Leave of Absence Specialist Jobs
Leave of Absence Specialist jobs cover specializations in FMLA administration, ADA accommodation, and disability case management, hired across healthcare, insurance, financial services, and large employers in every sector, from entry-level coordinator roles to senior and program manager positions. Scan the live roles below and apply to whichever ones fit.
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Showing 5 of 26+ Leave of Absence Specialist jobs
IN ORDER FOR YOUR CANDIDACY TO BE CONSIDERED ALL APPLICANTS MUST APPLY BY FOLLOWING THE APPLICATION PROCESS INSTRUCTIONS LISTED IN THE JOB DISCRIPTION.
ALL JOB DESCRIPTIONS CAN ALSO BE FOUND ON THE OFFICE OF THE COMPTROLLER’S JOB OPPORTUNITIES PAGE LINKED BELOW.
https://careers.macomptroller.org/jobs/Careers
IF YOU APPLY THROUGH THE APPLY ONLINE LINK ON THIS MASSCAREERS PAGE YOU WILL NOT BE CONSIDERED FOR THIS POSITION.
OFFICE of the COMPTROLLER (CTR)
BEST Absence and Leave Management Lead
FY27 - 008
About the Office of the Comptroller
The Office of the Comptroller ensures that the more than $50 billion in annual transactions authorized by the general appropriations act and supplemental appropriations are executed in accordance with all statutory requirements and recorded in compliance with accounting standards. We also oversee capital assets, federal funding inflows, and other transactions. We also own and maintain statewide payments and payroll systems, safeguarding critical financial information. We operate in support of our partners, the financial staff at more than 150 departments and agencies across the Commonwealth.
As stewards of the public trust, we aspire to inspire confidence by maintaining our core principles: clarity, integrity, and accountability.
The powers and obligations of the Office of the Comptroller are generally dictated by M.G.L. c. 7A.
About Business Enterprise Systems Transformation (BEST) Program
The Commonwealth of Massachusetts is undertaking a multi-year project known as the Business Enterprise Systems Transformation (BEST) Program to implement a comprehensive Enterprise Resource Planning (ERP) software solution which will support a wide range of business functions used by all state agencies.
Phase 2 focuses on Payroll and Human Capital Management (HCM) modules which support a full software suite capable of addressing government business needs across Payroll, Time and Attendance, Performance Management, Payroll Management, Talent Acquisition, Onboarding and Offboarding Management, Position Management and Personnel Administration and Leave Management. Procurement has been completed and the Phase 2 project is well underway with a projected go-live date of April 2028. Accenture Consulting is the System Implementor and Workday is the SAAS software product vendor that we are working with.
The BEST Program is jointly sponsored by the Secretary for Administration and Finance, Comptroller of the Commonwealth and the Secretary of Technology Services and Security. This job posting is being issued through the Office of the Comptroller.
More information can be found at https://best.macomptroller.org.
BEST Absence and Leave Management Team Lead Summary
The BEST Absence and Leave Management Team Lead will provide functional leadership, guidance, and expertise in the design, configuration, testing, and implementation of the Workday Absence and Leave Management module as part of the Commonwealth’s Business Enterprise Systems Transformation (BEST) Program, enhancing existing capabilities and introducing new functionality for certain entities. This role will lead efforts to ensure the new solution meets the operational needs of Commonwealth agencies while aligning with state and federal regulations, Commonwealth policies and procedures, collective bargaining agreements, and other applicable requirements. The Lead will evaluate Workday's standard functionality and best practices to identify opportunities to modernize absence and leave management, improve business processes, and support the successful adoption of an integrated enterprise solution.
The BEST Absence and Leave Management Team Lead will collaborate with the BEST Program Management Office (PMO), system integrators, product vendors, agency representatives, subject matter experts, and other functional leads to coordinate absence and leave management business requirements, system configuration, and implementation activities. The role requires extensive knowledge of complex absence and leave management practices, including leave eligibility, accruals and carryover policies, leave balances, holiday calendars, work schedules, employee and manager self-service, approval workflows, and compliance with the Family and Medical Leave Act (FMLA), Massachusetts Paid Family and Medical Leave (PFML), and other applicable leave requirements. The Lead will guide configuration decisions, identify and address gaps between standard Workday functionality and Commonwealth requirements, and coordinate the development of solutions where necessary. Responsibilities also include supporting iterative system configuration, functional testing, user acceptance testing (UAT), data conversion and interface testing, issue resolution, and the development of reports and dashboards, while ensuring alignment and integration between Absence and Leave Management, Payroll, and other Workday functional areas.
