Lessen

Full-stack Engineer

• The Senior Software Developer supports the Product and Technology Department by managing day-to-day activities within the organization's software development function.
• Work as part of an agile development team building and working on enterprise grade software.
• Involved in all areas of development from design to development to testing.
• Oversee the work of a team responsible for designing, building, testing, deploying, maintaining, and supporting applications or systems software.
• Work to establish functional requirements and reviews solutions to ensure organizational needs are met.
• Select and oversee implementation of one or more software development methodologies.
• Develop short- and long-term product roadmaps to ensure continuous improvement of software.
• Document and demonstrate solutions by developing documentation, flowcharts, layouts, diagrams, charts, code comments and clear code.
• Prepare and install solutions by determining and designing system specifications, standards and programming.
• Improve operations by conducting system analysis, recommending changes in policies and procedures.

Senior Software Developer

Sales

• Drive new business growth: Consistently exceed annual quota through proactive pipeline generation, strategic prospecting, and disciplined territory planning.
• Execute a targeted go-to-market plan: Build and manage a pipeline, leveraging market insights, vertical data, and multi-channel outreach to grow new accounts.
• Position the Lessen value proposition: Articulate and demonstrate how Lessen’s AI-driven platform improves customer experience, streamlines facilities management, automates workflows, and reduces the cost to maintain distributed assets at scale.
• Advise on digital transformation: Partner with clients to integrate AI into their operational, maintenance, and business processes, helping to redesign corporate workflows that enhance service delivery, improve workforce efficiency, and increase customer satisfaction.
• Lead C-Suite engagements: Build trusted relationships with CFOs, COOs, CIOs, and Heads of Real Estate or Facilities to influence strategic decisions and advocate for AI-enabled process modernization.
• Orchestrate cross-functional sales motions: Collaborate with Solutions Consultants, Product, Account Management, Marketing, Operations, and Channel Alliances to manage a team-selling process.
• Negotiate and close complex deals: Lead multi-stakeholder negotiations that meet financial, legal, and ethical standards while delivering measurable ROI for clients.
• Integrate technology and trades: Demonstrate how Lessen unites technology, AI, data intelligence, and field expertise across HVAC, electrical, plumbing, janitorial, and general maintenance trades to streamline service delivery at scale.
• Forecast with precision: Maintain CRM hygiene, ensuring pipeline accuracy and forecasting predictability.
• Represent Lessen externally: Participate in industry associations, conferences, and client forums to expand market presence and establish thought leadership.
• Travel: Up to 50% domestic travel for prospect meetings, industry events, and strategic presentations.

Enterprise Sales Director

Designer

• Collaborates with stakeholders to understand needs and expectations and uncover organizational and performance goals.
• Be an active listener who also knows how to ask insightful questions to unlock a greater understanding of business and learning needs.
• Applies a systematic process to gather, identify, and analyze root causes of learning and performance gaps.
• Makes informed, learning science backed, recommendations for performance improvement solutions to address root causes in partnership with manager or Senior LXD.
• Works with subject matter experts and other resources to transform knowledge into learning solutions.
• Consults with stakeholders to gain commitment for implementing solutions.
• Comfortably use quantitative and qualitative needs analysis techniques to help prioritize our learning efforts.
• Assesses and evaluates emerging learning technologies for adoption and integration.
• Confidently lead business and user research to identify pain points and opportunities to drive behavior change and performance improvement.
• Serves as leader in design, development and testing, of new and existing learning initiatives; innovates enhancements to existing learning modules which may include applications over multiple software and platforms.
• Responsible for large-scale curriculum design and course mapping.
• Creates and manages a detailed project plan to ensure quality standards and timelines for deliverables are met.
• Utilizes needs analysis to address learning and performance gaps.
• Properly scope and define outcome-driven learning objectives.
• Identifies and selects the appropriate approaches and technologies that follow sound principles of learning theory and align to the specific learning/performance support opportunity.
• Designs logical learning assets that create an effective, efficient and engaging experience for the learner and maximize performance improvement outcomes that yield measurable organizational results.
• Designs and develops instructional materials including job aids, e-learning content, videos, PowerPoint presentations and more with minimal supervision required.
• Write concise and customer-friendly instruction for a variety of learning modalities (e.g., online courses, documentation, resources, in-app messages)
• Conducts reviews of materials with appropriate parties, such as subject matter experts, the design team, and the target audience.
• Proactively collects and incorporates feedback from leaders and stakeholders.
• Builds into the design of learning solutions a variety of both formative and summative evaluation strategies to determine learning mastery and impact.
• Effectively organize content and deliverables in a logical and intuitive manner.
• Regularly QA test and debug learning content.
• Able to prioritize work based on business needs and pivot when organizational needs require it.
• Experiment and use diverse technologies to create interactive, responsive, and user-friendly online courses.
• Continuously evaluates, reports on, and improves existing learning/performance support solutions.
• Under the guidance of the LXD Manager, provide leadership to LX training team in terms of identifying resourcing, coaching and work planning
• Under the guidance of the LXD Manager, provide guidance and constructive feedback to LX team
• Ensure a collaborative relationship between LX designers and Departments to ensure the design and timing meet requirements
• Challenge and support the LX team
• Effective and clear communication with LX team
• Foster a positive team environment

