Account Executive | Enterprise | North Central

Cast AI; Chicago (IL); Remote; USD 90,000 - 150,000; Full time

Benefits offered by this job

401k match

Health coverage

Equity options

Learning budget

Team events

Job summary

Cast AI is seeking a hunter in the North Central US to own new logo acquisition for its cloud-native automation platform. You will prospect, qualify, and close high‑fit accounts, shaping the regional strategy and building champions across technical and financial buyers.

The role emphasizes MEDDPICC or equivalent qualification, strong territory planning, and rapid product learning within a remote-first environment. You will join a fast‑growing team with equity options and learning budget.

Qualifications

• Proven track record of winning new logos in B2B SaaS.
• History of hitting or beating quota with transparent numbers.
• Owns pipeline generation with consistent weekly prospecting.
• Experience using MEDDPICC or similar sales qualification.
• Experience selling technical cloud infra and related ROI.
• Success navigating multi-stakeholder, technical/financial buyers.
• Strong territory planning and ruthless prioritization.
• Willing to learn new product quickly and iterate on pitch.

Responsibilities

• Build and source your own pipeline with outbound focus.
• Narrow hundreds of accounts to high‑fit targets and pursue them deliberately.
• Win new logos end‑to‑end from initial conversation to close.
• Manage disciplined deals with value discovery and mutual close plans.
• Collaborate with CTOs, VPs, FinOps, Finance, and Procurement to build champions.
• Create business cases and ROI narratives per account's cloud spend.
• Forecast accurately and maintain CRM hygiene for leadership reviews.
• Partner with Sales Eng, CS, and Marketing to move deals forward.

Skills

New logo hunter

Quota achievement

Owns pipeline

MEDDPICC

Complex multi-stakeholder

Territory planning

Rapid value storytelling

Quick product learning

Job description

Why Cast AI?

Cast AI is an automation platform that operates cloud-native and AI infrastructure at scale. By embedding autonomous decision‑making directly into Kubernetes and cloud environments, Cast AI continuously optimizes performance, reliability, and efficiency in production.

The old way doesn't work. As Kubernetes and AI environments grow, manual decisions don’t. Cast AI replaces tickets, alerts, and manual tuning with continuous automation that adapts infrastructure as conditions change. Efficiency and cost savings follow naturally from that automation.

Over 2,100 companies already rely on Cast AI, including Akamai, BMW, Cisco, FICO, HuggingFace, NielsenIQ, Swisscom, and TGS.

Global team, diverse perspectives
We're headquartered in Miami, but our impact is international. We take a global and intentional approach to diversity. Today, Cast AI operates across 34 countries spanning Europe, North America, Latin America, and APAC, bringing a wide range of perspectives into how we build and lead.

Unicorn momentum
In January 2026, we achieved unicorn status with a strategic investment from Pacific Alliance Ventures, the corporate venture arm of Shinsegae Group (a $50+ billion Korean conglomerate). Our valuation now exceeds $1 billion, and we're just getting started.

Join us as we build the future of autonomous infrastructure.

About the role

The North Central US is wide open. The territory is full of companies spending heavily on cloud infrastructure, and most of them have never heard a Cast AI pitch.

This is a pure new‑logo seat. You'll own a large patch of the map, decide which accounts matter most, and build the pipeline yourself. No inherited book to manage, no waiting on someone else’s leads. If you love hunting, this is as good as it gets. If you'd rather grow existing accounts, this one isn't for you.

The Americas sales team is in build mode. New sales leadership with deep experience building high‑performing teams has just joined, the US team is set to grow, and the reps who come in now will help shape how Cast AI sells across the region.

What'll You Own?

• Building and sourcing your own pipeline: you run your own prospecting rhythm and generate your own opportunities, with significant time each week dedicated to outbound.
• Turning a large territory into a focused plan: narrowing hundreds of accounts down to the highest‑fit targets and going after them deliberately.
• Winning new logos end to end, from first conversation through negotiation and close.
• Running disciplined deals: opportunity assessment, value discovery, value demonstration, and mutual close plans.
• Multi‑threading across CTOs, VPs of Engineering, FinOps, Finance, and Procurement, and building champions inside each account.
• Building business cases and ROI narratives tailored to each account's cloud spend and engineering maturity.
• Accurate forecasting and clean CRM hygiene, with pipeline reviews presented confidently to leadership.
• Partnering with Sales Engineering, Customer Success, and Marketing to move deals forward and make sure customers see the value they bought.

What'll You Need?

• A proven track record of winning new logos in B2B SaaS - you've hunted, not just farmed existing accounts.
• A history of hitting or beating quota, with attainment numbers you're happy to walk us through.
• A demonstrated habit of owning your own pipeline generation, with a consistent weekly prospecting rhythm.
• Proven experience running deals with MEDDPICC or another structured sales qualification methodology.
• A history of selling technical products (cloud infrastructure, DevOps, observability, platform engineering, or data) and translating them into clear business ROI.
• Demonstrated success navigating complex, multi‑stakeholder deals with technical and financial buyers.
• Strong territory planning skills: you know how to find the best‑fit accounts in a large patch and prioritize ruthlessly.
• An appetite to learn a new product quickly and to take feedback on your pitch and iterate on it.
• Based in the US North Central region.

What Makes You Stand Out?

• Experience with Kubernetes, cloud cost optimization, or the cloud‑native ecosystem.
• Experience selling to software‑first, digital‑native companies with large cloud bills (including from commercial or mid‑market segments).
• Time at a company with a strong sales playbook and enablement culture, ideally during its earlier, high‑growth hunting phase.

What’s in it for you?

• Join a fast‑growing company at the forefront of cloud‑native automation and Kubernetes technology.
• Enjoy a flexible, remote‑first global environment.
• 401(k) retirement plan 100% company match on employee contributions up to 6% of pay (available after 3 months of employment).
• Access UnitedHealthcare plans including medical, dental, and vision coverage.
• Equity options.
• Learning budget for your professional and personal growth.
• Team‑building budget and company events to connect with your colleagues.
• Equipment budget to ensure you have everything you need.

Hiring process

• Screening call with Recruiter
• Hiring Manager interview
• 1-2 additional interviews based on the role
• Culture Check interview with an executive
• *As part of our standard hiring process, we would like to inform you that a background check may be conducted at the final stage of recruitment through our third‑party provider, Checkr.
  *Please note that Cast AI does not provide any form of visa sponsorship/work permit.

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