The Absence and Leave Management Team Lead will play a key role in supporting organizational readiness, business process transformation, and the transition from existing absence and leave management processes and systems to the new Workday solution. Working closely with the Comptroller's Office, Human Resources Division (HRD), BEST Change Management and Training teams, and other Commonwealth stakeholders, the Lead will help identify significant business process changes, support the development of adoption strategies and training materials, and coordinate transition and deployment activities. The Lead will also facilitate knowledge sharing across functional teams, support discussions related to collective bargaining requirements and help ensure that absence and leave management configuration and process decisions align with the Commonwealth's broader enterprise objectives. Through these efforts, the Lead will contribute to a smooth transition and the successful implementation of an efficient, compliant, and sustainable absence and leave management solution.
Position Duration
This is a full-time, term-limited position established specifically to support Phase 2 of the Business Enterprise Systems Transformation (BEST) Program. The position is expected to continue through the designated implementation phase, including applicable deployment and stabilization activities. Employment is anticipated to conclude upon completion of the assigned program phase, subject to program timelines, operational needs, and applicable Commonwealth employment policies. This position is not intended to be a permanent, ongoing role.
Specific Duties
The specific duties of this position include but are not limited to the following:
- During Implementation, work with the PMO, fellow Functional Leads, system integration and product vendors, business owner and SMEs to analyze the proposed functional solution from a business perspective, as well as support the gathering of business requirements related to the implementation of the new functional modules in order to identify and realize the optimal future state solution.
- Lead the gathering of business requirements for configuration of the new software through facilitated meetings with SMEs, document analysis, requirements workshops and/or site visits and record options and recommendations using business process descriptions, use cases, scenarios and task and workflow Visio diagrams for both current-state (as is) processes and future-state (to be) processes.
- Establish themselves as the internal “product owner” of the Absence & Leave Functional Module Solution to include data collection and analysis, reviewing data conversion and data gathering needs in support of design and configuration, support business process and workflow gathering to then translate into business requirements and help lead all elements leading up to and through a successful deployment.
- Work collaboratively with the Comptroller’s Office, Human Resources Division (HRD) as well as other state government non-Executive branch departments to plan for the transition of existing functional solutions to the Enterprise Solution module, including transition timing, training, support in discussion with Collective Bargaining Unit representatives, and other activities needed to support a smooth transition.
- Establish themselves as the “go to” Absence/Leave subject matter expert and module solution liaison between the BEST Team the Solution Vendor and the state Agencies.
- Identify the organizational impact on skills, processes, structures, and business culture of their functional modules. Collaborate with change management program staff to plan for and develop communication, training, and readiness tasks and materials.
- Participate in the definition of strategies to address the gaps between the current and future state solution by leading the analysis of current business processes to detect critical deficiencies and essential new practices and procedures that will be needed to move from the current to the future state.
- Work with fellow Solution Functional Leads and system integration and product vendors to document and identify any solution functionality gaps for critical business needs, and work with the team (as well as agencies) on acceptable resolutions to these gaps.
- Oversee and provide guidance and direction to the Absence & Leave Functional Module Solution team on planning, design, configuration, testing and deployment tasks to ensure the quality and timeliness of deliverables and tasks are in line with the overall project implementation plan.
- Work with the BEST BI/Reports and Data Repository Team Lead to identify standard delivered reports related to the Workday Absence & Leave Functional Module Solution, how to configure those reports for use by the Commonwealth, identification and development of data warehouse queries and testing of reports, queries and dashboards as needed.
- Work with the BEST Data Integration Team and business partners to identify requirements for any interfaces to or from the new solution as they relate to the Workday Absence & Leave Functional Module Solution.
- Participate in the development of the Project Plan, Risk log, Issues Log, Change Control log, Status Reports and other project management office documentation and contribute to updates as needed.
