Skills Matrix

By: simonguide

On: 2013.08.16

Tagged: about, insurance, leadership, life long learning, risk management, security, technology,

As I've noted previously, my goal is to be in a senior-level leadership position in 7-15 years. The ideal would be CIO, CTO, or CISO for either an insurance company or technology company. To achieve that sort of role it a combination of education and experience is required. Education is very easily quantified while real world experience is not. As such, I decided to create this Skills Matrix to document and advertise the experiences I've achieved. This is something we used to do in Search and Rescue to make it easy to build rescue teams based on specific situational requirements such as avalanche exposure, high-angle rope rescue, helicopter long line access, etc.

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Data Problems Faced by the Insurance Industry

By: simonguide

On: 2013.02.27

Tagged: data, insurance, technology, life long learning,

I’ve got a data problem. Well, we [Guardian Risk Managers] do. As with most insurance companies, a lot of reporting is done in Excel spreadsheets. We are generating a rolling earthquake aggregate report based on a bordereaux of policies. We were also generating a contract-year report based on those same spreadsheets but realized it was collecting incorrect data as the contracts renewed/changed. I am now in the process of building a full database solution to collect the data, never loose it, and provide automated reporting/analysis.

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Hacking: The Next Generation

By: simonguide

On: 2013.02.18

Tagged: life long learning, technology, amorphous_projects, reading list, risk management,

These are notes from:

Nitesh Dhanjani, Billy Rios, Brett Hardin (2009) ~ Hacking:The Next Generation ~ O'Rielly Media

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Cross Site Scripting (XSS) Experiment

By: simonguide

On: 2013.02.08

Tagged: security, life long learning, technology,

For obvious reasons server/web security has become crucially important to me recently.

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Interviews with Naveen Jain

By: simonguide

On: 2012.11.28

Tagged: technology, life long learning, reading list,

This is a really cool series of interviews with Naveen Jain of Infospace.

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I'm a SysAdmin!!!

By: simonguide

On: 2012.11.19

Tagged: technology, insurance, life long learning, personal,

I realized this weekend, I'm going to be required, by my employer, to be a SysAdmin (System Administrator). I'm developing some very cool web applications for them from scratch in an organization that's not tech related in an industry that is not current on tech. As part of that, I have chosen the programming language (PHP), chosen the database (MySQL or SQLite), designed the database architecture, and am now writing code. I am also shopping for data centre's, hosts, or server providers to host these applications. At a minimum we have to be on VPS's or private servers; shared servers are not secure or fast enough for our needs. Also, typically shared hosting services do not offer the option to scale to a VPS or managed service so we might as well skip that stage while we're small. Over the weekend, I realized by default I will have to be the SysAdmin for these servers as no one else in the company can do it (I also have to be in charge of risk management, backup, data recover, and business continuity but that's a post for another day). My employer doesn't, nor will the ever, know what a great deal they're getting. The average SysAdmin makes $75-85k/year and asking someone to underwrite technical insurance products, write computer code, develop IT risk management practices, and manage systems is rare. They're getting a great deal in an employee who can do it all so it's a good thing I'm incredibly happy there, happy to work weekends & evenings, and will be at the company for a very long time.



By: simonguide

On: 2012.11.11

Tagged: leadership, insurance, personal, life long learning,

My career plan is to act in a leadership role such as CIO or CTO for an insurance company. As such, I thought it valuable to start outlining a list of necessary skills/knowledge.

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Insurance Technology Development


On: 2012.06.22

Tagged: technology, insurance, life long learning,

I was just telling a friend about the insurance technology I'm working on when I came to the following realizations:

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How To Study Effectively

By: Simon Le Pine

On: 2012.01.12

Tagged: life long learning, personal, reading list,

It came to my attention that one aspect to getting more done in a day is learning more effectively and making the most of my time studying for MBA courses. If I were to have to repeat a course its a waste of time, if I can spend 1 hour studying rather than 2 I can spend the second hour on other projects.

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The Two Cultures and A Second Look

By: Simon Le Pine

On: 2012.01.12

Tagged: life long learning, personal, random, reading list,

The Two Cultures and A Second Look (C.P. Snow, 1959) is yet another one I stole off my fathers shelf. This book is so obscure I couldn't find a link on Google Books.

Proper citation:

Snow, C.P. (1959). The Two Cultures and A Second Look.

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Archive of Posts

The Plague of the Black Debt - How To Survive the Coming Depression

The Future of Leadership

How Will You Measure Your Life?

American Catalyst Interview W/ Kyle Bass

Who Moved My Cheese?

10 Predictions About Cloud Computing

Reading List

Financial Blogs & Literacy

CAIB1 Key Terms

CAIB1 Ch. 1-1

Business & Economics - MIT

Life Long Learning #1 - The Economist Today

Life Long Learning - Outline

Ingvar Kamprad

This is the blog of Simon Le Pine. I write about a number of varied topics including my technology startup, the insurance company I work for, my running/climbing/skiing, and the MBA I'm working towards. I organize posts into the following categories to make browsing by topic easy:

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