<p>Chief of Staff to the City Manager and Mayor</p> <p>Salary</p> <p>$75,382.08 - $91,627.44 Annually</p> <p>Location</p> <p>Oregon, OR</p> <p>Job Type</p> <p>Full Time</p> <p>Job Number</p> <p>2026-05-1078</p> <p>Department</p> <p>City Manager's Office</p> <p>Opening Date</p> <p>04/20/2026</p> <p>Closing Date</p> <p>5/10/2026 5:00 PM Pacific</p> <p>FLSA</p> <p>Non-Exempt</p> <p>Bargaining Unit</p> <p>MGMT CONF</p> <ul> <li>Description </li><li>Benefits </li></ul> <p>The Position</p> <p>The City of Lake Oswego is seeking a highly experienced, strategic, and detail-oriented Chief of Staff to provide executive-level support to both the City Manager and the Mayor. This role serves as a central hub for coordination, communication, and operational excellence-ensuring the seamless functioning of executive priorities, community engagement, and internal alignment. The Chief of Staff operates with a high degree of discretion, professionalism, and initiative, serving as a trusted advisor and integrator across departments, elected leadership, and the community. Duties include overseeing and driving strategic initiatives for the Council, Mayor and City Manager and communicating with the executive team. Work is generally of a critical, sensitive or confidential nature. The Chief of Staff to the City Manager and Mayor position is classified as a confidential employee.</p> <p>Key Responsibilities</p> <ul> <li>Serve as the main staff communication liaison with city leadership, elected and appointed officials, staff from other jurisdictions and agencies, city staff and the public. Manage difficult, demanding, or sensitive issues, topics, and communications in a timely, efficient and professional manner. </li><li>Establish and maintain productive and professional working relationships with elected officials, senior staffing government agencies, business executives, and community leaders in a highly complex and politically sensitive environment. Serve as the city's lead administrative representative in sensitive and confidential meetings and develop important communications on various topics. </li><li>Prepare agendas and schedule meetings for the City Manager and Mayor. Serve as the primary point of contact for visitors and meeting attendees. Exercise sound judgement in the coordination of complex calendars and politically sensitive relationships. Arrange meeting space, supplies and refreshments. </li><li>Prepare for city council meetings including coordinating for food and other preparation as needed. Provides office and administrative support to City Council such as answering questions and travel planning. Serve as backup to the City Recorder as needed. </li><li>Provide Executive Coordination and Scheduling. Manage complex calendars for both the City Manager and Mayor, including prioritization of competing demands and long-range planning. Coordinate internal and external meetings, ensuring alignment with strategic priorities. Anticipate scheduling conflicts and proactively resolve them. </li><li>Prepare briefing materials, agendas, and follow-up items for meetings and events. Coordinate documents requiring City Manager and Mayor signature in a timely, detailed, and confidential manner. Ensure proper processing of confidential and official materials and documents. Handling the City Manager and Mayor's correspondence by answering questions and directing internal projects alongside department heads. </li><li>Conduct research, prepare reports and presentations, respond to information requests, provide general analysis, and track multiple complex tasks and projects, often with competing deadlines. </li><li>Prepare and monitor budgets for the City Manager's Office, which may span multiple programs. Reconcile City Manager financial accounts, credit card statements and other accounts payable/receivable. Plan and coordinate travel logistics for the City Manager and Mayor, and Council including itineraries, lodging, and transportation. Prepare and process expense reimbursements in compliance with city policies. Maintain organized records of travel, expenses, and related documentation. </li><li>Assist in advancing key initiatives and special projects led by the City Manager and Mayor. Collaborating with the company's leadership team to prioritize strategies. Serve as a liaison between executive leadership and departments to ensure alignment and follow-through. Advises management on appropriate courses of action for resolution of problems within areas of expertise; analyzes problems, determines approach, compiles and analyzes data, and prepares reports/recommendations. </li><li>Support Mayor's civic outreach and programs. Support the Mayor in developing and executing civic engagement strategies and community outreach initiatives. Coordinate participation and briefings for regional boards, commissions, and community events. Assist in planning public-facing programs, forums, and partnerships that advance city priorities. Aid the Mayor and City Manager in building and maintaining relationships with community organizations, businesses, and regional partners. </li></ul> <p>Education and Experience Requirements</p> <p>A typical way of obtaining the knowledge, skills and abilities outlined above is to have obtained a Bachelor's degree in Public Political Science, Business Administration, or a related field, and five years in a related field or an equivalent combination of education and experience enabling the incumbent to perform the essential functions of the position. Master's degree is preferred.</p> <p>For a complete list of the essential duties, knowledge, skills and abilities required, and physical and mental demands please review the complete job description at www.ci.oswego.or.us/hr.</p> <p>Supplemental Information</p> <p>Compensation $75,012 - $91,627 / annually</p> <p>Non-cash compensation includes medical, dental, vision, PERS employee pick up, and VEBA contribution.</p> <p>Bilingual Pay: Employees who can speak and/or write a language listed in the top five (5) most common languages spoken in the Lake Oswego School District, may be eligible for three percent (3%) bilingual pay.