Head of Engineering

About GiddyUp GiddyUp is a performance-based Partner Marketing Platform and Agency that’s generated over $1.5B in sales for innovative DTC brands—without raising a dollar of VC funding.  Founded in 2013, we’ve been bootstrapped and profitable since day one, and our entire model is built around one thing: we only get paid when we deliver results.  We combine elite strategy, creative, media, and analytics under one roof, supported by our proprietary funnel-building and e-commerce checkout software, engineered specifically for high-converting, scalable direct response. It’s not just best-in-class, it’s the backbone behind dozens of 7, 8, and 9-figure DTC offers.  We’re an agile, tight-knit team of marketers, creatives, data analysts, and operators who are obsessed with winning. Every person here is driven to push boundaries, test relentlessly, and grow because at GiddyUp, standing still isn’t an option. If you're looking to join a company where performance isn’t a department… it’s the culture, this is that place. About The Role:  As the Head of Engineering, you will lead and develop our platform engineering team to execute on GiddyUp’s technical strategy. You will be at the forefront of our technical vision, leading a team of engineers to develop, implement, and refine our platform, product, and services for our customers.  We’re looking for an experienced engineering leader to leverage the latest technologies in order to overcome a variety of data and engineering challenges – and deliver meaningful results. This is an excellent opportunity for a candidate looking to push themselves in a startup environment and make a difference in the e-commerce space. You will be responsible for nurturing engineers’ career growth, creating a positive and supportive engineering culture, offering architectural and design guidance in all engineering matters, defining and shaping our technical strategy and roadmap, leading the charge on how we incorporate AI into our engineering practices, and collaborating with product, QA, and data to help execute on the product road map and ensure successful delivery of our product without compromising on quality. The person in this role will remain hands-on and empower the team to advance and accomplish our ambitious technical roadmap.  This role demands someone who is articulate and is comfortable working closely with business stakeholders at all levels to ensure that the solution identified is fully understood and aligned with GiddyUp’s business needs.  What You’ll Do:

Lead a team of talented backend and frontend engineers who like to ship code and tackle hard engineering problems

Be hands on, contribute to the codebase and problem-solve with your team 

Collaborate with Product to scope new features and develop technical solutions to ensure effective and efficient delivery 

Maintain a balance between building sustainable, high-impact projects and shipping things quickly

Instill a spirit of continuous improvement in the team’s code, architecture, and processes

Own your team’s deliverables and ensure we continue to ship scalable, highly-available products that delight our users

Collaborate with external engineering vendors and stakeholders

Work closely with our external CMS development team to get a comprehensive knowledge of the platform and support the team as needed

Drive technical excellence through code quality standards, scalability, observability, and performance optimization.

Responsible for managing the engineering budget including technology stack, full-time resources and external resources  

Introduce AI-powered and similar tools to improve team efficiency and maximize velocity

Leverage your technical background to directly benefit the team, lead by example when faced with challenging problems, and encourage technical discussions to help the team reach a consensus

Mentor and guide the professional and technical development of your team members,  help develop their careers, and assign them to projects tailored to their skill levels, personalities, work styles, and professional goals

Build teams that are collaborative, inclusive, and respectful of each other

Work closely with HR to recruit and hire high caliber candidates from diverse backgrounds; meet with job candidates; evaluate technical screenings, find the right engineers to further build out our team

Collaborate closely with upper management and leadership to ensure the wellbeing of your department and the alignment with the company culture and goals

Own the platform infrastructure and ensure the platform scales appropriately during high load periods

Responsible for ensuring the platform stays up-to-date and standard maintenance is completed

Working knowledge of Data Privacy and Compliance standards and the implication on features being developed

Ensure platform has adequate performance testing on both the backend and frontend

Co-own scrum, sprint planning, daily stand-ups, retros, backlog grooming with product 

Create plans for prioritizing technical and resourcing challenges with the engineering organization

Own all technical documentation, architecture diagrams, domain models, workflows (Git-based), and release pipelines

Effectively project manage engineering work to ensure the engineering team does not create roadblocks on cross departmental projects 

Communicate and collaborate with other managers, stakeholders and contractors

Keep upper management in the loop to ensure they can make informed decisions regarding the business and the team 

Competencies:

Collaboration & Teamwork: works collaboratively with managers, colleagues, and external stakeholders to achieve identified goals and objectives; works to create alignment across teams.; Is consistent, predictable, and easy to work with

Communication: conveys information in a clear, accurate, and appropriate way in verbal and written communications; considers tone, attitude, and intention when communicating with a coworker, group or external stakeholder; acknowledges that one’s experience and opinion is one’s own

Ownership: takes ownership of work, projects, challenges and outcomes; fulfills commitments and addresses blockers; Is self-directed and consistent in meeting job requirements and objectives  

