Senior Director of Engineering, Core Product

Coursedog

4d•$210,000 - $250,000•Remote

About The Position

As a Senior Director of Engineering, Core Product at Coursedog, you'll own the day-to-day execution and engineering health of Coursedog's three core product clouds — Assessment, Curriculum, and Scheduling — so they ship reliably, hit their commitments, and defend the revenue base. You'll work closely with engineering managers, product leadership, and cross-functional partners to translate the roadmap into reliable, high-quality software. This is a delivery-and-execution leadership role — focused on building and running the products customers pay for today. This role will be the single accountable leader for how core product engineering executes, week over week and quarter over quarter. You'll pioneer an AI-augmented development model where clear specifications unlock high-quality, AI-accelerated delivery. You'll be responsible for predictable shipping, quality, and reliability, and driving a step-change in engineering velocity through AI and spec-driven practices, while building a strong bench of engineering leaders in a fast-moving, mission-driven environment. This role reports directly to the SVP, Software Engineering and collaborates cross-functionally. This role is well-suited for someone who operates with both strategic vision and operational rigor, takes ownership of hard problems, and is motivated by building systems and teams that scale sustainably. If you're excited by the chance to lead a major engineering function, shape how a critical part of the product organization executes, and transform how an entire engineering org builds software through AI-augmented, spec-driven practices, this is an opportunity to have outsized impact at a high-growth company.

Requirements

10+ years in software engineering with 5+ years leading engineering teams, including managing engineering managers (manager-of-managers experience required)
Track record running multiple teams or product lines simultaneously and delivering predictably at scale
Experience leading an AI transformation of an engineering org — driving adoption of AI-assisted development and/or spec-driven practices, and raising the quality bar as AI-generated code volume increases
A metrics-driven leadership style — fluency with delivery and quality metrics (DORA, defect/escape rates, SLA attainment) and the judgment to know when a metric is a floor vs. a goal
Demonstrated ability to hold teams accountable — set clear commitments, follow through on outcomes, and address performance directly
Demonstrated ownership of engineering quality and reliability — not just feature throughput
A record of building a continuous-improvement culture — where standards rise and the system measurably improves over time
Strong operating instincts: can walk into a portfolio of in-flight work, quickly read where it actually stands, and make calls
Excellent cross-functional partnership with product and customer-facing teams; clear, candid communication with executives
B2B SaaS experience; bonus for complex, integration-heavy, multi-tenant products
Familiarity with a cloud/pod model and modern delivery tooling (Jira, CI/CD with continuous deployment, observability, automated testing)

Nice To Haves

Higher-education technology or other regulated/enterprise vertical experience
Background scaling teams through rapid growth and process maturation
Hands-on experience standing up spec-driven workflows or AI development tooling at team or org scale

Responsibilities

Lead the AI transformation into a spec-driven development org: Own the shift from ad-hoc coding to a spec-driven model where well-defined specifications drive design, implementation, review, and testing — and where AI tooling is used to accelerate delivery without eroding quality. Set the standard for how specs are written, versioned, and used as the contract between product intent and shipped code. Make AI-assisted development a durable competitive advantage across all three clouds, and raise the quality bar as AI-generated code volume grows.
Lead through metrics: You run the org on data, not anecdote. Define the metrics that tell the truth about delivery, quality, and reliability; make them visible; and use them to drive decisions, expose risk early, and focus the teams. You model metric-driven leadership for your EMs and know when a number is a floor, a goal, or a distraction.
Hold teams accountable: You are the single accountable leader for core product delivery, and you build that same accountability into every team. Set clear commitments and a clear definition of done, make ownership unambiguous, follow through on outcomes, and address underperformance directly and fairly. Commitments mean something on your teams.
Build a continuous-improvement culture: Create an engineering culture that gets measurably better every quarter — where retros lead to change, standards rise over time, experimentation is safe, and improving the system is everyone's job. You partner with your engineering managers to make continuous improvement a habit, not an event.
Multi-cloud engineering leadership: Set the standard for how the Assessment, Curriculum, and Scheduling teams plan, build, review, test, and release. Hold the line on consistency across all three without flattening what makes each cloud distinct.
Day-to-day execution: Sprint health, throughput, and delivery against quarterly commitments are yours. Run the cadence through your engineering managers, clear blockers fast, and make the trade-off calls when scope, quality, and timeline collide.
Quality and reliability: Own the quality bar for core product — driving down Change Failure Rate and Escaped Defect Rate, keeping the bug backlog contained, holding SLA compliance across all severity tiers, and protecting production availability. Quality is a first-class outcome, not a cleanup task.
People leadership: Lead and grow a team of engineering managers and their pods. Hire, level, coach, and develop EMs; run calibration and performance cycles; build a bench. You are a manager of managers.
Cross-functional partnership: Operate as the engineering counterpart to product, design, and customer-facing leadership for the three clouds. Translate roadmap into deliverable specs and plans, surface risk early and honestly, and keep commitments realistic and met.
Engineering operating system: Strengthen the practices that make delivery compound rather than erode — spec quality, estimation discipline, definition of done, code review standards, release process, and metrics that tell the truth about where teams actually stand.

Benefits

Competitive base salary between $175,000 - $200,000
Performance-based variable compensation component, bringing total on-target earnings (OTE) to $210,000 - $250,000
Medical, dental, and vision coverage
Spring Health (mental health support)
XP Health (vision benefits)
Carrot Fertility (family planning support)
One Medical (primary care)
Health Savings Accounts (HSA)
Flexible Spending Accounts (FSA)
Safe Harbor 401(k) plan
4% employer match on total compensation for 401(k)
Unlimited Paid Time Off policy
Remote-First work environment
Equity in the company
Up to 6 weeks of Paid Bonding Leave at 100% of base pay for parents
Additional 6 weeks of Paid Medical Recovery Leave at 100% of base pay for birthing parents