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Director of Customer Success, Scaled

US-REMOTEPosted 23 Oct 2026

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About this role

At Instructure, we believe in the power of people to grow and succeed throughout their lives. Our goal is to amplify that power by creating intuitive products that simplify learning and personal development, facilitate meaningful relationships, and inspire people to go further in their education and careers. We do this by giving smart, creative, passionate people opportunities to create awesome. And that's where you come in: We are seeking a Director of Customer Success, Scaled to lead the teams serving our scaled customers and to build a motion that reaches all of them well.

Your team covers our entire scaled and digital customer base: the largest part of our base. The Director of Digital Customer Success reports to you and runs the global digital team, and multiple Managers report to you covering the scaled segments. This is a new role, and the managers and teams serving these customers sit in business units today. Part of your job is bringing them together into one team with one way of working, and running that transition so customers see continuity rather than a reorganization.

WHAT YOU WILL BE DOING: Building and leading the scaled Customer Success team: - Align a new team from managers and Customer Success professionals who sit in business units today, and run the transition so customers see continuity rather than a reorganization. - Lead a team of Managers who own the scaled segments, coaching them to upskill and grow their teams. - Lead the Director of Customer Success, Digital, who runs our global digital team, and build one connected organization across the scaled and digital motions rather than multiple separate functions.

- Own hiring, onboarding, performance, career development, and succession planning for the team, and build a bench that can absorb growth. - Set the coaching standard for scaled work: what good looks like in a persona-based plan, a 1:many engagement, a risk signal, and a value conversation that happens at volume. - Design the organization: headcount, team structures, coverage ratios, and reporting lines that fit the strategy.

- Hold a consistent operating rhythm that keeps managers accountable and connects a team drawn from several business units and several regions. - Account for the realities of a global team, including time zones, regional customer expectations, and academic calendars that do not line up. Delivering retention and growth across the scaled and digital customer base: - Hold retention and bookings targets for the scaled and digital customer base.

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- Partner with Sales and the Renewals team on forecast, renewal execution, and expansion across a book measured in thousands of accounts rather than dozens. - Work in cohorts, not accounts: find the patterns that predict risk and expansion at volume, and aim the team's effort where it changes the number. - Define what the scaled team needs from adoption analytics and partner with CX Ops to get it built. - Report on the health of the scaled base in terms leadership can act on, and bring data-driven business cases when the model needs investment.

- Know the cost to serve, and improve it without quietly reducing what customers actually get. Leading automation and AI to create an efficient scaled motion: - Own the automation and AI roadmap for the scaled motion: what gets automated, in what order, and what measurably improves as a result. - Use AI to extend what a small team can cover, including risk detection across thousands of accounts, drafting and personalizing outreach at volume, and surfacing adoption signals nobody would have time to find by hand.

- Decide what work stops once automation can carry it, and redeploy that time into customer outcomes rather than absorbing more volume at the same quality. - Partner with CX Ops, RevOps, and Product on the systems the motion runs on, including Gainsight, journey orchestration, and product analytics, and on the data quality all of it depends on. - Hold the line on company AI policy, customer data privacy, and what we will and will not put in front of a customer without a person reviewing it.

- Keep a human in the loop where the relationship calls for it, and be able to say where that line sits and why. - Build the measurement: coverage per head, time from risk signal to response, cost to serve, and whether an automated touch actually moved adoption. - Make AI fluency an expectation of the job for managers and individual contributors, and coach the team to use it for judgment rather than only for speed. Running 1:many customer outreach: - Deliver 1:many customer outreach for the entire global customer base.

- Own execution end to end: audience building, send timing against regional and academic calendars, quality review before anything reaches a customer, and the calendar that keeps it all coherent. - Produce the lifecycle and campaign content your team sends, drawing on the product specialist team for product substance. - Keep the sequence coherent so a customer hears one voice from Instructure rather than five teams landing in the same inbox in the same week.

- Give dedicated CSMs a way to personalize or hold an account back when the relationship calls for it, and make the default path good enough that they rarely need to. - Report on reach, engagement, adoption movement, and how much CSM time the program gave back. HERE IS WHAT YOU WILL NEED TO KNOW/HAVE: Successful candidates will have the following education, experience, and skills: - Experience designing and running a scaled, pooled, or digital Customer Success model at volume, and evidence that it delivered outcomes rather than just coverage.

- A track record of leading managers and leaders of leaders, not only individual contributors, and growing leaders who decide without you. - Experience standing up a new team or centralizing a function out of business units, including the transition work that protects customers while it happens. - Experience holding retention and bookings targets across a large portfolio, and the analytical judgment to work in cohorts rather than account by account.

- Demonstrated ownership of automation in a customer-facing operation: what you automated, what stopped, and what measurably improved. - Using AI to fundamentally change how teams operate. - Experience building team structures, coverage models, and segmentation that fit a strategy, and making the case for changing them. - Experience running 1:many customer communication at volume, including the governance that keeps internal teams from competing for the same inbox.

- Experience leading a globally distributed team, including the regional and time zone realities that come with it. - Strong leadership presence with both customers and internal executives, including the ability to influence decisions without formal authority. - Strong analytical skills, with the ability to work in Gainsight, Salesforce, product analytics, journey orchestration, and reporting tools to turn data into a decision.

- Exceptional written and verbal communication skills, including the ability to translate customer detail into business impact for executives. - A calm, decisive presence under pressure, with the judgment to manage ambiguous, high-stakes situations across multiple stakeholders at once. - Willingness to travel to customer sites, conferences, and team onsites. - A bachelor's degree or equivalent experience. Get in on all the awesome at Instructure! We offer competitive, meaningful benefits in every country where we operate.

While they vary by location, here's a general idea of what you can expect: - Competitive compensation, plus all full-time employees participate in our ownership program - because everyone should have a stake in our success. - Flexible work culture. Our remote, hybrid and in-office collaboration spaces vary by role, team and location. - Generous time off, including local holidays and our annual “Dim the Lights” period in late December, when teams are encouraged to step back and recharge based on departmental needs.

- Comprehensive wellness programs and mental health support - Learning and development resources, including professional development tools and tuition reimbursement, to support your growth - The technology and tools you need to do your best work - Motivosity employee recognition program - A culture rooted in inclusivity, support, and meaningful connection We believe in hiring great people and treating them right. The more diverse we are, the better our ideas and outcomes.

Instructure is an Equal Opportunity Employer. We comply with applicable employment and anti-discrimination laws in every country where we operate. All employees must pass a background check as part of the hiring process. To help protect our teams and systems, we’ve implemented identity verification measures. Candidates may be asked to verify their legal name, current physical location, and provide a valid contact number and residential address, in accordance with local data privacy laws.

Any attempt to misrepresent personal or professional information will result in disqualification.

Source listing: ashby_instructure

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