manage an office environment independently — from vendor relationships to facilities operations to employee engagement.

• Exceptional organizational skills with the ability to juggle multiple priorities, adapt to shifting demands, and maintain high-quality output under pressure.

• Strong written and verbal communication skills; comfortable drafting executive communications and interfacing with senior leaders.

• High degree of discretion and integrity when handling confidential information.

• Proficiency with modern productivity and collaboration tools including Google Workspace or Microsoft 365, Slack, Zoom, and expense management platforms. 

• Self-starter mindset with a bias for action — you don't wait to be asked, you anticipate needs and move forward with confidence.

• Comfortable operating in a global, remote-first organization where communication, autonomy, and clarity are critical.

Nice to Have

• Experience leveraging AI tools (e.g., ChatGPT, Claude, or similar) to automate repetitive tasks, streamline workflows, or surface insights. 

• Experience supporting C-suite or senior ELT executives in a global organization.

• Familiarity with Greenhouse, Workday, or similar HR/ATS platforms.

• Background in helping stand up or scale a new office location.

• Experience coordinating events, offsites, or company-wide meetings at scale.

WHY REDWOOD

This is a rare opportunity to put your fingerprints on something new. You will not be inheriting an established office — you will be building one. From day one, you will have a direct line to senior leadership, genuine ownership of your work, and the ability to shape how Redwood shows up in Canada.

We are a company that moves fast, values curiosity, and believes in giving people the autonomy to own their outcomes. If you thrive in environments where no two days are the same, where your contributions are visible, and where "it's not my job" is not in your vocabulary — you will find a home here.

Pay Transparency: The typical base salary range for this position is 87,175 - 99,875 CAD annually. The range represents base salary only, and does not include company bonus, incentive for sales roles, equity or benefits, as applicable. Final compensation will be determined based on the candidate's skills, experience, and relevant qualifications.

Vacancy Status: Existing vacancy

AI Transparency Disclosure: As part of our commitment to hiring transparency and in compliance with Ontario law, please be advised that we utilize artificial intelligence (AI) tools during our interview process. Specifically, we may use an AI-enabled notetaking assistant to help capture and summarize interview discussions. This tool is used solely to assist our hiring team in summarizing candidate information; all final hiring and selection decisions are made exclusively by individuals on the hiring team.

OUR MISSION

At Redwood, we empower our customers with lights-out automation for their mission-critical business processes.

ABOUT US

Redwood Software is the leader in full stack automation fabric solutions for mission-critical business processes. With the first SaaS-based composable automation platform specifically built for ERP, we believe in the transformative power of automation. Our unparalleled solutions empower you to orchestrate, manage and monitor your workflows across any application, service or server — in the cloud or on premises — with confidence and control. 

Redwood’s global team of automation experts and customer success engineers provide solutions and world-class support designed to give you the freedom and time to imagine and define your future. Get out of the weeds and see the forest, with Redwood Software.

CORE VALUES

One Team. One Redwood

Make Your Own Weather

Obsess over Customer Success

Work the Problem

Be Curious

Own the Outcome

Respect Each Other

YOUR IMPACT

As a People Business Partner (PBP) at Redwood, you won’t just advise the business — you’ll help redefine how work gets done. Operating at the intersection of AI curiosity and sharp business acumen, you’ll partner with senior leaders to build a forward-thinking talent strategy that outpaces the market. From algorithmic org design and AI-first enablement to precision talent management and data-driven employee relations, you’ll use advanced analytics and intelligent automation to elevate decision-making, accelerate performance, and shape a workforce built for the future.

Strategic Partnership

• Talent Strategy: Partner with the CFO and R&D leaders to develop people strategies that align with aggressive business goals.
• Org & Workforce Modeling: Use headcount modeling, span/layer analysis, and capacity forecasting to guide org design decisions.
• AI Literacy Advocacy: Champion a culture of "AI First," ensuring managers understand how to augment their teams with automated workflows, and build/utilize the tools available to them.

Precision Talent Management

• Intelligent Performance: Lead the performance lifecycle using data-driven insights to identify high-potential employees and succession risks.
• Upskilling for the AI Era: Facilitate development programs focused on AI literacy, prompt engineering, and digital fluency.
• Feedback Loops: Lead the analysis of Engagement Survey results, stay interview data, mobility, and various other data points to provide your client group with a holistic view of their org’s health.

