Future First Advisors is a rapidly scaling Medicare agency onboarding hundreds of agents monthly. We’re entering the most high-stakes season of the year—AEP (Annual Enrollment Period)—and we’re facing a common but lethal challenge:

We’ll write hundreds of policies in Q4… but we don’t get paid until Q1.

We need a financial operator who can help us navigate the cashflow gap, forecast commissions, and avoid scaling into a cash crisis.

What You’ll Own

AEP cashflow model: Q4 burn vs. Q1 revenue timing
Weekly comp liability dashboard for 1099 agents
Forecasts for lead spend, payout velocity, break-even per rep
Scenario planning (low, mid, high CMS approval rates)
Real-time visibility tools so the founder knows exactly when to scale or pull back
Systems to track CMS payments, agent productivity, and margin erosion

You’re a Fit If:

You’ve managed cashflow and forecasting in high-growth businesses
You understand deferred revenue, comp accruals, and variable payouts
You think in dashboards, not just spreadsheets
You can move fast, communicate clearly, and own results

Required to Apply: Submit a 3–5 Minute Video

We want to see how you think, solve problems, and communicate.

In your video, please introduce yourself, then answer these 4 questions:

Screening Questions:

If our Medicare agency is projecting $300K in lead spend during AEP, but commissions won’t be paid until January, how would you model cashflow and payouts to avoid going negative while still scaling agent activity?
What systems or tools would you implement to track weekly agent production, submitted apps, and pending comp liability?
How would you calculate the break-even CPA per policy written, factoring in agent payout, lead cost, and average approval lag?
If cash on hand drops below a 45-day runway mid-AEP, what would your recommendation be: slow down, double down, or reallocate—and why?

Upload your video (Loom, Google Drive, Dropbox—public link)

Send to: reply with video link here on Indeed or send to Will@futurefirstadvisors.com

Applications without video will not be reviewed.

Job Type: Part-time

Pay: $155,699.00 - $171,954.00 per year

Expected hours: 15 per week

Schedule:

4 hour shift
Monday to Friday
On call
Weekends as needed

Work Location: Remote

Future First Advisors

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