Sales Enablement - FTC

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:
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.