SeniorFull TimeEN
🧭 Sales Enablement Contractor (Onboarding, Training & Coaching)
→ Contract • Remote (UK timezone) • Reports to Head of Sales
TryHackMe is the fastest-growing online cyber readiness platform in the world. Our mission is to make the world more digitally secure by making cybersecurity capability development accessible, practical, and fun for everyone, empowering teams to go from good to world class. After a highly successful 2025, we've grown to more than 7+ million community members working with 1,000 companies and our growth is only accelerating! 🥷
Our GTM team is scaling fast across BDR, AE, AM, and CSM, and we need to ramp new hires faster, lift the performance of existing reps, and install a coaching rhythm that drives measurable improvements in sales velocity, win rate, and net revenue retention.
We already have strong support from our Product Marketing Manager, on positioning, ICP, and messaging. What we need now is a dedicated operator who lives and breathes onboarding, training, and coaching, someone who can diagnose skill gaps, build programs that stick, and get into the reps with our sellers week after week.
This is a hands-on contract role, reporting directly to the Head of Sales, designed to sharpen execution across our GTM motion. If you love making sellers better, shortening ramp, and turning sales processes into repeatable playbooks, this is your chance to make an outsized impact fast. You are a revenue enabler and accelerator and love to spend time coaching others and giving great feedback.
We have ambitious 2026 revenue targets and a growing GTM team that needs structured enablement to hit them:
Time-to-productivity for new BDRs, AEs, AMs, and CSMs needs to shrink through a robust, role-specific onboarding program
Rep effectiveness across discovery, demo, negotiation, renewal, and expansion conversations needs consistent coaching and reinforcement
Sales motions and playbooks need to be documented, tested, and embedded so every rep runs a best-in-class process
Call review and coaching cadences need to become a weekly rhythm, not an ad-hoc activity
Enablement content and tooling need to live where reps work, with just-in-time support at every stage of the buyer journey
We need someone who can hit the ground running, assess what's working and what isn't, prioritise ruthlessly, and deliver measurable improvements in velocity, win rate, and quota attainment within weeks, not quarters.
Design and run role-specific onboarding programs for new BDRs, AEs, AMs, and CSMs, reducing time-to-first-meeting, time-to-first-deal, and time-to-first-renewal
Build certification and competency checkpoints so we know when a rep is ready to sell unsupervised
Partner with hiring managers and Product Marketing to align onboarding to ICP, messaging, product, and buyer personas
Build and deliver ongoing training across the full sales cycle: prospecting, discovery, demo, negotiation, closing, renewals, and expansion
Develop playbooks, battlecards, and objection libraries in partnership with Product Marketing, Product, and sales leadership
Run skills workshops, roleplay sessions, and live-deal labs to embed behaviours that compound over time
Sit in on live calls, review recorded calls in Gong, and deliver structured 1:1 and group coaching with clear development plans
Coach our sales managers to coach their teams, scaling enablement through the management layer rather than bottlenecking in a single person
Drive a weekly coaching cadence across BDR, AE, AM, and CSM teams with measurable outcomes and accountability
Own the enablement tech stack and curate content where reps work (HubSpot, Gong, Highspot or equivalent, Claude)
Ensure enablement content is accessible, current, and actually used, retiring what's not landing
Partner with RevOps so the CRM, call recording, and reporting tools support the coaching and training motion
Define and track enablement KPIs: ramp time, quota attainment, win rate, stage conversion, deal velocity, ACV, NRR, GRR, pipeline coverage, and coaching coverage
Report weekly on leading indicators and monthly on lagging outcomes, tying enablement activity directly to GTM performance
Run experiments on new enablement approaches, scale what works, and kill what doesn't
Partner with Joanna on ICP, positioning, messaging, and competitive enablement, operationalising her work across the sales floor
Partner with Product, Content Engineering, and Customer Success to close feedback loops between the field and the roadmap
Partner with RevOps on sales process, forecasting accuracy, and funnel hygiene