- Participate in the project’s review of system integration and product vendor deliverables, as needed
- Work collaboratively and collectively with other program team leads and team members to help ensure program timeline, communications, agency support, testing, training plans and deliverables stay on track.
Salary Range: $120,000 - $155,000
This is a management position. The posted salary range is fixed and not subject to negotiation. The selected candidate will be offered a salary within this range, commensurate with their relative experience.
Comprehensive Benefits Package:
When you embark on a career with the Commonwealth, you are offered an outstanding suite of employee benefits that add to the overall value of your compensation package. We take pride in providing a work experience that supports you, your loved ones, and your future.
CTR is pleased to offer a comprehensive benefits package to its employees. The specific components and eligibility may vary based upon position classification, hours worked per week and other variables. Therefore, specific benefits for this position may be discussed as part of the interview and offer process.
This is a management position. The successful candidate will be an employee at will. This position is non-civil service and not covered by a collective bargaining agreement. This position is an exempt position.
The overall benefits available include paid vacation, sick and personal leave time, health, dental and vision insurance, and optional pre-tax Health Savings Account plans.
CTR employees also participate in the Commonwealth’s State Retirement Plan, which can become a defined benefit plan for those that both vest and subsequently retire from State service. Follow this link for additional retirement information: http://www.mass.gov/treasury/retirement/state-board-of-retire/
In addition, CTR provides employees the opportunity to elect life insurance, long term disability insurance, deferred compensation savings, tuition remission, pre-tax commuter account plans, along with other programs. This position may be eligible for the federal Public Service Loan Forgiveness (PSLF) program administered by the Federal Government.
CTR Hybrid-Work Model
CTR operates under a Hybrid work model. Under this policy, employees are currently required to work a minimum of four business days per month (two set by management and two set by the employee) on-site at CTR’s Boston office and may work remotely the remainder of the time at a location approved by their supervisor, so long as they comply with the requirements of the telework policy. Under this policy, all employees must be able to report to the Boston office with little or no notice, even including the same workday should an exigent circumstance arise. Therefore, a reasonable proximity to the office is necessary. CTR does not reimburse for employees to travel to the office.
On-site work is an essential function of this position.
In addition, the successful candidate may be required to work primarily on site in Boston during the initial training and orientation period and/or for certain positions a primarily on-site role may be necessary.
Commitment to Diversity:
CTR is committed to building a diverse staff at all levels across its entire agency.
The Commonwealth is an Equal Opportunity Employer and does not discriminate on the basis of race, religion, color, sex, gender identity or expression, sexual orientation, age, disability, national origin, veteran status, or any other basis covered by appropriate law.
CTR is an Equal Opportunity Employer. Females, minorities, veterans, and persons with disabilities are strongly encouraged to apply.
Application Process:
The Office of the Comptroller encourages interested candidates that meet the minimum entrance requirements and qualifications to apply for this position.
Interested candidates must submit their application, no later than 5:00 pm, on November 27, 2026 at https://careers.macomptroller.org/jobs/Careers.
Submissions should include the following:
- a cover letter; and
- resume.
Candidates chosen to advance to a second-round interview will also be required to submit:
- three business writing samples; and
- three professional references.
Late submissions may be considered solely at the discretion of CTR.
Required Background Check – Including Tax Compliance:
CTR requires a background check on all prospective employees as a condition of employment.
Candidates should know that the background check is not initiated until:
- A candidate is invited to a second or subsequent interview and
- The candidate has signed the Background Check Authorization Form and related releases.
This background check includes:
o a Criminal Offender Record Information (CORI) check,
o Commonwealth Department of Revenue state tax compliance.
Candidates with advanced degrees and professional licenses may have these credentials verified.
Individuals other than those references provided by a candidate may be contacted in the course of completing a full background and qualification check.
Further Information:
To learn more about the BEST Program, please visit the Program web site at: https://best.macomptroller.org.
Please visit https://www.macomptroller.org for more information about the Office of the Comptroller.
Qualifications
Preferred Qualifications:
Fully understand the Absence & Leave Management solution needs (i.e., workflows, business processes, etc.) of large-scale organizations and apply that understanding when reviewing configuration and design options offered in the new enterprise solution.
