Senior Engineering Manager

ABOUT US We’re a startup with big ambitions: to make estate planning modern, visual, and intelligent. Vanilla https://www.justvanilla.com/ is the first AI-powered estate advisory platform, built by advisors, planners, and attorneys to transform how wealth is transferred across generations. Our technology unifies scenario modeling, client visualization, and document creation into one seamless, digital experience. Our team brings together diverse subject matter expertise across estate planning, wealth management, and scaling SaaS startups. We’re distributed across the U.S., with a mix of fully remote and hybrid roles, and we embrace flexibility while staying closely connected. At Vanilla, you’ll join curious builders and problem-solvers who thrive on speed, autonomy, and impact. Here, you won’t just join a company, you’ll help create it. If you’re excited to tackle hard problems, move quickly, and see your work shape both an industry and a growing startup, we’d love to meet you. WORKING LOCATION This role is a remote position, you must be based out of one of the following states: Arizona, California, Colorado, Connecticut, Florida, Georgia, Idaho, Illinois, Kentucky, Maine, Massachusetts, Minnesota, New Jersey, New York, Ohio, Pennsylvania, Texas, Utah or Washington JOB SUMMARY As the Sr. Engineering Manager at Vanilla, you’ll be a true player/coach — a hands-on technical leader who spends a meaningful share of each week in the codebase alongside your team. You’ll write and review code, design and debug systems, and set the technical bar by example, while also leading a small team of engineers, providing direction, and supporting their growth. This is not a hands-off, manager-of-managers role: you’ll pair with engineers, pick up meaningful work in critical or ambiguous areas, and stay close enough to the details to make sharp technical calls. It demands a leader with deep, current technical skills, strong leadership instincts, and a passion for building great software in a fast-paced, start-up environment. RESPONSIBILITIES - Stay hands-on in the code contribute directly to the codebase—writing production code, reviewing PRs, and picking up meaningful work in critical, complex, or ambiguous areas. You lead by doing, not just directing.

• Set the technical bar by example architect and implement scalable solutions, drive strong engineering practices, and raise quality through the work you personally ship and the reviews you give.
• Coach and grow engineers through the work pair, mentor, and unblock your team in the moment.

• Lead end-to-end delivery balance speed with technical quality, bring clarity to complexity, and champion scalable design principles across your team’s work.
• Drive technical and product strategy align engineering execution with the company’s broader business goals and customer needs, and help architect solutions that scale both technically and operationally.
• Improve how the team builds implement systems, tools, and processes that improve development velocity, quality, and collaboration—often by prototyping the improvement yourself.
• Serve as a critical cross-functional partner work with product, design, marketing, sales, and support to align roadmaps, unblock execution, and ensure customer-centric outcomes.
• Support pre-sales and customer onboarding help technical stakeholders understand product capabilities, dig into integration details when needed, and ensure feedback from the field informs the roadmap.
• Coordinate external integrations and platform partnerships manage stakeholder expectations and, where it counts, get hands-on to ensure secure, seamless implementation.
• Define and own engineering metrics and KPIs drive continuous improvement in product quality, team performance, and operational efficiency.
• Collaborate with Legal and Security teams uphold compliance, privacy, and regulatory standards across all systems.
• Adopt the vanilla AI SDLC and scale it throughout the team and organization.

• Demonstrated ability to operate as a player/coach—comfortable splitting your time between shipping code and leading people, and energized by both.
• A track record of building and scaling complex software systems at high-growth SaaS companies or startups, as a direct contributor and not only as an overseer.
• Deep, current technical skills—you can jump into the codebase, reason about architecture, and debug hard problems yourself.
• Strong operational instincts; you’re process-oriented, data-driven, and focused on systems that enable high-leverage execution.
• Experience influencing product architecture and engineering strategy through a systems-thinking lens.
• Comfort navigating ambiguity and working autonomously in a fast-paced environment.
• Strong communication and leadership skills; you excel at guiding technical discussions and aligning diverse stakeholders.
• Prior experience in pre-sales engineering roles is highly valued.
• Project management experience, particularly in fast-paced or cross-functional environments, is a strong plus.
• Bachelor’s degree in Computer Science, Engineering, or equivalent practical experience.

Benefits

• Flexible paid time off policy and 10 company-wide paid holidays - Parental leave, 6 weeks for all full-time employees and up to 14 weeks for birthing parents - Medical, dental, and vision benefits coverage for employees and their families - 401K eligibility after one month of employment - Free estate planning documents - Budget for learning & development and home office setup - Paid parking or transit for hybrid and in office employees Vanilla Technologies Inc. (dba "Vanilla") provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws.

• Highlight specific examples where you wrote production code while leading a team; concrete stories beat generic statements.
• Demonstrate comfort with Excel‑driven metrics by sharing how you’ve used data to improve engineering processes.
• Prepare to discuss a time you partnered with non‑technical stakeholders (product, sales, legal) to resolve an ambiguous technical challenge.
• Include a brief portfolio or GitHub links that showcase code quality, architecture decisions, and mentorship activities.
• Research Vanilla’s AI‑powered estate planning focus so you can speak to how your experience aligns with their domain during interviews.
• When negotiating, emphasize the equity component and remote‑work stipend as part of the total compensation package.
• Watch for any requirement that you must be based in one of the specified states; ensure your location complies before applying.