Digital Customer Success Manager
TryHackMeRole 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 f