Part Time
$2000/month
40
Mar 2, 2026
Hi! I'm Debbie, CEO of Pineway: an AI-powered platform helping coaches replace 6+ tools with one system.
We have:
- 700+ coaches on our waitlist
- 28 beta users with 61% weekly activation
- A product that works and is almost ready to ship
- Zero revenue (yet)
I need someone to help us turn that waitlist into our first paying customers.
Not in 6 months. In 6 weeks.
If you're scrappy, understand early-stage startups, and know how to make $1 from $0, I want to meet you like yesterday.
WHAT YOU'LL OWN
Waitlist Activation
- Wake up 700 coaches who signed up but haven't heard from us
- Write re-engagement
- Test subject lines, CTAs, and messaging until something works
- Drive waitlist to beta user to paying customer conversions
Email
- Build simple sequences that move people from "interested" to "ready to buy"
- Write weekly
- A/B test everything: subject lines, CTAs, send times
- Report on what's working (open rates, clicks, conversions)
Revenue Experiments
- Run scrappy growth experiments to find our first $1K MRR
- Examples: limited-time early access offers, founder-led outreach, referral programs, webinars, 1:1 demos
- Track what drives signups and revenue
- Double down on what works, kill what doesn't
Performance & Reporting
- Weekly report: what we tested, what worked, what we're doing next
- Bring recommendations, not just data
- Help us understand what to scale and what to cut
WHAT SUCCESS LOOKS LIKE
Month 1: First re-engagement
Month 2: First paying customers ($1K MRR), clear understanding of what converts
Month 3: Repeatable playbook for turning waitlist into revenue ($5K MRR)
YOU'RE A GREAT FIT IF
- You've worked with early-stage startups (pre-revenue or <$10K MRR)
- You've helped a product get its first paying customers
- You understand
- You can write compelling copy that drives action
- You're comfortable with scrappy experiments and fast iteration
- You don't need a playbook — you BUILD the playbook
- Bonus: You've worked with coaches, consultants, or SaaS tools for service businesses
YOU'RE NOT A FIT IF
- You've only worked at big companies with big budgets
- You need detailed processes and playbooks handed to you
- You think "growth" means running
- You can't show me examples where your work directly drove revenue
- You're looking for a stable, predictable role (this is startup chaos)
WHAT YOU'LL GET
- $1,500-2,000 USD/month (based on experience)
- Raises tied to revenue milestones (when you hit $1K, $5K, $10K MRR, you get raises)
- Fully remote
- Work directly with me (CEO) — no layers, fast decisions
- Early equity when you transition to full-time
- Own the growth function from day one
HOW TO APPLY
If you've read this far, here's what I need to see:
1. Record a 3-minute Loom video covering:
- Who you are and what you've worked on
- One specific example where you helped a startup get its first customers (show me the numbers)
- How you'd approach converting Pineway's 700-person waitlist into paying customers
- What excites you about working with a scrappy, pre-revenue team
2. Write the opening paragraph of a re-engagement
3. Pitch me one scrappy growth experiment we could run in the next 2 weeks to drive our first $500 in revenue
If you're the right person, I can't wait to meet you.
Talk soon!
Debbie