Director, Engineering

Sunday
Director of Engineering
Full-time · Reports to CEO/Leadership Team · Boulder, CO or Remote

About the Role

Sunday is looking for a Director of Engineering to lead and elevate a talented, close-knit engineering team through a pivotal moment. We're building something novel in the lawn care category, not reinventing an existing category, and our engineers are energized by that focus. This role exists to protect and grow that momentum: setting technical vision, building org-level capability, and bringing in an AI focus.
This is a hands-on leadership role with real strategic ownership. You'll need to be credible in the weeds, able to understand what's happening in the codebase and the business, while also sitting close to company leadership, translating company vision into an engineering roadmap, and making the structural calls the team doesn't have bandwidth to make themselves.
Above all, we need a builder. Someone who gets genuinely excited about writing code and shipping products, not solely a people manager. You'll rally the team by being in it with them, and you'll partner directly with Product as a true collaborator, not an order-taker: we need someone who understands how product and engineering decisions shape each other.

Vision & Strategy

• Develop a technical vision for engineering that ties directly to Sunday's business goals, and translate it into a 6–12 month roadmap built with Product and the Leadership Team
• Build and own Sunday's AI strategy for engineering, establish a consistent approach to AI-assisted and agentic development, and use it to help the team move faster and fail faster
• Serve as the connective layer between business/product priorities and the engineering team

AI-Native Product Direction

• Push Sunday toward becoming a genuinely AI-native product company, not a deterministic product with a chatbot bolted on, but one where core functionality is LLM-driven where it makes sense
• Bring real excitement and a point of view about this shift, and get the team energized about building toward it together
• Support early agent-based project work and help set a broader, more consistent direction for how the team builds and evaluates agentic systems
• Establish evaluation practices (evals) for AI-driven functionality; fluency with eval tooling (e.g., Braintrust, Langfuse, or similar) is a strong plus, since non-deterministic, LLM-driven logic can't be tested the way traditional deterministic code is

Technical Maturity & Architecture

• Bring maturity to foundational infrastructure and architecture decisions
• Identify and invest in the technical decisions that save the team time now, rather than accumulating further shortcuts
• Bring a builder's mindset to this work personally; this isn't a hands-off architecture review function; it's active, credible participation in solving it

Org Building & Talent

• Own hiring strategy and interview process for both ICs and future managers, partnering closely with the People team; instill and maintain a high hiring bar
• Prevent single points of failure, put institutional knowledge, documentation, and cross-training in place
• Give engineers real paths to grow, including mentorship, stretch opportunities, and regular, honest development feedback

Execution & Delivery

• Hold the team accountable to its own goals; regularly evaluate team structure and workflow to keep the org moving quickly
• Codify and disseminate engineering best practices, testing, code review, PR norms, and how those practices scale as AI-assisted development increases velocity, so speed doesn't outpace quality
• Own engineering metrics — delivery against roadmap, quality/bug backlog, system performance and uptime, and team velocity, and use them to surface bottlenecks to leadership
• Deliver honest, frequent, and respectful feedback, and build a culture where the team gives and receives it the same way

Cross-Functional Leadership & Product Partnership

• Represent engineering as part of company leadership, communicate plans, tradeoffs, and challenges to other functional heads in terms the whole business can act on
• Act as a true product partner given how much of Sunday's product is (and will increasingly be) LLM-driven; engineering and product decisions are directly intertwined, not sequential handoffs
• Understand how product thinks, and bring engineering's perspective into product conversations early — this is a collaboration, not a request queue

What Success Looks Like

• The team feels led, not managed, with clear priorities, cleared blockers, and visible follow-through
• Strong opinions, held loosely: you set direction but trust engineers to own execution
• The team has real conviction that engineering is heading in the right direction
• A working AI strategy the whole team is aligned on, with visible gains in velocity and quality

What You Bring

• Proven experience leading engineering at a small-to-mid-size or growth-stage company, with a track record of taking on increasing scope
• A genuine builder, you want to be hands-on writing code and shaping product, not solely managing people and process
• Strong individual technical credibility — you can go deep enough to earn trust with senior engineers, not just manage from a distance
• Direct experience with, or strong enthusiasm for, AI-native product development — building products where core functionality is LLM-driven rather than deterministic, not just adding an AI chat feature to an existing product
• Familiarity with LLM evaluation practices and tooling (Braintrust, Langfuse, or similar), given the shift toward non-deterministic, AI-driven functionality
• Front-end depth, or demonstrated ability to grow it across a team
• Hands-on familiarity with AI-assisted and agentic development workflows, and a clear point of view on how to scale them responsibly
• A naturally curious, learning-oriented mindset, hungry to keep growing and to bring the team along with you
• Experience building org structure, hiring processes, and team practices from a lighter-weight or informal state
• A true product-collaboration mindset: understands how product and engineering decisions shape each other, and doesn't need — or want — a roadmap simply handed to them
• A business-minded, collaborative style, comfortable building relationships across the whole company, not just within engineering
• Humility and directness, able to talk openly about mistakes and how they were resolved, and to give feedback as a gift
• A communicator who can move fluidly between technical depth and company-wide clarity

A Note on Team Culture

Sunday's engineering team values being in the weeds together, moving quickly, and staying focused on one clear, differentiated product direction. We're looking for a leader who amplifies that — someone the team describes the way they describe their best examples of leadership: present, communicative, and unafraid to tackle the hard stuff directly.

As a company rooted in nature, we deeply understand the benefits of diversity. We work to build a culture that attracts a diverse mix of talented people to help us bring lawn care out of the dark ages. We are committed to building a diverse, vibrant team that brings determination and passion to our work everyday.

Originally posted on Himalayas