Experience with the design, deployment or administration of Workday solutions in public-sector organizations
Experience with all phases of testing including unit, system, integration, End-to-End and user acceptance testing.
Experience with Workday HCM and Payroll Enterprise Solution design, build, testing and deployment
Required Qualifications:
- At least 5 years of Absence & Leave Management-related experience with extensive knowledge of Absence & Leave Management systems and business practices in other large-scale organizations of similar size and complexity to the Commonwealth of Massachusetts.
- Experience and expertise in complex leave and absence management administration, policy and operations in either a public or private organization.
- Experience leading and conducting similar duties as defined above for an Absence & Leave Management solution of similar scope and complexity.
- Ability to facilitate understanding of existing and new functionality, identification and resolution for areas where business processes depart from the delivered software solutions and to recommend best practices from past experiences and deep knowledge of the potential solution.
- Superior analytical and technical skills.
- Excellent communication skills including written, verbal, presentation delivery and facilitation skills required to lead and facilitate meetings and working or planning sessions.
- Demonstrated experience in using computer-based tools including Visio, Microsoft Word, Excel, Power Point and Outlook.
Minimum Entrance Requirements:
Applicants must have at least (A) six (6) years of full-time or, equivalent part-time, professional, administrative, supervisory, or managerial experience in: Business administration, business management, public administration, public management, of which (B) at least two (2) years must have been in a supervisory or managerial capacity or (C) any equivalent combination of the required experience and substitutions below.
Substitutions:
I. A certificate in a relevant or related field may be substituted for one (1) year of the required (A) experience.
II. A Bachelor’s degree in a related field may be substituted for two (2) years of the required (A) experience.
III. A Graduate degree or higher in a related field may be substituted for three (3) years of the required (A) experience.
IV. A Doctorate degree in a related field may be substituted for four (4) years of the required (A) experience.
Primary Location
: United States-Massachusetts-Boston-1 Ashburton PlaceJob
: Human ResourcesAgency
: Off of the State ComptrollersSchedule
: Full-timeShift
: DayJob Posting
: Nov 13, 2026, 10:43:37 AMNumber of Openings
: 1Salary
: 120,000.00 - 155,000.00 YearlyIN ORDER FOR YOUR CANDIDACY TO BE CONSIDERED ALL APPLICANTS MUST APPLY BY FOLLOWING THE APPLICATION PROCESS INSTRUCTIONS LISTED IN THE JOB DISCRIPTION.
ALL JOB DESCRIPTIONS CAN ALSO BE FOUND ON THE OFFICE OF THE COMPTROLLER’S JOB OPPORTUNITIES PAGE LINKED BELOW.
https://careers.macomptroller.org/jobs/Careers
IF YOU APPLY THROUGH THE APPLY ONLINE LINK ON THIS MASSCAREERS PAGE YOU WILL NOT BE CONSIDERED FOR THIS POSITION.
OFFICE of the COMPTROLLER (CTR)
BEST Absence and Leave Management Lead
FY27 - 008
About the Office of the Comptroller
The Office of the Comptroller ensures that the more than $50 billion in annual transactions authorized by the general appropriations act and supplemental appropriations are executed in accordance with all statutory requirements and recorded in compliance with accounting standards. We also oversee capital assets, federal funding inflows, and other transactions. We also own and maintain statewide payments and payroll systems, safeguarding critical financial information. We operate in support of our partners, the financial staff at more than 150 departments and agencies across the Commonwealth.
As stewards of the public trust, we aspire to inspire confidence by maintaining our core principles: clarity, integrity, and accountability.
The powers and obligations of the Office of the Comptroller are generally dictated by M.G.L. c. 7A.
About Business Enterprise Systems Transformation (BEST) Program
The Commonwealth of Massachusetts is undertaking a multi-year project known as the Business Enterprise Systems Transformation (BEST) Program to implement a comprehensive Enterprise Resource Planning (ERP) software solution which will support a wide range of business functions used by all state agencies.
