Senior Director, Integrations Cloud at Coursedog in Remote

The Opportunity

As a Senior Director, Integrations Cloud at Coursedog, you'll transform how institutions connect their systems and data. Today, integrations are a critical part of our platform, and also our single largest source of controllable customer-health risk. This is a net new role that will own the Integrations Cloud as a business, set its multi-year vision, and be accountable for both the platform we build and the retention outcomes it drives. You'll own the vision, strategy, and execution to turn integrations into our competitive advantage: a unified, self-service data-connectivity layer that scales across any SIS or LMS ecosystem and becomes the intelligence engine the entire platform runs on. You'll drive the shift from engineering-dependent custom wiring to a flexible, extensible platform that lets schools safely wire their own integrations. You'll establish the operational rigor—SLAs, reliability, adoption metrics—that keeps this a world-class organization. And you'll own the business outcomes: retention, time-to-value, and expansion driven by integration capabilities.

This role is for someone who can hold a multi-year platform vision and a two-week delivery cycle at the same time; who understands data models and SIS architecture deeply enough to be credible with engineers; and who can align Product, Engineering, and customer-facing teams around a shared outcome.

This role is scoped at the Senior Director level and reports to the President, while working cross-functionally with the leaders of Product, Engineering, and Customer Experience.

This position offers a competitive base salary between $175,000 - $200,000, based on experience and qualifications. The role also includes a performance-based variable compensation component, bringing total on-target earnings (OTE) to $210,000 - $250,000 when performance objectives are achieved.

What You'll Do

• Own the Integrations Cloud vision and multi-year North Star for data connectivity; set strategy and own the business outcomes that matter — net revenue retention and churn reduction attributable to integrations, time-to-value at implementation, and the platform's contribution to expansion.
• Drive the platform transformation from today's engineering-dependent wiring model to a flexible, self-service platform — 100% baseline field coverage for core products, migration off customFields into a first-class schema, extendedFields for clean schema extension, and eventually customEntities that let schools bring in any external source.
• Lead the cross-functional integration-fit customer-health program that fixes our controllable churn driver — moving field-level discovery from mid-implementation to a dedicated pre-build Intake step, ratifying a shared, machine-readable definition of "baseline vs. custom," and standing up the demand-to-roadmap loop that turns aggregated gap data into prioritization.
• Own Integration Engineering and Data Client Experience roadmap timing, scope, and delivery; the health of the core pipeline (merge behavior, merge-report reliability, sync stability) that thousands of field-level integrations depend on; and disciplined portfolio management — blocker burndown, SLA commitments, capacity allocation, and tech-debt paydown.
• Establish and own systems integration architecture — multi-SIS federated, single-SIS multi-tenant, and hybrid patterns; the cross-tenant capability layer (identity, RBAC, aggregated reporting, workflow hooks); and foundational moves such as institutional scope as a first-class primitive.
• Set strategy for deep, certified, reusable integration patterns across Banner, Colleague, PeopleSoft, Workday, Anthology, Jenzabar, and others; own key vendor relationships; and partner with GTM on technical scoping, RFP defense, and commercial framing.
• Build and lead a multidisciplinary organization of integration and platform engineers, product owners, and functions that bridge Data Engineering and Customer Experience; develop the next layer of leaders within it.
• Establish the operating cadence and metrics (reliability, SLA attainment, time-to-value, self-service adoption, retention) that make this an accountable, well-run organization.
• Leverage AI capabilities across the integration platform to accelerate discovery, reduce manual work, and improve decision-making.

What you'll do in the first year

• Publish and align the organization on the Integrations Cloud North Star and its sequencing, and secure the investment to execute it.
• Stand up the cross-functional integration-fit working group, ratify the field-level baseline definition, and pilot the AI gap-map on live deals — with a measurable reduction in integration-driven escalations and churn as the goal.
• Bring order to the escalated-customer portfolio: eliminate uncommitted blockers, put SLAs on agreed gap-field work, and wire those commitments into the implementation plan.
• Make demonstrable progress toward 100% baseline field coverage and ship the first self-service wiring (extendedFields) that removes Integrations Engineering as a bottleneck.
• Deliver the near-term systems unlocks (cross-tenant identity, system-level workflow participation, aggregated reporting) that let Coursedog win system deals before the full platform exists.
• Establish the operating cadence and metrics (reliability, SLA attainment, time-to-value, self-service adoption, retention) that make this an accountable, well-run organization.

