Director of Web Operations

Hey! You've taken a break from the regular (making things work better for everyone around you) to find something better for you. Pro move. This might be your lucky day.

If your idea of a beautiful moment is a perfectly executed launch, a spotless QA checklist, a color-coded project tracker, and a website that quietly works exactly the way it’s supposed to… keep reading.

We’re looking for the kind of operational leader who notices the missing pixel, catches the broken link before anyone clicks it, and somehow enjoys turning chaos into clean, scalable systems. The kind of person who gets genuine satisfaction from organized workflows, reliable processes, clear ownership, and vendors that actually meet their deadlines.

At Life is Good, our website is one of the most important ways we connect with customers every day. Behind every product launch, promotion, campaign, and smooth customer experience is an operational engine that keeps everything moving. This role leads that engine.

You’ll thrive here if you love creating order without creating bureaucracy, solving problems before they become emergencies, and building systems that help people do their best work. Bonus points if project plans, operational dashboards, and automation opportunities spark the same joy other people reserve for beach vacations.

And yes… once in a great while that means solving a website issue at 8:47 PM while drinking cold coffee and staring heroically into the glowing abyss of browser tabs like a digital air traffic controller for t-shirts. 

Got the vibe? Read on...

Why this job exists

The Director of Web Operations ensures the Life is Good eCommerce platform is always on, always accurate, and always delivering for the customer. This role is the operational backbone of our digital business — owning platform reliability, vendor management, QA, and the day-to-day systems and processes that keep the site running at every layer.

You will manage the ecosystem of third-party platforms, tools, and service providers that power our digital experience, holding partners accountable to SLAs and driving continuous improvement across integrations and operational standards. Working cross-functionally with Engineering, Marketing, Merchandising, IT, Customer Care, and Fulfillment, you ensure that every promotion, product launch, and site update is executed with precision.

Requirements

REQUIRED EXPERIENCE

What you’ll contribute

• You bring knowledge and know-how gained from your 10 years of experience in eCommerce website operations, platform management, or a related technical operations role
• You have direct experience managing eCommerce platforms (e.g., Shopify Plus, Salesforce Commerce Cloud) and the broader ecosystem of integrated third-party tools, apps, and services that support a DTC operation
• You have effectively managed a portfolio of external vendors and technology partners — including contract negotiation, SLA enforcement, and escalation management.
• You are known for your highly effective project management experience, including running complex, cross-functional site initiatives — product launches, platform migrations, and integrations — on time and within budget
• You bring experience gained from owning and managing a web operations budget, including vendor contracts, platform licensing, and technology spend
• You’ve delivered measurable and consistent success in QA — building testing processes, catching errors before they go live, and establishing standards that hold in a fast-moving, frequently updated eCommerce environment
• You’ve experience in site monitoring, performance tooling, and incident response — able to triage issues, coordinate resolution across teams, and communicate clearly under pressure
• You’ve had measurable success in translating technical concepts for non-technical stakeholders and business priorities for engineering and vendor partners
• You are widely recognized for your excellent organizing and process expertise, including documentation, systematizing, and building repeatable workflows rather than solving the same problems over and over

 IMPORTANT DETAILS

• This application requires a significant commitment to answering specific questions. You may want to compose your answers outside of this app and paste them once you're satisfied with your composition, spelling, grammar, and tone. We can't consider incomplete applications.
• Our market-based compensation strategy determines base pay for our jobs. You can use any of the publicly available tools to predict what you might earn here. All permanent roles are eligible for an annual bonus based on company performance, to which you will make a significant contribution.
• This role is based in Boston. You'll work on-site Wednesdays and Thursdays each week.
• Everyone who applies and takes the time to answer our questions will get a response from a human. Although we love and use AI regularly, you're about to put a lot of heart and skill into this application and deserve a human response. You'll get one. If you don't answer the questions or meet the requirements below, you'll get a swift and kind rejection.

Pay Transparency:
We post our jobs on a collection of sites. Not all of them portray accurate information about our compensation ranges. For years, we've used a market-based approach to determine starting pay for all roles at Life is Good. We encourage you to explore reputable salary calculators like Salary.com or PayScale and, using accurate data for the apparel industry, this job (from the job description), our company size (under 300 people), location (Boston), and the required experience for this role (at least 10 years), you will see the pay range for this role.

What you’ll do

• You ensure the eCommerce experience is consistently fast, accurate, and available through responsibility for all day-to-day web operations — site reliability, uptime, platform performance, and incident response
• You own the full ecosystem of third-party vendors, platforms, and technology partners that power the site, managing contracts, SLAs, escalations, and ongoing performance expectations
• You drive the on-time, fully QA’d execution of all site updates, product launches, promotions, and campaigns with a disciplined operational process
• You minimize errors and protect the customer experience through establishing and enforcing quality assurance standards across product content, pricing, promotions, integrations, and site functionality
• You proactively identify and resolve issues before they impact the business by monitoring site health, platform integrations, and system performance
• You build, develop, lead, and mentor a team that performs well together, elevates our culture, and gets the right things done on time
• You effectively manage the operational budget for web technology, balancing cost efficiency with platform reliability and capability needs
• You ensure clean, on-time delivery of the operational workstream for new platform implementations, systems integrations, and technology migrations
• You create consistency, reduce risk, and scale with the business through building and maintaining operational playbooks, governance processes, and standard operating procedures that

How you show up

• You believe in the Life is Good mission and bring that energy to your team and your work
• You lead from the front — a player-coach who rolls up your sleeves and develops the people around you
• You're calm under pressure, clear in your communication, and consistent in how you show up
• You give and receive feedback directly and constructively
• You thrive in a fast-moving environment and can manage multiple priorities without losing the details
• You care about building something — a team, a process, a culture — not just executing tasks

When you’ll know you’re successful

• You and your team meet your annual goals
• The site is reliable, accurate, and operationally sound. Launches go out on time, errors are rare, and issues get resolved fast
• Your vendor partners are performing to expectations and held to clear standards, and your internal partners trust you to get things done without surprises
• Cross-functional teams view you as the operational authority on all things web - the person they come to when something is broken or when they need to know if something is possible
• You have built a team and a set of processes that create consistency, reduce risk, and scale with the business
• Leadership trusts you to represent the brand's operational integrity in every vendor conversation, platform decision, and site experience you own

Benefits

We’re a community of optimists who believe optimism is a powerful way to live and work. We care deeply about creativity, collaboration, authenticity, and making a meaningful impact through the work we do together.

We’re not interested in building a culture where people simply “fit in.” We want people who elevate the work, challenge stale thinking, improve the experience for others, and help move the business forward.

We are located in the innovative and thriving Fort Point neighborhood. Our community is full of green space, outstanding food, and entertainment options. We offer top quality Medical, Dental, Vision, Flexible Spending Accounts, Transit or Parking Reimbursement Accounts, Life, AD&D, Short and Long-Term Disability, 401(k) with a match, Paid Time off, 10 paid holidays, Good Vibes Time (we pay you to volunteer for the non-profit cause of your choice) and Family Time. And we have dogs. You’ll be involved in growing our social mission through the Playmaker Project.

Life is Good is an equal opportunity employer and does not discriminate against otherwise qualified applicants on the basis of race, color, religion, national origin, ancestry, sex, age, mental or physical disability, pregnancy, sexual orientation, gender orientation or expression, marital status or veteran status, or any other legally protected characteristic under applicable federal or state law.