Enterprise Account Executive

ABOUT US

Scalestack is the AI infrastructure for autonomous enterprise GTM.

We built an AI-native platform, trusted by companies like Harvey, Profound and Astronomer. With presence in New York, Miami, London and Buenos Aires, we are backed by strong investors, recently raising fresh capital led by Leonis and the Zapier Fund.

We're building the infrastructure layer that makes enterprise AI agents actually work in production: reliable, data-rich, and deeply integrated into existing systems. The results speak for themselves — $19M in recovered pipeline for MongoDB, 2x CRM fidelity for Redis, and a 92% match rate powering Typeform at 250K records/month.

ROLE DETAILS

• Type: Full-time
• Location: US (Hybrid)
• Level: Senior AE
• Reports to: CEO

THE ROLE

We're looking for a driven, commercially sharp and highly entrepreneurial Founding Senior Enterprise Account Executive based in the US to own and grow Scalestack's revenues in North America. This is a founding sales role: you'll be the first of a group of AEs on the ground, operating with real autonomy and real impact from day one.You will part-own our US commercial and partnership strategy and represent Scalestack in the US Tech ecosystem and regularly at industry and Scalestack events. 

You'll run the full enterprise sales cycle, from sourcing and discovery through to negotiation and close, working with some of the best GTM and RevOps teams in the market. This is a consultative, complex sale: you'll need to understand how companies think about their GTM/commercial motion, and show them concretely where Scalestack creates value. You'll become the best person in the company at explaining and pitching the product.

This role is not for the faint-hearted. You'll need to be comfortable with ambiguity, energised by building, serious about AI, and a builder. In return, you'll have a direct line to the founding team, real influence on how we sell, and the opportunity to shape the commercial playbook as we scale.

If you are successful in driving Scalestack’s commercial goals there is scope for this role to evolve into US sales team leadership.

WHAT YOU'LL WORK ON

Pipeline & Prospecting

• You are excited by the opportunity to build your own funnel. While you are going to be supported by the team, creating new inroads is exciting and thrilling, and not a burden
• You own outbound prospecting into mid-market and enterprise accounts, building pipeline from scratch
• Manage inbound leads with speed and precision, qualifying and advancing opportunities effectively
• Continuously research the market — identifying target accounts, competitive dynamics, and emerging trends and commercial and technical partnership opportunities.

Enterprise Sales Execution

• Run complex, multi-threaded sales cycles (3–6 months) with senior stakeholders across RevOps, GTM, and executive teams
• Execute consultative discovery that uncovers real business pain and connects Scalestack's capabilities to specific workflows
• Build compelling business cases that secure budget and develop internal champions
• Closing 6 figure new-logo deals, navigating procurement, legal, and security.
• Maintain rigorous CRM hygiene, accurate forecasting, and consistent follow-up throughout every cycle
• You use Accord (mutual action plan tool), to be aligned internally and externally

Cross-functional Collaboration

• Work closely with product, engineering, and customer success to shape solutions and feed back market intelligence
• Act as a category evangelist — educating prospects on a new and rapidly forming problem space around AI-powered GTM
• Help build the sales playbook, refine messaging, and define how we approach enterprise deals as the team grows

AI-Native Selling

• Use AI tools creatively and deliberately — in your own workflows and in how you pitch to customers
• Stay sharp on what Scalestack can do and help customers see possibilities they hadn't imagined

WHAT WE'RE LOOKING FOR

REQUIRED

• 5–7 years of B2B SaaS sales experience, with at least 3 years as an Enterprise AE consistently closing six-figure deals
• Proven track record of closing new-logo deals of US100K ARR with multi-stakeholder buying groups
• Experience running complex, consultative sales cycles — you sell solutions and outcomes, not features
• Strong executive presence: comfortable building credibility with CROs, CMOs, VPs, and senior RevOps leaders
• Experience with a structured sales methodology (MEDDPICC or equivalent) — you have a clear framework for how you run deals
• Comfortable navigating contract negotiation, security reviews, and legal discussions independently
• Experience selling to Revenue Operations, GTM, or Sales teams
• Right to work in the United Kingdom
• Comfortable being the first group of AEs in US/UK/EU — you bring your own discipline and don't need a perfect playbook
• Impressive Fluency in English. You know how to express yourself in a convincing way in both written and spoken form. You are passionate about communicating with clarity, precision and depth
• Curiosity about AI, agentic systems, and how enterprise buyers are adapting their strategies. Ideally, you have been building artifacts on your own

PREFERRED

• Background selling AI, data, workflow, platform products
• Background in selling to GTM teams. 
• Experience in an early-stage or high-growth startup environment

YOUR TRAITS

• Entrepreneurial: you find a way, not an excuse
• High business IQ: you can walk into any company, quickly map their GTM motion, and spot where Scalestack creates value
• Clear thinker, good writer: you articulate complex ideas crisply and help customers make sense of hard problems
• Able to gain the trust of your customers and prospects. You become their advisor. 
• All-in: you're excited to stretch yourself and contribute to building something from the ground up

WHAT SUCCESS LOOKS LIKE

30 Days: Deep product knowledge, first discovery calls running, pipeline mapping underway

60 Days: Active pipeline across 10 qualified accounts, first proposals in motion

90 Days: First deal closed or on the verge, clear view of H2 pipeline

6 Months: Consistent execution across the full cycle, contributing to playbook development

12 Months: Delivering against quota, operating as a key commercial voice, shaping how we scale enterprise in North America

COMPENSATION AND BENEFITS

• Competitive salary benchmarked to experience and market
• Flexible and Unlimited PTO
• Equipment reimbursement
• Hybrid. Preference for either NYC or Miami, but we will entertain remote locations in the US
• Real scope to build and grow as the team scales

OUR VALUES

Ownership & Commitment: We take full responsibility for our work, see it through, and hold ourselves accountable to the outcome.

Deliver Results: We focus on outcomes. We ship things that matter, on time and at the right quality.

Insist on the Highest Standards: We refuse to accept mediocrity. We raise the bar constantly and push each other to do the same.

Learn and Be Curious: We ask why, challenge assumptions, and treat every mistake as a chance to get better.

Collaboration: We win as a team. We share context freely and make decisions that are good for the whole.

INTERVIEW PROCESS

We move quickly and tell you where you stand at every step.

• Screening call — 15 min. Mutual fit check.
• Culture fit calls — 45 min each (2 calls, optional third if needed). Alignment on working style and values.
• Skills and technical conversation — 45 min. Deep dive on your experience, past deals, and how you think.
• Take-home or live exercise (optional) — 3–4 hours. A practical problem that reflects what you'd actually be doing here.
• Decision