Head of Sales

Userled
Onsite Full Time GTM forecastingMEDDICMarketingSaaS £100K – £140K 2x OTE uncapped
London, United Kingdom Onsite Full Time Posted 4 hours ago Apply before 21 Jan 2027 5 views
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Job Description


First of all, if you love selling, building, and leading from the front, you’ll love this role. If you’re only looking to manage from a distance, it’s probably not the right fit.

Userled is at a real inflection point. The momentum is tangible. We’ve sold to some of the largest companies on the planet, 2.5x’d revenue in 2025, and we’re aiming to do the same again in 2026.

As founder, I can’t keep leading the org alone. I’m looking for someone with true 1–10 experience to join me on this mission. Someone who wants to build something meaningful. I’ll happily work for you as an AE while you continue shaping and elevating the sales culture at Userled, built around excellence, intensity, and rolling out the red carpet for our ICP clients.

Userled is about personalising the buyer journey with AI for key accounts. If we can’t execute that ourselves at the highest level, we don’t deserve to win. It’s that simple.

We hold ourselves to a very high bar when closing ICP deals. If you think you’ve seen strong enterprise execution before, I genuinely think you’ll be impressed by the standard we aim for.

If your strength is coaching great discovery, demos, and multi threading, that’s important. But here, we go further. We win post demo through relationships, personalised ads, tailored content, and deep account execution, using our own platform to lead by example.

The BDR org is central to our growth. Each AE is paired with a BDR to win together, building pipeline, working the full funnel, and pushing deals over the line as a team. Right now, 60% of our pipeline is inbound and ICP fit, which is a great place to be. But we’re building for durability, not luck.

We’re looking for someone with a hunter mentality who enjoys getting into the trenches with the team, showing the way, and building a revenue machine the right way.

If that excites you, we should talk.

About Userled


Userled helps B2B companies personalise the buyer journey for their key accounts using AI.

We’ve sold to some of the largest companies in the world, including Stripe, Square, Datadog, Canva, Elastic and more.

The Role


This is not a “VP who reports on pipeline” job.

You will:


  • Own revenue and quota
  • Lead, coach and hire AEs and BDRs
  • Still carry a bag and close key deals
  • Drive outbound with the team (hunter mentality required)
  • Build the operating rhythm: forecasting, MEDDIC discipline, deal reviews
  • Improve win rates post-demo (where enterprise deals are actually won)
  • Partner closely with Marketing on ICP expansion
  • Scale what’s currently working (60% ICP inbound) while building a repeatable outbound engine

At Userled, we win deals post-demo through:


  • Deep multi-threading
  • Account-based execution
  • Tailored content
  • Personalised ads
  • Strategic relationship building

If your version of sales enablement is just “teach better disco and demo”- this won’t work.

What Great Looks Like


  • You’ve scaled B2B SaaS revenue from 1–10M+ ARR
  • You’ve built and managed AE + BDR teams
  • You’re deeply comfortable selling to mid-market and enterprise
  • You are a hunter, not just a manager
  • You hold a high bar for execution and intensity
  • You care about craft, not just CRM hygiene
  • You want to build a culture around excellence and effort

Culture


We believe in:


  • Excellence over average
  • Hard work over shortcuts
  • Rolling out the red carpet for our ICP accounts
  • Winning through depth, not volume

This is not a lifestyle role.

This is a build-something-serious role.

Location


  • London-based.
  • 4 days per week in the office.

Package


  • Competitive 100K-140K 2x OTE uncapped
  • Meaningful equity 0.5-1%
  • Opportunity to define and scale the revenue org
  • Direct partnership with the founder

Comp is designed to attract true builders, not caretakers.

If you’ve done 1–10 before and want to do it again properly let’s talk.
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