Data-Driven Employee Relations & Ops

• Advisor: Serve as a trusted advisor, utilizing HR data to resolve complex issues with objective, evidence-based recommendations.
• Augmented Insights: Analyze HR data to identify hidden trends and provide "Next-Best-Action" insights to leadership.

AI in Action 

• Workflow Automation: You will "Work the Problem" by using AI to automate repetitive HR tasks (like initial ER documentation or policy FAQs) to free up time for high-value strategic coaching.
• Data Synthesis: You will use Large Language Models (LLMs) to synthesize massive amounts of qualitative feedback from surveys into concise executive summaries for the C-Suite.
• Content Generation: You will leverage AI to draft personalized development plans, job descriptions, and internal communications, ensuring they align with Redwood’s tone of voice.

YOUR EXPERIENCE

• Education: Bachelor’s degree in HR, Business, or a technical field.
• The "Future" Factor: Proven AI Curiosity; you are an early adopter of tools like ChatGPT, Claude, or Midjourney to enhance your personal productivity.
• Business-First Mindset: Experience supporting R&D and Finance departments where you were measured by business outcomes, not just HR metrics.
• Data Fluency: Advanced ability to collect, analyze, and present data to influence senior-level decisions.
• SaaS/Tech DNA: Experience in high-growth SaaS environments; you understand the "speed of software".

Pay Transparency: The typical base salary range for this position is CAD $93,000 - $117,000 annually. The range represents base salary only, and does not include company bonus, incentive for sales roles, equity or benefits, as applicable. Final compensation will be determined based on the candidate's skills, experience, and relevant qualifications.

Vacancy Status: Existing vacancy

AI Transparency Disclosure: As part of our commitment to hiring transparency and in compliance with Ontario law, please be advised that we utilize artificial intelligence (AI) tools during our interview process. Specifically, we may use an AI-enabled notetaking assistant to help capture and summarize interview discussions. This tool is used solely to assist our hiring team in summarizing candidate information; all final hiring and selection decisions are made exclusively by individuals on the hiring team.

Senior Product Manager

OUR MISSION

At Redwood, we empower our customers with lights-out automation for their mission-critical business processes.

CORE VALUES

• One Team. One Redwood
• Make Your Own Weather
• Obsess over Customer Success
• Work the Problem
• Be Curious
• Own the Outcome
• Respect Each Other

ABOUT US

Redwood Software is the leader in full stack automation fabric solutions for mission-critical business processes. With the first SaaS-based composable automation platform specifically built for ERP, we believe in the transformative power of automation. Our unparalleled solutions empower you to orchestrate, manage and monitor your workflows across any application, service or server — in the cloud or on premises — with confidence and control. 

Redwood’s global team of automation experts and customer success engineers provide solutions and world-class support designed to give you the freedom and time to imagine and define your future. Get out of the weeds and see the forest, with Redwood Softwar

As a Senior Product Manager, you will own a significant product area within RunMyJobs, Redwood’s enterprise SaaS automation platform. You will be accountable for delivering measurable business outcomes, directly influencing the roadmap, and driving strategic initiatives that position Redwood as the automation fabric for cloud and hybrid enterprises.

Your first assignment will be to define our path to automation on the hyperscalers, beginning with AWS and Azure. You will focus on automating core IaaS use cases that unlock the lift-and-shift market, enabling enterprises to migrate from on-premises to cloud with confidence. Over time, your assignments may evolve, giving you broad impact across Redwood’s platform.

Responsibilities

• Own the roadmap for strategic initiatives in RunMyJobs, starting with hyperscaler automation, ensuring alignment with Redwood’s long-term vision.
• Balance customer needs, technical feasibility, and business impact to deliver features that enable cloud migration at scale.
• Lead the end-to-end product lifecycle, from discovery to delivery, using customer input, market research, and data insights to drive decisions.
• Mentor junior PMs, modeling best practices in product craft and raising the bar for product excellence.
• Collaborate cross-functionally with engineering, sales, customer success, and marketing to resolve dependencies, ensure go-to-market readiness, and deliver customer value.
• Engage directly with customers and partners to validate use cases, shape priorities, and foster adoption.

Qualifications

• Bachelor’s degree or equivalent experience (advanced degree a plus).
• 5–7 years in product management, with a proven record of impactful delivery in enterprise software or cloud platforms.
• Strong analytical and strategic thinking skills; data-driven in setting priorities and measuring outcomes.
• Demonstrated ability to lead roadmap discussions with executives and influence across the organization.
• Domain knowledge in enterprise IT, workload automation, or cloud infrastructure (AWS/Azure) preferred