Aligning Teams & Business Needs

Experienced technical leader with 15+ years in software

Randall Tombaugh

Based in Honolulu  |  West Coast Hours
With 15+ years in software, I have:
Written, debugged, and reviewed lots of code
Built entire production applications
Architected full systems from scratch on AWS
Bootstrapped DevOps processes and tooling
Mentored dozens of junior & senior engineers
Started and grown engineering teams
Led organizations through security & operations audits
Delivered management training across organizations
Driven C-level initiatives to successful outcomes

Testimonals

Feedback From Managers | Feedback From Direct Reports
Skyler Hair
Droplet CTO
"
Randall frequently demonstrates strategic and tactical alignment and a mastery of his domain. He excels at earning trust and consistently demonstrates that the trust is well-founded. I am constantly blown away by his ability to context-switch and organize so many different initiatives at once. Randall is a great leader. "
"
What I most value in Randall is his personalized and genuine approach to managing. He so tactfully creates an environment where I feel like I'm reporting to my friend, but in a way that does not cheapen his role as a manager. His sense of empathy and desire to treat me and my coworkers with respect is invaluable in his leadership role."
Matt Stauffer
Droplet Engineer
Charles Jones
Droplet Engineer
"
He is very sensitive to the needs of the engineers on the team and making sure they are unblocked as quickly as reasonably possible. Randall wants everyone on his team to succeed and achieve their goals and he always follows through on making sure that happens."

Management Philosophy

Focused on People | Focused on Outcomes
Respect What Others Value
Some folks value getting through all of the items on a to-do list. Others value thinking deeply about a problem to understand it from all sides. Some folks value getting recognition. Others value the camaraderie of working closely with others.

Understanding what others value and respecting what they value is crucial to good management. Alignment between what a person values and the needs of the projects assigned to them is one of the best predictors of success. Skills can be learned. Experience can be gained. But a misalignment of values is hard to overcome. Telling someone not to value what they value rarely works. Instead, align the projects, tasks, and duties owned by the team with the right individuals based on what those individuals value.
Processes Don't Replace People
When it comes to business processes, it is either the case that following the process requires context and the ability to make judicial decisions or it doesn't. If it doesn't, then the process should be fully automated. If it does require context to make judicial decisions, then identify the correct decision-makers and fully train them, enabled them to make decisions, and trust them with those decisions. When applicable, provide feedback to make better decisions next time.

Business processes are essential. They are a tool for helping people within an organization make effective decisions that align with business goals and strategies. But business processes are not a replacement for people and they can not ensure good decisions are made if the people involved in the process are not trained and supported.
Overcommunicate Strategy
It is challenging to be aware of what you know. When faced with a situation or dilemma, the right course of action often feels intuitive and obvious. It only becomes apparent that it isn't so obvious when someone else faces the same situation or dilemma but responds to it differently.

Delegating to others requires thinking deeply about the strategies you have internalized. Are your internalized strategies integral to achieving business goals? If not, then allow others to adapt their own strategies. But if your internalized strategies are integral to achieving business goals, then communicate them explicitly to others, and recognize it will take time for them to fully internalize the strategies themselves.
Always Act in Good Faith
We all have goals we're working towards. We all have certain things we value. Sometimes we find ourselves in conflict with others and their goals and values. This is inevitable in an organization of any size.

One must recognize when these tensions do arise. Be honest with yourself and the other person that there is conflict, and work to resolve that conflict in good faith. This involves taking the other person's goals and values seriously and looking for solutions that are satisfactory to everyone involved. Avoiding the conflict, or worse, attempting to railroad the other person and "win" the conflict is poisonous to organizations. This is almost always easier said than done and requires conscious and deliberate effort to listen to others, question your own motives, and mean what you say.

Work History

Large Corporations | Late & Early Stage Start-Ups | Founder
2023
2021
2019
2017
2015
2013
2011
2009
2007
2005

Droplet

Head of Engineering
FEB 2021 - CURRENT
Provo UT (Remote)

Started as one of the first half-dozen employees and have been crucial in driving engineering and product as the company has grown from $45K to over $3M in ARR.

Productized the original POC version of the application. Set up a developer-friendly codebase, the DevOps processes and tooling, and all AWS infrastructure. Hired the engineering team that I have been directly managing while also providing architectural review, product roadmap management, bug and feature triage and more. As the most experienced manager in the company, I have provided management and leadership training company-wide.

Introduced a number of large and small features, including sophisticated role-based access, omni-search of all submission data, custom PDF generation, code & visual editors of the product's forms and workflows, and more. Oriented the product and engineering team around security, availability, and reliability first and managed 3rd party PEN testing and SOC2 audits. Responsible for all incident management.

Decision Research

Architect and Technical Leader
MAY 2020 - FEB 2021
Honolulu HI

Hired as an architect on the platform team, but quickly discovered that the client services team was falling behind on a million-dollar contract. Proactively negotiated a leadership position on the client services team and with a small team of junior engineers, fixed crucial architectural issues and delivered custom client features that had previously been months behind schedule.

Fusebit.io

Co-Founder and Head of Engineering
FEB 2019 - SEPT 2019
Redmond WA (Remote)

Co-founded with two colleagues from Auth0.

Fusebit was a serverless platform with a focus on SaaS integration and included a multi-region serverless service, an embeddable Javascript editor that seamlessly worked with the service, and a CLI to manage accounts, users, and serverless functions. The product included a sophisticated accounts/users/auth mechanism to support embedding into other SaaS products. As Head of Engineering, I built most of the service, all of the DevOps and the CLI tools, as well as the product website.

I left Fusebit prior to the other founders doing a seed round for $3.5M. Fusebit closed down in January of 2023.

Auth0

Software Engineering Manager
JUNE 2017 - FEB 2019
Bellevue WA (Remote)

Started as a senior software engineer and was then promoted to manage the Webtask team, which was building out a second product to Auth0's original identity offering. The Webtask team was considered as a start-up inside of a start-up. I was responsible for everything from new features to DevOps, documentation, and customer support. Managed a team of five software engineers.

Webtasks was one of the first "Serverless" platforms in the industry and predated AWS Lambda, Google Functions, and Azure Functions. It was both a standalone product (as Extend.io) and enabled the extensibility of Auth0's main identity product. It provided a secure sandbox to run untrusted JavaScript, isolated per customer, and running at scale.

Hawaiian Airlines

Senior Software Engineer
OCT 2016 - MAY 2017
Honolulu HI

Lead developer of the API Team, responsible for leading a team of three developers tasked with redesigning and implementing the APIs to be used by the mobile and web clients, moving current RPC functionality to AWS as RESTful endpoints.

Microsoft

Senior Software Engineer
OCT 2008 - SEPT 2014
Redmond WA

Held numerous senior software engineering roles during my time at Microsoft.

Originally developed framework components for the .NET WCF Framework and the ASP.NET Web API Framework. Later moved to the Azure team, where I designed and developed the iOS, JavaScript, and .NET client frameworks for Windows' Azure Mobile Services. At the end of my tenure, I owned credit card encryption/decryption in Microsoft's commerce division, which handled all online Azure, Microsoft store, and Xbox sales.

Intel

System Validation Engineer
MAY 2006 - SEPT 2008
Santa Clara CA

Hired into the Rotation Engineering Program out of university. Spent my first year rotating between teams before becoming a System Validation Engineer.

Member of a team responsible for functionally validating the Itanium CPU product line. Designed and implemented random instruction test generation software using native assembly, C, and Perl scripts that ran in test labs on hundreds of machines.

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