Graduate Account Executive

Critical Cloud

• Careers
  
  

Graduate

Account Executive

Reports to Chris Webb, CRO

Pipeline open Graduate Programme UK Remote / Cardiff Full-Time

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OTE

~£40k

Base

£25–30k

Level

Graduate

01

Why Now

The commercial playbook at Critical Cloud is being written right now. There's no inherited process, no established brand to coast on, but there's a genuine technical moat, a CRO who has built and sold a managed services business before, and a clear path to full-cycle closing as the pods grow. We're building the commercial team now. You'd be joining at the moment that matters.

About The Role

The commercial track starts here. This is the entry point for someone straight out of university or with less than a year of experience, who wants to learn how to sell complex technical services to engineering leaders. You will run SDR activity, support the Junior AE, and be developed into a full-cycle closer.

We are the world's first "Powered by Datadog" accredited MSP, a Datadog-native cloud managed service provider built for European tech-led SMBs. Our founders have scaled and exited multiple technology businesses. We operate lean, move fast, and take observability seriously.

You'll be working directly under Chris Webb, CRO, and alongside the Junior AE as the commercial team builds out. Your initial focus is outbound prospecting, pipeline qualification, and discovery support. As the book grows and the commercial team expands, your scope grows with it. This is the structured path to the Junior AE role.

We're building our talent pipeline for this role and welcome applications now.

02

What You're Selling

Motion 01

Adopt

FETCH (trial enablement), HyperCare (post-go-live sprint), LaunchPad (fully managed rollout). Get customers onto Datadog properly from the start. Often the first deal and the beginning of a longer relationship.

Motion 02

Optimise

HealthScan (independent assessment of an existing Datadog estate) and Catalyst (improvement engineering to fix what's wrong). Strong upsell motion, customers already on Datadog who aren't getting the value from it.

Motion 03

Manage

Managed Datadog (ongoing platform management) and Critical Support, our flagship 24×7 managed cloud operations service. Multi-year ARR, Datadog-native, AWS and Azure. The anchor deal in every account.

Motion 04

Accelerators

Eight fixed-scope, four-week capability deliveries, Infrastructure Observability, Code Security, Cloud Security, AI Observability, and four more. Fixed scope, fixed timeline. High-velocity deals that frequently lead to Managed Datadog.

What You'll Do

• →Run structured outbound prospecting across UK&I, researching target accounts, identifying the right contacts, and booking discovery calls
• →Qualify inbound leads and partner-referred prospects: understand their cloud and observability setup before passing to the Junior AE
• →Support discovery calls, initially shadowing, then leading, to build your own ability to map customer problems to Critical Cloud's services
• →Maintain CRM accuracy: every prospect, every touchpoint, every piece of context logged in HubSpot so the team can rely on the data
• →Research accounts before outreach: understand the target company's tech stack, team size, growth stage, and likely pain points
• →Work alongside the Datadog partner team to identify co-sell opportunities and referrals from the Powered by Datadog channel
• →Track competitor activity and feed market intelligence back to the CRO, what objections you're hearing, what's resonating
• →Develop product knowledge over time: you don't need to know Terraform on day one, but you'll be expected to learn what matters to our buyers
  
  

Who You'll Sell To

CTO / VP Engineering

Venture-backed scale-ups, 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."

Career Path

Start

Graduate

Account Executive

Year 1–2

Junior

Account Executive

Year 2–3

Account Executive

Year 1–2

Year 3+

Senior AE or

Commercial Lead

Requirements

Must Have

• →A degree in any discipline, Business, Marketing, Engineering, Computer Science, or similar
• →Genuine curiosity about how cloud and tech companies work, you don't need to code, but you need to care
• →Strong written and verbal communication: clear, concise, never generic
• →Coachable and structured, you'll be learning a defined process; willingness to follow it matters
• →Driven by outcomes: you care about hitting targets and understand that activity creates results
• →Right to work in the UK without sponsorship
  
  

Nice to Have

• →Any previous sales, customer-facing, or commercial experience, even part-time or retail
• →Awareness of Datadog, AWS, Azure, or cloud observability concepts
• →Familiarity with CRM tools (HubSpot, Salesforce, or similar)
• →Experience with cold outreach, email, LinkedIn, or phone, in any context
• →A demonstrable interest in the tech industry: podcasts, communities, side projects
• →Understanding of SaaS or subscription business models
  
  

How We Work

These aren't values on a wall. They're how we make decisions day to day and what we'd look for in anyone joining the team.

Customer First

Every cold call starts with understanding what the customer is actually trying to solve. You're selling to CTOs and Platform Leads who've heard every vendor pitch. The ones who book a second meeting felt understood, not sold to.

Stay Curious

You don't need a technical background, but you do need genuine curiosity about what engineering teams are trying to build. The gap between knowing the product and understanding the buyer is what separates average prospecting from discovery that wins complex deals.

Move with Urgency

Pipeline stalls because of slow follow-ups and unmade decisions. Own your pipeline, advance every conversation, and make the call even when you're not sure. Most decisions are reversible. Hesitation has a cost.

Earn Trust by Delivering

Commission is paid on outcomes. Credibility is built the same way. Do what you said you'd do, when you said you'd do it, with the CRO, with customers, and with yourself. That's the whole job.

03

Compensation & OTE

On-Target Earnings

~£40k OTE

Base Salary

£25–30k

DOE

On-Target Commission

~£12–15k

At 100% quota

Additional

Certs funded

Datadog, AWS, Azure, contractual

Commission is uncapped and pays from the first deal. This is how commercial careers start.

We're building our talent pipeline for this role and welcome applications now.

Benefits

25 days

holiday + bank holidays + your birthday off

Certs funded

Datadog, AWS, Azure & AI, contractual

Remote-first

flexible working from day one

• →25 days holiday + bank holidays plus a paid day off in your birthday month, taken in the month it falls
• →Holiday grows with tenure: +1 day per year after your second work anniversary, up to 28 days total
• →Enhanced maternity pay: 26 weeks at your full basic salary
• →Enhanced paternity pay: 2 weeks at your full basic salary
• →Datadog, AWS, Azure, and AI tooling certifications paid by the company, these are mandatory for relevant roles and funded in your employment contract, not at manager discretion
• →Flexible working requests from your first day of employment, statutory right, supported in full
• →Company-provided laptop and peripherals, set up before you start
• →Workplace pension, auto-enrolled
  
  

Who Thrives Here

We're not looking for someone who watched a few sales videos and can talk the talk. We're looking for someone with genuine intellectual curiosity about technology and what engineering teams are actually trying to solve. That's what makes the difference when you're cold-calling a VP Engineering.

The commercial playbook at Critical Cloud is still being written. That means if you show up, learn fast, and produce results, you'll have influence over how the sales function is built and a clear path to the Junior AE role as the commercial team grows.

Chris Webb, CRO, has done this before, built a managed services sales function from scratch, scaled it, and exited. He'll teach you what he knows. The expectation is that you're honest about what you don't know yet, and committed to learning it quickly.

Join the pipeline

We're not actively hiring right now, but we keep applications on file. The cover letter matters most: tell us what draws you to selling technical services, why Critical Cloud, and what you'd want to learn in your first six months. No templates.

Pipeline open Cover letter required Direct to founders

[email protected] →