Director of AI & Automation
Visterra Landscape Group · Chicago, US
Job description
Director of AI & Automation
About Us:
The Visterra Landscape Group platform is ranked among North America's top 20 landscape service providers. Collectively, Visterra partner companies bring more than 200 years of expert landscape maintenance, enhancement, construction, sweeping, portering and critical winter services with a reputation for excellence in client service.
Incumbent partner leaders guide day-to-day operations with teams that value and prioritize safety, employee wellbeing and dynamic career pathways.
Visterra's partner companies include Outdoor Pride and Riverside Services in New Hampshire and Massachusetts; Dyna-Mist and Texas Landscape Group in Texas, Oklahoma, Louisiana, and Arkansas; Oberson's and GroundsPRO in Ohio and Kentucky; H&M Landscaping in Northeast Ohio; Land Corps in Tennessee; FullCare serving Missouri and the broader Midwest region; and Clover, serving Alabama.
Role Overview:
The Director of AI & Automation serves as a strategic and technical leader responsible for advancing Visterra Landscape Group’s automation, artificial intelligence, and process optimization initiatives. This role combines hands-on technical expertise with strategic leadership to design, implement, and scale intelligent solutions that enhance operational efficiency, improve service delivery, and support business growth across the organization.
Reporting to the Vice President of Technology, the Director of AI & Automation will partner closely with Operations, Finance, Sales, and other business leaders to identify opportunities for automation, develop scalable AI-driven solutions, and drive enterprise-wide adoption of emerging technologies.
Key Responsibilities:
- Develop and execute Visterra’s enterprise strategy for artificial intelligence, machine learning, workflow automation, and intelligent process improvement.
- Design, build, implement, and maintain AI-powered solutions, intelligent agents, and automated workflows that improve operational efficiency and eliminate manual processes.
- Architect scalable solutions utilizing Microsoft Power Platform technologies, including Power Automate, Power Apps, AI Builder, and emerging generative AI tools.
- Partner with business leaders to identify, prioritize, and deliver automation initiatives that improve productivity, reduce costs, and drive operational performance.
- Translate complex business challenges into technical requirements and develop innovative solutions that deliver measurable business outcomes.
- Develop and maintain integrations between automation platforms and core business systems, including Aspire, Acumatica, and other enterprise applications.
- Collaborate with Analytics and Reporting teams to leverage data assets, predictive modeling, and machine learning capabilities to support business decision-making.
- Design and implement predictive analytics solutions to identify trends, forecast outcomes, and provide actionable business insights.
- Establish governance frameworks, security standards, and best practices for AI and automation initiatives to ensure compliance, scalability, and data integrity.Monitor emerging technologies and industry trends to identify opportunities for innovation and competitive advantage.
- Serve as the primary advisor to executive leadership regarding AI, automation, and digital transformation strategies.
- Lead cross-functional projects and influence stakeholders across all levels of the organization to drive adoption of automation solutions.
- Mentor technical team members and promote a culture of innovation, continuous improvement, and technology adoption throughout the organization.
- Communicate complex technical concepts and analytical findings in a clear and actionable manner for business leaders and non-technical stakeholders.
- Support strategic technology initiatives and perform other duties as assigned.
Qualifications:
- Bachelor’s degree in Computer Science, Information Systems, Engineering, Data Science, or a related field required.
- Seven (7) or more years of progressive experience in automation, artificial intelligence, machine learning, enterprise systems engineering, software development, or related technology disciplines.
- Demonstrated experience designing and implementing enterprise automation solutions, AI-driven applications, and business process optimization initiatives.
- Extensive hands-on experience with Microsoft Power Platform technologies, including Power Automate, Power Apps, and AI Builder, strongly preferred.
- Strong proficiency in Python, SQL, API development and integration, and REST/JSON-based services.
- Experience integrating automation platforms with ERP, CRM, field service management, and other enterprise business systems.
- Proven ability to translate complex technical solutions into measurable business value and operational improvements.
- Experience within landscaping, field services, construction, facilities management, logistics, or other multi-location operational environments preferred.
- Strong analytical, project management, problem-solving, and organizational skills.
- Excellent communication and presentation skills, with the ability to effectively engage executive leadership and cross-functional stakeholders.
- Demonstrated ability to lead organizational change and drive adoption of new technologies across diverse business functions.
- Advanced degrees, AI certifications, Microsoft certifications, or other relevant technical credentials are preferred.
- Ability to travel up to 20% as needed to support branch operations, technology implementations, training initiatives, leadership meetings, and other business-related activities.
Benefits
Visterra offers a challenging and rewarding work environment where employees are encouraged to develop and grow as professionals. In this role, you will have the opportunity to lead an important operational function while contributing to the continued growth and success of the organization.
- Paid time off
- Health and wellness coverage
- 401(k) savings plan
- Professional development opportunities
The above description is intended to describe the general content, identify the essential functions, and set forth the requirements for the performance of this job. It is not to be construed as an exhaustive statement of duties, responsibilities, or requirements.
Visterra is an equal employment opportunity (EEO)/AA employer and strongly supports diversity in the workplace (m/f/d/v). We provide equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws.
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