About Us

Helping Businesses Save Time

Loophole Automation designs and implements low‑code and AI‑powered solutions that eliminate repetitive tasks, surface better data, and free teams to focus on the work that really matters.

Who We Are

Who We Are

Who We Are

Loophole is a tight‑knit team of problem‑solvers obsessed with turning messy, people‑heavy processes into button‑click simplicity. We design, prototype, and ship in weeks—not quarters—so your team feels the impact fast.

4 Partnerships

Streamlined their workflows with Loophole solutions.

4 Partners

Streamlined their workflows with Loophole solutions.

4 Partnerships

Streamlined their workflows with Loophole solutions.

500+ Hours

Reducing tedious work and saving time through automation.

500+ Hours

Reducing tedious work and saving time through automation.

500+ Hours

Reducing tedious work and saving time through automation.

95% Faster

Clients see improved efficiency within the first three months of usage.

95% Faster

Improved efficiency within the first three months of usage.

95% Faster

Clients see improved efficiency within the first three months of usage.

Our Trusted Partners

Our Values

Our Values

The Values Behind Loophole

Our values guide every system we build at Loophole. From practicality to trust, we’re committed to solutions that genuinely improve how businesses operate—and make life easier for the people behind them.

Innovation with Purpose

We apply cutting‑edge tech only where it drives measurable ROI.

Innovation with Purpose

We apply cutting‑edge tech only where it drives measurable ROI.

Innovation with Purpose

We apply cutting‑edge tech only where it drives measurable ROI.

Radical Transparency

Clear pricing, clear scopes, and no black‑box magic.

Radical Transparency

Clear pricing, clear scopes, and no black‑box magic.

Radical Transparency

Clear pricing, clear scopes, and no black‑box magic.

Empowerment, Not Replacement

Automation frees proffesionals to do work that matters.

Empowerment, Not Replacement

Automation frees proffesionals to do work that matters.

Empowerment, Not Replacement

Automation frees proffesionals to do work that matters.

Partner‑First Mindset

Your success metrics define ours.

Partner‑First Mindset

Your success metrics define ours.

Partner‑First Mindset

Your success metrics define ours.

Out Team

Out Team

Out Team

Meet the Minds Behind Loophole Automation

Technology without strategy is just noise. Our founders combine deep domain expertise with rock‑solid technical chops to deliver automation that actually sticks.

Sean Sakaguchi

Co-Founder & CFO

Former Vice President in Guggenheim Securities Consumer and Retail practice, and previously worked in the Liability Management / Capital Structure Advisory practice. Mr. Sakaguchi’s experience includes advising companies, sponsors, creditor constituents, and sovereign / municipal governments on M&A, financing, restructuring, liability management, and leveraged finance transactions across a range of industries. Throughout his career, Mr. Sakaguchi has advised clients in connection with over $1.5 billion in M&A transactions, over $1.4 billion of financing transactions, and over $200 billion of restructured liabilities. Mr. Sakaguchi’s most recent corporate advisory transaction experience includes representing Keurig Dr. Pepper, Kelso (Eagle Foods), California Pizza Kitchen, PhyMed Healthcare Group, and EPIC Midstream. Notable sovereign and municipal advisory roles include representing the State of California (in connection with the PG&E bankruptcy), the Commonwealth of Puerto Rico, Guinea-Bissau (in connection with restructuring bilateral Taiwan Ex-Im debt). Creditor and key stakeholder experience includes advising the First Lien Term Loan Lenders in Claire’s Inc, secured creditors of Seadrill (NADL), and the Ad Hoc Creditors Committee for Venezuela / PDVSA. Prior to joining Guggenheim in 2018 as part of the firm’s acquisition of Millstein & Co., Mr. Sakaguchi was an analyst at Millstein & Co, a boutique, restructuring-focused investment bank. Mr. Sakaguchi is a graduate of Claremont McKenna College where he received a B.A. in Philosophy, Politics, and Economics; and Economic-Accounting.

Sean Sakaguchi

Co-Founder & CFO

Former Vice President in Guggenheim Securities Consumer and Retail practice, and previously worked in the Liability Management / Capital Structure Advisory practice. Mr. Sakaguchi’s experience includes advising companies, sponsors, creditor constituents, and sovereign / municipal governments on M&A, financing, restructuring, liability management, and leveraged finance transactions across a range of industries. Throughout his career, Mr. Sakaguchi has advised clients in connection with over $1.5 billion in M&A transactions, over $1.4 billion of financing transactions, and over $200 billion of restructured liabilities. Mr. Sakaguchi’s most recent corporate advisory transaction experience includes representing Keurig Dr. Pepper, Kelso (Eagle Foods), California Pizza Kitchen, PhyMed Healthcare Group, and EPIC Midstream. Notable sovereign and municipal advisory roles include representing the State of California (in connection with the PG&E bankruptcy), the Commonwealth of Puerto Rico, Guinea-Bissau (in connection with restructuring bilateral Taiwan Ex-Im debt). Creditor and key stakeholder experience includes advising the First Lien Term Loan Lenders in Claire’s Inc, secured creditors of Seadrill (NADL), and the Ad Hoc Creditors Committee for Venezuela / PDVSA. Prior to joining Guggenheim in 2018 as part of the firm’s acquisition of Millstein & Co., Mr. Sakaguchi was an analyst at Millstein & Co, a boutique, restructuring-focused investment bank. Mr. Sakaguchi is a graduate of Claremont McKenna College where he received a B.A. in Philosophy, Politics, and Economics; and Economic-Accounting.

