[Hiring] Operations Manager @Penbrothers

Role Description

The Operations Manager / Chief of Staff will serve as a senior operating partner to the Managing Principal, overseeing processes across Marketing, Sales, Client Onboarding & Delivery, Investment, and Finance. This is a hands-on role for someone who can connect systems, improve processes, manage priorities, and drive execution with a high degree of independence. The goal is to build a more organized and scalable operation where ownership is clear, reporting is consistent, and the Principal can stay focused on clients and strategy.

What you’ll do

• Connect and Improve Business Systems:
  • Help ensure the firm's core systems operate as one connected workflow rather than as separate tools and processes.
  • Oversee the client onboarding flow across HubSpot, AdvicePay, DocuSign, and eMoney, identifying gaps and improving handoffs between systems.
  • Maintain the sales process in HubSpot, including lead sources, pipeline information, and decline-reason tracking.
  • Identify opportunities to automate, delegate, simplify, or strengthen processes as the business grows.
• Own the Operating Rhythm:
  • Translate the Principal's priorities into clear action plans, owners, deadlines, and follow-ups.
  • Set priorities and resolve routine operational issues without requiring constant direction.
  • Monitor deadlines, open items, and dependencies and ensure work continues moving forward.
  • Identify risks early and bring forward a recommended course of action rather than simply escalating a problem.
  • Use sound judgment about what can be handled independently and what requires Principal-level input, particularly when client information or sensitive matters are involved.
• Oversee Vendors and External Partners:
  • Coordinate and manage relationships with external marketing and PR partners.
  • Work closely with outsourced investment and bookkeeping functions to ensure responsibilities, deadlines, and deliverables remain clear.
• Build and Maintain Operational Reporting:
  • Develop and maintain a recurring operating view across the firm's five core systems.
  • Track key business information, including revenue against target and other relevant operating metrics.
  • Establish a reporting rhythm that provides the Principal with a clear view of what is on track, what requires attention, and where decisions are needed.
  • Provide practical recommendations based on the information being reported.
• Manage Client Onboarding and Service Administration:
  • Coordinate end-to-end client onboarding and related administrative workflows.
  • Support processes involving custodial account opening, transfer paperwork, documentation, and record retention.
  • Ensure required steps are completed accurately and consistently.
  • Maintain organized client records, documentation, and outstanding requests.
  • Follow established procedures and escalate exceptions or compliance-related questions appropriately.
• Document and Improve Processes:
  • Create and maintain practical SOPs, checklists, and workflow documentation.
  • Identify unnecessary steps, recurring issues, and process gaps and implement improvements.
  • Make processes easier to follow, delegate, and scale as the firm grows.
• Handle Confidential Information Responsibly:
  • Work with sensitive client financial information and firm systems in accordance with approved access, security, and data-handling procedures.
  • Maintain a high standard of confidentiality and attention to detail.
  • Escalate compliance questions, exceptions, or unclear situations rather than making assumptions or improvising.

What You'll Own vs. What Stays With the Principal

This role is designed to create greater operational leverage for the Principal while maintaining clear decision boundaries. The Principal retains responsibility for:

• Client strategy and discovery
• Offers and closing
• Investment committee direction
• Final trade approval
• Activities requiring the Principal's registration or trading authority

This role owns operational oversight, coordination, reporting, and process improvement. Trading authority does not transfer to this position. On the investment side, the role is focused on oversight, coordination, and reporting, not trade execution.

What You Bring

• Cross-system operating ability.
• Prior experience in a US financial services environment such as an RIA, broker-dealer, CPA practice, or insurance agency, with exposure to client account paperwork and confidential financial data.
• End-to-end client onboarding experience.
• Reporting discipline.
• A confidentiality and screening posture that can be committed to contractually.
• Strong written and spoken English, able to explain an issue, recommend a course of action, and work closely with a US-based principal.

Nice to have

• Hands-on experience with HubSpot, AdvicePay, DocuSign, eMoney, Altruist, Wave
• SOP writing
• Meeting preparation

What success looks like

• Each of the five systems has fewer single points of failure than it did at the start, and the ones that remain are there by choice.
• The Principal can hold attention to clients and strategy because the operating rhythm runs without them.
• A recurring operating report exists across all five systems, including revenue against target, and arrives without being requested.
• Client onboarding and the related account-administration workflows are completed accurately and on time, with clear ownership and no missed follow-ups.
• Processes are documented, open work is visible, and recurring problems stop recurring.

What You’ll Get

• Meaningful work & Growth: We take every opportunity to stretch ourselves and deliver an excellent client experience.
• Employee as our biggest asset: We are genuinely invested in our people’s career and welfare.
• Global reach & local impact: Get to work with high-growth startups and dynamic companies from the comfort of your own home.
• Powering global startups: We’ve created 1,400 Filipino jobs that empower global start-ups to focus on growth.