Digital Customer Success Manager

Role at a Glance Contract - 6-month initial term, with genuine potential to extend or convert to permanent Portfolio - 115+ digital customer accounts · up to £1M in TCV (with more being added over time) Segment - High-volume, low-ARR, delivered primarily through automation, lifecycle journeys, and self-serve experiences Reports to - Head of Customer Success Location Remote (UK preferred) Our Mission TryHackMe makes learning cybersecurity accessible, practical, and engaging for everyone. With more than 8+ million learners worldwide, we're transforming how cybersecurity is taught, from school and university classrooms to professional training programmes. The Role This is a newly created, project-based contractor role designed to own and operationalise TryHackMe's digital customer journey, from onboarding automation through to renewal, for customers who don't require, or want, a traditional high-touch CSM relationship. You'll own a portfolio of 115+ digital accounts worth ~£1M in TCV, being intentionally carved out as its own book of business. But this is not a role about managing accounts individually, it's about designing the system that manages them well. This is an ops-heavy, data-driven role, not an EBR-style CSM position: the right person is comfortable working with lifecycle tooling, analysing behavioural signals, and building scalable processes rather than managing individual relationships. • Triage the book. Go through all 115+ accounts and decide what gets automated, what gets migrated to true self-serve, and what we let go of at renewal. Flag genuine expansion signals to the Enterprise CSM and AM teams to manage properly, your focus is primarily retention and digital engagement. • Build and run the system for what's left. Design the automation, lifecycle journeys, customer hub, and renewal workflows that keep this segment engaged, adopting, and renewing with minimal human touch, because the system works. This role sits at the centre of how TryHackMe scales. Done well, it unlocks capacity across the entire CS organisation and turns digital from an operational bottleneck into a predictable, high-performing system. Success depends on systems thinking, digital execution, and cross-functional collaboration, not inherited relationships or manual intervention. What "Digital" Means at TryHackMe Digital customers are still worth keeping in a CSM-owned book, but don't need ongoing high-touch management. Human involvement happens at trigger points, not on a regular cadence. An account belongs in Digital when most of these are true: • Reasonable ICP fit - worth retaining and caring about. • Some future expansion or upsell possibility, even if not immediate. • Doesn't need frequent human attention, but hasn't opted out. • Responds to lifecycle comms or trigger-based outreach occasionally. • Likely to self-renew, but CS should retain visibility and the ability to intervene. • Regrettable churn - we'd care if they left, even if proactive contact is light. In practice, that means: • A named CSM (you) owns the book, with no orphaned accounts. • Lifecycle comms, automated check-ins, and usage alerts are active. • You intervene when an expansion signal appears, adoption drops, renewal risk emerges, or a customer explicitly asks for support. • Customers may self-renew, that's fine, but CS tracks it. • No regular scheduled calls unless triggered; no QBRs or EBRs unless there's a clear commercial reason. Two traps to avoid: • Digital is not neglect. These customers still get proactive lifecycle comms, monitoring, and human intervention at key moments if required. Lighter-touch, not no-touch. • Digital doesn't work without automation in place. The model only holds if the lifecycle infrastructure, usage alerts, renewal triggers, comms cadence - is actually set up across our tools. Building and maintaining that is a core part of this job. What Will Already Be in Place When You Join You're not starting from scratch. By the time you join, core elements of the digital journey are expected to be underway or established across Product, Marketing, and Customer Success: The customer hub / self-serve experience: • A V1 for the customer hub, including core sections: product updates, content updates, webinars, blogs/resources, case studies, FAQs, onboarding guidance, and support/contact routes. • An agreed MVP approach - compiling and improving existing customer-facing resources rather than building a fully bespoke experience from scratch. • Initial design and product thinking on where it should live (in-product help widget, management dashboard, or another lightweight destination), with Product supporting the technical implementation of a first version - technical feasibility is not expected to be the blocker. • Marketing input into the brief, structure, presentation, and customer-facing content experience, including how blogs, webinars, case studies, and related assets are organised, tagged, and surfaced. • A defined list of priority content and resource areas, plus an understanding that existing FAQs and guides need audit and refresh - with initial review work from CS stakeholders before you take over ongoing coordination. The wider digital journey: • Digital onboarding journey design. Product is already working on the onboarding experience for customers entering without a high-touch CS motion. • Management dashboard development, including new sections that could surface digital journey elements (content, events, customer resources) directly in-product. • Content discoverability thinking - how customers find new rooms, learning paths, and updates without relying on ad hoc CSM guidance. • Recommendation/personalisation direction, including a content recommendation engine and customised ways to surface content by customer focus area. • Customer communications infrastructure - planned areas for product updates, content updates, webinar promotion, recorded content, and resource libraries. • Community and engagement concepts - Many webinars, executive roundtables, customer success stories, case studies, and making customers feel part of a wider TryHackMe community. • Early thinking on support and contact pathways for digitally managed customers. The gap this role fills: Product, Marketing, and CS each own parts of the experience, but no single person currently owns the end-to-end digital customer journey . You'll be the one who connects these components into a cohesive journey, makes them operationally effective, and continuously improves them based on customer needs. What You'll Own 1. Portfolio Triage & Segmentation Your first and ongoing responsibility: know exactly what's in the book and what each account needs. • Work through all 115+ accounts and classify each as an automation candidate, a true self-serve migration, or an account to release at renewal. • Build a clear, proactively surfaced picture of which accounts are self-serve candidates vs. digital-retain vs. at-risk. • Flag genuine expansion and upsell signals to the Enterprise CSM and AM team with context, large expansion deals are theirs; retention and engagement are yours. • Monitor account health using data signals, usage, seat activation, engagement triggers - rather than relationship-led outreach. 2. Digital Onboarding & Lifecycle Automation Treat digital as a systems problem, not a people problem. • Partner with Product and Marketing to build and iterate TryHackMe's first scalable B2B digital onboarding journey, covering activation, early adoption, ongoing low-touch engagement, and renewal. • Maintain structured 30–90 day onboarding paths that drive fast time-to-value without manual CSM involvement, with clear success milestones and adoption benchmarks so customers "graduate" into self-sufficiency with confidence rather than disengaging silently. • Continue to va