Phase 2 focuses on Payroll and Human Capital Management (HCM) modules which support a full software suite capable of addressing government business needs across Payroll, Time and Attendance, Performance Management, Payroll Management, Talent Acquisition, Onboarding and Offboarding Management, Position Management and Personnel Administration and Leave Management. Procurement has been completed and the Phase 2 project is well underway with a projected go-live date of April 2028. Accenture Consulting is the System Implementor and Workday is the SAAS software product vendor that we are working with.
The BEST Program is jointly sponsored by the Secretary for Administration and Finance, Comptroller of the Commonwealth and the Secretary of Technology Services and Security. This job posting is being issued through the Office of the Comptroller.
More information can be found at https://best.macomptroller.org.
BEST Absence and Leave Management Team Lead Summary
The BEST Absence and Leave Management Team Lead will provide functional leadership, guidance, and expertise in the design, configuration, testing, and implementation of the Workday Absence and Leave Management module as part of the Commonwealth’s Business Enterprise Systems Transformation (BEST) Program, enhancing existing capabilities and introducing new functionality for certain entities. This role will lead efforts to ensure the new solution meets the operational needs of Commonwealth agencies while aligning with state and federal regulations, Commonwealth policies and procedures, collective bargaining agreements, and other applicable requirements. The Lead will evaluate Workday's standard functionality and best practices to identify opportunities to modernize absence and leave management, improve business processes, and support the successful adoption of an integrated enterprise solution.
The BEST Absence and Leave Management Team Lead will collaborate with the BEST Program Management Office (PMO), system integrators, product vendors, agency representatives, subject matter experts, and other functional leads to coordinate absence and leave management business requirements, system configuration, and implementation activities. The role requires extensive knowledge of complex absence and leave management practices, including leave eligibility, accruals and carryover policies, leave balances, holiday calendars, work schedules, employee and manager self-service, approval workflows, and compliance with the Family and Medical Leave Act (FMLA), Massachusetts Paid Family and Medical Leave (PFML), and other applicable leave requirements. The Lead will guide configuration decisions, identify and address gaps between standard Workday functionality and Commonwealth requirements, and coordinate the development of solutions where necessary. Responsibilities also include supporting iterative system configuration, functional testing, user acceptance testing (UAT), data conversion and interface testing, issue resolution, and the development of reports and dashboards, while ensuring alignment and integration between Absence and Leave Management, Payroll, and other Workday functional areas.
The Absence and Leave Management Team Lead will play a key role in supporting organizational readiness, business process transformation, and the transition from existing absence and leave management processes and systems to the new Workday solution. Working closely with the Comptroller's Office, Human Resources Division (HRD), BEST Change Management and Training teams, and other Commonwealth stakeholders, the Lead will help identify significant business process changes, support the development of adoption strategies and training materials, and coordinate transition and deployment activities. The Lead will also facilitate knowledge sharing across functional teams, support discussions related to collective bargaining requirements and help ensure that absence and leave management configuration and process decisions align with the Commonwealth's broader enterprise objectives. Through these efforts, the Lead will contribute to a smooth transition and the successful implementation of an efficient, compliant, and sustainable absence and leave management solution.
Position Duration
This is a full-time, term-limited position established specifically to support Phase 2 of the Business Enterprise Systems Transformation (BEST) Program. The position is expected to continue through the designated implementation phase, including applicable deployment and stabilization activities. Employment is anticipated to conclude upon completion of the assigned program phase, subject to program timelines, operational needs, and applicable Commonwealth employment policies. This position is not intended to be a permanent, ongoing role.
Specific Duties
The specific duties of this position include but are not limited to the following:
- During Implementation, work with the PMO, fellow Functional Leads, system integration and product vendors, business owner and SMEs to analyze the proposed functional solution from a business perspective, as well as support the gathering of business requirements related to the implementation of the new functional modules in order to identify and realize the optimal future state solution.
- Lead the gathering of business requirements for configuration of the new software through facilitated meetings with SMEs, document analysis, requirements workshops and/or site visits and record options and recommendations using business process descriptions, use cases, scenarios and task and workflow Visio diagrams for both current-state (as is) processes and future-state (to be) processes.
- Establish themselves as the internal “product owner” of the Absence & Leave Functional Module Solution to include data collection and analysis, reviewing data conversion and data gathering needs in support of design and configuration, support business process and workflow gathering to then translate into business requirements and help lead all elements leading up to and through a successful deployment.
