Founding Account Executive

twentyAI; Charlotte (NC); Hybrid; USD 255,000 - 345,000; Full time

Job summary

twentyAI is seeking a Senior Account Executive to own the US sales cycle from first conversation to close. You will target mid-market and enterprise firms across technology, financial services, insurance and professional services, selling to senior Benefits, HR and executive stakeholders.

You’ll promote a health-tech solution that helps employers lower healthcare costs while improving employee wellbeing, with 300K OTE and uncapped accelerators.

Qualifications

• 2–10 years of closing / AE experience.
• History of meeting or exceeding quota.
• Comfortable with cold calling and creating opportunities.
• Sold into mid-market or enterprise organizations.
• Experience navigating multi-stakeholder sales and ROI storytelling.

Responsibilities

• Build a US territory and pipeline from scratch.
• Prospect via cold calling, LinkedIn, referrals and events.
• Engage senior Benefits/HR and executive stakeholders.
• Lead pilots and value-based ROI discussions.
• Close $100K+ enterprise opportunities with ~5–6 month cycles.
• Shape US playbook, messaging and GTM strategy.

Skills

Closing deals

Quota attainment

Cold calling

Enterprise sales

US market network

Job description

Location: Charlotte, NC preferred | Remote considered

Compensation: ~$300K OTE + uncapped commission & accelerators

Experience: 2–10 years in a closing sales role

Build Something Big in the US

This is an opportunity to join a high-growth European health-tech company at the very beginning of its US journey.

The business has already built a strong international presence and is now seeing significant interest from major US enterprises. The foundations are in place — now they need an exceptional salesperson to turn that momentum into a repeatable US commercial engine.

The Opportunity

They're looking for a Senior Account Executive to own the US sales cycle from first conversation to closed deal. You'll target mid-market and enterprise companies, primarily across technology, financial services, insurance and professional services, selling into senior Benefits, HR and executive stakeholders.

You’ll be selling a solution that tackles one of the biggest and most persistent costs facing employers — helping organizations improve employee health outcomes while delivering measurable reductions in healthcare spend.

What you’ll own

• Build a US territory and create pipeline from scratch.
• Prospect through cold calling, LinkedIn, referrals, conferences and your existing network.
• Develop relationships with senior Benefits, HR and executive stakeholders.
• Identify champions and build multi-threaded enterprise relationships.
• Run discovery and develop account-specific sales strategies.
• Lead customers through pilots and proof-of-value programs.
• Build compelling commercial and ROI cases.
• Navigate complex stakeholder groups through to signature.
• Close $100K+ enterprise opportunities with typical sales cycles of ~5–6 months.
• Support early customers post-sale while the US Customer Success function is established.
• Help shape the US sales playbook, messaging and go-to-market strategy.

We're looking for a hunter, not a caretaker.

You might be a great fit if you:

• Have 2–10 years of closing / AE experience, ideally following an SDR/BDR background.
• Have a proven record of hitting and exceeding quota.
• Are genuinely comfortable with cold calling and creating your own opportunities.
• Have sold into mid-market or enterprise organizations.
• Understand how to navigate complex, multi-stakeholder sales.
• Can demonstrate experience with meaningful deal sizes and longer sales cycles.
• Have an existing network within the US market that you can activate quickly.
• Know how to sell to senior, relationship-driven buyers - not just tech-forward audiences.
• Can create urgency around a problem that customers may have previously accepted as "just part of the cost of doing business."
• Are commercially minded and comfortable building an ROI story.
• Thrive without a perfect playbook or a large support infrastructure.

Experience in health-tech, employee benefits, wellbeing or adjacent B2B solutions is a plus.

Experience at a company selling into similar buyers is particularly interesting — but we care far more about your ability to sell than the logo on your CV.

Why This Role?

Be one of the first: you'll be joining at the point where the US opportunity is moving from "could this work?" to "let's build it."

Own the market: no inherited book of business. No waiting for someone else to create your pipeline. You'll have genuine ownership of the territory and the freedom to build your approach.

Uncapped earning potential: approximately $300K OTE, with uncapped commission and accelerators for over-performance.

Build the playbook: your learnings will directly influence how the company approaches the US market — from ICP and messaging through to sales process and future hiring.

Shape the future US team: this is intended to be the first of several US commercial hires. As the market proves itself, there is significant potential to help build the team around you.

Sell something meaningful: you're not selling another piece of software that saves someone three clicks a day.

You're helping employers tackle a major and growing healthcare cost while improving the health and wellbeing of their people.

As one of the first US hires, you'll have huge ownership, direct access to leadership and the opportunity to shape how the US business is built from the ground up.

If you want a role where you're handed a territory, a playbook and 200 inbound leads, this isn't it. If you want to hunt, build relationships, close meaningful enterprise deals and potentially help build the US sales team around you, we should be talking.