Technological Fluency: is proficient in the use of work-related software, technology, and tools required to perform one or more of the responsibilities related to one’s role; stays up to speed on new technologies and leverages technology to increase productivity and efficiency

Decision Making: resolves issues within the team and makes meaningful decisions quickly; values “progress over perfection” and ensures the team is unblocked and able to make constant progress

Business Perspective: has a deep understanding of both how GiddyUp functions and how our stakeholders operate; has the ability to apply appropriate advising to help our organization and all stakeholders achieve desired outcomes

Managing Resources: evaluates, identifies, and leverages team members’ key strengths, develops areas of improvement, conducts ongoing performance management and guides professional growth; sets team priorities in line with company goals and manages the activities of one’s team accordingly

Adaptability: ability to meet the changing technical landscape, continually evolve skills, learn new technologies, and embrace new development processes

Software Development: the ability  to plan, design, create, amend, verify, test and document new and amended software components in order to deliver agreed value to stakeholders

Velocity: the number of story points an employee achieves each sprint 

What Success Looks Like Over the Next 6 Months:

What you will have accomplished 30 days in: 

Have a deep understanding of our engineers, their skill sets and their professional goals

Have a deep understanding of our business model, key components of our platform and successfully pushed code into Production

What you will have accomplished 90 days in: 

Have a comprehensive understanding of our platform and provide an audit report on platform health, tooling enhancement recommendations, cost optimization opportunities, and security

Provide a plan that Identifies resource gaps and future resource needs 

Increase velocity, ensure proper scoping, reduce number of bugs, challenge product epics to ensure engineering has properly scoped work assignments

Be self-sufficient in providing recurring updates to leadership

Take ownership of the external agency relationships

What you will have accomplished 6 months in: 

Complete a comprehensive architectural map of our platform

Materially improve GiddyUp’s engineering culture and create a collaborative and safe environment for our engineers to learn, grow and deliver in

Fully own all engineering work product and take responsibility for the outcomes of the engineering department 

Tools & Technology:

Frontend - HTML5, CSS3, JavaScript, Tailwind CSS, VueJS, CraftCMS

CDN - Fastly, Cloudflare

Backend - PHP, Laravel, ReactJS, Django CMS, Swagger

System monitoring tools - DataDog, Sentry, Circle CI, Cypress, TestNG, Selenium WebDriver managed by Selenoid, RestAssured, Allure

Collaboration Tools - Slack, Zoom, Google Suite, Jira

Payment gateways - Stripe, PayPal, QBO, etc. 

Platform Infrastructure - Cloudfront, Cloudformation, RDS, ECS, EKS

Data Infrastructure - AWS S3, Snowflake, Rivery, ETL and reporting tools

Ad Platforms / Pixel Tracking - Meta, Google, Taboola, OutBrain, TikTok

Feature Flagging - Statsig

Analytics Tools - Mixpanel, Rudderstack, Retool, Google Analytics, 

Task/workflow management tools - Confluence, Linear and Jira

AI Coding Tools - Cursor, GitHub Copilot

Wireframing/Prototyping tools such as Miro and Figma

Understanding of coding standards and documentation

Understanding of Github and Postman

Required Education & Experience:

Bachelor's or Master’s degree in Computer Science or related field

10+ years experience and 4+ years leadership experience (CTO, VP Eng, Sr Director) at a startup or established company, preferably during the team and business scaling phase

Full stack proficiency, 10+ years of total engineering experience, with deep hands-on expertise across both backend and frontend technologies

Enterprise platform ownership experience, 3-5+ years in a leadership or principal engineering role directly responsible for the delivery, maintenance, and evolution of an enterprise-grade software platform. 

Been the primary stakeholder through multiple full product lifecycles (from initial architecture through scaling, maintenance, and modernization).

Highly technical with expertise in infrastructure, architecture, mobile development, and devops. Strong passion for the craft of engineering.

You’ve led a high performance engineering team from a small team to a medium  department (5 to ~15) You have experience hiring, onboarding, and developing excellent engineers - this is core to the job

Your background as an engineer makes you credible to your reports

You have a proven track record in overseeing the development and delivery of high-quality software and services

You take full accountability for achieving company objectives and inspire your team to deliver

You make tough decisions, leveraging both data and intuition

You have strong outcome-orientation and delivery-focus, while keeping an eye on long-term priorities and making reasonable decisions on when to prioritize speed of delivery over longer term goals

You’re comfortable managing/working with a team in a hybrid environment

You are a strategic thinker, have experience building high-performance teams at pace in a start-up environment

Direct experience working on a two-sided platform or marketplace is a must

Preferred Education & Experience:

Advanced degree in Computer Science or related field is a plus

Stats and/or Analytics Background

Experience working in a startup environment

AI/ML background a plus

Experience working strategically with data and product teams 

Platform development experience