Sean Sakaguchi

Co-Founder & CFO

Former Vice President in Guggenheim Securities Consumer and Retail practice, and previously worked in the Liability Management / Capital Structure Advisory practice. Mr. Sakaguchi’s experience includes advising companies, sponsors, creditor constituents, and sovereign / municipal governments on M&A, financing, restructuring, liability management, and leveraged finance transactions across a range of industries. Throughout his career, Mr. Sakaguchi has advised clients in connection with over $1.5 billion in M&A transactions, over $1.4 billion of financing transactions, and over $200 billion of restructured liabilities. Mr. Sakaguchi’s most recent corporate advisory transaction experience includes representing Keurig Dr. Pepper, Kelso (Eagle Foods), California Pizza Kitchen, PhyMed Healthcare Group, and EPIC Midstream. Notable sovereign and municipal advisory roles include representing the State of California (in connection with the PG&E bankruptcy), the Commonwealth of Puerto Rico, Guinea-Bissau (in connection with restructuring bilateral Taiwan Ex-Im debt). Creditor and key stakeholder experience includes advising the First Lien Term Loan Lenders in Claire’s Inc, secured creditors of Seadrill (NADL), and the Ad Hoc Creditors Committee for Venezuela / PDVSA. Prior to joining Guggenheim in 2018 as part of the firm’s acquisition of Millstein & Co., Mr. Sakaguchi was an analyst at Millstein & Co, a boutique, restructuring-focused investment bank. Mr. Sakaguchi is a graduate of Claremont McKenna College where he received a B.A. in Philosophy, Politics, and Economics; and Economic-Accounting.

Why us

Why us

Why us

What makes us stand out in the industry

Discover how our innovative strategies, data-driven approach, and commitment to results set us apart from the competition

Manual Work

Prone to Human Errors

Prone to Human Errors

Prone to Human Errors

Limited by Work Hours

Limited by Work Hours

Limited by Work Hours

High Labor Costs & Overhead

High Labor Costs & Overhead

High Labor Costs & Overhead

Time-Consuming Tasks

Time-Consuming Tasks

Time-Consuming Tasks

Tedious & Repetitive Work

Tedious & Repetitive Work

Tedious & Repetitive Work

Inconsistent Output Quality

Inconsistent Output Quality

Inconsistent Output Quality

Loophole Automation

AI + Human‑in‑the‑Loop

AI + Human‑in‑the‑Loop

AI + Human‑in‑the‑Loop

24/7 Automated Workflows

24/7 Automated Workflows

24/7 Automated Workflows

Scalable & Cost-Effective

Scalable & Cost-Effective

Scalable & Cost-Effective

Unified Real Time Dashboards

Unified Real Time Dashboards

Unified Real Time Dashboards

Seamless Platform Integration

Seamless Platform Integration

Seamless Platform Integration

Consistent & Reliable Output

Consistent & Reliable Output

Consistent & Reliable Output

FAQs

FAQs

FAQs

Got questions about automating your business?

Straight-shooting answers from the team that builds the workflows.

Our Products

What is business automation?

How can this save my business money?

Does this use or require AI?

Is automation difficult to integrate?

What industries leverage automation or AI?

Do I need technical knowledge to use these solutions?

What is business automation?

How can this save my business money?

Does this use or require AI?

Is automation difficult to integrate?

What industries leverage automation or AI?

Do I need technical knowledge to use these solutions?

What is business automation?

How can this save my business money?

Does this use or require AI?

Is automation difficult to integrate?

What industries leverage automation or AI?

Do I need technical knowledge to use these solutions?

Our Process

Why Loophole?

How long does implementation take?

What does it cost?

What if my processes change?

Which platforms do you integrate with?

How do you protect my company’s proprietary information?

Why Loophole?

How long does implementation take?

What does it cost?

What if my processes change?

Which platforms do you integrate with?

How do you protect my company’s proprietary information?

Why Loophole?

How long does implementation take?

What does it cost?

What if my processes change?

Which platforms do you integrate with?

How do you protect my company’s proprietary information?

Let AI do the Work so you can Scale Faster

Book a Call Today and Start Automating

Loophole LLC

2025

© All right reserved

Loophole LLC

2025