Customer Success Manager (Maternity Cover)

TryHackMe | Remote-first | Fixed Term, ~8 months

At TryHackMe, our mission is to make learning and teaching cybersecurity accessible, practical, and deeply engaging. With over 6 million learners worldwide, we help organisations build real cyber capability — from classrooms to enterprises and critical national infrastructure.

We're hiring a Customer Success Manager to fully own one of TryHackMe's most important B2B books of business while a member of our CS team is on maternity leave. This is a genuine end-to-end ownership role, not a caretaker position — you'll run the account book the way it should always have been run: deeply, proactively, and commercially.

🎯 Role Overview

As Customer Success Manager, you'll own a portfolio of ~72 B2B accounts representing ~$823K in combined contract value, with individual contracts ranging from standard mid-market agreements up to strategic accounts worth $65K+. This is a genuinely global, cross-industry book, concentrated in a few high-stakes sectors:

• Technology & IT — software, network security, IT services

• Financial Services — banking, insurance, capital markets

• Critical Infrastructure — utilities, construction, healthcare, transportation

Clients span the US, UK, Germany, Austria, Australia, and the Middle East.

This book has real, defensible value — the majority of it is healthy and well-adopted — but a meaningful share has historically had inconsistent coverage as it moved across a stretched team. This role exists to give it the focused, singular ownership it's been missing, and there's real opportunity here to rebuild momentum on accounts that haven't had the attention they deserve.

This role requires proactive, visible, hands-on ownership. We are not looking for someone who primarily focuses on internal process or operational clean-up. Success depends on consistent customer-facing engagement, independent relationship-building, and the ability to run commercial conversations — including renewals and standard expansions — without relying on someone else to close the deal.

What "full ownership" means in practice:

• You own the account relationship, adoption, and outcomes — the core CS work

• You own renewals directly for your book — managing the process and handling the commercial conversation yourself, not handing it off

• You own standard, manageable expansion opportunities directly

• For genuinely large or complex expansion motions, you have an Account Manager you can bring in — but the day-to-day commercial ownership sits with you

A meaningful portion of this book (roughly a third of its value) involves accounts complex enough to require real negotiation skill and commercial confidence — this is a big part of why we need someone who can operate as a true full-cycle CSM, not a pure relationship manager.

💡 Key Responsibilities

Customer Outcomes & Retention

• Act as the primary relationship owner across your entire portfolio, building trust across technical, operational, and leadership stakeholders

• Run Executive Business Reviews, build multi-threaded stakeholder relationships, and drive adoption across TryHackMe's suite (SOC Maturity, Tabletop Exercises, Live Breach, Certifications)

• Establish a regular, documented engagement cadence — no account sits untouched without clear justification

• Monitor adoption health (usage, engagement, milestone completion) and proactively intervene to mitigate risk well ahead of renewal

• Manage at-risk accounts proactively, escalating early with clear mitigation plans rather than at the point of crisis

Renewals & Commercial Ownership

• Own renewal readiness and execution for your book, beginning well ahead of expiry, with documented plans for any amber or red accounts

• Run standard commercial conversations — quotes, terms, negotiation — directly yourself

• Bring in Account Manager support for larger, more complex expansion opportunities, while retaining relationship ownership throughout

• Maintain accurate renewal classification, forecasting, and CRM documentation to support predictable outcomes

Adoption, Engagement & Expansion

• Drive fast time-to-value and embed TryHackMe deeply into each customer's security or training workflows

• Identify adoption-led expansion signals — seat growth, new teams engaging, demand for CTFs, SOC simulators, TTX, or certifications

• Convert standard expansion signals into closed opportunities yourself; partner with the Account Manager on larger, more strategic ones

• Lead EBRs focused on measurable outcomes, not product features

Strategic Growth & Advocacy

• Independently build champions within your accounts

• Proactively identify, document, and communicate measurable customer outcomes

• Confidently ask customers for feedback, advocacy, or references once value has been delivered

• Represent the voice of the customer internally, influencing product priorities

Operational Excellence

• Maintain rigorous HubSpot hygiene — every interaction logged, every risk flagged, forecasting accuracy non-negotiable

• Use data (usage, health scoring, churn signals) to prioritise your time across a 70+ account book