- Work collaboratively with the Comptroller’s Office, Human Resources Division (HRD) as well as other state government non-Executive branch departments to plan for the transition of existing functional solutions to the Enterprise Solution module, including transition timing, training, support in discussion with Collective Bargaining Unit representatives, and other activities needed to support a smooth transition.
- Establish themselves as the “go to” Absence/Leave subject matter expert and module solution liaison between the BEST Team the Solution Vendor and the state Agencies.
- Identify the organizational impact on skills, processes, structures, and business culture of their functional modules. Collaborate with change management program staff to plan for and develop communication, training, and readiness tasks and materials.
- Participate in the definition of strategies to address the gaps between the current and future state solution by leading the analysis of current business processes to detect critical deficiencies and essential new practices and procedures that will be needed to move from the current to the future state.
- Work with fellow Solution Functional Leads and system integration and product vendors to document and identify any solution functionality gaps for critical business needs, and work with the team (as well as agencies) on acceptable resolutions to these gaps.
- Oversee and provide guidance and direction to the Absence & Leave Functional Module Solution team on planning, design, configuration, testing and deployment tasks to ensure the quality and timeliness of deliverables and tasks are in line with the overall project implementation plan.
- Work with the BEST BI/Reports and Data Repository Team Lead to identify standard delivered reports related to the Workday Absence & Leave Functional Module Solution, how to configure those reports for use by the Commonwealth, identification and development of data warehouse queries and testing of reports, queries and dashboards as needed.
- Work with the BEST Data Integration Team and business partners to identify requirements for any interfaces to or from the new solution as they relate to the Workday Absence & Leave Functional Module Solution.
- Participate in the development of the Project Plan, Risk log, Issues Log, Change Control log, Status Reports and other project management office documentation and contribute to updates as needed.
- Participate in the project’s review of system integration and product vendor deliverables, as needed
- Work collaboratively and collectively with other program team leads and team members to help ensure program timeline, communications, agency support, testing, training plans and deliverables stay on track.
Salary Range: $120,000 - $155,000
This is a management position. The posted salary range is fixed and not subject to negotiation. The selected candidate will be offered a salary within this range, commensurate with their relative experience.
Comprehensive Benefits Package:
When you embark on a career with the Commonwealth, you are offered an outstanding suite of employee benefits that add to the overall value of your compensation package. We take pride in providing a work experience that supports you, your loved ones, and your future.
CTR is pleased to offer a comprehensive benefits package to its employees. The specific components and eligibility may vary based upon position classification, hours worked per week and other variables. Therefore, specific benefits for this position may be discussed as part of the interview and offer process.
This is a management position. The successful candidate will be an employee at will. This position is non-civil service and not covered by a collective bargaining agreement. This position is an exempt position.
The overall benefits available include paid vacation, sick and personal leave time, health, dental and vision insurance, and optional pre-tax Health Savings Account plans.
CTR employees also participate in the Commonwealth’s State Retirement Plan, which can become a defined benefit plan for those that both vest and subsequently retire from State service. Follow this link for additional retirement information: http://www.mass.gov/treasury/retirement/state-board-of-retire/
In addition, CTR provides employees the opportunity to elect life insurance, long term disability insurance, deferred compensation savings, tuition remission, pre-tax commuter account plans, along with other programs. This position may be eligible for the federal Public Service Loan Forgiveness (PSLF) program administered by the Federal Government.
CTR Hybrid-Work Model
CTR operates under a Hybrid work model. Under this policy, employees are currently required to work a minimum of four business days per month (two set by management and two set by the employee) on-site at CTR’s Boston office and may work remotely the remainder of the time at a location approved by their supervisor, so long as they comply with the requirements of the telework policy. Under this policy, all employees must be able to report to the Boston office with little or no notice, even including the same workday should an exigent circumstance arise. Therefore, a reasonable proximity to the office is necessary. CTR does not reimburse for employees to travel to the office.
On-site work is an essential function of this position.
In addition, the successful candidate may be required to work primarily on site in Boston during the initial training and orientation period and/or for certain positions a primarily on-site role may be necessary.
Commitment to Diversity:
CTR is committed to building a diverse staff at all levels across its entire agency.
