Shaun is looking for his next role!

I’m a 17-year veteran of the software engineering industry, and I’m seeking a senior technical leadership role. If you have any of the following problems, let’s chat!

  • The way your software engineering organization works feels chaotic
  • Your executives spend too much time solving tactical problems, and not enough time on broader strategy
  • Your organization has grown fast recently, and your ways of working haven’t scaled to succeed with the size of your team
  • Your tech stack hasn’t scaled to handle your traffic volumes and you’re having frequent customer-facing outages

I gravitate toward roles where my core responsibility is to help tech executives scale by solving problems for them. My favorite problems are problems with the following attributes:

  • their impact is company-wide
  • they require evolving your technology to solve for both business and technical objectives
  • they have no solution that appears obvious, or have multiple competing solutions that teams are stuck on deciding between

While I prefer to focus on problems that require evolving your technology, I also like helping executive scale by solving non-technical problems. In the past, I’ve done this by creating mechanisms for yearly planning, roadmap prioritization, critical program and metrics reviews, recruiting pipeline reviews, and budget reviews. I’ve also ghost-written executive-level presentations and reports.

I’m considering both management and individual contributor roles - whichever your organization feels is necessary for me to take on the types of problems described above. In my experience, this type of role is called different things at different companies. If your company is hiring for a role with one of these titles, there’s a great chance I can help!

  • Strategy and Operations Principal
  • Senior Director of Engineering Operations
  • Head of Strategy & Business Operations
  • Chief of Staff
  • Distinguished Technologist
  • Technical Advisor
  • Group Platform Architect
  • Senior Staff Engineer

If you’d like to learn more about me and my preferences for companies and roles, read on! Also, at the end of this page, you’ll find an example of a job posting that I’d be excited to apply for.

// About Shaun Yelle

I have over 17 years of experience in the software development industry. Most recently, I was a combination of chief of staff, technical advisor, voice of the engineer, and technical program management principal and director. Going further back, I’ve been a developer, manager, and director for full-stack software products (both front-end and back-end). I have a background in distributed application optimization, DevOps, SRE, and infrastructure. I have experience scaling systems from thousands to billions of transactions per month. I have worked in companies ranging from startups to industry leaders in several industries: AI-powered SaaS Products, AI-powered Voice Assistants, Video Gaming, and Printing.

// My Ideal Role

Type of Work

As mentioned above, I’ve held several different kinds of roles. I’ve served in this variety of roles because I’m attracted to roles where I’m asked to take on problems that others have struggled with solving.

Generally, the problems I’m given either have no clear cause or there are multiple imperfect solutions. For these types of problems, my role is to:

  • learn about the root causes of the problem, and drive organizational clarity on these causes
  • evaluate solutions, and drive organizational clarity on the tricky trade-offs that make none of them an obvious choice
  • recommend which solution we should move forward with, and why
  • explain what we would need to do as an organization to execute the chosen solution

Once we agree to a solution, I help the organization understand which teams should implement the solution. I then become an executive sponsor and escalation path. In parallel, I move on to the next problem. Some examples of problems I’ve owned:

  • As a chief of staff, I owned key technical, strategic, and organizational mechanisms for orgs of ~1k people. On planning, I have created and orchestrated 3-year-vision setting, yearly planning & funding reviews, ongoing recruiting prioritization reviews, and project funding allocation reviews. I’ve also created, evolved, and orchestrated critical metrics dashboard and reviews, authored quarterly business reports to boards of directors, and prepared presentations whose audiences were both internal and external C-level people.
  • As a technical advisor, I’ve been the executive sponsor for multiple migrations from private to hybrid/public cloud architectures. I developed the strategy for our cloud migration and secured buy-in from all key engineering leaders. This strategy involved identifying which services could simply lift and shift, which ones should replatform, which ones should be rearchitected to take advantage of cloud-native solutions, and which ones should rearchitect ahead of migration to reduce migration risk. I directed effort to define concrete workstreams and reorganize engineering teams to fund this work. I managed risk & escalations, and surfaced important and actionable information to key executives. I also reduced company-wide infrastructure and cloud costs through a combination of re-architecting services, modifying how we use cloud-native services to follow best practices, optimizing our software to use cloud resources more efficiently, and resolving over-provisioning through server consolidation.
  • As a voice of the engineer, I created a principal engineering community and communities of practice. I established and evolved several engineering standards with feedback from the community, including API standards, service launch readiness, and observability best-practices. I built a framework and process whereby any engineer could propose a new standard or process, seek feedback from peers, and ultimately get executive alignment and approval. I also surveyed engineering sentiment and used the results to advocate for and secure funding for our transition to CI/CD, which was considered the single best thing we could do to improve the morale of our engineering community.
  • As a technical program management principal and director, I reduced our high-severity event rate by ~73% (from ~22/month in 2020 to ~6/month in 2022). I did this by taking ownership of a contentious post-mortem process and turning into a mechanism that was blameless and ensured the organization acted on critical findings. I launched several cross-VP programs directly, including Alexa’s Voice Profiles and Automatic Voice Recognition, which enables Alexa to recognize unique voices & personalize her responses based on who is speaking. I managed, mentored, and promoted multiple TPMs. I created training material and taught courses on effective business communication. I created and orchestrated OKR processes and critical risk reviews, which were the mechanisms we used to track status and risk for a portfolio of programs across organizations of over a thousand people.

Location & Work Hours

I strongly prefer fully remote work where I can work during the business day in the US Pacific Time Zone. I am currently based in the Seattle area, and I do not plan to relocate. I will consider in-office roles where my one-way commute is 30 minutes or less.

// My Ideal Employer

Company Size

I’m flexible on company size. I’ve worked in 30-person startups, and I’ve worked in a company with hundreds of thousands of people. That said, I’ve found that my role tends to provide a lot of value for organizations that are growing past a few hundred people, and has an outsized impact in an organization of at least a thousand people.

Company Culture

  • Emotional Intelligence - I prefer organizations that expect people to express their emotions in healthy ways and demonstrate empathy in how they interact with others. This applies all the way up to the C-level. I’ve worked at companies where executives or senior technical ICs joined major incidents and expressed their frustration by yelling at and insulting people who are actively trying to fix the problem. Not only did this behavior slow down our mitigation efforts, but it also created a culture of people who were either afraid to help during the next emergency, or also yelled as a way of trying to get their way. I will never feel comfortable being complicit to that kind of culture.
  • Intent-based Leadership - I believe that the role of senior leadership is to build a combination of strategy and decision-making frameworks that enable anyone to make independent decisions that will naturally align with company objectives. This creates a culture where you create leaders at every level, and those leaders remain happy and engaged in driving the company’s success.
  • Evidence-based Decision-Making & Systems Thinking - Even the most experienced person won’t make the right gut-based decisions all of the time. I think companies perform better when they make decisions based on evidence. Further, I think they perform better when they develop systems that enable them to experiment quickly and collect evidence to validate ideas.
  • Information Flows Freely - I thrive in cultures where information flows like oxygen, not like currency. I believe companies move faster and people make better decisions when they have access to the same information as executives. This means that objectives and key results are communicated regularly, and leadership addresses concerns heads-on instead of avoiding them with vague platitudes.
  • Remote Work & Flexibility - I have a strong bias towards teams that have “re-platformed” successfully for distributed remote work. This usually means that they’ve leaned into asynchronous communication to account for people who work in different time zones on different schedules. I value asynchronous communication and documentation for establishing a shared fact base coupled with judicious use of meetings for deeper reviews and conversations. I also value virtual facetime coupled with occasional “on-sites” for building relationships with team members and stakeholders.
  • Work-Life Balance - I believe it’s possible to do amazing things at a sustainable pace. I stick to a ~40-hour week to avoid burnout, and build an environment where others can do the same.
  • Deeper Focus on Fewer Things - Inevitably, we’ll want to do more than we have the people and time to do. I’ve worked in companies that tried to make progress on tons of things. In these environments, progress felt slow, it felt like we never achieved anything, and team morale was low. I’ve also worked for companies that said ‘no’ to all but a few things, and drove a deep focus on those few things. In these environments, it felt like we were delivering constant wins, and people were excited to move onto the next thing on the list.

