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.

1. 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.

2. 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 validate "aha moments" e.g. a manager seeing team skill progression in the dashboard within 10 days, or an end user completing their first well-matched room within 7 days.

• Map product-action-based intervention triggers (not just email-engagement-based) feeding into Customer.io, Trig, and Intercom.

• Build and continuously refine journeys, playbooks, and automated task workflows in Trig and ChurnZero - adoption nudges, churn-prevention triggers, and renewal automation that scales across hundreds of customers.

• Define health scoring, trigger logic, and the exception paths where personal outreach is required; analyse automation performance continuously and iterate quickly.

This role expects hands-on ownership of automation, not passive administration of existing flows.

3. Renewals at Scale - Without Dedicated AMs

A critical part of this role is owning renewals where there is no dedicated Account Manager or named CSM per account. Renewal ownership in this segment is system-led by default, with human intervention only when the data signals risk or opportunity.

• Design and run automated renewal workflows — 3-month, 2-month, and 1-month email sequences — stepping in manually only when automation fails to drive action.

• Build renewal health and prediction models based on usage, engagement, and lifecycle signals, so risk is surfaced months in advance, not discovered at expiry.

• Create clear exception-handling paths for high-risk or high-potential accounts that warrant personal outreach.

• Maintain accurate renewal classification, forecasting, and risk visibility through automated signals rather than manual tracking.

The goal: renewals by default, supported by strong systems rather than manual chasing.

4. Customer Hub - Launch, Content & Governance

You're the operational owner of the customer hub/success portal: a single destination for onboarding guides, product updates, webinars, case studies, and FAQs.

• Marketing produces blogs, product-update comms, webinar assets, and case studies; as the CSM you curate, coordinate, and surface them.

• Maintain momentum post-launch so the hub is actively populated and used, not just shipped.

• Co-own the community hub with Marketing and the Community Manager, including case studies, success stories, and executive roundtable tie-ins.

• Own FAQ and onboarding guide content alongside CS stakeholders, auditing outdated material and prioritising what gets refreshed first.

• Coordinate owners for each resource type so updates keep happening, and ensure customers can self-serve onboarding, product info, and content discovery.

• Embed the hub into onboarding and ongoing customer comms with CRM/Product/Marketing - it must be part of the actual digital journey, not a standalone page.

5. One-to-Many Engagement & Customer Marketing

You'll work very closely with Marketing to deliver customer success at scale. This role blends Customer Success, CS Operations, and Customer Marketing into a single, outcome-driven motion.

• Co-own lifecycle-based customer communications across onboarding, adoption, and renewal, in practice this means: design and brief to CRM (marketing) lifecycle touchpoints Email and In-App

• Collaborate with marketing to run one-to-many webinars, feature spotlights, and educational customer events.

• Build a consistent engagement rhythm that mirrors high-touch CS digitally - so customers feel supported, educated, and guided without 1:1 management.

• Work closely with the growth marketer and the product managers who designed the core B2B product journey.

6. Product Partnership & Self-Serve Experience

Act as the key voice for digital and self-serve customers in close partnership with Product.

• Identify friction in self-serve onboarding and product discovery; surface where customers stall, disengage, or fail to reach value.

• Influence in-product education, guidance, and lifecycle nudges.

• Help define what "great" looks like for a hands-off, no-CSM customer experience.

7. Support Triage

• Triage inbound support tickets from digital accounts and own the escalation path - support delays have been flagged as a pain point for this segment.

• Use patterns in inbound queries to feed the hub and self-serve content, so the same questions stop arriving.

8. CRM, Reporting & Operational Excellence

Run this portfolio like a product.

• Maintain HubSpot hygiene across the digital book: tagging, pipeline routing, renewal classifications, and handover notes.

• Work with RevOps to ensure digital accounts are correctly segmented and reported separately from the strategic/Full CSM book.

• Co-own and build the CRM journey integration - mapping triggers, data points, and lifecycle comms for digital accounts, coordinating tooling across Customer.io, Trig, and Intercom.

• Monitor and build dashboards (with data/RevOps help) daily for health, adoption, churn risk, and renewal performance; analyse trends across hundreds of accounts to identify systemic improvements, not just individual account issues.

• Document and iterate on playbooks so success becomes repeatable. Forecasting accuracy is non-negotiable.

What Success Looks Like

Ongoing outcomes:

• ≥80% of digital customers actively engaging through digital journeys, webinars, or automated success communications.

• ≥80% renewal rate across the digital portfolio.

• Measurable reduction in manual CSM effort for onboarding and renewals.

