Director of Operations

Season Investments is a wealth management firm delivering financial planning and investment management to a select high-net-worth clientele. We believe wealth should be a tool for freedom rather than a source of stress, and our work is centered on long-term relationships built on trust, sound advice, and sophisticated investment management. We help clients remove uncertainty from their financial lives so they can focus their time and energy on what makes their life truly rich.

Make your application after reading the following skill and qualification requirements for this position.
This role is a critical part of delivering on our mission. As a small and growing firm, we rely on a highly capable, self-sufficient professional to own a complex operational workload and keep the business running accurately and on schedule. This position handles sensitive financial information, client assets, regulatory obligations, and interconnected systems where accuracy, confidentiality, and sound judgment are a must. Success requires critical thinking, comfort interpreting detailed data and numbers, and the ability to organize large quantities of information without losing sight of broader priorities.
To apply, submit resume and cover letter explaining what you find interesting about the role and why you think you might be the right fit to
Role Description
This position supports the firm's Principals and touches nearly every part of the business. It blends recurring processes with open-ended projects requiring initiative, independent problem solving, and thoughtful coordination.
Regulatory ComplianceAdminister the compliance program and develop towards becoming the firm’s Chief Compliance OfficerMaintain examination-ready records and coordinate filings, client deliveries, and IAR educationLead regulatory exams, audits, information requests, and consultant-supported remediation
Portfolio Accounting System (Black Diamond)Administer Black Diamond performance reporting system, including managing client portal accessMaintain asset classifications, manual data, private investment values, and related recordsMonitor data feeds, resolve discrepancies, and audit the integrity of firmwide reporting
Quarterly BillingLead quarterly billing and validate quarter-end values, fee schedules, and account-level calculationsGenerate and audit fee calculations, interpret exceptions, and make supported adjustmentsOversee fee collection, reconcile results, and post client billing statements on schedule
IT and CybersecurityOversee implementation and maintenance of the firm's technology stack and vendor relationshipsAdminister Microsoft 365, SharePoint, email, user access, and core cloud systemsManage cybersecurity policies, testing, training, vendor oversight, and incident readiness
Alternative Investments AdministrationServe as the primary operational contact for alternative investments and external administratorsCoordinate subscriptions, redemptions, capital calls, distributions, and supporting documentationMaintain investment records, valuations, ownership data, and manual system updates
Business AdministrationManage relationships with landlords, insurers, vendors, and service providersCoordinate state registrations, annual reports, entity records, and recurring filingsAdminister business insurance programs, including E&O, cyber liability, and general business coverage
Miscellaneous OperationsManage annual tax-document communications and Form 5500 preparation, signature, and filingOwn Required Minimum Distribution tracking and ensure each client fulfills their requirementMonitor client cash reserves and liquidity needs and coordinate rebalancing with advisory team if neededLead class action administration, process improvements, and special projects supporting growth
Desired Qualifications·        Exceptional attention to detail and high standards for accuracy and follow-through·        Self-sufficient and dependable, with the judgment to move complex work forward independently·        Critical thinker and practical problem solver who documents and improves processes as they work·        Highly organized across concurrent workflows, seasonal cycles, projects, and deadlines·        Comfortable reconciling detailed data, numbers, and anomalies·        Able to manage extensive detail while maintaining a clear view of broader priorities·        Professional, discreet, and service-oriented, with strong communication and computer skills
This role is likely a good fit if you...·        Value a trusted small team and take pride in essential behind-the-scenes work·        Enjoy both precise recurring work and open-ended problem solving·        Anticipate needs and bring organized recommendations without waiting for direction
Schedule and CompensationWe prioritize flexibility and work-life balance, believing that people do their best work when professional responsibilities and personal commitments are thoughtfully aligned. This is a full-time position with a flexible schedule that can be tailored to the right candidate, including the option to structure the role around approximately 35 hours per week if fewer hours are desired. The role also includes work-from-home flexibility of up to one day per week to start, with in-office attendance expected for key meetings, collaborative work, and other business needs.
The position is paid hourly to provide additional flexibility, with an expected base rate of $38 to $47 per hour, depending on qualifications and relevant operations, compliance, or wealth management experience. The role is also eligible for an annual performance-based bonus. Benefits currently include a retirement plan with company match, 12 paid holidays per year, accrued paid time off, paid volunteer days, and a wellness stipend. xzbcwsv
To apply, submit resume and cover letter explaining what you find interesting about the role and why you think you might be the right fit to .