Senior Director, Software Development

Lightspeed Commerce, Inc.•New York, NY

2d•$260,000 - $290,000•Hybrid

About The Position

As Senior Director, Engineering – Retail, you will lead the engineering organization responsible for Lightspeedʼs Wholesale and Golf businesses. You will shape the technical strategy, operating model, and culture that enable these teams to deliver meaningful outcomes for merchants. This is a broad leadership role. You will connect business strategy to product and engineering execution, guide architectural choices, strengthen product quality, and develop the leaders who make the organization successful. You will partner closely with Product, Design, Go-to-Market, and senior company leaders to make clear decisions and deliver with focus.

Requirements

Significant experience leading engineering organizations through managers and senior technical leaders.
A track record of connecting engineering strategy to business performance and customer value.
Experience guiding complex product and platform development across multiple teams.
Strong technical judgment, with the ability to engage deeply in architecture, reliability, quality, and long-term maintainability.
Experience improving delivery flow while preserving engineering standards and sustainable pace.
A practical approach to operating in ambiguity: you create clarity, make decisions, and adjust as new information emerges.
Strong partnership skills across Product, Design, Operations, Sales, and customer-facing teams.
The ability to attract, develop, and retain high-performing leaders in a distributed organization.
Clear, concise communication and the confidence to work with senior executives.
A genuine focus on customers and the merchants who rely on our products every day.

Nice To Haves

Experience in retail technology, wholesale, golf, commerce, SaaS, or another domain with complex operational workflows.
Experience leading teams responsible for transactional, scheduling, inventory, payments, or other business-critical systems.
Experience integrating product teams with shared platforms and services.
Experience leading organizational change while maintaining delivery momentum.

Responsibilities

Set the engineering strategy for Wholesale and Golf, translating business priorities into clear technical direction and actionable plans.
Lead and develop a multi-team organization through strong managers and senior technical leaders.
Partner with Product and Design to establish priorities, clarify trade-offs, and deliver customer outcomes.
Improve the health of the engineering system through effective planning, delivery practices, quality standards, and operational discipline.
Raise the reliability of critical merchant workflows by strengthening ownership, observability, incident learning, and risk management.
Guide architecture and platform investments that improve product coherence, reduce unnecessary complexity, and increase team leverage.
Create an environment where teams can move quickly without compromising technical integrity or customer trust.
Build strong relationships across Retail and the wider company, bringing the right people together around difficult decisions.
Hire, coach, and retain exceptional leaders and engineers; create opportunities for people to grow and do their best work.
Communicate progress, risks, and decisions with clarity at the team, executive, and cross-functional levels.

Benefits

Flexible work environment
Culture that celebrates performance
Career-defining opportunities
Flexible paid time off and remote work policies
Equity options
Contributions to your pension plan
Training opportunities to grow your skills and career
Health and wellness credit
Time off to volunteer and give back to your community
Interest groups, employee led networks, social committees to sponsored sports teams
Computer purchase program
Enhanced parental leave
Medical insurance
Dental insurance
Wellness insurance
Life insurance
Disability insurance
401K plan and match