About the RoleSimile is building a category. The world's largest enterprises are already using simulated populations to make consequential decisions, and the way we sell has to match that reality: precise, substantive, and unmistakably ours. Enterprise sales is how a novel idea becomes a signed contract with the executives, strategists, and research leaders who stake real outcomes on it.
We have a strong foundation: a product that works, early F100 logos, and a land-and-expand motion with real pull. Your job is to own it end to end. You'll define which verticals we lean into, how we price a category that didn't exist a year ago, and what a repeatable enterprise motion looks like at a company still writing its own playbook.
In this role, you will:- Own the full enterprise cycle: From first outreach to signed contract, run the sales motion end to end. There's no channel partner or SDR org to hand off to, which is the point.
- Sell into consequential decisions: Our buyers are F100 executives, strategists, and research leads who stake real outcomes on what we tell them. Show them what it looks like to simulate the outcome before they commit to it.
- Build pipeline, don't wait for it: Research accounts, generate leads, and work outbound and inbound in parallel. Attend the events and conferences where our buyers already are.
- Make the business case, not just the demo: Run discovery, build the ROI case, and negotiate terms. The pitch has to work on people who've never bought anything like this before.
- Land and expand: Once a team sees what Simile can model for one decision, the next one tends to follow. Structure deals so expansion is the natural next step, not a separate sales cycle.
- Build the playbook as you go: There's no category precedent to borrow from. Improve the decks, scripts, CRM workflows, and metrics as you learn what actually works.
- Work close to the founders: Partner directly with our founding team on sales and revenue strategy, and with Customer Success, Engineering, and Product to make sure what we sell is what we can deliver.
- Move fast: Ship outreach, get in the room, and iterate on what's working. Speed is a constraint you sell within, not an excuse.
RequirementsMust Haves- A track record you can walk us through in depth: Quota-carrying deals you closed, and the ones that fell through. We'll ask about both.
- Full-cycle enterprise sales experience: years of quota-carrying closing experience in B2B SaaS, selling into enterprise or upper mid-market accounts.
- Consultative, multi-stakeholder selling: Proven ability to run a sales cycle with several decision makers in the room, not just one buyer.
- Deal size and expansion: History of closing meaningful enterprise and strategic deals and growing them after signature.
- Discovery and storytelling: You can find the real problem in a discovery call and translate a technical product into a business case a non-technical exec will act on.
- Pipeline ownership: Comfortable generating your own pipeline, not just working what's handed to you.
- Organization and follow-through: Highly organized, proactive, and able to manage several deals end to end at once.
Nice to Haves- Founding or early-stage sales experience: You've sold before there was a playbook to follow.
- Category-creation experience: You've sold something the market didn't have a name for yet.
- AI fluency: Familiarity with AI, machine learning, or simulation-adjacent products, and genuine curiosity about how they work.
- A warm network: Existing relationships with decision makers at Fortune 500 or enterprise companies.
Compensation & BenefitsAt
Simile, we provide competitive compensation packages that include base salary, equity, and comprehensive benefits.
- Salary Range: $350,000 - $500,000 OTE
- Note: Final offers are based on experience, specialized skills, interview performance, and relevant training.
- Equity: Grants are available for eligible roles, subject to board approval.
- Health & Wellness: Comprehensive medical, dental, and vision coverage.
- Time Off: Flexible time off policies to support work-life balance.
Our ProcessWe prioritize thoughtful conversations and clear examples of past work. Our hiring journey is designed to help both sides align on fit, working style, and expectations.
Reapplication Policy: To ensure a fair and thorough evaluation for all applicants, Simile observes a
90-day waiting period before reconsidering candidates for the same role.
