Outbound & CRM Systems Operator

Windsor Drake is a boutique investment bank focused on sell-side M&A for founder-led businesses in software, fintech, payments, and tech-enabled services. We run a lean operation and rely on clean systems, disciplined execution, and consistency.

We are hiring an Outbound & CRM Systems Operator to manage the technical execution of our buyer outreach and deal tracking systems. This is a pure operations role. You are not responsible for strategy, messaging, or closing. Your job is to make sure the machine runs flawlessly every day.

Core Responsibilities

Outbound Email Operations

Set up, manage, and monitor cold email campaigns

Load and maintain contact lists provided by the team

Execute email sequences exactly as instructed

Monitor deliverability, sending limits, and inbox health

Pause, adjust, or escalate issues if deliverability degrades

CRM & Data Management

Maintain clean and accurate CRM records

Tag, label, and categorize inbound responses correctly

Update deal stages and buyer status in real time

Ensure no leads, responses, or follow-ups are lost

Inbox & Response Routing

Monitor shared inboxes for inbound buyer responses

Route replies to the correct tea ---------- mber

Escalate high-priority or time-sensitive responses immediately

Ensure response SLAs are met

Process Discipline

Follow documented SOPs precisely

Maintain daily, weekly, and monthly system hygiene

Flag gaps or breakpoints in the workflow

Keep trackers accurate and up to date

Requirements (Non-Negotiable)

Prior experience running cold email systems

Strong attention to detail and process discipline

Comfortable working with CRMs, spreadsheets, and outreach tools

Reliable internet and consistent availability

Clear written English for internal communication

Preferred Experience

Experience with tools like Instantly, HubSpot, Pipedrive, or similar

Experience in B2B outreach, lead operations, or sales ops

Familiarity with email deliverability basics (domains, warming, limits)

Experience supporting professional services or B2B teams

What This Role Is Not

Not a strategy or copywriting role

Not a sales or closing position

Not a creative or marketing role

You are here to execute cleanly and consistently.

Performance Expectations

Zero missed responses

Clean, accurate data at all times

Stable deliverability and system uptime

Reliable daily execution without reminders

Compensation & Structure

Competitive monthly pay based on experience

Long-term role for strong performers

Clear responsibilities and documented processes

How to Apply

Please include:

A brief summary of your experience with cold email and CRMs

The tools you have used previously

Your availability and time zone

We value reliability, precision, and follow-through. If you take pride in running systems that do not break, this role will suit you.