
51 - 200 employees
Founded 2018
🔒 Cybersecurity
📚 Education
☁️ SaaS
Cybersecurity • Education • SaaS
TryHackMe is an online learning platform that makes learning and teaching cybersecurity accessible and practical through prebuilt courses, cloud-hosted virtual machines (VMs), and hands-on labs designed for CTFs, workshops, assessments, and training. Launched in 2018, the platform emphasizes practical, deployable environments so users can avoid local VM configuration, and it serves millions of learners while supporting both individual and organizational training needs.
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51 - 200 employees
Founded 2018
🔒 Cybersecurity
📚 Education
☁️ SaaS
Cybersecurity • Education • SaaS
TryHackMe is an online learning platform that makes learning and teaching cybersecurity accessible and practical through prebuilt courses, cloud-hosted virtual machines (VMs), and hands-on labs designed for CTFs, workshops, assessments, and training. Launched in 2018, the platform emphasizes practical, deployable environments so users can avoid local VM configuration, and it serves millions of learners while supporting both individual and organizational training needs.
• Own and operationalise TryHackMe’s digital customer journey from onboarding automation through renewal • Manage and triage a portfolio of 115+ digital customer accounts worth approximately £1M in TCV • Classify accounts as automation candidates, true self-serve migrations, digital-retain accounts, or accounts to release at renewal • Flag expansion and upsell signals to Enterprise CSM and Account Management teams • Monitor account health using usage, seat activation, engagement, and other behavioural data signals • Build and iterate scalable B2B digital onboarding journeys and 30–90 day onboarding paths • Define aha moments, health scoring, trigger logic, intervention rules, and exception paths • Build and refine lifecycle journeys, playbooks, automated tasks, adoption nudges, churn-prevention triggers, and renewal automation • Design and operate automated 3-, 2-, and 1-month renewal email sequences • Build renewal health and prediction models and maintain renewal forecasting and risk visibility • Own the operational launch, content, governance, and ongoing usage of the customer hub/success portal • Curate and coordinate onboarding guides, product updates, webinars, case studies, FAQs, and customer resources • Co-own lifecycle communications, webinars, feature spotlights, and educational customer events with Marketing • Represent digital and self-serve customers in partnership with Product; identify onboarding and product-discovery friction • Triage inbound support tickets from digital accounts and own escalation paths • Maintain HubSpot hygiene, tagging, pipeline routing, renewal classifications, and handover notes • Build CRM journey integrations across Customer.io, Trig, Intercom, and HubSpot • Monitor dashboards for health, adoption, churn risk, and renewal performance using Hex, Amplitude, and usage data • Document and iterate playbooks to make customer success repeatable • Deliver six-month OKRs including a live digital journey, customer hub, CRM integration, stabilised GRR, and operational renewal automation
• 3+ years in Customer Success, CS Operations, Lifecycle, or Digital CS roles within B2B SaaS • Experience in digital/scaled CS, lifecycle marketing, or customer marketing • Proven experience personally building automated onboarding, adoption, and renewal journeys • Experience managing high-volume, low-ARR portfolios through systems rather than relationships • Strong experience with CRM and lifecycle tooling such as HubSpot, Customer.io, ChurnZero, or equivalent • High data literacy; ability to analyse behavioural signals, define activation thresholds, build intervention logic, and use metrics for decisions • Experience building processes and systems rather than managing relationships • Experience working cross-functionally with Marketing and Product • Ability to thrive independently in ambiguity and hit the ground running • Nice-to-have: experience with in-app engagement tooling such as Intercom • Nice-to-have: background in cybersecurity or technical SaaS • Nice-to-have: experience defining and validating product activation metrics or “aha moments”
• Potential extension or conversion to permanent after the initial 6-month term • Fully remote work • Opportunity to shape how TryHackMe scales its digital customers • Work with cross-functional teams across Product, Marketing, RevOps, and GTM Data • Potential for ongoing full-time employment if the digital motion is successful
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