Junior Account Executive
Top Benefits
About the role
Critical Cloud
Careers
Junior
Account Executive
Reports to Chris Webb, CRO
Pipeline open Junior
0–2 yrs exp UK Remote / Cardiff Full-Time Scroll
OTE
~£60k
Base
£35–40k
Location
UK Remote
01
Why Now
We have a genuine technical moat, the world's first "Powered by Datadog" certification and we're in the critical window to establish brand leadership in European Datadog-native managed services. You'd be one of the first two AEs, which means the playbook you help write becomes the one the team scales from.
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" 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, 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.
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. Often the first deal and the start 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. High-velocity deals that frequently lead to Managed Datadog.
What You'll Do
→Build and manage a pipeline of tech-led SMB prospects through a mix of outbound prospecting, partner referrals, and inbound leads →Run discovery calls to understand prospects' cloud and observability challenges and map them credibly to Critical Cloud's service portfolio →Own the full sales cycle from first contact through to signed contract, supported by Chris and the delivery team on technical specifics →Work closely with Datadog's own sales and partner teams to co-sell and develop joint opportunities through the Powered by Datadog channel →Develop relationships with TD SYNNEX and AWS/Azure partner ecosystems to generate and progress partner-sourced pipeline →Prepare commercially sound proposals and statements of work, you won't be starting from a blank page, but you'll need to tailor them →Maintain rigorous CRM hygiene: accurate pipeline, activity logging, and forecast data the CRO can rely on →Feed market intelligence back to the team, what's resonating, what objections you're hitting, what competitors are doing →Represent Critical Cloud at industry events, Datadog partner days, and customer meetings, in person when it matters
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
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."
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
Career Path
Start
Junior
Account Executive
Year 1–2
Account Executive
Year 1–2
Year 2–3
Senior AE or
Partner Manager
Year 3+
Head of Sales or
VP Revenue
How We Work
Not a values list. How the commercial team actually operates.
Customer First
The prospects who convert are the ones who felt understood before they were sold to. Every discovery call should leave them thinking "they get it." That means listening more than you pitch, and researching before you reach out.
Stay Curious
You don't need to be an engineer. You do need to be genuinely curious about cloud infrastructure and what's breaking for the engineering teams you're selling to. That curiosity is what makes the difference when you're talking to a CTO who's heard every vendor pitch.
Move with Urgency
Deals go cold when they stop moving. Follow up the same day. Advance every conversation. Make the call when you have 80% of the information, waiting for perfect is how pipeline stalls. Most decisions are reversible.
Earn Trust by Delivering
Your forecast is your word. Your follow-up says who you are. Credibility with the CRO, with prospects, and with yourself is built by doing exactly what you committed to, when you committed to it.
03
Compensation & OTE
On-Target Earnings
~£60k OTE
Base Salary
£35–40k
DOE
On-Target Commission
~£20–25k
At 100% quota
Additional
Certs funded
Datadog, AWS, Azure, contractual
Uncapped commission. Accelerators kick in above 100% quota. You earn what you close.
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
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, a real product, and a CRO who will invest in making you excellent at this.
Join the pipeline
We're not actively hiring right now, but we keep applications on file. 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.
Pipeline open Cover letter required Direct to founders
Not the right fit? Search for Account Executive jobs in Benson No. 35, Saskatchewan, Canada
About Critical Cloud
Critical Cloud operates, secures and governs the cloud, observability and AI runtime layer behind mission-critical software. Your team owns the product. We own the operating layer that keeps it reliable, secure, cost-controlled and evidence-ready, powered by Datadog.
Similar Jobs
Junior Account Executive
Top Benefits
About the role
Critical Cloud
Careers
Junior
Account Executive
Reports to Chris Webb, CRO
Pipeline open Junior
0–2 yrs exp UK Remote / Cardiff Full-Time Scroll
OTE
~£60k
Base
£35–40k
Location
UK Remote
01
Why Now
We have a genuine technical moat, the world's first "Powered by Datadog" certification and we're in the critical window to establish brand leadership in European Datadog-native managed services. You'd be one of the first two AEs, which means the playbook you help write becomes the one the team scales from.
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" 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, 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.
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. Often the first deal and the start 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. High-velocity deals that frequently lead to Managed Datadog.
What You'll Do
→Build and manage a pipeline of tech-led SMB prospects through a mix of outbound prospecting, partner referrals, and inbound leads →Run discovery calls to understand prospects' cloud and observability challenges and map them credibly to Critical Cloud's service portfolio →Own the full sales cycle from first contact through to signed contract, supported by Chris and the delivery team on technical specifics →Work closely with Datadog's own sales and partner teams to co-sell and develop joint opportunities through the Powered by Datadog channel →Develop relationships with TD SYNNEX and AWS/Azure partner ecosystems to generate and progress partner-sourced pipeline →Prepare commercially sound proposals and statements of work, you won't be starting from a blank page, but you'll need to tailor them →Maintain rigorous CRM hygiene: accurate pipeline, activity logging, and forecast data the CRO can rely on →Feed market intelligence back to the team, what's resonating, what objections you're hitting, what competitors are doing →Represent Critical Cloud at industry events, Datadog partner days, and customer meetings, in person when it matters
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
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."
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
Career Path
Start
Junior
Account Executive
Year 1–2
Account Executive
Year 1–2
Year 2–3
Senior AE or
Partner Manager
Year 3+
Head of Sales or
VP Revenue
How We Work
Not a values list. How the commercial team actually operates.
Customer First
The prospects who convert are the ones who felt understood before they were sold to. Every discovery call should leave them thinking "they get it." That means listening more than you pitch, and researching before you reach out.
Stay Curious
You don't need to be an engineer. You do need to be genuinely curious about cloud infrastructure and what's breaking for the engineering teams you're selling to. That curiosity is what makes the difference when you're talking to a CTO who's heard every vendor pitch.
Move with Urgency
Deals go cold when they stop moving. Follow up the same day. Advance every conversation. Make the call when you have 80% of the information, waiting for perfect is how pipeline stalls. Most decisions are reversible.
Earn Trust by Delivering
Your forecast is your word. Your follow-up says who you are. Credibility with the CRO, with prospects, and with yourself is built by doing exactly what you committed to, when you committed to it.
03
Compensation & OTE
On-Target Earnings
~£60k OTE
Base Salary
£35–40k
DOE
On-Target Commission
~£20–25k
At 100% quota
Additional
Certs funded
Datadog, AWS, Azure, contractual
Uncapped commission. Accelerators kick in above 100% quota. You earn what you close.
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
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, a real product, and a CRO who will invest in making you excellent at this.
Join the pipeline
We're not actively hiring right now, but we keep applications on file. 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.
Pipeline open Cover letter required Direct to founders
Not the right fit? Search for Account Executive jobs in Benson No. 35, Saskatchewan, Canada
About Critical Cloud
Critical Cloud operates, secures and governs the cloud, observability and AI runtime layer behind mission-critical software. Your team owns the product. We own the operating layer that keeps it reliable, secure, cost-controlled and evidence-ready, powered by Datadog.