HR Manager at Redwood Software – Ontario | Jobyssey

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 HR Manager for our Canada Center of Excellence, you will be the core People Lead for our growing Engineering team in Canada, building a vibrant, high-performing culture from the ground up. You will serve as a strategic HR partner with deep expertise in employee relations, talent development, leadership coaching, and Canadian employment standards. Using people data, AI, and automation, you will help leaders make informed talent decisions, streamline People practices, and connect local execution with Redwood’s global talent strategy.

Partner closely with R&D and Engineering leaders to align talent strategies with technical roadmaps, product goals, and organizational priorities.
Coach technical managers, from first-time managers through VPs, on difficult conversations, performance management, team dynamics, and building high-performing technical teams.
Champion a culture of “AI First,” helping Engineering leaders use automated tools and digital enablement to improve team workflows.
Use people data and organizational insights to identify trends, challenge assumptions, and support informed talent decisions.
Serve as the trusted, on-the-ground expert on the Ontario Employment Standards Act (ESA), human rights legislation, privacy law, and Canadian labour law, advising local leadership and supporting global colleagues on Canadian-specific requirements as needed.
Lead evidence-based, data-driven employee relations investigations and conflict resolution for the Canada team, and provide analytical support for global employee relations cases as needed.
Partner with the People Ops team to draft, update, and maintain Canada-specific HR policies, employee handbooks, and compliance standards aligned with local law and Redwood’s global values.
Act as an onsite leader in Canada, providing hands-on, day-to-day support to local leadership and employees.
Execute the end-to-end performance lifecycle within Engineering, including Talent Review cycles, development plans, promotions, and career planning.
Drive Performance Improvement Plans (PIPs) and remediation strategies where applicable, coaching managers on constructive feedback and clear performance metrics.
Collaborate with the Employee Experience Manager to analyze engagement surveys, stay interviews, attrition trends, and other people data, translating insights into meaningful actions.
Support organizational change and team effectiveness initiatives that strengthen performance, engagement, and retention.
Leverage AI tools, including LLMs and automated workflows, to streamline HR administration, improve talent management processes, and automate repetitive tasks.
Partner with Talent Acquisition and Employee Experience to create a smooth, high-touch onboarding experience for Canadian technical hires.
Collaborate with Total Rewards and Talent Acquisition to help ensure benefits, employer brand, and talent practices remain relevant and competitive for the Canadian workforce.

YOUR EXPERIENCE

5+ years of progressive HR experience with a strong focus on employee relations, manager coaching, and talent development.
Proven experience supporting R&D, Software Engineering, or Product teams in a high-growth SaaS environment, with an understanding of the pace, cadence, and nuances of engineering organizations.
Deep knowledge of Canadian and Ontario-specific employment standards, human rights codes, termination protocols, and workplace compliance requirements.
High emotional intelligence with demonstrated success coaching technical leaders through complex performance issues, difficult conversations, and team dynamics.
Strong judgment and the ability to balance employee experience, business needs, risk, consistency, and Redwood’s values when navigating sensitive decisions.
Strategic and analytical thinking, with the ability to use qualitative and quantitative data to identify patterns, diagnose organizational challenges, and recommend practical solutions.
Curiosity and fluency with AI and data tools, including tools such as ChatGPT, Claude, or Workday analytics, to improve productivity, synthesize data, and streamline workflows.
A global mindset and comfort working across geographies and time zones while translating global People programs into effective local practices.
Bachelor’s degree in HR, Business, or a related field.
CHRP/CHRL designation or specialized Canadian labour law training is considered a strong asset.

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.

If you like growth and working with happy, enthusiastic over-achievers, you'll enjoy your career with us!

THE LEGAL BIT
Redwood is an equal opportunity employer. Redwood prohibits unlawful discrimination based on race, colour, religion, sex, gender identity, marital or veteran status, age, national origin, ancestry, citizenship, physical or mental disability, medical condition, genetic information or characteristics (or those of a family member), sexual orientation, pregnancy or any other consideration made unlawful by regional or local laws. We also prohibit discrimination based on a perception that anyone has any of those characteristics or is associated with a person who has or is perceived as having any of those characteristics. All such discrimination is unlawful and will have a zero tolerance policy applied to it.

Redwood will comply with all local data protection laws, including GDPR when it comes to the handling and processing of personal data. Should you wish for us to remove your personal data from our recruitment database, please email us directly at [email protected]

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OUR MISSION

ABOUT US

CORE VALUES

YOUR IMPACT

YOUR EXPERIENCE