</p> <p>Application Process: You may visit our web site at www.ci.oswego.or.us/jobs to access the online application process. Resumes will not be accepted in lieu of a completed job application. The City application must be submitted by: 5:00 P.M., May 10, 2026</p> <p>BENEFIT SUMMARY - managers, supervsors & confidential employees</p> <p>The City of Lake Oswego offers a wide range of benefits as part of your total compensation package. This summary is a general outline of the benefits that are available to regular status employees that are employed for 20 or more hours per week. Please contact Human Resources with any questions.</p> <p>Medical/Vision Insurance</p> <p>City of Lake Oswego offers 2 plan options for you and your dependents.</p> <ul> <li>CIS Regence Blue Cross Blue Shield Medical and VSP Vision-Traditional PPO </li></ul> <p>In-network and out-of-network coverage, no referral for specialist care.</p> <ul> <li>Kaiser Permanente Medical and Vision </li></ul> <p>Services provided exclusively by Kaiser providers through a primary care physician (PCP).</p> <p>Detailed benefit plan summaries for each plan is available upon request. The monthly employee cost for health insurance depends on the plan selected and if dependents are enrolled.</p> <p>Dental Insurance</p> <p>Comprehensive coverage through 2 plan options for you and your dependents.</p> <ul> <li>Delta Dental PPO-Moda Health Plan </li></ul> <p>In-network and out-of-network coverage, no referral for specialist care</p> <ul> <li>Kaiser Permanente Dental </li></ul> <p>Kaiser dentists agree to provide services to you at a discounted, negotiated fees and copays. Out-of-network services are not covered.</p> <p>With your choice, you will have access to a plan that includes preventive, routine and major dental care as well as orthodontic benefits for child dependents. There is no monthly cost to employee's for dental insurance.</p> <p>Life Insurance</p> <p>Standard Life Insurance Company</p> <p>City paid insurance amount of $50,000 for Basic Life and $50,000 Accidental Death and Dismemberment</p> <p>Supplemental life insurance coverage available for purchase for you, your spouse and dependents with guaranteed issue amounts (GI).</p> <p>Long Term Disability Insurance (LTD)</p> <p>Standard Life Insurance Company</p> <p>City paid long-term disability (LTD) insurance plan which guarantees that you will receive 60% of your salary, up to $6,000, following a 90-day waiting period.</p> <p>Survivors' Income Insurance</p> <p>Standard Life Insurance Company</p> <p>The City provides you with an insurance policy which gives your eligible survivors a monthly income after your death equal to a percentage of your insured earnings.</p> <p>Workers' Compensation Insurance</p> <p>SAIF Corporation</p> <p>You are provided workers' compensation insurance in accordance with Oregon Revised Statues.</p> <p>Public Employee Retirement System (PERS)</p> <p>Oregon Public Employees Retirement System (PERS)</p> <p>Benefits paid by PERS are funded from 2 sources:</p> <ul> <li>Member IAP contributions* paid on your behalf by the City (currently 6% of subject salary); and </li><li>Employer contributions* </li><li>contributions are made 6 months after employment (unless you are a previous or current member of PERS) and amounts are determined by PERS. </li></ul> <p>Vesting: Employee IAP Account - immediately, Pension Benefit Employer Contribution- 5 calendar years</p> <p>Employee Assistant Program (EAP)</p> <p>Canopy</p> <p>The EAP offers 5 confidential counseling and 24-hour crisis help to employees and their families at no cost. Other services include educational resources, legal assistance and financial help.</p> <p>Voluntary Employee Benefits Account (VEBA)</p> <p>HRA Veba</p> <p>City contributions* are made to a health reimbursement account to reimburse qualified medical, dental, and vision expenses and premiums you may incur on behalf of yourself, your spouse, dependents. The contribution amount is $100 per month.</p> <ul> <li>Contributions contributed monthly by the City or with leave transfer and/or cash-out funds. </li></ul> <p>Deferred Compensation Plan</p> <p>MissinSquare Retirement</p> <p>The City offers a 457(b) deferred compensation retirement plan. Contribution amounts can be specified as a percentage or dollar amount for pre-tax and/or Roth contributions. Eligibility is at hire and participation in this plan is voluntary.</p> <p>Flexible Spending Account (FSA)</p> <p>Allegiance</p> <p>Flexible Spending Accounts save you money by reducing the taxes you pay. Your FSA contributions are deducted from each paycheck before federal, FICA and, in most cases, state taxes are calculated. Use your FSA contributions to pay for eligible expenses incurred by you, your spouse, and your dependents.</p> <p>Holidays</p> <p>The following holidays are observed throughout the year:</p> <p>New Year's Day, Martin Luther King Birthday, President's Day, Juneteenth, Independence Day, Labor Day, Memorial Day, Veteran's Day, Thanksgiving Day and Day after Thanksgiving, Christmas Day, and one Personal Holiday.</p> <p>In some years, employees are also eligible for 4 hours holiday on Christmas Eve and 4 hours holiday on New Years' Eve.</p> <p>Managers and supervisors who do not receive overtime are eligible for management leave (32 to 40 hours per fiscal year depending on their pay grade).</p> <p>Vacation</p> <p>Employees shall accumulate vacation in the following manner:</p> <p>0-3 years:12 days (8 hours per month)</p> <p>4-9 years:16.5 days (11 hours per month)</p> <p>10-15 years:21.5 days (14.33 hours per month)</p> <p>16-19 years:23.5 days (15.66 hours per month)</p> <p>20+ years:25 days (16.67 hours per month)</p> <p>Part-time employee vacation hours are pro-rated based on hours worked. Vacation time may accumulate to maximum of 2 times yearly accrual. Excess vacation time will be transferred to employees VEBA account.</p> <p>Sick Leave</p> <p>At hire, 48 hours of sick time will be available. After a full 6 months of employment, sick hours will then be accrued a monthly basis at a rate of 8 hours per month.</p> <p>Part-time employee sick hours are pro-rated based on hours worked. Sick leave may be accumulated to 1080 hours. Anything over 1080 hours will be transferred to employees VEBA account.</p>