The Commonwealth is an Equal Opportunity Employer and does not discriminate on the basis of race, religion, color, sex, gender identity or expression, sexual orientation, age, disability, national origin, veteran status, or any other basis covered by appropriate law.
CTR is an Equal Opportunity Employer. Females, minorities, veterans, and persons with disabilities are strongly encouraged to apply.
Application Process:
The Office of the Comptroller encourages interested candidates that meet the minimum entrance requirements and qualifications to apply for this position.
Interested candidates must submit their application, no later than 5:00 pm, on November 27, 2026 at https://careers.macomptroller.org/jobs/Careers.
Submissions should include the following:
- a cover letter; and
- resume.
Candidates chosen to advance to a second-round interview will also be required to submit:
- three business writing samples; and
- three professional references.
Late submissions may be considered solely at the discretion of CTR.
Required Background Check – Including Tax Compliance:
CTR requires a background check on all prospective employees as a condition of employment.
Candidates should know that the background check is not initiated until:
- A candidate is invited to a second or subsequent interview and
- The candidate has signed the Background Check Authorization Form and related releases.
This background check includes:
o a Criminal Offender Record Information (CORI) check,
o Commonwealth Department of Revenue state tax compliance.
Candidates with advanced degrees and professional licenses may have these credentials verified.
Individuals other than those references provided by a candidate may be contacted in the course of completing a full background and qualification check.
Further Information:
To learn more about the BEST Program, please visit the Program web site at: https://best.macomptroller.org.
Please visit https://www.macomptroller.org for more information about the Office of the Comptroller.
Qualifications
Preferred Qualifications:
Fully understand the Absence & Leave Management solution needs (i.e., workflows, business processes, etc.) of large-scale organizations and apply that understanding when reviewing configuration and design options offered in the new enterprise solution.
Experience with the design, deployment or administration of Workday solutions in public-sector organizations
Experience with all phases of testing including unit, system, integration, End-to-End and user acceptance testing.
Experience with Workday HCM and Payroll Enterprise Solution design, build, testing and deployment
Required Qualifications:
- At least 5 years of Absence & Leave Management-related experience with extensive knowledge of Absence & Leave Management systems and business practices in other large-scale organizations of similar size and complexity to the Commonwealth of Massachusetts.
- Experience and expertise in complex leave and absence management administration, policy and operations in either a public or private organization.
- Experience leading and conducting similar duties as defined above for an Absence & Leave Management solution of similar scope and complexity.
- Ability to facilitate understanding of existing and new functionality, identification and resolution for areas where business processes depart from the delivered software solutions and to recommend best practices from past experiences and deep knowledge of the potential solution.
- Superior analytical and technical skills.
- Excellent communication skills including written, verbal, presentation delivery and facilitation skills required to lead and facilitate meetings and working or planning sessions.
- Demonstrated experience in using computer-based tools including Visio, Microsoft Word, Excel, Power Point and Outlook.
Minimum Entrance Requirements:
Applicants must have at least (A) six (6) years of full-time or, equivalent part-time, professional, administrative, supervisory, or managerial experience in: Business administration, business management, public administration, public management, of which (B) at least two (2) years must have been in a supervisory or managerial capacity or (C) any equivalent combination of the required experience and substitutions below.
Substitutions:
I. A certificate in a relevant or related field may be substituted for one (1) year of the required (A) experience.
II. A Bachelor’s degree in a related field may be substituted for two (2) years of the required (A) experience.
III. A Graduate degree or higher in a related field may be substituted for three (3) years of the required (A) experience.
IV. A Doctorate degree in a related field may be substituted for four (4) years of the required (A) experience.
Primary Location
: United States-Massachusetts-Boston-1 Ashburton PlaceJob
: Human ResourcesAgency
: Off of the State ComptrollersSchedule
: Full-timeShift
: DayJob Posting
: Nov 13, 2026, 10:43:37 AMNumber of Openings
: 1Salary
: 120,000.00 - 155,000.00 YearlySee All 26 Leave of Absence Specialist Jobs
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Find JobsLeave of Absence Specialist Job Market
Who's Hiring
Top Industries Hiring
- Human Resources
What Employers Look For
The qualifications that appear most often in leave of absence specialist jobs.