Proven experience as a Sales Enablement lead, Sales Trainer, or Revenue Enablement Manager in a B2B SaaS environment scaling through $20-$50m
A track record of reducing ramp time, improving win rates, and lifting quota attainment through structured enablement programs, results over excuses
Hands-on experience coaching BDR, AE, AM, and CSM roles across prospecting, full-cycle selling, renewals, and expansion
Strong command of modern sales methodologies (e.g., SPICED, MEDDPICC, Command of the Message, Challenger, Sandler, Winning by Design)
Experience with call coaching tools (Gong, Chorus, or similar) and enablement platforms (Highspot, Seismic, Mindtickle, or equivalent)
Fluent with HubSpot, comfortable working alongside RevOps to interpret funnel data and turn insight into action
AI-native, you actively adopt Claude and similar tools as coworkers to build content, analyse calls, and scale enablement outputs
Excellent written and verbal communication, with a focus on clarity and precision in every rep and stakeholder interaction
Experience in cybersecurity, developer tools, or edtech
Experience enabling government or public-sector sales motions
Background building certification or accreditation programs
Previous contract or fractional enablement engagements with similar-stage scale-ups
Operator, not architect: you ship programs and coach reps directly, you don't just write strategy decks
Data-led and insight-driven: you measure what matters and let evidence shape the next iteration
Bias for action: you build the first version in days, not months, and improve from live feedback
Buyer-centric: every program, playbook, and coaching moment traces back to what helps the customer buy
Just-in-time mindset: you deliver enablement where and when reps need it, not in quarterly megaproject form
GTM aligned: you connect the dots between Marketing, Sales, CS, Product, and RevOps so reps feel one coherent system
Structure drives freedom: you install lightweight processes that make reps faster, not slower
Coaching-first: you believe lasting change comes from reps doing reps, not from watching slides
Resilient and adaptable: you thrive in ambiguity, raise the bar, and bring people with you
Always be learning: you stay ahead of sales, buyer, and AI trends, and turn that knowledge into sharper sellers
Audited the current onboarding, training, and coaching motion across BDR, AE, AM, and CSM
Sat in on live calls and Gong reviews to baseline rep competency and identify the biggest skill gaps
Delivered a prioritised 60 and 90-day enablement roadmap aligned with the Head of Sales
Started running a weekly coaching cadence with at least one team
Surfaced at least one thing we were not aware of that materially affects seller performance
Shipped a v1 role-specific onboarding program with measurable ramp improvements
Embedded a repeatable coaching rhythm across BDR, AE, AM, and CSM managers
Published a living playbook and battlecard library tied to buyer stages and common objections
Moved at least one leading KPI (win rate, stage conversion, ramp time, or deal velocity) in the right direction with data to prove it
Enabled managers to self-serve coaching, so the system does not depend on any single person
Duration: 3 to 6 months initially, with potential to extend based on performance and project needs
Location: Fully remote, UK timezone required (minimum 4 hours overlap with UK 8am to 6pm)
Working arrangement: Flexible hours with core collaboration time aligned to UK business hours, occasional willingness to work late for US timezone overlap is appreciated
Rate: Competitive day rate commensurate with experience
Reports to: Head of Sales
You will be the operator who turns our GTM ambition into rep-level execution. Your work will directly impact:
How fast new sellers go from hired to quota-carrying
How many deals our AEs and AMs close, and how quickly they close them
How much expansion revenue our AMs and CSMs unlock
How predictably our BDR team builds qualified pipeline
How consistently our whole GTM motion feels to a buyer
Get this right, and every seller we hire gets more productive, every existing rep gets sharper, and the whole business moves faster toward its revenue goals.
Please include:
Your CV highlighting sales enablement, training, and coaching experience
A brief cover note explaining:
An example of an enablement program you have built and the measurable business impact it drove
Your coaching approach and how you hold reps and managers accountable
Your availability and preferred contract terms
We're moving quickly on this hire. Strong candidates will be contacted within 48 hours for an initial conversation.
