Director of Technology & Digital Transformation (Remote, USA) FULL TIME

Job Description

Job Description

Job Description - Director of Technology & Digital Transformation

Title: Director of Technology & Digital Transformation

Location: Remote (USA-based)

Status: Full-Time Contractor to Employee

Salary Range: Based on Experience

Reports to: Managing Partners

Overview:

Trophy Point Investment Group is seeking a forward-thinking Director of Technology & Digital Transformation to lead and execute the company’s digital growth strategy. This role is critical to modernizing our infrastructure, optimizing internal workflows, and supporting our lending and investor operations through scalable, secure technology solutions.

We are looking for a hands-on leader who comes from a structured, high-performing lending or real estate environment — someone who has the skills and vision to lead digital innovation but hasn’t had the opportunity to take ownership due to red tape or flat organizational structures.

Ideal Background:

You’ve likely worked in the technology department of a large real estate lender, REIT, private equity firm , or mid-market financial institution — examples include:

• Newrez, Greystone, Arbor Realty, Berkadia, CBRE, Freddie Mac, SitusAMC, Marcus & Millichap, Walker & Dunlop, or JP Morgan Real Estate Lending.
• You may be a Senior Systems Analyst, Enterprise Solutions Architect, or Tech Project Manager with 5–10 years of experience — and now ready to own and lead.

Responsibilities:

Digital Systems Strategy & Execution

• Overhaul and optimize our current tech stack including CRM (HubSpot) , mortgage automation software, borrower/investor portals, and internal communication tools.
• Create and implement scalable digital workflows for loan origination, servicing, and investor communications .
• Serve as the point person for all systems integration and workflow automation across departments.

Technical Oversight

• Manage internal systems: HubSpot, Google Workspace, file storage systems (e.g., Dropbox/Drive), cybersecurity tools (VPN, MFA), and performance dashboards (e.g., ClickUp, PerformYard).
• Work alongside our external vendors and third-party dev teams — you will evaluate, engage, and manage outside experts to execute the roadmap when needed.

Security & Infrastructure

• Establish and maintain best-in-class IT policies for data security, access control, backups, and vendor compliance .
• Oversee the implementation of security best practices for remote staff and cross-border contractors.

Reporting & Analytics

• Build reporting capabilities and visual dashboards to drive data-driven decision-making across departments.
• Partner with accounting and executive leadership to provide real-time metrics for loan pipeline, sales, investor activity, and operational performance.

Leadership & Collaboration

• Collaborate with department heads in Loan Origination, Servicing, Finance, Marketing, and Investor Relations to align tech needs with business goals.
• Be a key driver in transforming TP from operational to technology-enabled , preparing us for rapid growth in 2025 and beyond.

Required Qualifications:

• 5–10 years in a tech leadership, systems analyst, or project management role within real estate lending, private equity, or commercial finance .
• Strong experience in CRM systems (HubSpot preferred), loan software integrations, and digital project execution.
• Experience managing vendors and outside consultants to deliver technical solutions.
• Deep understanding of enterprise systems and how to balance customization vs. scale.
• Strong written/verbal communication and organizational skills.

Preferred Attributes:

• Familiarity with Mortgage Automator, PerformYard, ClickUp, or similar tools.
• Prior experience building out a loan operations or investor-facing tech infrastructure.
• Ability to evaluate and recommend new technology based on ROI, not trendiness.
• Someone who is ready to lead , not follow — and be hands-on, not just strategic.

Why Join Trophy Point:

• Lead and shape the entire technology function at a fast-growing private lender.
• Report directly to executive leadership and have true decision-making authority.
• Help transition a traditional lending firm into a digitally empowered platform.

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