- Three or more years of FMLA and ADA administration experience in a high-volume environment
- Working knowledge of federal and multi-state leave laws including CFRA, PFML, and USERRA
- Experience with leave management or case management platforms such as HR information systems
- Strong written communication skills for denial letters, approval notices, and employee correspondence
- PHR, SPHR, or CLMS certification preferred by many mid-size and enterprise employers
- Bachelor's degree in human resources, business administration, or a closely related field
Tips for Your Leave of Absence Specialist Job Search
Tailor your resume to compliance depth
Hiring managers for leave of absence roles look for specific regulatory fluency, so call out your hands-on experience with FMLA, ADA, USERRA, and state-specific leave laws by name. Vague references to 'HR compliance' won't hold up against candidates who list the actual statutes they've administered.
Highlight your case management volume
Employers want to know how many concurrent leave cases you've handled and how complex they were. Describe the caseload size and the mix of intermittent, continuous, and ADA accommodation cases you managed, so hiring teams can gauge whether your experience matches their program scale.
Apply early to roles that fit
Migrate Mate lists leave of absence specialist openings from across the United States in one place, so you can find roles that match and apply directly to each listing.
Target postings by program structure
Some employers run centralized leave programs through a third-party administrator, while others manage everything in-house. Read each job description carefully to understand which model the company uses, then frame your experience to match their setup in your cover letter.
Prepare scenario answers about difficult cases
Interviewers for leave of absence roles almost always ask how you handled a denied claim, a suspected FMLA abuse situation, or a conflict between state and federal leave entitlements. Have two or three specific, real examples ready that show your process, your documentation practice, and the outcome.
Negotiate around caseload and technology access
Before accepting an offer, ask directly about the case management system in use, the average caseload per specialist, and whether the team is growing. These factors affect your day-to-day workload far more than title, and knowing them upfront gives you real leverage in the negotiation.
Leave of Absence Specialist Jobs: Frequently Asked Questions
Which companies are hiring the most leave of absence specialists?
Hawthorn District 73, Sysco, and TikTok are hiring the most leave of absence specialists right now, with openings concentrated in Illinois, California, and Washington, based on current listings on Migrate Mate as of November 2026. Healthcare systems, national insurers, and large retail and financial services employers tend to post the highest volume of these roles year-round.
How many leave of absence specialist jobs are remote?
About 50% of leave of absence specialist openings are fully remote or hybrid as of November 2026, reflecting the administrative nature of most case management work. Fully remote positions are most common for roles focused on FMLA intake, documentation review, and third-party administrator coordination, while on-site or hybrid schedules are more typical for roles that involve direct employee interaction or HR business partner collaboration.
How do you become a leave of absence specialist?
Start by building a foundation in HR administration or benefits coordination, where you'll encounter leave requests as part of a broader workload. From there, focus on developing deep knowledge of FMLA, ADA, and your state's leave laws through on-the-job work and self-study. Earning a certification like the CLMS or PHR signals specialized competence to employers. Most specialists reach the role after two to four years in HR, though some move in from disability claims or benefits administration backgrounds.
Can I get a leave of absence specialist job with little experience?
Yes, some employers hire candidates with limited direct leave experience if you have a strong HR generalist or benefits background and can demonstrate familiarity with FMLA and ADA basics. Entry-level leave coordinator roles are the most accessible starting point. Focusing your applications on companies that use a third-party leave administrator is also useful, since those roles often involve case intake and tracking rather than independent legal interpretation, which lowers the experience bar.
What does the leave of absence specialist interview process look like?
Most employers run two to three rounds, starting with a phone screen from HR that covers your regulatory knowledge and caseload experience. A second interview with the hiring manager typically includes scenario-based questions about handling disputed claims, coordinating with payroll, or managing a complex ADA accommodation. Some employers add a written exercise or a panel interview with HR business partners. The process usually takes two to four weeks from first contact to offer.
Where can I find and apply to leave of absence specialist jobs?
You can find and apply to leave of absence specialist jobs on Migrate Mate, which lists current openings from employers across the United States. Search for roles that match your experience level, preferred work arrangement, and industry background, then apply directly to each listing that fits.
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