Senior Director of Engineering

The Senior Director of Engineering is the senior-most day-to-day engineering leader at Cooper's Hawk and will play a critical role in stabilizing, modernizing, and accelerating delivery across the company's guest-facing digital properties, Wine Club, and enterprise application platforms. This role leads two portfolios: Guest-Facing Digital, which covers the company's seven websites and mobile experiences, and Platform Systems, which covers Salesforce, Wings, the Wine Club subscription automation server, the Enterprise Service Layer, and other supporting enterprise applications. The role exists to bring technical leadership, engineering discipline, and delivery momentum to an environment that has grown quickly, accumulated technical debt, and now needs to scale responsibly without losing the ability to move fast. Reporting to the VP of Digital and Restaurant Applications, this leader will guide a lean internal team and multiple external development partners across Salesforce, web, mobile, e-commerce, vendor-hosted applications, and integrations. They will stabilize legacy systems, remediate risk, and unlock new feature development that improves the guest and member experience and supports the business' next phase of growth. This is a true player-coach role. We are looking for a leader with deep engineering and architecture expertise who will set technical direction, design solutions, and get into the code when needed, while also building and developing the team. The right person is comfortable operating in scrappy, resource-constrained environments, can make pragmatic trade-offs, and understands how to balance speed, stability, and audit readiness. Scope of Role This leader directly manages a small internal team that spans both portfolios and is supported by multiple external development partners. There are no intermediate management layers, so the role combines people leadership with hands-on technical ownership. Guest-Facing Digital The Guest-Facing Digital portfolio covers the digital properties that guests and Wine Club members use to discover our brands, order, and manage their memberships. Delivery is primarily outsourced to external partners, with internal support from a full-stack developer and a Business Analyst / Product Owner. The portfolio includes: - Cooper's Hawk brand website - Piccolo Buco brand website - Cooper's Hawk and Piccolo Buco Carryout ordering sites - Wine Club Member Portal - Mobile app - Retail e-commerce site (Shopify) These properties are supported by multiple external development partners, which makes clear ownership, coordination, and technical oversight essential. Platform Systems The Platform Systems portfolio covers the core systems behind Wine Club and enterprise operations. It is supported internally by Salesforce Engineers, a Salesforce System Administrator, and application engineers. The portfolio includes: - Salesforce (Service Cloud), the core platform for Wine Club, including Apex code, triggers, APIs, and integrations. - Wings, a custom C# application used in our restaurants to support Wine Club sign-up, updates to member information, and visibility into member entitlements. - The Wine Club subscription automation server, which supports automated processing for Wine Club subscriptions. - The Enterprise Service Layer, the integration layer that provides shared services and connects core systems with our digital channels and other applications. - Additional enterprise and custom applications. How You Will Succeed: Engineering Leadership & Team Enablement - Serve as the technical leader for all engineering efforts across Guest-Facing Digital (brand websites, Carryout sites, Member Portal, mobile app, and retail) and Platform Systems (Salesforce, Wings, the subscription automation server, the Enterprise Service Layer, and custom applications). - Directly lead the internal team, including Salesforce engineers and administration, application and full-stack engineers, and business analysis / product support, setting clear goals, priorities, and accountability. - Provide hands-on guidance to developers through design reviews, code reviews, pairing, and technical decision-making. - Establish clear engineering standards and expectations across stacks while avoiding unnecessary process overhead. - Coach and mentor developers to improve technical capability, confidence, and execution quality. - Act as the escalation point for complex technical issues and architectural decisions. Architecture & Hands-On Engineering - Own the end-to-end technical architecture across guest-facing digital and platform systems, including how websites, the mobile app, Salesforce, Wings, and other applications integrate through the Enterprise Service Layer and share data. - Define a pragmatic target-state architecture and roadmap that reduces complexity, eliminates fragile point-to-point integrations, and supports future growth. - Set standards for APIs, integration patterns, data flows, security, and environment strategy across internal and partner-built solutions. - Mentor engineers and vendors on the most critical work, such as prototyping, complex integrations, performance problems, and difficult production issues. - Make and document key architectural decisions, and ensure partners build to the agreed architecture rather than around it. Platform Stabilization & Risk Reduction - Assess and prioritize remediation of technical debt, vulnerabilities, and fragile components across the application ecosystem. - Lead stabilization of the brand and Carryout websites, mobile app, Member Portal, and Wine Club integrations, including Salesforce Service Cloud Apex code, triggers, and APIs. - Own the health and supportability of in-restaurant Wine Club capabilities, including member sign-up, updates to member information, and visibility into entitlements, driving enhancements, defect resolution, and roadmap so these work reliably for