• Document and iterate on playbooks so what works becomes repeatable

🧭 What Success Looks Like

• ≥90% Gross Revenue Retention across the portfolio

• Renewal risk identified early and mitigated proactively, not reactively

• Standard expansion opportunities converted directly; larger ones successfully partnered with the AM

• No account left untouched without clear justification

• Clean, accurate CRM — HubSpot up to date at all times

Strong candidates can clearly articulate:

• Specific customer relationships they personally built or rebuilt

• Renewals and commercial deals they've closed themselves, not just supported

• How they identified and mitigated risk before it became a crisis

• What changed for the customer because of their direct involvement

🧩 About You

Essential Skills & Experience

• 3–5+ years in B2B Customer Success, ideally in SaaS or a technical product

• Proven track record managing a large ARR book (500K+) with strong GRR/NRR outcomes

• Genuine commercial experience — you've run your own renewals and negotiated your own terms, not just supported someone else's deal

• Comfortable managing high account volumes without dropping the ball — organised, process-driven, proactive

• Experience with HubSpot (or similar CRM) — you log everything and use data to prioritise

• Confident engaging technical buyers — security teams, SOC managers, IT leads

• Strong written and verbal communication — able to run an EBR, write a renewal email, and escalate a risk in the same afternoon

• Self-starter — comfortable picking up a live book and running with it from day one

🚫 This Role Is Not a Fit If You:

• Prefer working primarily behind the scenes rather than directly with customers

• Are uncomfortable owning commercial conversations and renewals yourself

• Focus more on internal process than customer outcomes

• Need close direction to drive engagement or momentum

• Rely on an Account Manager to run the deal rather than support it

🌟 Desirable

• Experience in cybersecurity, SaaS security, or a technical training product

• Experience in Account Management (owning existing business renewals and expansion)

• Experience managing accounts through a period of operational change or transition

🌱 Traits That Thrive at TryHackMe

• Ownership — "If not me, then who?"

• Bias for Action — progress over perfection

• Customer Obsession — empathy paired with accountability

• Resilience — persistence through complexity

• Craftsmanship — pride in clarity, quality, and impact

Customer Success at TryHackMe is not a support role. It is a growth, trust, and outcomes function.

Why This Role Matters

This book has been split and stretched across a team for too long, and it shows — inconsistent coverage on accounts that deserve better. This role is the fix: one strong owner, running the full lifecycle end to end, with the commercial authority to actually close the deals that matter, and AM support in reserve for when the biggest opportunities need extra firepower.

If done well, this role stabilises and grows a genuinely valuable part of TryHackMe's book — and there's a real opportunity to make it permanent.

The Details

• Contract: Fixed term, ~8 months (maternity cover)

• Start date: Immediate / as soon as possible

• End date: Early June 2027

• Location: Remote-first (UK preferred)

• Reporting to: Head of Customer Success

• Strong potential to convert to a permanent role based on performance and fit

What You'll Inherit

• A well-documented portfolio with HubSpot notes, renewal timelines, and account health flags

• A structured handover from the outgoing CSM

• Clear near-term account priorities already mapped

• An Account Manager available to partner on large expansion opportunities

• A team of CSMs, a CS Team Lead, and a Head of CS to support you

💼 Benefits & Perks

• 💸 Competitive salary + quarterly performance bonus

• 🌍 Fully remote & flexible hours (minimum 4 hours' overlap with UK timezone, 8am–6pm)

• 💻 Tech setup provided (laptop + accessories)

• 🧡 Health insurance (location dependent)

• 💪 £2,500 annual training budget for professional development

• 🧳 Annual all-company retreat

• 🍼 Enhanced parental leave

• 🍕 Virtual team lunches covered by us

• 🎟️ Free TryHackMe subscription for your friends and family

• 💰 401k / Pension plan

Please note that, at this time, we are unable to provide sponsorship.

🚀 Our Hiring Process

1. Application — Submit your CV and a short note on why you're passionate about education & cybersecurity.

2. Intro Call — 30-minute chat to learn more about you (and vice versa).

3. Take-Home Task — Show how you'd approach a realistic customer scenario.

4. Panel Discussion — Deep dive into your task and experience.

5. Final Chat with Leadership — Meet one of our founders and discuss mission alignment.

Apply now at careers.tryhackme.com 🥷