What You'll Bring

• 12+ years in software with significant time in integration/data-platform leadership or product-line/GM ownership and proven people leadership including leading leaders; track record of setting a multi-year platform vision and executing it into shipped, adopted product; experience owning or materially influencing retention/customer-health outcomes.
• Proven organizational leadership — you've led a cross-functional organization or a platform/business line and own outcomes, not just a team; you're comfortable owning a number and a P&L-level charter.
• Deep systems thinking with shipping rigor — you thrive at holding a multi-year platform vision and a two-week delivery commitment at the same time, and you're credible with engineers because you understand the data model, integration patterns, and SIS-level detail.
• Extensive experience building or scaling a data-connectivity or integration platform; deep understanding of SIS/LMS ecosystems (Banner, Colleague, PeopleSoft, Workday) and integration patterns (Ethos/APIs, batch, custom controllers); expertise in extensible/multi-tenant data modeling and data-sovereignty concerns.
• Strong customer-health and commercially minded approach — you excel at connecting platform decisions to retention, expansion, and time-to-value, and you can lead cross-functional programs that change how the company sells, scopes, and implements.
• Proven operational discipline — you have strong experience running a portfolio with rigor (SLAs, blocker burndown, capacity, tech debt) and hold quality, performance, and adoption as non-negotiable guarantees.
• Strong communication and leadership development skills — you have proven experience leading through written strategy and direct decisions, and you grow the managers and product owners beneath you.
• Experience evaluating and integrating AI tools into platform workflows and product features; ability to identify where AI can meaningfully reduce manual work without sacrificing quality or control.
• Higher-education technology experience strongly preferred.

Not sure if you should apply? Research shows that women and people from underrepresented backgrounds are less likely to apply unless they meet every qualification listed. At Coursedog, we're focused on finding the best person for the role, and that person may come from a non-traditional background. We encourage you to apply even if you don't meet every requirement — our evaluation focuses on your ability to thrive in this role and make an impact.

Working at Coursedog

Healthcare, Dental & Vision

We follow a fixed contribution model to promote equity and transparency. Every employee receives the same annual dollar amount to apply toward medical, dental, and vision coverage. This approach gives you the flexibility to choose the plan that best fits your needs, whether that is a base-level option or more comprehensive coverage.

Depending on the selected coverage level, the company covers:

• Employee-only coverage: 99% to 65% of monthly premiums
• Employee plus dependents: 77% to 50% of monthly premiums

We partner with Aetna and Guardian, and offer access to best-in-class wellness and support programs, including:

• Spring Health (mental health support)
• XP Health (vision benefits)
• Carrot Fertility (family planning support)
• One Medical (primary care)

We also support pre-tax savings through Health Savings Accounts (HSA) and Flexible Spending Accounts (FSA).

Retirement Planning

To support long-term financial health, we offer a Safe Harbor 401(k) plan from day one of employment. Coursedog provides a 4% employer match on your total compensation (subject to federal limits) each pay period for employees contributing to a tax-advantaged retirement account.

Paid Time Off

We trust our employees to manage their time responsibly. That’s why we offer an unlimited Paid Time Off policy — because flexibility and balance are critical for sustained excellence and personal well-being.

Remote-First Since Inception

We were built for distributed work. Our culture emphasizes flexibility over rigidity, outcomes over hours, and transparency over gatekeeping. We are committed to being a remote-first organization indefinitely, empowering you to work where and how you thrive best.

Equity

As a valued contributor to our collective success, you’ll participate in the upside. All employees are granted equity in the company aligned to your role and tenure. Equity grants are reviewed and adjusted with promotions to reflect your evolving impact.

Paid Parental Leave

Coursedog supports all parents regardless of gender, family structure, or how you became a parent. All parents receive up to 6 weeks of Paid Bonding Leave at 100% of base pay following the birth, adoption, or foster placement of a child. Birthing parents receive an additional 6 weeks of Paid Medical Recovery Leave at 100% of base pay to support physical recovery following childbirth — for a total of up to 12 weeks of fully paid leave.