About Monte Carlo
Monte Carlo is the agent trust platform that unifies data and agent observability to monitor, troubleshoot, and improve production AI systems. As enterprises prepare to deploy thousands of agents across business-critical use cases, Monte Carlo provides the reliability infrastructure to support them along this AI transformation, from human-guided agents to fully autonomous operations. Founded in 2019 and backed by leading investors, Monte Carlo empowers data and AI teams to ship trusted AI at scale. Learn more at montecarlo.ai
The RoleWe're hiring an Enterprise Sales Manager to lead our Enterprise Americas team — selling into companies with 1,000 to 7,500 employees. As enterprises move AI agents into production, these deals are getting bigger and more cross-functional. We need a leader who can build a repeatable new-logo engine and coach reps to win multi-threaded, executive-level deals.
What You'll DoLead the Enterprise Americas team's forecast, pipeline coverage, and new-logo bookings as it grows from 4 to 6 reps.
Build a consistent outbound culture: inspect pipeline creation weekly, coach messaging, and set the standard for how the team prospects into enterprise accounts.
Coach reps inside live deals on discovery, multi-threading, executive access, and deal navigation — on the calls, not just in the forecast review.
Run disciplined deal inspection and qualification (MEDDPICC, value selling) and teach it so it sticks.
Recruit 1–2 AEs from your own network, and make every rep on the team measurably better.
Partner with SEs, SDRs, marketing, and CS to shape the enterprise motion as it scales.
Hunter turned leader. You were a top new-logo AE, got promoted into first-line management, and have 2–5 years leading enterprise sellers. You still know how to run a deal and you want the next leadership step.
Playbook pedigree. You were trained inside a disciplined, KPI-driven enterprise SaaS org — and can teach MEDDPICC, Command of the Message, or value-based discovery.
Pipeline discipline + builder instinct. You've created a pipeline from scratch rather than inheriting a mature patch, and you're comfortable building a process where none exists.
Talent magnet. You've hired strong reps, developed them, and have people who'd follow you.
Competitive, low ego, coachable. High standards, hands in the work, takes feedback well. Data, infra, or AI experience is a plus, not a requirement.
You want to stay an individual contributor — this is a full-time leadership seat.
You'd rather lead from the forecast call than from inside the deal.
You need a fully built playbook handed to you.
#LI-REMOTE
#BI-REMOTE
Why Monte CarloWe created the data observability category, and we're doing it again with agent trust — you'll build where the market is forming, not where it's settled
Series D, $236M raised, backed by Accel, Redpoint, Notable Capital, ICONIQ Growth, and Salesforce Ventures
Customers include HubSpot, Fox, Nasdaq, Toast, and Mercado Libre — your work ships to enterprises with real stakes
Snowflake Partner of the Year and a verified connector in Anthropic's Claude AI directory
Remote-first by design since day one, and recognized as a Best Workplace for it
Competitive compensation, equity, and a remote-first environment.
Come As You Are
Equality is a core tenet of Monte Carlo's culture. We are committed to building an inclusive global team that represents a variety of backgrounds, perspectives, beliefs, and experiences.
Monte Carlo is an equal-opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.
We are proud to be recognized for our world-class employee experience:
Monte Carlo Named 2025 Databricks Data Governance Partner of the Year
We were recently recognized as the #1 Data Observability Platform by G2 for the 4th consecutive quarter. See our G2 reviews here!
Monte Carlo Named to G2's Best Software Products of 2026
Monte Carlo was featured on Database Trends and Applications (DBTA’s) Trend-Setting Products for 2025!
We are super proud to be named the 2026 Best Place to Work by Built In!
Beware of Imposter Recruiters and Job Scams
All official communication from our recruiting team will come from an @montecarlodata.com email address.
We will never ask candidates to provide sensitive personal information (such as bank details, social security numbers, or payment) at any stage of the recruitment process.
We will never request payment for equipment, training, or application processing.
Our open positions are always listed on our official careers page: https://jobs.ashbyhq.com/montecarlodata.
If you are contacted by someone claiming to represent Monte Carlo but you’re unsure of their legitimacy, please reach out to us directly at [email protected] before sharing any personal information.
Skills Required
- 2-5 years of experience leading enterprise sellers
- Prior success as a top-performing new-logo Account Executive
- Experience in a disciplined, KPI-driven enterprise SaaS organization
- Ability to teach MEDDPICC, Command of the Message, or value-based discovery
- Experience creating pipeline from scratch and building outbound sales processes
- Experience hiring and developing strong sales representatives
- Ability to coach enterprise reps through discovery, multi-threading, executive access, and deal navigation
- Data, infrastructure, or AI industry experience
Monte Carlo Compensation & Benefits Highlights
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Leave & Time Off Breadth — Paid time off is presented as unlimited, with additional references to paid holidays and sick days. Feedback suggests this breadth of time off supports work-life balance.
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Parental & Family Support — Parental leave is listed at 12 weeks, and some profiles cite expanded durations for birthing and non-birthing parents alongside fertility benefits. These signals point to meaningful family support for different parent types.
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Healthcare Strength — Health coverage is described as comprehensive across medical, dental, and vision, often paired with mental-health resources and FSA/HSA options. Feedback suggests these offerings form a solid core of the overall benefits package.
Monte Carlo Insights
What We Do
Monte Carlo is the agent trust platform that unifies data and agent observability to monitor, troubleshoot, and improve production AI systems. As enterprises prepare to deploy thousands of agents across business-critical use cases, Monte Carlo provides the reliability infrastructure to support them along this AI transformation, from human-guided agents to fully autonomous operations. Founded 2019. Backed by leading investors. Trusted by 400+ enterprises including Amazon, PepsiCo, CNN, Nasdaq, and JetBlue.
Why Work With Us
A Built In 2026 Best Place to Work, Inc. Best Workplace 2024, and Newsweek Most Loved Workplace. We're remote-first, solving one of the biggest problems in the AI era: trust. We build fast, ship bold, and have a great time doing it. Come help the world adopt trusted AI.
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Monte Carlo Teams
Monte Carlo Offices
Hybrid Workspace
Employees engage in a combination of remote and on-site work.
Remote-first, local-second. We hire the best person for the role wherever they are, default to async, and cover coworking for everyone. Dedicated offices in eight cities for anyone who wants an in-person day. None of them required.
