Director of Operations (Colorado Springs)

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.

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 Compliance

Administer the compliance program and develop towards becoming the firm’s Chief Compliance Officer

Maintain examination-ready records and coordinate filings, client deliveries, and IAR education

Lead regulatory exams, audits, information requests, and consultant-supported remediation

Portfolio Accounting System (Black Diamond)

Administer Black Diamond performance reporting system, including managing client portal access

Maintain asset classifications, manual data, private investment values, and related records

Monitor data feeds, resolve discrepancies, and audit the integrity of firmwide reporting

Quarterly Billing

Lead quarterly billing and validate quarter-end values, fee schedules, and account-level calculations

Generate and audit fee calculations, interpret exceptions, and make supported adjustments

Oversee fee collection, reconcile results, and post client billing statements on schedule

IT and Cybersecurity

Oversee implementation and maintenance of the firm's technology stack and vendor relationships

Administer Microsoft 365, SharePoint, email, user access, and core cloud systems

Manage cybersecurity policies, testing, training, vendor oversight, and incident readiness

Alternative Investments Administration

Serve as the primary operational contact for alternative investments and external administrators

Coordinate subscriptions, redemptions, capital calls, distributions, and supporting documentation

Maintain investment records, valuations, ownership data, and manual system updates

Business Administration

Manage relationships with landlords, insurers, vendors, and service providers

Coordinate state registrations, annual reports, entity records, and recurring filings

Administer business insurance programs, including E&O, cyber liability, and general business coverage

Miscellaneous Operations

Manage annual tax-document communications and Form 5500 preparation, signature, and filing

Own Required Minimum Distribution tracking and ensure each client fulfills their requirement

Monitor client cash reserves and liquidity needs and coordinate rebalancing with advisory team if needed

Lead 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 Compensation

We 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 .

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 .