Lessen

DevOps Engineer

• Recommend alternate choices and trade-offs for various design decisions; investigate performance and process failures and work to improve them.
• Developing and build IT solutions, install and configure solutions, implement reusable components, translate technical requirements, and assist in all stages of the software development cycle.
• Stay apprised of new developments in both Azure and AWS cloud operations and help in determining architectural solutions to enhance the stability and performance of the infrastructure.
• Gain a deep application-level knowledge of the systems as well as contributing to their overall design.
• Work closely with other internal teams to build security, reliability, and scalability into the development lifecycle.
• Dive deep into the software stack to troubleshoot as needed and in resolving Windows and Linux operating system issues.
• Be on call as a part of rotating support schedule and respond to production issues and incidents in a timely manner.
• Build engineering automation and productivity tools to streamline and scale applications in the production environment.
• Build from the ground up reliable infrastructure services in AWS and Azure to deliver highly scalable services.
• Automate cloud operations using Infrastructure as Code tools and Configuration management tools.
• Ensures the confidentiality of internal and external data
• Performs ad-hoc projects and other duties as assigned

Senior DevOps Engineer

Marketing

• The Vice President of Marketing drives positioning of the Lessen brand to our current stakeholders (property owners, service professionals and partners) while creating, developing, and executing long term growth strategies to catapult our brand into the future. This role is an experienced and entrepreneurial B2B marketer that has worked directly with enterprise accounts. The Vice President of Marketing directs and manages all business-to-business marketing-related activities and partners closely with the sales organization. You should be a hands-on generalist highly skilled in a variety of marketing disciplines and capable of providing strategic vision.  Equally vital is your capacity to be business focused and deliberate about delivering tangible and impactful results.

Vice President of Marketing

Human Resources

·         Provide HR policy guidance, best practice interpretation, and thoughtful recommendations to managers and employees on a wide range of human resource matters.
·         Manage and continuously refine onboarding processes to ensure a smooth and positive new hire experience; oversee I-9 verification and compliance requirements.
·         Serve as a subject-matter resource in resolving complex employee leave and accommodation cases, collaborating closely with HR Business Partners, Talent Acquisition, Learning and Development, Benefits, Payroll, and Legal.
·         Administer and maintain accurate HR data in Workday, including organizational changes, promotions, compensation adjustments, and compliance-driven reporting.
·         Support the development, implementation, and ongoing improvement of HR policies, programs, and processes to enhance consistency and compliance.
·         Partner on workforce planning, organizational design, restructures, and succession planning activities in collaboration with HR leadership.
·         Analyze HR data and trends to provide insights and recommendations that support decision-making and business objectives.
·         Promote a positive and inclusive workplace culture through day-to-day support, coaching, and engagement initiatives.
·         Ensure strict confidentiality of employee information and adherence to federal, state, and local labor laws.
·         Participate in cross-functional initiatives and contribute to ad-hoc human resource projects that enhance efficiency and employee experience.

Senior HR Generalist

Operations

• Manage team to ensure that the core operational processes of vendor onboarding, vendor administration, and work order processing are properly followed; makes recommendations for substantive and procedural improvements
• Set clear goals and expectations for all regional team members; ensure accountability and consistency across the region
• Ensure the team meets daily operational expectations by tracking service delivery, ensuring client and vendor Service Level Agreements (SLAs) are met, reviewing call center production, evaluating work order completion timing – in-scope and out-of-scope, maintaining application compliance, and monitoring other department Key Performance Indicators (KPIs) and objectives
• Maintain accountability and ensure that performance trackers are accurate and updated, site additions/deletions are reconciled with vendor additions/deletions, financial credits are properly added to accounts, and event duplication reports and corrections are reviewed
• Manage, monitor and track vendor performance; implement strategies to meet or exceed targeted performance levels
• Thoroughly understand the scope and terms of each client’s contract within the region; communicates specifics to all regional team members and ensures the same for vendors
• Work closely with account team members to understand any contract/term changes for each client and inform regional team; communicate changes as appropriate
• Work closely with the Compliance team; ensure the organization, vendors and clients meet compliance standards
• Assist in client transition from Sales and Implementation to the Operations team
• Implement work order processes and procedures for initial proposal, pricing, standard formats, and approval for specific client in conjunction with other internal departments
• Provide operational feedback to the Account Operations team in a manner that allows them to effectively and proactively communicate to the client
• Work with Account Operations team to process non-contract client requests (out-of-scope/reactive/enhancement) and ensure work is scheduled and completed in a timely manner
• Communicate closely with the Account Management team and provide documentation for client meetings
• Work with department leadership to set the annual revenue budget and achieve the budgeted financial goals particular to the assigned region
• Collaborate with other internal departments in a manner that fosters teamwork and provide solutions to clients and vendors
• Ensure confidentiality of internal and external data
• Perform ad-hoc projects and other duties as assigned
• Travel requirements: Travel expected up to 10% of the time

Regional Operations Manager

Customer Success Manager

• Lessen is the tech-enabled, end-to-end property service provider that is transforming how commercial and residential real estate services are delivered and managed at scale.
• Lessen’s technology platform provides data-driven insights that unlock key growth opportunities for the entire real estate ecosystem—including investors, owners, managers, and service providers.
• The company leverages a network of over 30,000 vetted, qualified vendors (Lessen Affiliates) serving clients with over 1 million properties and completing more than 3.5 million work orders annually across an expanding range of services.
• Lessen, LLC is a venture-backed, privately held company with offices in Scottsdale and Chicago.
• Job Summary: The Customer Success Specialist plays a key role in driving successful onboarding, adoption and satisfaction among trade vendors using Lessen Pro, our SaaS Field Service Management (FSM) platform.
• This role serves as a trusted partner to new customers, guiding them through platform setup, training, and early adoption milestones.
• The specialist ensures a smooth onboarding experience, helping vendors quickly realize value from the platform and build confidence in its use.
• Key responsibilities include facilitating vendor activation, delivering training, addressing early-stage support needs, and monitoring engagement to proactively resolve issues.
• By building strong relationships and providing tailored support, the specialist improves vendor retention, reduces time to value, and contributes to the overall effectiveness of Lessen Pro.
• Reporting to the Manager of Customer Support, this role has a direct impact on customer satisfaction, platform utilization, and operational efficiency.

Customer Success Specialist

Account Manager

• The Client Relationship Manager is responsible for driving profitable business results and operational excellence by creating and developing strong, sustainable business relationships with their clients.
• Operates with some guidance.

Senior DevOps Engineer

Vice President of Marketing

Senior HR Generalist

Regional Operations Manager

Customer Success Specialist

Client Relationship Manager I