Founding Account Executive

Attention to detail is incredibly important to this role! Please apply ONLY here.

Thoughtly is the voice agent platform built specifically for revenue teams in higher education, mortgage, insurance, and other high-consideration consumer industries. When hundreds — sometimes thousands — of inbound leads arrive every month, most teams can only consistently follow up with a fraction. Thoughtly's agents call, text, book meetings, and log everything back to your CRM, turning every lead into a real conversation. Enterprise teams at 2U, Siemens, and Nomad are augmenting their outbound teams with Thoughtly, with customers seeing close rates jump from 16% to 38% on their lowest-rated leads.

This is a once-in-a-generation opportunity to build for a $1T annual market. Voice agents are just the beginning — Thoughtly is building the first fully autonomous CRM. It doesn't just track work; it does the work. The system of record becomes the system of action. And we don't hand customers a platform and wish them luck — we work alongside their teams to launch agents that qualify more leads, drive more revenue, and sound like their brand. This seed-stage rocket ship is backed by top investors like Armory Square Ventures, Afore, and Greycroft.

About The Role

As a Mid-Market Account Executive, you'll set the stage for how GTM teams of the future work. Your impact will be direct and measurable. We are looking for an Account Executive who is exceptionally organized, can qualify prospects, schedule demos, manage trials, get through security questionnaires and procurement, and can close deals in record time. When you do this job right, you'll drive the adoption of voice AI in GTM teams globally.

What You'll Do

• Own the full sales cycle: sourcing, qualifying, discovery, demo, negotiation, and close
• Run your own demos and guide customers through product integrations (Salesforce, HubSpot, APIs)
• Understand and communicate technical workflows: basic JSON, API concepts, data flows
• Collaborate with engineering for complex technical cases, but stay self-sufficient for most demos and integrations
• Maintain accurate records of sales activities in Hubspot
• Continuously identify and implement improvements to increase efficiency

Required Experience

• Proven full-cycle software sales experience: you’ve owned deals end-to-end and exceeded quota
• Self-starter with a proactive approach to identifying and solving problems
• Excellent written and verbal communication skills, with the ability to craft clear and compelling emails
• Strong organizational skills with the ability to manage multiple deals simultaneously
• Keen attention to detail
• Demonstrated smarts - either in school, in a side hustle, or some other way you've shown you learn quickly, deeply, and well
• Technical fluency: not an engineer, but you can learn quickly, understand APIs, and explain integrations
• Hunter mentality: you’re not afraid to cold call, chase leads, and build pipeline when you’re not closing

Nice to Have

• You use AI in business yourself and/or are AI native yourself (you use Fathom, Gong, or other AI tools)
• Sold to RevOps/GTM teams - understand APIs, Salesforce/Hubspot integrations, documentation, and data flows
• Familiar with compliance-related aspects of selling software, like SOC II, vendor qualification, and other items that need to be completed to get to launch/close.

Compensation

Thoughtly's compensation package includes a competitive base salary and commission benchmarked against real-time market data, as well as equity for all full-time roles. We also offer exceptional benefits. Our compensation range for this role is: $160,000 – $200,000 OTE. Final offers may vary from the amount listed based on geography, candidate experience and expertise, and other factors.