Preferred Benefits

Companies that provide the following benefits will be ones I’m more excited to work with.

  • 4-day work week. I know this is rare, but if you offer it, you’ll become a top contender.
  • Fully-remote work and flexible schedules. This is more common, and will also make you a top contender.
  • Medical, Dental, and Vision coverage
  • 20+ days of vacation time
  • 401k match, especially up to the yearly contribution limit
  • Transparency about your total compensation package and target compensation early in the interview process
  • Budget for home office improvements
  • Support for employees using company time and budget to further their professional growth (e.g. achieving certifications relevant to their day-to-day work)


I view the following things as red flags. If these are true of your organization, expect me to probe deeper on the context and how you’re navigating these concerns.

  • Heavy and persistent on-call requirements. I’ve been an incident commander and executive escalation point for major incidents, and am willing to continue to participate in after-hours emergencies. But if getting paged once a week is “normal”, it’s usually a sign that the organization is not prioritizing durable improvements to make their technology more stable.
  • Policies that limit what employees can do with non-work time (e.g. banning open source contributions or side projects unrelated to the business).

// What Your Job Posting Might Look Like

VP of Operations / Technical Advisor to the CEO or CTO

About This Role

Company is seeking a VP of Operations / Technical Advisor to the CEO or CTO. This role is a highly visible role that serves as an executive sponsor, program leader, consultant, and liaison on business and technical initiatives across the company. Through this role, you will help senior executives define and execute on the most important strategic and tactical initiatives at the company.

Successful candidates will have experience with the ways that large companies plan & execute their most important work. Additionally, successful candidates will demonstrate a solid technical and product foundation, and will build on that foundation to develop a broad understanding of how we evolve our products, technology, and business to meet the needs of our customers.

In this role you, will support the company’s executive team by:

  • Owning and orchestrating recurring planning and reporting processes alongside HR & Finance, including defining 3-year visions, yearly roadmap plan, quarterly OKRs, and critical business & metric reviews
  • Attending business, product, program, and technical review meetings to provide feedback, and ask questions on things that stand out
  • Ensuring strong and timely follow-up management on action items and questions
  • Performing ad-hoc deep dives in areas that need closer attention, alongside business and technical owners
  • Providing an independent perspective and acting as a sounding board for ideas
  • Coordinating across organizations to produce consolidated content for presentations to our customers or Board of Directors
  • Drafting and sending company-wide communications

You will support the company as a whole by:

  • Consulting with business owners and support teams looking for 1) feedback on reports before they present to the executive team; 2) advice on thinking through business & technical problems
  • Finding and researching new ideas, directing pilots, and recommending whether further investment is warranted
  • Joining technical emergency response efforts to ensure team have what they need and have a “restore service first” mindset, then summarizing the incident for executives
  • Building our next generation of experts through company-wide training, mentoring, and office hours

Required Qualifications

  • 10+ years of experience working in technical organizations, especially for companies that produce “software-as-a-service”
  • 10+ years of experience managing technical programs

Preferred Qualifications

Ideal candidates will have a successful track record of:

  • Influencing without authority to drive cross-organizational execution
  • Turning ambiguity into short-term actions and long-term recommendations
  • Engaging & communicating with senior executives
  • Communicating clearly, both verbally and in writing
  • Evidence-based decision-making
  • Helping organizations manage through multiple layers
  • Influencing and facilitating decision-making across all aspects of a business, including Sales, Marketing, Product, Engineering, IT, HR, Finance, Legal, and M&A