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About Trellis
Trellis is a profitable, Series A start-up backed by leading VC's like General Catalyst, QED, NYCA, and Amex Ventures. We are on a mission to simplify and automate big financial decisions for Americans, starting with home and auto insurance. Nearly ten thousand Americans shop for home and auto insurance on our platform every day. Our unique technology and talented service team enables these customers to make better decisions, more quickly and effortlessly, than anywhere else.

Your Mission
Reporting to the CEO, the Head of Engineering will play two key roles:

1. Chief Architect - We operate a very complicated product with over $100k of daily transaction activity. We need the Head of Engineering to "see around corners" to ensure that well-intended changes don't break things downstream. Relatedly, we need the Head of Engineering to ensure that our system is built and refactored in a way that preserves maintainability, availability, and extensibility - such as by exercising clean domain-based modeling!

2. Engineering Manager, Leader, and Coach - We have a small but amazingly-talented, and very experienced team of about 6 engineers. The Head of Engineering will manage all of them and will add 1-2 more senior engineers as quickly as possible!

Your Goals

1. High Product Availability

• E.g. less than 3% of revenue is lost to bugs, regressions, outages, etc. This will require a deep understanding of our systems, our workflows, and our stakeholders' needs
• This may require spending probably 20% of your time on code review
• This will likely require spending 20-30% of your time on authoring tech plans and crystal clear tickets to ensure ambiguity does not cause unintended consequences
• This will require a healthy amount of "on-call" availability, which you can delegate out to the team as reasonable, so long as you remain the final point of escalation
• The institutional knowledge exists in the company currently, so you would spend the first 30 days on an accelerated learning curve picking it all up
• You may find yourself spending 10-20% of your time building dashboards and monitoring of new and existing systems and workflows

2. Motivated Team

• High performers retained
• Strong engagement survey results from your team
• 1-2 new senior IC hires made within 2-3 months and ramped up to a high level of performance within 4-6 weeks

3. High Engineering Responsiveness to "Chores"

• Insurance marketing is a surprisingly dynamic and fast-paced world. Insurers are constantly updating their rates and underwriting guidelines, and our top-of-funnel marketing is constantly evolving in terms of channels and their quality.
• Our product often needs to respond quickly to these contextual changes, such as by plumbing a new feature into a production machine learning model, or by adding a question into our workflow.

4. Reasonable Feature Velocity

• We're generally optimizing our pace with an eye toward 12-month ROI.
• The Head of Engineering will help us avoid jumping into "chutes" and instead land us on the "ladders" – such as by ensuring that experiments are QA'd prior to a full 50/50 launch, so that we don't spend 2 weeks collecting data with a buggy experiment.

5. Good (if not Great) Predictability

As a multi-sided marketplace with large partners, and an operations team as part of the equation, predictability creates value for our ecosystem by building trust and delivering better ROI on our partners' investments into using our platform. The Head of Engineering will properly forecast engineering availability, accurately estimate the time and effort required to complete small and medium projects, and vigilantly monitor progress in order to concisely, promptly, and articulately update stakeholders about meaningful changes in timeline or status.

What You'll Need to Succeed

1. Experience in Complex Product Domains

From a raw technical perspective, our product is not rocket science. But the technicalities of our product domain are complicated and critical. Moreover, we do not enjoy a terrible number of natural abstraction boundaries because of the messy context inherent to heavily-personalized experiences. Consequently, changes anywhere in the system (or even in our partners' systems') can break any number of things anywhere downstream. Adding even more fun to the mix, sometimes the changes that break things are fully opaque to us (such as insurers' changing bids in their real-time models, or partners' changing the audiences of their email marketing). We need someone who can understand the fullness of our complicated product network in order to properly triage and/or help resolve issues, and to identify latent opportunities.

2. Backend Orientation

Our frontend is complex, but our backend is even more complex. We need someone very comfortable with designing good, easy-to-use API's, that will easily extend to future use cases, for example.

3. Organization

Our team manages an incredibly wide surface area of software. Keeping tabs on everything requires the design and execution of systems and processes.

4. Motivational and Positive Attitude

As the sole people and hiring manager on the engineering team, building trust, respect, and rapport with staff, stakeholders, and prospective new hires will be essential.

5. Comfort with Numbers

By and large, our partners measure our success on a single, easy-to-measure metric: profit. Consequently, we focus a lot on driving numbers to where they can be and where they need to be. We need someone familiar with at least the basics of good experimentation, and an ability to ensure that when we analyze a problem or a question that we're looking at "the right numbers the right way".

6. A Brisk Pace

We don't need a "pre-seed" sprinter/prototyper, but we also can't operate like FAANG molasses. We need a strong context switcher who can quickly ramp on new types of problems, think on their feet, bias toward action, and avoid letting perfect be the enemy of the good.