restaurant teams and guests, and guiding any future platform changes. - Ensure the Wine Club subscription automation server and Enterprise Service Layer are reliable, monitored, and well documented, given their central role in Wine Club operations. - Maintain Salesforce org health through sound administration, configuration, and deployment practices, including environment management and change controls. - Design and implement effective release and vulnerability management tech solutions. - Partner with Infrastructure, Security, and Data leaders to ensure systems are reliable, observable, and supportable. - Participate in incidents as necessary and drive root-cause analysis and permanent fixes for recurring production issues. Delivery, Features & Member Experience - Enable faster, more predictable delivery of new features and enhancements across guest-facing digital, Wine Club, and platform systems. - Ensure a consistent, connected Wine Club member experience across restaurants (Wings), the Member Portal, the mobile app, and Salesforce. - Identify and unlock "low-hanging fruit" and quick wins that improve guest and member experience and business outcomes. - Partner closely with Product, Marketing, Restaurant Operations, and other business stakeholders to ensure solutions meet real needs and work reliably. - Ensure engineering teams can deliver incrementally without destabilizing the platform. - Balance stabilization work with forward-looking development, not one at the expense of the other. Vendor & Partner Leadership - Lead and hold accountable all engineering partners and application vendors (onshore and offshore), including the multiple development partners supporting our digital properties and the vendors behind our SaaS and third-party platforms. - Define clear ownership and coordination where multiple partners support the same applications, avoiding gaps, overlap, and finger-pointing. - Manage partner statements of work, budgets, and performance against service levels, in partnership with IT leadership and Procurement. - Establish clear expectations for code quality, documentation, testing, and delivery outcomes. - Review and approve vendor-delivered architecture and code to ensure maintainability and scalability. - Reduce reliance on heroics and tribal knowledge by improving standards and knowledge transfer, and ensure critical system knowledge is retained internally rather than with any single partner. Ways of Working, Quality & Controls - Establish pragmatic engineering and delivery practices that support speed and reliability. - Ensure quality is built into releases through clear acceptance criteria, testing expectations, and release readiness standards. - Partner with leadership to support audit, ITGC, and SOX requirements. - Improve documentation, change traceability, and repeatability where it matters most. - Help transition the organization from ad hoc delivery to disciplined execution while preserving agility. Strategy & Leadership Partnership - Partner closely with the VP of Digital and Restaurant Applications and IT Leadership on engineering strategy, sequencing, and trade-offs. - Provide clear, honest assessments of technical risk, capacity, and feasibility. - Help shape the future engineering organization, including roles, capabilities, and the right balance of internal talent and managed services. - Represent Engineering in cross-functional discussions with confidence and credibility. What You'll Bring: Experience & Qualifications - 10+ years of software engineering experience, including significant time in hands-on technical roles. - 5+ years leading engineering teams in complex, multi-system environments, ideally in a player-coach capacity. - 5+ years of software or solution architecture experience, including APIs, integration patterns, cloud platforms, and data flows across SaaS and custom applications. - Currently or recently hands-on, with the ability to write, review, and debug production code alongside the team. - Demonstrated experience stabilizing legacy platforms while continuing to deliver new features. - Strong hands-on background in at least one modern programming ecosystem and the ability to guide work across multiple stacks (C#/.NET, React, Salesforce Apex, web, mobile, APIs, integrations). - Working knowledge of Salesforce (Service Cloud, Apex, integrations) and familiarity with Salesforce administration and DevOps practices. - Experience delivering and supporting consumer-facing websites, e-commerce and online ordering platforms (Shopify or Olo experience a plus), and mobile apps, including app store release management. - Experience managing vendor-hosted or SaaS applications and their integrations with core systems. - Proven success leading primarily outsourced delivery models with multiple partners, including managing statements of work, service levels, and vendor performance. - Comfort operating in environments with limited structure, tight budgets, and evolving priorities. - Experience in consumer-facing, subscription, loyalty or membership, retail, restaurant, or hospitality environments strongly preferred. Skills & Attributes - True player-coach who is equally comfortable in the code and leading people. - Credible, hands-on technical leader and architect whom developers respect and trust. - Firm but fair partner manager who holds vendors accountable while building productive relationships. - Pragmatic problem solver who values progress over perfection. - Comfortable making trade-offs and sequencing work under real-world constraints. - Clear communicator who can explain technical concepts to non-technical leaders. - Calm under pressure; able to lead through ambiguity and change. - Strong sense of ownership and bias toward action and continuous improvement. Compensation Range: $180,000 - $220,000 + bonus potential. The final offered salary will be based on several factors, including but not limited to the candidate's depth of experien