Joe Giglio
Carolina Yankee
Remote First
Stock Options Trader
Seasoned Software Director
Time For a Change...
After almost 30 years in software management, I have been through my share of booms, busts, bankruptcies and buyouts.I love the work but hate the business!I have pivoted into Stock Option Trading and I am teaching others how to supplement their income. My recently published book titled "Options to Cashflow" is available on Amazon.
Quality Driven, Customer Champion, Big Picture Thinker
Teams do their best, and most valuable, work when they have a deep understanding of their products, domain and customers.Having started my career in Technical Support and QA, I bring a 360 degree view to the Software Development process.Software is more than "code"; it needs to solve real problems for your customers. I build Engineering teams that have the same "Big Picture" philosophy.
I have been the the first employee of a tech startup, a Director at a very successful, slow moving enterprise and almost everything in between.This website will serve to outline the principles, philosophies and lessons that have helped shape my career.I am always on the lookout for opportunities where my experience can help individuals and companies grow and become more successful.
I wrote the book on remote work, namely “Making Remote Work, Work For You“.I am also the creator of the “Remote Work Master Class” video series and Remote Scorecard.
Workers are demanding more from their jobs while their employers are comfortably back in the driver's seat. This job market is very challenging and the tension is real.The COVID-19 pandemic forced us to re-think previously accepted norms about what it means to “go to work”.A Gallup poll suggests that 1/3 of workers would change jobs for a more flexible, remote schedule. This suggests that workers, especially younger ones, are viewing remote work as a valuable benefit. To recruit and retain talent, remote work is becoming a must-have.Remote working has been found to reduce soul crushing commutes, improve job satisfaction, enhance productivity and creativity, increase retention and reduce distractions. In addition, allowing for flexible work locations gives the business financial and strategic advantages. Check out this recent WSJ article for more information on people moving to smaller cities and taking their jobs with them.There is great talent all around the world. Why limit yourself to only hiring from one area? Hiring from the global talent pool can help companies increase their global presence while decreasing their diversity deficiency.Where you are born, or where you live shouldn’t limit your employment opportunities. And where your company is located shouldn’t limit who you can hire. Human potential has no boundaries and technological advancements have flattened the world, minimizing the negative impact of geographic distance.Companies that successfully embrace a Remote First model are able to take advantage of a 24 hour work day where teams pass work across “shifts” using a methodology known as "Following the Sun".Obviously, remote work is not an option for everyone. There will always be those industries that require team members to be on location. For the rest of us, we should take advantage of working during a time in history where our location just does not matter much. Many workers can thrive remotely as long as they have a modern device, reliable connectivity… and the support of their company. Culture and trust mean everything to the success of remote work.Remote work is a spectrum. Some companies treat “work from home” as a perk, some are "hybrid" and other companies have reworked their protocols to make remote workers "first class citizens". Such companies have processes in place, such as "asynchronous communication", allowing their employees to work effectively “wherever, whenever”. (Read my LinkedIn article for more information on "asynchronous work".)All that being said, it is important to acknowledge that remote work is certainly not without some very real challenges. To be successful, it must be understood, supported and nurtured by company leadership. It should not be treated as a stopgap or experiment.I admire the culture of companies who have successfully embraced the remote first model such as Basecamp, Automattic, Buffer, Gitlab, Zapier, Doist, Taxjar and Help Scout. These companies write about their culture in blogs and books. This helps increase the positive exposure of these companies since many others have an interest in building a successful remote culture.Successful “remote first culture” can be viewed as a product and these pioneering companies are considered the subject matter experts and grandparents of the remote work movement.Some suggested reading:Making Remote Work, Work For You
The Year Without Pants
Remote
Zapier’s Ultimate Guide to Remote Work
Distributed
Management Style
Servant LeaderTeam SuccessEmpathyRespectHonestyHumilitySense of HumorCareer GoalsMentorship
I am an empathetic servant leader who takes pride in mentoring people and helping them succeed. I work to make my team successful by establishing trust, removing impediments, mentoring and investing in each member’s growth.I have the ability to communicate at all levels with honesty, empathy and a sense of humor. I have managed teams through very challenging times of low morale and kept the team together, motivated, engaged and productive.Each team member’s career path and goals should be well defined and discussed at regular intervals. This should be coupled with a list of milestones and obstacles to keep expectations aligned.I treat everyone with respect but don’t necessarily believe in “treating everyone equally”. You need to understand everyone’s individual personality, quirks, motivators, weaknesses and strengths to best guide their success.Engineers should be more than mere “coders”. As their careers progress, skills other than technical competency come into focus. Obviously, technical skills are important but the best Engineers are able to use their soft skills to make an impact, influence, impress and mentor. A great manager can help Engineers grow into leaders by refining these skills.Though managers may not always “contribute code”, I believe it is still important to be able to understand key technical concepts and “talk the talk” to earn the respect of the team and help facilitate solutions to technical problems. A manager should have deep product and workflow knowledge, domain expertise and an understanding of the daily challenges that face the team.As a manager, I consider myself an advocate for the welfare of my teams AND the company. It is important to balance Engineering’s desire to work on interesting technology with the needs of the product and company. It is essential to find harmony between technical debt and the pace of innovation, learning, quality and support.I have an exceptional eye for detail, ask probing questions and push my teams to develop innovative solutions.
