Jobs · Engineering · New York

Senior Director, Software Development

Lightspeed Commerce · New York, NY · 3 wk ago
HybridEngineering$260k–$290k/yrPart-time
We need to output HTML fragment with sections for headings: About the role, Responsibilities, Requirements, Qualifications, Skills, Benefits, Pay, Schedule. Only include sections that have real specific content. We must not repeat job title as heading. No Job ID etc. Remove boilerplate, navigation, legal, EEO, etc. Also remove application instructions, duplicated lines. Keep substantive info. We need to parse the posting. Let's extract sections: - Intro: "Hi there! Thanks for stopping by 👋 We’re looking for a Senior Director, Software Development to join our Retail team in Canada or USA. 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." That's about the role. Could be "About the role". - "What You’ll Be Doing" list: bullet points. - "What You Need To Bring": list. - "Nice to have": list. - "Be a changemaker You’ll Enjoy": bullet list of benefits: flexible work environment, culture, chance to make impact, career-defining opportunities, plus benefits designed to keep you happy, healthy and fulfilled. Then list: Flexible paid time off and remote work policies, Equity options, Contributions to your pension plan, Training opportunities, Health and wellness credit, Time off to volunteer, Interest groups..., Computer purchase program, Enhanced parental leave. - Then "Fuel your growth..." paragraph about learning opportunities, global mobility, benefits. - Then "Please note that we ask applicants to disclose any criminal convictions..." that's legal boilerplate; remove. - Then compensation: "At Lightspeed, we carefully consider a wide range of factors when determining compensation... We reasonably expect the base salary for this position to be in the range of $260,000 to $290,000 USD, depending on the candidate’s location. Additionally, this role may be eligible for discretionary short-term and long-term incentives. Lightspeed also provides a variety of employee benefits including, but not limited to, medical, dental, wellness, life and disability insurance, 401K plan and match, paid parental leave top-up, and paid time off." Also note about US only etc. We need Pay section if specific salary range given. Yes we have salary range. So include Pay section with that info. Also benefits already covered; but we can still include Benefits section with details (flexible PTO, equity, pension, training, health wellness credit, volunteer time, interest groups, computer purchase, enhanced parental leave, medical/dental etc). However we must avoid duplication. We can combine benefits in Benefits section. Pay section separate. - Schedule: Not mentioned explicitly; maybe flexible work environment implies remote/flexible but not explicit schedule. No explicit schedule info. So we should not create Schedule section. - Qualifications vs Requirements vs Skills: The posting has "What You Need To Bring" (requirements) and "Nice to have" (preferred). Could map Requirements to "What You Need To Bring". Skills maybe separate? Could treat "What You Need To Bring" as Requirements. "Nice to have" as Qualifications or Skills? Usually Qualifications are required; Skills maybe separate. But we can just have Requirements and maybe Skills (if we want). However we must not create thin sections. Better to have Requirements (What You Need To Bring) and maybe Skills (Nice to have) as Skills. Or combine into Requirements and Qualifications. Let's decide: Use Requirements for mandatory, Qualifications for nice-to-have. Or Skills for nice-to-have. The instruction: Use headings for section headings (e.g. About the role, Responsibilities, Requirements, Qualifications, Skills, Benefits, Pay, Schedule). So we can include Requirements and Qualifications. We'll put "What You Need To Bring" under Requirements. "Nice to have" under Qualifications. Skills maybe not needed; we could omit if no specific skills list separate. But we could put technical judgment etc under Skills? However those are in Requirements. Better to keep Requirements and Qualifications. Thus sections: - About the role (intro paragraph) - Responsibilities (What You’ll Be Doing) - Requirements (What You Need To Bring) - Qualifications (Nice to have) - Benefits (Be a changemaker You’ll Enjoy + benefits list + additional benefits from compensation paragraph) - Pay (salary range and incentives) We must not include Schedule. We must preserve all substantive info, not invent or summarize away detail. Must not include filler like "commensurate with experience". Not present. We need to output HTML fragment only, using

for headings,
  • for lists,

    for prose. We must not repeat job title as heading. We must not include boilerplate like EEO, criminal convictions, etc. We must remove duplicated lines. Let's extract precise content. First, About the role paragraph: combine the intro sentences. Original: "Hi there! Thanks for stopping by 👋 We’re looking for a Senior Director, Software Development to join our Retail team in Canada or USA. 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." We can keep that as a paragraph. Second, Responsibilities: list bullet points from "What You’ll Be Doing". Let's copy each bullet: - 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. We'll put each as

  • . Third, Requirements: "What You Need To Bring" list: - 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. We'll put as list. Fourth, Qualifications: "Nice to have" list: - 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. We'll put as list. Fifth, Benefits: combine "Be a changemaker You’ll Enjoy" bullet list plus benefits from compensation paragraph. Let's extract "Be a changemaker You’ll Enjoy" bullet points: - A flexible work environment that empowers you to do your best work - A culture that celebrates performance - The chance to make an impact in a team that’s big enough for career growth, but lean enough to make your voice heard - Career-defining opportunities - Plus benefits designed to keep you happy, healthy and fulfilled. Then list: - Flexible paid time off and remote work policies - Equity options, because this is your company too - Contributions to your pension plan. Your future matters - Training opportunities to grow your skills and career - Health and wellness credit so you feel your best - Time off to volunteer and give back to your community - Interest groups, employee led networks, social committees to sponsored sports teams - Computer purchase program to get your personal Macbook - Enhanced parental leave to support growing families Then after that paragraph: "Fuel your growth. Find your people. At Lightspeed, your growth is our priority. We invest in you with continuous learning opportunities, global mobility and benefits designed to support you—all within a driven, diverse and inclusive team that’s passionate about empowering our communities" Also compensation paragraph includes benefits: "Lightspeed also provides a variety of employee benefits including, but not limited to, medical, dental, wellness, life and disability insurance, 401K plan and match, paid parental leave top-up, and paid time off." We should include those as well. We must avoid duplication: we already have flexible paid time off, equity options, pension contributions, training opportunities, health and wellness credit, volunteer time, interest groups, computer purchase program, enhanced parental leave. Also we have medical, dental, wellness, life and disability insurance, 401K plan and match, paid parental leave top-up, paid time off (some overlap). We'll combine. We'll produce a Benefits section with a list combining all unique items. Let's compile list: - Flexible work environment that empowers you to do your best work - Culture that celebrates performance - Chance to make an impact in a team that’s big enough for career growth, but lean enough to make your voice heard - 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 (to get your personal Macbook) - Enhanced parental leave to support growing families - Continuous learning opportunities - Global mobility - Medical insurance - Dental insurance - Wellness programs - Life and disability insurance - 401K plan and match - Paid parental leave top-up - Paid time off (already have flexible PTO but we can keep generic) - Benefits designed to support you (maybe redundant) We should avoid redundancy: "Flexible paid time off and remote work policies" already covers flexible PTO; "Paid time off" maybe duplicate. We'll keep flexible PTO and remote work policies; we can also mention paid time off as part of that. We'll keep list but avoid exact duplicates. Now Pay section: include salary range and incentives. From text: "At Lightspeed, we carefully consider a wide range of factors when determining compensation, including your skillset, qualifications, experience, and market data. These considerations can cause your compensation to vary. We reasonably expect the base salary for this position to be in the range of $260,000 to $290,000 USD, depending on the candidate’s location. Additionally, this role may

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