• Clear, documented, repeatable playbooks owned by this role.

• Strong, trusted collaboration with Marketing and Product.

• Digital is no longer an operational bottleneck — it's a scalable growth engine.

6-Month Success Criteria (OKRs) - the de facto pass conditions for contract extension or conversion to permanent:

1. Digital journey V1 live - onboarding flow, lifecycle email sequences, and in-product triggers operational for the full digital cohort, building on the foundation Product and Marketing have laid.

2. Customer hub shipped - with at minimum 3 live initiatives feeding it (e.g. case studies, success stories, onboarding guides, webinar library).

3. CRM journey integration built - digital accounts correctly tagged, pipeline routed, and renewal tracking automated in HubSpot with RevOps, with dashboards (HEX likely) tracking the book's GRR progress.

4. GRR stabilised on the digital book - clear baseline established and churn rate, GRR improving vs. prior quarters.

5. Renewal automation operational - 3/2/1-month sequences running; manual intervention rate tracked and declining, customers’s successfully renewing themselves in the system.

What You'll Work With

Tooling: Customer.io (lifecycle comms) · Trig (activity-triggered nudges) · Intercom (in-app prompts) · HubSpot (CRM) · Hex (reporting/analytics) · Amplitude · Usage data

Cross-functional partners: Product · Marketing/CRM · RevOps & GTM Data Team · Head of CS

About You

✅ Essential

• 3+ years in Customer Success, CS Operations, Lifecycle, or Digital CS roles within B2B SaaS -including digital/scaled CS, lifecycle marketing, or customer marketing experience.

• Proven experience personally building automated onboarding, adoption, and renewal journeys. Designed and owned, not just maintained.

• Comfortable managing high-volume, low-ARR portfolios through systems rather than relationships.

• Strong experience with CRM and lifecycle tooling; HubSpot, Customer.io, ChurnZero, or equivalent.

• Data-driven with high data literacy: able to analyse behavioural signals, define activation thresholds, build intervention logic, and use metrics for decisions and storytelling.

• A strong process builder, this role is about creating systems, not managing relationships.

• Experienced working cross-functionally with Marketing and Product.

• Able to thrive in ambiguity as an independent builder. This motion doesn't fully exist yet, and you'll be the orchestrator expected to hit the ground running.

🌟 Nice-to-have

• Experience with in-app engagement tooling (Intercom or similar).

• Background in cybersecurity or technical SaaS.

• Experience defining and validating product activation metrics / "aha moments".

Demonstrated Ownership

Strong candidates can clearly show:

• What they built, not just what they maintained.

• How their automation directly improved renewal or retention outcomes, reduced manual effort, or improved scale.

• How they identified risk before it escalated.

• Where something didn't work, and how they iterated the system over time.

• What changed for customers because of the systems they designed.

What This Role Is Not

• Not a high-touch CSM role - no EBRs, QBRs, or 1:1 relationship management of individual accounts at scale.

• Not a marketing role - though you'll work closely with Marketing on email and content.

• Not an expansion-closing role - the AM team handles large expansion deals. You focus on retention and digital engagement, step in when customers don't act, and pass larger expansion opportunities to Enterprise or another owner when needed.

This role is probably not a fit if you:

• Need significant guidance or can't work under ambiguity. This is a genuine opportunity to shape how TryHackMe scales its digital customers, but there's no pre-defined playbook.

• Prefer traditional, relationship-heavy account management.

• Haven't personally built automation or lifecycle journeys.

• Are uncomfortable owning renewals without dedicated AMs.

• Rely on manual intervention as the primary lever for retention.

Duration & Trajectory

• Initial term: 6 months.

• Extension/conversion: If the digital motion is working and the book requires ongoing ownership, the role extends or converts to permanent.

• Marketing and Product have both flagged this as a full-time need. There is a very strong likelihood of permanence.

🌱 Traits That Thrive at TryHackMe

Our strongest Scale CSMs demonstrate:

• Ownership — "If not me, then who?"

• Bias for Action — progress over perfection.

• Systems Thinking — solve root causes, not symptoms.

• Customer Empathy — even at scale.

• Craftsmanship — pride in clean journeys and great experiences.

Customer Success at TryHackMe is not a support function. It is a growth engine built on outcomes, systems, and ownership.

🚀 Why This Role Matters

If this role is done well:

• Digital customers receive a better experience.

• Renewals become predictable and scalable.

• Manual CS workload drops significantly.

• The wider CS team gains capacity for higher-value accounts.

• TryHackMe scales sustainably without sacrificing customer outcomes.

This role directly shapes how Customer Success scales at TryHackMe.