Senior Learning Experience Designer

• Collaborates with stakeholders to understand needs and expectations and uncover organizational and performance goals.
• Be an active listener who also knows how to ask insightful questions to unlock a greater understanding of business and learning needs.
• Applies a systematic process to gather, identify, and analyze root causes of learning and performance gaps.
• Makes informed, learning science backed, recommendations for performance improvement solutions to address root causes in partnership with manager or Senior LXD.
• Works with subject matter experts and other resources to transform knowledge into learning solutions.
• Consults with stakeholders to gain commitment for implementing solutions.
• Comfortably use quantitative and qualitative needs analysis techniques to help prioritize our learning efforts.
• Assesses and evaluates emerging learning technologies for adoption and integration.
• Confidently lead business and user research to identify pain points and opportunities to drive behavior change and performance improvement.
• Serves as leader in design, development and testing, of new and existing learning initiatives; innovates enhancements to existing learning modules which may include applications over multiple software and platforms.
• Responsible for large-scale curriculum design and course mapping.
• Serves as Team Lead on collaborative projects.
• Creates and manages a detailed project plan to ensure quality standards and timelines for deliverables are met.
• Utilizes needs analysis to address learning and performance gaps.
• Properly scope and define outcome-driven learning objectives.
• Identifies and selects the appropriate approaches and technologies that follow sound principles of learning theory and align to the specific learning/performance support opportunity.
• Designs logical learning assets that create an effective, efficient and engaging experience for the learner and maximize performance improvement outcomes that yield measurable organizational results.
• Designs and develops instructional materials including job aids, e-learning content, videos, PowerPoint presentations and more with minimal supervision required.
• Write concise and customer-friendly instruction for a variety of learning modalities (e.g., online courses, documentation, resources, in-app messages).
• Conducts reviews of materials with appropriate parties, such as subject matter experts, the design team, and the target audience.
• Proactively collects and incorporates feedback from leaders and stakeholders.
• Builds into the design of learning solutions a variety of both formative and summative evaluation strategies to determine learning mastery and impact.
• Effectively organize content and deliverables in a logical and intuitive manner.
• Regularly QA test and debug learning content.
• Able to prioritize work based on business needs and pivot when organizational needs require it.
• Experiment and use diverse technologies to create interactive, responsive, and user-friendly online courses.
• Continuously evaluates, reports on, and improves existing learning/performance support solutions.
• Under the guidance of the LXD Manager, provide leadership to LX training team in terms of identifying resourcing, coaching and work planning.
• Under the guidance of the LXD Manager, provide guidance and constructive feedback to LX team.
• Ensure a collaborative relationship between LX designers and Departments to ensure the design and timing meet requirements.
• Challenge and support the LX team.
• Effective and clear communication with LX team.
• Foster a positive team environment.

Business Analyst

• Partner with leadership to develop a strategic vision for the department; takes a proactive approach to influencing business strategy through data findings and establishing meaningful and easy-to-consume reporting that informs teams within the department
• Proactively identify voids in reporting and analytics for the respective department and design solutions for the problem
• Take high-level instruction from leadership with minimal supervision and delivers insightful work products
• Design new projects/programs by analyzing client requirements
• Generate departmental business intelligence, data management, reporting and analytics
• Gather data to help compose monthly reviews of the operational and financial performance of the division.
• Improve processes for the creation and/or distribution of existing reporting
• Assess current practices, collects information, and analyzes trends to drive efficiencies
• Assess financial and operational performance; identifies areas of improvement and develop solutions to help the department grow and become more efficient
• Maintain operational reports allowing leaders to analyze the performance of individual members of their team; identifies trends and works to prevent client escalations
• Organize, analyze, interpret, and report on large amounts of raw data with the ability to extract relevant conclusions and trends; presents the results to the senior leadership team
• Develop operational and financial performance tracking dashboards in Tableau
• Foster a positive team environment
• Require general coaching and supervision
• Ensure confidentiality of internal and external data
• Perform ad-hoc projects and other duties as assigned