Quality Driven
StakeholdersThree AmigosAutomated TestingContinuous IntegrationContinuous DeploymentUnderstand your CustomersOwnershipAccountability
Releasing quality software is not an accident! It is a work of art requiring executive sponsorship and the coordination of several stakeholders.I am an advocate of the Three Amigos Development Strategy. This approach requires stakeholders from the Business, Development and Testing teams to reach a common, shared vision of what is being built. All groups involved should agree on Acceptance Criteria and the Definition of Done. I would even go to FOUR Amigos if you want an additional layer of value and consensus. Include the Support team to take these product planning sessions to the next level.This strategy helps to shape a better product by improving communication, forcing clear requirements, removing ambiguity and allowing each represented group to give valuable input based on their skills, perspectives and experience.Software features do not exist in a vacuum. They must be created, shaped, nurtured and supported. Consensus on what to build is an often overlooked first step on the path to high quality software."Defects" found during the planning and discussion phase are much easier to address than real bugs found during the development phase.“Software testing” encompasses several disciplines including manual, unit and automated testing; validation; verification and continuous integration. Testing is best done throughout the development cycle by an integrated team and should not be treated as an afterthought after the code is “thrown over the wall”.Just because a company has the technical ability to move code quickly through the pipeline does not mean that it is always best to do so!It is important to know your industry and understand your customer’s risk tolerance. Moving quickly and deploying code several times a day will introduce risk. Some customers may tolerate bleeding edge features and occasional instability but many “high value customers” often view the most important features as speed, stability and security.Although there is obvious value in internal testing, some of the most valuable testing is arguably done in Production. Slow rollouts to targeted customers with feature flags is an ideal way to gather real-world customer feedback and performance metrics. Software is never “done” and we should expect to have to tweak and iterate based on feedback, associated metrics and support cases.There is more to software than its code. Just because the “code is done” does not necessarily mean the feature is ready to be released. The Four Amigos should decide on the Definition of Done to keep the company aligned.For example:
Has the test suite been updated?
Does the documentation require updated screenshots?
Does the website need to be updated?
Does the knowledge base need to be updated?
Will there be any impact on pricing plans?
Has the Support team been given a chance to test the feature and ask questions?
Will the feature behave differently on a new install vs. an upgrade?
What is the rollout strategy?
Have we added the necessary logging, instrumentation and performance metrics for the Infrastructure team?
Etc...
I drive my teams to release “testable code” that is simple to deploy, monitor, support and iterate. Once code is deployed, the Engineering team must continue to take responsibility for it. “Abandoned code” is very expensive to maintain and support.
Whole Company Support, also known as All Hands Support, has been gaining traction with companies that want to build a more well-rounded organization with deep levels of customer empathy.Support is often viewed as a cost center and position of minor value. I take the opposite view and believe Support is one of the most valuable teams in a company.They are often product experts and have a thorough understanding of the customers and the most common use cases. They are on the front lines keeping customers calm while making excuses for product shortcomings.There is often a disconnect between the people who build the software and those who use it. The Support team helps to bridge that gap by playing the role of customer advocate and liaison between the customers and Product team.Customer Support is a craft and not everyone is good at it.If there are team members in the organization that do not have the confidence, patience or communication skills to directly handle support requests, all is not lost!The goal of Whole Company Support is not necessarily to create more support agents, although that may be a positive side effect.Rather, the goal is to increase collaboration and build a company where everyone develops a deeper understanding of their products and empathy for their customers.Everyone can help the company meet these goals by partnering with a member of the Support team, reviewing support cases for common themes and committing to using their skills to help solve problems and improve the customer experience.Some examples:
If you are a documentation writer you may find that poor documentation for a certain feature is causing frustration.
