If you’re a consultative, methodical closer who can land big logos and then grow them, this role is aimed right at you. You’ll own enterprise sales cycles end to end, sell AI powered video and avatar agent solutions, and drive expansion across global organizations.
About simpleshow/D-ID
D-ID builds generative AI powered digital people and video solutions that transform text, images, audio, and video into interactive experiences. Their platform supports enterprise use cases across customer experience, marketing, sales, and L&D, with a large creator and developer ecosystem using their self service studio and API.
Schedule
Full time
Remote (role listed in Chicago, IL)
Strategic enterprise focus: accounts with $5B+ in revenue
Complex sales cycles with forecasting and quarterly delivery expectations
What You’ll Do
⦁ Drive new business with large enterprise organizations while also closing smaller opportunities
⦁ Grow ARR by expanding existing relationships into global enterprise partnerships
⦁ Own the full sales cycle from prospecting through close with strong process and precision
⦁ Sell across HR, Learning and Development, and Marketing stakeholders
⦁ Act as a trusted advisor, helping clients adopt avatar agents and AI video to improve business outcomes
⦁ Build and run strategic account plans to support forecasting, consistent execution, and long term growth
What You Need
⦁ Extensive experience in full cycle B2B SaaS sales
⦁ Track record landing and expanding enterprise logos, including six figure deal wins
⦁ Success running complex sales cycles (7+ months) and consistently meeting pipeline generation targets
⦁ Strong outbound prospecting, product demo leadership, and value based selling focused on measurable ROI
⦁ Familiarity with structured sales methodologies (MEDDPICC, Challenger, or similar)
⦁ Ability to uncover pain points, build champions, and drive outcomes in global, matrixed organizations
⦁ Executive presence and strong communication skills with senior stakeholders
⦁ CRM proficiency (Salesforce or similar) and comfort with sales tech (SalesLoft, LinkedIn Sales Navigator, ZoomInfo, etc.)
Benefits
⦁ Base salary plus uncapped commission, plus ESOP
⦁ Remote setup with provided MacBook and monitor or accessories
⦁ Medical, dental, vision, and supplemental coverage options
⦁ 401(k) with 4% employer match and immediate vesting
⦁ 12 weeks paid parental leave (paternity, maternity, adoption)
⦁ PTO: 15 days plus an extra day per year worked, plus paid sick time and 8 paid holidays
⦁ Company paid trips to Miami for sales meetings (typically twice per year) and other incentives
Compensation is structured as a 50/50 OTE split with accelerators and uncapped earning potential. If you can run long cycles, sell value, and consistently bring in enterprise dollars, this could be a strong move.
Happy Hunting,
~Two Chicks…