Braun Board

Enterprise Account Executive AMER

Monte Carlo · Remote · US

Base
Not disclosed
OTE
Not disclosed
Quota attainment
Not disclosed
Posted
4h ago

Why it matters: OTE tells you what you could earn. Attainment tells you how realistic it is.

Ask: “What percentage of fully ramped reps hit quota last year?”

Still open · checked 2h agoon Monte Carlo's careers page

What Monte Carlo sells

Watches AI agents so teams can trust them

A company that runs AI agents often can't tell when they make a mistake, because the agents work out of sight. This product keeps watch over the data and decisions the agents use. When something goes wrong, the team can see what happened and fix it, so they can trust the agents with real work.

In plain English, from their own job posts. Something wrong? Tell us

More AI & data companies →

The Braun Read

Ask hard questions

Too much is left unsaid. Make them answer before you invest.

Pay
No pay listed at all.
Transparency
Shares 1 of 5: quota, attainment, deal size, territory, sales cycle.
Pipeline
Mostly self-sourced. Great if you like outbound, rough if you don't.
Time on market
Brand new.
Company hiring
Ramping up: posted 6 sales roles in the last 30 days.

Based only on what the posting says. Flags are a starting point for your first call, not a final judgment.

Questions to ask on the first call

Built from what this posting leaves out. How they answer tells you as much as what they say.

  1. 1.

    What percentage of fully ramped reps hit quota last year?

    OTE is what you could earn. This is how likely you are to earn it.

  2. 2.

    What percentage of reps on the team have been here more than 18 months?

    Tenure shows whether people stay long enough to get paid.

  3. 3.

    Has the comp plan changed in the last 12 to 18 months? What changed?

    A plan that changes every year means the goalposts keep moving.

  4. 4.

    Who sits with reps and reviews calls each week?

    Coaching is often what's behind a good or bad attainment number.

  5. 5.

    What are the base and the OTE for this role?

    No point investing hours before you know the number.

  6. 6.

    Why is this role open? Did someone leave, or is it new?

    New headcount is growth. A replacement means someone left. Ask why.

When the offer comes

Save these for later. They land better once they've said yes to you.

  1. 1.

    Can I see the full comp plan in writing, including clawbacks and accelerators?

    What's in writing is what gets paid. Read it before you sign.

  2. 2.

    Can I see the actual comp distribution for the team last year, not just the OTE?

    The spread shows what most reps really take home. OTE is just the target.

  3. 3.

    I'd be walking away from earned commission to join. Is there room for a sign-on bonus to help cover that?

    Leaving money behind is a fair reason to ask. The worst answer is no.

Josh's top five questions for any sales interview →

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The role

Sell Monte Carlo's Agent Trust platform to data and AI leaders at US companies with 1,000-10,000 employees. You build your own territory, generate at least half your pipeline through outbound, and close net-new logos.

Enterprise · New Logo · Outbound

Selling motion

New Logo

Who you're selling to

Buyer:
Data and AI leaders, plus CDOs, CTOs and CIOsIn their words: “selling Agent Trust to data and AI leaders under pressure to make their agents work in production”
Company size:
Enterprise

Pipeline expectations

Mostly self-sourced. Expect a lot of outbound.

Compensation

The posting doesn't list pay.

What is not disclosed

This posting doesn't tell you:

  • Base salary
  • OTE
  • Quota size
  • Quota attainment
  • Average deal size
  • Sales cycle length

The questions above cover the big ones.

Full posting
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 https://montecarlo.ai THE ROLE We're growing our US Enterprise sales team, which covers companies with 1,000–10,000 employees. You'll own a territory end-to-end. You build the pipeline, run the cycle, and close net-new logos on large, semi-complex deals, selling Agent Trust to data and AI leaders under pressure to make their agents work in production. WHAT YOU'LL DO - Build and own a US Enterprise territory: map and prioritize accounts, and generate at least half your pipeline through your own outbound. - Run full-cycle deals from first meeting to signature, landing net-new logos across 1,000–10,000-employee companies. - Lead discovery and qualification with MEDDPICC or Command of the Message, multi-threading from practitioners up to CDOs, CTOs, and CIOs. - Partner with your Solutions Architect on technical evaluations and POCs, and with Support, Pro Serv, and Product Marketing to land and expand accounts. - Bring the voice of the customer back to Product and Marketing: what buyers need from Agent Trust, and where deals win or stall. - Help build the segment: target-account strategy, sales process, collateral, and interviewing future teammates. WHAT WE'RE LOOKING FOR - Enterprise hunting record. 4–5+ years in software sales, with 3+ in a quota-carrying role and consistent attainment on net-new logos. You can point to the deals and the numbers. - Self-built pipeline. You've built a territory from scratch and sourced most of your own pipeline without relying on inbound. - Discovery and deal control. MEDDICC, MEDDPICC, or Command of the Message is how you actually run deals. You create urgency and close on time. - Technical fluency. You pick up complex technical topics fast and hold your own with data engineers and platform leads. Experience in the data, infrastructure, or AI tooling space (Snowflake, Databricks, Collibra, and similar) is a plus. - Team player and builder. You treat your SA as a real partner, work well across teams, and want a hand in shaping how this segment scales. THIS IS NOT FOR YOU IF - Most of your number came from expansion or inbound. This role is about winning new logos. - You need a finished playbook and a pre-built territory handed to you. - You'd rather pass every technical conversation to your SE. - You haven't carried and hit an enterprise quota in the last few years. #LI-REMOTE #BI-REMOTE WHY MONTE CARLO - We created the data observability category, and we're doing it again with agent trust https://montecarlo.ai/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 https://www.montecarlodata.com/blog-2025-databricks-data-governance-partner-of-the-year/?utm_source=chatgpt.com We were recently recognized as the #1 Data Observability Platform by G2 for the 4th consecutive quarter. See our G2 reviews here! https://www.g2.com/reports/grid-report-for-data-observability-spring-2025.embed?featured=monte-carlo&secure%5Bgated_consumer%5D=7d02ec0a-326a-40fa-8a44-fab49f67c5f1&secure%5Btoken%5D=6b3c29d18ea50ae0005295b5c63994f97c01cae81bbd3f9ea6abff73c40fde51&utm_campaign=gate-2063400 Monte Carlo Named to G2's Best Software Products of 2026 https://www.montecarlodata.com/blog-monte-carlo-g2-best-software-product-of-2026/ Monte Carlo was featured on Database Trends and Applications (DBTA’s) Trend-Setting Products for 2025! https://www.dbta.com/Editorial/Trends-and-Applications/Trend-Setting-Products-in-Data-and-Information-Management-for-2025-167115.aspx We are super proud to be named the 2026 Best Place to Work by Built In! https://builtin.com/awards/us/2026/best-places-to-work Beware of Imposter Recruiters and Job Scams - All official communication from our recruiting team will come from an @montecarlodata.com http://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 recruiting@montecarlodata.com before sharing any personal information.
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