If you are on the website team, you may come to find out that the pricing page is too confusing and you can improve it.
If you are a Developer, bug reports may help you realize that one of the product features is clunky and you can help streamline it.
Helping the Support team and solving problems for your customers is eye opening and empowering!After all, if we are not all working to better understand our customers and solve their problems, what are we working on?
Projects, Podcasts, Articles
Lifelong LearningSharing KnowledgeCreating ValueGiving BackMentoring
The Truth about Vibe Coding with Windsurf…Better than Cursor? – Video series documenting my journey and challenges with Windsurf and Claude Sonnet 3.5.Options to Cashflow – I have thrown myself into the world of Stock Options to supplement my income. In this course, I will discuss strategies and the psychology of successful stock option trading. Turn your assets into cashflow!Remote Scorecard – Think Glassdoor for remote companies. The best remote companies do more than allow employees to “work from home”. Their culture is built around supporting and nurturing remote work and they follow a similar formula. The best “Remote First” companies eventually evolve into “People First” companies.Chief Remote Officer – Training and consulting to help make your company more “Remote First”.“Making Remote Work, Work For You” Kindle Book – Written before the pandemic and just as relevant as ever. A timeless classic.Podcast AppearancesProduct Driven – “We Still Need Software Engineers, Even With AI”Be Remote – “Making Remote Work, Work For You”Distant Job – “Why Some Companies Fail at Building a Healthy Remote Culture”ArticlesReview of AI Code Tools – A multi-part series on my experiences using AI coding tools to create Enterprise level software. Just how close is AI to replacing software developers?The Case for Bitcoin in 2025 – Cryptocurrencies are confusing, volatile and seem to lack any practical purpose. Yet there are still some very smart people saying 2025 will be the year that Bitcoin goes to ONE MILLION DOLLARS per coin. But why?The Importance of Whole Company Support – Teams do their best, and most valuable, work when they have a deep understanding of their products, domain and customers.Quality is Everyone’s Job: How to Get Your Dev Team to Embrace Automation – In an attempt to maximize efficiency, many organizations are asking Developers to contribute more to the testing effort, blurring the lines of responsibility between “Development” and “QA”. After all, nobody knows the code better than the Developer who wrote it… but are they really the best candidates to test it?
360 Degree View
I often say I am a Remote First, Quality Driven, Customer Champion.Teams do their best, and most valuable, work when they have a deep understanding of their products, domain and customers.I have worked as the first employee of a tech startup, a Director at a very successful; slow moving enterprise and almost everything in between. This website will serve to outline the principles, philosophies and lessons that have helped shape my career. I am always on the lookout for new opportunities where my experience can help companies grow and be more successful.In my two+ decades in the software industry, I have worked alongside Founders, Executives and Product Managers to help create, test, build and support help desk, call center and CRM software. I have built and managed Development, Quality Engineering and Support teams. I believe these teams should be treated as complementary with Support being recognized as respected customer advocates instead of as a “cost center.”My experience managing these different teams gives me a unique, 360 degree view of the software development process. I have sound, real-world knowledge of the stages and challenges of the software development cycle including the gathering of product requirements, development, testing, documentation, deployment, training, implementation, support, and maintenance. Releasing quality software is not an accident or luxury. It requires discipline, coordination, executive sponsorship and an understanding of your customer’s risk tolerance.I am a seasoned and empathetic servant leader who excels at mentoring people to success. I have helped people launch their careers by developing onboarding training classes for diverse roles such as Sales, Engineering, Support, Marketing and Executives.I have long been a champion for “Whole Company Support” and pioneered it at Desk.com. Through this practice, you build multi-dimensional teams with deep product expertise, industry knowledge and customer empathy. We should proudly eat our own dog food (or drink our own champagne.)I have managed geographically dispersed teams, understand the challenges and benefits and know how to make it successful. I managed Engineering teams at Salesforce and was instrumental in helping them find success with a remote-friendly team model.The future of work is remote although it is important to acknowledge and understand its challenges.