Senior Business Analyst

Customer Support

• Develop and maintain positive client relations required to ensure superior client satisfaction
• Receive and handle customer calls and email requests for services
• Manage the scheduling and completion of all services assigned by customers; many of the services a Customer Service Representative will handle will be complex project type work {examples: closed stores or restaurants with multiple Affiliates involved}
• Act as final escalation point before determining whether any disputes or un-satisfied service confirmations need to be highlighted to Team Lead
• Maintain open communication with affiliates in a manner that adheres to all contracts and agreed upon Scope of Work throughout the duration of the relationship
• Provide information to supervisors, co-workers, and subordinates by telephone, in written form, email, or in person; will be considered a point person for the handoff between shifts and/or other offices
• May be required to run special reports for the Team Lead and/or Client, as well as provide analysis on performance trends
• Demonstrate professionalism in communication, relationship development, customer service, etc.
• Assist in training team members and provides constructive feedback as necessary
• Provide market intelligence feedback to maximize customer satisfaction and to ensure strategies and policies are in place to attract and retain customers
• Shift flexibility may be required
• Foster a positive team environment
• Ensure confidentiality and accuracy of internal and external data
• Perform ad-hoc projects and other duties as assigned

Customer Service Representative, Weekends

Operations

• Improve the delivery of services to the client by observing and reporting on performance and experience from an on-site-user perspective, both customer and vendor
• Provide the Operations team with local insight regarding the unique needs of customers in the assigned market and the nuances of doing business with local vendors
• Represent SMS in matters related to Fire/Life Safety, Environmental Health and Safety, and Disaster Recovery to mitigate the cost of unnecessarily expansive scopes of work
• Provide administrative support for matters requiring in-person representation, such as dealing with municipal offices and being present for code inspections
• Assure client leadership that SMS is effectively resolving all facilities issues through local engagement on high priority issues, prior to client escalation
• Enhance the effectiveness of SMS technology solutions through increased adoption by directly demonstrating the platform’s value to both customer and vendor
• Build and maintain professional relationships with clients to gain an understanding of their operational needs; assist in the development and implementation of solutions to meet those needs
• Proactively manage delivery of services to sites without permanent client employees such as vacant sites and off-premise ATM locations
• Maintain cognizance of work being done by third party vendors at client sites such as new build construction projects, branch decommissionings, or other projects falling outside the SMS scope of work; represent SMS in the acceptance of such projects into the Facilities portfolio
• Perform non-maintenance tasks related to facilities management as approved by the Director of Operations
• Demonstrate SMS’s commitment to consistent high-quality service through scheduled and unscheduled quality assurance visits
• In coordination with the Affiliate Relationship Management team, develop business relationships with vendors to achieve seamless, high-quality service and advantageous pricing
• Communicate findings and recommendations based on client data clearly; couple insights with actionable conclusions to drive business decisions
• Facilitate the flow of information among customers and affiliates in the field and the SMS Operations team
• Foster a positive team environment and may provide coaching or mentoring to team members
• Ensures confidentiality and accuracy of internal and external data
• Performs ad-hoc projects and other duties as assigned
• This position is remote and requires up to 60% travel within the assigned geographic area of responsibility

Field Operations Manager

Account Manager

• The schedule for this role is Monday - Friday, 10:00 AM - 7:00 PM CDT.
• Serve as primary client account manager for assigned client portfolio, interacting regularly with client management telephonically, electronically, and in person to ensure the highest level of client satisfaction
• Evaluate all client requests for urgency, efficacy, and necessity to ensure that the client’s maintenance budget is allocated efficiently so as to satisfy service requirements while controlling discretionary scope expansion and preventing unnecessary spending
• Manage all service requests by understanding the issue in context, assigning the appropriate resources for project completion, maintaining appropriate timelines, and communicating regularly with client and department leadership
• Control the release of work requests to vendors to achieve monthly, quarterly, and annual financial objectives for the client and Lessen.
• Anticipate, take ownership of, and proactively manage client escalations in order to achieve resolution as quickly as possible, while escalating the most complex and consequential issues to department leadership with actionable recommendations for solutions
• Developing and manage relationship with various client stakeholders including service location staff and their management, corporate functions, and the management offices for facilities-related programs and projects
• Coordinate with and appropriately direct workflows among the client’s internal commodities and external service providers to ensure work is completed and accounted for per the client’s specifications
• Prepare and deliver routine and ad hoc communications and qualitative reports to the client that are impactful and of high professional standards
• Proactively research, develop, and implement solutions to client requests that fall outside of standard procedure and historical precedent and are ambiguous in context, scope, and resolution process
• Coordination with external third-party stakeholders including municipal governments, landlords, property associations, and other third-party vendors to resolve all facilities-related issues
• Ensure full utilization of warranty provisions (both equipment and service) and evaluate lease terms to ensure that client funds are not spent on repairs for which another party is liable
• Coordinate with and provide direction to after-hours and weekend coverage teams to maintain 24/7 coverage of all client support activities
• Fosters a positive team environment and may provide coaching or mentoring to team members
• Ensures confidentiality and accuracy of internal and external data
• Performs ad-hoc projects and other duties as assigned
• Travel required up to 25%

Account Representative

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

• 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

• 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.

Client Relationship Manager I

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.