🧭 Sales Enablement Contractor (Onboarding, Training & Coaching)

→ Contract • Remote (UK timezone) • Reports to Head of Sales

About TryHackMe

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! 🥷

Why we're looking for you

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.

The Challenge

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.

🔧 Responsibilities

Onboarding

• 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

Training

• 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

Coaching

• 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

Systems, Tooling & Content

• 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

Performance & Measurement

• 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

Cross-Functional Partnership

• 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

🧳 What You Bring

Required Skills & Experience

• 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

Nice to Have

• 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

🔧 Attributes We Value

• 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

🎯 What Success Looks Like

Within 30 days you will have:

• 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

Within 60 to 90 days you will have:

• 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

📄 Contract Details

• 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

🔥 Why This Role Matters

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.

How to Apply

Please include:

1. Your CV highlighting sales enablement, training, and coaching experience

2. 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.