Full Time
$13/hr ($2,060 USD per month)
40
Jun 12, 2026
1. Context + Role
Objectionly is a B2B SaaS platform that helps insurance sales teams analyze and coach from their sales calls to save time on call review, ensure compliance, and improve sales team performance. We're a team of four, growing fast at ~150% revenue growth this year with zero down months, and we've reached the point where the two co-founders are doing operational work they simply shouldn't be doing.
This role exists to own everything that falls between the cracks: automations, vendor coordination, inbox and calendar management, meeting follow through, and recurring ops tasks. You are the person who makes sure nothing gets dropped and no task sits on Garrett or Jack's plate that doesn't require them specifically.
IMPORTANT: Apply Here -
2. Results
You will be successful in this role when:
90-Day Success
Garrett and Jack leave every meeting knowing ops follow-through is handled — no task requires a reminder or a second ask
You own the
Fireflies meeting summaries are triaged by you — ops-related action items are spun up in Monday automatically, and founders are only looped in when a decision is required
Inbox and calendar management is fully off Garrett's plate — nothing falls through and Garrett is where he needs to be
Ongoing Success Metrics
Zero ops tasks sit unassigned or unactioned for more than 24 hours after a meeting or request
Monthly affiliate payouts are processed accurately and on time every month
Fractional CFO requests are fulfilled same day — documents sent, data compiled, no back-and-forth needed
Vendor and freelancer communications are handled end-to-end with Garrett & Jack CC'd, not in the weeds
3. Responsibilities
Automation & Tools (Primary Responsibility)
Build and maintain Zapier workflows across our stack (Close CRM,
Set up and own the Fireflies ?
Maintain and troubleshoot existing automations; flag anything breaking before it becomes a problem
Meeting Follow-Through
Review Fireflies transcripts after every internal and external meeting
Spin up Monday tasks for any ops-related action items
Handle low-level action items directly; escalate strategic decisions to Garrett or Jack
Inbox & Calendar Management
Manage Garrett + Jack’s inbox: triage, respond to routine
Own calendar scheduling: book meetings, send confirmations, protect focus time
Ensure Garrett is always prepped with context before any call or meeting
Vendor & Freelancer Coordination
Manage day-to-day communication with freelancers + vendors (Upwork editors, designers, etc.) — deadlines, deliverables, revisions
Source and vet new vendors or freelancers when needed
CC Garrett on all vendor
Finance & Compliance Ops
Process monthly affiliate payouts accurately and on time
Coordinate with fractional CFO: send requested documents, compile data, manage back-and-forth
Maintain clean records for recurring financial ops tasks
Cancel softwares we no longer use and forgot about
General Operations
Own the
Build SOPs for any repeating process that doesn't have one yet
Handle ad hoc ops tasks assigned by Garrett or Jack — landing page updates, CRM tweaks, tool configurations, etc.
Draft HR and recruiting documents (4R docs, job posts, offer templates) as needed
Review our client success managers EOD reports and flag things that require CEO response
Ensure L10 Boards + metrics sheets are updated prior to L10 meetings
4. Requirements
Must Have Skills
Top Skill: Advanced Zapier proficiency — you can build multi-step automations from scratch without hand-holding
Familiar with CRM based automations in Close CRM
AI First Thinking: Leverage Claude, ChatGPT, and other AI tools to automate recurring tasks off your plate & increase your capacity to take on more work
Experience managing a busy executive's inbox and calendar (Gmail preferred)
Strong written English — you will be drafting
Speed of Execution: All things are killed by slow speed. Ability to move fast and be comfortable in a fast paced environment.
Nice-to-Have
Familiarity with ClickFunnels, Meta Pixel, iClosed, Fireflies
Slightly technical with ability to handle CTO requests without much hand holding
Understand how to build AI Agents
Background in a SaaS or tech startup environment
Experience building or documenting SOPs
Who You Are
Obsessively organized: nothing falls through the cracks, ever
Proactive not reactive: you see what needs to happen and you do it
Comfortable with ambiguity: early-stage startup means priorities shift & you roll with it
Obsessed with learning: Even if you don’t hold every skill in this doc, you’re the type of person that will spend your free time learning how to obtain the skill.
Strong communicator: you can represent Garrett and Objectionly professionally in any
Resourceful: if you don't know how to do something, you figure it out before asking
Protector: You take the role of protecting the CEO/CTO’s time with dignity as wasted time from leadership kills company growth.