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Careers at Sentinel

Build the engine behind the deals.

We're the reason a platform's next acquisition shows up before a broker ever hears about it — reaching 1,000+ business owners a day, run by a team that treats sourcing like a craft, not a call center.

Team across 9 countries 100+ transactions closed 7+ languages spoken Remote-first, Toronto & San Francisco anchored

How We Think

Four things we don't compromise on.

Everyone here touches a real mandate within their first month. These are the standards that make that possible.

01

Ownership

You own outcomes, not tasks. A qualified call, a closed retainer, a clean dataset — your name is on the result.

02

Speed

A same-day reply beats a perfect memo next week. Owners and partners move fast — so do we.

03

Craft

Every list, every script, every dashboard is built like it will be judged — because it will be, on the next call.

04

Directness

Say the hard thing, kindly, immediately. No politics between a problem and the person who can fix it.

How We Work

Remote-first, results-first.

Nine countries and two anchor cities means the work has to run on trust and clear metrics — not seat time.

Where

Remote-first across nine countries, anchored by hubs in Toronto and San Francisco. Talent first, geography second.

When

Async by default, synchronous when it counts — pipeline reviews and owner calls happen live, everything else doesn't have to.

How we measure

Metrics over politics. Qualified calls, cadence, and closed retainers are visible to everyone, every week.

Who you reach

A direct line to leadership. No layers between a good idea and the person who can greenlight it.

Open Roles

Always hiring for the engine's core seats.

Four seats we're building around right now. Don't see an exact fit? Introduce yourself anyway — see below.

Featured · Sell-Side Desk

Sell-Side M&A Lead — Own the Desk

Full-time · Remote (North America) · Reports to the Founder

Own the sell-side desk: help business owners run a real exit, on warm supply from an engine that talks to 1,000+ owners a day. A P&L, not a job description — you set targets, run your pipeline, and build the desk as revenue justifies it.

View role & apply Ask a question

Base + uncapped share of collected success fees.

Origination

Origination Associate

Full-time · Remote (multilingual a plus) · Reports to VP, Acquisitions

You're the first voice an owner hears from us. Open conversations at the pace of 1,000+ a day across the team, qualify against mandate criteria, and hand off clean, verified targets — no cold-blast scripts, real market mapping.

Apply for this role Ask a question

Compensation discussed on your first call.

Deal Advisory

Deal Advisory

Full-time · Remote (North America) · Reports to Director, Partner Accounts

You advance real deals — from qualified call through LOI to close. Prior M&A, brokerage, or sales-to-owner experience helps you read a target fast and keep momentum on both sides of the table.

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Compensation discussed on your first call.

Technology & Data

Data / Platform Engineer

Full-time · Remote · Reports to Head of Technology & Data

You build and extend the 10M+ record sourcing platform — lead allocation, live partner dashboards, and the systems that let a small team run at a scale most firms can't match.

Apply for this role Ask a question

Compensation discussed on your first call.

Partner Success

Partner Success — Retainer Partnerships

Full-time · Remote (North America) · Reports to the Managing Partner

A full-cycle seat: prospect acquisitive platforms, run the pitch, close the retainer, then hand it to delivery. Paid contractor trial (draw + revenue share), converting to base + commission — approximately $155K OTE at plan, uncapped above it.

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~$155K OTE at plan, uncapped above it.

Why Join

Real deals, not a simulation.

Nothing you'll work on here is theoretical. Every number below is a live mandate, a real owner conversation, a transaction that actually closed.

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Countries on the team
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Transactions closed
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Owner conversations / day
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Languages spoken

"You guys have done a great job generating proprietary deal flow for us and were able to hit the ground running with your methods."

J. Blake, VP of Corporate Development

Don't see your seat? Introduce yourself.

SDRs, closers, researchers, engineers — tell us what you're great at and the languages you speak. We reply to every serious note within two business days.

The Off-Market Brief

Deal-flow intelligence, once a month.

Sourcing benchmarks, sector notes, and how the most acquisitive platforms build proprietary pipeline. No noise — unsubscribe anytime.

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