Junior
Account Executive

Reports to Chris Webb, CRO
Applications Open Junior · 0–2 yrs exp UK Remote / Cardiff Full-Time
Certified Partner
⬡ Powered by Datadog
OTE
~£60k
Base
£35–40k
Location
UK Remote
About the Role
We have a compelling product, a genuine technical moat, and a closing competitive window in the European market. We need someone who can open doors, run a tight sales process, and close. This is a junior role — but it's a real one.

We are the world's first "Powered by Datadog" certified partner — a Datadog-native cloud managed service provider built for European tech-led SMBs. Our founders previously built and exited DevOpsGroup to Amdocs. We operate lean, move fast, and take observability seriously.

You'll be working directly under Chris Webb, CRO — a co-founder who has taken a managed services business from zero to exit. This is an early hire in the commercial team, which means genuine exposure to how pipeline is built, how deals are structured, and how a cloud MSP goes to market. You won't be making calls from a script.

This role is investment-gated and activates on seed funding (~FY26–27). We are accepting applications now to build the pipeline.
What You're Selling
Motion 01
Adopt
Get customers onto Datadog. Discovery, scoping, and a structured onboarding engagement. Often the first deal and the start of a longer relationship.
Motion 02
Optimise
Help existing Datadog users get more from the platform. SLO design, dashboarding, alerting hygiene. Strong upsell motion within existing accounts.
Motion 03
Manage
Critical Support — our flagship recurring managed SRE service. Multi-year ARR, Datadog-native, AWS and Azure. The anchor deal in every account.
What You'll Do
Sales Cycle Ownership

You own the full cycle. Technical qualification and commercial approval sit with the CRO; everything else is yours.

01
Prospect & Outbound
02
Discovery Call
03
Technical Qualify
04
Proposal & Demo
05
Negotiate & Close
06
Handoff to Delivery
Who You'll Sell To
CTO / VP Engineering
Series A–C tech company, 30–150 staff
"We can't justify a dedicated platform team but we can't afford downtime either."
Head of Platform / DevOps Lead
Already using AWS or Azure, Datadog evaluator
"We're on Datadog but we're not getting the value out of it. And I'm the only one who knows how it works."
Engineering Manager
Carrying on-call burden, no dedicated SRE
"Our engineers are losing weekends to on-call. Something has to change before we start losing people."
Requirements
Must Have
  • Some B2B sales experience — internship, placement, SDR, or BDR role — ideally in tech, SaaS, or cloud
  • Genuine curiosity about cloud and infrastructure — you don't need to be an engineer, but you need to care about what you're selling
  • Confident and credible on the phone and in video calls — you'll be talking to senior technical buyers
  • Disciplined self-starter: you'll manage your own pipeline and time without a lot of hand-holding
  • Comfortable with ambiguity — we're an early-stage company; the playbook is still being written
  • Right to work in the UK without sponsorship
Nice to Have
  • Experience selling into technical personas (DevOps, Platform, Engineering)
  • Familiarity with Datadog, AWS, Azure, or cloud managed services
  • Experience with a structured sales methodology (MEDDIC, SPIN, Challenger, or similar)
  • CRM experience — HubSpot preferred
  • Partner or channel sales exposure (Datadog, AWS, Azure ecosystems)
  • Track record of hitting quota or pipeline targets, however early
Compensation & OTE
On-Target Earnings
~£60k OTE
Uncapped commission. Accelerators kick in above 100% quota. You earn what you close.
Base Salary
£35–40k
DOE
On-Target Commission
~£20–25k
At 100% quota
Additional
EMI options
Employee share scheme
This role is investment-gated and activates on seed funding (~FY26–27). We are accepting applications now to build the pipeline.
Career Path
Start
Junior
Account Executive
Year 1–2
Account Executive
Mid-Market
Year 2–3
Senior AE or
Partner Manager
Year 3+
Head of Sales or
VP Revenue
Who Thrives Here

The best AEs we've worked with share one quality: they're genuinely interested in what the customer is trying to build. That curiosity is what makes the difference when you're talking to a CTO who's heard every vendor pitch. You don't need to know what a Kubernetes pod is on day one — but you do need to want to understand it within the first month.

We have a genuine technical moat. The Powered by Datadog certification is rare, our delivery capability is real, and the founders have done this before. Your job is to get that story in front of the right people — and then close. Chris will show you how.

This is a small, commercial-minded team. There's no SDR to hand off your research to, no enterprise deal desk, and no brand awareness to coast on. What there is: real commission, real equity, a real product, and a CRO who will invest in making you excellent at this.

Ready to apply?

Send a cover letter and your CV. The cover letter matters most: tell us about the best conversation or deal you've run — what made it work, and what you'd do differently. No templates.

Applications open Cover letter required Direct to founders
careers@criticalcloud.ai →